Totally original by me...historic details of train ride shortened to fit this thread.
Conducting Her Business
by EroticWriter
"All Aboarrrrrrrrrrrrddd!" The conductor’s deep voice rang out, loud enough to be heard even above the sounds of the hissing steam coming from the engine. The train station in Indianapolis was bustling, with trains on several tracks, all getting ready to go somewhere, something that was happening 24 hours a day now that the USA was at war.
Mary was already aboard, aided by the helping hand of the Pullman conductor as she had climbed the stairs, two bags of luggage in hand.
"Looks like this is your first time to ride a train," the white-haired black conductor commented.
"How did you know," Mary asked, her eyes bright with excitement?
"Oh, we can always tell miss. The way your eyes started taking it all in soon as you got on board. I can remember, wayyy back, my first train ride."
"Really? How old were you, and where were you headed?"
The conductor laughed. Mary already liked this man. This was the first time she had ever had a conversation with a black man, and she already felt completely relaxed with him.
"Let me help you with those bags while we find your seat, and then I'll tell you about my first ride." The conductor took both bags and lead Mary down a corridor past some sleeping compartments and stopped at the first seat forward of the last sleeping compartment they had passed. "I think you'll like sitting here miss, with the wall behind you. That way there's no one directly behind you to make you feel like you are being watched from behind."
"Would anyone be watching me," Mary beamed?
"Probably, miss. You're a very pretty young lady."
Mary giggled. "Tell me about your first train ride."
The conductor held out his hand. "In a minute. The name is Sheldon, miss. And what might yours be?"
"I'm Mary, and I am on my way to Long Beach, to go to work at the shipyard. My sister is there already and has an apartment we can share. So how about your first train ride?"
Sheldon laughed. "It wasn't actually a train ride. I was going to work, first day on the job and I had never been on a train before."
"Were you a conductor right off the bat?"
"Noooo ma'am. I worked as a busboy in the dining car. Then I became a porter. It took me 22 years to work up to where I am today." I spend more time on the train then I do at home."
Sheldon looked around. "Let me take care of some other passengers that might be needin' help, and then I'll come back and see how you are doing."
"That will be great. Thank you. It's nice to have someone to talk to."
Sheldon was off, and Mary had time to settle in. She had arrived a few minutes early, and the train was due to pull out in another ten minutes.
Mary looked up. Sheldon was back and looking down at her with a smile on his face. She brightened. "Oh, you're back already."
Sheldon nodded. "And I see by your ticket that you didn't buy a private sleeping compartment. That means you will be using one of our bunks with the curtain pulled.
"I know, but my money is kind of short. Sally, that's my sister, says that my pay will pretty good once I get to the ship yard, but that doesn't help me today."
Sheldon nodded. "We have some 'Roomettes' in the next car back." He lowered his voice. After it's dark, maybe I can let you slip into one for a few hours to catch some sleep. That way you will at least have a door you can lock instead of just a curtain. No one has to know."
"Really? You'd do that? That would be so nice."
"A roomette doesn't have a sink or a...toilet in it. All it is is a small compartment big enough for two to ride in, and the seat folds down across the room to sleep on. It has a small closet with hangers also. You will still have to go down the corridor to use a bath."
"Well, keep your eyes peeled for me. If no one is using a roomette, it would sure beat having to crawl in and sleep behind a curtain."
"Sheldon nodded. He checked his watch. "Mary, I'll be back later."
"Thank you."
Mary sighed as Sheldon walked off, heading down to greet some other passengers whom apparently had been late arrivals and were rushing down the aisle. Mary had been writing to her sister Sally for weeks now, and after Mary's husband Dave, who was in the Navy, had come home for 'shore leave' after two months of Navy Boot Camp and then gone off to his new assignment in the Pacific Fleet, Mary had decided to take Sally up on her invitation to work with her in Long Beach.
Sally had assured her: "When Dave comes home on shore leave, you will be close enough to San Diego to see him while he is in port. So working at the Long Beach yard would be real convenient for you."
Mary was assured a position as soon as she arrived since she had already had a year's experience working in an office, so her secretarial skills would come in handy. Her husband had completed his boot camp six weeks ago, came home from the Great Lakes Training Station, which was conveniently close to Indianapolis, and spent the better part of two weeks mostly in bed with Mary. Then he had taken the train to San Diego. Mary was following him by about three weeks, but would probably not see her husband until he came back into port. Since this was wartime, and Mary didn't even know where her husband's ship was headed due to secrecy, she might not see him for months, maybe years.
Dave had said that the scuttlebutt was that their ship was headed to 'Pearl' first, which meant Pearl Harbor in Hawaii, but that was just scuttlebutt and he could end up anywhere.
It was summer, 1943. America had been at war since December, 1941, and so far the news, after several months of bad, was looking good for the US forces in the Pacific. Japan was on the run, and American's Naval fleet had been rebuilt into a formidable fighting force, ready to conquer Japan in hopefully, just a few more months. "Win the war in '44' was the motto, and Mary could only hope that Dave's ship came through unscathed.
"You'll really enjoy it here, Sally had told Mary on the phone just yesterday after Mary had told her that she had purchased a train ticket and would be coming out. "There's a NCO club here, with lots of sailors to meet and dance with, and since they are all so lonely, you won't ever have to buy a meal, or a drink if you want one."
"Sally...why in the world would I want to dance or drink with other men? I'm happily married to Dave, remember?"
"I know. I didn't mean that you would actually DO anything with them. I just meant that it will be nice for me to have someone to accompany me when I go out, that way men won't be trying to pick up on me so much."
"I thought you told me that you hoped to meet someone...nice."
"I do, but all these guys are here for a few days or weeks, and then they are gone. And all they want to do while they are here is get laid."
"Sally! You haven't been doing...that, have you?"
"No, not really. But some of the guys I have met were pretty nice."
"Not really? What does that mean? Did you do it, with any one of them?"
"Well....."
"Sally?"
"Yes. But just one or two. It was no big thing."
Mary was shocked, but she should have known. Sally's 'one or two' was probably four or five. After all, Sally had been away from home for over a year now, and Mary had heard that things, that people were a 'lot wilder' in California. "Well, since you are no longer 'saving your virginity,' I hope that you are using 'protection."
"I carry them in my purse, just in case."
Mary was shaking her head, but of course on the phone Sally could not see her. "If I go anywhere with you, I expect you to be the perfect lady with me, O.K.? I'm married, faithful, and plan to stay that way."
"Sally had laughed. "Don't worry. When you are out with me I will be the perfect young lady, and you can keep me straight."
Mary nodded her head, and again Sally could not see. "Besides, Sally, I am pretty sure I am pregnant."
Silence. Then: "You think you are pregnant? How do you know?"
"Dave was here for two weeks, and spent the entire time in bed with me. I missed my period last week, so I'm pretty sure I got 'knocked up.'"
"What about your job, with me?"
"If I am pregnant, I will work until I get too big to work comfortably, then I will catch a train home to have the baby."
Sally sighed. "Well, that will work out I guess. But I was sure looking forward to having you around with me until the war ends."
"That won't be too long, Sally. I hear we will win the war in '44."
"I hope so." (Actually, the war in the Pacific would go on until September of 1945, but they didn't know it at the time).
That had ended their phone conversation, with Mary telling Sally when and at what time her train was supposed to arrive in Los Angeles, and Sally had told Mary that she could catch a 'red car' which was an electric trolley, from Union Station in Los Angeles all the way to Long Beach.
The train was rolling now, and had left Indianapolis way behind when Sheldon approached Mary, who, after staring out at the scenery for several minutes, had finally settled into reading a magazine.
"We'll be serving in the dining car starting in about 15 minutes." Sheldon looked at the watch on his wrist, "in exactly 14 minutes actually. So, when you are ready, just come forward two cars and take a seat. I've already told my co-workers there to take good care of you."
"Thank you Sheldon. That will be nice, and I'm starving."
"Our food is excellent. See you there."
The train was swaying, and since Mary had been seated the entire time the train had been rolling, she found it strange at first to get her balance and walk in a straight line. Fortunately the train had lots of handle type stuff to grab onto if need be.
Sherry had to open doors at the end of each car, and it was noisy going across the vestibule between cars. Even though the area was closed in, you could see out the sides of the floor and watch the earth moving past below you. It made you very aware that you were on a moving train, and right below your feet were two rails, going clickety clack in a steady rumble.
Mary came into the next car, and was surprised to see what looked like at least 40 soldiers, all young white males in uniform, and when she walked into the car, she heard someone seated beside where she was walking yell out: "Eyes center!" No one turned their head to stare, that would be too obvious. But she knew they were looking as she went past. All the seats in this section were facing forward, and each and every soldier could stare at her ass as she walked by. On the way back, they would be seeing her from the front, and be able to take in her face and tits, and all without turning a head.
Just like that, Mary found herself being stared at by 40 pairs of eyes as she walked past row after row of seated soldiers, all young, and all horny. Fortunately, they were respectful and not a word was said to her as she walked by, but Mary's face was red as she left that car and moved on forward to the dining car.
Her meal was excellent, just like the home-cooked meals she was used to, only better since at home they had to use ration books to make some food purchases, and there seemed to be no shortage of food in the dining car. And the two stewards, attractive young black men wearing white who served her were polite, and were perfection in motion as they served the passengers. Sheldon stopped by to see how she was doing, and Mary could not give enough praise to how good the food was and also the service.
She giggled. "I sure got a lot of stares though when I went through that last car. Every soldier in the place was looking at me it felt like."
"I am sure they were. Like I said, you are a very attractive young lady. I hope that none of them said anything they shouldn't have to you..."
"No. Just looking. I could feel my face burning time I got past."
Sheldon laughed. "You probably felt something else burning besides your face since they were all facing forward when you went past."
Mary was surprised at Sheldon's sexual innuendo, but took it in stride. "I said my face, but I could feel my backside crawling, maybe not burning, but I was aware of what they were looking at."
Sheldon nodded. "And you will have to run that gauntlet again on the way back, this time from the front. But I think I have some good news for you. I have a room you can use, a roomette with just a bed like I said, and it won't cost you anything. Just keep it to yourself." Sheldon had lowered his voice to show that they had to be 'confidential' about this.
"I understand. Thank you."
"I'll come back later and let you know the number of the roomette."
Mary again had to run the gauntlet, and this time, no one, well hardly no one, was obvious in staring at her since she could meet their eyes with hers if she wished. But she knew that they were staring, especially after she had gone past each aisle. She sensed that after seeing her face and chest, they were turning their heads this time since she was looking the other way, and again staring at her ass. Her ass was quite nice, and Mary deliberately let it sway, and she could feel every eye in the place on her rear as she went by. Face and tits front, ass and legs rear, and Mary had it all.
She half expected some soldiers to come back, looking for her, and did not know that they had been told to remain in the assigned car.
Clickety clack, clickety clack, click click clickety. Mary almost dozed off from the soothing sound of the steel wheels passing over the rails. .
Once it got dark, Mary was back in her seat with nothing behind her but a wall. This car was not fully occupied and she had some privacy. As Sheldon approached, he said, 'Move over."
Surprised, Mary moved over and Sheldon sat himself beside her, but not so close that his hips touched hers. "Mary. You said you were low on money. Could you use some to get set up when you get to Los Angeles?"
"Yes, of course." She giggled. "Do you have a job for me in the dining car, perhaps? Those two guys that were serving me were kind of cute."
Sheldon was pleased. If she had said that two black guys were cute, that was encouraging. "No, something different. The pay would be very good, and for just giving maybe an hour at the most of your time."
Mary didn't ask, so Sheldon went on. "I see that you are wearing a ring, so I assume that your are married, or maybe just wearing a ring so no one bothers you."
It sounded like he was asking in his last sentence, so Mary answered. "I'm married. My husband is sailing off somewhere with the Navy and I don't know when I will be seeing him again."
"I see. Do you plan...don't take this wrong, do you plan to stay 'faithful' to him all the time he is gone?"
"Well, yes, of course. That's what wives are supposed to do, isn't it? Especially military wives."
"Can I ask you something without you getting upset? It is a chance for you to earn some real money, and no one would ever know."
He was speaking very softly, and Mary leaned towards him and said, "Who do I have to kill?"
Sheldon smiled and went on. "All those soldiers that were looking at you, they were very impressed with what they were seeing."
Mary was beginning to catch on. "All those soldiers? If you are hinting at what I think you are, that's way too many men for me!" Mary laughed, like she was joking, because though it sounded like Sheldon was asking if she wanted to take all those soldiers to bed, she didn't really think so. It must be something else. And then Sheldon surprised her. What she had been thinking was true, except for the numbers.
"They all got together and came up with something. They just finished basic training at Ft Dix in New Jersey. They got paid, and haven't had a chance to spend any of it. So they all said they would put three dollars apiece into a pot, and whoever won the drawing would..."
Mary cut him off. "They want to do a drawing to see who would get to...sleep with me? Is that what you are saying?"
"It was their idea," Sheldon said defensively. I am just the messenger, offering you a chance to earn some real cash if you are interested."
Mary was silent for a while. Sheldon said, "Think about it while I make my rounds again, and then I'll be back."
Mary interrupted before he could leave. "And how much money are we talking about here?"
"There are 40 men, actually, to me they are just boys they are so young, and they all agreed to participate. So at three apiece, that comes to $120 and I would keep $20 for my efforts, arranging a place for it to happen, and changing the sheets afterward."
Mary for some reason found herself thinking it over, something she would never have dreamed in a million years that she would do. But she was low on funds, curious after hearing her sister admit to screwing around, and besides, now that Mary was pregnant, she was 'safe.'
"So my 'cut' would be $100, is that right? And for how long?"
"Yes, $100 and I would give it to you in advance. Time-wise, as long as it takes, one time, five minutes, or thirty, that would be up to you and whoever wins the drawing. But I could set a time limit if you like, and knock on your door after a certain time."
"But if I do this, then I would have to see them, all those men in the morning, and they would all look at me, and know what I had done. I don't think I could handle that."
"No ma'am. That would be no problem, because they are getting off when we stop at Ft Riley, Kansas. So when you get up in the morning, they won't be here."
"Will I be using a roomette? I remember you said they had no bathrooms in them."
"Yes, but there are towels in there, and I'll tell whoever wins to use the bath down the hall first if he needs to."
Mary hesitated, then..."I'll do it. Let me know what time, and show me which room."
"I'll go tell them to take up the money and have their drawing, then I'll come back and show you to your room."
As she waited, Mary was filled with excitement. A hundred dollars in those days, was a lot of money. And all she had to do was let some young soldier fuck her. Easier said than done, but she had decided that the money could go a long way in helping her get settled in California.
Ten minutes later Sheldon was back. "They're picking a winner. I don't think I've ever seen a group of men so excited before. Come on and we'll get you set up in a room." Sheldon led Mary down a corridor, into the next car, and taking out a key, said, "Here we are." He opened the door, and Mary entered a small but comfortable sitting area with a seat that faced front only. "Here is how we make up the bed."
Sheldon quickly pulled down the seat, making it into a bed in short order. He reached up into a compartment overhead and pulled out two sheets. Within one minute he had made up the bed, one sheet under, one on top, and had placed two small pillows in place. .
"You can see that there is not much room to move around on the floor once the bed is down, but you really don't need anything but the bed for what you are going to do." Put your suitcases under the bed for now, and if you have a purse, you can put it up there for safekeeping or if you don't feel safe about it, I can hold anything of value for you while the man is in your room."
"I trust you. Keep the hundred until after he has left and give it to me later."
"If you need to use the bath, it's the last door on the right. Get that over with while I go see who has won and I'll collect the money before I lead him back here. Will you be ready in say, ten minutes? If so, I'll knock on your door and let him in."
Mary gulped. "Should I be...naked when he comes in?"
He laughed. "Well, if you are, I can guarantee that I'll be getting a good look at you too." Then Sheldon took on a more serious tone. "I suggest maybe you should be wearing a nightgown." Sheldon reached into his pocket and pulled out a package, which Mary recognized to be a rubber. Then, thinking it over, Sheldon pulled out a second rubber and handed them both to her. "The second one is in case he breaks the first one with his fingernail or something."
"I'll probably put it on for him. I like doing that for my husband. What if he wants to use the second one to do it twice?"
"You are only committed to one time. Any more than that is your choice."
"It'll be just once, believe me. I just want the money."
Mary had not thought about rubbers. She had not placed one on her husband for those two weeks, and they had agreed that if she got pregnant, that would be fine. She was pregnant now and did not need a rubber, but did not tell Sheldon. Maybe she should have the guy put it on anyhow since right on the package it said 'for the prevention of disease.' Besides that, after doing it for her husband so many times in the past, Mary knew that rolling a rubber over and down a hard dick gave a woman a really good opportunity to handle and study the dick in detail.
If she was going to be having a strange dick, Mary wanted to know what it looked like since it might be the only one she ever has besides Dave.
"I'll be back with the winner in ten, maybe 15 minutes."
Sheldon left, and Mary immediately headed for the bathroom and took a pee, then washed her snatch thoroughly with a damp cloth. She looked at herself in a mirror, and spoke to it like it was her husband and he could hear. "Dave, you will never know what I am doing, but a hundred dollars is a lot of money and I can use it, and besides, I'm curious. I've never been with another man, and this is probably my one and only chance. If a baby is on the way, pretty soon I will be a mother, living back at home where my mother will be watching over me, and besides, in another couple of months I'll be too fat to fight as they say, or in my case it will be too fat to fuck."
Quickly, so she could be wearing her nightclothes, she rushed back to the roomette.
'Knock knock!" The sound startled Mary, though she had been expecting it. Slowly, her body shaking a little, she stepped off the bed down onto the floor and reached for the door handle. "Yes? Who is it?"
"It's the porter, miss."
Mary opened the door a crack, and seeing Sheldon and a young soldier behind him, she quickly opened the door and both men stepped in. Sheldon quickly closed the door behind him and said to Mary, "This is Tyler, the winner of the raffle. I told him to treat you with respect since you have never done this before and that he gets a reasonable amount of time to do the deed.”
He pulled out his pocket watch. “The train's next stop is St Louis in a little over 30 minutes so if you are still busy in here and the train starts slowing, don't let it concern you."
He looked directly at Mary, who was now dressed in a shortie nightie. "Are you O.K.?"
"Yes, I'll be fine, thank you." Smiling, Sheldon quickly took another admiring glance at Mary and left the room.
Mary had decided to wear something that until now only her husband had seen. In the process of looking sexy for Tyler, she had also been giving Sheldon a nice display of legs, and under the top half of her nightie, her nipples could clearly be seen outlined by the thin material.
"Hi."
"Hi, yourself," Mary replied. Tyler was tall, thin, and kind of nice-looking, in a country way. She looked at Tyler's uniform. "I guess you need to take that off." Upon seeing him, Mary had already decided that she wanted to fuck Tyler without his wearing a rubber. 'Skin to skin' is best, Dave had always said. Besides that, Mary was taking this one shot for fun, and in the case of Tyler, she wanted to feel his shot inside her.
"Yes, ma'am." As Tyler carefully removed his outer jacket and then the shirt under, he folded them neatly and put them precariously on a counter along one wall. Mary smiled. "There's a little closet over there with a few hangers you can use."
"Thank you." Mary crawled back up onto the bed, and in the process gave Tyler a brief peek at her inner thighs. She was wearing no panties, and Tyler caught just a quick glimpse of hair. His eyes grew wide as he sped up, struggling to get his T-shirt off, then bending down to remove his shoes before pulling off his trousers.
With them all hung on hangers, one thing remained. He looked at Mary, and she was watching. With his face red, he slowly undid his underwear, which was white with buttons all the way down the front. Before he could get all the buttons undone, his penis sprang out, sticking straight up and pointing at Mary."
"Oh! My! Looks like you are ready." This was only the second adult penis Mary had ever seen, and it was noticeably different than her husband's. This one had no foreskin, and was longer than Dave's by over an inch, but skinnier than Dave's penis both in the head and shaft. Also it was different in that it was straight as a ruler, while her husband's prick curved slightly to the left.
Tyler's face was bright red, and Mary could see it even in the dim light of the room. There was a bright overhead light, but Mary had left that one off. "Ma'am? I've never done anything like this."
"Is this your first time, with a woman?" Mary still had not gotten used to being a 'woman.' All her life she had been a girl, running with other girls. She and her friends still referred to themselves as girls.
"Yes, ma'am. All I've ever done is kiss girls at parties, stuff like that."
"Well Tyler, I'll tell you something that might make you feel better. This is the first time for me too."
He looked startled. "You...you're a virgin?"
Mary giggled. "No, I'm married, but my husband is away in the Navy, and I have never been with anyone else, so you will be a first for me too." She looked deliberately down at his dick. Look at how it is standing straight up. That's the hardest dick I've ever seen, but then, I have only seen two."
"Mine and your husband's?" Dave sounded encouraged, and that was something Mary wanted to do, was encourage him.
"Yes." She reached out and grasped it around the shaft. "It's as hard as a rock. Come on, get in bed with me."
Some kissing, awkward at first until Tyler got the feel of how Mary was using her tongue and began to imitate her. She was already holding his penis in her hand, but Tyler had one arm around her waist, and was lying on his other. Finally, after almost five minutes, Mary asked, "Don't you want to feel my breasts?"
"Oh, yes ma'am." Tyler reached out, touched her right breast, then cupped it, and as soon as he got a good feel, he immediately began climaxing against her belly. "Ooooooh!" His groan was loud and long.
He had said, 'Ooooooh,' and Mary said, "Oh oh!" as she felt blast after blast of hot cum landing on her stomach and running down sideways.
Silence. Mary was still holding his penis, which was for the most part still rigid, but she could feel his warm cum all over her stomach, above the belly button. "I...I got so excited, I couldn't control it. I guess I blew my chance."
Mary giggled. "No, not blew your chance. Our dick is still pretty hard, considering.” Tyler took note of the fact that Mary had referred to his dick as 'our dick,' and he was pleased.
Mary went on, “If you want, we can try again, but first you have to reach over there and grab one of those towels and wipe my stomach."
"I can do it again? Oh boy. Let me get a towel." Tyler sounded just like a little boy, which he basically was, fresh out of high school and into the Army.
Mary could have called it quits at this point, but she had become aroused. Tyler didn't know how to kiss, or how to fondle, and obviously he didn't know how to control his cock, but she had become aroused just the same.
Touching, and being touched by someone strange was having that effect on her. Actually, as she thought about it, knowing that someone was seeing her revealed was turning her on most of all. Mary had first noticed how being looked at had aroused her when Sheldon had stared at her in the nightie.
Now wiped dry, Mary was lying beside Tyler and stroking him. "Ready to put it in?"
"Don't I have to put on a rubber first?"
In answer, she moved her head forward and their lips met. Then two tongues intertwined. She giggled as she gripped his erection. "You get a special treat. No rubber needed because I am one almost month pregnant."
Tyler wasted no time. This was a dream come true. In seconds he was climbing over her and after a brief fumble struggle while he tried to find her hole and Mary ended up by holding and helping him, he was at her lips; Mary instinctively sensed that in his rush to penetrate her, that he would push himself into her too fast and spoil some of the fun.
Quickly, she pushed back against him, bringing his movement forward to a halt. “Do it slow so I can feel and enjoy every inch of that hard cock as it slides in.”
He was shaking, his entire body actually, but he managed to calm down a little as she continued to prevent his entry by pushing back on his cock that was still enclosed within her hand.
“ Yes ma'am.”
She waited another five seconds to be sure that he had regained control of his body, then released her hand.
“Now Tyler, give it to me slow, and kiss me while you do it.”
While she welcomed his warm tongue with one of her own, Mary had to aim his penis once again and smiled around their kiss as she felt his warm flesh part her lips and start in. He was spreading her, not as far as she might want, but it still felt good. Right in the middle of their kiss, she managed to speak. “Ooooh Tyler. That feels good.”
He was going perhaps a little too slow now. “Further Tyler, go on in.”
He pushed a little harder now, and Mary let out a soft 'Aaaaah' as she felt him penetrate. He continued in his slow march forward, stretching his way past her inner lips now and going deeper.
His entry was feeling good, but Mary had hoped for more since this was her first time. Mary was quite wet already, and he was not all that thick, but she wanted to help Tyler to feel like a man. Partially faking, she let out little gasps and then a groan at the appropriate times.
The taking in of his penis and making her groan was partially faking, but the pleasure she was feeling was not. Then, perhaps sooner than she would have liked, he bottomed out, going slightly deeper into her than her husband had ever gone.
"Uuuh Uuuh! Slow down and make it last." Tyler had begun banging away at her. In his lack of experience, he thought the way to please Mary was fast and hard, but she wanted slow, and romantic. "That's right, slow like that. Slow...and easy. That feels better. I learned from experience with my husband, and it felt the same with you.”
She moved her hands onto his ass. “When you do it fast, I can't feel all of your cock as good as I can when you go slow. Do it slow, yes, like that. I can feel every inch of your nice cock as it moves in and out There's no hurry, we can take our time."
"Yes ma'am."
"Now get up on your elbows and feel my breasts. I know you want to since you came as soon as you touched one a while ago."
Tyler almost hopped up onto his elbows and knees and began feeling her breasts, which filled his hands perfectly. Shaped like large apples, they were nice handfuls, and because of their shape, they made her dresses and shirts pop out like a well built bra, except that she did not need to wear a bra, but the times were not yet ripe for a woman to go topless under her clothes
For some reason, perhaps because of Tyler being a virgin, Mary was feeling very ornery and decided to talk dirty. In doing so, she began doing something she had never really done with Dave.
“ Stretch your legs down and put your feet up against mine. That's it, now we are toe-to-toe. Now lay your upper body down onto mine.”
“ But ma'am, won't I squash you?”
“ No Tyler, you're not that heavy. That's right, now we are getting closer. Now put your hands in mine.”
Tyler did, and as their hands locked together, Mary raised her arms out above her head and pulled Tyler's arms along so that she was fully stretched out on the bed as long as she could make herself.
“ Now Tyler, we have almost as much skin touching each other as it is possible to do. Can you suggest anything else?”
“ Yes ma'am. I can shove my dick in as far as it can reach.”
“ Do it.”
Tyler pushed his hips against hers, burying his cock as far as he could get, and held it there.
“ That's right Tyler. Now there is one thing left, one more place for us to touch.”
Tyler thought about it. They were touching from her hands above her head all the way down to their toes at the other end. And he was buried in her. What else could there be?
“ Where's that, ma'am?”
“ Our mouths Tyler, our mouths.”
Tyler pressed his head forward and kissed her, and felt her tongue eagerly melt against his. They were together in every way possible.
"Yesss oh yesss Tyler. Now can you feel how hard my nipples are? Think about that. You are against me with as much skin as humanly possible. You are feeling the breasts and making the nipples hard on a married woman. You are with someone else's wife, and you are all the way inside her with your hard dick and getting to fuck her for just three dollars. I want you to think about this. Just like that, within minutes of knowing you won the drawing, you are touching and feeling parts of me, not just on the outside but deep inside me too, that only one other man has ever known."
“ Yea...yes ma'am,. Thank you!”
She giggled. “Tyler, you are so cute. When my future husband and I started dating, he had to wait for several weeks just to feel my tits. That's was all he got to do when we were dating. After almost two years of dating and making out, he had wasted a lot of hard ons, and he came in my hand more than once, just like you did.
But Tyler, he never got to come on my naked belly. And he had to marry me before he got what you are getting. And then, and this is funny since it just happened to you, when I was ready to let him fuck me, he got all excited and came first. Then, unlike you, he couldn't get hard again until the next morning. So he had to wait, while you get to fuck me right away. See how lucky you are?"
Yes, ma'am. I'm the luckiest guy in the world." With that happy comment, Tyler relaxed all over his body as he suddenly gained confidence in his ability to please her. But again, she began to give instruction.
"Tyler, you lost almost all our contact. Now put your feet down next to mine again. Ahhh, yes. That's it, touch your toes against mine. That's it. Now shove your dick in as far as it can reach again. Yes, like that.”
Mary released his hands from hers and lowering her arms, placed her hands on his ass. “You can keep lying on me, I like being this close to you. Now your hands are free, so kiss me, squeeze my tits and keep kissing me while you pump."
“Oooh. Remember what I told you. Do it slow so I can feel every inch of your nice peter.”
Still acting as the student, Tyler raised his upper body just enough that he could reach between his body and hers and feel her tits. Then he began kissing her again, trying to put as much feeling into it as he could.
Mary began talking through lips that were locked together. "That's it. I want to be able to remember this moment forever, and I want you to remember it too. See how close together we are again? We are together from the end of your body to the end of mine, naked skin pressed against naked skin, and you are inside me, or...to put it another way, I am wrapped tightly around your penis. We are so close, nobody can get much closer than we are now, at least not physically."
She hugged him around the waist. “It's happening again! Think about what is happening. Feel our nipples almost touching. Feel our stomachs pressed together. I can even feel sweat forming between us. Can you feel it?”
“ Yes ma'am!”
“ Now run your mind further down. Go to the end and feel our toes touching, then go back up, up all the way to where your cock is inside my pussy. Think about it.”
She paused. "A nice part of your body, your most intimate flesh inside my most intimate flesh. Feels good, doesn't it"
"Oh God yes!"
"Just one thing left to achieve total closeness. We need to be kissing again while you fuck me good. I want this to be my best time, ever."
“ Yes ma'am, and this time I promise to keep going slow.”
This time his kissing was a little better. Learning from the way Mary had been repeatedly working him through this slowly, Tyler had calmed down some, and his penis, this time, could last.
"Mmmmmm." Mary was beginning to enjoy this a lot. Ignoring the toe contact now, she slowly began raising her legs, at first going up around his ass, and after a few more pumps, higher until her ass was almost off the bed. She wished now, that she had placed a pillow under her ass, but they were too involved now to have another interruption.
"Ooooh! So deep inside. Mmmmmm!" Mary's sounds of pleasure now were not being faked.
That did it. Her moans of pleasure as she began nearing orgasm sent Tyler over the top, and this time his hot cum ended up where it belonged, but too soon. Mary was disappointed as she felt his throbs. If she didn't get to cum, she at least wanted Tyler's first time to be memorable, and she wanted him to think that he was making her cum.
"Ooooh, I feel you coming. And me too! It's good, oh so very good." She squirmed her ass and pretended to be coming, and Tyler did not know the difference.
Tyler kept laying on her, even after his penis had dwindled. Since he had never heard a woman cum, Tyler did not know if her sounds had been the sounds of climaxing. In the midst of his intense pleasure while coming for the first time inside a woman, he had heard her say it, but was not sure of what he had heard. "Did you cum?"
"Of course," Mary lied. "You did just fine. Now pump some more so that you get it all out of you and into me."
He pumped and at the same time tried kissing her again. She returned his kiss, but not with as much enthusiasm as she had demonstrated before. Still, she made an effort. "Mmmm Tyler, I feel so wet inside. You really loaded me up."
"Yes ma'am."
Mary giggled. “I can feel your dick going soft now.”
'Yes ma'am.”
If she could have shook her head without Tyler seeing, she would have done so. Even now, after she had taken his cherry and trained him in how to fuck her, Tyler was still talking like a student does to his teacher.
Again Mary felt that she needed to re-assure him. “But your dick did the job Tyler. It managed to rise up there after coming once, and it lasted long enough for me to enjoy. I really liked feeling you coming inside me.”
“ And you too. It made you come.”
“Tyler it was you who made me come. Your cock is nice, but it was you that did it.” That might have been a mistake, because Mary felt his cock thicken inside her as he once again began to grow.
She patted him lightly on the ass. "No no Tyler, we've spent a lot of time at this and you are hard again, but I'm going to have to go to the bathroom and clean up, and I guess you had better get back to your buddies." Mary actually felt too tired to go to the bathroom, but she was using that as an excuse to get rid of Tyler now that he was used up.
Except of course Tyler was not 'used up' and Mary smiled and watched as Tyler wiped his erection dry after she had handed him a small hand towel. “Oh Tyler, you are soooo cute.” She grabbed onto his cock and wriggled it from side-to-side. I just love this cock of yours, but now you are going to have to stuff it in your pants and”..she giggled, “Be sure you don't catch it in your zipper.”
“Yes ma'am.”
As he was dressing, Mary remained in bed, slightly covered by a sheet, but allowing him to keep seeing her breasts. "If you want, you can tell your buddies that we did it twice. They don't need to know that you came in my hand and against my tummy."
He brightened. Tyler's pants were on, and he was buttoning up his shirt. "You won't tell on me?"
"Of course not. Besides, the conductor says you will be getting off early in the morning at Ft. Riley, and I won't see any of you again."
He showed his immaturity with his next question. "Is it alright if I tell them that I made you cum?"
She smiled. "That will be fine. You can tell them you made me cum twice and it was my best ever if you want to."
Tyler had a big grin on his face. Mary watched as he hurried to get dressed, and could tell that he was trying not to hurry as he hurried. “If you want, you can also tell them what my body was like, my breasts, and my pussy if you feel like it.”
“Really? You wouldn't mind?”
“No, not since you, they, won't be seeing me again. I saw and felt the way they all looked at me as I walked past them twice in the passenger car, and you, only you, know what I look like under my clothes. So you tell them because I am sure they want to know.”
She felt the train lurch and begin to slow. They were approaching St. Louis and the next stop. This entire affair had taken the full 30 minutes.
All dressed now and ready to start marching, Tyler looked almost sad. "Can I kiss you one last time?"
"Of course. And Tyler?"
"Yes ma'am?"
"I want you to know that I won't ever forget you either. I was your first, and you were my first other than my husband."
"Was I...O.K? Am I...big enough, and all that?"
He needed reassurance of his manhood. "Your..." she looked down at his crotch area, not wanting to say cock or penis, and nodded with her head. "You are a bit longer than my husband. Over an inch longer actually, and that's how much further into me you went then he can. And I liked how hard you get. It felt just fine."
He brightened, leaned forward and kissed her, but did it lightly, like he was afraid now that she might break. "Goodbye."
"Goodbye Tyler. And be careful if you go to war, please."
He straightened up and looked proud, soldier proud. "I plan to ma'am. Goodbye." He stood at attention, raised his right hand to his forehead, and saluted her. And with that, Tyler was gone.
Mary smiled to herself and and shook her head. She had not told Tyler the whole truth, that yes, he was longer than her husband, but not as thick.
Mary continued to lie in bed. Sheldon had indicated that she could stay in bed until daylight, and that was hours away. She sighed, then, holding her hand over her pussy so that Tyler's juice would not drain out onto the sheet, she crawled out of bed and grabbed a towel. Tyler had left quite a load, it seemed like, even after cumming first on her belly.
Mary's first strange fuck. She sat back on the bed with the towel pressed between her legs in case more cum drained out. Tyler had been very inexperienced, and of course Mary didn't have a lot more experience than he did herself. Tyler had started to feel pretty good once she had slowed him down and got him to start kissing again. 'Yes,' she thought, 'I would have climaxed with him if he had lasted a little bit longer. But that was only because he was new, strange, and therefore exciting. His penis didn't feel as good as Dave's. It was thinner and I couldn't feel it all that much once I got good and wet.'
The train had came to a stop in St. Louis, and remained for 15 minutes before it began rolling again. Mary stayed in bed because she did not want to risk walking down the corridors and seeing a soldier, maybe more than one and being looked at. 'They probably think I am a *****, and Sheldon is my pimp,' she was thinking. What she did not know was that Sheldon had told the soldiers that Mary was virtually innocent, riding a train for the first time, and needed money. Upon his saying that, every soldier in the car had put up money. Before that, there had been two or three holdouts thinking Mary was a *****.
Once the train was up to speed again, there came a knock on Mary's door. It was Sheldon, of course, and when she said 'Come in,' Sheldon used a pass key.
They smiled at one another, and then Sheldon reached into his pocket and pulled out a roll of five twenties. "I put all the one dollar bills in my briefcase cause I figure you wouldn't want to carry 100 one-dollar bills around."
"Thank you."
He looked strangely at her, and Mary, who was still lying in bed on her side, realized that she had failed to cover one breast. She reached to cover it, then realized that it was too late. Sheldon had already seen her tit, she knew it looked nice, so she allowed him to continue to see it.
Sheldon looked at her breast for a moment, then looked up into her face. "So, how did it go? You can tell me. I won't take anything you say back to them. Besides, they are bedding down until we pass through Kansas City, then I have to wake them up before we get to Ft. Riley. So they will be sleeping for a few hours."
"It was fun." She hesitated, "Different than my husband."
Sheldon smiled. He was hoping to get her to talk sex. He had time on his hands for a while, and there was no better way to spend it than talking to a pretty young lady like Mary. "How was he different?"
Mary picked up on it right away, the sexual tension in the roomette. Warning bells started going off, but she liked this man, and trusted him. Besides, Sheldon had already given her the money, and he had worked for the railroad for over 20 years he had said, so he must be 'safe.' After her dirty talk with Tyler, Mary was feeling a little freer to talk similar to Sheldon.
"He, well, his thing jumped right out of his underwear when he started to remove his shorts. He was ready it was obvious. But then he didn't know how to kiss, and I had to show him. Then he was afraid to touch me..." she looked down at her breast and touched it, 'here'. We were laying on our sides. Then, after I was holding him down there, his cock with my hand, I told him to feel my breast, and almost right away, he groaned and came all over my belly!"
Sheldon laughed, and Mary, after a few seconds, laughed with him. "Poor kid," Sheldon said. "Never had himself a real woman probably, and when he had one in his hands, he couldn't hold it." Sheldon laughed again.
Mary giggled, then said: "Actually, it's more than he never before had himself a real woman, he never before had a woman, period!"
"He was a virgin?"
"Yes, that's what he told me. Never did anything more than kissed girls at parties."
"So you took his 'cherry' with your hand. That's really great. He won't be forgetting you anytime soon."
"He won't, because after he wiped me clean with a towel, I let him try again."
"Oh, so then you took his cherry the real way."
"Yes, and I told him that since he was only my second man ever, that I wouldn't forget him either."
Sheldon frowned. "You've only had your husband, before tonight?"
"That's all."
"Damn! If I had known that, I might not have set you up to earn some money. The way you look so good, I figured you had been with more men than just one. I'm surprised that you didn't get mad."
Mary nodded. "I'm glad it happened. Besides the money, I learned some things."
"Like what?"
"Well, that men come in different sizes, and they do it in different ways, or don't know how to do it until you show them."
Sheldon picked right up on her 'different sizes' comment. This he wanted to hear more about. "What about the different sizes? How did the young soldier, Tyler, compare to your husband?" If Mary would answer that question, Sheldon was thinking that maybe he could get her to talk more about penis size, and maybe ask him about..his.
"He was longer than my husband, but it was thinner."
"Thinner? I'll bet it didn't feel as good then, as your husband's dick." There, Sheldon had used the word dick, so maybe she would get more detailed and descriptive. He had mentioned how dicks feel. Will she talk about it? Could she tell that her pussy was not being spread as far by a thinner dick?
Mary hesitated, then sighed. Tyler had not felt as good once he was in, that was true. But how did Sheldon know that? "You're right It didn't feel as good, but if he had lasted a little longer, he might have made me cum.".
"He came in you then, but you didn't get to cum?"
Her eyes met his. Mary knew now where this was leading. She gulped, then answered slowly, knowing full well that her answer would bring on a request, from Sheldon. "He came, I didn't, but I pretended to so that he would feel like a man his first time out. But I would have preferred to actually get to cum rather than faking it."
Mary suddenly felt herself getting hot, and wanted to throw off this sheet, but not just yet. Maybe, being a conductor, Sheldon couldn't do anything with her. The thought that Sheldon was much older, and black, was not in her thinking as far as deciding rather to do anything. Mary was horny, and Sheldon was making her more so.
She repeated her answer, wording it slightly different. "No. I didn't get to cum."
She continued to stare at Sheldon, and, moving her arm slightly, allowed the sheet to fall further, ******** her other breast. He had his answer and moved towards her. They kissed, this one much better and more masculine than the kisses she had been getting a while ago. Still, out of respect for her, Sheldon only touched her with his mouth, and then, after several seconds, with his hands, but only in innocent places.
"Do you have time? What about your job?"
"Between stations, late at night, I am basically free until about ten minutes before arrival at the next stop."
"How long is that?"
He checked his time piece, which he kept on a chain at his belt. "We still have to cross most of Missouri. About two hours."
"I'm waiting."
One again Mary found herself watching as a man undressed before her. Feeling really wet, and not sure if it was because of Sheldon or maybe some left over flow from Tyler, she pulled the sheet down, ******** her pubic hair. Then, grabbing a towel, she opened her legs, said, "Don't look," and wiped herself.
He was not only looking, but staring. "Are you all wet from me, or is that leftover soldier?" Then Sheldon laughed. "No, you used a rubber, so that wetness must be from me."
"No, it's not 'leftover soldier, it's because of you." She paused and thought a moment."Maybe it is 'leftover soldier. I decided not to use a rubber." She hesitated; "I'm about a month pregnant, so I didn't need to use one. I like doing it better without a rubber anyway."
Sheldon's eyes grew big. "Damn! I like that. I get to fuck you good, I get to fuck you long, and I don't have to wear no rubber!" He began undressing again.
As she watched him finishing his undressing, Mary was shocked at his use of the F word, but found that it had excited her. Yes, I am going to fuck another strange man, this time not for money, and he's a strange black man matter of fact, and...HE HAS A BIG COCK!'
Sheldon had just pulled his underwear down, and his penis, his 60-year-old penis, had suddenly popped right up there when he realized that he was soon going to be fucking the cutest and best built girl he had seen on his train in months, if not forever.
Mary gulped, said nothing, and stared. Sheldon sensed that she wanted a good look, and pretended not to notice as he continued to fold his uniform and hang it up. He turned sideways at the closet, and his pointing cock followed along. He had not felt this big and hard for a long time, and to go along with that, Sheldon planned to fuck Mary for a long time, maybe all the way to Kansas City.
"I guess I was right"
"How's that?"
Her voice was soft, almost a whisper. "Men do come in different sizes."
"You look scared. Don't be."
"I'm not scared. Well, maybe I am. Will you be gentle with me?"
"Of course. I've had my share of women, and know how to treat them."
"Am I...your first white woman?"
Sheldon hesitated, then answered truthfully. "White women don't come around to where I am when I'm not working. So I've never had a white woman off a train, but on one, I've had me a few."
"A few?"
"Maybe ten or so, over the years. But you're the finest!"
"And black women? How about those, on a train?"
Sheldon shrugged. "Not as many. Black women don't ride the train, long rides like this as much as white women. And if they do, they usually have their kids along."
"So I'm the finest, black or white?"
"Absolutely!"
She hoped that he was telling the truth about her being the finest. Mary reached out and touched his penis, then wrapped her trembling fingers around it as Sheldon stepped close to her. "Were you the biggest they had, all those white women?" Mary was thinking now, thinking about Sheldon being black, and wondering if that was the reason he was so big.
"I don't know for sure. The ones that talked about it, liked to talk, they all said I was the biggest."
"And the rest?" She was stroking him now, pulling on his foreskin, back and forth, up and over.
"They didn't say, but by the sounds they were making when I was putting it in, I think so."
"Hmmmm." Mary sounded like she was laughing when she had said that. "Did you make all of them cum?"
"I'm pretty sure about that. Took my time with all of them, and when they walked away, they could barely walk."
Mary laughed. "Braggart! But now you can add me to your list, as one of the ones that said you were the biggest, and maybe one of the ones you made cum."
Sheldon laughed and climbed onto the bed. Lying down beside her, he said, "First we have to get it in, then you can say I was your biggest."
"Yes, yes. Put it in. I want you to."
As Sheldon fondled her breasts prior to fucking her, he added: "And then after I get it in, you can say I made you cum."
"Mmmmmh! Awwwwww, shit." (pant pant) "Wait. Go slow! No, don't stop, just go....slow..."
"Lady, you have sharp fingernails!"
She was ready, she was wet, but it was a hard fit, and despite his wanting to be gentle, Mary had tears in her eyes. But she was a trooper and kept grabbing at his ass, urging him on, only slowly. Finally, after much gasping, groaning and other noises, with Sheldon hoping that no one was walking by and listening, he managed to bury it. He gave her a minute to adjust, and then began showing her what fucking was all about.
"Ooooooh oooooh! Mmmmmmm, Mmmmmm! Uuuuuuh Uuuuuuuh!:" Those were the sounds she was making, with just the first six strokes, the last two being harder and deeper. Then she became vocal, especially after Sheldon had picked up one of those little pillows and placed it under her ass.Her next sentence shocked him with the language she chose.
"Oh daddy, oh Sheldon, fuck me. FUCK ME!!"
Yes, Mary was loud, though until tonight, this part of the night, she had not known that she could be loud. Still, she did not cum until Sheldon began kissing her. He had concentrated on fitting his hugeness into her, staring down at her closed eyes, her opened mouth, looking so good, but he had allowed her room to breathe, and make noise before locking his lips over hers.
“Fuck baby, I need to come now!” Sheldon groaned, and Mary gasped as she felt his huge penis harden and begin pulsing as it spurted into her, his come going deep and hitting against the back of her cunt. She could feel it soaking her insides as he dropped the biggest load he had given a woman in years.
Her heart was pounding as he slowly came to a stop. For a moment, Mary thought that Sheldon might be having a heart attack, his breathing seemed so ragged.
“Sheldon,” she gasped! “Are you O.K?”
"Oh yeah baby. You just drained me, big time.”
She giggled and dug her fingers into his ass. “Can you do it again?”
“Baby, with you I can do it all night!”
“Let me get up and wipe first.” Mary had reached down and was feeling the cum that was oozing out all around the lips of her stretched pussy. In the process, her fingers were also feeling all around Sheldon's fat cock..
“No, leave it in. I plan to put some more on top of it, lot's more.”
“Well, then in that case, I need to clean my fingers.”
“Bring them up here.” When she did, Sheldon took hold of her hand and gently pushed her wet fingers into her mouth.
Mary was surprised, almost disgusted, but she managed to smile, and then as she tasted their combined juices, she sucked on her fingers until they were clean.
“Like that?”
“Mmmmm, yummy!”
From then on, it was one cum after another. And later, still more when Mary, feeling brave and experimental, climbed on top. More cums came into play.
"Damn! I've got to get ready, we're fifteen minutes from Kansas City." Time had flown, too quickly.
Just like that, two minutes later, Sheldon was gone as Mary lay in bed, with wondering eyes and feeling her pussy gently with two fingers of one hand to see if it was still in place, undamaged and still useable in the future. Never before had she been fucked like that. Not just the size, but in technique. Sheldon had also shown her how an older, experienced man could last, and last.
Almost asleep now, Mary began running her fingers over her pussy, feeling the come oozing out of her. She knew that she should get up and wipe, but she was too tired. Instead she began spreading the cum all around her lips, enjoying the feel of it as it coated her cunt. Her eyes closed and her fingers slowly came to a halt.
She slept through Kansas City, and yes, even Ft. Riley.
When she finally rose and had cleaned up she had to go back to the passenger car so that Sheldon could replace the bedding. When Sheldon went into the roomette, he smiled. Mary had pulled the sheets off and folded them neatly on the bed. He had to pull them apart because, if they totally dried with that cum all over them and got stuck together, they might not wash completely clean.
The sheets made a tearing sound as he pulled the dried portions apart. Then he realized that Mary had forgotten the pillow. Picking it up, he studied how the come they both had left had been smeared over almost the entire surface of the cover. That pillow case was evidence of how much fucking they had done with Mary's ass and legs high up as she groaned and cried out her pleasure under him.
Sheldon was replaced by another porter when the train reached Denver, but Sheldon managed to find a few moments to be alone with Mary, to hold her, and to kiss her before Sheldon left the train. In two hours he would be making a return trip. A week later, on the same train Mary was on, he would again be coming into Denver from Indianapolis.
"Will you remember me," Mary asked? I know that you've had other women on the train."
"Baby, you know I won't forget you. And when you return home, be sure to catch this same train. I'll be on it after you come up to Denver, and we can ride together all the way back to Indianapolis."
Mary laughed. "I'd like to say you could ride me all the way back to Indianapolis, but by then I will be too fat to fuck."
"Maybe. Remember that my dick is long and can reach way up in there. even if you have a big belly."
"Hee hee. That's true."
Another week after Mary had arrived in Long Beach, was living with her sister and working, she had a period. She had either missed a period, or was late. Shocked, Mary thought about all she had done, screwing Tyler without a rubber while thinking she was pregnant, then screwing, no, making love to Sheldon while thinking she was pregnant.
She resolved then and there to be good and wait for her husband. In the meantime, she had her memories.
Conducting Her Business
by EroticWriter
"All Aboarrrrrrrrrrrrddd!" The conductor’s deep voice rang out, loud enough to be heard even above the sounds of the hissing steam coming from the engine. The train station in Indianapolis was bustling, with trains on several tracks, all getting ready to go somewhere, something that was happening 24 hours a day now that the USA was at war.
Mary was already aboard, aided by the helping hand of the Pullman conductor as she had climbed the stairs, two bags of luggage in hand.
"Looks like this is your first time to ride a train," the white-haired black conductor commented.
"How did you know," Mary asked, her eyes bright with excitement?
"Oh, we can always tell miss. The way your eyes started taking it all in soon as you got on board. I can remember, wayyy back, my first train ride."
"Really? How old were you, and where were you headed?"
The conductor laughed. Mary already liked this man. This was the first time she had ever had a conversation with a black man, and she already felt completely relaxed with him.
"Let me help you with those bags while we find your seat, and then I'll tell you about my first ride." The conductor took both bags and lead Mary down a corridor past some sleeping compartments and stopped at the first seat forward of the last sleeping compartment they had passed. "I think you'll like sitting here miss, with the wall behind you. That way there's no one directly behind you to make you feel like you are being watched from behind."
"Would anyone be watching me," Mary beamed?
"Probably, miss. You're a very pretty young lady."
Mary giggled. "Tell me about your first train ride."
The conductor held out his hand. "In a minute. The name is Sheldon, miss. And what might yours be?"
"I'm Mary, and I am on my way to Long Beach, to go to work at the shipyard. My sister is there already and has an apartment we can share. So how about your first train ride?"
Sheldon laughed. "It wasn't actually a train ride. I was going to work, first day on the job and I had never been on a train before."
"Were you a conductor right off the bat?"
"Noooo ma'am. I worked as a busboy in the dining car. Then I became a porter. It took me 22 years to work up to where I am today." I spend more time on the train then I do at home."
Sheldon looked around. "Let me take care of some other passengers that might be needin' help, and then I'll come back and see how you are doing."
"That will be great. Thank you. It's nice to have someone to talk to."
Sheldon was off, and Mary had time to settle in. She had arrived a few minutes early, and the train was due to pull out in another ten minutes.
Mary looked up. Sheldon was back and looking down at her with a smile on his face. She brightened. "Oh, you're back already."
Sheldon nodded. "And I see by your ticket that you didn't buy a private sleeping compartment. That means you will be using one of our bunks with the curtain pulled.
"I know, but my money is kind of short. Sally, that's my sister, says that my pay will pretty good once I get to the ship yard, but that doesn't help me today."
Sheldon nodded. "We have some 'Roomettes' in the next car back." He lowered his voice. After it's dark, maybe I can let you slip into one for a few hours to catch some sleep. That way you will at least have a door you can lock instead of just a curtain. No one has to know."
"Really? You'd do that? That would be so nice."
"A roomette doesn't have a sink or a...toilet in it. All it is is a small compartment big enough for two to ride in, and the seat folds down across the room to sleep on. It has a small closet with hangers also. You will still have to go down the corridor to use a bath."
"Well, keep your eyes peeled for me. If no one is using a roomette, it would sure beat having to crawl in and sleep behind a curtain."
"Sheldon nodded. He checked his watch. "Mary, I'll be back later."
"Thank you."
Mary sighed as Sheldon walked off, heading down to greet some other passengers whom apparently had been late arrivals and were rushing down the aisle. Mary had been writing to her sister Sally for weeks now, and after Mary's husband Dave, who was in the Navy, had come home for 'shore leave' after two months of Navy Boot Camp and then gone off to his new assignment in the Pacific Fleet, Mary had decided to take Sally up on her invitation to work with her in Long Beach.
Sally had assured her: "When Dave comes home on shore leave, you will be close enough to San Diego to see him while he is in port. So working at the Long Beach yard would be real convenient for you."
Mary was assured a position as soon as she arrived since she had already had a year's experience working in an office, so her secretarial skills would come in handy. Her husband had completed his boot camp six weeks ago, came home from the Great Lakes Training Station, which was conveniently close to Indianapolis, and spent the better part of two weeks mostly in bed with Mary. Then he had taken the train to San Diego. Mary was following him by about three weeks, but would probably not see her husband until he came back into port. Since this was wartime, and Mary didn't even know where her husband's ship was headed due to secrecy, she might not see him for months, maybe years.
Dave had said that the scuttlebutt was that their ship was headed to 'Pearl' first, which meant Pearl Harbor in Hawaii, but that was just scuttlebutt and he could end up anywhere.
It was summer, 1943. America had been at war since December, 1941, and so far the news, after several months of bad, was looking good for the US forces in the Pacific. Japan was on the run, and American's Naval fleet had been rebuilt into a formidable fighting force, ready to conquer Japan in hopefully, just a few more months. "Win the war in '44' was the motto, and Mary could only hope that Dave's ship came through unscathed.
"You'll really enjoy it here, Sally had told Mary on the phone just yesterday after Mary had told her that she had purchased a train ticket and would be coming out. "There's a NCO club here, with lots of sailors to meet and dance with, and since they are all so lonely, you won't ever have to buy a meal, or a drink if you want one."
"Sally...why in the world would I want to dance or drink with other men? I'm happily married to Dave, remember?"
"I know. I didn't mean that you would actually DO anything with them. I just meant that it will be nice for me to have someone to accompany me when I go out, that way men won't be trying to pick up on me so much."
"I thought you told me that you hoped to meet someone...nice."
"I do, but all these guys are here for a few days or weeks, and then they are gone. And all they want to do while they are here is get laid."
"Sally! You haven't been doing...that, have you?"
"No, not really. But some of the guys I have met were pretty nice."
"Not really? What does that mean? Did you do it, with any one of them?"
"Well....."
"Sally?"
"Yes. But just one or two. It was no big thing."
Mary was shocked, but she should have known. Sally's 'one or two' was probably four or five. After all, Sally had been away from home for over a year now, and Mary had heard that things, that people were a 'lot wilder' in California. "Well, since you are no longer 'saving your virginity,' I hope that you are using 'protection."
"I carry them in my purse, just in case."
Mary was shaking her head, but of course on the phone Sally could not see her. "If I go anywhere with you, I expect you to be the perfect lady with me, O.K.? I'm married, faithful, and plan to stay that way."
"Sally had laughed. "Don't worry. When you are out with me I will be the perfect young lady, and you can keep me straight."
Mary nodded her head, and again Sally could not see. "Besides, Sally, I am pretty sure I am pregnant."
Silence. Then: "You think you are pregnant? How do you know?"
"Dave was here for two weeks, and spent the entire time in bed with me. I missed my period last week, so I'm pretty sure I got 'knocked up.'"
"What about your job, with me?"
"If I am pregnant, I will work until I get too big to work comfortably, then I will catch a train home to have the baby."
Sally sighed. "Well, that will work out I guess. But I was sure looking forward to having you around with me until the war ends."
"That won't be too long, Sally. I hear we will win the war in '44."
"I hope so." (Actually, the war in the Pacific would go on until September of 1945, but they didn't know it at the time).
That had ended their phone conversation, with Mary telling Sally when and at what time her train was supposed to arrive in Los Angeles, and Sally had told Mary that she could catch a 'red car' which was an electric trolley, from Union Station in Los Angeles all the way to Long Beach.
The train was rolling now, and had left Indianapolis way behind when Sheldon approached Mary, who, after staring out at the scenery for several minutes, had finally settled into reading a magazine.
"We'll be serving in the dining car starting in about 15 minutes." Sheldon looked at the watch on his wrist, "in exactly 14 minutes actually. So, when you are ready, just come forward two cars and take a seat. I've already told my co-workers there to take good care of you."
"Thank you Sheldon. That will be nice, and I'm starving."
"Our food is excellent. See you there."
The train was swaying, and since Mary had been seated the entire time the train had been rolling, she found it strange at first to get her balance and walk in a straight line. Fortunately the train had lots of handle type stuff to grab onto if need be.
Sherry had to open doors at the end of each car, and it was noisy going across the vestibule between cars. Even though the area was closed in, you could see out the sides of the floor and watch the earth moving past below you. It made you very aware that you were on a moving train, and right below your feet were two rails, going clickety clack in a steady rumble.
Mary came into the next car, and was surprised to see what looked like at least 40 soldiers, all young white males in uniform, and when she walked into the car, she heard someone seated beside where she was walking yell out: "Eyes center!" No one turned their head to stare, that would be too obvious. But she knew they were looking as she went past. All the seats in this section were facing forward, and each and every soldier could stare at her ass as she walked by. On the way back, they would be seeing her from the front, and be able to take in her face and tits, and all without turning a head.
Just like that, Mary found herself being stared at by 40 pairs of eyes as she walked past row after row of seated soldiers, all young, and all horny. Fortunately, they were respectful and not a word was said to her as she walked by, but Mary's face was red as she left that car and moved on forward to the dining car.
Her meal was excellent, just like the home-cooked meals she was used to, only better since at home they had to use ration books to make some food purchases, and there seemed to be no shortage of food in the dining car. And the two stewards, attractive young black men wearing white who served her were polite, and were perfection in motion as they served the passengers. Sheldon stopped by to see how she was doing, and Mary could not give enough praise to how good the food was and also the service.
She giggled. "I sure got a lot of stares though when I went through that last car. Every soldier in the place was looking at me it felt like."
"I am sure they were. Like I said, you are a very attractive young lady. I hope that none of them said anything they shouldn't have to you..."
"No. Just looking. I could feel my face burning time I got past."
Sheldon laughed. "You probably felt something else burning besides your face since they were all facing forward when you went past."
Mary was surprised at Sheldon's sexual innuendo, but took it in stride. "I said my face, but I could feel my backside crawling, maybe not burning, but I was aware of what they were looking at."
Sheldon nodded. "And you will have to run that gauntlet again on the way back, this time from the front. But I think I have some good news for you. I have a room you can use, a roomette with just a bed like I said, and it won't cost you anything. Just keep it to yourself." Sheldon had lowered his voice to show that they had to be 'confidential' about this.
"I understand. Thank you."
"I'll come back later and let you know the number of the roomette."
Mary again had to run the gauntlet, and this time, no one, well hardly no one, was obvious in staring at her since she could meet their eyes with hers if she wished. But she knew that they were staring, especially after she had gone past each aisle. She sensed that after seeing her face and chest, they were turning their heads this time since she was looking the other way, and again staring at her ass. Her ass was quite nice, and Mary deliberately let it sway, and she could feel every eye in the place on her rear as she went by. Face and tits front, ass and legs rear, and Mary had it all.
She half expected some soldiers to come back, looking for her, and did not know that they had been told to remain in the assigned car.
Clickety clack, clickety clack, click click clickety. Mary almost dozed off from the soothing sound of the steel wheels passing over the rails. .
Once it got dark, Mary was back in her seat with nothing behind her but a wall. This car was not fully occupied and she had some privacy. As Sheldon approached, he said, 'Move over."
Surprised, Mary moved over and Sheldon sat himself beside her, but not so close that his hips touched hers. "Mary. You said you were low on money. Could you use some to get set up when you get to Los Angeles?"
"Yes, of course." She giggled. "Do you have a job for me in the dining car, perhaps? Those two guys that were serving me were kind of cute."
Sheldon was pleased. If she had said that two black guys were cute, that was encouraging. "No, something different. The pay would be very good, and for just giving maybe an hour at the most of your time."
Mary didn't ask, so Sheldon went on. "I see that you are wearing a ring, so I assume that your are married, or maybe just wearing a ring so no one bothers you."
It sounded like he was asking in his last sentence, so Mary answered. "I'm married. My husband is sailing off somewhere with the Navy and I don't know when I will be seeing him again."
"I see. Do you plan...don't take this wrong, do you plan to stay 'faithful' to him all the time he is gone?"
"Well, yes, of course. That's what wives are supposed to do, isn't it? Especially military wives."
"Can I ask you something without you getting upset? It is a chance for you to earn some real money, and no one would ever know."
He was speaking very softly, and Mary leaned towards him and said, "Who do I have to kill?"
Sheldon smiled and went on. "All those soldiers that were looking at you, they were very impressed with what they were seeing."
Mary was beginning to catch on. "All those soldiers? If you are hinting at what I think you are, that's way too many men for me!" Mary laughed, like she was joking, because though it sounded like Sheldon was asking if she wanted to take all those soldiers to bed, she didn't really think so. It must be something else. And then Sheldon surprised her. What she had been thinking was true, except for the numbers.
"They all got together and came up with something. They just finished basic training at Ft Dix in New Jersey. They got paid, and haven't had a chance to spend any of it. So they all said they would put three dollars apiece into a pot, and whoever won the drawing would..."
Mary cut him off. "They want to do a drawing to see who would get to...sleep with me? Is that what you are saying?"
"It was their idea," Sheldon said defensively. I am just the messenger, offering you a chance to earn some real cash if you are interested."
Mary was silent for a while. Sheldon said, "Think about it while I make my rounds again, and then I'll be back."
Mary interrupted before he could leave. "And how much money are we talking about here?"
"There are 40 men, actually, to me they are just boys they are so young, and they all agreed to participate. So at three apiece, that comes to $120 and I would keep $20 for my efforts, arranging a place for it to happen, and changing the sheets afterward."
Mary for some reason found herself thinking it over, something she would never have dreamed in a million years that she would do. But she was low on funds, curious after hearing her sister admit to screwing around, and besides, now that Mary was pregnant, she was 'safe.'
"So my 'cut' would be $100, is that right? And for how long?"
"Yes, $100 and I would give it to you in advance. Time-wise, as long as it takes, one time, five minutes, or thirty, that would be up to you and whoever wins the drawing. But I could set a time limit if you like, and knock on your door after a certain time."
"But if I do this, then I would have to see them, all those men in the morning, and they would all look at me, and know what I had done. I don't think I could handle that."
"No ma'am. That would be no problem, because they are getting off when we stop at Ft Riley, Kansas. So when you get up in the morning, they won't be here."
"Will I be using a roomette? I remember you said they had no bathrooms in them."
"Yes, but there are towels in there, and I'll tell whoever wins to use the bath down the hall first if he needs to."
Mary hesitated, then..."I'll do it. Let me know what time, and show me which room."
"I'll go tell them to take up the money and have their drawing, then I'll come back and show you to your room."
As she waited, Mary was filled with excitement. A hundred dollars in those days, was a lot of money. And all she had to do was let some young soldier fuck her. Easier said than done, but she had decided that the money could go a long way in helping her get settled in California.
Ten minutes later Sheldon was back. "They're picking a winner. I don't think I've ever seen a group of men so excited before. Come on and we'll get you set up in a room." Sheldon led Mary down a corridor, into the next car, and taking out a key, said, "Here we are." He opened the door, and Mary entered a small but comfortable sitting area with a seat that faced front only. "Here is how we make up the bed."
Sheldon quickly pulled down the seat, making it into a bed in short order. He reached up into a compartment overhead and pulled out two sheets. Within one minute he had made up the bed, one sheet under, one on top, and had placed two small pillows in place. .
"You can see that there is not much room to move around on the floor once the bed is down, but you really don't need anything but the bed for what you are going to do." Put your suitcases under the bed for now, and if you have a purse, you can put it up there for safekeeping or if you don't feel safe about it, I can hold anything of value for you while the man is in your room."
"I trust you. Keep the hundred until after he has left and give it to me later."
"If you need to use the bath, it's the last door on the right. Get that over with while I go see who has won and I'll collect the money before I lead him back here. Will you be ready in say, ten minutes? If so, I'll knock on your door and let him in."
Mary gulped. "Should I be...naked when he comes in?"
He laughed. "Well, if you are, I can guarantee that I'll be getting a good look at you too." Then Sheldon took on a more serious tone. "I suggest maybe you should be wearing a nightgown." Sheldon reached into his pocket and pulled out a package, which Mary recognized to be a rubber. Then, thinking it over, Sheldon pulled out a second rubber and handed them both to her. "The second one is in case he breaks the first one with his fingernail or something."
"I'll probably put it on for him. I like doing that for my husband. What if he wants to use the second one to do it twice?"
"You are only committed to one time. Any more than that is your choice."
"It'll be just once, believe me. I just want the money."
Mary had not thought about rubbers. She had not placed one on her husband for those two weeks, and they had agreed that if she got pregnant, that would be fine. She was pregnant now and did not need a rubber, but did not tell Sheldon. Maybe she should have the guy put it on anyhow since right on the package it said 'for the prevention of disease.' Besides that, after doing it for her husband so many times in the past, Mary knew that rolling a rubber over and down a hard dick gave a woman a really good opportunity to handle and study the dick in detail.
If she was going to be having a strange dick, Mary wanted to know what it looked like since it might be the only one she ever has besides Dave.
"I'll be back with the winner in ten, maybe 15 minutes."
Sheldon left, and Mary immediately headed for the bathroom and took a pee, then washed her snatch thoroughly with a damp cloth. She looked at herself in a mirror, and spoke to it like it was her husband and he could hear. "Dave, you will never know what I am doing, but a hundred dollars is a lot of money and I can use it, and besides, I'm curious. I've never been with another man, and this is probably my one and only chance. If a baby is on the way, pretty soon I will be a mother, living back at home where my mother will be watching over me, and besides, in another couple of months I'll be too fat to fight as they say, or in my case it will be too fat to fuck."
Quickly, so she could be wearing her nightclothes, she rushed back to the roomette.
'Knock knock!" The sound startled Mary, though she had been expecting it. Slowly, her body shaking a little, she stepped off the bed down onto the floor and reached for the door handle. "Yes? Who is it?"
"It's the porter, miss."
Mary opened the door a crack, and seeing Sheldon and a young soldier behind him, she quickly opened the door and both men stepped in. Sheldon quickly closed the door behind him and said to Mary, "This is Tyler, the winner of the raffle. I told him to treat you with respect since you have never done this before and that he gets a reasonable amount of time to do the deed.”
He pulled out his pocket watch. “The train's next stop is St Louis in a little over 30 minutes so if you are still busy in here and the train starts slowing, don't let it concern you."
He looked directly at Mary, who was now dressed in a shortie nightie. "Are you O.K.?"
"Yes, I'll be fine, thank you." Smiling, Sheldon quickly took another admiring glance at Mary and left the room.
Mary had decided to wear something that until now only her husband had seen. In the process of looking sexy for Tyler, she had also been giving Sheldon a nice display of legs, and under the top half of her nightie, her nipples could clearly be seen outlined by the thin material.
"Hi."
"Hi, yourself," Mary replied. Tyler was tall, thin, and kind of nice-looking, in a country way. She looked at Tyler's uniform. "I guess you need to take that off." Upon seeing him, Mary had already decided that she wanted to fuck Tyler without his wearing a rubber. 'Skin to skin' is best, Dave had always said. Besides that, Mary was taking this one shot for fun, and in the case of Tyler, she wanted to feel his shot inside her.
"Yes, ma'am." As Tyler carefully removed his outer jacket and then the shirt under, he folded them neatly and put them precariously on a counter along one wall. Mary smiled. "There's a little closet over there with a few hangers you can use."
"Thank you." Mary crawled back up onto the bed, and in the process gave Tyler a brief peek at her inner thighs. She was wearing no panties, and Tyler caught just a quick glimpse of hair. His eyes grew wide as he sped up, struggling to get his T-shirt off, then bending down to remove his shoes before pulling off his trousers.
With them all hung on hangers, one thing remained. He looked at Mary, and she was watching. With his face red, he slowly undid his underwear, which was white with buttons all the way down the front. Before he could get all the buttons undone, his penis sprang out, sticking straight up and pointing at Mary."
"Oh! My! Looks like you are ready." This was only the second adult penis Mary had ever seen, and it was noticeably different than her husband's. This one had no foreskin, and was longer than Dave's by over an inch, but skinnier than Dave's penis both in the head and shaft. Also it was different in that it was straight as a ruler, while her husband's prick curved slightly to the left.
Tyler's face was bright red, and Mary could see it even in the dim light of the room. There was a bright overhead light, but Mary had left that one off. "Ma'am? I've never done anything like this."
"Is this your first time, with a woman?" Mary still had not gotten used to being a 'woman.' All her life she had been a girl, running with other girls. She and her friends still referred to themselves as girls.
"Yes, ma'am. All I've ever done is kiss girls at parties, stuff like that."
"Well Tyler, I'll tell you something that might make you feel better. This is the first time for me too."
He looked startled. "You...you're a virgin?"
Mary giggled. "No, I'm married, but my husband is away in the Navy, and I have never been with anyone else, so you will be a first for me too." She looked deliberately down at his dick. Look at how it is standing straight up. That's the hardest dick I've ever seen, but then, I have only seen two."
"Mine and your husband's?" Dave sounded encouraged, and that was something Mary wanted to do, was encourage him.
"Yes." She reached out and grasped it around the shaft. "It's as hard as a rock. Come on, get in bed with me."
Some kissing, awkward at first until Tyler got the feel of how Mary was using her tongue and began to imitate her. She was already holding his penis in her hand, but Tyler had one arm around her waist, and was lying on his other. Finally, after almost five minutes, Mary asked, "Don't you want to feel my breasts?"
"Oh, yes ma'am." Tyler reached out, touched her right breast, then cupped it, and as soon as he got a good feel, he immediately began climaxing against her belly. "Ooooooh!" His groan was loud and long.
He had said, 'Ooooooh,' and Mary said, "Oh oh!" as she felt blast after blast of hot cum landing on her stomach and running down sideways.
Silence. Mary was still holding his penis, which was for the most part still rigid, but she could feel his warm cum all over her stomach, above the belly button. "I...I got so excited, I couldn't control it. I guess I blew my chance."
Mary giggled. "No, not blew your chance. Our dick is still pretty hard, considering.” Tyler took note of the fact that Mary had referred to his dick as 'our dick,' and he was pleased.
Mary went on, “If you want, we can try again, but first you have to reach over there and grab one of those towels and wipe my stomach."
"I can do it again? Oh boy. Let me get a towel." Tyler sounded just like a little boy, which he basically was, fresh out of high school and into the Army.
Mary could have called it quits at this point, but she had become aroused. Tyler didn't know how to kiss, or how to fondle, and obviously he didn't know how to control his cock, but she had become aroused just the same.
Touching, and being touched by someone strange was having that effect on her. Actually, as she thought about it, knowing that someone was seeing her revealed was turning her on most of all. Mary had first noticed how being looked at had aroused her when Sheldon had stared at her in the nightie.
Now wiped dry, Mary was lying beside Tyler and stroking him. "Ready to put it in?"
"Don't I have to put on a rubber first?"
In answer, she moved her head forward and their lips met. Then two tongues intertwined. She giggled as she gripped his erection. "You get a special treat. No rubber needed because I am one almost month pregnant."
Tyler wasted no time. This was a dream come true. In seconds he was climbing over her and after a brief fumble struggle while he tried to find her hole and Mary ended up by holding and helping him, he was at her lips; Mary instinctively sensed that in his rush to penetrate her, that he would push himself into her too fast and spoil some of the fun.
Quickly, she pushed back against him, bringing his movement forward to a halt. “Do it slow so I can feel and enjoy every inch of that hard cock as it slides in.”
He was shaking, his entire body actually, but he managed to calm down a little as she continued to prevent his entry by pushing back on his cock that was still enclosed within her hand.
“ Yes ma'am.”
She waited another five seconds to be sure that he had regained control of his body, then released her hand.
“Now Tyler, give it to me slow, and kiss me while you do it.”
While she welcomed his warm tongue with one of her own, Mary had to aim his penis once again and smiled around their kiss as she felt his warm flesh part her lips and start in. He was spreading her, not as far as she might want, but it still felt good. Right in the middle of their kiss, she managed to speak. “Ooooh Tyler. That feels good.”
He was going perhaps a little too slow now. “Further Tyler, go on in.”
He pushed a little harder now, and Mary let out a soft 'Aaaaah' as she felt him penetrate. He continued in his slow march forward, stretching his way past her inner lips now and going deeper.
His entry was feeling good, but Mary had hoped for more since this was her first time. Mary was quite wet already, and he was not all that thick, but she wanted to help Tyler to feel like a man. Partially faking, she let out little gasps and then a groan at the appropriate times.
The taking in of his penis and making her groan was partially faking, but the pleasure she was feeling was not. Then, perhaps sooner than she would have liked, he bottomed out, going slightly deeper into her than her husband had ever gone.
"Uuuh Uuuh! Slow down and make it last." Tyler had begun banging away at her. In his lack of experience, he thought the way to please Mary was fast and hard, but she wanted slow, and romantic. "That's right, slow like that. Slow...and easy. That feels better. I learned from experience with my husband, and it felt the same with you.”
She moved her hands onto his ass. “When you do it fast, I can't feel all of your cock as good as I can when you go slow. Do it slow, yes, like that. I can feel every inch of your nice cock as it moves in and out There's no hurry, we can take our time."
"Yes ma'am."
"Now get up on your elbows and feel my breasts. I know you want to since you came as soon as you touched one a while ago."
Tyler almost hopped up onto his elbows and knees and began feeling her breasts, which filled his hands perfectly. Shaped like large apples, they were nice handfuls, and because of their shape, they made her dresses and shirts pop out like a well built bra, except that she did not need to wear a bra, but the times were not yet ripe for a woman to go topless under her clothes
For some reason, perhaps because of Tyler being a virgin, Mary was feeling very ornery and decided to talk dirty. In doing so, she began doing something she had never really done with Dave.
“ Stretch your legs down and put your feet up against mine. That's it, now we are toe-to-toe. Now lay your upper body down onto mine.”
“ But ma'am, won't I squash you?”
“ No Tyler, you're not that heavy. That's right, now we are getting closer. Now put your hands in mine.”
Tyler did, and as their hands locked together, Mary raised her arms out above her head and pulled Tyler's arms along so that she was fully stretched out on the bed as long as she could make herself.
“ Now Tyler, we have almost as much skin touching each other as it is possible to do. Can you suggest anything else?”
“ Yes ma'am. I can shove my dick in as far as it can reach.”
“ Do it.”
Tyler pushed his hips against hers, burying his cock as far as he could get, and held it there.
“ That's right Tyler. Now there is one thing left, one more place for us to touch.”
Tyler thought about it. They were touching from her hands above her head all the way down to their toes at the other end. And he was buried in her. What else could there be?
“ Where's that, ma'am?”
“ Our mouths Tyler, our mouths.”
Tyler pressed his head forward and kissed her, and felt her tongue eagerly melt against his. They were together in every way possible.
"Yesss oh yesss Tyler. Now can you feel how hard my nipples are? Think about that. You are against me with as much skin as humanly possible. You are feeling the breasts and making the nipples hard on a married woman. You are with someone else's wife, and you are all the way inside her with your hard dick and getting to fuck her for just three dollars. I want you to think about this. Just like that, within minutes of knowing you won the drawing, you are touching and feeling parts of me, not just on the outside but deep inside me too, that only one other man has ever known."
“ Yea...yes ma'am,. Thank you!”
She giggled. “Tyler, you are so cute. When my future husband and I started dating, he had to wait for several weeks just to feel my tits. That's was all he got to do when we were dating. After almost two years of dating and making out, he had wasted a lot of hard ons, and he came in my hand more than once, just like you did.
But Tyler, he never got to come on my naked belly. And he had to marry me before he got what you are getting. And then, and this is funny since it just happened to you, when I was ready to let him fuck me, he got all excited and came first. Then, unlike you, he couldn't get hard again until the next morning. So he had to wait, while you get to fuck me right away. See how lucky you are?"
Yes, ma'am. I'm the luckiest guy in the world." With that happy comment, Tyler relaxed all over his body as he suddenly gained confidence in his ability to please her. But again, she began to give instruction.
"Tyler, you lost almost all our contact. Now put your feet down next to mine again. Ahhh, yes. That's it, touch your toes against mine. That's it. Now shove your dick in as far as it can reach again. Yes, like that.”
Mary released his hands from hers and lowering her arms, placed her hands on his ass. “You can keep lying on me, I like being this close to you. Now your hands are free, so kiss me, squeeze my tits and keep kissing me while you pump."
“Oooh. Remember what I told you. Do it slow so I can feel every inch of your nice peter.”
Still acting as the student, Tyler raised his upper body just enough that he could reach between his body and hers and feel her tits. Then he began kissing her again, trying to put as much feeling into it as he could.
Mary began talking through lips that were locked together. "That's it. I want to be able to remember this moment forever, and I want you to remember it too. See how close together we are again? We are together from the end of your body to the end of mine, naked skin pressed against naked skin, and you are inside me, or...to put it another way, I am wrapped tightly around your penis. We are so close, nobody can get much closer than we are now, at least not physically."
She hugged him around the waist. “It's happening again! Think about what is happening. Feel our nipples almost touching. Feel our stomachs pressed together. I can even feel sweat forming between us. Can you feel it?”
“ Yes ma'am!”
“ Now run your mind further down. Go to the end and feel our toes touching, then go back up, up all the way to where your cock is inside my pussy. Think about it.”
She paused. "A nice part of your body, your most intimate flesh inside my most intimate flesh. Feels good, doesn't it"
"Oh God yes!"
"Just one thing left to achieve total closeness. We need to be kissing again while you fuck me good. I want this to be my best time, ever."
“ Yes ma'am, and this time I promise to keep going slow.”
This time his kissing was a little better. Learning from the way Mary had been repeatedly working him through this slowly, Tyler had calmed down some, and his penis, this time, could last.
"Mmmmmm." Mary was beginning to enjoy this a lot. Ignoring the toe contact now, she slowly began raising her legs, at first going up around his ass, and after a few more pumps, higher until her ass was almost off the bed. She wished now, that she had placed a pillow under her ass, but they were too involved now to have another interruption.
"Ooooh! So deep inside. Mmmmmm!" Mary's sounds of pleasure now were not being faked.
That did it. Her moans of pleasure as she began nearing orgasm sent Tyler over the top, and this time his hot cum ended up where it belonged, but too soon. Mary was disappointed as she felt his throbs. If she didn't get to cum, she at least wanted Tyler's first time to be memorable, and she wanted him to think that he was making her cum.
"Ooooh, I feel you coming. And me too! It's good, oh so very good." She squirmed her ass and pretended to be coming, and Tyler did not know the difference.
Tyler kept laying on her, even after his penis had dwindled. Since he had never heard a woman cum, Tyler did not know if her sounds had been the sounds of climaxing. In the midst of his intense pleasure while coming for the first time inside a woman, he had heard her say it, but was not sure of what he had heard. "Did you cum?"
"Of course," Mary lied. "You did just fine. Now pump some more so that you get it all out of you and into me."
He pumped and at the same time tried kissing her again. She returned his kiss, but not with as much enthusiasm as she had demonstrated before. Still, she made an effort. "Mmmm Tyler, I feel so wet inside. You really loaded me up."
"Yes ma'am."
Mary giggled. “I can feel your dick going soft now.”
'Yes ma'am.”
If she could have shook her head without Tyler seeing, she would have done so. Even now, after she had taken his cherry and trained him in how to fuck her, Tyler was still talking like a student does to his teacher.
Again Mary felt that she needed to re-assure him. “But your dick did the job Tyler. It managed to rise up there after coming once, and it lasted long enough for me to enjoy. I really liked feeling you coming inside me.”
“ And you too. It made you come.”
“Tyler it was you who made me come. Your cock is nice, but it was you that did it.” That might have been a mistake, because Mary felt his cock thicken inside her as he once again began to grow.
She patted him lightly on the ass. "No no Tyler, we've spent a lot of time at this and you are hard again, but I'm going to have to go to the bathroom and clean up, and I guess you had better get back to your buddies." Mary actually felt too tired to go to the bathroom, but she was using that as an excuse to get rid of Tyler now that he was used up.
Except of course Tyler was not 'used up' and Mary smiled and watched as Tyler wiped his erection dry after she had handed him a small hand towel. “Oh Tyler, you are soooo cute.” She grabbed onto his cock and wriggled it from side-to-side. I just love this cock of yours, but now you are going to have to stuff it in your pants and”..she giggled, “Be sure you don't catch it in your zipper.”
“Yes ma'am.”
As he was dressing, Mary remained in bed, slightly covered by a sheet, but allowing him to keep seeing her breasts. "If you want, you can tell your buddies that we did it twice. They don't need to know that you came in my hand and against my tummy."
He brightened. Tyler's pants were on, and he was buttoning up his shirt. "You won't tell on me?"
"Of course not. Besides, the conductor says you will be getting off early in the morning at Ft. Riley, and I won't see any of you again."
He showed his immaturity with his next question. "Is it alright if I tell them that I made you cum?"
She smiled. "That will be fine. You can tell them you made me cum twice and it was my best ever if you want to."
Tyler had a big grin on his face. Mary watched as he hurried to get dressed, and could tell that he was trying not to hurry as he hurried. “If you want, you can also tell them what my body was like, my breasts, and my pussy if you feel like it.”
“Really? You wouldn't mind?”
“No, not since you, they, won't be seeing me again. I saw and felt the way they all looked at me as I walked past them twice in the passenger car, and you, only you, know what I look like under my clothes. So you tell them because I am sure they want to know.”
She felt the train lurch and begin to slow. They were approaching St. Louis and the next stop. This entire affair had taken the full 30 minutes.
All dressed now and ready to start marching, Tyler looked almost sad. "Can I kiss you one last time?"
"Of course. And Tyler?"
"Yes ma'am?"
"I want you to know that I won't ever forget you either. I was your first, and you were my first other than my husband."
"Was I...O.K? Am I...big enough, and all that?"
He needed reassurance of his manhood. "Your..." she looked down at his crotch area, not wanting to say cock or penis, and nodded with her head. "You are a bit longer than my husband. Over an inch longer actually, and that's how much further into me you went then he can. And I liked how hard you get. It felt just fine."
He brightened, leaned forward and kissed her, but did it lightly, like he was afraid now that she might break. "Goodbye."
"Goodbye Tyler. And be careful if you go to war, please."
He straightened up and looked proud, soldier proud. "I plan to ma'am. Goodbye." He stood at attention, raised his right hand to his forehead, and saluted her. And with that, Tyler was gone.
Mary smiled to herself and and shook her head. She had not told Tyler the whole truth, that yes, he was longer than her husband, but not as thick.
Mary continued to lie in bed. Sheldon had indicated that she could stay in bed until daylight, and that was hours away. She sighed, then, holding her hand over her pussy so that Tyler's juice would not drain out onto the sheet, she crawled out of bed and grabbed a towel. Tyler had left quite a load, it seemed like, even after cumming first on her belly.
Mary's first strange fuck. She sat back on the bed with the towel pressed between her legs in case more cum drained out. Tyler had been very inexperienced, and of course Mary didn't have a lot more experience than he did herself. Tyler had started to feel pretty good once she had slowed him down and got him to start kissing again. 'Yes,' she thought, 'I would have climaxed with him if he had lasted a little bit longer. But that was only because he was new, strange, and therefore exciting. His penis didn't feel as good as Dave's. It was thinner and I couldn't feel it all that much once I got good and wet.'
The train had came to a stop in St. Louis, and remained for 15 minutes before it began rolling again. Mary stayed in bed because she did not want to risk walking down the corridors and seeing a soldier, maybe more than one and being looked at. 'They probably think I am a *****, and Sheldon is my pimp,' she was thinking. What she did not know was that Sheldon had told the soldiers that Mary was virtually innocent, riding a train for the first time, and needed money. Upon his saying that, every soldier in the car had put up money. Before that, there had been two or three holdouts thinking Mary was a *****.
Once the train was up to speed again, there came a knock on Mary's door. It was Sheldon, of course, and when she said 'Come in,' Sheldon used a pass key.
They smiled at one another, and then Sheldon reached into his pocket and pulled out a roll of five twenties. "I put all the one dollar bills in my briefcase cause I figure you wouldn't want to carry 100 one-dollar bills around."
"Thank you."
He looked strangely at her, and Mary, who was still lying in bed on her side, realized that she had failed to cover one breast. She reached to cover it, then realized that it was too late. Sheldon had already seen her tit, she knew it looked nice, so she allowed him to continue to see it.
Sheldon looked at her breast for a moment, then looked up into her face. "So, how did it go? You can tell me. I won't take anything you say back to them. Besides, they are bedding down until we pass through Kansas City, then I have to wake them up before we get to Ft. Riley. So they will be sleeping for a few hours."
"It was fun." She hesitated, "Different than my husband."
Sheldon smiled. He was hoping to get her to talk sex. He had time on his hands for a while, and there was no better way to spend it than talking to a pretty young lady like Mary. "How was he different?"
Mary picked up on it right away, the sexual tension in the roomette. Warning bells started going off, but she liked this man, and trusted him. Besides, Sheldon had already given her the money, and he had worked for the railroad for over 20 years he had said, so he must be 'safe.' After her dirty talk with Tyler, Mary was feeling a little freer to talk similar to Sheldon.
"He, well, his thing jumped right out of his underwear when he started to remove his shorts. He was ready it was obvious. But then he didn't know how to kiss, and I had to show him. Then he was afraid to touch me..." she looked down at her breast and touched it, 'here'. We were laying on our sides. Then, after I was holding him down there, his cock with my hand, I told him to feel my breast, and almost right away, he groaned and came all over my belly!"
Sheldon laughed, and Mary, after a few seconds, laughed with him. "Poor kid," Sheldon said. "Never had himself a real woman probably, and when he had one in his hands, he couldn't hold it." Sheldon laughed again.
Mary giggled, then said: "Actually, it's more than he never before had himself a real woman, he never before had a woman, period!"
"He was a virgin?"
"Yes, that's what he told me. Never did anything more than kissed girls at parties."
"So you took his 'cherry' with your hand. That's really great. He won't be forgetting you anytime soon."
"He won't, because after he wiped me clean with a towel, I let him try again."
"Oh, so then you took his cherry the real way."
"Yes, and I told him that since he was only my second man ever, that I wouldn't forget him either."
Sheldon frowned. "You've only had your husband, before tonight?"
"That's all."
"Damn! If I had known that, I might not have set you up to earn some money. The way you look so good, I figured you had been with more men than just one. I'm surprised that you didn't get mad."
Mary nodded. "I'm glad it happened. Besides the money, I learned some things."
"Like what?"
"Well, that men come in different sizes, and they do it in different ways, or don't know how to do it until you show them."
Sheldon picked right up on her 'different sizes' comment. This he wanted to hear more about. "What about the different sizes? How did the young soldier, Tyler, compare to your husband?" If Mary would answer that question, Sheldon was thinking that maybe he could get her to talk more about penis size, and maybe ask him about..his.
"He was longer than my husband, but it was thinner."
"Thinner? I'll bet it didn't feel as good then, as your husband's dick." There, Sheldon had used the word dick, so maybe she would get more detailed and descriptive. He had mentioned how dicks feel. Will she talk about it? Could she tell that her pussy was not being spread as far by a thinner dick?
Mary hesitated, then sighed. Tyler had not felt as good once he was in, that was true. But how did Sheldon know that? "You're right It didn't feel as good, but if he had lasted a little longer, he might have made me cum.".
"He came in you then, but you didn't get to cum?"
Her eyes met his. Mary knew now where this was leading. She gulped, then answered slowly, knowing full well that her answer would bring on a request, from Sheldon. "He came, I didn't, but I pretended to so that he would feel like a man his first time out. But I would have preferred to actually get to cum rather than faking it."
Mary suddenly felt herself getting hot, and wanted to throw off this sheet, but not just yet. Maybe, being a conductor, Sheldon couldn't do anything with her. The thought that Sheldon was much older, and black, was not in her thinking as far as deciding rather to do anything. Mary was horny, and Sheldon was making her more so.
She repeated her answer, wording it slightly different. "No. I didn't get to cum."
She continued to stare at Sheldon, and, moving her arm slightly, allowed the sheet to fall further, ******** her other breast. He had his answer and moved towards her. They kissed, this one much better and more masculine than the kisses she had been getting a while ago. Still, out of respect for her, Sheldon only touched her with his mouth, and then, after several seconds, with his hands, but only in innocent places.
"Do you have time? What about your job?"
"Between stations, late at night, I am basically free until about ten minutes before arrival at the next stop."
"How long is that?"
He checked his time piece, which he kept on a chain at his belt. "We still have to cross most of Missouri. About two hours."
"I'm waiting."
One again Mary found herself watching as a man undressed before her. Feeling really wet, and not sure if it was because of Sheldon or maybe some left over flow from Tyler, she pulled the sheet down, ******** her pubic hair. Then, grabbing a towel, she opened her legs, said, "Don't look," and wiped herself.
He was not only looking, but staring. "Are you all wet from me, or is that leftover soldier?" Then Sheldon laughed. "No, you used a rubber, so that wetness must be from me."
"No, it's not 'leftover soldier, it's because of you." She paused and thought a moment."Maybe it is 'leftover soldier. I decided not to use a rubber." She hesitated; "I'm about a month pregnant, so I didn't need to use one. I like doing it better without a rubber anyway."
Sheldon's eyes grew big. "Damn! I like that. I get to fuck you good, I get to fuck you long, and I don't have to wear no rubber!" He began undressing again.
As she watched him finishing his undressing, Mary was shocked at his use of the F word, but found that it had excited her. Yes, I am going to fuck another strange man, this time not for money, and he's a strange black man matter of fact, and...HE HAS A BIG COCK!'
Sheldon had just pulled his underwear down, and his penis, his 60-year-old penis, had suddenly popped right up there when he realized that he was soon going to be fucking the cutest and best built girl he had seen on his train in months, if not forever.
Mary gulped, said nothing, and stared. Sheldon sensed that she wanted a good look, and pretended not to notice as he continued to fold his uniform and hang it up. He turned sideways at the closet, and his pointing cock followed along. He had not felt this big and hard for a long time, and to go along with that, Sheldon planned to fuck Mary for a long time, maybe all the way to Kansas City.
"I guess I was right"
"How's that?"
Her voice was soft, almost a whisper. "Men do come in different sizes."
"You look scared. Don't be."
"I'm not scared. Well, maybe I am. Will you be gentle with me?"
"Of course. I've had my share of women, and know how to treat them."
"Am I...your first white woman?"
Sheldon hesitated, then answered truthfully. "White women don't come around to where I am when I'm not working. So I've never had a white woman off a train, but on one, I've had me a few."
"A few?"
"Maybe ten or so, over the years. But you're the finest!"
"And black women? How about those, on a train?"
Sheldon shrugged. "Not as many. Black women don't ride the train, long rides like this as much as white women. And if they do, they usually have their kids along."
"So I'm the finest, black or white?"
"Absolutely!"
She hoped that he was telling the truth about her being the finest. Mary reached out and touched his penis, then wrapped her trembling fingers around it as Sheldon stepped close to her. "Were you the biggest they had, all those white women?" Mary was thinking now, thinking about Sheldon being black, and wondering if that was the reason he was so big.
"I don't know for sure. The ones that talked about it, liked to talk, they all said I was the biggest."
"And the rest?" She was stroking him now, pulling on his foreskin, back and forth, up and over.
"They didn't say, but by the sounds they were making when I was putting it in, I think so."
"Hmmmm." Mary sounded like she was laughing when she had said that. "Did you make all of them cum?"
"I'm pretty sure about that. Took my time with all of them, and when they walked away, they could barely walk."
Mary laughed. "Braggart! But now you can add me to your list, as one of the ones that said you were the biggest, and maybe one of the ones you made cum."
Sheldon laughed and climbed onto the bed. Lying down beside her, he said, "First we have to get it in, then you can say I was your biggest."
"Yes, yes. Put it in. I want you to."
As Sheldon fondled her breasts prior to fucking her, he added: "And then after I get it in, you can say I made you cum."
"Mmmmmh! Awwwwww, shit." (pant pant) "Wait. Go slow! No, don't stop, just go....slow..."
"Lady, you have sharp fingernails!"
She was ready, she was wet, but it was a hard fit, and despite his wanting to be gentle, Mary had tears in her eyes. But she was a trooper and kept grabbing at his ass, urging him on, only slowly. Finally, after much gasping, groaning and other noises, with Sheldon hoping that no one was walking by and listening, he managed to bury it. He gave her a minute to adjust, and then began showing her what fucking was all about.
"Ooooooh oooooh! Mmmmmmm, Mmmmmm! Uuuuuuh Uuuuuuuh!:" Those were the sounds she was making, with just the first six strokes, the last two being harder and deeper. Then she became vocal, especially after Sheldon had picked up one of those little pillows and placed it under her ass.Her next sentence shocked him with the language she chose.
"Oh daddy, oh Sheldon, fuck me. FUCK ME!!"
Yes, Mary was loud, though until tonight, this part of the night, she had not known that she could be loud. Still, she did not cum until Sheldon began kissing her. He had concentrated on fitting his hugeness into her, staring down at her closed eyes, her opened mouth, looking so good, but he had allowed her room to breathe, and make noise before locking his lips over hers.
“Fuck baby, I need to come now!” Sheldon groaned, and Mary gasped as she felt his huge penis harden and begin pulsing as it spurted into her, his come going deep and hitting against the back of her cunt. She could feel it soaking her insides as he dropped the biggest load he had given a woman in years.
Her heart was pounding as he slowly came to a stop. For a moment, Mary thought that Sheldon might be having a heart attack, his breathing seemed so ragged.
“Sheldon,” she gasped! “Are you O.K?”
"Oh yeah baby. You just drained me, big time.”
She giggled and dug her fingers into his ass. “Can you do it again?”
“Baby, with you I can do it all night!”
“Let me get up and wipe first.” Mary had reached down and was feeling the cum that was oozing out all around the lips of her stretched pussy. In the process, her fingers were also feeling all around Sheldon's fat cock..
“No, leave it in. I plan to put some more on top of it, lot's more.”
“Well, then in that case, I need to clean my fingers.”
“Bring them up here.” When she did, Sheldon took hold of her hand and gently pushed her wet fingers into her mouth.
Mary was surprised, almost disgusted, but she managed to smile, and then as she tasted their combined juices, she sucked on her fingers until they were clean.
“Like that?”
“Mmmmm, yummy!”
From then on, it was one cum after another. And later, still more when Mary, feeling brave and experimental, climbed on top. More cums came into play.
"Damn! I've got to get ready, we're fifteen minutes from Kansas City." Time had flown, too quickly.
Just like that, two minutes later, Sheldon was gone as Mary lay in bed, with wondering eyes and feeling her pussy gently with two fingers of one hand to see if it was still in place, undamaged and still useable in the future. Never before had she been fucked like that. Not just the size, but in technique. Sheldon had also shown her how an older, experienced man could last, and last.
Almost asleep now, Mary began running her fingers over her pussy, feeling the come oozing out of her. She knew that she should get up and wipe, but she was too tired. Instead she began spreading the cum all around her lips, enjoying the feel of it as it coated her cunt. Her eyes closed and her fingers slowly came to a halt.
She slept through Kansas City, and yes, even Ft. Riley.
When she finally rose and had cleaned up she had to go back to the passenger car so that Sheldon could replace the bedding. When Sheldon went into the roomette, he smiled. Mary had pulled the sheets off and folded them neatly on the bed. He had to pull them apart because, if they totally dried with that cum all over them and got stuck together, they might not wash completely clean.
The sheets made a tearing sound as he pulled the dried portions apart. Then he realized that Mary had forgotten the pillow. Picking it up, he studied how the come they both had left had been smeared over almost the entire surface of the cover. That pillow case was evidence of how much fucking they had done with Mary's ass and legs high up as she groaned and cried out her pleasure under him.
Sheldon was replaced by another porter when the train reached Denver, but Sheldon managed to find a few moments to be alone with Mary, to hold her, and to kiss her before Sheldon left the train. In two hours he would be making a return trip. A week later, on the same train Mary was on, he would again be coming into Denver from Indianapolis.
"Will you remember me," Mary asked? I know that you've had other women on the train."
"Baby, you know I won't forget you. And when you return home, be sure to catch this same train. I'll be on it after you come up to Denver, and we can ride together all the way back to Indianapolis."
Mary laughed. "I'd like to say you could ride me all the way back to Indianapolis, but by then I will be too fat to fuck."
"Maybe. Remember that my dick is long and can reach way up in there. even if you have a big belly."
"Hee hee. That's true."
Another week after Mary had arrived in Long Beach, was living with her sister and working, she had a period. She had either missed a period, or was late. Shocked, Mary thought about all she had done, screwing Tyler without a rubber while thinking she was pregnant, then screwing, no, making love to Sheldon while thinking she was pregnant.
She resolved then and there to be good and wait for her husband. In the meantime, she had her memories.
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