Big Takes on a New Meaning For Sherry
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Written by EroticWriter / Jun 29, 2010
It was her first time at being a ******. Sherry thought her husband's cock was the biggest! That is, until tonight she had thought that. This customer's penis Sherry is holding in her hand is much larger than average. Sherry fondles it for a minute while checking out the length and the thickness. Also, this penis is uncircumcised, the first uncut penis Sherry has seen.
When she pulls on the foreskin, Sherry marvels and makes comments about how his foreskin moves up and down, first covering and then uncovering his cock head. The skin makes it much easier to stroke up and down than when she does it for Harry.
Sherry wraps two hands around it end to end, and discovers that even though she has two hands on him end to end, he still has the entire head, a sizable knob, left over. After maybe 60 seconds of exploration and admiring his penis, Sherry begins her hand job.
The John can tell that Sherry is excited. Figuring he can con her into giving him a blowjob and maybe some free pussy, he says, "I really wish that I had a hundred dollars or more on me instead of just thirty. If I had more money I could see how you would feel with your mouth and then your pussy wrapped around my dick."
Sherry replies sadly that yes it is too bad, because she wants to make some money as soon as possible. Unsaid are her desires for this man and his body.
The customer raises his hips and pulls his pants down around his calves so that he can spread his legs and let Sherry have a better look at his penis and also see his balls, which are a goodly size as well. Thrusting his dick even higher as Sherry takes a feel of his balls and continues to stroke his cock with the other hand, he asks, "Do you give free samples of your blowjobs? If you do and I like it, I could order some more the next time I see you."
Sherry wants to be a good businesswoman and please her customers. She says, "Well, just a little sample might be alright." With that Sherry lowers her head and opens her mouth wide. She pulls his foreskin down and slips her mouth down over his dick. Because it is so wide it is difficult to envelop his head but Sherry somehow manages. As her lips close down around the bottom of the head, her tongue begins twirling expertly around and around. At the same time she begins slowly jacking. He sighs and she pauses. "Is that the way you like it," she asks?
"Oh yes," he begins, then, remembering that this is supposed to be a "sample," he adds; "but I need a minute more to be sure." Sherry resumes her activity.
Within a minute the customer is getting ever closer to coming. He is thinking that he could just let it go now in her mouth and have what would basically be a free and complete blowjob, or maybe one for thirty dollars. But as much as he loves blowjobs, this gal is brand new at hooking and so lovely that he just has to have her all the way. 'Yes," he decides, 'I really want to fuck this woman. I want to slip my big meat into her and feel how tight and wet she is. I want her to get excited and wrap her arms and legs around me so that I can make her come, come, and come again.
He is about to tell her to stop when Sherry begins sucking and jacking him even harder. He is losing control. "Wait, wait, I'm going to come!"
Too late, Sherry stops jacking and removes her mouth. When his penis suddenly spurts a load high into the air, he yells, "Catch it with your mouth, quick, before it gets on my seat!"
Sherry is already ahead of him. When she saw that first blob spring forth, she was already aiming with her mouth. Magically, with skill born of experience from her sessions with Harry, Sherry catches almost the entire first shot into her mouth. Sherry immediately goes down on him again and while he is groaning with pleasure she masturbates him while working hard with her lips and tongue so that he delivers all he has left to give.
Fortunately for Sherry, she likes swallowing a good hot load and his load is not only hot but it is substantial in quantity. Even after he has gone limp she continues to suck and holds his penis in one hand while the other cradles his balls.
He was very pleasantly surprised when he realized that she was actually swallowing what he had to offer in liquid form. When Sherry has finished milking his load he looks sheepish and says, "Wow, I'm really sorry about that. You are so good at sucking that my orgasm snuck up on me. I tried to warn you but you didn't stop quickly enough. All I wanted was a sample of how good you are at blowjobs and then I wanted to put it in and feel your pussy for a little bit."
Sherry says apologetically, Well, I'm just learning how so I guess it was my fault for not stopping soon enough." She looked into his eyes; "Do you still want to sample my pussy?"
"Oh yes. That's the most important thing. If that's good, I will be back for sure, maybe more than once." Sherry gave his partially soft penis a squeeze and giggled. "I can get you hard again if you want so that you can sample my pussy."
He can't believe his ears. "Yes, yes, go ahead. I promise, if you are good I'll come back real soon and buy some from you."
With that Sherry begins blowing him again. More cum oozes out of his rod and Sherry swallows. In only a minute he is rigid. "Wow, you are really good at sucking cock," he says, "but now I want to see how your pussy feels." With that, Sherry raises her hips, lifts her skirt and pulls her panties down and off her legs. Then, leaning back against the seat, she opens her legs wide.
The customer can't believe his good fortune as he stares open-mouthed at her nakedness. She is wearing a white garter belt. How sexy. And what a nice looking snatch she has. Sherry not only is gorgeous, she is a true blonde. He has never had a real blonde before. Incredibly, she has not mentioned a rubber. Normally, he would put one on with a ******, but this is her first time. She is almost for sure clean, so why bother? If she is dumb enough to take him skin to skin, he sure isn't about to complain.
He rapidly gets onto the floor and onto his knees between her legs and reaches out to feel her snatch with his hand. "Wow baby. Your pussy hair feels so soft and fluffy."
After getting a good feel by running his hand through her golden fur for several seconds, he runs his finger up and down her slit for a few more seconds and then inserts a digit into her tightness. When he does so, her pussy quivers a little and tightens up even further around his finger. This is unbelievable, he thinks, she feels almost like a virgin. Cramming my dick into her is going to feel so good.
With his body trembling uncontrollably, he eases his hips forward. Then with a shaking hand, he shoves his huge organ down so that it is lined up against her beautiful blonde bush.
He makes a feeble attempt to hit her hole, but the target is small and his hand is shaking. He likes it better when the woman puts it in anyhow. It is like she is hot for his cock and wants it really bad. He grabs hold of her breasts again and tells Sherry to aim his dick for him. Sherry excitedly grasps his dripping dick and gingerly places it against her hole. Yes, he thinks, she knows just where to put that thing.
For Sherry, it is the moment of truth. She is about to give a quick little sample fuck to her first customer, and he is big. "Take it slow at first until you get it in," she whispers softly.
Fortunately for her, the wetness helps out because when he pushes the head partially into Sherry, she gasps because he is stretching her to an incredible width. As his thick head slowly slides deeper into her, Sherry groans loudly and digs her nails into his ass as her vaginal canal is opened to the maximum width it will go.
Sherry is whimpering as he penetrates and the customer pauses before his knob has gone completely through her lips, "Are you OK? I'm not hurting you, am I?" He sounds concerned, but in actuality he hopes that it is hurting her, just a little, but for real. As he is speaking, he is holding the thickest part of his dickhead in the middle of the tightest part of her cunt, which is the vaginal entrance.
Her lips are just outside that hole, and they too are being stretched incredibly far. He is stretching her almost painfully, and there will be no relief until he either moves forward so that her aching lips can get some relief around his slightly narrower shaft, or until he pulls it out. Of course he is aware of this and to add emphasis to the size of his dick he is deliberately holding himself at this point of his entry.
Sherry is gasping as she answers, "No, it's alright. If I want to be a ****** I need to be able to do this kind of thing. I just, it hurts a little and I have to get used to you, to your size I mean." She gives him a caress on the side of his face. While she is looking Into his eyes, Sherry's lips are trembling as she says, "Go ahead."
The customer shoves in another inch, and Sherry sighs in relief as her lips gratefully close down around his narrower but still thick shaft. Then, remembering how good she has felt when he first entered her, he wants to experience the entry again, before she gets stretched out.
"That felt pretty good. Let me do that again to be sure.”
He slowly pulls his dick backwards, taking her lips along for the ride until his dick head is completely out. As Sherry sighs, he enters her again with just the head.
Once again Sherry groans as he subjects her to extreme stretching, but this time the head of his penis is wet from her juices and her groan sounds more like pleasure then pain.
The customer pauses there, holding still as Sherry slowly realizes that maybe she is able to accommodate his thickness after all. He waits. Her eyes are closed and he watches until her frown evolves into a smile. Then she opens her eyes and looks into his. He smiles at her.
"Did you like it when I shoved my head in the second time? It sounded like you did."
Sherry hesitates, and then answers honestly. "It still hurt a little the second time, but it felt really good too"
"Well, in that case, let's do it again."
With that, the customer pulls his dick completely out and shoves it slowly forward again, making Sherry groan as he penetrates to just past his head. "Again," he says, and moves backward with his hips. His dick pulls out and then moves forward. This time he slides smoothly all the way through her lips with the head and goes a little beyond. Her body quivers and her nails dig into him, but she does not cry out. Instead she gives out a little sigh of pleasure.
"Yes, you took my head real nice that time baby. I think you'll work out just fine as a ******." With that, he pulled completely out and eased forward once again, and this time Sherry giggled slightly. This head fucking seemed to be turning her on. She was well lubricated now so he did it a few more times, pushing forward till the head was in, and then pulling it all the way out, each time causing her tight lips to come along for the ride.
"Have you had your sample," she asks, remembering that her husband is waiting, somewhere out there in his parked car?
"Almost done, baby. I need to see what you feel like down deep. I'm going to go all the way, inch by inch." Trying to go deeper into her incredible tightness, he takes several short strokes of an inch or two while Sherry gasps and moans. This feels so good that he decides to delay his entry to the deepest reaches of her cavern for just a little while longer.
Meanwhile, the man is still squeezing and fondling her lovely firm boobs. Finally he can resist no longer and begins working deeper into her. He is deliberately taking it slow to add emphasis to the length of his cock as he slides further into her soaking wet but oh-so-tight cunt.
He manages to prolong the entry, aided by his length. By the time his balls have made contact with her beautifully rounded ass, Sherry has her legs wrapped around his waist.
The customer has already gotten a lot for his thirty dollars. A complete blowjob with swallow, great feels of her wonderful breasts, and now total penetration. Now the only thing left is to go for some good fucking until he blows his load deep into her delightful pussy. "Yeah baby, you've got it all now." When Sherry nods with her eyes closed, he decides to ask Sherry some questions in order to distract her so that she won't stop him before he gets to come again.
"I'm pretty sure that it is by the way you felt and acted when I put it in, but tell me baby, is this the biggest dick you have ever had?"
The excitement in her voice made it obvious about how she felt. "Yes, yes, way bigger than anyone else."
The customer trembled and began fucking her a little faster. He had expected her answer, but it was still good to know that he was her biggest, which excited him tremendously.
"How many men have been in your pussy before me?"
"Just three, no, four, including my husband."
"Have you been faithful? By that I mean, is your husband the only man you have fucked since you have been married?"
"Yes, only him. The first two were just little boys in high school, and the third was a friend of my husband's that I did it with before I got married."
"A friend of your husbands? Did your husband know about it?"
"No, that was my little secret." Sherry giggled.
"And they all had small dicks then?"
"No, not small, but yes, compared to you."
"Hmm. You are almost a virgin then. I wonder how your husband sitting back there in his car would like it if he knew you were getting such a big cock in your tight little hole right now."
Sherry paused for just a moment before answering. "I don't know. I think he would be jealous because he always tells me that he has a big one. He's a little bit bigger then those other boys were so I used to believe he had a big cock until until I saw yours."
"And not only after you saw my dick but also after you felt it inside your pretty little pussy?"
"Yes, especially after this!"
As Sherry spoke she raised her legs still a little higher around him. The customer is really enjoying this. This gal is just young enough and inexperienced enough that she is willing to talk about her personal sexual experiences, and just gullible enough to believe most anything he tells her. "Well, your hole won't be as tight as it used to be after having me inside it, but you needed me to come along and stretch you a little bit. I'm amazed that your husband would let you pass your pussy around, especially when some man like me might come along and feed you some really big meat."
He pulled completely out and paused with his dick at the entrance to her pussy. "Now feel this honey as I slip it all the way in with one slow steady stroke."
Sherry trembled. Yes, as soon as he had pulled out, she had wanted it back inside. And when he pushed that head in and then out, if felt so good, so very good. Holding her breath, she waited for that wonderful entry once again.
"Ooooooh." Her arms tightened around him and her entire body shivered as he penetrated deep. Yet, even now, he was saving the last inch or two.
"It feels good, doesn't it?"
"Yes, oh yes, I really like it."
See what I mean," he asked her?
She looked into his face. "What? What is it?"
"Your husband can't be very smart. Here you are, with your first customer and already you're getting the big meat sample and you are going to enjoy fucking me more than you ever enjoyed your husband. He should have known better."
Sherry giggled and sort of hugged him. "I think you may be right."
That was it. She had just agreed, maybe without being aware of it, to go along and fuck him until he, or rather until they were finished. The sample fuck concept was now behind them.
Then he penetrated her once again, going slowly, and when she moaned in appreciation, he began giving her a nice full-length stroke. He kept going slowly all the way until he was finally buried to the max. As he was sliding in, Sherry was moaning softly during the entire entry.
It seemed to take forever for the nine inches to reach bottom, and yet did not last long enough. Her eyes were closed, and her fingers dug into his rear when she felt his balls contact her rear and his mound come up against hers. He was finally all the way into her.
"How, how long are you, anyhow? It feels like it's a foot long."
The customer laughed. "Well, I'd love to have you go off believing that I had 12 inches but you have already seen it before you sucked and fucked it, so I'll have to be truthful. It's over 9 inches long, maybe closer to 10 than 9." Like most men, he had exaggerated his penis size, but only by a little. "Yes baby, this is what you need so that in the future it will be easier to take all those guys if you keep on being a ******."
"I guess I should say 'thank you'? then," said Sherry with a giggle. "It is nice of you to be breaking me in for my future customers."
With that, the customer is laughing inside as he begins pumping steadily, taking long strokes and causing Sherry to hold her breath in ecstasy. The customer figures that since she has gone beyond the 'giving a sample' phase he takes his time, holding back to make it last.
He starts whispering into her ear. "This is so good baby. Your pussy is the best ever. Feel it as it takes my big cock. You're going to come baby, like never before."
This goes on for almost two minutes, and then Sherry suddenly exhales and grabs a hunk of air. She sighs and places her hands on his hips, making him stop. She tries again to catch her breath. Her orgasm is imminent. If she lets herself come, she will keep coming and asking him to give her more. Sherry is not supposed to come because she is learning to be a ******.
Her husband has told her this. She is not supposed to enjoy any fucks she gets, just do the job and collect the money is what he told her.
The customer senses that she is holding back. "What is it baby? Afraid to come?"
Sherry, being naive, answers truthfully. "No, my husband says that I am not supposed to enjoy my customers when I do it. All I am supposed to do is get it over with and collect the money."
He laughed, "looks like we overcame your resistance, doesn't it?"
She sighed, "Yes, oh yes."
He laughed again, knowing this was backfiring on her husband. "Yes, if your husband knew that you were getting and loving having a big, fat cock up your tight little cunt, I'll bet he would be jealous as all get out."
He was right, but he had also reminded her of her husband and the rules he had laid down. Sherry is more than enjoying this sample fuck and she feels an orgasm approaching. She has already waited too long because he feels so good. But she had laid down a rule of her own, 'Just a sample.' Now, feebly, she tries to enforce it. Gasping, Sherry says, "O.K., you have had your sample."
The customer grins. What's the matter baby? I think you were about to come."
"No, I'm just supposed to be giving you a sample, remember? This is so you will come back and buy me again sometime."
He had been thinking that she had forgotten about the free sample thing. He needed another excuse to keep this going. She's a dim bulb, so I'll feed her some B. S. along with my cock. His hips start to move again with short strokes as he says, "Well, all I've done so far is spend a lot of time getting it in and getting you all wet inside. This is really hard work. You can tell how hard the work is by feeling the sweat on my back."
It was funny, and he almost laughed when her hands went to his back. Sure enough, his shirt and skin were wet. "Now to be fair, I get to see how you feel while I do a little fucking. I'll take a few strokes and then I'll decide if I want to buy some in the future."
"Oh, I guess that sounds fair," Sherry says with a little frown. "Do it for a little longer then."
Laughing inside at how dumb she is, the customer starts pumping. Of course, since Sherry is enjoying this fucking immensely, she is accordingly being weak in her resolve to only give him a sample.
Taking long strokes with his dick, he places his arms under her legs and pulls them even higher around his waist. With his arms wrapped around under her knees, he begins grabbing her breasts again. Pulling his ass strongly back and forth, he takes long strokes with his shaft. As his testicles begin bouncing off her upraised buttocks, the car begins rocking.
Going for more, he presses his lips to hers. Sherry turns her head away. She is on the edge of orgasm, and kissing him might put her over the edge. "Wait, what are you doing? I'm not supposed to be kissing any of my customers, I don't think."
"Some customers might want to kiss you. They might even pay you more if you kiss them, so you need to practice."
"That sounds true enough. I guess you might be right about that. Kiss me then."
He has already come once. Control now is not a problem, despite her beauty and youthful tightness. He begins pumping again and this time, when he presses his lips to hers, Sherry kisses him passionately. As she kisses him he changes his technique. He is strong and she is little, so this is easy for him to do.
He lifts her completely off the seat by placing his hands under her ass and begins fucking her by holding his penis still and moving her hips from side to side, causing his penis to rub up against the sides of her vaginal walls. At the same time his pubic mound pushes her clitoris from side to side.
She is his now, and it is not long before Sherry has lifted her legs all the way over his shoulders. He is hitting somewhere up there, somewhere inside up in the top of her vagina. The feeling is so intense, more so than when her husband would rub her clitoris with his pubic mound or even when she would use her hand on herself.
"Do you like this baby? Does my cock feel good in your little pussy?"
"Yes. Like I said, my husband told me that I'm not supposed to like it when I let a customer fuck me, but I can't help it. You really feel good."
And then, without warning, the customer slips a fingertip into her ass. It slides in without pain because her ass is slippery from all the juices from above. She gasps and starts to protest, and he heads her off by saying, "A customer will expect lots of things, remember?"
"Yes, yes, that's right." She hugged him tightly and almost sighed as she finished what she wanted to say. She was his to do with as he pleased. "Do it all, do whatever you think they might want."
Sherry, in her naivety, actually believes what she is saying, but the desire to fuck this man is strong too, so strong it would overpower any resistance she might think to put forth.
As he pumps deeply into her, he also goes as deep into her ass as his finger will allow. He is stretching her vagina so much that he can actually feel his penis through the wall between her vagina and rectum with his finger.
He wonders if perhaps he should try to fuck her in the ass, and decides against it. He could probably talk her into trying it under the pretense of teaching her, but her pussy is too good to pass up, and that's where he wants to come.
"Think about this baby. Since your ass is so tight, you might want to think twice if some customer wants to fuck you in the ass. If you decide to do it, better charge him more and make sure he isn't as large as me."
"Yes. Thank you for warning me. This is so nice of you to teach me these things."
Then he gives her everything at once. He wriggles his finger in her asshole. He gives her full-length strokes with his dick, and kisses her passionately. It would seem, for the moment at least, that he has total control over her.
Testing her and his ability to please, he goes further; "If you could, would you leave your husband and live with me, maybe marry me?"
She can't believe what she is hearing. Is he serious? "I don't know, maybe."
He smiles inwardly. Yes, if he wanted, he could even drive off with her now and she would stay with him. But of course, he has a wife at home. She is not as pretty as this ******, but almost. His wife is not built as nice as this gal, but close. His wife is not as tight, but with his big penis, all women feel tight. The main thing is, his wife is still a pretty good wife. Deciding not to push it any further when he can't follow through, he concentrates on his fucking.
Sherry begins whimpering. There is no holding back now. She has to come, customer or not, she has to let it go. Her nipples are like steel and he can feel them pressing into his chest even through his shirt. Still kissing him, Sherry is taking the thick grinding shaft as deep as it is possible for him to reach and she begins to come.
This orgasm is unlike any other. This is a clitoral and G spot orgasm combined. She starts squealing and for the first time her pussy starts shooting fluid. It is spraying out and over his shaft and bouncing balls, and from there it is running down and soaking his seat.
Sherry goes almost wild. She begins alternating between trying to kiss her lover and catching her breath. Somehow she manages to gasp out the words, "Oooh, Oooh, oh honey. Oh my. You are so good. So damned fucking good!" If her husband had been parked just a little closer he would have heard, she was so loud in her pleasure. The customer smiles to himself. He can feel her contractions around his finger in her ass. She is coming a good one, there is no doubt about that.
It goes on. It is a warm summer night outside but inside the car it is a very hot summer night. He continues to pump. Sherry is shaking and whimpering, and her body, along with her face and hair, is soaking wet. Another orgasm hits her. Never has Sherry come for such extended periods of time and so intensely. The waves of pleasure roll through her body, over and over.
The customer is not having any problem holding back since he has recently come so hard in her mouth. She is weak and barely moving now. Another two or three minutes pass while he continues to stroke deeply into her and pull her hips from side to side. She is regaining her strength and wanting to come again.
He has found that a finger in her ass seems to arouse her to even higher levels so he keeps his finger in place. Sherry continues to gasp and moan as she comes still once again. Finally Sherry reaches a point where she is exhausted and no longer coming, and he slowly lets his finger come out.
After awhile she manages to speak with a halting, gasping voice as he continues to stroke deeply into her. She is weak, and her voice is self-conscious, almost ashamed as she admits what had happened to her. "I... I don't know what happened. I've never felt that before. I started coming over and over again. My husband said that is not supposed to happen, that all I will, that all I should do is not feel the men and just earn my money. It wasn't supposed to be like this."
"Well, that's because I know what I'm doing baby, and I have this equipment here that is kind of special, if you know what I mean." With that, he leans forward and kisses her once again.
Sherry whimpers and returns his kiss. A tear forms at the corner of one eye. She is enjoying this man more than she has ever enjoyed any man, and he is only supposed to be a customer. Because of experiencing all this pleasure, does this mean she is cheating on her husband?
"Yes, I guess I do," she answers in response to his comment. "You, your equipment I mean, is really special."
"That was your best orgasm ever, wasn't it?"
Sherry giggled. "Well, actually, it was several best orgasms."
"I know," he said. "You started shooting all over the place and got everything under us soaking wet."
"I did?" Sherry leaned forward and felt under their bodies with her fingers. "Oh wow. Did I do that? I'm sorry. I've never done that before. I hope it doesn't stain your seats."
"Don't worry about it baby. That come you had was almost as much fun for me as it was for you."
Grinning proudly, he slowly drops her back onto the seat and places his hands over her heaving breasts, which are wet and shining in the light coming in from outside. He starts stroking again and Sherry moans softly. She might be worn out, but if he keeps doing that she will soon be climbing towards another series of orgasms.
The customer is getting close to an incredible orgasm of his own when he does a dumb thing and pauses to tell Sherry how much he is enjoying his free sample.
Sherry has temporarily gained control of her body and says, "Free sample? Wait, I forgot something. Pull it out." As she speaks, Sherry pushes with her hands against his hips.
The John can't believe his ears as he reluctantly pulls it out. His penis is about to explode. Feeling suddenly empty inside, Sherry hungrily eyeballs his cock. It is all slippery and shiny from her juices, and looking red in color as it throbs and jumps around all by itself. She reaches out and feels it once again and a blob of pre-fluid runs out and down the side of his shaft.
Sherry licks her lips, bends down and laps up the slippery clear fluid with her tongue. She just has to have more of this wonderful cock, but she has to do it right. Sherry opens the car door and says, "Keep it hard. I'll be right back, I need to talk to my husband."
As Sherry spreads her legs and slips out of the car her blouse is raised above her breasts, her skirt is up around her waist and her tits, garter belt, nylons, ass and pussy are showing. Fortunately no one is nearby to see when she stands up and softly closes the door behind her. Pulling her blouse and skirt down as she goes, Sherry runs back around the corner.
Then, realizing that she is already on the side of the building where her husband is, she turns around, looks around, and runs towards her husband's pickup. Gee, he was over there the whole time, and I didn't know it.
Her customer, not quite understanding what is happening, waits for her. He wants to laugh at how silly the dumb blonde is acting, but he can see her wonderful body, even from here, and his dick is hard and throbbing as he holds it in his hands. When she gets back, he is planning to fuck her even longer than before and make her come again before he drops his hot load into her tight little cunt.
Meanwhile, Sherry approaches the family truck with her heels clicking. Harry is all involved in the ball game and has lost track of time. Hearing Sherry coming, Harry looks up and is startled to see her disheveled, sweaty condition. What the hell? All she was supposed to be doing was a hand job for 30 bucks!
"Harry?" Sherry says breathlessly to her husband, "Can you loan this guy seventy bucks?"
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