My Transformation

[dianeDavis]

I’ve been asked to give more details as to the events of my feminization and ownership. Hopefully this fills in some blanks and questions many of you have. if you have more don’t be afraid to ask.

It was February 2000, I was 36 years old. My wife Eve, was 32, 5’8”, an interior designer working from home. We had been married for 9 years and had a 5 year old son. You could say I was a pretty average man back then although looking back I could say that I had always been a wimp. I never played any sports in high school or college. I never was very academically inclined either but did well enough to go to college and get a degree in accounting. I was working for the same firm for about 10 years and in that time I never gotten a raise and was always afraid to ask one. I had also gained weight, I was skinny though out high school and most of college but I was weighing around 210 pounds at 5’7” being not active at all. This inactively let to Eve and I no longer in being intimate with each other for about a year.

It was a new year and I had gotten tired of being me in a sense. I thought I was going to go and change my life around. I decided to go and lose the weight I had gained and become the man I thought I should be. I went looking for a gym to go to. I decided I wanted one on my way home from work and a place that wasn’t a chain since I was and still am about helping out small businesses. It was in my search for a gym that I found my future master’s gym.

I wasn’t much of a gym guy so I was pretty nervous. It was also in a heavily black neighborhood and I was a bit nervous going in but I also felt like it would be racist if I didn’t check it out so I went in. It was a nice local gym large room, mostly weight machines and free weights, with two elliptical machines, treadmills and a bike. When I walked in the owner, Darryl, greeted me warmly; little did I know that this was the man that would change my life forever. Darryl was 26, 6’4” very muscular and I felt a bit intimated by him but not in a frightened way. He instantly went into sales pitch mode with me showing me the gym, the locker rooms, the he equipment, asking me what my goals were. The sales pitch worked, plus the fact that it was one of the cheapest place I found and on my way home it all seemed like a great deal. Darryl said that he would become my personal trainer at no extra charge to help me reach my goals.

He set a pretty intensive schedule for me, at least I thought so at the time, of going to the gym 3-4 times a week, I was really only thinking of going for 1-2 times but he said that if I wanted to see results I had to go for it. Eve for her part didn’t really care much that I was going to be at the gym that much, our relationship was pretty chilled at the point, she was glad that she could focus on her work more during the night than worrying about making dinner. He made it seem very personal for him so that if I didn’t show up or messed up I was insulting him in a way and I didn’t want to disappoint him. I thought the work outs would be mostly with weights and build up muscle strength since I heard that muscle burns more calories, but Darryl was insistent on me doing more cardio, stretching and light weights, said I needed to lose the fat first before I could focus on getting muscular.

After about a month Darryl asked me if I would like to go out and have a beer with him. I jumped at the chance, I didn’t have many guy friends and the guys at work mostly ignored me. The chance of becoming friends with Darryl was a dream come true. I heard him talk about how much he was getting laid and how awesome his life was, it brought me back to high school when the jocks would talk the same way and I would wish I could be like them or be friends with them so I could get their scrapes. Maybe becoming friends with Darryl would give me more confidence at work and with Eve even.

The bar we went to was his choice, close to the gym, not the type of place I would’ve went into, Darryl noticed my nervousness and made a comment about me not being used to being around brothers. It the comment insulted me in a bit that he was calling out my whiteness but I felt like I had to prove it to him that I was cool so I followed his lead. It was just a normal bar and I found myself feeling silly. It was nice to get to chat and chill with Darryl. His confident personality was seen throughout the room as random friends of his came up to say hi to him. We talked about work, I found out that he owned another gym and a multifamily house. I did the math quickly and figured he was worth double or triple my net worth and he was already 10 years younger than me. Told me how he went to college because of football and actually studied and worked hard in class to get his business degree was impressive. For me my parents paid for my school and I really didn’t try too hard but graduated anyway, I saw how motivated he was and it was impressive. Told me all his conquests with women, made me jealous, besides Eve I’ve only had sex with one woman. I showed him pictures of her and he complemented me on her and joked how I even got her. It was nice to have like a guy’s night out, I never really had one before.

So that became our thing, I would work out with him about 4 nights a week and we would go out for drinks afterwards about 2 of those nights. It was fun, I was learning more about sports, I felt like an idiot with him there explaining me things that I should’ve learned when I was like 8. He also kept on telling me his sexual conquests from the week before. He would also always order the drinks for the both of us, it came naturally to me to take the backseat from him, plus he knew the bartender so it was just easier to let him do it. Darryl would also insist on paying tap. When I tried to it would always lead to him telling me that it was he treat since he was taking me out, I figured hey free beer, plus I was paying him for the training so it was like we were keeping even with each other like friends would.

It was in April that like the first warning sign of my fate happened. At the time though I thought nothing of it. We got to the bar sat in our by now regular seats. Instead of order our regular beers he orders himself a beer but says that I will have a cosmopolitan. I look at him with a confused look and he just gives me a look that basically said I’m paying for this drink so you better enjoy it. Not wanting to insult him I drank it. It was good and there was more alcohol in it than a beer. He asked me if I liked it and I said yes, he said “good because there is less calories in it than in a beer.” It made sense then to drink that instead of beer. Looking back though I can see that like even then he was testing me. The just doing cardio, him always ordering, then moving on to the cosmos. A real man would stand up to him at some point, but I was just following his lead.

The next time I went to the gym it was normal routine until it came for time for us to clean ourselves up. Darryl told me that all the other members go to their houses to shower and I was the only one using the public shower messing it up. I should use his private office shower instead so not to mess up the public ones anymore, made sense. His private bathroom was big and nice, so I would shower first and then he would shower. After about using his shower about 5 times, he comes into the shower while I was showering. He said it doesn’t make sense for us to be waiting for each other and the shower was big enough for the two of us. It was the first time I saw him naked and it made me feel so small and weak next to him, even more than usual. I saw his penis and saw that it was larger than mine soft than when I was hard and I quickly looked up at the ceiling. Darryl acted like nothing was wrong and that it was all just completely normal for two guys to shower together. He did play football in college so like I thought it was normal for him so I didn’t want to make a deal about of it appear uncool or a wimp in front of him being uncomfortable showering with him.

We continued to shower together and at first I was always nervous but the more we did it the more I became used to seeing him naked and being naked around him. I started staying in the corner of the shower trying to stay far away from him as possible. As I got used to it though I would shower more normally around him and sometimes our bodies would touch or glance each other and when that happed the first time I jumped, thankfully Darryl acted like nothing happened. If he said something I would’ve been mortified. The next time our bodies touch though it was like a bolt of electricity went through me and my penis got hard, thankfully again Darryl was a gentleman and didn’t say anything about it. By May it was normal for us to shower, sometimes us even washing each other, it was so taboo but so exciting at the same time.

After a workout while I was getting nude Darryl came over with a bottle, that had no label on it and he told me to stand still he was going to put some lotion on me because he noticed that my skin was dry. I didn’t think it was dry but I was afraid to like push back against him so I let him put the lotion on my body. He applied it to my body from the neck down. He even told me to put it on my genitals and pubic hair. My body all over started to burn but he told me not to touch it, after about 5-10 minutes he let me run into the shower, I showered off all the lotion and all my body hair came off as well. I was pissed. I yelled at him that why he did that to me and that I’m hairless and what am I going to tell people. He explain that by removing my body hair that I would sweat less and be easier to clean, all guys who are into working out are hairless. Darryl in fact was hairless except for his pubic hair. I was mad that he tricked me into it but it did made sense. I wish he just would’ve asked me but I guess if he did I would’ve made more of a fuss about it.

Everything else he acted like it was normal, we showered, and then went to the bar. Once I was clothed though my whole body felt it was like electric and could feel how hairless I was. When I got home and got into bed my sheets felt so new and different, it was just fun rubbing my legs across them. When Eve got in bed with him she noticed that my arms and legs were now hairless and I told her what Darryl said, that it would be easier to clean and I would sweat less and that is all she really asked about it. After a week it felt natural to be hairless, it did seem like I would sweat less and it just felt better not to have all that hair on me, not that I was the most hairy person but it was just nice to be smooth and clean.

Things were pretty normal, going to the gym, showering together, going the bar, I was seeing results from the working out, lost about 20lbs in the 5 months since I started working out with Darryl. The next development happen when we were changing after the shower to go to the bar. While I was about to finishing drying myself off, Darryl through a pair of panties at me and told me how they were from a college girl he fucked from the week end before. I asked about the sex and why he kept the panties. While I was holding the panties Darryl said that I should try them on that I might like them. I baulked at the idea of wearing panties. He said that I shouldn’t be such a faggot about it and just try them. Him calling me a faggot made me feel like I had to prove myself to him so I put on the panties. My penis got hard instantly when I put them on. I felt so embarrassed but turned on at the same time, a whole new waves a feelings overwhelming me. He chuckled a bit from seeing me hard, made me feel even smaller and more embarrassed. He walked up towards me, I felt so small and weak next to him. He put his hands down my panties, funny how even then I thought of them as my panties not the girl he fucked that weekend. He put his hands down my panties and took my penis and testicles, he pushed my testicles up inside me, pushed my penis down, pulling up the panties hard. Evidence of my male sex was now hidden and I was utter humiliated, I was holding back tears a bit but I was still super turned on. He then said that was the proper way to wear panties and proceeded to get back to dressing normally. I stood there in shock uncertain what to do. He was now just pretending that nothing happened at all, that his hand just didn’t manhandled me. I was in a stupor but I did start to put on my clothes, but I was still wearing the panties.

We got dress and went to the bar. I was on edge the whole time, turned on and yet worried that everyone that saw me could tell that I was wearing panties. Darryl acted normal at the bar, usual talk of sports and girls, barely paying attention. He did asked before I left if I was liking the panties and I just looked away and muttered yes. I got in the car, drove home, got the car in the garage and sat there knowing that I couldn’t chance Eve discovering that I was wearing panties. Still in the car and me hard as ever, I open my pants pull them down and rub my penis still in its panty prison, it straining against and feeling that it was larger than it ever was. I take off my pants and the panties in the car and proceed to use the panties to jerk off while Eve was in the house waiting for me to come in. The orgasm I had was the best thing I ever had, I squirted cum on the dash of the car. I cleaned myself up with the panties, I take my boxers from my bag put them on and I throw the panties in the trunk of the car. I was so confused and felt so guilty too for doing what I just did but it was so erotic too, something I never felt before.

I was afraid to go back to the gym to face Darryl. I felt humiliated in front of him and that I was not a man. When we went through our usual workout routine. I was nervous the whole time if he was going to say anything about the panties, especially if he would say anything loud enough so the other guys would hear it. Thankfully he didn’t say anything and acted normal. I was thinking that I was going to go home to shower because I didn’t want the repeat or even talk about the panties. When it came time to shower though I went with him to his office. We showered, while we were drying off though he asked about the panties. He wanted to know where they were so he could give them back to the girl, I go them out of my gym bag while I’m still nude. I hand them to him and he sees the cum stains from me and says that I must have really liked them. I turn bright red and he said that it was cute when I blush and I felt my stomach doing flips.

 

[naughty-cumslut-neva]

You've become such a pretty woman! I can hardly wait to hear more

 

[18mDresdF4prom]

You've become such a pretty woman! I can hardly wait to hear more

I agreee. I normally do now read xxx stories cuz they are too much for my little brain. Bu ti one half way thru Daine's post and will finish it. my trans has been similar but different. you know, mostly older boys since junior high
I am proud to say I will complete my Assoc degree this May. and O focuses will attend Graudation as a female just like i have gone here all along as a girl. i have found ways that are less awkward to tell boys who are interested that I am really a boy. I am on girls' swim club so the has been great
Get back to a sport I am good at but as a girl. 5'3 145 lb 34C (nearly C) 34-28-41
real and legal name Mary since 18

Diane, please tell more
love, MARY

 

[dianeDavis]

I was afraid to go back to the gym to face Darryl. I felt humiliated in front of him and that I was not a man. When we went through our usual workout routine. I was nervous the whole time if he was going to say anything about the panties, especially if he would say anything loud enough so the other guys would hear it. Thankfully he didn’t say anything and acted normal. I was thinking that I was going to go home to shower because I didn’t want the repeat or even talk about the panties. When it came time to shower though I went with him to his office. We showered, while we were drying off though he asked about the panties. He wanted to know where they were so he could give them back to the girl, I go them out of my gym bag while I’m still nude. I hand them to him and he sees the cum stains from me and says that I must have really liked them. I turn bright red and he said that it was cute when I blush and I felt my stomach doing flips. He goes into a bag and pulls out another pair, this time they were pink satin, he throws them at me at catch them. I feel the material through my fingers and my penis is already stirring, he staring at me intently, burning a hole into whatever sense of manliness I thought I had. I put them on the way he taught me, pushing my testicles up inside my penis under, smooth illusion of feminity in front. He smiles and tells me to turn around, I do so obediently. I’m embarrassed but the humiliation of the situation is turning me on more and more. He said let’s get dressed and we do.

We get to the bar but instead of sitting at the bar he directs me to a circular booth. We go inside the booth and he orders for both of us. His hand goes under the table, he starts to move up and down my entrapped penis. He asks if I like being in panties I said yes. He says that it suits me. Ask if I like being turned on by them and him playing with my penis I said yes. He then says, that from now on when I go to the gym or in his presence that I had to be in panties. I just looked up at him and nodded yes. He then said that he would not supply the panties and I would have to get them. I asked him what about my wife I couldn’t let her find them and he said figure it out and I in a trance just nodded yes. He told me to go to Victoria Secrets and get a variety of styles. He then rubbed me till I cummed. I moaned a bit and I don’t think anyone at the bar noticed us but I felt like all eyes were on us and knew exactly what was going on. After I cummed he told me I could go home. I didn’t want to, I wanted to spend more time with him but because he told me to go and I felt like I had to go. I drove home got into the garage, took of my pants, saw my cum stained panties and began to rub myself again to orgasm, I’ve never cummed twice in one day let alone within less than an hour of each time.

The next day after work I drove to a mall south of me, didn’t want anyone I might know see me buying panties. I was so nervous that everyone in the mall already knew what I was there to do and that all eyes were on me. I waked into Vitoria Secrets remembering the size of the panties that master gave me. I was overwhelmed by the options so many different soft things and I got hard already in my pants. A sales girl went up to me and asked if I needed help with anything, I got flushed with embarrassment and said no thank you, that I was just looking. She went away and after that I was like I just need to buy panties and leave, I grabbed different pairs, bikinis, thongs, boy shorts mainly and went to the counter. I bought about 15 different pairs went to the counter, I’m positive that this 20yo woman knew that these panties were for me. Me all nervous perspiring while buying these taboo undergarments for myself, a man. In reality the 20yo girl probably didn’t think that they were for me and just wanted me to get out of the store to leave her alone but that is something I’ll never know but at the time it was just racking through my head the whole time.

After I got my purchases I was on such a horny high from it all that I rushed into a bathroom sat in a stall and jerked off using one of my new panties. It was the first time I’ve done an act like that in a public space. It was so erotic. The thoughts going through my head of me a married 36yo man jerking off with panties that I will be wearing was so hot to me at that moment. After I cummed the guilt flooded over me. I quickly put the used panties back in the bag and I tucked myself under and pulled up the ones I was already wearing. I threw the purchases into the trunk of my car.

When I went to the gym next I made sure to wear my panties under my clothes. When I was done with my work out Darryl asked me if I got my purchases. I went to my car to get them. We showered. When we were done and I was nude he had me give him a fashion show. Trying on all the different panties I bought. He would ask me why I bought that style of that color. It was so humiliating and demeaning to be showing him my purchases. After I we were done we went to the bar and he acted like everything was normal again. It was these games of his were he would push me and then act like nothing happened which would make my mind do flips not sure where this was heading but I was loving it all.

The next two weeks I would wear panties for Darryl at the gym. He pushed me to wear them to work too. It was so taboo but so exciting. I was always afraid and paranoid that someone could tell what I was wearing under my clothes. I was always on edge while wearing panties thinking that someone was going to call me out on them at any moment. Keeping the secret from eve was exhilarating for me. I was feeling alive and excitement like never before. It was freeing in a sense too. I was focusing on making Darryl happy and that was making me happy. Anytime I got his approval from panties to my workout routine I felt better and better, he was like a drug to me which was so crazy because I never felt like that towards anyone before.

I was loving wearing panties, they made me feel alive and excited constantly. The next big step was we were in the bar at our booth, funny how already then I was thinking of it as our booth. Anyway he says to me that I was always with him at his gym or at the bar, I should be a good friend and invite him to dinner at my house. All the blood felt like it drained from my body. It was fun having it removed but now he wants to come to my house. It was then I realized that he already knew where I lived, if he wanted to he could stop by any time and tell eve what I have been doing at the gym besides losing weight. Before I could protest or say anything he told me that he’ll see me at my house that Saturday night. He also said that I should cook him steaks for dinner and to remember that I was to always be in panties in his presence. I sat there still in a state of shock afraid of what may or may not happen at dinner. He patted me on the leg, got up and left and said that he would be at my house at 6 o’clock.

The remaining two days I was in a haze not sure of the path I should take. I thought several times of going to the gym or calling him to call it all off. I thought countless times about throwing out my panties and go back to being a regular man for my wife and family. The more I thought about it though the more I felt like I didn’t want to disappoint or anger Darryl. He was a real man. He was dominate, muscular confident. Being with him and spending time at his gym did make me more confident in a sense. I was losing weight and I was enjoying what he was doing to me. Even though at times it felt like a cruel tease and could be seen as torturous.

I told eve that Darryl was coming over for dinner on Saturday. She was excited to meet him since I was spending so much time with him at the gym and she knew that we had become friends. She was excited for me because he was really my first new friend I had since college. I never really talked or meet up with those guys anymore, they got married and had kids too so we all drifted apart. Eve thought it was odd that I told her I was going to be cooking dinner since we had a pretty traditional gender roles back then. She joked about how I was doing the cooking for my new best friend and I wanted to impress him. I turned red with her talking about him like think, thinking if you only knew.

 

[dianeDavis]

6 o’clock came, I was busy in the kitchen when Darryl came over. Eve went to open the door. I walked into the room to see her open the door for him. He was dressed in a suit looking very handsome and successful. He hugged Eve kissed her cheek and said that he has heard a lot about her and has been looking forward to meet my better half. He came up to me gave me a high five handshake that made my body move unnaturally.

We had a short small talk, introduced Darryl to Kevin. Darryl brought a stuffed bear for him. We sat down had dinner. It was really just a normal dinner. Darryl did most of the talking. Talking about his training me at the gym and him seeing results in my weight loss. Him about him growing up and then getting a scholarship to go to college but being smart enough to get a business degree while he was in school. It was all very pleasant and put me at ease.

After the end of dinner we sent Kevin up to his room and had cocktails in the living room. I got Darryl a whiskey on the rocks and made Eve and I cosmos. Eve commented that I never drank cosmos before. I got red in the face. Darryl jumped in and said that it was healthier to drink cosmos. Made me think back to how even in my own home I’m doing what Darryl wanted me to do, even wearing panties and it made me happy to follow his orders.

The conversation was normal after that and it was about 10pm now and Darryl said he had to get up to work out before getting down to running his gym. We got up to walk him out, me thinking something else was going to happen, what I did not know but I was well paranoid, I was glad that the evening was ending.

While we were walking Darryl out, he turns around. He said that it was great to meet Eve and that I have a beautiful family. He then says that him and I have become really good friends and that he knows about the problems Eve and I have been having inside and outside of the bedroom. (We haven’t had sex with each other for over a year) He then says to Eve that he introduce the idea of me wearing panties. That the taboo was known to raise ones libido. He said that I loved to wear panties and that I wish I could wear them all the time but I was afraid of what Eve would think of me. He then told Eve that he knew that I never went down on her and that if I could wear panties all the time that I was willing to eat her out whenever she wanted. As he said this all the color dropped out of my face and I felt my whole world crushing me. I was too afraid to deny or say anything, I was just standing there wear panties under my clothes.

He then says good bye, hugs Eve and leaves. Eve throughout his speech was silent as well. Once Darryl left, Eve turns and doesn’t say anything and just goes upstairs to our bedroom. When that happened I thought I was going to get divorce and my whole world is ruined. I stay downstairs, do the dishes and clean up avoiding going upstairs. I was glad that I didn’t see Eve come running downstairs and out the house with a suitcase so I figured that was a good sign.

After an hour of hiding downstairs I decide to go upstairs and face my fate. Eve was still awake and waiting for me. She eminently asked if what he said was true. I felt like I couldn’t lie, especially since I was wearing panties and they did make my horny. If I tried to deny the talk about him saying that I wanted to wear them all the time would make me look bad since I was wearing panties at that monument and I also didn’t want to make Darryl look like a liar in case he like asked about it later. So I told her what he said. That he introduced me to panties. She asked how? I said it was through a dare, I thought the whole calling me a faggot to guilt me into them and then tucking my penis and testicles under didn’t need to be said. She asked if I liked wearing them and if they did make me horny. I said yes. We then talked about how I never really performed oral sex on her. I tried it once but I just wasn’t good at it and didn’t know what I was doing and like getting that close to a vagina wasn’t that appealing to me. Always looked like a weird alien world to me.

We got to the point in the conservation where she asked me if was wearing them right now. I said yes. She asked if I had more than just what I was wearing, I told her the truth that I kept them in my car trunk and would change in and out of them either at a gas station bathroom or in the garage or in our bathroom. When I told her I was wearing them she asked if she could see me in them. I stripped down to my panties. She said they were cute and that I looked good on them. She also mentioned that my weight was down as well. It had been 6 months since I started at the gym and I was now 170lbs.

When I got down to my panties, Eve then started to shimmy her pants down and her panties and told me that I needed to hold up my end of the deal. I went down on her, gave her an orgasm and she fell asleep afterwards with me in my panties.

 

[dianeDavis]

The next morning I woke up and put on a fresh pair of panties. I assumed since I ate out eve and Darryl said that I wanted to wear panties all the time I might as well do it. I got dressed and then made breakfast for Eve. She didn’t say anything about me eating her out or about the panties, I suppose she figured that the less we talked about it the less awkward it would be. I was still annoyed at Darryl for him ******** me to her like that though and I meant to go over to the gym to talk to him about it.

I went to the gym and met him there. He asked about how was everything at home and that he was sorry that he said what he said but he thought it was for the best for me to not bottle it up and now I can wear panties all I want. I accepted his apology and I told him about the talk that Eve and I had and that I guess I’ll wear panties all the time. He laughed a bit when I told him about me eating her out in my panties and when I told him how wet and horny she was. After that we had our work out. During the work out I noticed he seemed to be much closer to me than usual although it might have just been paranoia and like he always worked out this close to me but I just noticed it.

After the workout we got naked and hoped in the shower. This time though he started to wash me more than usual and I got hard. Before he would just ignore my hard on but this time he took my 4” penis in his large hand which made me feel so small and week and he started to jerk off me off. Between the moans I was letting out I started to protest but he just shushed me and told me to enjoy it. Which I did immensely. The orgasm I had from him jerking me off was the best I have had in my life up to that point. When I did I just melted and he held me and made me felt safe and happy.

As I was drying off Darryl said he had some presents for me. Hearing this made me happy and he said I looked cute when I smiled. I blushed, I should’ve been more embarrassed by this whole thing, especially after he just had his hands on my tiny penis but I was in the afterglow of the orgasm. He gave me the packaged and it was wrapped in pink paper with a black ribbon. I opened it and inside was a matching panty and bra set with stay up stockings. When I saw it Darryl said that if I wanted to I could try them on for him. The way he said it was so sweet and nice and like I didn’t want to insult him by saying no and while I was going out panty shopping those weeks before I thought about other lingerie, what it would be like to wear it. I put on the panties, making sure to tuck my penis just like Darryl had taught me. He helped me with the bra, it was an A cup and I didn’t feel it but it did kind of pushed up the fat I had on my chest. The best was the stay up stockings, the feeling of them rolling up my legs were electric. Once I had them on my legs I was rubbing my legs together and loving the feeling. When I was in the set Darryl asked me to pose for him to show off his presents. I did a few poses not even realizing how much of a girl I was acting at that moment. He complimented me on my weight loss that just made me feel even more of a natural high.

After the posing Darryl told me to put on my clothes over the set and hose. I was worried about the bra showing under my shit but he told me that it didn’t that reassurance was all I needed. He asked me if I wanted more. I nodded. He then said lets go shopping and that he was going to treat me. I was naturally nervous at this. I felt like I couldn’t say no to him since he was being so nice and sweet to me. We went to his car and we drove to a mall. There we went right to Victoria Secret. The image I had in my head of me and Darryl at Victoria Secret looking at panties, bras and stockings was embarrassing. A married white man with a tall in shape black man looking at lingerie. I naturally assumed anyone that saw us knew that these things were for me and I was all red but so turned on by the fact. Darryl bought me about 10 matching sets, 3 of them with garters and stockings. We got back to the gym, which in itself was humiliating because we walked through the gym with Victoria Secrets bags to his office for the other guys at the gym to see.

I gave him a bit of a fashion show and he complimented me on everything I wore. He told me that I could bring the panties home but he wasn’t going to tell Eve about my new gifts and that it would be up to me if I wanted to tell her. I told him it was all too much at once and that I would rather not tell her. I took my presents though and hide them in the trunk of my car, the same place I kept my panties although now I was going to keep those in my dresser since Eve knew about that.

The pattern for that week was I started to wear stockings under my male clothes at work. I didn’t wear the bras just because I was way too paranoid about it showing through my shirts. When I went to the gym now in the shower Darryl was jerking me off and I was loving it.

Friday night while at the gym Darryl told me he was coming over on Saturday for dinner again. Fear swept through me. After what happened at the last dinner I was afraid of what he would say or ****** next. I knew I couldn’t say no, I was getting myself deeper and deeper with him. He came over Saturday night and thankfully nothing happened. It was a normal meal and the only embarrassing thing to happen was he asked Eve if things have improved since I started to wear panties around her and she smiled and conformed that it had. Besides that, everything went normally and I was very thankful for that.

The next day I went to the gym, did our normal workout routine. We were in the shower together, I’ve been loving him jerking me off, even though waves of guilt would wash over me at the same time. One reason was from the situation that I had been digging myself into. The other was the fact that I haven’t jerked off Darryl yet. So Darryl was jerking me off and I touched his cock. It was so hot and wet in the shower and it was just amazing how heavy and big it felt compared to mine. As I touched it began to get better and harder. Darryl said thank you to me. I got his whole 10” fully hard both my hands had to be on it to jerk him. As I was jerking him though he put his hands on my shoulders and gently pushed me down to my knees. I was in a trance focusing on his cock and I let him push me down on my knees. I was there starting right at his cock and looking up at him while he looked down on me with the water going over our bodies. While I was looking up at him and with my hands on his cock he just looks down and tells me that I know to do. I then kissed his cock. I was just a little peck on the head. I looked up and he said again that I knew what to do. I opened my mouth and took him into it. He moans out that I’m a good girl. The first time he refers to me as a girl. Having his cock in my mouth turns me on so much. It is so hot to know that I was making him horny. I move my tongue under the head jerking him off with one hand while my other plays with his balls a bit. It was such a hot erotic moment that I just was living in that moment right then. It didn’t matter that I was married and a father. No I was his girl at that moment and I loved it. I gave him head for about 20 minutes, as he got closer he put his hands behind my head and started to push himself down deeper in my throat, I guess I got about 6” of him inside my mouth before I started to gag and then he would let up and have me be able to breathe more. He started to tense up and told me that I was supposed to keep his cum in my mouth.

He cums and I want to swallow just out of a natural instinct but I don’t, some of it dribbles out of my mouth as he pulls out. He tells me to open my mouth to show him his cum in my mouth. I do and then he tells me to swallow and that I must always swallow his cum. I nodded, the scope of what I had just done washes over me like the water that is still following over our bodies. I’m still on my knees and I asked him are we gay now? He laughed and said no, that he was straight and loved feminity and women. He then said that if he loved girls and I just sucked his cock that I must be a girl then. He then told me to tell him that I was a girl. I repeated that I was a girl humiliating by the whole situation. He said that if I was a girl that I must have a girl’s name. He then told me that he would now call me Diane in private.

 

[SM4Fin2Blk]

Please continue Diane. I am an experienced cuck. I have also experienced some feminization at the hands of my former wife and our black Dom, but not to the extent that you have.

 

[mwm59]

Loved your story. Please continue with it.

 

[steevo895]

Yes, it is great story! So erotic and intense

 

[robinlove]

What a wonderful story.

 

[dianeDavis]

I was now reborn by sucking Darryl’s cock. He hugged me and told me to get dressed and he has some presents for me at his house. I was apprehensive about going to his house, I never been there before but I would do anything for him. I followed his car to his house. When we got there he lead me to the backyard. There he told me to strip down to my panties, bra and stockings, he told me that whenever I was inside his house it was going to be Diane in the house and no male clothing would be allowed. I was humiliated and afraid being outside in panties, bra and stockings but so turned on again. Darryl noticed my bulge in my panties, looking at it he said that he suppose that is a yes to his demands and I nodded confirmation.

With that he opened the door and let me in. It was so nerve-wracking to be in his house feeling so vulnerable in just the lingerie. Darryl acted like nothing was weird or wrong, he just showed me around the house like this was all just normal. After he showed me around he told me that he was very proud of me and had a few presents for me. They were two boxes wrapped up. I opened them like I was a kid on Christmas. The first box held a pair of 4” heels, the other was a dress. When I got both out Darryl told me that I should try them on. I put them on. He had me do a twirl for him. I giggled doing it. I thanked him and hugged him. I felt his hardness inside his pants. It was amazing to me since it wasn’t more than like two hours and he was already hard. I felt his hardness, I grabbed it. I got down on my knees and took out his cock. I was already addicted to it. I gave him another blow job. He telling me how pretty I looked and that I made a good girl made me want to suck him more and more. He fed me the second time that day and I swallowed like I was told the first time I sucked him off.

He told me afterwards that I will be having special workout sessions at his house instead of going to the gym but I would still go to the gym 1-2 a week. Whenever I went to his house I would become Diane, he always had a new pair of heels or a dress for me. When I was there he would make me do new exercises of moving my body in feminine ways, walking in heels, he started to train me in talking in a slightly higher octave. Darryl would sometimes cook dinner for me, or have a glass of wine or two, felt like I was going on a date every time I came over. We also would watch a lot of interracial porn and TS porn. I would put myself mentally in the woman’s position in the porn.

While I was being Diane at his house, I had to hide my true feelings of my life towards Eve. It was even more difficult when Darryl would come over for dinners. During the dinners Darryl would pay more attention towards Eve. Kind of leaving me in the shadows. I asked Darryl about it and he said it would be suspicious if he just paid attention to me. He thought it was cute that I would get jealous of Eve.

Eight months after I met Darryl now I viewed myself as his girlfriend. Anytime I saw him now I was sucking his cock, loving the attention he was giving me and making me feel wanted. I was losing weight but Darryl said to me that he had something to help me lose more weight. He gave me three pill bottles. I was to take all three pills every morning. I was apprehensive about taking mystery pills but he explained that two of them were supplements and the other one was an energy pill that would help me in losing weight.

Diane has been kept inside Darryl’s house being a good girl for him. He got met a brunette wig to add to my Diane personality. He would kid about how we should go out to clubs and he should show me off but I was too afraid of going out in public as a woman. He did push me to let him drive me around his neighborhood dressed as woman. It was frightening but exhilarating at the same time. My hand moved over to Darryl’s crotch. Just feeling his bigness through his pants turned me on and I took it out and gave my first road head.

My whole psyche was changing the more time I spent as Diane and the more time I spent with Darryl. I was seeing myself as a sexual creature, always horny and always ready to be on my knees and have Darryl’s cock inside of my mouth. When it came to me serving Eve though I always dreaded eating her out. It always felt like work for me. When I was younger I would have friends talk about eating out women like it was the best thing ever. To me though it was always a chore. It was something that I had to do now to keep Eve happy with me so I could stay in panties and be a girl for Darryl. How much did Eve really knew what was going on I was never really sure. People who I’ve told my story to think that Darryl had switched Eve much sooner than I know. Even though some believe that, I doubt it. The way Darryl was around her always had a cautious feel, well besides him telling her about the panties, but everything else he took his time with her.

Darryl started to have me read more woman’s magazines in my down time at his house. He told me to focus on the make-up tips in the magazines. He would get me a pallet, lipstick, blush, foundation, mascara, everything I needed to start to practice. (How I wish youtube existed back then). He would give me tips on what I could do to work better.

When I got decent enough Darryl had me dressed up fully and took me into the car. I thought we were just going to go for a car ride and I’ll suck him off. Instead we drove to a club that I never heard of, I was freaking out about going out in public. He calmed me down saying that it was a drag night and that it would be good for me to see other girls like myself. I was so nervous getting out of the car, I held onto his arm with all my might. It was crazy because when we got inside we got a lot of looks. I was worried that something was wrong but Darry just said it was because all the guys there wanted to fuck me and all the girls there wanted to fuck him. It was a bit of a ego boost.

The show was fun. It was nice to get out of the house and drink and have fun. It was like in the beginning when Darryl would take me to the bar after workouts although now my true self was out with him. It was nice to be close to him as Diane, have other people see but not worry.

After the show, Darryl and I went up to a drag queen called Jasmine, he knew her already, and they had mutual friends. He introduced me to her as his girlfriend which made my heart flutter a bit. It was weird being around talking to another “gurl” talking like girlfriends but it was also sweet. Darryl explained how I just started to dress and I could use some help doing my make-up. Jasmine took me by my hand had me sit down and she did a whole drag make over on me. Countoring, highlighting, fake lashes, the works. It was a lot to remember but the result was beyond anything I was doing at Darryl’s place with the info I got from the magazines.

I was living the dream I had a hot bf who loved me and was helping me become the woman I was meant to be but never knew until I was living it. But then the two worlds I had would collide. The one where I was happy with a handsome, dominate black boyfriend and the one where I was in a loveless marriage would merge and only one will survive.

 

[SM4Fin2Blk]

Wonderful Diane.....This reminds me so much of the situation I had with my wife and our Dom. The difference being my wife was in on my feminization from the start. Please continue.

 

[LindaAnnK]

This is soooo close to how my own sissy life began, even down to the Gym owner BF for the ex-wife. We should so chat!

 

[dianeDavis]

It has been 10 months since I first met Darryl and I was now dressing up enfemme for him anywhere from 2-4 times a week. I was wearing panties fulltime. When I would leave home for work I would have a bag in my truck of my car with stockings and even a corset that I would wear while at work. It was so erotic for me to have my girly things on while at work. I was able to do my make up a little bit outlandish but was comfortable being taken out by Darryl as Diane and having the world see me as his girl.

Darryl was preparing me to be his girl, one day while sucking him off while watching IR porn he stuck a finger inside my ass. It hurt a lot and was a shock but Darryl told me I would regret messing up on sucking his cock. So I just concentrated on his cock in my mouth as his finger slide in and out of me. I felt like his puppet with his finger inside me and like I was being ripped opened. After I got my prize of his cum in my belly Darryl took me to his bathroom. He told me that we were going to take a shower, I love being all wet with him. After the shower Darryl told me that I need to be clean all the time. He took out something that I never saw before, a douche. Darryl filled it up with water, applied lube to my ass and put the nozzle inside. The warm water filled me up, giving me cramps, I told him it hurt but he said that it had to be done. Once it was all in side he made me leave the water inside for a few seconds before I could sit down on the toilet and release. After it was all out he filled me up again with water, to get myself as clean as possible.

Now my insides matched my outside Darryl got a bag and took out a butt plug. First time I saw one and was frightened of having this thing inside me. Darryl asked me if I was his girl, I said yes. He then lubes up the plug and pushes it inside me. It rips my tight sphincter open, I tear up at the pain, Darryl caresses my back and he pushes it in calling me a good girl. It pops in, and Darryl tells me what I should wear it as much as possible. I walk out of the bathroom feeling the plug in me, another sign that I’m Darryl’s girl.

Twelve months and I was happier than ever with Darryl. I was in the best shape I ever was. Life with Eve though was still a bit of a struggle. I was eating her out still but not communicating with each other. Going through the motions of being husband and wife. I was always looking forward to being with Darryl. All day he was always on my mind. Thinking about what he would have me wear, what we would do, his cock, or if he would take me out.

I went to his house to the backyard around 9pm. I stripped out of my male clothes, wearing stockings, garters, corset, bikini panties, bra and heels. I walk in and master is waiting for me. He hugs me and kisses me, I melt into his arms. He has a dress for me to wear and says we’re going out. I get excited and we jump into his car.

As he’s driving I get a bit nervous as I noticed that we’re getting close to my neighborhood. I ask Darryl where he is taking me but he says it’s a surprise. A coldness comes over me as I see we turn onto my street and he parks in front of my house. He tells me to get out, I say please don’t do this. He says that it’s the best thing for me. I stay in. He gets out and goes around the car and grabs me by the arm and drags me out of the car. He’s pulling me towards my house, not knowing what is going to happen. Fear runs through me, what if Kevin opens the door and sees me dressed with Darryl. What is going to happen if Eve opens the door and sees me dressed with Darryl. I want to run away but Darryl’s grip on me is too strong.

Darryl knocks on the door. Eve opens it and sees Darryl first. She looks confused as why is he there since I was supposed to be with him at the gym. Darryl doesn’t say anything, he walks in towards her and kisses her. First time they kiss although during the dinners over the year master would flirt and touch her thigh gently in front of me. With the kiss I see Eve melt into Darryl’s arms. I am free from his grip but I’m standing there at my door where someone who I thought was my man was now kissing my wife. I’m standing there dressed up for a night on the town as Diane looking at a scene I couldn’t imagine.

The kiss breaks and Eve looks backs towards me in my dress. She doesn’t say anything, she has a confused look but then realizes its me. Before she can even said anything Darryl says that she needs a real man in her life. He then picks her up, kisses her and walks upstairs. Darryl tells me to come along. Not knowing what to do I follow them. I’m glad that Kevin was sleeping already. We get into our room and Darryl begins kissing Eve more, stripping her. He asks what does she think of me and she says that I make a pretty woman. I’m standing there not sure what to say or do. He has Eve stripped laying on our bed. He strips himself, making out with Eve sucking on her breasts. His cock is rockhard and he lines up for Eve’s tight pussy. He plunges in and she screams out in ecstasy and pain. He says to Eve that is what a real man’s cock feels like. Not the little clit that I have. Watching this I’m totally humiliated, rock hard in my panties, my nipples are solid and I’m also jealous of Eve for getting to fuck my man before I have.

They fuck for about 30 minutes, missionary position with Darryl kissing Eve and playing with her breasts. She orgasms like I have never seen within ten minutes of Darryl fucking her. I’m filled with fear that Kevin will wake up and want to see what the noise is about. Its hot watching them together but I keep on imagining myself being in Eve’s position taking Darryl’s cock. She shudders with another orgasm as Darryl tenses up and cums into my wife’s pussy. He asks Eve if she is on birth control, she says no. Darryl looks over to me and says that if I don’t want Kevin to have a brother or sister I should get down there and clean up the mess he made with Eve.

Flushed with humiliation, not sure what to do, I walk to the bed, and go on it facing Eve’s cum filled pussy. Darryl says that I know what to do. I go down onto her pussy and start sucking out Darryl’s sperm. I do it for about 5 minutes while Eve moans from the waves of pleasure and Darryl stands over us. While I’m on my knees worshiping Eve’s pussy I feel Darryl get on the bed behind me and lifts up my dress ******** my ass. His hands move around my pantied ass and pulls them down. I feel Darryl take my plug and takes it out with a small pop. He then lubes my ass and then I feel him enter in me finally. It hurts but I love it. He moves himself all the way in and slowly stars pumping away while my face is in Eve’s pussy.

It feels so much different from plugs, fingers or dildos. It hurts, it burns, but I love it. As he keeps going I start to push back against his thrusts, I feel him inside me. It takes lots of concentration to keep eating out Eve and getting fucked by Darryl. I felt a wave of pleasure that started to build from his thrusts. After 20 minutes I cum from his fucking. I let out moans of pleasure. While I was being vocal Darryl cums for the second time that night in my ass. Hot with sweat and the pleasure of sex filled the room. Darryl gets off of the bed and I feel empty without him in me.

He gets up off the bed and starts to get dressed. He looks at us and says that he wants us both but we would have to submit to him fully. If we do not we would never see him ever again. With that he leaves the room and the house. Eve and I are still shocked and dazed by the events of the night. We get dressed, me in panties and sweat pants and tshirt. We then discuss everything that just happened and that has been going on the whole year.

I shared that I felt like a woman around Darryl and that I was happier now than I ever had been. We discussed our marriage and how it hasn’t been one. We talked about the sex and how amazing it was. We had no idea what it would mean to fully submit to Darryl but we knew that if we didn’t that we would regret it and our lives would still be fully changed by him but not happy. We agreed what we had to be with Darryl.

The next day Kevin goes to school and I get dressed up as Diane the first time around Eve. She comments to me about how my body looks different since I have been seeing Darryl. I’ve lost weight but my chest does seem to be a bit puffy but not buff. I dress up in clothes that I have in the garage. I knew that Darryl would appreciate seeing me fully femmed. Eve lets me borrow some of her make up and it was touching for me to be Diane around her and she commented how I seem happier with more of a bounce in my step being Diane.

I was still nervous going out the hose in the day time especially with neighbors but nothing happens. Eve drives us to Darryl house with me giving directions. We get to his house we have no idea what is going to happen. We go to his front door. He answers and we tell him that we love him and that we need him in our lives. He asks if we are fully submit to him as his slaves. We still had no idea what it really meant but we agree. He tells us to get down on our knees and take out his cock and worship it. Together we sucked our new Master’s cock together. He cums on both of us. He tells us that we are no longer husband and wife in reality but his slaves. He tells us to give our wedding rings to him as a sign of our love and loyalty to him. We pause and look at each other but we do as he says. He then tells Eve that I was to always be referred to as Diane. After that he tells us that we can go to our house and that he would be over later that night and that we need to have a key for house for him. We then drive home in our separate cars with his cum still on our faces.

 

[gingers_sub]

Very Hot story.
Please continue.

 

[MyWifeDatesNow]

Hot story, love to read more!

 

[LadyDiATL]

Hot story

 

[SquirmingSub]

Very interesting story! Looking forward to reading more!

 

[18mDresdF4prom]

This is soooo close to how my own sissy life began, even down to the Gym owner BF for the ex-wife. We should so chat!

Hi, great pic. I femmedSnow much younger, of course but also for a blk master- star of our champ basketball team
Now 34b-29-41. Some Victoria sec bras I need 32C. 5'3 160 lb. I know kind of heavy but I am very strong. A gymnast and diver and swimmer!

Real n legal name now Mary. Love Mary. Ty Diane

 

[cdbritany]

super hot!!!!