Meeting My Future Master

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 threw a pair of plaid cotton bikini 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. 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.