Meeting My Future Master

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.

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.

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 exposing 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 expose 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.

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.