The Story of Stephanie (Part 8)
Here I was, single, living alone and loving life. I liked to make sure I had a good time as much as possible, cos I knew one day I'd settle down. But I made sure I took full advantage of my single life. One Saturday night, I was out with a friend for a few drinks. We decided to head to a club. We went to an 80s club, which personally speaking is a stuff of nightmares for me due to the fact I'm more into rock and indie music. But I went anyway. We were there about 30 minutes and already I was bored. I'd already had 2 drinks and was about to order my 3rd. I started talking to these 2 girls at the bar. I introduced myself. They introduced themselves back. Alicia and Jennifer. They were both a couple of years older than me. I got chatting to Alicia, who I could kinda tell fancied me. She was really nice, but I wasn't sure I fancied her. But, I was bored so I decided to just go along with it. As we were chatting, we started getting pretty flirty. She asked me if I wanted to dance, so I did. We were on the dance floor no more than a minute when she grabbed me and kissed me. As the song was finishing we went back to our friends. I was actually turned on by her. She was a big girl. Not fat, but curvy, in all the right places. She was taller than me too, her boobs were almost at eye level for me. And they were big. I loved them. She was wearing a black dress, tights and heels. I was definitely interested now! A few more dances and a few more snogs later she said what I'd hoped she'd say. "Take me to your place and fuck me!" A bit forward, but fuck it. So I let my friend know I was leaving and we went outside and got a taxi.
She was all over me in the taxi. Thank god I only lived about 10 mins from the club. We were quickly at my flat and inside. Instantly stripped and kissing passionately. In the hallway, I turned her around, bent her over against the wall, pulled her tights down and fucked her. It was amazing. We had sex several times that night. In the hallway, the living room and eventually the bedroom. We were exhausted. We fell asleep for a while, but she woke up in a panic as she saw it was starting to get light outside. She had to make a call. About 10 minutes later she returned. "Everything ok?" I asked. "I hope so." She said. "I have something to confess. I'm sorry, but I'm married with 2 k**s!" Holy shit! This wasn't good at all! I was actually gutted by this. I always said I'd never do something like this. I was having an affair with a married woman. I was the other man. I was the guy who just a couple of years previous had torn my own life apart. All I could think about was how I felt then when I found out about my ex fiancée having an affair. I was devastated. Almost suicidal. I didn't want to be the guy who made someone feel that way. She was crying, apologising like mad. I actually started to feel sorry for her. She was telling me how unhappy she was. How her husband was controlling and sometimes verbally abusive towards her. She didn't love him anymore. I told her though, that I wasn't comfortable with this. I mean, what if he found out and came looking for me. I'd be dead! I had to get my head around this. But she was amazing. The sex was unreal! I actually really liked her. And she really liked me too. She said she had to go. So I called her a taxi. She asked if she could see me again. I wasn't sure, but I told her to keep in touch. She had my number.
After she left I was exhausted. I had to sleep. But my mind was racing. Alicia was texting me from the taxi. Apologising and saying she'd understand if I didn't want to see her again. But I felt like I did. I felt like I needed to see her again. I told her to just go home and be with her k**s. I needed sleep. I told her if she still felt the same after a few days, then we could talk about it. Later that day, after a few hours sleep, I woke up to find a text from Alicia. She felt guilty, but said last night was amazing. We'd both sobered up by now. She said she knew for sure that she wanted to see me again. I wanted to see her too. Despite being married and knowing it was wrong, I wanted to see her too. So I said ok. I agreed to see this married mother of 2 again. What the hell was I playing at? I knew it was wrong, but it excited the life out of me. I knew if I was to see her again, it would need to be when she was free. I knew it wouldn't be easy. She had to make excuses. But we arranged to meet at my flat on the Wednesday night. She told her husband she'd be at a friends house. I couldn't wait.
We texted each other a lot over the next few days. Basically getting to know each other a bit more. She was funny. I like someone who can make me laugh. She was also very flirtatious and suggestive. Our texts were getting rather raunchy. I told her I liked a girl in sexy lingerie, especially stockings. A few minutes later, out of the blue, I got a picture message from Alicia. There she was, fully naked apart from black stockings, heels and a smile. "Like this?" She said. Oh yes, exactly like that! I wanted her now. The married thing was out of my head now. I just wanted her. Wednesday night came. I could not wait to see her. I knew I was in for a treat! I saw her driving into the street. She got out the car wearing a long black jacket. I could catch a glimpse of her nylon covered legs. I was horny. She got to my door and I opened it. There and then, she pulled open her jacket. She was wearing a black bra, thong, suspender belt and stockings with heels. Nothing else! My jaw dropped! I pulled her inside and straight into the bedroom. It was amazing, wrong, but oh so right. Afterwards, we lay there talking. We got on to fantasies. I told her the usual things a guy would say. Threesomes, outdoor sex and surprisingly something I'd never done with a girl, anal! She had never tried that either, but said she'd like to try it with me. As time was getting on, we decided we'd try that next time. I was already excited.
I had a day off work coming up. She said she'd come and see me that morning once the k**s were in school. I couldn't wait. I was gonna do what no girl before had ever let me do before. Plus, I was gonna get to feel what it was like for Kevin when he fucked me! This was mind-blowing! I was living in a fantasy world! She arrived, looking a lot more conservative than the last time. We kissed and made our way to the bedroom. As things were starting to get a bit hot and heavy, she stopped me and told me she had something to show me. She took off her blouse, then her trousers. She was wearing a black fishnet bodystocking. So sexy. But that wasn't it. She turned around and bent over. There it was! A black butt plug! I was loving this. She'd clearly done her research. She told me to help her take it out. I slowly done as she said. Her ass was very inviting. I told her I wanted to work up to it, so we started having just normal sex. Then she said it. The 4 words every man wants to here. "Please fuck my ass!" You don't have to tell me twice. I got up and bent her over the bed and got into position. I remembered how I felt the first time, I knew it would hurt. So I took my time, and sure enough. She told me to stop as it was sore. I did, but she said to give it a minute and try again. So I waited. I was rock hard by now. I just wanted to grab her a fuck her senseless. We tired again. Again, going nice and slow. This time I went all the way and I was in. I started off nice and slow. Building up the pace a little. I asked her if she was ok. She was enjoying this. She told me to fuck her harder. It wasn't long before I could feel myself ready to cum. And bang. I came so hard. It was intense. We both dropped to our knees on the floor. That was amazing.
Now I bet your wondering, what has this got to do with my journey as Stephanie? Well as I said earlier, Alicia and I had discussed our fantasies. One I'd kept from her, was Stephanie, and that I'd always wanted to be Stephanie whilst with a real woman. I didn't think any woman would ever accept that part of me. But one night I got thinking to myself. I've really got nothing to lose here. This woman had already told me that for the sake of her c***dren, she wouldn't leave her husband. I was fine with this. I knew our relationship was purely physical. I knew if I told her about Stephanie, she couldn't do or say anything to anybody. She couldn't let slip about our relationship. She'd get found out just as much as me! So I done it. I text her and told her straight. "Alicia, I have something I need to tell you. I hope you understand. I'm a crossdresser. I've been doing it for years and I've even had sex with a man! I'd understand if you think this is weird and don't want to see me again, but I felt I had to tell you!" Surprisingly, her response was positive. She actually thought it was brilliant. That night I told her all about Stephanie. I even sent her a picture. She said I was gorgeous. She wanted to meet Stephanie. Wow, I thought to myself. So we agreed. We arranged to meet up for a drink so we can talk. Almost a date kinda situation. Risky, but we felt we needed a change of scenery. As we sat in the bar chatting, I told her everything. From my first time dressing right through to meeting Kevin. She was intrigued and was dying to meet Stephanie. So we decided it was time to head back to mine. When we got there, I told her to go wait in the living room while I went and got ready. I got in the room and picked out my favourite lingerie and dress. Quickly done my makeup and fixed my wig on. I walked into the living room and it was time for Alicia to meet Stephanie. She loved what she saw. She came and gave me a massive hug and kissed me. Lipstick on lipstick. My breast forms pressing against her big breasts. This was unreal. We got into the living room and sat on the couch to talk. She asked me to take off my dress and show me what I had on underneath. She was very impressed, and jealous that my lingerie was better than hers! She stood up and removed her dress too. She was wearing a bra, thong, suspender belt and stockings. Stunning! We started kissing, and soon enough we were having sex on my couch. My biggest fantasy was coming true there and then. Even having more anal sex. It was better this time. She loved it.
I had to stop myself falling in love with this woman. I knew deep down this was all wrong. But she accepted me for me. And more to the point, she accepted Stephanie. Our affair would continue for another 6 weeks until one night things took a turn. I was out with my friend. I was texting Alicia back and forth. She said what I hoped she wouldn't. She loved me! She was going to tell her husband about me. This was wrong! And certainly not part of the plan. I panicked. She couldn't do this! Then the feelings that I felt at the start came back. I started thinking about her husband. He will be heartbroken. He'll feel the way I'd once felt. I couldn't do that to him. I told Alicia that if she loved me, she wouldn't tell her husband. She didn't listen and told him everything. I was devastated. I told Alicia that we'd gone too far. We shouldn't have ever let it get to this. I didn't want to be the reason for a family breaking up. I told her it was over between us. She had to work on her marriage. Reluctantly she agreed. Her husband was angry and upset. I could understand that feeling. But Alicia agreed to stop seeing me, cut all ties and work on her marriage. After that night, I never heard from Alicia again.
I'll never forget her. She gave me so much in such a short period of time. And I certainly learned a lesson or two!
To be continued......
She was all over me in the taxi. Thank god I only lived about 10 mins from the club. We were quickly at my flat and inside. Instantly stripped and kissing passionately. In the hallway, I turned her around, bent her over against the wall, pulled her tights down and fucked her. It was amazing. We had sex several times that night. In the hallway, the living room and eventually the bedroom. We were exhausted. We fell asleep for a while, but she woke up in a panic as she saw it was starting to get light outside. She had to make a call. About 10 minutes later she returned. "Everything ok?" I asked. "I hope so." She said. "I have something to confess. I'm sorry, but I'm married with 2 k**s!" Holy shit! This wasn't good at all! I was actually gutted by this. I always said I'd never do something like this. I was having an affair with a married woman. I was the other man. I was the guy who just a couple of years previous had torn my own life apart. All I could think about was how I felt then when I found out about my ex fiancée having an affair. I was devastated. Almost suicidal. I didn't want to be the guy who made someone feel that way. She was crying, apologising like mad. I actually started to feel sorry for her. She was telling me how unhappy she was. How her husband was controlling and sometimes verbally abusive towards her. She didn't love him anymore. I told her though, that I wasn't comfortable with this. I mean, what if he found out and came looking for me. I'd be dead! I had to get my head around this. But she was amazing. The sex was unreal! I actually really liked her. And she really liked me too. She said she had to go. So I called her a taxi. She asked if she could see me again. I wasn't sure, but I told her to keep in touch. She had my number.
After she left I was exhausted. I had to sleep. But my mind was racing. Alicia was texting me from the taxi. Apologising and saying she'd understand if I didn't want to see her again. But I felt like I did. I felt like I needed to see her again. I told her to just go home and be with her k**s. I needed sleep. I told her if she still felt the same after a few days, then we could talk about it. Later that day, after a few hours sleep, I woke up to find a text from Alicia. She felt guilty, but said last night was amazing. We'd both sobered up by now. She said she knew for sure that she wanted to see me again. I wanted to see her too. Despite being married and knowing it was wrong, I wanted to see her too. So I said ok. I agreed to see this married mother of 2 again. What the hell was I playing at? I knew it was wrong, but it excited the life out of me. I knew if I was to see her again, it would need to be when she was free. I knew it wouldn't be easy. She had to make excuses. But we arranged to meet at my flat on the Wednesday night. She told her husband she'd be at a friends house. I couldn't wait.
We texted each other a lot over the next few days. Basically getting to know each other a bit more. She was funny. I like someone who can make me laugh. She was also very flirtatious and suggestive. Our texts were getting rather raunchy. I told her I liked a girl in sexy lingerie, especially stockings. A few minutes later, out of the blue, I got a picture message from Alicia. There she was, fully naked apart from black stockings, heels and a smile. "Like this?" She said. Oh yes, exactly like that! I wanted her now. The married thing was out of my head now. I just wanted her. Wednesday night came. I could not wait to see her. I knew I was in for a treat! I saw her driving into the street. She got out the car wearing a long black jacket. I could catch a glimpse of her nylon covered legs. I was horny. She got to my door and I opened it. There and then, she pulled open her jacket. She was wearing a black bra, thong, suspender belt and stockings with heels. Nothing else! My jaw dropped! I pulled her inside and straight into the bedroom. It was amazing, wrong, but oh so right. Afterwards, we lay there talking. We got on to fantasies. I told her the usual things a guy would say. Threesomes, outdoor sex and surprisingly something I'd never done with a girl, anal! She had never tried that either, but said she'd like to try it with me. As time was getting on, we decided we'd try that next time. I was already excited.
I had a day off work coming up. She said she'd come and see me that morning once the k**s were in school. I couldn't wait. I was gonna do what no girl before had ever let me do before. Plus, I was gonna get to feel what it was like for Kevin when he fucked me! This was mind-blowing! I was living in a fantasy world! She arrived, looking a lot more conservative than the last time. We kissed and made our way to the bedroom. As things were starting to get a bit hot and heavy, she stopped me and told me she had something to show me. She took off her blouse, then her trousers. She was wearing a black fishnet bodystocking. So sexy. But that wasn't it. She turned around and bent over. There it was! A black butt plug! I was loving this. She'd clearly done her research. She told me to help her take it out. I slowly done as she said. Her ass was very inviting. I told her I wanted to work up to it, so we started having just normal sex. Then she said it. The 4 words every man wants to here. "Please fuck my ass!" You don't have to tell me twice. I got up and bent her over the bed and got into position. I remembered how I felt the first time, I knew it would hurt. So I took my time, and sure enough. She told me to stop as it was sore. I did, but she said to give it a minute and try again. So I waited. I was rock hard by now. I just wanted to grab her a fuck her senseless. We tired again. Again, going nice and slow. This time I went all the way and I was in. I started off nice and slow. Building up the pace a little. I asked her if she was ok. She was enjoying this. She told me to fuck her harder. It wasn't long before I could feel myself ready to cum. And bang. I came so hard. It was intense. We both dropped to our knees on the floor. That was amazing.
Now I bet your wondering, what has this got to do with my journey as Stephanie? Well as I said earlier, Alicia and I had discussed our fantasies. One I'd kept from her, was Stephanie, and that I'd always wanted to be Stephanie whilst with a real woman. I didn't think any woman would ever accept that part of me. But one night I got thinking to myself. I've really got nothing to lose here. This woman had already told me that for the sake of her c***dren, she wouldn't leave her husband. I was fine with this. I knew our relationship was purely physical. I knew if I told her about Stephanie, she couldn't do or say anything to anybody. She couldn't let slip about our relationship. She'd get found out just as much as me! So I done it. I text her and told her straight. "Alicia, I have something I need to tell you. I hope you understand. I'm a crossdresser. I've been doing it for years and I've even had sex with a man! I'd understand if you think this is weird and don't want to see me again, but I felt I had to tell you!" Surprisingly, her response was positive. She actually thought it was brilliant. That night I told her all about Stephanie. I even sent her a picture. She said I was gorgeous. She wanted to meet Stephanie. Wow, I thought to myself. So we agreed. We arranged to meet up for a drink so we can talk. Almost a date kinda situation. Risky, but we felt we needed a change of scenery. As we sat in the bar chatting, I told her everything. From my first time dressing right through to meeting Kevin. She was intrigued and was dying to meet Stephanie. So we decided it was time to head back to mine. When we got there, I told her to go wait in the living room while I went and got ready. I got in the room and picked out my favourite lingerie and dress. Quickly done my makeup and fixed my wig on. I walked into the living room and it was time for Alicia to meet Stephanie. She loved what she saw. She came and gave me a massive hug and kissed me. Lipstick on lipstick. My breast forms pressing against her big breasts. This was unreal. We got into the living room and sat on the couch to talk. She asked me to take off my dress and show me what I had on underneath. She was very impressed, and jealous that my lingerie was better than hers! She stood up and removed her dress too. She was wearing a bra, thong, suspender belt and stockings. Stunning! We started kissing, and soon enough we were having sex on my couch. My biggest fantasy was coming true there and then. Even having more anal sex. It was better this time. She loved it.
I had to stop myself falling in love with this woman. I knew deep down this was all wrong. But she accepted me for me. And more to the point, she accepted Stephanie. Our affair would continue for another 6 weeks until one night things took a turn. I was out with my friend. I was texting Alicia back and forth. She said what I hoped she wouldn't. She loved me! She was going to tell her husband about me. This was wrong! And certainly not part of the plan. I panicked. She couldn't do this! Then the feelings that I felt at the start came back. I started thinking about her husband. He will be heartbroken. He'll feel the way I'd once felt. I couldn't do that to him. I told Alicia that if she loved me, she wouldn't tell her husband. She didn't listen and told him everything. I was devastated. I told Alicia that we'd gone too far. We shouldn't have ever let it get to this. I didn't want to be the reason for a family breaking up. I told her it was over between us. She had to work on her marriage. Reluctantly she agreed. Her husband was angry and upset. I could understand that feeling. But Alicia agreed to stop seeing me, cut all ties and work on her marriage. After that night, I never heard from Alicia again.
I'll never forget her. She gave me so much in such a short period of time. And I certainly learned a lesson or two!
To be continued......
5 years ago
