My first time with a transvestite and my first gay
First of thanks for reading my story!
Second of course this isn't my first sexual experience but it was my frist with a transvestite/male
It was 5 years ago, i found her on a sex contact website. I kept looking at her profile for months, building up the courage to contact her. I finally did no answer. I hung up the phone my heart pounding out of my chest, i felt disappointed. I took it as a sign that it wasn't meant to be. However i decided to give one more try later that afternoon. She picked up, i was kinda startled. She had a nice voice for a transvestite not that i knew what that was supposed to sound like, but i could hear she was making an effort not to sound like a man. I told her i wanted a date with her and it would be my first time with a . There where so many options and i mean what she was willing to do.
As this was my first time you'd think i would stick to the whole kissing and a blowjob routine. But if you want something why not go all the way, so when she asked me what i wanted to do i said i want an 2 hour date, i want to kiss and French kiss you, i want a blowjob and i want to give you one, i want to fuck you and i want to be fucked (All safe sex of course!).
She asked me again if this was my first time i told her yes this is my first time with a transvestite and it's also my first experience with a man. So after agreeing to all the sexual acts we were gonna enjoy, we set a date and a time for the day after. I had to call her on the day to receive the adress and confirm I was serious about it. We met on the parking lot at her place, she was standing outside wearing a extremely sexy outfit! A sexy black latex dress, which showed off her incredibly long leggs. She also wore some beautiful black lace stockings and a pair of black super high heeled pumps. She had lovely long blond natural hair (real hair not a wig). And her make-up was really nice! She was also very clean. Just like me!. So we greeted each other and she invited me in. I was so nervous! But that soon changed, she offered me something to drink and we sat down on the couch. Once again she asked me if I wanted to do everything I spoke of on the phone. I didn’t hesitate and said yes I would.
I had to clean my anus of course and give it a good enema (also my first enema btw). After cleaning myself. I sat back down on the couch, I asked if we could kiss, she said yes and leaned in. Now bear in mind I had never kissed a transvestite/guy before I was shaking but it soon felt really good. We switched it up to a French kiss it was so hot. After that she took me to a large bed. We kissed some more and I felt her beautiful body as she felt mine. She had a lovely ass and a super tight body!. She started stroking my already hard cock and then she started sucking me off. I could barely contain myself. I kept feeling around. And my fingers moved over her asshole, forward to her balls. It was a strange experience but it felt good so I kept going and started stroking her dick. Wow just wow! I felt it growing in my hand, not my dick but hers it was a awesome feeling. I asked her if I could suck it.
I had never ever sucked a dick before, I had seen it of course and I had fantasized about it, but actually doing it hadn’t even crossed my mind. This was really going to happen. I took her dick in my hand stroking it until It was semi hard. I moved my lips closer and I went for it. Slowly moving my lips around the tip and letting it slide in my mouth. Taking it slow and enjoying every second of it. Slowly taking it in deeper including her shaft. It was amazing feeling her dick grow in my mouth just like it did in my hand earlier. I could feel the blood pumping in her cock as I started sucking It more and more, taking it deeper and deeper all the way to her balls. And going faster and faster.
After is felt I was done and she sucked me and kissed me some more I felt is was time to take it to the next level. I was ready to lose my anal virginity…
And boy o boy that was something…I had never even fingered myself so I was in for quite a experience. She knew I had never done anything so she told me she had to prepare my virgin hole.
She put some spit on my virgin hole and her fingers and she slowly and softly put one of her fingers in my asshole. It felt strange and unfamiliar. It was felt kinda rough at first but that was only the beginning. She put 2 more fingers in 3 fingers were in my ass. It kinda hurt. Then she told me to bend over on my knees and put my ass up. She got behind me and slowly let her dick rest against my asshole. She then told me to relax and she pushed in the tip of her dick, it was painful but I knew it was gonna hurt at first. It was only when she put her entire dick in it started to feel less painful only. Only when she pulled back it hurt, my asshole clearly wasn’t used to that sensation.
After doing that slowly she started fucking me harder and faster, I moaned and yelled with pain and pleasure it was a magnificent experience!
Now it was my turn, I had fuck women before but this was my first anal experience, yeah I know another first, I crossed a lot off my bucket list that evening! I got behind her and I grabbed her dick and balls, and her side when I started to fuck her beautiful asshole! It was so soft and tight! It felt so good I fucked her so hard she even came. She told me that hardly ever happened. I took her word for it. After that she finished me off by hand she rubbed the cum over my chest and we ended with some kissing.
She took a shower and so did I. After we kissed some more and then it was time for me to leave.
I never thought I would do something like that ever, never in my wildest dreams but boy am I glad I did. She was so kind and sweet about everything I’m forever grateful to her and I will never ever forget this!
Thanks for reading my story! I hope you enjoyed it, if you are thinking about doing something like this, don’t let your doubts stop you, just remember safety first and if it doesn’t feel right just stop.
If you want to ask me anything go ahead, or just leave a nice comment or something.
Love Michelle xxx
Second of course this isn't my first sexual experience but it was my frist with a transvestite/male
It was 5 years ago, i found her on a sex contact website. I kept looking at her profile for months, building up the courage to contact her. I finally did no answer. I hung up the phone my heart pounding out of my chest, i felt disappointed. I took it as a sign that it wasn't meant to be. However i decided to give one more try later that afternoon. She picked up, i was kinda startled. She had a nice voice for a transvestite not that i knew what that was supposed to sound like, but i could hear she was making an effort not to sound like a man. I told her i wanted a date with her and it would be my first time with a . There where so many options and i mean what she was willing to do.
As this was my first time you'd think i would stick to the whole kissing and a blowjob routine. But if you want something why not go all the way, so when she asked me what i wanted to do i said i want an 2 hour date, i want to kiss and French kiss you, i want a blowjob and i want to give you one, i want to fuck you and i want to be fucked (All safe sex of course!).
She asked me again if this was my first time i told her yes this is my first time with a transvestite and it's also my first experience with a man. So after agreeing to all the sexual acts we were gonna enjoy, we set a date and a time for the day after. I had to call her on the day to receive the adress and confirm I was serious about it. We met on the parking lot at her place, she was standing outside wearing a extremely sexy outfit! A sexy black latex dress, which showed off her incredibly long leggs. She also wore some beautiful black lace stockings and a pair of black super high heeled pumps. She had lovely long blond natural hair (real hair not a wig). And her make-up was really nice! She was also very clean. Just like me!. So we greeted each other and she invited me in. I was so nervous! But that soon changed, she offered me something to drink and we sat down on the couch. Once again she asked me if I wanted to do everything I spoke of on the phone. I didn’t hesitate and said yes I would.
I had to clean my anus of course and give it a good enema (also my first enema btw). After cleaning myself. I sat back down on the couch, I asked if we could kiss, she said yes and leaned in. Now bear in mind I had never kissed a transvestite/guy before I was shaking but it soon felt really good. We switched it up to a French kiss it was so hot. After that she took me to a large bed. We kissed some more and I felt her beautiful body as she felt mine. She had a lovely ass and a super tight body!. She started stroking my already hard cock and then she started sucking me off. I could barely contain myself. I kept feeling around. And my fingers moved over her asshole, forward to her balls. It was a strange experience but it felt good so I kept going and started stroking her dick. Wow just wow! I felt it growing in my hand, not my dick but hers it was a awesome feeling. I asked her if I could suck it.
I had never ever sucked a dick before, I had seen it of course and I had fantasized about it, but actually doing it hadn’t even crossed my mind. This was really going to happen. I took her dick in my hand stroking it until It was semi hard. I moved my lips closer and I went for it. Slowly moving my lips around the tip and letting it slide in my mouth. Taking it slow and enjoying every second of it. Slowly taking it in deeper including her shaft. It was amazing feeling her dick grow in my mouth just like it did in my hand earlier. I could feel the blood pumping in her cock as I started sucking It more and more, taking it deeper and deeper all the way to her balls. And going faster and faster.
After is felt I was done and she sucked me and kissed me some more I felt is was time to take it to the next level. I was ready to lose my anal virginity…
And boy o boy that was something…I had never even fingered myself so I was in for quite a experience. She knew I had never done anything so she told me she had to prepare my virgin hole.
She put some spit on my virgin hole and her fingers and she slowly and softly put one of her fingers in my asshole. It felt strange and unfamiliar. It was felt kinda rough at first but that was only the beginning. She put 2 more fingers in 3 fingers were in my ass. It kinda hurt. Then she told me to bend over on my knees and put my ass up. She got behind me and slowly let her dick rest against my asshole. She then told me to relax and she pushed in the tip of her dick, it was painful but I knew it was gonna hurt at first. It was only when she put her entire dick in it started to feel less painful only. Only when she pulled back it hurt, my asshole clearly wasn’t used to that sensation.
After doing that slowly she started fucking me harder and faster, I moaned and yelled with pain and pleasure it was a magnificent experience!
Now it was my turn, I had fuck women before but this was my first anal experience, yeah I know another first, I crossed a lot off my bucket list that evening! I got behind her and I grabbed her dick and balls, and her side when I started to fuck her beautiful asshole! It was so soft and tight! It felt so good I fucked her so hard she even came. She told me that hardly ever happened. I took her word for it. After that she finished me off by hand she rubbed the cum over my chest and we ended with some kissing.
She took a shower and so did I. After we kissed some more and then it was time for me to leave.
I never thought I would do something like that ever, never in my wildest dreams but boy am I glad I did. She was so kind and sweet about everything I’m forever grateful to her and I will never ever forget this!
Thanks for reading my story! I hope you enjoyed it, if you are thinking about doing something like this, don’t let your doubts stop you, just remember safety first and if it doesn’t feel right just stop.
If you want to ask me anything go ahead, or just leave a nice comment or something.
Love Michelle xxx
8年前
