First time sex as a Woman
My name is Tylynn Reese. I have been crossdressing for since I was in my teens. I stopped every now and then for various reasons, but the urge from deep inside me always calls me back. It is late 2017 when I start crossdressing again and this time it was very different. I was watching a porn video of this beautiful crossdresser being fucked and I felt this feeling like none other before. I realized that I would love to let a man have his way with me. I have been fucking myself with dildos for years and I now was intrigued about having the real thing. One evening I put together some sexy photos and posted them on Craigslist….( I miss that site ). Basically, I wanted to find a date for new years eve and bring in the new year as a woman. I received many replies but only a few stood out. Of the few there was one that made a great impression on me. He was single, 48, 6’1” and had a body type that I was looking for.
Over the next few weeks we flirted and as the new year drew closer I began to get excited that this was really going to happen……. fast forward to new years eve. I had rented a very nice hotel room in Little Rock and got there early so I could get ready and look my best for him. I showered and shaved every part of me to make sure I was silky smooth. I made sure I was extremely clean outside and inside. I have a very feminine look but I am 5’ 11” and very tall in heels. I have small boobs and slim body. By request he wanted a redhead so who was I to argue. I put on a sexy red mini dress and did my makeup to perfection. I put on a bright red wig and finished it all off with a pair of five-inch red high heels. I stood there looking at myself in the mirror and I wanted to fuck me.
Reality hit me as I left the room and headed downstairs to the bar to meet him. I panicked and wanted to just go back to my room. I gathered up my courage and walked into the bar and sat down. About 10 minutes later he walked in and came right over to me. I introduced myself and when he checked me out and smiled I knew right then we were going to have a great time. After talking and setting our boundaries I asked if he would like to cum up to my room and he accepted. We walked in and I closed the door and that is when I realized I was going to have sex and be treated like a lady the whole time. I decided to jump right in. I dropped to my knees before him and took off his belt and pulled down his pants…… his cock was bulging from his shorts…. I pulled his shorts down and there was a huge 8-inch beautiful cock before me. I immediately put it in my mouth. I couldn’t believe I was doing it……I was sucking a cock and he was moaning with pleasure. I could feel my own arousal from deep inside me growing. I felt weak and blissful. I could feel he was close when he stopped and pulled me up and lead me to the bed. I slipped my panties off and got on all fours in front of him…….as he put on a condom I lubed myself up really good. He came in behind me, lifted up my dress and as I looked back at him his cock started slowly to push inside me. I could feel the head of his dick go in with only a slight bit of pain that quickly faded. As he continued entering me I pushed back and I could feel all 8 inches of him inside me. It was a feeling like no other. I was being fucked by this handsome sexy man. His pace picked up and his breathing quickened. His cock was hitting my g-spot with every thrust. I could feel a sensation building from the core of my body. I became lost in the moment not wanting this to end……every time his cock was thrust into me I felt a tension building with every thrust. All of the sudden that tension was released thru my body in wave after wave of pleasure. My legs were weak and trembling. My gurl pussy was contracting hard on his cock and I knew he was close to cumming……his breathing and thrusting became faster and harder and he was holding onto my waist pulling me to him with every deep thrust…..I could feel his cock start to swell as he let out a loud moan and with one last thrust he buried his cock balls deep in me. I could feel his cock throbbing and pulsating as he ejaculated deep inside me….then we both collapsed on the bed kind of giggling about what just happened.
That was my first time and I was hooked. Since then I have realized that I do not have that kind of orgasm with everyone but I have found that if the guy treats me respectful then once I trust him enough to get my mind to clear and be able to get lost in the moment that is when the big one happens.
Thank you for reading
Tylynn Reese
Over the next few weeks we flirted and as the new year drew closer I began to get excited that this was really going to happen……. fast forward to new years eve. I had rented a very nice hotel room in Little Rock and got there early so I could get ready and look my best for him. I showered and shaved every part of me to make sure I was silky smooth. I made sure I was extremely clean outside and inside. I have a very feminine look but I am 5’ 11” and very tall in heels. I have small boobs and slim body. By request he wanted a redhead so who was I to argue. I put on a sexy red mini dress and did my makeup to perfection. I put on a bright red wig and finished it all off with a pair of five-inch red high heels. I stood there looking at myself in the mirror and I wanted to fuck me.
Reality hit me as I left the room and headed downstairs to the bar to meet him. I panicked and wanted to just go back to my room. I gathered up my courage and walked into the bar and sat down. About 10 minutes later he walked in and came right over to me. I introduced myself and when he checked me out and smiled I knew right then we were going to have a great time. After talking and setting our boundaries I asked if he would like to cum up to my room and he accepted. We walked in and I closed the door and that is when I realized I was going to have sex and be treated like a lady the whole time. I decided to jump right in. I dropped to my knees before him and took off his belt and pulled down his pants…… his cock was bulging from his shorts…. I pulled his shorts down and there was a huge 8-inch beautiful cock before me. I immediately put it in my mouth. I couldn’t believe I was doing it……I was sucking a cock and he was moaning with pleasure. I could feel my own arousal from deep inside me growing. I felt weak and blissful. I could feel he was close when he stopped and pulled me up and lead me to the bed. I slipped my panties off and got on all fours in front of him…….as he put on a condom I lubed myself up really good. He came in behind me, lifted up my dress and as I looked back at him his cock started slowly to push inside me. I could feel the head of his dick go in with only a slight bit of pain that quickly faded. As he continued entering me I pushed back and I could feel all 8 inches of him inside me. It was a feeling like no other. I was being fucked by this handsome sexy man. His pace picked up and his breathing quickened. His cock was hitting my g-spot with every thrust. I could feel a sensation building from the core of my body. I became lost in the moment not wanting this to end……every time his cock was thrust into me I felt a tension building with every thrust. All of the sudden that tension was released thru my body in wave after wave of pleasure. My legs were weak and trembling. My gurl pussy was contracting hard on his cock and I knew he was close to cumming……his breathing and thrusting became faster and harder and he was holding onto my waist pulling me to him with every deep thrust…..I could feel his cock start to swell as he let out a loud moan and with one last thrust he buried his cock balls deep in me. I could feel his cock throbbing and pulsating as he ejaculated deep inside me….then we both collapsed on the bed kind of giggling about what just happened.
That was my first time and I was hooked. Since then I have realized that I do not have that kind of orgasm with everyone but I have found that if the guy treats me respectful then once I trust him enough to get my mind to clear and be able to get lost in the moment that is when the big one happens.
Thank you for reading
Tylynn Reese
4 years ago
Brings back memories of my first time