Hello,
Brand new here, although I've lurked here off and on for the last few years. Finally wanted to share my experience as first time cross dressing and my encounter since I don't have anyone else to share it with. Not sure how good my writing is so please bare with me.
Anyways, I'm a 24 year-old that has always had a fantasy of being with an older man and having him dress me up and role play that I was the "naughty" daughter that he would introduce me to sex. I've had this fantasy for the last few years but never had a chance or the guts to fulfill it though. For me it was always the idea of the age difference and "role reversal" that did it for me. As far as myself, I'm definitely your average college guy with a girlfriend that no one would suspect as having these fantasies.
After feeling really horny, I made a few ads on some websites and actually didn't have any luck finding anyone. Most of the guys simply wanted to get laid and didn't care to discuss my fantasies or theirs, eventually though I started talking to this guy that seemed to fit me well. He was interested in everything I was and after many long talks I came to the conclusion that he wasn't crazy...
After a lot of talking we agreed to meet up one night at his place and just see what I was comfortable with. Prior to this, I had only messed around with a friend when I was younger but was too scared at the time to really enjoy any of the oral or touching that we had done. I was pretty nervous when I arrived at his house but he was very nice and we had a beer or two. I made it known too him that I wanted him to make the first initiation and before I knew it he was grabbing my ass. My hands started to wonder and before I knew it I was feeling his very hard member through his pants. He couldn't take it for long and removed his pants and sat on the couch. I gladly began sucking him off but was surprised at how little I could fit of him in my mouth, he wasn't long but was very thick. He enjoyed it though and I could tell from his moans that I wasn't that bad. Eventually my pants came off and I gave him a hand job so I could watch him cum, this for whatever reason was really exciting to me since I knew that I had caused that from him. After he came, he took me in his mouth and told me to cum and I gladly did. He asked if I was ready to fuck him and I said "no" due too still being nervous and it was already getting late.
Continued in next post... Not sure how much I can write.
Brand new here, although I've lurked here off and on for the last few years. Finally wanted to share my experience as first time cross dressing and my encounter since I don't have anyone else to share it with. Not sure how good my writing is so please bare with me.
Anyways, I'm a 24 year-old that has always had a fantasy of being with an older man and having him dress me up and role play that I was the "naughty" daughter that he would introduce me to sex. I've had this fantasy for the last few years but never had a chance or the guts to fulfill it though. For me it was always the idea of the age difference and "role reversal" that did it for me. As far as myself, I'm definitely your average college guy with a girlfriend that no one would suspect as having these fantasies.
After feeling really horny, I made a few ads on some websites and actually didn't have any luck finding anyone. Most of the guys simply wanted to get laid and didn't care to discuss my fantasies or theirs, eventually though I started talking to this guy that seemed to fit me well. He was interested in everything I was and after many long talks I came to the conclusion that he wasn't crazy...
After a lot of talking we agreed to meet up one night at his place and just see what I was comfortable with. Prior to this, I had only messed around with a friend when I was younger but was too scared at the time to really enjoy any of the oral or touching that we had done. I was pretty nervous when I arrived at his house but he was very nice and we had a beer or two. I made it known too him that I wanted him to make the first initiation and before I knew it he was grabbing my ass. My hands started to wonder and before I knew it I was feeling his very hard member through his pants. He couldn't take it for long and removed his pants and sat on the couch. I gladly began sucking him off but was surprised at how little I could fit of him in my mouth, he wasn't long but was very thick. He enjoyed it though and I could tell from his moans that I wasn't that bad. Eventually my pants came off and I gave him a hand job so I could watch him cum, this for whatever reason was really exciting to me since I knew that I had caused that from him. After he came, he took me in his mouth and told me to cum and I gladly did. He asked if I was ready to fuck him and I said "no" due too still being nervous and it was already getting late.
Continued in next post... Not sure how much I can write.