Stefanie's Crossdressing Memoirs Vol. 3
After my New Year's Eve debut as a regular in the m4m/t4m section of craigslist as a crossdressing guy who enjoys sucking cock, my desire to dress up slutty and please others had only gotten stronger and stronger. Over the next few weeks after the new year, any time my roomate was out of town for the weekend, Stefanie would inevitably post on craigslist looking for more cock to suck. I found what I was looking for on most occasions, although I still hadn't met someone that I was comfortable enough with to bend me over and fuck me. That moment would finally come when I started talking to Julie, another crossdresser who I had connected with through a social media site. She was older than I was, but even then I generally preferred people older than me, since I knew they were more likely to be serious about meeting up.
Julie regularly travelled to the city I lived about an hour away from. After emailing back and forth, we agreed to met during her next business trip there. I was thrilled--I had sucked a few cocks already, but they were all blow and go, plus none of them were other gurls, not that it bothered me any. But my crossdressing journey originated with cd porn, so now I was going to get to experience something I always wanted to.
There was a snowstorm the night I was supposed to drive down to Julie's hotel, but I wasn't going to let that stop me. I packed a bag with my girly things, and even had my panties and stockings on underneath my street clothes to make my transformation even faster when I got to the hotel. I was taking it nice and slow on the drive, but all of sudden my truck started fishtailing in the snow! The tires quickly regained traction, but my heart was about at the top of my throat with how scared I was. I almost wrecked in a snowstorm, and I thought to myself when the paramedics would have arrived on the scene they would have found out what I was wearing underneath! I was more scared of being found out that way than actually crashing.
I finally got to the hotel in one piece, and called Julie to let her know I was on my way up. It felt a little weird using my normal voice, but in our emails we talked about how we didn't really have fem voices. Plus we were both turned on by really being men in drag, and not being totally passable was part of the allure of dressing up for us. Even though I dressed up fully, there was something about being clearly a crossdresser that really excited me. I figured it was the humiliation aspect of it all, which I would explore more later in my adventures.
I walked into the lobby with my bag, I was a little nervous that the girl at the front desk would stop me, but I don't think she even looked up as I made my way to the elevator. I was starting to get more nervous. My craigslist crossdressing slut nerves hadn't fully developed yet, so I still got quite a rush from the moments right before a meet up.
Julie left the door open for me so I could go right to the bathroom and get changed. Stefanie emerged from the bathroom and turned the corner into the room to meet Julie face to face. She was fully dressed in a silk top, satin skirt, sheer stockings and black heels. She had a red wig and her makeup was minimal, but nice. She was laying on one of the beds and had been watching some cd porn while she waited for me. I went and sat next to her on the bed and she sat up as we chatted and got acquainted.
She put one arm around me and another on my stocking covered thigh. I told her about my near crash and explained that was why I was a little anxious. Julie was a smoker, and although I normally didn't enjoy cigarettes, I asked her for one and we shared a slim, which I loved. It calmed my nerves a bit, and Julie was very turned on seeing me put that fem cigarette between my bright red lips. We would pass the cigarette back and forth and after it was done we began making out. I loved feeling her lipstick covered lips on mine and our tongues slid back and forth over each other's. My hand found its way up her thigh and I began to rub the growing bulge in her panties.
Julie then laid down on the bed and I moved in between her legs to pull her skirt up, then I moved her panties to the side and put her smooth shaved cock in my eager mouth. I turned my body so she could lift my skirt up and rub my ass. The more vigorously I sucked her cock the more she slapped my ass and squeezed it then began playing with my hole. I melted as soon as she first did that and let out quite a moan. She moved to switch places with me so I laid down on the bed and she moved between my legs. She grabbed a smaller vibrating buttplug from her things and began to lick my hole and gently push the plug into me. She would go back and forth between sucking my cock and licking my hole as she pushed the plug in further and further. I loved how she was gentle with me but firm at the same time. Julie was a top, and in our emails she made it clear that she would be fucking me so I was enjoying how she prepared me for it.
I was finally ready to get pounded in the ass so I flipped over on the bed and pulled my thong off completely. I was on all fours and put my ass in the air and my face down on the mattress. I turned my head to look at Julie and begged her to put her cock in my ass. She slid her panties off and got in position behind me on the bed. She did an amazing job of loosening me up with her tongue and the vibrator because her cock went in with almost no trouble. I felt the head of her cock spread my hole open, and then I could tell once it was all the way in. She squirted some more lube on me and then started pumping back and forth. She held me down and I loved feeling her thighs against the back of my legs. I wrapped my stocking covered legs around hers as she fucked me faster and harder.
Julie said she was getting ready to cum so she pulled out and told me to flip over on the bed. She got off the bed and stood up at the edge of the bed and motioned for me to get close. She started jerking her cock right in front of my face and then she finally squirted a nice thick load of cum onto my face. While I wiped it off my face with my fingers and licked them clean, she started sucking my cock again while I was still laying on the bed. I let her know that I was going to cum, and after I did she moved back towards the front of the bed, got on top of me and spit my cum back into my mouth, then we shared a long, passionate kiss swirling my cum in each other's mouth. She wanted me to swallow which I gladly did, and we laid on the bed for a few minutes with our legs wrapped together, simply enjoying the feeling of dressing up sexy and sharing our cum together.
Sadly, it was getting late and I still had an hour long drive back through the storm to my place. I went to the bathroom to change, although I kept my stockings and panties on. I packed my bag and said my goodbye to Julie. Sadly we would meet up only once more for some steamy crossdressing man on crossdressing man action. However, I had finally been fucked, and fucked good. Julie made me her little bitch and I loved every moment of it.
I hope you check in again for my next post, as I describe more of the pleasures I had and gave to others who were bold enough to meet up!
Muah!
xxoo
-Stefanie
Julie regularly travelled to the city I lived about an hour away from. After emailing back and forth, we agreed to met during her next business trip there. I was thrilled--I had sucked a few cocks already, but they were all blow and go, plus none of them were other gurls, not that it bothered me any. But my crossdressing journey originated with cd porn, so now I was going to get to experience something I always wanted to.
There was a snowstorm the night I was supposed to drive down to Julie's hotel, but I wasn't going to let that stop me. I packed a bag with my girly things, and even had my panties and stockings on underneath my street clothes to make my transformation even faster when I got to the hotel. I was taking it nice and slow on the drive, but all of sudden my truck started fishtailing in the snow! The tires quickly regained traction, but my heart was about at the top of my throat with how scared I was. I almost wrecked in a snowstorm, and I thought to myself when the paramedics would have arrived on the scene they would have found out what I was wearing underneath! I was more scared of being found out that way than actually crashing.
I finally got to the hotel in one piece, and called Julie to let her know I was on my way up. It felt a little weird using my normal voice, but in our emails we talked about how we didn't really have fem voices. Plus we were both turned on by really being men in drag, and not being totally passable was part of the allure of dressing up for us. Even though I dressed up fully, there was something about being clearly a crossdresser that really excited me. I figured it was the humiliation aspect of it all, which I would explore more later in my adventures.
I walked into the lobby with my bag, I was a little nervous that the girl at the front desk would stop me, but I don't think she even looked up as I made my way to the elevator. I was starting to get more nervous. My craigslist crossdressing slut nerves hadn't fully developed yet, so I still got quite a rush from the moments right before a meet up.
Julie left the door open for me so I could go right to the bathroom and get changed. Stefanie emerged from the bathroom and turned the corner into the room to meet Julie face to face. She was fully dressed in a silk top, satin skirt, sheer stockings and black heels. She had a red wig and her makeup was minimal, but nice. She was laying on one of the beds and had been watching some cd porn while she waited for me. I went and sat next to her on the bed and she sat up as we chatted and got acquainted.
She put one arm around me and another on my stocking covered thigh. I told her about my near crash and explained that was why I was a little anxious. Julie was a smoker, and although I normally didn't enjoy cigarettes, I asked her for one and we shared a slim, which I loved. It calmed my nerves a bit, and Julie was very turned on seeing me put that fem cigarette between my bright red lips. We would pass the cigarette back and forth and after it was done we began making out. I loved feeling her lipstick covered lips on mine and our tongues slid back and forth over each other's. My hand found its way up her thigh and I began to rub the growing bulge in her panties.
Julie then laid down on the bed and I moved in between her legs to pull her skirt up, then I moved her panties to the side and put her smooth shaved cock in my eager mouth. I turned my body so she could lift my skirt up and rub my ass. The more vigorously I sucked her cock the more she slapped my ass and squeezed it then began playing with my hole. I melted as soon as she first did that and let out quite a moan. She moved to switch places with me so I laid down on the bed and she moved between my legs. She grabbed a smaller vibrating buttplug from her things and began to lick my hole and gently push the plug into me. She would go back and forth between sucking my cock and licking my hole as she pushed the plug in further and further. I loved how she was gentle with me but firm at the same time. Julie was a top, and in our emails she made it clear that she would be fucking me so I was enjoying how she prepared me for it.
I was finally ready to get pounded in the ass so I flipped over on the bed and pulled my thong off completely. I was on all fours and put my ass in the air and my face down on the mattress. I turned my head to look at Julie and begged her to put her cock in my ass. She slid her panties off and got in position behind me on the bed. She did an amazing job of loosening me up with her tongue and the vibrator because her cock went in with almost no trouble. I felt the head of her cock spread my hole open, and then I could tell once it was all the way in. She squirted some more lube on me and then started pumping back and forth. She held me down and I loved feeling her thighs against the back of my legs. I wrapped my stocking covered legs around hers as she fucked me faster and harder.
Julie said she was getting ready to cum so she pulled out and told me to flip over on the bed. She got off the bed and stood up at the edge of the bed and motioned for me to get close. She started jerking her cock right in front of my face and then she finally squirted a nice thick load of cum onto my face. While I wiped it off my face with my fingers and licked them clean, she started sucking my cock again while I was still laying on the bed. I let her know that I was going to cum, and after I did she moved back towards the front of the bed, got on top of me and spit my cum back into my mouth, then we shared a long, passionate kiss swirling my cum in each other's mouth. She wanted me to swallow which I gladly did, and we laid on the bed for a few minutes with our legs wrapped together, simply enjoying the feeling of dressing up sexy and sharing our cum together.
Sadly, it was getting late and I still had an hour long drive back through the storm to my place. I went to the bathroom to change, although I kept my stockings and panties on. I packed my bag and said my goodbye to Julie. Sadly we would meet up only once more for some steamy crossdressing man on crossdressing man action. However, I had finally been fucked, and fucked good. Julie made me her little bitch and I loved every moment of it.
I hope you check in again for my next post, as I describe more of the pleasures I had and gave to others who were bold enough to meet up!
Muah!
xxoo
-Stefanie
7 年 前
