Stefanie's Crossdressing Memoirs Vol. 2
December 31st, 2012. New Year's Eve. That was the night that changed my life as a crossdresser. For the past month and a half, I had my new wig and had tried my hand at applying makeup when I would dress up. I was absolutely horrible at it, I had no idea what I was doing. So I kept it simple--lipstick, eyeshadow, mascara. The fact that I didn't use eyeliner (which I love wearing nowadays) should be a testament to how I had no idea what I was doing.
Most of my friends already had plans for New Year's, and were out of town or doing something else. So I found myself alone at my condo that night. That wasn't going to stop me from celebrating in my own way, when night came I started having some drinks and just chilled in front of the tv. That's when I started feeling horny and got the urge to dress up sexy again. No one was around, and it was a cold upstate New York winter night, so I decided to go all out. I got in the shower and shaved everything-legs, arms, you name it, I was totally smooth. I figured that since it was winter, I didn't run the risk of anyone seeing my shaved legs, which at the time I was not ready for my friends to see. After I dried off, I picked out my outfit from my still limited wardrobe. That night, Stefanie would wear purple panties, fishnet tights, a black cami, a white turtle neck sweater, a denim mini skirt, and my black strappy platform sandal high heels. I gravitated towards platforms at the time, despite how freakishly tall they made me, since I was still learning to walk in heels. I will never forget how those fishnets felt when I pulled them up my legs. Once I was all dressed, I went into the bathroom and put on my limited makeup: red lipstick and light blue eyeshadow, as well as some mascara which I still struggled with. I put my wig on and Stefanie had come to life.
I sat down at my desk in my home office with another drink and the nail polish, and proceeded to try painting my nails while watching some cd porn. I reveled in how it felt to be fully dressed up: feet in high heels, legs rubbing each other in fishnets, my sissyhood neatly tucked into my panties, skirt riding up as I moved around, tasting my lipstick and feeling my long hair around my ears and face. I was getting really turned on and as I had more to drink I only got hornier and hornier. That's when I pulled up craigslist.
The bourbon I was drinking and how my outfit made me feel had emboldened me to act on a desire do something I had only watched online and masturbated to for so long--suck a man's cock and taste his cum. I posed and took a few pictures with my digital camera, me bending over showing off my legs and pantied ass, me leaning up against the wall sticking my ass out, I really wanted men to choose my ad on craigslist. I got more and more nervous as I put the pictures on my computer and began typing my ad. To keep myself from chickening out, I kept my ad simple: just a cd offering an nsa blow and go to any guys who didn't get lucky on New Year's. I clicked post ad and I waited. I was so nervous that I had to turn the heat in my condo down and make myself another drink. When I returned to my desk and hit refresh on my email, I could not believe how many responses I already had. My heart started pounding even faster, and I hadn't even replied to any yet. But I was so horny and determined to go through with it. I figured I have to do it at least once to know for sure if I like it.
This was my first experience with how many fakes and flakes there are on CL. And all the dirty talk I did with the guys who responded to my ad about what we would do together only got me even more horny. However, I finally got one response that I knew would be the one. In the course of exchanging 2-3 emails, he was on his way. This was it. I turned the lights real low in my living room and waited. The blinds were closed but everytime I saw headlights going by I jumped up to see if they were pulling into my driveway. Finally, after what felt like an eternity, a car pulled in, turned off the headlights, and a figure got out of the car.
My fishnet pantyhose covered legs trembled in my 5" platform heels as I stood by the door waiting for the doorbell. The bell rang, I opened the door. Since the lights were so low I didn't get the best look at the guy who would give me my first cock in my mouth. He was slim, and shorter than me but that is common since I'm so tall before heels. My fem voice was pretty much non existent so I took his hand and whispered for him to come with me to the couch. At first we sat down next to each other, and I almost instinctively reached to undo his pants. At that moment I realized how cold my hands were, so I slid off the couch onto my knees in front of him, in between his legs, ready to show him what a good little cocksucker I was ready to be.
I leaned in, and slowly wrapped my lips around the head of his cock. At that moment, all I could say to myself was I had done it. I was now officially a crossdressing cocksucker---and I LOVED IT! My nervousness melted away. His cock was already chubby when my slutty lips first wrapped around it, and I relished feeling it swell even more in my mouth as I licked and moved my head up and down. After a few minutes he stood up and I sat down on the couch to continue sucking him. I developed a rhythm and licked and sucked and kissed the tip and all down his shaft. It wasn't long before he came, and I had my second I had done it moment---I had sucked a man's cock and now he was cumming in my mouth! I had tried eating my own cum in the past and wasn't a huge fan, but this was totally different. I loved how it felt when it shot out of his cock and filled my mouth up. I swirled it around for a very brief moment before I swallowed and took his cock out of my mouth and licked up what was left.
I cleaned him up with a wet wipe, and walked him to the door. I meekly and shyly said thank you and he was on his way.
Proud of my accomplishment, in the kitchen I fixed myself another drink when I noticed the clock on the stove. The night was still young! It was only just past midnight, and I knew there were drunk, horny guys out there who would love a New Year's bj. I got back on my computer, emailed my guy another thank you, and started browsing all the new responses I received. I had no idea so many guys in the area wanted their cocks sucked by a crossdresser like me! Unfortunately, I wasn't able to get another guy over that night, but had several contacts that seemed promising for the prospect of a future meet up. Still craving more cum, I ended my night eating my own cum, and while not quite as good as earning the warm salty reward from someone else, it satisfied my inner gurl for a little while.
That night had opened the floodgates for my craigslist adventures, which I hope you'll come back to read more about in Vol. 3 as Stefanie fully embraces dressing up like the little gay crossdressing cocksucker she had become. As now she had finally had her first taste of cock and cum, the next desire had emerged--getting fucked while dressed like a sissy fag. Hope to see you there!
Muah!
xxoo
Stefanie
Most of my friends already had plans for New Year's, and were out of town or doing something else. So I found myself alone at my condo that night. That wasn't going to stop me from celebrating in my own way, when night came I started having some drinks and just chilled in front of the tv. That's when I started feeling horny and got the urge to dress up sexy again. No one was around, and it was a cold upstate New York winter night, so I decided to go all out. I got in the shower and shaved everything-legs, arms, you name it, I was totally smooth. I figured that since it was winter, I didn't run the risk of anyone seeing my shaved legs, which at the time I was not ready for my friends to see. After I dried off, I picked out my outfit from my still limited wardrobe. That night, Stefanie would wear purple panties, fishnet tights, a black cami, a white turtle neck sweater, a denim mini skirt, and my black strappy platform sandal high heels. I gravitated towards platforms at the time, despite how freakishly tall they made me, since I was still learning to walk in heels. I will never forget how those fishnets felt when I pulled them up my legs. Once I was all dressed, I went into the bathroom and put on my limited makeup: red lipstick and light blue eyeshadow, as well as some mascara which I still struggled with. I put my wig on and Stefanie had come to life.
I sat down at my desk in my home office with another drink and the nail polish, and proceeded to try painting my nails while watching some cd porn. I reveled in how it felt to be fully dressed up: feet in high heels, legs rubbing each other in fishnets, my sissyhood neatly tucked into my panties, skirt riding up as I moved around, tasting my lipstick and feeling my long hair around my ears and face. I was getting really turned on and as I had more to drink I only got hornier and hornier. That's when I pulled up craigslist.
The bourbon I was drinking and how my outfit made me feel had emboldened me to act on a desire do something I had only watched online and masturbated to for so long--suck a man's cock and taste his cum. I posed and took a few pictures with my digital camera, me bending over showing off my legs and pantied ass, me leaning up against the wall sticking my ass out, I really wanted men to choose my ad on craigslist. I got more and more nervous as I put the pictures on my computer and began typing my ad. To keep myself from chickening out, I kept my ad simple: just a cd offering an nsa blow and go to any guys who didn't get lucky on New Year's. I clicked post ad and I waited. I was so nervous that I had to turn the heat in my condo down and make myself another drink. When I returned to my desk and hit refresh on my email, I could not believe how many responses I already had. My heart started pounding even faster, and I hadn't even replied to any yet. But I was so horny and determined to go through with it. I figured I have to do it at least once to know for sure if I like it.
This was my first experience with how many fakes and flakes there are on CL. And all the dirty talk I did with the guys who responded to my ad about what we would do together only got me even more horny. However, I finally got one response that I knew would be the one. In the course of exchanging 2-3 emails, he was on his way. This was it. I turned the lights real low in my living room and waited. The blinds were closed but everytime I saw headlights going by I jumped up to see if they were pulling into my driveway. Finally, after what felt like an eternity, a car pulled in, turned off the headlights, and a figure got out of the car.
My fishnet pantyhose covered legs trembled in my 5" platform heels as I stood by the door waiting for the doorbell. The bell rang, I opened the door. Since the lights were so low I didn't get the best look at the guy who would give me my first cock in my mouth. He was slim, and shorter than me but that is common since I'm so tall before heels. My fem voice was pretty much non existent so I took his hand and whispered for him to come with me to the couch. At first we sat down next to each other, and I almost instinctively reached to undo his pants. At that moment I realized how cold my hands were, so I slid off the couch onto my knees in front of him, in between his legs, ready to show him what a good little cocksucker I was ready to be.
I leaned in, and slowly wrapped my lips around the head of his cock. At that moment, all I could say to myself was I had done it. I was now officially a crossdressing cocksucker---and I LOVED IT! My nervousness melted away. His cock was already chubby when my slutty lips first wrapped around it, and I relished feeling it swell even more in my mouth as I licked and moved my head up and down. After a few minutes he stood up and I sat down on the couch to continue sucking him. I developed a rhythm and licked and sucked and kissed the tip and all down his shaft. It wasn't long before he came, and I had my second I had done it moment---I had sucked a man's cock and now he was cumming in my mouth! I had tried eating my own cum in the past and wasn't a huge fan, but this was totally different. I loved how it felt when it shot out of his cock and filled my mouth up. I swirled it around for a very brief moment before I swallowed and took his cock out of my mouth and licked up what was left.
I cleaned him up with a wet wipe, and walked him to the door. I meekly and shyly said thank you and he was on his way.
Proud of my accomplishment, in the kitchen I fixed myself another drink when I noticed the clock on the stove. The night was still young! It was only just past midnight, and I knew there were drunk, horny guys out there who would love a New Year's bj. I got back on my computer, emailed my guy another thank you, and started browsing all the new responses I received. I had no idea so many guys in the area wanted their cocks sucked by a crossdresser like me! Unfortunately, I wasn't able to get another guy over that night, but had several contacts that seemed promising for the prospect of a future meet up. Still craving more cum, I ended my night eating my own cum, and while not quite as good as earning the warm salty reward from someone else, it satisfied my inner gurl for a little while.
That night had opened the floodgates for my craigslist adventures, which I hope you'll come back to read more about in Vol. 3 as Stefanie fully embraces dressing up like the little gay crossdressing cocksucker she had become. As now she had finally had her first taste of cock and cum, the next desire had emerged--getting fucked while dressed like a sissy fag. Hope to see you there!
Muah!
xxoo
Stefanie
7 years ago
