Stefanie's Crossdressing Memoirs Vol. 4
For my readers, I would just like to start with a disclaimer that this particular post doesn't include much sex. This story is more about what I consider a rather significant event that I experienced while exploring my crossdressing lifestyle.
So time passed as I would enjoy dressing up as sexy as possible and posting on craigslist for hookups. As I dressed fully more and more often, I got better at two things: doing my makeup, and giving head (with being told the latter by a few different guys). I had to move from New York to North Carolina for work, which I was actually pretty happy about since I was moving to a bigger city. That meant a more active CL page, and more opportunities for Stefanie to do what she did best ;)
I decided to rent a house when I moved, and it was affordable enough that I did not need a room mate to save some cash. So my dressing up only increased further from there. It was a quiet neighborhood, and really a pretty good spot for hosting my craigslist encounters. Once I was all moved in, I inevitably found myself in my office, all dressed up and posting some freshly snapped pictures on my craigslist ad looking for horny guys to come over and let me get them off.
I quickly learned that one downside to being in a larger city with more people perusing craigslist is the larger number of guys who aren't for real about meeting up. Somehow, this particular night I wasn't able to get anyone to come over for a blowjob. I was a little stunned, there I was, a horny crossdresser just giving away blowjobs and no one would drop by.
It got pretty late, and I accepted that no one was coming over. But then I told myself, if I can't get any guys to come to me, I'll just go to them! I looked up on a gay dating site some areas that were known for anonymous hookups in secluded public areas. One of them was a larger local park with lots a trails and public bathrooms. The other was a lakeside recreation area which a pretty big dirt parking lot and hiking trails. The park was closer, so I decided to go check it out. At this time, it was like 11:30 at night, so I figured there's probably some men hanging out waiting for someone to show up. It then dawned on me that this was my first time in public as Stefanie! I was surprisingly calm for such a big step in my crossdressing adventures. I turned off all the lights inside and outside the house. I realized I didn't have a purse to carry my things like a girl should, so I grabbed what I figured I would need and just put it in the passenger seat of my truck. My first steps outside dressed up were exhilarating. I could feel the breeze on my fishnets, hear my heels clicking on the walkway, and I loved every bit of it. In my mind I could only wonder if any of the neighbors had seen me. I looked at the passenger seat and couldn't help but chuckle at the sight: condoms, lube, baby wipes, lipstick, and my driver's license. I then realized how awkward it was to drive in high heels, and cautiously made my to the park.
It was after midnight when I arrived. The parking lot was empty, which was disappointing but not surprising. I sat in my parked truck for a few minutes and looked around. Seemed like the coast was clear, and then I spotted the bathrooms. I decided that anyone in a men's public bathroom in the park after midnight could only be looking for one thing--after all, I was there, and I knew what I was looking for ;)
I got out of my truck and walked towards the bathrooms. I still couldn't believe I was outside as Stefanie! Yes, it was after midnight, and it was an empty park, but for me it was a huge deal. I made it to the bathroom, and the door was unlocked. I had no idea what I find inside. Would I get to give some anonymous head or get fucked in a bathroom like the slut I strived to be? I was so horny with anticipation. I pushed the door open to just an empty bathroom. Once again, I let my excitement get the best of me. This let down actually emboldened me further--I walked much more bravely back to my truck, almost defiantly as if someone had denied me what I wanted. I looked at the clock on the dashboard and said screw it, I'm going to the lake too. This night isn't ending without putting dick in my mouth!
The lake was about 20-25 minutes away. This was my first time there as well; I didn't know exactly where I was going. I slowed down as I approached the parking lot, and as I turned in, there was a car pulling out. The driver had his window down, and laughed at me and waved his finger in a mocking manner as he pulled out of the parking lot and I pulled in. I had pretty dark tint and my windows were up, and I put the sun visor down for a little extra privacy as I was driving, so I was fairly certain he hadn't seen that I was a man with makeup and a wig on.
Then I saw what he was laughing about. About 50 feet into the parking lot, a police car was making its way towards the exit. My heart stopped. A million thoughts ran through my head all at once. What if I get arrested in drag? Who would pick me up from the station? What would happen to me while I was there and dressed the way I was? I tried to play it cool and slowly drove past the police car towards the back of the parking lot. Needless to say, my plan did not work. The cop waved at me to stop, then shined his searchlight right at my window. I rolled the window down and was blinded by his searchlight right in my face. All I heard was a voice that said, "uh, the place is closed." Absolutely humiliated, all I could mumble out was um ok, I'm leaving right now. He pulled off, and I don't think I ever rolled my window up so fast. I nearly peeled out turning around and getting my butt out of there. During the drive back I was relieved but also filled with shock and guilt and still had feelings something bad would happen to me somehow. I couldn't believe my luck at the time, that the very first time going out dressed up I get stopped by a cop.
In retrospect, I probably shouldn't have been so shocked that I would get stopped by a cop late at night at a public spot with a reputation as a low key spot for men to meet up. In future late night drives (yes, I eventually built up the courage to go out again driving, although I would stay on the roads and not stop anywhere) I observed that those two areas were also known for d**gs and prostitution (and many of the prostitutes were also transvestites, but they usually don't take too kindly to crossdressers who suck cock for free, taking away their business).
As I made my way home that night, I stopped at a red light and knowing my luck there was a night road construction crew working. And they also had the super bright portable stadium lights on. Being the only vehicle at the intersection, I felt like all 20 or so of those men stopped what they were doing to look at me, and they could see me pretty easily.
I finally got home, and only then did I begin to fully calm down. Just for fun, I checked my email since I hadn't deleted my craigslist ad. As suspected, only one or two emails with no pictures and all they said was something along the lines of "sup" or "i'm hard". I ended that night by playing with myself in my lingerie and stockings on my bed. I ate my own cum, and called it a night. While Stefanie may not have had the most successful night, that would not stop me in my journey to dress up for hot encounters.
In my upcoming posts, I'll be detailing my rebounds from this eventful night, hope to see you there.
Muah!
xoxo
-Stefanie
So time passed as I would enjoy dressing up as sexy as possible and posting on craigslist for hookups. As I dressed fully more and more often, I got better at two things: doing my makeup, and giving head (with being told the latter by a few different guys). I had to move from New York to North Carolina for work, which I was actually pretty happy about since I was moving to a bigger city. That meant a more active CL page, and more opportunities for Stefanie to do what she did best ;)
I decided to rent a house when I moved, and it was affordable enough that I did not need a room mate to save some cash. So my dressing up only increased further from there. It was a quiet neighborhood, and really a pretty good spot for hosting my craigslist encounters. Once I was all moved in, I inevitably found myself in my office, all dressed up and posting some freshly snapped pictures on my craigslist ad looking for horny guys to come over and let me get them off.
I quickly learned that one downside to being in a larger city with more people perusing craigslist is the larger number of guys who aren't for real about meeting up. Somehow, this particular night I wasn't able to get anyone to come over for a blowjob. I was a little stunned, there I was, a horny crossdresser just giving away blowjobs and no one would drop by.
It got pretty late, and I accepted that no one was coming over. But then I told myself, if I can't get any guys to come to me, I'll just go to them! I looked up on a gay dating site some areas that were known for anonymous hookups in secluded public areas. One of them was a larger local park with lots a trails and public bathrooms. The other was a lakeside recreation area which a pretty big dirt parking lot and hiking trails. The park was closer, so I decided to go check it out. At this time, it was like 11:30 at night, so I figured there's probably some men hanging out waiting for someone to show up. It then dawned on me that this was my first time in public as Stefanie! I was surprisingly calm for such a big step in my crossdressing adventures. I turned off all the lights inside and outside the house. I realized I didn't have a purse to carry my things like a girl should, so I grabbed what I figured I would need and just put it in the passenger seat of my truck. My first steps outside dressed up were exhilarating. I could feel the breeze on my fishnets, hear my heels clicking on the walkway, and I loved every bit of it. In my mind I could only wonder if any of the neighbors had seen me. I looked at the passenger seat and couldn't help but chuckle at the sight: condoms, lube, baby wipes, lipstick, and my driver's license. I then realized how awkward it was to drive in high heels, and cautiously made my to the park.
It was after midnight when I arrived. The parking lot was empty, which was disappointing but not surprising. I sat in my parked truck for a few minutes and looked around. Seemed like the coast was clear, and then I spotted the bathrooms. I decided that anyone in a men's public bathroom in the park after midnight could only be looking for one thing--after all, I was there, and I knew what I was looking for ;)
I got out of my truck and walked towards the bathrooms. I still couldn't believe I was outside as Stefanie! Yes, it was after midnight, and it was an empty park, but for me it was a huge deal. I made it to the bathroom, and the door was unlocked. I had no idea what I find inside. Would I get to give some anonymous head or get fucked in a bathroom like the slut I strived to be? I was so horny with anticipation. I pushed the door open to just an empty bathroom. Once again, I let my excitement get the best of me. This let down actually emboldened me further--I walked much more bravely back to my truck, almost defiantly as if someone had denied me what I wanted. I looked at the clock on the dashboard and said screw it, I'm going to the lake too. This night isn't ending without putting dick in my mouth!
The lake was about 20-25 minutes away. This was my first time there as well; I didn't know exactly where I was going. I slowed down as I approached the parking lot, and as I turned in, there was a car pulling out. The driver had his window down, and laughed at me and waved his finger in a mocking manner as he pulled out of the parking lot and I pulled in. I had pretty dark tint and my windows were up, and I put the sun visor down for a little extra privacy as I was driving, so I was fairly certain he hadn't seen that I was a man with makeup and a wig on.
Then I saw what he was laughing about. About 50 feet into the parking lot, a police car was making its way towards the exit. My heart stopped. A million thoughts ran through my head all at once. What if I get arrested in drag? Who would pick me up from the station? What would happen to me while I was there and dressed the way I was? I tried to play it cool and slowly drove past the police car towards the back of the parking lot. Needless to say, my plan did not work. The cop waved at me to stop, then shined his searchlight right at my window. I rolled the window down and was blinded by his searchlight right in my face. All I heard was a voice that said, "uh, the place is closed." Absolutely humiliated, all I could mumble out was um ok, I'm leaving right now. He pulled off, and I don't think I ever rolled my window up so fast. I nearly peeled out turning around and getting my butt out of there. During the drive back I was relieved but also filled with shock and guilt and still had feelings something bad would happen to me somehow. I couldn't believe my luck at the time, that the very first time going out dressed up I get stopped by a cop.
In retrospect, I probably shouldn't have been so shocked that I would get stopped by a cop late at night at a public spot with a reputation as a low key spot for men to meet up. In future late night drives (yes, I eventually built up the courage to go out again driving, although I would stay on the roads and not stop anywhere) I observed that those two areas were also known for d**gs and prostitution (and many of the prostitutes were also transvestites, but they usually don't take too kindly to crossdressers who suck cock for free, taking away their business).
As I made my way home that night, I stopped at a red light and knowing my luck there was a night road construction crew working. And they also had the super bright portable stadium lights on. Being the only vehicle at the intersection, I felt like all 20 or so of those men stopped what they were doing to look at me, and they could see me pretty easily.
I finally got home, and only then did I begin to fully calm down. Just for fun, I checked my email since I hadn't deleted my craigslist ad. As suspected, only one or two emails with no pictures and all they said was something along the lines of "sup" or "i'm hard". I ended that night by playing with myself in my lingerie and stockings on my bed. I ate my own cum, and called it a night. While Stefanie may not have had the most successful night, that would not stop me in my journey to dress up for hot encounters.
In my upcoming posts, I'll be detailing my rebounds from this eventful night, hope to see you there.
Muah!
xoxo
-Stefanie
6 years ago
