14/15 March, 2020
I had spent that Saturday afternoon shopping. I had gone out in full “girl mode”, wearing a scandalously short dress and 5.5” high heeled wedge sandals. The dress was semi-sheer, so my red panties could be easily seen beneath it. I enjoyed moving about the store hoping that men were looking at me, checking me out, fantasizing about doing dirty, nasty, sexual things with me. Of course, nothing happened, but I had fun nonetheless, and I was horny and ready for more fun when I got home. I spent the rest of the evening/night playing dress-up in my room, trying on numerous different outfits, chatting with admirers on social media, and snapping some photos. It was well after midnight when I started thinking about stripping off the makeup and heading to bed, but I was so horny that I decided to do what I often do at the end of a night in drag when I simply want one more thrill before calling it a night. I decided to go outside for a walk. I put on an orange, form fitting, floral print top, a super short green miniskirt, tan pantyhose and another pair of 5.5” high wedge sandals. I checked the mirror and when I decided that I looked suitably slutty, I grabbed my purse and headed out and walked to the nearest major street. For me, late night walks are best on a major street because they are more likely to have some traffic on them even at that late hour. The point is to be seen by passersby. It’s ALL about being seen. :)
I think it was around 3:30 AM. I was strolling down the block enjoying the thrill I get whenever a car drives past, so I was surprised and slightly panicked when a car approaching from behind, DIDN’T pass. It slowed down until it had pulled up right next to me. I was relieved when I saw that it wasn’t a cop. The guy in the car asked me if I wanted a ride. I thought about it for a few moments and then accepted. I guess it was the “adventurous slut” in me that wanted to see where this would lead, winning out over the “cautious gurl” in me who wanted to turn and run home. That should be a pretty good indicator of just how horny I was that night.
I climbed into the passenger seat and settled in. He said he was on his way home from work and told me how hot he thought I looked. I thanked him for the compliment, and without missing a beat he said “Would you suck my cock if I gave you $20?”
My mind raced as I mulled it over. I had sucked the cock of a stranger who picked me up on the street before, but not for money. If I accepted, it would mean that I’m a whore. For real! Like, an honest to goodness money-for-sex whore. I would be lying if I said that I hadn’t thought about trying prostitution before. Actually, I had thought about it a lot. It was never out of a need for money. It was all about the thrill of it. The depravity of doing it just for kicks made it an even bigger turn on for me. But fear of going to jail and fear for my physical well being had always kept me from pursuing prostitution outside of a role play situation. So, there I was with the opportunity to fulfill one of my most debased sexual fantasies and all I had to say was “yes”. I actually didn’t mull it over for very long. I think only a few moments passed before I heard the words “Sure, I can do that.” coming out of my mouth.
I felt almost in a daze as he pulled his wallet out, removed a twenty, and handed it over. I tucked the money into my purse as he turned the car down a side street. Another turn and we were on a street suitably quiet and dark. He didn’t stop the car, though. He simply slowed to an idle and as we rolled slowly down the street, he unzipped his pants and pulled out his cock.
I was happy to see it was on the larger side. I set my purse on the floor and leaned over into his lap and took a complete stranger’s cock into my mouth. I think it took less than a minute of me sucking him for his cock to become fully erect. He was around 7” I would guess. I was very pleased with his thickness, too. A nice mouthful, but not a jaw breaker. LOL
I massaged his balls as I bobbed up and down on his big dick. Having been paid, I felt a little extra pressure to make it a good experience for him. Like, I was REALLY hoping that I was gonna be able to make him cum. He was talking dirty to me a little bit, too, and gave me verbal encouragement, which I love. His cock was the perfect length and thickness for me to deepthroat, so I made sure that I let him feel the tightness of my throat a few times. I could tell that he really liked that by the sounds he made every time I took him balls deep. Also, when I took him deep, he would hold my head down and fuck my throat for a while before letting me come up for air. As I sucked his cock, he reached over and raised my skirt so he could feel up my ass. My pantyhose prevented easy access to my sissy-pussy, but after fumbling around a while, he found the waistband of my pantyhose and worked his hand down inside of them. He rubbed and squeezed my bare ass and then worked his finger between my cheeks and toyed with my sissy-pussy as I slobbered on his boner.
All the while, he was still idling the car down the street, trying to keep it from hitting parked cars. I started to worry that the distraction of driving might spoil his ability to enjoy what I was doing for him. My worries proved unfounded, though, as he held my head down and fucked my throat one last time, blowing his load directly down my throat. I didn’t even have to swallow. LOL
I kept bobbing on his cock making sure that I swallowed every drop of cum that I could coax out. When I started deepthroating him again, he said “I think you already got it all.” I felt slightly embarrassed at that. I suppose that once he had shot his load, he simply wanted to drop me off and go on his way, not sit there waiting for the whore to finish getting her jollies. LOL
I sat up in my seat, licking my lips as I gathered up my purse. He asked me if he would be able to find me out there again. I took that to mean he wanted to be a repeat customer on his future drives home from work. I had to disappoint him (and myself as well) with the reality that I don’t walk around the neighborhood very often. I told him that he could find me on the internet and social media as TVTiffanySF. He briefly fiddled with his phone and I assumed that he was making a note of my online screename for future reference. I had him drop me off in the parking lot of a business a couple of blocks from my house and then he drove away. I was buzzing with excitement after my first experience as a street whore and I simply HAD to document the occasion. I stood under the lights outside the building and snapped some selfies. I also shot a selfie video clip as I walked home.
At that point, I can tell you that I wanted nothing more than to try to pick up another “customer” and do it again, but I felt like I had already been fortunate to do what I’d done and not get hurt or into trouble, so I simply went home.
That was the last weekend before the COVID-19 pandemic closed the city down. Even though things eventually opened up, I haven’t been willing to risk close contact with strangers since then. Hopefully we’ll get a vaccine soon and I can get out there and give it another try because ever since that night I have been almost obsessed with doing it again. I have researched on the internet about trans escorts, trying to figure out how to go about it in a way that is safer than walking the streets. I have asked a few people what a fair price to ask for is. A guy I chat with said that I should charge $40 for a blowjob, $50 to swallow, and $200 for the night. I’m not certain what he meant by “for the night”, but I assume it means sucking and fucking at the least, and possibly actually spending a full evening/night with someone. Whatever, at least I have his and a couple of other opinions on the matter, which is a good place to start, I suppose. :)
