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Soooo… from time to time, I like to dress up and meet guys (and ideally, girls, but so far that’s never happened) for some fun. Not going to go into graphic detail about that here since most of the posts I’ve seen here have been more “PG-rated” so far and I figure that more graphic discussion might be somewhat frowned upon, but… yeah.
One particular night a guy I’d been talking to online for a few days came and picked me up, and we had parked in a place that I thought was fairly well out of the way and unlikely to have anybody come snooping to see what that car was doing parked there at 2 in the morning. We’d juuuust started when a car comes rolling down the hill (they would have to drive all the way down, turn, and then come back toward us) and the guy says… it looks like a police car. He panics, pulls up and zips up his pants, and scrambles over the center console to get back in the front seat. I just sit there in the back seat.
Cop #1 gets out of the car, sees guy in front seat and me in the back, asks guy for his information and then calls in another car. Cop #2 is female — I must have been looking pretty convincing that night, because from what I’ve read they try to call in someone of the same gender if possible in case they need to do a search. 😅
Fortunately, this didn’t go nearly as badly as it could have. I assume it’s because they didn’t actually see anything happen, only “suspicious car, guy and girl(?) in it late at night” and checked in based on that to see what was up. We were able to talk our way out of the situation but cops seemed to think I was probably a prostitute — I was asked what we’d been doing, why we were stopped in this particular spot, and if there’d been any exchange of money between us. Of course, they took my ID too so they knew I was crossdressing after that point… but nobody was weird about it, cop #2 basically was warning me about how some people would react badly if they didn’t know I wasn’t biologically female and they found out unexpectedly and basically just concerned with my safety after it was established that there wasn’t any prostitution going on.
Still, pretty scary situation to be juuust about to start something and then the cops show up! The guy was terrified, he was visibly sweaty after the cops left and I don’t recall him being particularly sweaty beforehand so that was a new development, haha.
After the cops left, we drove off across town in the opposite direction… and found a much better spot the second time around, on an abandoned gravel back road waaaay out of town with no houses in sight! Thankfully the story had a good (okay, great, but I won’t go into graphic detail) ending after all. 😅
Things definitely ended well — me and him haven’t gotten together again since then, but we did talk about meeting again at one point (though he suggested probably getting together in a hotel room the next time… he didn’t come out and say it, but I assume that was to avoid any more run-ins with the police! 😅)
Of course, me and him got together back before I stopped dressing up for several months (and then started up again for a month or so, and then stopped again for another couple months…) so communication pretty much got cut off for a while there.
Hi Vanessa I was on vacation and met a man who I was attracted to. I told him before we had known each other for only a couple of hours that I wasn’t a gernetic girl, and I was a crossdresser .He was suprised but it didn’t scare him away In fact he was intrigued by the way that I actually looked and acted like I was a girl After clubbing until the wee hours we went back to my motel room and, well you can use your imagination as to what we did. He ended up staying the night and it was one of the best times I had being on vacation After I went home, we stayed in touch for a while but I never hooked up with him again
I had a similar experience but the police officers snuck up on us and caught me in the act of uh, “taking care of business”. They had us exit the car and accused me of being a prostitute etc. etc. Knowing we weren’t doing anything illegal, I just played a little bit of the harlot and told the officers about what they were missing out on being so closed minded. That kind of threw them off a bit so they took our information down and told us to leave and get a room. I will add that I was purposely dressed like a working girl in very short shorts with high heels and a low cut top with a breast form plate that really had an impressive pair of boobs. I have been told by women that only hookers wear short shorts and heels and that was the look I was trying to achieve for my friend. I guess the cops couldn’t be blamed too much.
Luckily for you Vanessa it did not end up an embarrassing arrest!
I was stopped once for suspicion of a hooker while I was walking. I thought this cop car was following me but was like-Why would they follow me? 5 or 6 blocks later they came around and turned on the lights. I had been in a bad section of town (known by me) and they were suspicious of my intent. I was actually going to a comedy club in the area that night and wanted to know the area before dark. No problems, they were cool and the 3 of us were laughing in a couple minutes. They never asked for ID or my name. I don’t envy there job and am glad to see them around.
Sandy
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