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This is a true story, but it isn’t all that recent. It was at the height of the pandemic when everyone was still wearing masks and being extra careful even with hook ups. For the better part of the pandemic, I cammed with people and used my dildo to fulfill my desires. At the time, I was living in the heart of Manhattan across the street from a hotel that before the pandemic was at all times busy but had become pretty desolate. Even though all of my classes had transitioned to remote, I opted to stay in the city. In fact, most days I would just get dolled up and live out my life as Jenna. Normally, I would draw all the blinds and transform into the “real” me. I loved every moment of it, but it still got lonely, especially in the early days of quarantine.

One night, I noticed that the lights were on in the hotel across the street. I found out that the hotel was being used to provide emergency medical personnel with temporary housing due to the doctor shortages in the city. I was on a higher floor and from my room could look right into several of the hotel rooms although most of them had their curtains drawn, which relegated the view to a bunch of random shadows. A few nights after the emergency personnel moved in, I noticed the lights go on in one of the rooms that had its curtains wide open. A man walked in with suitcases, wearing scrubs, and what I think was a face shield. Even without binoculars, I could see the guy walk around his hotel room to get a lay of the land – a king size bed, television, dressers, and a bathroom. As I watched him walk around, I completely forgot that I was staring and that I was completely dolled up and had forgotten to close my own blinds. I’m pretty sure he saw me staring, so I hurriedly closed the blinds, which was probably an even greater clue that I had been watching him. A peeked through the blinds and noticed that his windows were still wide open. With the curtains open, he started to undress. He pulled off his top scrubs to reveal a well-defined chest with these well-formed but not overdone pecs. He was a gorgeous black man who had to be a little over six feet tall. Next, he pulled off his scrub pants and then was only left with a pair of boxers. I could feel my clit getting hard as I watched this beautiful man walking around in nothing but his boxers. Every now and then he would look out the window in my direction, which really freaked me but was also a gigantic turn on, especially since I had been all done up as Jenna.

Next, he sat at the desk next to the television. He pulled out his iPad, set it up on his desk, and must have navigated to some sort of porn, because before I knew it, he had whipped out this huge black cock and started to stroke it with such vigor that I found myself panting. At this point, I wondered – fuck it. I pulled up the blinds and he looked right at me. I started to fondle my breast forms through the lace bra that I was wearing. I undid my robe so that he could see my bra. He stood up from his desk, came to stand directly in front of his window and kept stroking his huge cock. Fortunately, since my windows were not floor to ceiling like the hotel’s I was able to stroke my clit while I continued to play with my fake tits. At this point, he slammed his left hand against the window, leaned it, and continued to furiously stroke his cock with his right hand. He smiled; I smiled back. He pulled back from the window and started to bounce his pecs all while continuing to stroke his cock. I stuck my tongue out as if I was licking the precum off his cock and he continued to squirm with his cock in his huge hand. At this point, still standing away from the window, he took both hands and started to stroke his cock. At this point, I was all in. I made sure my clit was tucked in well and then I hopped up on my bed which is right in front of the window. I turned around and showed him my ass. He went crazy.

He was nodding, shaking, and stroking. Even from a distance of about 250 feet from my building to his, I could see him sweating. His pecs were glistening. Selfishly, I returned to the window, because my clit was insanely hard, and I wanted to cum with him. We continued to tease each other from a distance. At this point, he put his right foot up on the chair near the window and continued to stroke while never looking away from me. I could see his balls flopping around. It was so hot. He nodded, I saw his head go back, and then he blasted a huge load all over his window. As he was cumming, I felt my clit swell and the cum traveled up my clit. I could no longer hold it and came all over my hand of course out of his sight, but I made sure he knew I came too. Spent, he smiled and fell back on his bed. I was sitting on the edge of mine, mesmerized still by his gigantic cock even when it was soft.

He got up from his bed, walked over to the desk, and took out some paper from the drawer. He started to write or draw something as it wasn’t entirely clear. Then he walked over to the window, pressed the paper against the window and I could clearly see it said #1103 – his room number. Second sheet of paper came up and he pressed it against the window, “Tomorrow @ 10 pm.” I was in shock and nervous as all hell as this guy wondered I was a woman and had no clue that I was crossdressing. He smiled, arched his shoulders as if to say, “so?” I nodded, smiled, and blew him a kiss. He slept with his windows open all night, laying naked on top of his bed – I think he did it on purpose in the event I was having second thoughts about tomorrow night.

I went to bed a very happy girl but was terrified about what might happen when he finds out I am a crossdresser. Should I distribute where it went from here?

NSFW: yes

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