Transsexual Encounter in Chicago

This is a fantasy of a man (me) being forcefully taken by other men and transsexuals and it contains some things that not all may want to read about, including spanking, anal sex, pissing, enemas, etc. If you're not into this type of fantasy please don't leave negative feedback. If this turns you on, please send me a message. It's written in a casual style, not a heavy, formal writing style. That makes it seem more realistic to me. Thanks, and enjoy...

I have always been an assman. I love asses. I love seeing them, fantasizing about fucking then, and fantasizing about having mine fucked. Since I travel a lot all over the country by car, I'm always working myself into a fucking frenzy and I often cum while driving which is probably not the safest thing to do.

I have been fucked in the ass in many rest stops and even in gas station bathrooms, usually due to teasing strangers by not wearing a shirt and wearing stretchy shorts which were usually hanging down a bit so the top of my ass crack was showing. Sometimes it would be a guy cleaning the floors in the gas station who would see me walk in and he would follow me into the bathroom and lock the door. I knew what was coming next.

I'd stand at the urinal and spread my legs and start pissing and more times than I can count some horny stranger would come up behind me and start rubbing my sweaty, tan back and legs. Then their hands would go down to my ass and they would start rubbing it and poking their fingers into my slippery tight asshole. That scenario would always end up with a stranger, or several strangers, fucking the shit out of my ass as I stood there pissing into a urinal. I don't know what it is about gas station janitors but they were always dirty and nasty. They loved to fuck the shit out of my ass, sometimes literally. It was one of my favorite parts of traveling but there were many more scenarios that included strange men using my asshole as their personal pump and dump.

Sometimes I never saw their face or faces, they would just walk over to me as I was lying face down in a hotel sauna or was sitting in a hotel hot tub and they would slide their cocks deep up into my tight little shit hole and pump in-between my bubble butt cheeks and dump a load of hot cum in there and then the next one in line would pump and dump and so on.

This particular trip finds me in Chicago for a client and as usual I'm at a Starbucks early in the morning getting a coffee to go. I was staying in a hotel for two nights so I was hoping for some action. The "woman" behind me in line looked pretty sexy for being probably in her mid-40s with bleached blond and frizzed hair, sort of like a throwback to the 1980s. She looked like a dirty girl and I was hoping that something could come out of this encounter.

I was next in line so when I got to the counter I ordered and then I said that I'd pay for the woman behind me and held my card to the side so they wouldn't run it through yet. The young guy at the counter took the woman's order and she was surprised that I had paid, she seemed very grateful. Being the horny male that I am, of course I immediately fantasized about fucking into her nice little ass and dumping a load of hot cum up there between her cute little cheeks.

We chatted for a bit and it was becoming clear that it wasn't a woman at all, she was a he, or originally, physically anyway. I mean, she was a transsexual and now I was even more intrigued. I had to try to get to know her better if I could. I really wanted to have dirty sex with that woman.

She was also there on business and was staying in the same hotel in Lincoln Park as I was, just across the street. I asked her if she would want to meet up later that evening for a drink in the hotel lobby and she agreed that it would be fun to do that. Needless to say, I couldn't think of anything else that whole day other than what might happen with this hot, sexy, woman with a cock.

At 4:30 in the afternoon I was done with things for the day and I went back to my hotel room to get ready to meet Alexia (Alex?). I showered and primped and got ready, even going as far as giving myself an enema and loading my ass with Vaseline in case anything came out of the evening, or in case anything went into my ass is more like it. I always like to be ready to be fucked so when I'm on the road I usually squirt a dollop of lube up my ass just to make sure that any cocks will be sliding in nice and smoothly.

I have had many encounters on the road where strangers would just come up behind me and start fucking my asshole and since that's my favorite scenario I like to be ready for that.

I was downstairs at 6 pm like we had set up earlier and there she was, gorgeous and she was even more sexy now that I knew that there was a cock hidden under that short skirt. We weren't more than a drink and a half into talking before her hand was on my leg under the booth table and my hand was on her leg as well.

Both of us were casually talking but we were joking about sexual innuendo, turning the most mundane things into sexual situations and my cock was growing by the minute.

My hand moved to her crotch and sure enough, there was a cock under that skirt and it was hard. What now? With both of us having our cocks at full attention there was no way that we could get up to leave and go back to my room and fuck the shit out of each other. We decided to cool it for a minute and things settled back down. Alexia had to use the restroom as did I so we both got up and started walking down the back hall of the hotel bar to the bathrooms. I didn't even think that she would go into the men's room but that's what she did!

That was an interesting development - should I wait, should I go in there and see what happens? Of course that's what I did. I went in and locked the door behind me. She was at one of two urinals so I stepped up to the other one and pulled my stretchy workout pants down in front and started to piss. I had a lot of water that day with it being so hot out and I wasn't sure how long I would be standing there. About five seconds into pissing, I felt her behind me. She was rubbing against my ass cheeks and pulling me back into her and I could tell that her cock was getting hard again because it was stabbing between my butt cheeks which were still partially covered by my workout pants.

Then I could really tell how hard her cock was as she slipped her panties down and lifted her skirt pulled my pants down a bit and was rubbing her growing cock between my slippery butt cheeks. Remember the Vaseline? Yes, she knew that I would be up for anything and all of a sudden her cock head slipped into my tight little asshole and she held it there for a few seconds.

I was still pissing at this time and wondering what was coming next when I felt her whole fat, sausage-like cock sliding up into my tight little, thankfully-lubricated asshole! She pushed it in all the way in one move and pulled me back into her and she was really hitting bottom. I was done pissing by this time and I just stood there waiting for the pounding that was coming next and I was right. She pounded and slapped against my naked and sweaty ass cheeks with all her might, crashing against me and bottoming out in my ass as I stood at that urinal.

Alexia would pull her fat cock out all the way and then plunge it back through my bubble butt cheeks and deep into my asshole. It's a good thing I gave myself an enema or there would be shit on her cock. We were trying to be fairly quiet but I needed to talk dirty, it's just one of my things.

"Alexia, fuck that fat cock into my ass you sexy woman! Fuck me, fuck into my ass with that hard cock of yours. Do you like fucking into a stranger's asshole? Do you like raping a stranger while he's standing at a urinal? I hope that you do because I want to be that guy who gets raped by you! Do you have shit on your cock? You must have because you're pounding so deeply into my poor little raped asshole!"

She said, "Yes, I love fucking in-between your chubby little cheeks and into your tight little puckered pink hole. Your hole is winking at me when I pull my cock out and then as it winks closed I RAM it back deep inside! Your asshole is going to be used and abused by me until you leave town! I love raping your puckered little pink asshole!"

She unloaded a big load of hot, sticky cum deep in my ass and then she pulled a butt plug out of her own ass and put it into my ass! It held all of her slippery cum in there and after a few minutes we left one at a time so nobody would see a "woman" coming out of the men's room.

We went back up to her room where she had a bag full of dildos and other toys with her. She fucked me again twice and cummed in me twice and fucked me with the dildos. She had me bend over in the bathtub and she filled my ass with hot piss. That was dirty and sexy. This now totally naked sexy woman with a cock was pressing that fat hardening cock into my ass and pissing. It was a great feeling, filling me up and then in went the butt plug again.

Then the spanking started while I was filled up with cum and piss and finally the butt plug was pulled out and her cock sank into my abused pink hole again. She fucked and raped and abused my poor little asshole several times but I got to fuck her ass only one time that first night. Her tight little hole was a thing of beauty and I fucked the shit out of her, literally. As I was fucking her I noticed my cock getting dirty and then she let loose. Luckily we were in the bathroom at the time and we cleaned up in the tub with the handheld sprayer, gave each other enemas, and kept fucking. She was a dirty girl and I loved it!

The next two nights were filled with fucking and dumping loads of cum and piss into each other over and over again. Her boss joined us the second night, a guy who obviously knew about Alexia and had fucked her ass before. He really was a hard fast fucker, he pounded into both of our asses over and over again as we were on our hands and knees on the bed. He acted like he was punishing us, like he was raping us, he really spanked and fucked the shit out of both of us. Then he fucked Alexia's ass as she was fucking mine, a big three-way ass-fuck session.

My tiny, pink, puffy, abused and raped asshole was just a plaything for those two cocks that second night in Chicago. They were both so rough on it, even spanking it. They would pull their cocks out and spank my asshole and then plunge their cocks back into it again. I wonder if they had talked about raping a stranger and I was the stranger!

I wish I had another week with them using me as a nasty plaything. It was hard leaving the next morning knowing that it might be quite a while before I met anyone like sexy Alexia again.