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Old 12-15-2007
capablanca capablanca is offline
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Default My first time

I recently had my first experience with a shemale. Here's how it happened.

For the last few years I've being seeing escorts, and I search for them online. I noticed adds for shemales, and they looked pretty hot. Didn't think anything more about it, though, for a few months.

One evening I was seeing a girl I'd seen a few times before. She was complaining business was down - was losing trade to shemales! It wasn't long before she lost another one: me.

I looked up available shemales in Toronto, and went to one next chance I got. Oh my god oh my god what an experience! I won't give her name here but will do so in a private message. She was about 5'8", blond, and very, very feminine. She took me into her bedroom, and had me lie down. I looked her over as she turned away for a minute. She was so beautiful - there was no way anyone could have known she had not been born a woman - that is, until she turned around, her dick exposed with a condom on it, and said to me, "suck my cock".

Now that is what I had come there for. I had been fantasizing about sucking cock, but the idea of doing it with a guy grossed me out - I had to do it with a girl. So here goes.

Now one problem I have is that my gag reflex is really strong - makes trips to the dentist kind of tough. So I couldn't take as much of her cock into my mouth as I wanted. But I tried my best. After a while, she took the rubber off when I asked, and I kept on going. What I really wanted was for her to cum in my mouth but she didn't want to cum (I found out that most of the time a shemale escort is not going to cum until they're on to their last customer of the day, for obvious reasons). She stayed standing by the side of the bed, holding my head with one hand while she fucked my mouth - a huge turn-on for me.

She she put another rubber on, and told me she was going to fuck me. This was not part of the plan - not something I'd been fantasizing about. But it was really interesting - she was very much the take charge type, and was running the show, so I thought I'd go along with things, and I let her move me around so I was lying on my back, my legs over the edge of the bed.

She had some lubricant, and worked it into my ass.

"You're really tight," says she in her cute east european accent.

"I've never done this before," I explained. That seemed to turn her on. "I'd better open you up a bit first." She got a dildo from a drawer, put a rubber on it, and started to gently work it inside me. After a while she was gently fucking me with it, while I squirmed underneath her, watch her beautiful breasts jiggle as she worked on me. After a while, she pulled out the dildo, and suddenly I felt her hardness pressed up against me. She was much bigger than the dildo, and had some trouble at first. She told me first to squeeze very tight, and then to relax. As I relaxed, she inserted the head of her cock in me. Then she told me to squeeze hard again, and then to relax, and pushed further in. Then she started short, quick strokes which seemed to open me up, and in no time, she was in me to the hilt.

Now I'm sure there's no right wing anti-sodomy republican types reading this post, but just in case there is such a person, I want to tell him something. You can take all your crap about sodomy not being natural and shove it up your ass. Now I can say with total authority that being fucked up the ass is the most natural thing in the world. I absolutely loved it! I had never been so turned on in my life with the wonderful sensation of her hard cock sliding past my prostate over and over again, faster and faster. She talked to me as she fucked me:

"So you've never been fucked before? Want me to stop now?"

"No don't stop please don't stop keep fucking me oh godddddd"

"You're sure now? I don't want to hurt you!". She leaned forward closer, and held my shoulders while she fucked me harder. I pulled her face down to me and we kissed - a huge turn on with a cock up my ass.

She straightened up again and started to work on my cock while continuing to push in and out, her pace slowing a bit as she started to jerk me off. In no time I had such a powerful orgasm that my balls hurt, cum flying all over the place. She laughed as she watched me spray everywhere. When I was done, she pulled out, and off I went to the shower.

After goodbyes, I was in my car a few minutes later, already hard as a rock just thinking about what happened.

I still see women a lot more often than shemales, but I will never stop seeing a nice shemale now and again. There's no experience like it.
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Old 12-15-2007
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Leeya Leeya is offline
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Leeya will become famous soon enough

Thanks for sharing your story!! Waiting for new adventures to come
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Old 12-16-2007
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SSL SSL is offline
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Join Date: Jan 1970
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Thank you for the excellent story mate, I have republished it at the blog so more people could enjoy it.
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Old 12-16-2007
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nice, thanks for sharing.
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Old 12-16-2007
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Dude, I'm sooooo jealous right now! Haha
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Old 12-21-2007
kiesster kiesster is offline
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touching story
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Old 12-21-2007
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SweetCharmer SweetCharmer is offline
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Location: London, England
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SweetCharmer will become famous soon enough

you are one lucky man y'know that hehe
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Old 01-28-2008
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ila ila is offline
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Join Date: Jan 2008
Location: Canada
Posts: 6,273
ila has a reputation beyond reputeila has a reputation beyond reputeila has a reputation beyond reputeila has a reputation beyond reputeila has a reputation beyond reputeila has a reputation beyond reputeila has a reputation beyond reputeila has a reputation beyond reputeila has a reputation beyond reputeila has a reputation beyond reputeila has a reputation beyond repute

Great story. You have lived my dream. I can hardly wait to suck my first shemale cock and to have her fuck me in my ass.
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Old 01-29-2008
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Sounds like a bloody lucky guy to me!!!
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Old 01-29-2008
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tlover tlover is offline
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Join Date: Jul 2007
Location: u.k north west
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tlover is a jewel in the roughtlover is a jewel in the roughtlover is a jewel in the roughtlover is a jewel in the rough

That's a great story, very horny.
I hope i have a experience like that soon.
Tlover Give it a go, you never know.
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Old 02-07-2008
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ocinteeni ocinteeni is offline
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ocinteeni will become famous soon enoughocinteeni will become famous soon enough

sounds like fun, i like how she laughed at youspraying everywhere. She probably really gets delight from it
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