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My surprise

Tags: shemale, anal, oral
My only time with a shemale (unfortunately)
I was out one night with a bunch of my guy friends and we were cruising around town looking for chicks. A couple of girls stopped to talk to me and another guy I was with and invited us back to their place. Well, only 1 girl lived there and the other decided that she had to go home. So there we were in the house, two guys and one girl. She was making out with me and ignoring him, which was kind of funny because he was always getting the girls. He ended up falling asleep and she started giving me a blow job while I played with her tits. After playing with her tits for a while, I started to move down her tummy towards her pussy. She kept stopping me from rubbing her down there, so I figured she must be on her period, so all I was gonna get was a blow job.

After a while of her blowing me, she asked me to go upstairs with her. As we were walking up the stairs, she had all kinds of pictures of herself on the walls. She said that she is a performer. I didn't think much of it. I was too horny to care. When we got to her room, we laid down on the bed and she told me that she isn't as pretty without her makeup. I told her that I didn't care. She was beautiful. We started making out and we both got undressed. When she took off her shorts, there was my surprise and the answer to why she wouldn't let me rub her pussy. She didn't have a pussy, she had a nice 6" cock. I have been curious about being with a guy before I met her, and now I had the chance to see what it was like.

We got in the 69 position and sucked each other for a while. Wow, I was lousy at sucking cock. She was great though. She asked if I wanted to ride her and of course I said yes. She laid on her back and put on a condom. She lubed up real well and told me to slide down on her cock. It felt so good going in. I started riding slowly and then picked up the pace. I was riding so hard that I kept coming off of her. She had me lay on my back and put my legs up in the air. She put her hard cock in my ass again and fucked me good. I loved watching her tits bounce while she fucked me. She went deep inside me, I felt like I had to pee every time she drove into me. I loved it.

I called her a couple of days afterwards and hung up the phone when she answered. I wanted her again, but I knew that my friends and family wouldn't approve of her. Now that I look back, they probably would have never known that she was a shemale. She wasn't supermodel pretty, but she had the down to earth type of pretty. It would have been fun to go places with her, knowing what kind of surprise she had in her pants and nobody else knowing.

I have tried to contact other shemales, but they always want to charge for their "services". I'm not looking for just sex, I want a shemale friend with benefits. Oh well, I guess it just wasn't meant to be. Now that I am married, I guess I should just focus on getting my pleasure at home. Oh how I miss the single days sometimes.

I would love to hear other people's stories on experiences with a shemale. Also if there are any shemales that would like to chat, please get with me. :)

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Comments(5)

naughtykellypreston
Posted 18 Mar 2014 12:26
nice little story, just a little short and not much details.
whysoserious
Posted 21 Jan 2012 04:03
great read.........must have been a remarkable experience!
BiSexlover
Posted 29 Dec 2011 12:35
Hey, GREAT story although I wish it had been more detailed. I have been lucky enough to be with a she-male a few times...Both here is the U S and over seas, and sex with a hot she-male is fucking AWESOME ! !, Even had a 3some a couple of times with my wife and a she-male ! .
1kinky1
Posted 29 Oct 2011 03:05
Thanks, it sure was a fun time.
allion361
Posted 23 Oct 2011 15:45
I am tranger and know what is like to be in your shose.
 

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