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  #1  
Old 07-06-2009
lbluver lbluver is offline
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Default First time shemale experience

Like to talk about your first time experience with a shemale?

In my case, my first time was in Sidney, Australia. I was there about 10 years ago for a business trip. Although I had never had experience with shemales before, I have seen enough on the net and magazines that I really wanted to try. I picked up one of those tabloid newspaper and I found that you can find shemale ads. I dialed the number and made an appointment (daytime) and this place was far from the city. I managed to get there and I was not disappointed.

Her place is in an residential area (townhouse apartment type). I was greeted by an attractive shemale wearing sexy lingere. The place was cleaned and well-furnished (she told me later that she shares the place
with another working girl (real girl)). After getting the commercial part of
the business over, I took a shower and was in her bedroom.

I sucked my first shemale cock for the first time (it was 7 inches and more).
I must spent 15 minutes sucking and licking her cock, balls and ass. I asked
her to take my virgin ass. She tried and it was too much pain. Eventually, she used a small dildo and fucked my ass while I sucked on her cock. I came as she dildoed me and jerked me at the same time.

That was my first time with a shemale. It was not until another year later when I visited NY and I found a latin shemale with a long but slender cock that took my ass for the first time.

My first fuck was with a ladyboy in Bangkok some time later. I enjoyed being a top as well as a bottom.

lbluver
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  #2  
Old 07-06-2009
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Heather Anne Peel Heather Anne Peel is offline
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The first time I had sex en femme was wonderful. It was several years ago right before Thanksgiving. Through a friend, I met a guy named Bill with whom I really connected. We decided to spend a Friday night together in a nice hotel and he booked it a week in advance. I was so excited, it was hard to wait! I spent all Friday afternoon luxuriously getting ready. I took a long bubble bath, spent hours on my make-up and hair, and finally slipped into my black leather gown and pumps.

Soon, Bill arrived at my place and after I let him in and closed the door, he put his arms around me and kissed me passionately. My heart was racing, I was ready! We went to a nice quiet downtown restaurant and ate a light dinner and had drinks. I played with my hair and with his feet under the table. When we left, I was nervously excited about what was to come (literally and figuratively).

We arrived at the hotel and checked in. Our room was high in the hotel and overlooked the atrium. After we got in the room and Bill closed the door, he asked me to sit on the bed. He opened a bottle of champagne, and poured us each a glass. He sat on the bed next to me and asked me to sit on his lap. I did so, and took off my pumps. We drank our champagne and he kissed my neck and lips. I was getting hard, and I could feel Bill was, too. We lay back on the bed, and I climbed on top of him. We embraced and kissed. He was running his hands all over my body, and unzipped my dress. I slipped out of it, and unbuttoned his shirt while on top of him. Bill unbuckled his belt and I helped him pull his pants off. Before I knew it, I was sucking his cock, 69 style and he was tonguing my ass. All of this felt SOOOO good, I was delirious! He came in my mouth and I was wet, myself. I turned around and kissed him deeply. He was moaning.

After awhile, still on top of him, I grabbed his hard, wet cock and slowly slipped it into my ass. Oh my God, that felt SOOO good, I thought!!! He caressed my body with his large, strong hands and began pumping me. His cock felt perfectly at home in my ass, and I undulated in rhythm with his pumping. He was gone with the wonder, as was I, and after a steady and intense build-up, he came forcefully in my ass. Whew, I thought I'd pass out! Soon, I came on his belly, as well. I stayed in place for awhile, just savoring his the feeling of his cock and cum in my ass. We lay next to each other quietly for awhile and then he pulled me close and began kissing me.

The remainder of the night was was spent in many positions and we both had many orgasms. Bill and I saw each other for about a year after that, and it was always good. Unfortunately, he had a death in his family and ended up moving. We haven't seen one another in a few years, but I am sure that when we do we will rekindle the fire!!!

My first time was storybook perfect, and I will always cherish the memory of it.
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Last edited by Heather Anne Peel; 03-13-2012 at 09:07 PM.
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Old 07-06-2009
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rockabilly rockabilly is offline
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Still waiting for my first time. I hope it's as much fun.
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Old 07-06-2009
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Heather Anne Peel Heather Anne Peel is offline
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Quote:
Originally Posted by rockabilly View Post
Still waiting for my first time. I hope it's as much fun.
I have no doubt that it will be! :D
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Old 07-06-2009
2small2 2small2 is offline
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I am still waiting too!
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Old 07-10-2009
sexchannel
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if you dont jump in you will never know , if you dream it ..try it
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Old 07-12-2009
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The stars have yet to align for me, but im sure they will, someday
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Old 08-05-2009
Collant Collant is offline
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When I was 14 or 15 years, a day in my town a shemale 5not beautifful girl) say' you're a beaiutifuff boy, I go with her in his homme, and i suck his dick and receive my first cum, she was dominant with me and forced me to suck
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