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My First Experience With A Shemale

I was living in Louisiana at the time, far away from my girlfriend at the time. I had been increasingly getting into shemale ****. I joined a transsexual dating site and started looking around.
I found a beautiful transsexual about an hour's drive away. I sent her a message and got a response! I was so surprised. We exchanged a few emails and then phone numbers. After a few text messages, we finally got together.
I wanted to be ready for anything so I showered, shaved and made sure I was all clean.
I drove down to her place after she got off work. It was late, as she was a bar tender. She came out to the driveway to meet me. She was tall, smooth and had lots of dark brown hair.
We went inside and chatted for a little bit. The texts we exchanged were pretty up front about what we wanted, so we soon moved to the bedroom. She took off her dress revealing budding breasts and a pair of pink lace panties. I wanted to suck her so much! I pulled her panties down and immediately took her into my mouth. Her moans made me work all the more fervently. I always love it when my partner has more ******* than me and I was determined that she was going to have the first. Soon she told me that she was ready. I redoubled my efforts and I could feel her whole body tense up as her ****** hit her. I could feel her spasm and thrust wildly into my mouth. I could taste her. Sweet, salty, savory... she was delicious. Needless to say, I swallowed it all and wanted more.
We cuddled for a while, but I was getting hard again. She sucked on me for a while, but was getting bored. She put our two ***** together and started stroking. It felt amazing, better than I was expecting it to. I was so turned on, I didn't last much longer and shot all over her smooth belly.
She was in the mood again, and so I asked her to take my virginity. I had played with toys before, but never had someone enter me.
I got on all fours and she got behind me. She lubed me up, put on a condom and positioned herself. I could feel her head press into me and there was a sharp bit of pain at first, but then I started to relax and she took me. She pushed all the way into me and rode me like she was in the Olympics. Twice she orgasmed in my ***. She pulled out of me and cleaned herself up, then came back to bed and we curled up and crashed.
I woke up just before dawn and snuggled on her a little bit. She roused, but I was already in the mood to play. I started sucking her again, savoring the taste of her flesh. I was rewarded by moans and her getting erect again.
She quickly pushed me onto my stomach. I was still lubed up from before and she slid right in. I was in heaven! I was being thoroughly ravished by a beautiful transsexual.
At that point I wished that I was a girl. I wanted so bad to be filled and I didn't realize it but I was begging for it. She pumped me frantically for a few more minutes and then she drove deep inside of me. I could feel her squirting hot and deep inside of me. I started milking her with my ***, wanting every drop of her. Her orgasmic spasms finally subsided after what seemed like an eternity. She collapsed on top of me in a sweaty, tired heap. She was satisfied. I could feel her soften and withdraw from me. I took her in my mouth and made sure she was cleaned off and get the last drops from her. She squealed in mock protest. After that we curled up and went back to sleep.

I went to see her a few more times, but work started demanding my weekends and she started on hormones. She was never able to take me again.
That was now almost three years ago, and I yearn for that experience again.

Thanks for reading.
Steyr Steyr 36-40 8 Responses Jan 18, 2013

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i fantasize about that happening to me

My heart was racing reading this! Very graphic and descriptive! I'm ready to suck n ****... I have a fetish for big dicks..

go have fun, rickityrizzle! I hope you get your fantasy.

Did u pay for the tgirl dating site?

wow intense

my god yes!!! my biggest fantasy!!! good for you man!!!

Thanks!

Wow, I cannot describe how much I would have loved to have swapped places with you. I can only love women but have a fascination with ***** and want to be ****** up the Arse. I have got to have sex with a shemale one day. Thanks for posting the story

What was the site you used? I need an experience like that so bad....

it was a website called grooby personals. Good luck, man!

Did u end up spending money on the site? How much?

I purchased a membership, but I can't remember how much.

Great story .... very hot!