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First Time With Tranny

FIRST TIME TRANNY

... ;. “I like the tranny stories, do you?”

“yes, I love them” I wrote back ... .

A magazine featuring trannies was pushed under the door showing hard sex, penetration, etc&hellip ... couldn’t help but slowly grab my cock, the feeling of pleasure intense.

Another note... Continue»
Posted by stig1963 6 years ago  |  Categories: First Time, Gay Male, Group Sex  |  
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first time with a Tranny

... My first tranny I had was back after I graduated from high school. I was working with her/him ... the car down and spit the cum out. First time for all, she was a virgin well so was I. She told me ... for the first time. The I told her to lay on her stomach and I got up and got some Vaseline came back on put... Continue»
Posted by theho_1 4 years ago  |  Categories: Anal, Shemales  |  
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My first time with a tranny

... to a tranny.

Of course I was wasted and I felt like superman and in no time y reached the usual ... I was very nervous and it was my first time I asked for a blowjob. She told me to drive around ... that it was my first time. She smiled and kept going faster. I knew she would try to rip me off taking... Continue»
Posted by feinor11 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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First Time With Tranny

... first time. Her cock was very nice, probably about 6" and fairly fat. Now she (her name was Sarah ... the story of my first experience with a tranny. Let me know and I will share my second experience! ... towards shemale porn and couldn't get enough of it. On this particular day I was having a few... Continue»
Posted by jay01973 6 years ago  |  Categories: Anal, First Time, Gay Male  |  
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My first time as a bottom and with a tranny

... it was with a tranny

I was 18 and wanted to try being a bottom. For a long time I had experimented by myself ... and I told her that I was looking for my first time, not only with a shemale but as bottom all ... panties off, and then i saw it for the first time, a dick that wasn't mine own. I couldn't even move, she... Continue»
Posted by Pepmeister 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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Fucking my first tranny - Fun times with Jennifer

... something about it and I just didn't want to fuck a woman this time. I've been really curious about ... trannies for a while now, I once fucked a friend of mine when were fooling around (I should write ... interest and would get me really aroused every single time I thought about having sex with one... Continue»
Posted by Sylf 9 months ago  |  Categories: Anal, First Time, Shemales  |  
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First time with a tranny I met on grindr!

... in search of a tranny to fulfill my fantasies and finally I found one!

Her profile read "looking ... gonna waste my time, if you're not serious about meeting then delete my number" I didn't wanna miss ... by her dick pressing against my hole, she pushed harder and f***ed the tip in first, I thought she... Continue»
Posted by Datrap6 8 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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my first tranny..................

... ," hello donnie, 'i'm ida. i haven't seen u here before." "i know," i said. "this is my first time ... and asked if i wanted to go to her place. we wasted no time getting to her place around the corner. we ... naked on top and panties. all i have is tranny porn, is that ok?" "oh sure that is fine." i... Continue»
Posted by tvsucker4u 5 days ago  |  Categories: First Time, Hardcore, Shemales  |  
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My First Tranny Experience

... I was in my mid twenties when I first became attracted to trannys. This was before the internet ... .
I arrived on time at a small apartment block near the city centre. I was extremely nervous as I ... again you can fuck me as well". I assured her that I would definitely be back. That was the first of many visits.
... Continue»
Posted by mjam21 3 months ago  |  Categories: Fetish, First Time, Shemales  |  
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My First Tranny

... xhamster page titled,

"My First Tranny". We corresponded through the dating site quite regularly ... wanted me to stuff her fat ass with my thick dick. Almost each time during these phone encounters ... . Charkara lived about an hour away from me. Throughout the drive, I called her several times just... Continue»
Posted by ghostdawgg62 4 years ago  |  Categories: First Time, Shemales  |  
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My first tranny

... to her. Thats when I saw her cock for the first time. It wasnt very big but it still suprised me. I ... tranny lover. We fucked each other several times a day and night. I had not cum so much in so long ... them and me. I may not have been with a tranny before my first but Im hooked now and love to fuck... Continue»
Posted by wildbill975 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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my first tranny pt. 2

... a tranny dick in my mouth.

I blew her for a few more when she said she needed me to fuck her. I stood ... that before." I told her.

"I want to be your first then."

she kissed me then said...

"you'll ... vibator in my ass several times but it was small. I always wondered what it felt like to get fuck... Continue»
Posted by radec_24 4 years ago  |  Categories: First Time, Taboo, Shemales  |  
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My first time with a tranny

... to admire her body.

I knew next time I'd ask her to fuck me.......... Continue»
Posted by ross80 3 years ago  |  Categories: Shemales  |  
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my first tranny (pt. 1)

... . the first time I fucked a woman in the ass. & I'll always remember the first time I was with a tranny ... you always remember your first time.


I remember my first blow job from an ex. (believe me ... , thats another story.) the first time I touched a pair of tits. the first time I ever ate pussy... Continue»
Posted by radec_24 4 years ago  |  Categories: First Time, Taboo, Shemales  |  
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my first tranny pt. 2

... first transexual. BROOKE! she will not be the last. I really love trannies..... ... was pumping away. every time she pulled out, it hurt. but I was never really given the chance to feel ... .

"fuck me harder. fuck my ass with your tranny cock."

"you like it, do you? you feel really tight... Continue»
Posted by radec_24 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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My Frist time with a tranny

... out throu pics what a tranny was. I must of been 13 at the time or so. She gave me her address ... My Frist time it was back when AOL frist came out. I was in a miami chatroom and I met ... at the same time. She asked me When I was leaving my age, and i Lied to her said i Was 18 , I asked... Continue»
Posted by lucifer696 4 years ago  |  Categories: First Time, Shemales  |  
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Finally, My First Tranny!!!

... own cum off of her cock. It was really wild. These were the first time I have ever eaten cum. I ... . There was 1 thing that seemed out of place though I didn't think of it at the time. This woman, in 85 ... and immediately went to my bedroom. She kissed me and opened my pants at the same time. When she had... Continue»
Posted by adw276 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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the first tranny I looked for

... So i've had some tranny experience unwittingly. I respond to this ad on craigslist from this 19 ... year old tranny who lives fairly far away, but her picture was so sexy I decided to take the hour drive ... ass deeper and deeper and I swear my cock must've been by her bellybutton. The whole time she's... Continue»
Posted by hothothot103 3 years ago  |  Categories: Anal, Taboo, Shemales  |  
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My First Tranny

... machine, doing whatever she desires at the moment. When I felt my cock enter her throat the first ... time, and felt her tongue slide up my cock to the balls, and she sucked the cum right out like my ... stopped and said “hello Cheryl, long time no see you, is this your new friend”? Cheryl asked her to sit... Continue»
Posted by fishkiller 2 months ago  |  Categories: Fetish, Mature, Shemales  |  
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First time out, first time fucked.

... shoes, wig and jacket. Quick check in the mirror and I was ready.

The first thing that hit me ... and swaying my hips. I’d practiced plenty of times at home but this was different and delicious ... but it was the first name that popped into my head.

“Hi, Sarah. What brings a pretty girl like you... Continue»
Posted by Shimmerts 3 years ago  |  Categories: Shemales  |  
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