My first REAL fucking

My first real fucking involved a transvestite whose advertisement I`d seen in the local paper. When I say Real fucking, I was about 25 and had been with a few drunken guys (while I was very drunk ) and had sucked a few cocks, always very quickly and very badly and generally didn`t really remember much the next day. I had been with a few girls but it was never really satisfying, they never wanted to go anywhere near my arse and generally wouldn`t let me near theirs. One day after working night shift I was reading the sex ads in the local paper and decided this was it. I tried a few transsexual ads but because it was only midday they weren`t interested. Finally I found a young Transvestite who agreed to come over(she was in the bank when I rang, a little bit awkward, lol ) and after agreeing on price it was on , wow, it was the first cock I had ever sucked while sober. It was AWESOME ! After about 5 minutes of sucking she asked if I wanted to fuck her, no way , I wanted her to fuck me. I knew if I came in her I probably wouldn`t want a cock in my arse straight away and I would miss my chance, so we agreed I would go first. I should point out I had a virgin arse (apart from a few small dildos ) and didn`t know a lot about anal sex. Long story short I loved it, she wasn`t thrilled as I hadn`t really prepared myself, things got messy, lol. Since then I have been fucked many times , mainly by transsexual prostitutes, but I always spend time on the toilet before they get there !
Published by merc123
9 years ago
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Sissy-cunt-boi
Sissy-cunt-boi 7 months ago
Ooh, love it! I learned fairly quick that I should do a cleaning phase before going full on anal play. 97% of the time it works. But, I've yet to get the real feel of anal pleasure.
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cumlnmymouth
cumlnmymouth 8 months ago
to billdarnell2 : same her hun
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billdarnell2
billdarnell2 1 year ago
I'm still waiting to get my boi-cherry popped. That must have felt awesome!
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suckingdicks81
suckingdicks81 1 year ago
Even though it's been 40 years, I could never forget the first cock that fucked me.
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xx1236
xx1236 3 years ago
AAAAA++..!!!!
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SancheZ069
SancheZ069 3 years ago
Interesting :smile:
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nofishforme
nofishforme 4 years ago
Cool honest story, thanks for sharing.
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kevb1uk
kevb1uk 4 years ago
Love fucking tranny's :smile:
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chiefconsultant
chiefconsultant 4 years ago
One guy told me that when you play in mud you have to expect to get dirty.  It did not bother him or others that fucked my ass (I did clean and it wasn't a total shit fuck)
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Edforhead
I must admit it’s the messy bit that puts me off
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