My First Time With a Transexual

This is a true story it happened back in 1986 I already knew I was bye and I liked having sex with girls and guys but I had never had a transexual. I went out clubing where all the gays and lesbian hang out just to hang out and have a good time there was always someone who would accept a straight looking guy like me so I went into this one club that had a transvestitied show or shemales show it was a great show they had some singers, dancers a couple of comedians the show was very good so I had to stand at the bar in between to girls who were dressed in business suits very sharp nice asses and great looking tits they were about my height, had all the curves in the right places so I invited them drinks they accepted, so we started talking about the show they told me they were regulars there, I said they looked great and very sexy. One said her name was Mary, thanks that it took a lot of work to look that good. I comented that she must go to the spa or something she said that she did I told her she was really getting her monies worth. Our converstation got around to if she wanted to go out with me, she asked me if I knew what she was I said no she said that she wasn't what I was looking at that she was special I said she sure was and than she reached for my cock through my pants and in a very sexy voice said she had one of those and if I was OK with that than she'd take me home and let me get better acquianted. Let happen what was to happen. I said to her I'm very open minded and would love to get to know her better. So we left the club and went out to my car, we drove a few blocks to her condo. She let us in, turned to give me a very hot kiss with tongue and all I could feel her tits push against me and the rest of her was so smooth I reached down to grab her ass she moaned in my hear saying you know what I like. We gradually moved over to her couch, I openned her blouse, so I could suck on her tits they we soft, very beautiful brown nipples, which I sucked very softly at first, she moaned again said to me to suck them harder. I took off her blouse and bra, while she work to remove my pants and shorts I openned her pants and slipped my hand into her panties I found her cock tucked between her legs she was very smooth this got me so hot that my cock was as hard as a rock she kissed my chest and sucked on my nipples she continued down to my cock she licked it than took it into her mouth which was so hot I almost came we moved down to the carpet switched ends so we could 69 I took her cock into my mouth and I work it for all I was worth. She just groaned on my cock, began to move her hips back and forth fucking my mouth with her cock so I did the same to her after about 10 minutes she groaned that she was going to cum in my mouth I let her know that I was going to do the same so we keeped at it, we came almost together I keeped sucking her cock very softly until she pulled out. We both kind of laided there panting, she said that she really needed that. If I was up to more I said of course. She rolled over got to her feet she went to the kitchen for a couple of beers, we sat on the carpet drinking beer for a while, she asked me if I had ever been with a shemale before I said no you are the first but not the last. She lead me into the bedroom so we could more confortable, I started to kiss her cheeks and lips I moved down to her tits I caressed each one than I suck her nipples one at a time until she stared to moan softly I continued on down to her belly button than finally to her cock which I licked all around the tip than the length I continued licking and caressing her between her legs on down to her knees calfs and ankles finally to her feet, kiss each and sucked each of her toes, than I turned her over and started back up her legs to the back of her knees to her ass which I ate with gusto now she was moaning and groaning she put her ass in the aire so I could really get to her little hole to stick my tongue in her ass hole which tasted just fine after a bit I worked my way back up her back licking and caressing her spine until she said that she was going to cum again. I said not like that your not I turned her over so I could grab her cock and put into my mouth to suck her off again. She came very hard with maybe 5 or 6 squirts of great tasting cum which I drank down again. This made me so horny that before she could say anything I turned her over again pulled her ass into the aire, so I could shove my already rock hard cock into her ass she moaned and pushed her ass back into me, I was so hot that I could only fuck her ass for a short time maybe 9 or 10 minutes before I came in her ass. I was spent but I didn't pull out until she said that she had to go to the bathroom, she said if I wanted to take a showwer with her I jumped at the offer, and thats another story. This was really a true story of my first time with a shemale but not the last. let me know what you think.
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Posted by jackguns
4 years ago    Views: 4,787
Comments (24)
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6 months ago
I'll go so far as to say great! I've never done that but maybe in the future
1 year ago
Wow that was very hot, lucky u.
2 years ago
good story... makes me want a she male even more..mmmm
2 years ago
Wow I've been there and a similler experience but i didi enjoy myself to no end
Jay
2 years ago
Positive criticism*

I do it too sometimes lol afterall we are just human

Well have a good one,
~Rosalina~
2 years ago
Looks like I am the first trans female to comment on your story. It was great, erotic, and overall entertaining. But only a couple of flaws with it. Now I am not saying this to be an asshole or anything but it had a little bit of grammatical errors which is not bad, but I did have to re-read a couple of sentences to understand what you were trying to say. But nonetheless a great story, I liked it and it makes me want to go clubbing more often lol :)

P.s. I hope I didnt offend you, I meant that as positive critocism
2 years ago
It's so exciting to read, my cock was hard all the time. It must be very very exciting to experience it yourself. My heart would beat off of my chest. Shemales 'can be' so sexy and hot. If they are feminin I love them. I like it when she said : I have one of those ! when she grabbed yours. THAT is excitement ! I hope for you the story is true. I have a few friends here and I am happy you are one of them.
2 years ago
IF NOT FOR MY DAUGHTERS & GRAND CHILDREN I HAVE ALWAYS LOVED TOBE A SHEMALE. I LOVE TO SATISFY A MAN. MOMMY ALWAYS WANTED TO B A HE SHE.
2 years ago
hot story
3 years ago
very erotic
3 years ago
Great story, wish it had been me.
3 years ago
My dream shemale encounter. I like that he got to lick and eat her cum twice he should have let her fuck him and shoot her cum up his ass hole.
Sowe2442
retired
3 years ago
great story. hoping for the same
4 years ago
great story I would have loved to be in your shoes,I always wanted to be be with a transexual even have a long term relationship,hopefully someday soon...your a lucky man
4 years ago
I would love that good time...
4 years ago
great tale, got my cock hard picturing u together, wish i cud have been there to wank over u both
4 years ago
good
4 years ago
Wish we could have done her together. Hot story. I would have loved to lick her ass clean ater you fucked her
4 years ago
My wish for the same
4 years ago
Very hot story, thanks for sharing.
4 years ago
like it very much
4 years ago
that sounds like alot of fun, i wish it was me
4 years ago
wow great story, tell the sotry about the shower, sounds like it could be hot
4 years ago
exellent story, lets hear more