My First Tranny Experience free porn video

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I was in my mid twenties when I first became attracted to trannys. This was before the internet and it was harder to meet people, but I found an advertisement in a local newspaper for a TV named Susie who offered a massage service. I phoned the number and she sounded nice so I made an appointment.
I arrived on time at a small apartment block near the city centre. I was extremely nervous as I knocked on the door and waited for a response. The door was quickly opened and I entered, not knowing what to expect. I was very relieved as I walked in to see that Susie looked lovely. She was tall and slim, with long blonde hair. Her makeup was understated and she had deep red lipstick and matching nail polish. She was wearing a long silk kimono, and I could see that she also had stockings and heels.
We sorted out the finances and chatted as she showed me into a room that was simply furnished with a bed and tasteful fittings and paintings on the walls. There was also a large mirror on one wall so that I could see what was happening. Susie told me to undress and have a shower, and that she would be back in a few minutes.
When I cam back Susie had lit some candles and there was soft music playing. She told me to lay face down on the bed. I did so and turned my head to watch her as she untied the sash of her kimono and let it drop to the floor. She was naked apart from a tiny black thong. She said ‘would you like me to take off my panties?’ I was overcome with excitement and managed to stammer yes. She slid the panties down and her beautiful cock sprang out, already semi erect.
I continued watching as she arranged towels and lotion, then she lit a cigarette. I was thrilled as I have always had a smoking fetish and would be able to watch her smoking. She took a long drag on the cigarette and put it in an ashtray, then tilted her head back and exhaled a long stream of smoke. Pouring some oil on my back she proceeded to give me a very professional massage. My cock was now becoming very hard as I enjoyed the feel of her soft hands caressing me. She took another drag on her cigarette and then knelt on the bed next me. Straddling me, she laid he body on top of mine and slid up and down over me. I felt her hard cock sliding over the cleft of my buttocks and could never have imagined how good it could be. I was a little shocked to find that I was wondering what it would be like to feel her cock slide into my arse.
‘I think you are ready to turn over now darling’ she said. I was certainly ready as my cock felt like it was going to explode. She applied some more oil to my chest and proceeded to run her hands over me. She smiled as she took my cock in her hand and I tensed. ‘Just relax honey’ she said. I had other ideas and I reached over and gently started to stroke her cock, which was now rock hard. It was as big as mine and looked so beautiful. She moaned softly and tipped some oil onto it to make it slippery for me.
We continued to stroke each others cocks until I couldn’t stand it any more and shot a huge stream of cum all over her hand and onto my chest. When I could speak again I thanked her and she bent down and gave me a kiss on the lips and said that I was very sweet. After I was dressed again Susie led me to the door. ‘I usually only offer massage, but you seem like a really nice guy. If you decide to visit me again you can fuck me as well’. I assured her that I would definitely be back. That was the first of many visits.

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So since I got a good rating for my first sex story, I shall write another one about my first time with a tranny. This happened last year. She was 25, and I was 21. So I am Ash, I am 22, I pretty good and masculine looking. I am mostly a bottom though. I have always been a huge fan of shemales and ladyboys. Respect them and also lust for them :p anyway, so I was in dubai last year and I thought that there might be much more shemales and easier to meet since the place was quite forward with a...

Gay Male
3 years ago
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Tranny Night

Tranny Night: My name is Andrew and I had known Jane since we were very young. She was a precocious child and could play piano and read music from a very early age as well as reading complex novels when most children our age were struggling with reading Enid Blyton novels. I was the brightest boy in our class and would have liked to pretend I was the brightest pupil in the class but Jane's results were always better than mine, although I would not admit it as she was a girl. As...

1 year ago
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Trained by The Tranny

I have always been considered a strong athletic straight black man. I have fucked a plenty of women being an executive in a high profile position. I had everything a man could ask for Power, Property and Plenty of Pussy. Well in life, all things change. I had just landed another two million dollar client and was out celebrating with friends over a local bar. I was feeling real good and I never believed in going home alone…..so why should tonight be different. Then after a few or too many drinks...

She Males
1 year ago
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Tranny Night Out

Tranny Night Out and One Kinky SessionGuess I should start by explaining myself, as a young guy I always knew I was not the same as a lotof my friends and enemies for that matter, girls had no interest in me at all apart from ones who werelong term friends.I knew something was wrong but never worked out what it was till one evening whilst dating a girlnamed Becky I had met on an online dating service who seemed to accept me for who I am.We had been dating for 3 months or so and I always loved...

4 years ago
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First time with a tranny I met on grindr

This is a true story. I am a straight acting 23 year old, 5ft 10 and an athletic 160 pounds. To this point I've only ever been with one guy before in a wild, spur of the moment spring break fling but it had opened my eyes to a world I knew I wasn't finished with. I had joined the gay app grindr in search of a tranny to fulfill my fantasies and finally I found one!Her profile read "looking for a submissive bottom to be my bitch" it was just what I wanted! I eagerly messaged her but began to get...

1 year ago
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My New GF has a Cock Tranny

I'm your run of the mill middle-aged white guy; divorced, decent job, plenty of hobbies, and your standard list of perversions. I love women. I love the way they smell, I love their bodies, I love their personalities, and I really love having sex with them. I've had a few bisexual encounters in my day, mostly back in college, and while I have no phobias about man-on-man action, I have never been attracted to the same sex. Although admittedly, the sight of a large, erect cock has always made my...

2 years ago
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Young Tranny Ch 6 Vegas Sugar Daddy Pt 1

Young Tranny Ch. 6 Vegas Sugar Daddy Pt 1.This is the first half of the sixth story following "How I Started," and shares my experiences between the ages of 19-29. These are prelude stories to the series of "Playtime Stories" I wrote. I hope you enjoy them and comment publicly or privately - it turns me on for some reason! These stories (especially this one) are mostly true so enjoy! I LOVE COMMENTS!!!!This pic is from around that time... enjoy!Over the next two years I worked and played in the...

2 years ago
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Advice for dating a tranny for the semistraig

I will apologize right of for the grammar etc. I am not a professional writer by any means. A bit of prep is in order here. As an adult no one really likes being told how to think or what to do, we have TV commercials for that. That said, as a "Gurl" I may have a bit of insight into why your long fantasized about date with a chick with a dick didn't go as you dreamed. I would also like to point out I am in no way an expert and I am sure my views will differ form other "gurls" so take it for...

1 year ago
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my first tranny pt 1

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. the first time I fucked a woman in the ass. & I'll always remember the first time I was with a tranny.her name was brooke. I always wanted to be with a tranny because I was always curious. I mean, shes a chick right. but then she has a dick. you all know some trannies are drop dead beautiful. this one was....

3 years ago
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Tranny in Toronto Chapter 4 Valentines Day Threesome

Introduction: Message me on forums and tell me whether you like my story or not. Thanks. I wrote this story in an hour, let me know what you think about it. Have a happy Valentines Day. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Discreet Couple Lookn For Valentines Day Fun – mw4t (DownTown T.O) Wife and I want to fuck a lovely female tranny on Valentines Day. Must be bisexual, message me. ________________________________________ Hello, I hope...

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