Made My Tranny Friend Gush Cum All Over Herself free porn video

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So I get this phone call from one of my TS friends while visiting Chicago over the weekend. She works a regular full time job as a retail clothing store manager. The call was to invite me over to her place for dinner and cards with a few others friends. I'd been running all day and needed to shave, shower, and take the 30 minute drive to here loft downtown. Upon reaching her door I noticed it was pretty quiet. I rang her bell and she answered the door in her bathrobe. She looked at me with a glowing seductive smile and said, "You're early, but that's cool. Please have a seat hunny and make yourself at home." So, I sat on her couch while she got dressed and sipped on some Chardonnay. When she came out I noticed she was only wearing a haltered top with no bra, a mini skirt, and flip flops. Her hair, nails, and toes were all manicured and flawless as always. Of course she came out smelling good as hell and was on the phone with one of the other guests. She got off the phone and said with a smirk, "Looks like it's just you and I tonight, the girls are going out to a matinee instead."

Now being curious if she already knew this and wanted me over being recently single, I was more intrigued than ever at this point. At any rate, we ate dinner and retreated to her bedroom as she wanted to watch some movies and this was the only tv in her place. I quickly glanced around her bedroom noticing the lavender scented candles while filled the air. I propped myself on her pillows as she did the same and flicked on the tv. She gasped and tried to tell me to wait but it was too late. When the screen came on it was set to her remote PC and I guess we had more in common than I thought. She was watching tranny porn right from the web. I told her that this was cool and can watch with her if she felt comfortable enough. She then slowly smiled, grabbed me by my shirt and pulled me on top of her. We slowly kissed while I rubbed her hard nipples which were stimulated all throughout dinner. I was turned on by how she easily got hard this way and her cock was about to bust through her laced panties. I removed her top as she removed my polo shirt and shorts. She grabbed my huge black dick and said, "I wanna feel you baby, but damn that's huge so be gentle." I assured her that was no problem. I removed her skirt and panties and was glad that she was a complete cut bottom cause she had to be at least 8 inches. We started to 69 each other while moaning and gasping for air deepthroating along the way. As she pulled my pole out of her mouth she said in the sweetest little voice, "Fuck me papi."

I obliged her while slowly thrusting in and out watching her pussy take my pole encased in the lubed up XL magnum condom. I was compelled how hard her cock was while it dripped precum and waving back and forth. I watched her moan gracefully absorbing my phat cock deep inside. Now, perhaps it was the thickness of her round booty and soft B-cup breast by hormones. Or the well kept French tipped nails and toes that she wore so well. But .. I was about to explode. Little did I know, so was she. While still inside of her I started sucking on her throbbin shecock while her phat head throbbed in my mouth. During this exact moment she said she was about to blow. I released her cock from my mouth and watched the fireworks light up. She stroked herself and screamed while we both watch her heavy cum spurt and shot ropes of thick white cream all over her titties, face, and lips. I asked if she'd like me to shoot all over her and she literally begged me to. So once again, I obliged. As I slowly pulled out of her pussy while watching her start to lick her own cum from her lips, I pulled off my condom and provided her with a quick warning. She started to then sit up in an angle with her tongue out and stroked her cock more with her sexi feet on my chest. She then said, "Spray me papi, please." And so I did, watching my heavy cum shoot out like a spray bottle which glazed her face and titties.

After our session, she wanted me to stay the night and fuck some more after showering off. It was tempting, but knowing I had a 630am meeting the next day at the office would definitely make me late. She gladly took the raincheck for another "dinner date" of which she invited another TS friend to join. Can't wait for part two.

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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
4 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...

4 years ago
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First Time With Tranny

I had fantasized for quite a while about hooking up with a hot chick with a nice cock. I gravitated towards shemale porn and couldn't get enough of it. On this particular day I was having a few drinks and browsing the web for my favorite shemale movies. I discovered the gay.com chat forum. Soon I was chatting with this hot asian crossdresser. She was about my age (21 or so at the time) and lived just a few towns over from me. We shared some fantasies and seemed to have a good connection. She...

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...

2 years 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...

3 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...

3 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....

2 years ago
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A True Life Tranny Experience

My real name’s Benny, and I’m a 32 year old very passable bi transvestite that has an insatiable craving for receiving another guy’s cum. I’m 5ft 7in tall, quite skinny (10 stone ‘ 140lbs to you Americans), and have perfected the mannerisms of a ‘real’ woman in every way, without going over the top by acting too effeminate like some ‘Nancy-boys’ tend to do. That means that when I’m fully dressed and wearing my wig and makeup, I walk,...

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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