My First Tranny Experience free porn video

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I should have know as soon as I walked in the bar, the women were hot but there was something about them. I felt it right away but I didn't care, I was horny and needed sex. I hadn't had anything but my own hand and one awkward episode with a watermelon in over 2 months. I'm not a very goodlooking guy but usually when I show them my cock they come around. I got me a big one. Nine inches in length and as fat as a nice cucumber. A horny chick will look past my pockmarked face, pale skin and beginning beer belly once they get a look at my cock.

Anyway, I made my way to the bar. I was wearing my 'get fucked' pants, a little tight and thin enough that a good glance will tell you I got a big cock. I order a beer and almost immediately a tall redhead settles in next to me. She's wearing a sheer top over a red bra that barely conceals her big tits. Her short skirt showed off her pert, round ass. I gave her an up and down look and could just picture myself behind her as she bent over, her big tits jiggling in my hands as I rammed my starving cock in and out of her pussy and later her ass. I had to fight to keep from getting hard. My tight pants only partially hid my starting chub. She was bold. She placed her hand with her long red fingernails lightly on my bulge and gave it a squeeze. That was all I needed. I said, "I hope you plan on taking me somewhere close by or I might not make it."

She smiled and took my hand. She led me thru the bar and down a hallway. She took a key from her bag and unlocked a door. "I am in investor in this place. I claimed this room all for myself." Her husky voice gave me shivers. We went in side. It was a medium sized room with a bathroom inside to the left of the door. There was a huge bed against the wall and a sofa and chair on one side and a table on the other. She led me to the chair and pushed me into it. She straddled me and started taking her shirt off. When she got it off I cupped her big tits thru her bra. She licked her lips and reached behind her and undid her bra. I pulled it off and tossed it away.

I cupped them again and played with them. She pulled my head down and I took one in my mouth and sucked it like a nursing baby. She gave a throaty laugh. My cock was aching in my pants. She must have read my mind because she reached down and undid my pants and reached inside and set me free. "Oh baby the things I will do to this monster", she said. She was slowly running her long, talon like nails up the length of my cock. I was throbbing. I started to slide my hand up her leg, fully intending to get my itching fingers into her pussy. She stopped my hand mid thigh. "No, no, no" she said, "You first". She stood up and knelt in front of me. "Stand up and take off those pants, let me see that big ole cock and those balls".

I did as she said. I kicked off my shoes and took my pants off. I pulled my shirt over my head. I wanted to be completely naked for this. My cock danced in front of her face. She smiled and licked her lips. She told my to sit, so I did. My cock stood proud, waiting for her to wrap her saliva slick lips around it and suck. I said, "When do I get to see my treasure trove?" She laughed and said in time my darling.
Then she proceeded to take my cock in her mouth and swirl her tongue around its head. She slid her lips down the shaft till she had almost all of it in her mouth. I had to think of baseball to keep from shooting my load straight down her throat right away. She proceeded to give me the blowjob of a lifetime. Alternating between sucking my cock and sucking on my balls. I was going crazy.

"Okay baby, If I don't fuck you soon this hard on will not make it past your mouth. I need to fuck you." I told her. She stood up and took my hand and lead me to the bed.

"Will you fuck me in the ass baby?" She asked me. I was floored. I love a good ass fuck, it so tight and not a lot of my girlfriends would let me do it. "If that's what you want, I have no problem with that." I told her. She lay face down on the bed and pulled her skirt up over her ass. "Just push the panties aside, I like being ass fucked while I'm wearing my panties." She told me. I really didn't care. I just wanted to sink my cock into something and fuck it at this point. It was sort of dark in the room, I suggested turning on the light but she said no, she needs my cock right now. I thought 'fine by me'. She handed me a bottle of lube and I covered my throbbing cock and proceeded to push into her ass. She we both moaned with pleasure as I sunk into her tight ass.

I started out slow, but soon I couldn't help my self , I was ramming in and out of her as she moaned with pleasure. I was grunting. She was going on and on about how good my cock was making her feel. I wanted to cum but didn't want to end it yet. In my rush of pleasure, I quickly pulled out and flipped her over, intending to dive into her pussy. I pushed her skirt up to her waist and grabbed her panties to pull them down. When I did, I was met with the shock of my life.

Where I expected a juicy pussy to be, was instead a cock almost as big as mine! I was stunned I just stood there staring at it. Was she a hermaphrodite? Was she transgender? What the hell was going on. She began stroking herself. "Whats wrong baby? Don't you like my cock?" she asked me. I stuttered. "You have a cock? Why do you have a cock? Where's your pussy?"

She gave me a throaty laugh, "Baby doll, are you telling me you didn't know? What did you expect to find in a tranny bar?"

I took it in. What do I do now? As surprised as I was, my cock was still rock hard and my balls were about to explode if I didn't come soon. I'm a straight man, Ive never even thought about being with another man. Well maybe once or twice in high school but not since I started having sex with women. I was torn. My instinct was to run away, but up to now it was all feeling so good. I stammered out my indecision. "I..I..I've never done anything with another man. I don't know how...I don't...oh fuck if I don't soon cum I'm gonna explode."

She took my hand and placed it on her cock. It felt so foreign, yet familiar to me. I wrapped my fingers around it. "Sweety Ive already sucked your cock, its okay, you liked it didn't you? Don't worry, no one needs to know. I can either suck you till you cum or you can fuck my ass some more. It felt really good when you were driving that big fat cock into my ass. What do you want me to do?"

I sat on the bed, my hand wrapped around a cock that wasn't mine. Oh the hell with it, I just butt fucked a man, its done. "Suck me off, I need to cum."

"Sure thing baby". She slithered to the floor in front of me and took me in her mouth. She sucked me like she did before. Only this time I didn't have my eyes closed just enjoying it. This time I watched her...him?..whatever.. suck my cock. When she released me to go for my balls she said, "You can cum in my mouth if you want or on my tits, whatever you want." I let her suck my cock and balls a little longer then told her I was going to cum in her mouth. She took my head between her lips and stroked my cock. I let out a groan and felt my balls empty into her mouth. It felt like I came for a long time. I watched as she took all of it, swallowing some and letting some run down my shaft and over my balls.

Id just let a person with a cock suck mine till I came and it felt marvelous. Without even thinking about it, I pulled her up onto the bed and lay next to her. "I never did this before but I'm gonna suck your cock and I want to feel your cum in my mouth." I took the purple cock into my mouth and did what had been done to mine. I kinda liked it. Suddenly her hands were on my head and she let out a growling sound. I felt the warm cum spurt into my mouth, spurt after spurt. I tried to swallow it but I couldn't do it. I let it run out my mouth and down the cock I strangely didn't want to release from my mouth.

I have to admit, for a straight man, that was some of the best sex Id had in a few years. I cant lie though, I missed licking pussy and feeling those juices flow over my tongue when the woman comes. I kinda missed fucking the pussy too, but I can honestly say if a tranny offered me sex I probably wont turn them away.

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-------------------------------------------------------------------------- I went to Alan's house after work one day to talk to him. His mom was single and she need a male figure to discuss masturbation since she had caught him doing it. I rang the bell. I heard footsteps on the stairs and then the door opened. "Hi Alan." "Oh, hi Mr. Jones." “Can i come in?” “Sure,” he said holding the door open. “Alan I have to be home soon, so let me just say this quickly: I know your mom caught...

3 years ago
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My Tranny Teacher 4

This is a fantasy story. Every day left me feeling more horny and excited for our next tutoring session with Ms. Bennett (Becca). I was hard about 90% of the time just going thru all of my special clothing and deciding what I could get away with wearing to school that would light up my teacher and make her clitty into a full stiff dick that I could put to use. After looking at everything I decided that black lace top stockings would be exciting and could not be noticed under my school clothes....

3 years ago
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Threesome with a tranny and a woman part 2

I had just finished fucking and sucking with Bree ( the tranny) and Tammy ( the woman) and we all wanted more. If you did not read the first story please do that so you know what's going on. We were laying there getting our breath back and I looked at Tammy. Now that I knew she was a woman I really looked her over. She was about 5'3" with a fantastic body and shoulder length blonde hair. She had big tits with extra large nipples that looked like pencil erasers only longer. She had a little...

2 years ago
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Tranny Arschfick in der Jugendherberge

Fabianes ersten ErfahrungenFabiane, die ursprünglich einmal Fabian hieß, war eine Tranny und hatte gerade ihren 20. Geburtstag gefeiert. Sie war Berufsschülerin. Als solche übernachtete sie regelmäßig die Woche über in dem Hotel, in dem ich an der Rezeption arbeitete. Dieses Hotel war zwar an sich eine Jugendherberge, aber ganz im Stiele eines Hotels. Somit hatte ich mit vielen jungen, coolen Menschen zu tun. Mit einigen entwickelten sich manchmal Freundschaften, so auch mit Fabiane. Sie kannte...

3 years ago
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Trucker the Tranny

Jermaine Simpson drove his white 2010 Peterbilt raised-roof big rig into the truck stop just outside of the city. He called his friend, Mariah.“Hey, baby,” the dark-skinned transsexual answered.“What’s up boo? I’m at the truck stop,” Jermaine shared.“Okay, oool! I’m on my way.”“Awesome! Can I get a shower at your house?”“Of course!”“See you in a few.”“Bet!”Jermaine’s nine-and-a-half-incher was already hard. He loved fucking her whenever he was down this way. Once he had taken her on a six-day...

4 years ago
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BuildaTranny

Garvey Williams kissed the pretty, effeminate, white boy he had had been secretly fucking since they were high school sophomores. Back then, Garvey was a standout wide receiver with high prospects of moving on to Division One. He had progressed as everyone thought and Jamie Collier, the femboi, followed him to the large state university. Garvey and the Mustangs earned a national championship his junior year. The football prodigy decided that he should enter the NFL draft immediately following...

4 years ago
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My first tranny girl experience got me hooked

I have always wanted to have sex with a tranny. I find these women sexy. In my daily life I dont know any, so I look online find a tranny to fuck. As I look online I find a sexy Cuban t-girl advertising sex. I instantly give her a call and arrange a time to go meet. One thing that turned me on is that she just moved from Cuba and had an spanish accent that turned my dick rock hard. Once I get to her home she leads me to the bedroom. She is 5'5 about 125 pounds. My girlfriend is 5'9 160. So my...

1 year ago
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Fun Time With A Top Tranny

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...

3 years ago
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Truck Stop Tranny Sluts

My girlfriend and lover Candi and I were driving back to her place for some steamy tranny sex after a night of partying at a tranny/gay bar in town when we passed a truck stop on the highway. Buzzed and horny as we were, we laughed about stopping in the lot and doing so hookin’ as a means to get us some trucker cock. After a minute or two of silence, Candi said lets do it and before I could answer she was turning back for the truck stop! Candi and I are both bisexual crossdressers and we pass...

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