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The Perils of Pauline Trannie at The Truck Stop

The Perils of Pauline - Trannie at The Truck Stop By Michele Nylons Paul sat behind the wheel of his Mustang, the windscreen opaque with heavy rain. It had been raining hard for the last hour and he was hoping it would have stopped before he reached the truck stop. He looked through the windshield as the wipers lazily swept back and forth across the glass. The sodium vapour lamps bathed the parking lot in an orange hue. The blacktop was slick with rain and puddles had...

Old trannie gets a boys virginity

Oh dear I’ve been a bad, bad old trannie. I let a teenage boy seduce me.I normally only go with guys over 30 at least. But this teenager contacted me on a dating site. I gave him the normal “Thanks but I’m in my 40’s you’re a bit on the young side for me” reply. However he kept contacting me on the site. He was very curious and quite sweet. I chatted with him online and he said that he would really love to meet me.I told him if he wanted to meet me that he could find me at my local sex club....

Revenge on a Tranny

Revenge on a Tranny My relationship with my partner Julie had been strained over the last twoof our ten years together. For a period of six months we?d stopped having sex.I thought she might leave me but I figured that if she was going to find anotherwoman then there was nothing I could do about it and besides, I had a womanor two I knew I could fall back on for affection if I ever found the need.I was a good lover, but there seemed to be something that Julie needed sexuallythat I couldn?t...

Fucking my first tranny Fun times with Jennifer

This happened about a month ago, it was one of those days where I felt really horny so I had to do something about it and I just didn't want to fuck a woman this time. I've been really curious about trannies for a while now, I once fucked a friend of mine when were fooling around (I should write a story about him too!), but the combination of tits, smooth ass and a cock would always catch my interest and would get me really aroused every single time I thought about having sex with one. A little...

My Accidental Tranny Date

About 3 years after my divorce (This was over 30 years ago); I decided it was time to get back into dating again. I finished my Masters. I had a good career. And a few good friends who helped me with my sexual desires. But it was time to try getting into a relationship. Dating online is very hit and miss. I met some really great people and some not so great. Fortunately if you’re smart; you can wade through most of the unwanted ads. One of those dating ads got by me; catching me...

Dream Tranny

Dreams can be strange, sexy things. Your wife may be a stunning knock-out, way the fuck out of your league, but I bet she ain’t your dream girl. No, your perfect fantasy angel has the big tits and pretty face you love so much, but she’s also got something extra: a big ol’ dick between her legs. Sorry, wifey, but tonight may be a good evening to spend with DreamTranny.DreamTranny.com is a site with history. They’ve been around since 2000, making them one of the older shemale porn operations on...

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Trannie walks home after the club

True story. After visiting Sweet Wednesday Club in Kings Cross and the Trannie Shack I was walking to the train station. I had sucked around 40 cocks already. I had sucked 3 arses and also kissed around 10 balls. I was wasted and tired but looking for more. I had a fishnet tights with suspenders. A pink v-neck halter neck top. My small perts boobs were showing through. I had strappy sandals and a brown boob cardigan on. I felt slutty and had my hair all out over my face. My eyes were amde up...

A Goth Boy s Hot Tranny Fantasy

So, dude and dudettes, rock on. Well, your boy BigBabyBrett has one hell of a fuck story for you. Well, as you know, my band The Ministry of Evil was touring the states, and we came to the hellraising community of Waterloo. So, we set up shop in McElroy Auditorium, which was on the ground of some cattle congress bullshit, oh and trust me, with what i am gonna tell you, a lot of beefsteak was shared. So, we rocked the place out. During one of the Ministry's hit songs, as i was rocking to the...

We follow what happens when a petite bi guy that dresses as a tranny is regularly fucked by his neighbour

The best thing about living by yourself in the suburbs of a city, is that you have all the varied amenities of a city, with plenty of quiet roads, dark alleys, and gardens to melt into which serve my sexual leanings very well! If I explain to you a little about myself and exactly what my sexuality is, perhaps you’ll understand more fully? My name is Adrian Cooper, I’m 27, single, 5ft 6in tall, and weigh 10-stone (140lbs). Although I’m very slightly built, nature has been...

Tranny Sex Therapy

All at once, Maria’s limp lady stick transformed itself from lifeless shell into The Incredable s/he Hulk. I had to keep opening my mouth to keep it all in. Precum started to pour down my lips and chin onto to my bra. That precum was rapidly replaced by genuine girlie man paste. I would have been laughing but it was like being water boarded with seamen. I was drowning in hir cum. Holeee SHIT! ******************************************************************************** I swear I should...

trannie s beach photographer

I was looking to tranny photos on the beach so I started to think what if I was that photographerWho shoot those photos .... and wrote this. ...Nice ass and cute dick ... mmm if I was the one who's take that shoot ... I will slapping your ass and squeezing your dick and balls hard while I do that I would kiss deeply and suck your tuong ..mmmm yummy and bit your lips nicely mmm.. in turned you around and start massaging your asshole mmm what a tight asshole mmmm and so sweaty ass mmm.. you're...

Tranny Sex Therapy

All at once, Maria's limp lady stick transformed itself from lifeless shell intoThe Incredable s/he Hulk. I had to keep opening my mouth to keep it all in.Precum started to pour down my lips and chin onto to my bra. That precum was rapidly replaced by genuine girlie man paste.I would have been laughing but it was like beingwater boarded with seamen. I was drowning in hir cum. Holeee SHIT!********************************************************************************I swear I should have...

Tranny Wife Me

I have always loved sex with trannies, even more than sex. Friendship and closeness that I would struggle to fin in a guy. My wife had no huge preference for Tgirls but she did have a ravenous appetite for sex and was curious enough to try everything. We decided to go to Manchester and their regular Saturday night Tranny evenings and from previous visits, we had a few drinks in Napoleon's Lounge. It was a popular meeting place for "girls." Trannies who liked other girls, trannies who preferred...

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...

Trannies feminize dandy boy part 3

Ever tried getting unnoticed along a corridor with nothing on except a football top which doesn't even cover your bum and knowing there's cum oozing out of your crack? Well that was me in this Rugby Club after I'd had my ass stuffed by 36 virile players in the showers. I was trying to find my clothes which had been removed from me in the heat of the excitement as they were homing in on my soapy slit with their raging dicks. There was one door behind which I could hear a great hubbub of noise....

Messin With The Wrong Trannies

Messin' With The Wrong Trannies By Texzilla Milo Schullenberg stumbled into the apartment first, followed by his equally tired and sweaty roommate, Dave Angelo. The two athletic young men drop their racquetball paddles and head towards their living room area. "Not on the couch!!" Dave yelled. "Use your video game playing chair. It already smells like your sweaty ass." "Good point," Milo said falling onto the couch anyway. "I'll do that next time." "What were the advantages...

The Cabbie and The Tranny

The Cabbie and The Tranny By Michele Nylons Twas the middle of Manchester one winter night; and the only cab on the rank, The driver was reading a 'Score' magazine; whilst quietly enjoying a wank. He was dreaming that Venus was kissing his penis; and the shaking was making him tired, When a tranny called Lena, with false tits like Sabrina; came over and gently enquired. "How much to Oldham" she said; well the cab driver nearly dropped dead! He got such a shock he let go of his cock;...

First tranny

I’d been single for a few months and having the shittyist of luck on dating sites. I was unemployed and making some deliveries to the gay community for some extra cash. One of my regular stops was to a tranny named Tory she wasn’t bad looking and she never made a move on me other than asking if I’d like to hangout for a few minutes. Anyway I’d seen her on one of the chat rooms on a dating site... now I’d been without sex for at least a few weeks and I got a little curious. I started...

Tranny Motel

Tyrone and Kimberly Woods kissed as all of the guests at their house party cheered them on. It was their first anniversary and they were celebrating this night with family and friends. There were close to forty people in attendance – most of whom had brought some form of alcohol and all of whom had brought a gift. There was great music and excellent barbecue as Kimberly’s dad and Tyrone’s uncle manned the grill. Folks were laughing, dancing, and having a great time. In one corner of the yard,...

My black tranny wife part 3 final

Heather's dress or lack of was amazing. It was white and floor length in the back. It was open down far enough exposing half of her tight ass. The front was cut open down to her naval it was covered in very sheer lace, so the inside of her tits and her cleavage were easy to see. From her waist down, it was also open. She was wearing a sheer G-string. She must have been excited because you dick was semi hard and it really filled out her panties. If you looked close enough you could see her dick...

Flat Mates Chapter 2 My first visit to a Tranny Club

FLAT MATES Chapter 2: My first visit to a Tranny Club Having told Gloria that everything was "cool" between us, she then proceeded to shock me with her next statement. "If you wouldn't be embarrassed to be seen out in public with me," Gloria continued, "why don't you come with me to the club tonight? The band you say you like so much are playing again and I am sure you would enjoy yourself." "I'm not sure," I answered. "I would really like to hear the band but I'm not confident...

Trannys Feminize Dandy Boy Sequel

So being feminized is a sort of intimate experience? Believe me it's more than that! In fact I don't know how I can say everything about how I feel now or then when it started happening to me. But that's how my life goes. Things tend to get done to me. However much I try to regain control of my life I find others dominate me. For those of you who haven't read my story so far it is basically this: I was an effeminate schoolboy and all my friends knew I was not cut out for macho things. Then one...

Train Trip With Trannies And Laborers

I was regretting my decision to stuff in the train compartment at midnight. But I had to get to a warehouse 4 hours away by train because my supervisor made an ordering mistake. I packed light. It was after Dussehra, so the only train was packed. The general had people hanging from the doors. The sleeper wasn’t much better. I inched ahead to find a seat. But every seat and floor was taken by loud, sweaty workers in just Bermuda or lungi. Being bisexual, I was turned on a bit by their half-nude...

Tranny in Croatia

I started crossdressing as a teenager. I had a young mom, who always had some interesting and sexy clothes. I was 13 the first time I took her clothes (she was 31 at the time). I took a metallic silver jacket and some lacy thongs, and I put on her pink lipstick. I took a couple of photos, but they all came out blurry. But I liked how it felt, the only trouble was I did not know what to do... it felt wrong enough to hide it but right enough to get me interested. I dressed up quite often, but not...

First time with a Tranny

Stevie had always found it relatively easy to get girl friends. Not all had been good experiences. He always felt that after sex he just wasn’t satisfied. Maybe he wanted something different. Some people are perfectly fine about being gay or bisexual, but for others, it is a scary mine field. Stevie was one of those people. People had commented on him being gay for years and he always felt ashamed. He denied it, of course, but as time went by the thoughts about the whole subject haunted him. He...

Stag Night Tranny Gang Bang

I really still don’t know why, to this day, i said i would go with Ross to the Stag night. It was probably one of my more stupid decisions in life!! I’d met Ross a couple of times before, mostly at the S Club in Merton. Ross was about twenty three, really good looking, and loved the whole cross dressing scene but didn’t dress himself and described himself as an ardent ‘admirer’. He’d approached me at the bar one night and we’d got talking. Although I was much much older than him it only seemed...

Stag Night Tranny Gang Bang

I really still don't know why, to this day, i said i would go with Ross to the Stag night. It was probably one of my more stupid decisions in life!!I'd met Ross a couple of times before, mostly at the S Club in Merton. Ross was about twenty three, really good looking, and loved the whole cross dressing scene but didn't dress himself and described himself as an ardent 'admirer'. He'd approached me at the bar one night and we'd got talking. Although I was much much older than him it only seemed...

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...

Couple Finds Another Plus Tranny

While I was in the military, there were many opportunities to see some of the wild and crazy sites and people of the world. One time in Japan a bunch of us in a mixed group (men and women) went to a show that featured transsexuals. These were men who now dressed and acted like women. All of the men/women featured had breast implants to additionally make you believe they were real. The show was very exciting with each of the trannies on stage showing us they were as good looking without their...

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...

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...

Advice for dating a tranny for the semi straig

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...

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....

FIRST TIME TRANNY

It was pretty dingy in here, the sunlight came through a old dirty high window and a single fluorescent tube did little to lift the overall gloom. An oppressive smell of stale piss also hung over the whole place. What was I doing in here? In truth I did not know but I was 16, horny and wanted to find out about the rumours about sexual activity. I was still a virgin and although had messed around wanking at home, I was very naïve. I walked into the last cubicle, shut and bolted the door, took...

Extreme Mature Tranny Prostitute Story

"Hi honey, are we all set?" "Yes babe, I'll be round in about half an hour" "Is it as we planned?" "Pretty much, yes. Are you dressed as I said?" "To the letter, hon" "Good. I'll see you in about 30 minutes. Thanks for this." "No : thank you". Dave was such a good, regular client. He always phoned when he said he was going to phone and never let me down for a meet when he had booked. Once he had booked an hour of my time but had hAd his shifts changed at work, and he had worked nights the night...

My meeting with tranny milf Sandy 54 part 1

Wanna tell you about my meeting with Trannymilf Sandy 54!I met Sandy through an add in a pornographic magazine I was 23 then so she was 31 years older than me. Wanting for long to meet a much older tranny beauty I got really excited when she agreed to meet me. We met in her apartment after I rang the doorbell a beautiful woman in her midfifties with a white dress long blond hair,white nylonstockings and white high heels opened the door. Her face had a heavy-makeup I was stunned by her looks....

A Tranny Tale

I was invited to a small tranny club in Brighton, a few weeks ago, to be maid of honour. A few girls and gg's were expected to attend and I was to be used as a cumbucket towards the end of the evening to make sure all the punters went home happy. So I figured, why not.I agreed of course. I was feeling very femme at the time and needed a good fucking. But there was to be no rough stuff, I did'nt want my pussy ruined. I wanted to keep it in nice conditiom in case Bibi wanted to use it when...

FIRST TIME TRANNY

It was pretty dingy in here, the sunlight came through a old dirty high window and a single fluorescent tube did little to lift the overall gloom. An oppressive smell of stale piss also hung over the whole place.What was I doing in here? In truth I did not know but I was 16, horny and wanted to find out about the rumours about sexual activity.I was still a virgin and although had messed around wanking at home, I was very naïve.I walked into the last cubicle, shut and bolted the door, took my...

Tranny Attack 2

Thanks for the great feedback. Here is part two. I encourage you to send in more ideas of what you would like to see happen. “You’ll be hearing from me again, sweety!” With those words Julia had kicked me out of her apartment. I dragged by bruised and ass-fucked body home. Thankfully, Jane was not back as yet. All through the journey back to my house images of the previous night kept playing through my head. Discovering Julia’s cock, of being tied up and buggered, of sucking her cock, and...

First Bareback With A Tranny From Da Street

I know, I know, you guys must think that I'm CRAAZZYY!! Specially since I have this hangouts and hookups here in South America, but maaann!! These gals are really worth the risk (YOLO!! LOL).. also to be fair, most of the people tend to exaggerate about them..Anyway, here's the thing.. I was just walkin' from work, goin' home and well, If you follow me, you'll know that I live in a hotel room I rented in Downtown.. then I saw this gorgeous tall blonde gal from Streets doin' her "lil turn on the...

Tranny Attack Ch 02

"You'll be hearing from me again, sweety!" With those words Julia had kicked me out of her apartment.I dragged by bruised and ass-fucked body home. Thankfully, Jane was not back as yet. All through the journey back to my house images of the previous night kept playing through my head. Discovering Julia's cock, of being tied up and buggered, of sucking her cock, and of having Julia piss on me. And it was all on camera! And who had she sent the videos to? If she blackmailed me, what would I do. I...

Two trannys dominate me

I never thought of a day that I would be involved in a threesome. Especially a threesome with two trannies. It was lonely bar night for me, nothing special. I sat drinking all of my problems away. The rum and cokes were strong that night. I sat thinking about my life and wondering if life could actually be enjoyed. See, I was always that person who thought living a mild manner, do goody, life was the correct choice. But then why was I here drinking my life away? Something was missing. I...

Tranny

What do you think “Sluts with Nuts 4,” “One Hung Bitch,” and “My Girlfriend is my Boyfriend” all have in common? If you guessed they all had tranny babes doing kinky shit, then you were right. All of those titles are from DVDs that you can view for absolutely free on the site I have for you this time around. What’s not to love about watching some thick dicked chick fuck some hot bitch in the ass? I get that it’s not everyone’s cup of tea, but damn you’re missing out on some good shit if you...

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Tranny Boy Posse Tales of the Evil Fag Hag

This is just a story, okay? I don't advocate having sex with underage people and I realize that probably most cross-dressers aren't gay. Yeah, and most females who choose to hang around gay dudes aren't evil either. Most 'fag-hags' seem to be nice people and some may even resent that term of endearment. And it's never been my intention of slandering the Vegan lifestyle, Wicca, Druids, the rest of the occult and all the other great religions of the world. This is just a story, okay? It...

SARAH S NINE INCH TRANNY

For the last week my man has been tempting me with images of hung trannys. They have an added dimension when it comes to sex - tits and a cock, preferably both in generous doses. By the end of the week I am hanging out to experience a new one. One of the images he showed me was a side on shot of a tranny in panty hose with her back to the wall flaunting a huge erection thrusting out of her panty hose that really piqued my already strong libido. Another was a pic of tall slim tranny sitting...

SARAH S NINE INCH TRANNY

For the last week my man has been tempting me with images of hung trannys. They have an added dimension when it comes to sex - tits and a cock, preferably both in generous doses. By the end of the week I am hanging out to experience a new one. One of the images he showed me was a side on shot of a tranny in panty hose with her back to the wall flaunting a huge erection thrusting out of her panty hose that really piqued my already strong libido. Another was a pic of tall, slim tranny sitting...

TRANNY THREESOME

“Ask me again baby,” he groans as he supports himself above me on his hands and toes and frantically slides his full eight-inches into me. “Would you like to blow a tranny while I watch?” “Yes, baby yes, so fucking good, yes,” he moans as we orgasm together. I had just the tranny, Rosie, in mind, I hadn’t told Roger but she propositioned me recently and hinted that she would enjoy me and Roger at the same time. We always go to some trouble to dress or undress to turn on our guest when they...

Slovene Tranny and Her American Men

Milena Dorin awakened from her slumber. She grabbed her iPhone and pressed the button to see the time. It was 6:14 a.m. She decided to get up and bathe. She walked into the master bathroom of her palatial two-bedroom, two-bath downtown condo. She pulled her douching apparatus from beneath the sink. She cleaned out her 40-inch ass. After completing that task, she hopped in the shower. The steamy, hot water felt good against her milky-white skin. She scrubbed her curvaceous figure with a purple...

TRANNY THREESOME

“Ask me again baby,” he groans as he supports himself above me on his hands and toes and frantically slides his full eight-inches into me. “Would you like to blow a tranny while I watch?” “Yes, baby yes, so fucking good, yes,” he moans as we orgasm together. I had just the tranny, Rosie, in mind, I hadn’t told Roger but she propositioned me recently and hinted that she would enjoy me and Roger at the same time. We always go to some trouble to dress or undress to turn on our guest when they...

Riverbank Tranny Fucktoy

Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river. It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site. I had been chatting to Fillipe for a couple of hours, and we were both getting hornier and hornier with each new message that we sent. It was me that asked if he would like to meet that night, and he of course said yes....

Sissy Tranny Annie Slutty Fantasy

I have been dressing since an early age, dressing in my mothers stockings, suspender belt, bra, panties and heels. I used to feel my smooth legs and my cock would get hard straight away. I love how my cock looks when im dressed as a sissy slut and from that early age all ive ever wanted is to have a horny guy in front of me, with his cock hard knowing that he wants to fuck me. My fantasy and dressing got a lot more sluttier when I first in with my first love. Her name was Claire and she loved...

My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the...

My first time with a tranny

I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.In August 2007 I was 24...

4way Two sexy trannys Me and a simp

Why Hello boys It's me your sexy Latin bitch, Blue Latina here to tell you a wonderful story about one lucky boy, me, and two sexy transexuals that I think any straight man would have fucked. But first I would like to thank you guys for the wonderful subs and the sexy messages. I'm so sorry if I can't get to all of your sexy guys, I realize that I get a lot of single guys who message me who are lonely and looking for someone to tell them that they matter in a world where most women don't give a...

Young Tranny at Great Grandma s Funeral

“What’s going on,” inquired the 34 year-old construction and building inspector.“Nothing,” smiled the high school senior with the 22-inch dark brown wavy hair extensions and gray contacts. “What’s up with you.”“I want summa that.” he leaned forward trapping her between his heaving chest and the counter.“What?”“That sweet potato pie over there,” he winked.“Oh, okay! I’ll cut you a piece.”“You do that,” he said not moving an inch and running a forefinger down her weave.She darted her eyes away,...

Threesome with a tranny and a woman

I have a friend with benefits that I have been with for a few months. Her name is Bree and she is a tranny. I figured out I was Bi a few years ago so I started looking around for guy's to have sex with. Like others, I found guys who seemed to want to get together but would not pan out for some reason or another. That's when I discovered tranny's and new I wanted to be with one. So I started to look around for one and that's when I met Bree. She was beautiful 5'3" tall, dark hair and a tight...

Nate and his tranny neighbour

My first ever story. Depicting sex between a man and a transsexual.It is lengthy but personally I enjoy these best. Constructive feedback is greatly appreciated, so feel free to write to me. Enjoy ; )Nathan (Nate for short) was an average eighteen year old boy; liked girls, sports, partying, and being on his summer holidays he enjoyed the time off school. With some exceptions to the average rule, he loved his kinky dirty thoughts and porn. Frequently watching shemale porn, gorgeous busty women...

Sex with 2 Trannys in Amsterdam

Thanks for reading my first ever story I hope you enjoy it. This story is 100% genuine and describes my first ever experience with 2 sexy and naughty TV's. I am a 25 year old bi male 5'11'' normal build, good looking with a 7'' cut cock. I'm usually straight but after a few drinks and poppers, men and especially TV's get me so horny. A few weeks ago I went to Amsterdam with a straight friend, it was not my first time so I knew that sexy trannys were available and had been with them twice before...

My first but not last encounter with a tranny

My Wife and I have been married for about 3 years now and have since recently, been looking to have our first experience with a she male. I met a girl online name Judy and after chatting for a while and exchanging pictures we agreed to a meet and greet. Judy proved to be a very sexy transgender with feminine features. Her highlighted hair was long and she had size B cup breast with a thick firm ass and long pretty legs. She was very beautiful and had an awesome personality. We sat down and...

First Time with Tranny

So this is the story about how I got my first experience being a bottom, and why it was with a tranny.I was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...

I m a Meat Packing Girl Tranny

I didn't go looking for a tranny, shemale, dickgirl, or whatever derogatory term a homophobic world has labeled women that happen to be packing a penis. In fact, while I had messed around a little with the man worm, back in college and with a drunken buddy a few times, I considered myself 100% a hetero male, in love with the female form and a total horn dog for a beautiful woman. I must admit, I've jerked off more than a few times to shemale porn on my computer at home, wondering what it would...

My Tranny Schoolgirl Fantasy

As I sat on my couch, i was thinking, "Being alone doesn't have good perks. Maybe if I wanted to dream something naughty, it might be cool." So, I closed my eyes, and I dreamed of a very naughty tranny schoolgirl who would do what i like. All of a sudden, I heard a sexy female voice say to me, "Hey Brian, you bad boy, you big stud." I woke up, and there was this hot tranny girl who was dressed as a naughty tranny schoolgirl. She had nice lovely pigtails, a very sexy tied tight white top, in...

My first time as a bottom and with a tranny

So this is the story about how i got my first experience being a bottom, and why it was with a trannyI was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...

Nate and his tranny neighbour Part 3

Nate and his transsexual neighbour part three, as always hope you freaks enjoy and let me know what you think ; ) Nate woke up thinking about his last two encounters with his hot big-dicked neighbour. Having never had much experience with woman to having the hottest sex he could hope for was a dream come true. However as he slowly stroked his hard morning wood he realised he had yet to fuck Jez, her gorgeous tight ass in lycra was a vision to behold. Wanting nothing more to feel her pretty...

Fun with a latina tranny

So I'm a big fan of a big tranny cock in my ass. Just throwing that out there early on here.So this past summer I decided that with my school being off I should get some tranny cock as fast as I could. I went on a site and set up a new account, hoping for the same luck I had a few months ago with a hot black tranny named Jade and her friend. I quickly found a very nice 20 something tranny names Maria who said I would do. We went through a few chat sessions, with our cams on and I convinced...

Amy The Tranny Chapter 1

I met Amy at an adult theatre in town.She was dressed to nines in a mini skirt, tight halter top, and pumps leading up a pair of fishnet clad legs. I invited her into a private boothand once inside, went over her price for someadult fun. She told me I couldn't fuck her as shewas on her period but I knew something was up and asked her flat out if she was a tranny. She looked at me wearily and slowly nodded her head. I assured her I was into tranny sex and she relaxed and asked if I was into just...

Tranny Delight

I had been feeling particularly horny one day and waiting for Joe to come home I got to thinking about having sex with a black woman and then watching as Joe took her and then thought even more that perhaps a black tranny might be a bit more fun. So when Joe came home I easily talked him into going down to the alternative nightclub we had visited once before and off we went. Upon entering the club I saw that it was as crowded as usual and Joe and I took up a small table and settled with our...

The Perils of Pauline Tranny at the Truck Stop

Paul sat behind the wheel of his Mustang, the windscreen opaque with heavy rain. It had been raining hard for the last hour and he was hoping it would have stopped before he reached the truck stop. He looked through the windshield as the wipers lazily swept back and forth across the glass. The sodium vapour lamps bathed the parking lot in an orange hue. The blacktop was slick with rain and puddles had formed in the numerous potholes. The lot was quiet; as it usually was at 8:30pm on a Tuesday...

Tranny in Toronto Chapter 2

Introduction: Read first two stories on my profile. I cant seem to find the conversation we had by e-mail. ~~~ Since I lost my virginity to a couple I met on Craigslist (read my past story) and I not only had a wonderful time, but got paid as well, I decided to post my own ad on Craigslist. It was a simple ad, a tranny in Toronto looking for fun time. He saw my ad on Craigslist and decided to message me to see whether or not we could get together or not. His name was Marc, a young black boy...

My first time with a tranny

It happened on a Monday morning. After waking up with a throbbing hard-on. I called up my regular booty call. But she couldn't make it. Because her husband stayed home from work that day. So I decided to browse Craigslist, looking for someone local. After posting my ad, looking for NSA sex. I sat back and waited. Within minutes, I received over a dozen new messages. But none of them really appealed to me. Then after a few hours of receiving numerous messages, from both women and...

Tranny in Toronto Chapter 2

~~~ Since I lost my virginity to a couple I met on Craigslist (read my past story) and I not only had a wonderful time, but got paid as well, I decided to post my own ad on Craigslist. It was a simple ad, a tranny in Toronto looking for fun time. He saw my ad on Craigslist and decided to message me to see whether or not we could get together or not. His name was Marc, a young black boy who lived in Scarborough. He said he was a shy guy, a virgin, and he watched a lot of tranny videos...

Alan Gets A Tranny

-------------------------------------------------------------------------- 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...

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...

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....

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...

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...

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...

Build a Tranny

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...

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...

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...

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...

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...

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...

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,...

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...

Sex with 2 Trannys in Amsterdam

Thanks for reading my first ever story I hope you enjoy it. This story is 100% genuine and describes my first ever experience with 2 sexy and naughty TV’s. I am a 25 year old bi male 5’11” normal build, good looking with a 7” cut cock. I’m usually straight but after a few drinks and poppers, men and especially TV’s get me so horny. A few weeks ago I went to Amsterdam with a straight friend, it was not my first time so I knew that sexy trannys were available and had been with them twice before...

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...

Spoiling Tranny Niece

Brittney York opened her eyes and groaned. She looked at her phone and saw it was 3:42 in the morning. Some idiot was ringing the doorbell like crazy. She wrapped a lavender bathrobe around her compact, well-proportioned yet pudgy body. She grabbed a wooden youth-size baseball bat and went to the look outside. Brittney kept the porch light on at night so she was able to see if was her maternal uncle, Al, when she look through the peephole. She snatched to door open. “What do you want?”“Damn,”...

Young Tranny Ch 6 Vegas Sugar Daddy Pt 2

Young Tranny Ch. 6 Vegas Sugar Daddy Pt 2.This is the second 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!!!!Saturday, a week later, we met again at the Power Trade and had more mind-blowing sex and...

My tranny lover

I met Angel a couple years ago and fell for her right away. I was out at a club alone looking for someone to have some fun with. Then across the room, I saw her, she was the hottest woman in the place easy. She was about 5'6" tall with long black hair and a perfect 36-24-36 body. At the time I did not know she had something else but I would find that out later. I walked over to her and asked her to dance. She looked me up and down and smiled then said, "I would love to dance sexy." I took her...

tranny tart ride

hey - so my imagination runs wild when i am in tranny mode and i can't help to think about hard cock to suck and fuck - i am so addicted to my gender bent life style that i have these yearnings for erotic entertainment as fem fatale - get my franny on and pleasure other cd lovers - whether they dress or not - always great to gobble gay dick in crotchless pantyhose but naked men can be so very sexy with their fleshy bodies and their sweet boners just begging to be satisfied so after a ride...

My date with a tranny

I had been alone for a while and I was really horny. I am not the best looking guy but cute and a little over weight. I am 6'1" tall and about 280. So going to a bar was not going to work so I started to search craigslist for some one. I found a couple women but after emailing them I found out they all wanted me to join some web site and I was not looking for that. So I kept looking and I found a woman who was real and interested in me after we exchanged emails. So I set a date with her to get...

My first tranny experience

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...

my first tranny

[i[/i]im donnie, i had just dropped my girlfriend of at shipyard to work graveyard shift. i wanted to have a drink in bar, not a beer in a parking lot. as i drove toward the bridge i saw a cocktail sign, u know a cocktail glass. so i made my way to that street and pulled up in front of "the black rose". i went in and sat at the bar and ordered shot of jack and a bud. ik looked around and thought i died and went to heaven. all i saw was tits and leg and pretty women. i was enjoying the view...

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...

beautiful tranny

This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong?Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s not that I should worry about! Men of my family have always been stocky, and thickset. So a big nose and stocky figure are not a trouble! I’m working in a Western City College as a tutor of English Literature. I...

Satin Tranny Bride in the Sun Part 2

A blushing bride I was not. I was all woman. I stood transfixed as I looked at myself. I was in awe of the creature I had created. I had feelings I'd never felt before. I was horny, yes my cock was rock hard but I felt more. It was pure lust. I had a hole and I wanted it filled. I wanted a man inside me. I needed a cock inside me to make me his and I needed it now. I was aching. I was snapped from my trans by my phone. It was 11 am and Phil was parked in my driveway. I thought I'd be nervous...

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