Tranny
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“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...
“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...
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...
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...
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...
My wife is a real Romanian beauty, with dark brown long shiny hair, a beautifully build body, a face like a perfect supermodel and normaly the right attitude for sex. My friend Paul always says that she is an absolute stunner. And yes, he is right. She is very thin, weighing only 96 pounds. Her legs, tammy and ass are just perfect for her 27 years and her great dragon tatoo over her tummy and tits is amazing. The only draw back are her small 32AA cup tits which are even at this size a bit saggy...
Street Hooker Part 1After booking in at the hotel in a smart suit and heels, I returned to my car to get my 'things'. My two bags seemed excessive for an overnight stay but this was a stay with a difference. The hotel was perfect. It was just out of the centre of an unfamiliar (to me) town and on the fringe of a rather run down area. I was starting to get that butterfly in the stomach feeling - the buzz of daring adventure and excitement in anticipation of the evening and night to come. Each...
Keywords High HeelsCategories Bondage TransgenderingSynopsis I was getting too old to hook, profitably?so?. This is really a love story.The Old HookerBy Janet BakerThe flight to Amsterdam was uneventful, I laid back in my first class seat and let the handsome young attendant serve me champagne -- glass after glass. He was a darling. This old hooker would have gladly given him a freebie. I was only fifty but business was slowing down and I could see the...
this story is written by Molly Day, it is autobiographical. I'm just pasting and copying it here.https://storiesonline.net/s/20590/becoming-a-hooker################################Sometimes, in the middle of doing it, I find my mind drifting: trying to figure out how the hell I got here.I’ll be on my knees in an alleyway, or squeezed into the footwell of a car that’s far too small for what the owner intended to do in it, and I’ll think: when you were 14, Molly, is this how you expected things...
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...
~~~ 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...
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...
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...
Most of my life, I always figured hookers were druggies. Never even questioned it, a hooker, must be that she's an addict that can't function in the real world and just fucks to get more drugs. Makes sense, right? Well, not really, but that didn't matter because I never really cared to think about them. Unless I was roleplaying as one for my husband, but that's different. I'd dress up for him and we'd pretend that he was picking me up off the street and I was just some college girl trying...
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...
First Time Hooker As I came to a stop near that almost deserted corner and rolled down my passenger side window the girl approached me. Something about her gave me the idea that under all of that makeup that she was quite stunning. Her shorts were very short and they were very tight as well. She had on a skimpy bikini top that just barely contained her nipples. Her heels were so high that they looked like stilts. She leaned into my car window allowing her big breasts to droop down...
Keywords High Heels Categories Bondage Transgendered All Sorts of Stuff Synopsis I was getting too old to hook, profitably...so.... This is really a love story. Be aware that in the course of writing this story no animals were?in any way injured. The Old Hooker By Janet Baker The flight to Amsterdam was uneventful, I laid back in my first class seat and let the handsome young attendant serve me champagne -- glass after glass. He was a darling. This old...
This happened back in the Fall of 2016. I don't remember the exact date, but I know it was already getting very cold.-----------------Daddy Jake has a big, beautiful cock. He had been fucking me for over a year now. I craved his big, hard, throbbing cock all the time. It was one of the best cocks I ever had. I loved it.But Daddy is married, so he could only fuck me when ever he could get away. One day, after daddy ravaged me like the cheap whore that I am, daddy brought up one of his...
It was light when I woke up. I lay motionless looking at the ceiling, turning my eyes to the red and gold shade on the window. I was back in my room. in my bed, and I'd slept deeply. I was flat on my back, arms at my sides. I curiously touched my legs and slid my hands up my thighs, past my hips, and across my stomach. The sensations were strong, and I gasped as I touched my breasts and nipples. I inhaled and exhaled, filling my lungs. I was overcome by my new body, and I loved...
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...
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...
I dressed in her bathroom. Comfortable nylon stockings and my black body with suspenders, black thong, my beautiful silicone breasts in C-cup and between blond wig with ponytail up on my left shoulder. High heels had to wait this time. Then I pulled on my red short dress in jersey. He who runs away from each other so good around my body and butt and let my tranny cock visible as a bulge in the front. Her breasts hung heavy and stuck out in the red dress.She came out of the bedroom and met me...
This past Friday morning my phone rang. It was Chandra my tranny friend who I met and fucked some weeks ago. She told me that she had nothing to do this weekend and that her roommate was out of town and she was alone. I told her that if she wanted to get out of the city that she could spend the weekend at my place. She said that was a great idea and that she would be over in a few hours. When Chandra got to my place she was horney as hell. She dropped her overnight bag, dropped to her knees and...
TRANNY TALES... MY BIRTHDAY PRESENT FOR MY BOYFRIEND Like most of us 'girls' I have been dressing secretly all my life. Although it was only three years ago that I went into my passion a bit more seriously. When I could afford a place of my own that offered me the freedom and privacy I needed. I completely shaved my body, becoming nice and smooth full time, and expanded my female wardrobe. Building up from a couple of pairs of knickers to several complete outfits including heels,...
My Night As A Hooker by Tanya Fly Comments welcome. Let me tell you a story about a girl, a cheap motel, the hooker stroll, and some very sleazy clothes in my size. Natalie is the kind of girl you see in some rock video or beer commercial. Great T&A, tall, lots of long blond hair, and a wild, kinky imagination. We met in the city. I was a junior advertising "executive" (read go-for) and she was the knockout administrative assistant going to...
Sometimes, in the middle of doing it, I find my mind drifting: trying to figure out how the hell I got here. I’ll be on my knees in an alleyway, or squeezed into the footwell of a car that’s far too small for what the owner intended to do in it, and I’ll think: when you were 14, Molly, is this how you expected things to turn out? Tongue flat under a stranger’s cock, moaning and rubbing myself, about to cum as he fires his load into me, and clutching the few pound notes he pushed into my...
I guess at one time or other, some of you guys out there will have been with a prostitute. Perhaps your wife knew, perhaps she didn't. Perhaps you weren't married and just looking for sex without any attachments. Maybe you went by yourself, maybe in a pair or even a group. Perhaps you cared who she was, more probably you didn't. Did you look at her face while you thrust into her body, or did you take her from behind? - The reason I ask is that the prostitute could have been my wife or, if it...
The Walk after the Busted Date or My first Job as a Hooker It was a Friday evening about eight just before the sun was about to set on a pleasantly cool evening. The brisk air kept me comfortable since my body was a little warm from being nervous with the coming scenario. I was going to meet Phil, my date, as a hooker. We have been planning on this for a few weeks and our schedules finally matched enough to make it happen. The club I was going to served a very eclectic clientele and...
My wife and I have been married about seven years but have known each other since highschool. Paula was always cute with cute girl next door looks and a sexy little body that had curves in all the right places. Her breasts weren't overly big, a generous b'cup but they were always perky and had perfect nipples. She tried to work out when she could so she had some nice muscle tone in her thighs and ass but not enough that there wasn't a nice bumper covering her to give her a soft thickness that...
As described in at the end of this story: Deflowering Jeanette, I fucked Jenny with her younger sister Marcia watching us and fingering her virgin pussy at least once. I also alluded to Marcia becoming so jealous that Jenny and I were having sex and she wanted me to fuck her too Jenny and I had to find other places to have sex other than their house.This is the continuation of that story and the final chapter in this series of true stories.Throughout the rest of high school Jenny and I fucked...
So woke up this afternoon with the intention of seeing a hooker, i went into town and visited one of the famous walk ups in London, walked up stairs saw two doors, one with the name Amy, and the other Kate, i made my choice to see Amy and it was a choice i wouldnt regret, Amy is a curvy girl with black hair and a great pair of tits, D or E cups if i had to guess, she greeted me at the door wearing a short black dress which showed off her tits, she was wearing red 6 inch hooker heels showing of...
CATHLEEN. Diary of a lesbian hooker of the 1930s. PART 2My extra work on Friday evenings had never interfered with my job at the factory. The factory work was quite simple and since I had finished my secondary schooling, I was put in the office doing invoices, shipping notes, bank stuff, etc…I was one of ten clerks doing pretty well the same thing and we were supervised by an office manager who was an Irish girl like me but around 50 years old. She was about my height, a bony face with short...
CATHLEEN. Diary of a lesbian hooker of the 1930s. Part 1.This diary was found in an old hotel room in a city we will not mention. The writing is Cathleen’s but the dialogue is sometimes made up, although it would have been close to the original. Cathleen worked the joints in downtown Boston during the 1930s, the end of Prohibition, the great Depression and especially the golden years of the Mob. Any resemblance to people dead or alive is purely coincidental....
Daddy's Little Hooker© Shyblueeyes1968 2006-2009MF, teen(18+), i****t, spank, anal, oral.Summary: the Father, Mike, feeling frustrated, goes in search of young whore, and ends up having the shock of is life when the girl he tries to pick up, turns out to be his 18 year old daughter, unleashing his repressed i****tal desires. This story is based upon a series of chats and cyber chat with women, and incorporates various ideas from chatting to several women. However, it is fiction and none of the...
Bumfelt opened the door to his car and climbed in. He took the keys from a trouser pocket, turned the ignition and......the passenger door, suddenly opened. Bumfelt's hand went for his holster and the Colt. "Whoooah! Jesus, Theo!" exclaimed the hooker as she leant into the car. "It's me, Nikki. Fucking hell, I thought you was gonna shoot me." "I was," hissed Bumfelt. "Get in." Sexx climbed in. "Drive," she said. Bumfelt did. He put the car into drive and pulled away from the kerbside. "Where?"...
Sue was on her way home from work. She was driving in heavy rush hour traffic, but her mind was in turmoil. Since meeting Tim a few weeks ago, she had begun to question everything about her life. Sue Henson was a twenty something college graduate, who worked for a rapidly expanding Midwestern company. Her upper middle management position gave her a respectable income, and plenty of room for advancement. She owned a pleasant two-bedroom condo in one of the city's best high-rises. Although her...
Few months after getting married, my wife confessed a fantasy she had. Anita told she wanted to be picked up in the street as she was a prostitute.She put on a very tight black dress, a tiny thong and high heles.She looked gorgeous, ready to be well fucked in the streets…I left her alone in a dim lit street, where we knew usually few hookers were.I made a couple rounds in my car and got surprised as I saw several cars stopping and some men asking Ana what she was offering…But my sensual babe...
My wife Jordan and I have been into the swinging gangbang scene for a number of years.We would both go out on our own and fuck other people as well as attending swinger parties and organised gangbangs.Obviously Jordan fucked way more people than me. She had a few tricks to show guys she was a slut, besides dressing like one.At bars she would bend over wearing nothing under her dress. When opening her purse it was full of condoms and a dildo.Sitting on bar stools she would swing around with her...
Hooker or escort?The credit crunch was biting hard and my expensive tastes had not waned in the slightest. With each extravagant day I was getting closer and closer to financial meltdown, which is the sole reason I was standing in front of a full length mirror, scrutinising my choice of outfit. Tonight I would for the first time offer my body sexually for financial gain. Tonight I would be receiving cock solely for the purpose of creating wealth. Unashamedly the very thought of soliciting my...
------------------------------------ "What is that?" Carlie jumped at the unexpected intrusion. She'd had no idea that her brother Dennis was in town, let alone in her room. She'd been so caught up in what she was doing and sure she was alone that she hadn't even noticed when he walked right through her open door and looked over her shoulder. She quickly tried to close the browser. "Dennis! What are you doing here?" "Who is 'Apple'?" Carlie closed her eyes as her...
Mike was feeling increasingly restless. Susan, his 18 year old teenage daughter was staying at her friends, and he had the house to himself. Just him; all alone. Just him and the computer, with only his frustration and loneliness to keep him company. He was flicking through some teen porn pics, the one’s he liked, the one’s that he secretly knew, but his conscience self denied; most resembled his Susan. For a brief, unguarded moment, he allowed her to slip naked into his mind, his cock...
Introduction: How my wife turned into my Hooker Let me start off my saying my wife Aimee is absolutely stunning. She is 58, 105 pounds, dark brown hair, full C and a complete slut in bed. Aimee will do anything I can possible think of and she has a most twisted mind then I. Like last week I came home and she was in her old catholic school girl uniform (which she still fits in from 7 years ago) with a ruler in one hand and and a 12 inch dildo in the other. She said to me, Which one do you want...
Introduction: MY first be easy ******************************* Mike was feeling increasingly restless. Susan, his 18 year old teenage daughter was staying at her friends, and he had the house to himself. Just him, all alone. Just him and the computer, with only his frustration and loneliness to keep him company. He was flicking through some teen porn pics, the ones he liked, the ones that he secretly knew, but his conscience self denied, most resembled his Susan. For a brief, unguarded...
Introduction: This is a story about me being away and my wife comes dressed as a hooker. Absolutely not, I yelled at my wife. You dont need a $500 watch. I said as I walked out the door. That was the angriest I ever left my wife. She wanted to buy a $500 watch and she didnt have any money in her bank account. She expected me to buy the watch for her. Thats why we have separate accounts. We each have our play money and I wasnt going to use my money to buy her a watch. I did call her on the way...
It was 1986 and I was 21 and had been married for less than a year when my husband, Steve, came to me with a problem. Steve owned a painting business and had a crew of 6 mMexicans working for him painitng a new apartment complex here in town. Steve told me that if he could finish the contract a weeek early, he would get a huge bonus. He had promised his crew that if they finished early, he would rent a hotel room, buy them a few cases of beer and whiskey, and hire them a hooker for a party....
Hello ISS readers, this is Selena here. This is the continuation to the next part where I became a hooker. I really want to thank the ISS community for the overwhelming response to my first story. So let’s continue from where I left. So I wrapped myself in a towel and peeped outside from the bathroom door. I could only see Moin’s back. He must be talking to someone. I could hear 2 more guys talking to him. I came out and was in for a shock. It was Ali and Javed, my neighbors. They saw me in...
"Go to your corner, Samantha," the pimp ordered from the inside of his car. Samantha, or Sam for short, was his youngest and newest hooker. She was a small, busty blonde with a flare for the rough stuff. Her blue eyes scanned the area quickly before she allowed herself to exit the safety of the pimp's car. It was her first night on the corner of 5th and Main. The people on the streets rushed about in their efforts to get to the nearest bar, or they were seen taking another whore into a run-down...
EroticOne night sophomore yr I decided it was time to lose the V-Card, and I decided it the only guaranteed way was with a hooker. Just riding around with friends nights before I kind of had an idea of where there may be hookers. I ride around town looking for hookers. My idea of what I would find was based off Pretty woman and HBO specials, women walking around half naked. After 2 nights of no luck i do some research and find out that's not how it is. After research I had a good idea of where to...
Grew up in a small town. In high school I was on the football team, had friends, was a bigger guy, but not obese. i was naturally shy when it came to women so I was a virgin all through HS.Fall 2005 I move to a mid-size town for college. Still naturally shy when it came to women. All of freshman year I remained a virgin. Lame, I known. What kind of guy can't get laid in college.One night sophomore yr I decided it was time to lose the V-Card, and I decided it the only guaranteed way was with a...
Jon Douglas had been married for almost twelve years. He was pretty happy; he had a decent job, enough money to support his wife, whom he loved. But their sex life wasn’t great.To be honest it had never been that good at the start of their relationship. She was a bit too timid, even shy. This was why he had, for the past four years or so, visited hookers on a fairly regular basis.He liked to act out his fantasies with a really filthy-minded woman, and this was the perfect way to do it. Around...
Cheatingthe first and the last time i ever picked up a hooker , if you know me you know i love panties and bras and underwear in general . i was driving through the what you call the redlight district of the east end of vancouver bc when i saw a few hookers . observing them i take notice of what they are dressed in more than what they look like . there was this one in particular i had noticed , she was a bit heavy set and had big boobs and a fat ass . in one of my times circling around i noticed she...
Tears of pain pricked my eyes as Julia drove her huge black cock into my ass. In my wildest dreams I had never expected myself, an all-American straight white male to be in this situation, beaten, bound, and being ass-fucked by a transsexual with a huge cock. I am a normal sort of person, happily married, with two kids, and with normal middle-class values and behaviour. I don’t hate gays or blacks or anything like that but I don’t want them in my neighbourhood. My only fault is that I...
UltimateFantasyOne of my greatest sexual fantasies has always been to have my ass fucked by a nubile, horny transsexual. Being taken by a girly with a solid erection must be the ultimate sexual pleasure and I have often dreamed about how it would feel and how I would feel about it. The following is a story albeit it is how I would like this to happen.I met up with Carol and Ellen who were going to get me prepared for my anal screwing. They were both dressed in leather corsets with their breasts...
A true story…I’d woken earlier than I’d wanted for a rare day off from work and decided to see if I could have a little fun. So I did my make up and found the longest false lashes I had, touched up with the darkest mascara there is… with a touch of glitter… bright red lippy, a naughty smile, get the picture?I put on some sexy underwear and a black lace top, little skirt with heels and hold-ups… I was on the hunt for cock but how could I trick a complete stranger into some naughty fun with a...
Tears of pain pricked my eyes as Julia drove her huge black cock into my ass. In my wildest dreams I had never expected myself, an all-American straight white male to be in this situation, beaten, bound, and being ass-fucked by a transsexual with a huge cock.I am a normal sort of person, happily married, with two k**s, and with normal middle-class values and behaviour. I don't hate gays or blacks or anything like that but I don't want them in my neighbourhood. My only fault is that I cheat on...
Tears of pain pricked my eyes as Julia drove her huge black cock into my ass. In my wildest dreams I had never expected myself, an all-American straight white male to be in this situation, beaten, bound, and being ass-fucked by a transsexual with a huge cock.I am a normal sort of person, happily married, with two k**s, and with normal middle-class values and behaviour. I don't hate gays or blacks or anything like that but I don't want them in my neighbourhood. My only fault is that I cheat on...
After going to Trannyshack and dancing the night away i left the club at 2am. I was drunnk as guys had bought me drinks all night. A few guys had sat next to me and made me feel their cocks - all were nice and hung lads. The guys liked my long legs shaven with fishnets - black court shoes and and painted nails. I was wearing a short black skirt and low cut top. Long dangling earings and long dark hair. I was made up with smokey eyes - dark plum lipstick and lots of rouge. My lashes were thick...
This happened about ten years ago and I thought I'd share it with you all for your enjoyment and mine! Like I've said before, although I'm bi-sexual, I don't walk around checking out other guys, nor do I like to be intimate with one. Sure, some might consider taking a cock in the mouth or ass intimate, but I consider it just sex. When I say I'm not intimate with other guys, I mean I don't kiss or cuddle or anything like that. It's always just sex, with no strings attached.......usually! There...