Shemales Porn Stories
Page 77

Str8 Guy Seduced By A Tranny (ch2)

For a str8 friend here at xHamster... who is a fan of my writing and when I told him I would write a story with him in it... I'm not sure he knew what he was getting into..

Chapter 2


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We entered my room, it is mid-afternoon, so it is warm; the sun is bright and there is a warm sweet scented breeze wafting in the open window... I always splurge and get the "nice view" rooms, and so, I was on the top floor of the hotel (only five floors) and had a balcony that overlooked the ocean, and yet, it was private enough that no one could look in.

He walked... Continue»
Posted by TomStone90045 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2450  |  
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Busted

The guy turned back and walked up behind me and whispered, "I like your panties."

I was so busted. I turned to him and said, "Excuse me?"

"It looks like those panties you're wearing are pretty sexy. Maybe you'd like to show me them."

My face burned with embarrassment. I tried to look away but couldn't.

"It's laundry day. They're my girlfriends," I said.

He laughed loudly. "Bullshit."

"Alright. They're mine. I like to wear women's panties. Big deal."

"Hey it's cool. I think it's hot. I'd really like to see what you're wearing under there."

I smiled and blushed. "Oh yeah?... Continue»
Posted by koolstuff 2 years ago  |  Categories: First Time, Shemales  |  Views: 2100  |  
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Dad uses me for his wife

After a long and unstable marrage of 20 years, the divorce papers finally came. My wife and I only had one c***d, William, and he is very gay. My wife was too much of a homophobic bitch to support him. Even when he was younger we knew he would turn out gay. Always wanting to wear girl's clothing, dress differently, speak differently, even walk differently. I always supported him as a dad and as his friend. I never understood and I still don't understand my wife and how she could just leave her only c***d and I. I remember it was his 18th birthday, about five months ago. She came home from work... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 3943  |  
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Online Hookup

Jamie Harris typed in the user name and password of his account with his favorite online amateur porn hosting site. He was alerted to a new message. He clicked the envelope icon and viewed the correspondence from screen name ‘DLdriller’.

Damn fembunnybttm!!! I wanna get in that ass. Where are you located? I think we stay close.

Jamie fired off a reply with his location along with his email address and the number to his spare prepaid phone. He logged off the computer and hopped in the shower before heading to work at the clinic where he was the administrator. Later that day, Jamie retu... Continue»
Posted by faggyboi 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1791  |  
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olderman and mature crossdresser part 1

It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all.
As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a couple bending over shots and eye contact.I made my way to the check out an seen him in other line.I finshed checking out when I got outside to load my bags in my car he was parked next to me.He spoke to me and said that he was sorry for following me around that he was not some kind of crazy killer but ... Continue»
Posted by cdpaula 2 years ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 910  |  
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Joanna Tranny Prostitute

Joanna stood on the street corner and casually shifted her posture from one leg to the other. So far it had been a quiet evening for her with few punters around. Not many girls were plying the streets either. She’d had one customer earlier. He had been an Asian guy in a Toyota who’d stopped asking for business and after she’d explained the she was a cross dresser and he had readily agreed to anal sex .He was young, quite handsome and had treated her with kindness and respect. They’d driven to a local builder’s yard that Joanna often used and after exchangeing the money and some small talk had ... Continue»
Posted by joannacd1 3 years ago  |  Categories: Masturbation, Shemales, Voyeur  |  Views: 758  |  
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SISSY DANI PART 1



I was not aware that my girlfriend had begun studying hypnosis,
nor that she harbored ambitions of petticoating me. But I soon
discovered that the combination of the two was dangerous to my
masculinity. One afternoon I was sitting in my living room,
listening to the stereo through a pair of headphones. It was a
warm, sultry day, and after a while I drifted off to sl**p. (Much
of what follows my girlfriend--now my mistress-- explained to me
later.

Seeing that I had dozed off, Jennifer saw her chance. She
replaced my music tape with one she had prepared in advance.
Through my dr... Continue»
Posted by alexwd0 3 years ago  |  Categories: Fetish, Shemales  |  Views: 562  |  
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The night I stayed in Nashville ( as a sissy )

I was traveling to Florida from Missouri to see my k**s. I new always stay the night in Nashville, and sense I would be alone in the hotel I thought I would pack a few of my sissy things. The thought had me hot the whole trip so I had to pull over early and slip into a rest room in a truck stop to put on some things for the drive. I put on some pink panties and stay up stockings, also a little camisole under my shirt. Wearing these under my cloths had me excited the whole trip. By the time I got to Nashville I was fit to be tied. ( literally )I checked into my hotel and started to get dressed ... Continue»
Posted by firstknightd 3 years ago  |  Categories: Shemales  |  Views: 1302  |  
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Completely Fooled

I could not have expected the encounter I had the other night. Having recently separated from my wife a buddy and I went out to a local pub for a few beers. While we were sitting at the bar deciding what beer to try next a very hot redhead comes over and sits next to me. We exchange hellos introduce ourselves. Soon begin to talk about the different complexities of the beers we are tasting. She is so sexy with small b cups and a perfect mouth. After a few beers my buddy decides to take off leaving Veronica and I to get ourselves. She is just a darling; her smile, her laugh, her sensual demeanor... Continue»
Posted by IndieMe 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 5274  |  
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Cheating Bastard

I began to suspect that my husband was cheating on me about 6 months ago. He'd call me and tell me he was working late or he'd show up to different events claiming that his boss needed him to finish a project before he could leave. Then his phone started to have more activity than normal. He'd often move to another room to take calls or messages. He started hiding his phone whenever he was asl**p so I couldn't go through it. The final clue came when he started to smell different. I had been married to him for many years so I knew his scent well but whenever we made love I could detect ano... Continue»
Posted by RyleighM72 11 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 4359  |  
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The Domestic Bliss continued ……

After my s****r told my Mother that I was wearing her clothes, Mother was just brilliant. Mother was tall, almost 5’10”, dark auburn hair, very light/white skin, freckles, very small breasts but fantastic figure and legs. When she made me her second daughter, I was more or less her build so I could wear her clothes and shoes easily.

She told me that I wasn’t in trouble but that she would have to think about the new girl in the house a little more. I was given permission to wear her clothes but only those that she had worn (she changed her underwear every day but that didn’t stop those li... Continue»
Posted by antoniaf 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 911  |  
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My Ladyboy- LittleLi- Part 2

After LittleLi had finished swallowing my cum, she fell back and i noticed she still had on her frilly ankle socks and MJ,s. Now that I knew LittleLi was a ladyboy i could tell her about my collection of stockings, panties, shoes and dresses that i liked to get dresssed in. LittleLi loved the the fact and took off the rest of my man clothes. I got up off the bed in front of her naked and went to my cabinet with all my fave clothes in it. I lay out satin frilly panties, stockings of all different colours and school uniforms with knee socks from Japan to England. LittleLi immediately ordered me ... Continue»
Posted by igglepiggle 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 1274  |  
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Finding a Great Roomate

I had just moved to the Great NorthWest and was lucky enough to land a job as a convenience store clerk working a shift from 8pm to 4am. Money was tight so I went to the classified to look for an apartment to share. I found one that was fairly cheap and close to my job. It was a two bedroom apt. and I would share the kitchen and common area with my roommate. I gave the guy a call and set up an appointment to see the apartment and be interviewed by him. I went to the address and rang the bell. The door was opened and there stood huge guy, well over 6' tall and I would say around 260lbs. H... Continue»
Posted by rikki50 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 4146  |  
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If you go down to the Woods today you`re in for a

This is a true story that happened recently- Summer 2013

This summer I had been looking online for places where one could go nude sunbathing near or around the city where I live. Luckily there was plenty of advice online and I soon found a destination which ticked all my boxes. I had never done this before but the thought of lying naked in the sun aroused me in an unusual way.

I`m in my forties and am a part time Crossdresser, possibly more of a Transvestite as I`m told I look quite good dressed as a woman. I like to keep in shape and am quite thin. I love to suck cock, be... Continue»
Posted by jimbo70xyz 1 year ago  |  Categories: Masturbation, Shemales, Voyeur  |  Views: 3029  |  
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Frank's Friend

Frank is a buddy of mine. We grew up and went to college together. While we were in college Frank and I went on a road trip from Lubbock to Dallas. We got to Dallas went to a few strip clubs and then finally found ourselves on Harry Hines Blvd. It was about 1 in the morning we were both horny and a little d***k. Frank pulls up to this leggy blonde in a short skirt and fishnet hose and asks how much. She told us she would do us for free for a ride home. We said fuck yes. Frank had me drive to her house while he had her in his lap, kissing and groping her. We got to her house and went i... Continue»
Posted by biguy52x 1 year ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 4019  |  
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Teacher was Hot For Me!

Was just starting my senior year of high school, and while everyone knew I was gay, I had only recently told my parents that I felt I was born in the wrong body..so for my eighteenth birthday my mother took me to the doctor and got me new breasts, and started me on hormones...and even though I would dress for drag shows, it was only a special occasion thing, but at this point I started dressing everyday..and school wasn't much fun on most days..lots of heckling and abuse from other k**s and even teachers..I did have one teacher who was cool to me, Ms.Riggs, she was always very sweet to me an... Continue»
Posted by smonkeys32 3 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1632  |  
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A little favour

Day 1 – Friday

My neighbor Kathleen called me up one Friday evening and asked me if I could come over to her apartment and help her with something. She lives in the apartment next to mine, so I went over there. She was sitting at the kitchen table talking to a girlfriend. They were finishing up a bottle of wine and opening up another one. Kathleen invited me to grab a glass and sit down with them. We sat around the table talking and drinking wine. We drank that bottle and then another one. I was definitely feeling no pain.

Kathleen spun one of the bottles on the table. It stopped and poi... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 15513  |  
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The Slave and the Sissy Part Seven

Honey was viewed like a new toy by her new master’s people as she was led whimpering to the ominous looking padded pole, the males jostled to fondle her soft white bottom and rubbed their erect cocks against her sweet little body at every opportunity; the womenfolk smiled with eager anticipation at the prospect of seeing a whipping; the sissies looked on with blank faces, having tasted the whip before. The males at the front howled with wicked derisory laughter as they viewed Honey’s little cock rising to an erection once more; despite having already spent herself generously twice before toda... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 763  |  
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Neighbourhood watcher (part 3)

I lit a soothing Black Sobranie cigarette, and gazing at the thick red sexy, shiny outline of my lipstick on the gold filter, pondered my next move. I've never done this before! What if I get found out? What if he tells my other neighbours? But all the time my head was being overruled by my throbbing, rubber covered cock. Lust took me over. After several more drags, my ciggie tip was as sticky with lipstick, as my cock was with precum. I had to stop myself shooting too early, so I tied my cock and balls achingly tightly with a shoelace. I switched my kitchen light on, and checked through the ... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Fetish, Shemales, Voyeur  |  Views: 461  |  
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The Slave and the Sissy Part Six

After watching the African depart with his new sissy, Ella turned to Slave.

“On the subject of Africans, you have an appointment to honour with Mistress Ayesha the day after tomorrow; make the most of your sissy tonight, I shall cage your manhood again in the morning in preparation for your visit. Pepper will manicure her when she arrives this evening to take you tomorrow, she will be my guest tonight as we have business to discuss; I’ll let her know of your fondness for each-other, I’m sure she’ll enjoy teasing you both about it, in one way or another.” Pepper gripped slave’s arm tightly... Continue»
Posted by midsummerman 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 551  |  
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