Shemales Porn Stories
Page 76

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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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 10 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 4348  |  
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Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.

There is no cross dressing in the story but this is how I began my transformation from
regular boy into cock suckking teenage crossdresser.

We were having a really hot heat wave. i meat with my older b*****r (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going to the movies by myself but I really did want to see that inception movie. I looked up whe... Continue»
Posted by srlvictoria 1 year ago  |  Categories: Anal, Shemales, Taboo  |  Views: 3015  |  
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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: 4145  |  
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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: 3026  |  
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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: 2101  |  
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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: 4020  |  
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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: 14324  |  
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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: 758  |  
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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: 552  |  
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THE TRAIN JOURNEY IN INDIA - PART II

well as you all read the ticket checker was in my cabin in the train

He was in his mid forties i guess and 5ft9 with a beer belly and chubby all over.

he was stared at me for a cpl of minutes and then removed his coat, shirt, pants and boxers. He had his back to me i couldnt get a view of his cock. he wore his pyjamas. I had meanwhile turned to face away from him and said "Bhanu did you lock the door?" and he replied "it is not Bhanu it is me Ramesh Sharma and I have locked the door !!". He had a gruffy voice.

I pretending to be shocked got up sat on the seat with my legs pulled up ... Continue»
Posted by hornyboyind 1 year ago  |  Categories: Anal, Shemales, Voyeur  |  Views: 550  |  
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Unexpected friends CD fantasy

There really wasn't any planning to what had happened. Earlier that weekend, I had just felt this strange urge, so I decided to check online for something different to do that was new. Of course, I had done parts of this before, but most of them were separate in their operation. I had never done anything sexual with anyone, though I had posed, and the only time I had gone out as this was to see if I would be recognized. Maybe that was what convinced me to except his offer, as I somehow felt that I wouldn't be recognized by anyone locally.

So I had agreed to meet with a man at 8pm in a rathe... Continue»
Posted by RosalynLee3 5 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 3651  |  
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3 Teen Cross Dressers Misadventure - Part 2

Here are 4 men all at least 6" taller than us with athletic builds; we really thought we were about to get our asses kicked and robbed. One man got up an opened my duffel bag and of course found all of my crossing clothes. "We have us a couple of fags don't we." He said, opening the other bags finding more of the same. We were silent until Sean said that we just do it to get a kick from people and that we weren't gay. They all stood up and one put the chain lock on the door. "You are tonight boys" Craig said. Yep we were fucked; way too d***k and no exit.Plus they started to swig the liquor we... Continue»
Posted by ClaireCD 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 481  |  
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Another Time Another Place Pt 1/3

Long Story but please stick with it (giggle)

INTRODUCTION

This is an account of what happened to me some years ago. The names have, for obvious reasons, been changed. Even now as I recount it, it seems like it never happened and, yet, I know it did.

Both my older b*****rs, being 10 and 9 years older, had been Boy Scouts in a troop where we had lived up until the time I was 6. The Scout Master, Richard, was my father’s solicitor and he had kept in touch, after we moved away, by writing and visiting over a number of years.

When I was 16, we went back to visit the area where we use... Continue»
Posted by charlottekerscot 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 396  |  
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the real me part 4

I took our ice tea back into the den.Mike an I were on the love seat kissing and fooling around.When our mothers came in an sat down too.We all talked and watched some tv show.When my mom and becky said they needed me to come upstairs for a few minutes.
The 3 of wentup to my moms room were they had me get undressed.They had me put on a white and pink full corset with white seamed stockings they hook the gartor straps to the stockings. I put on pair of pink stillettos and sheer white short camsole and sheer pink long robe.Mom and Becky figured know painties was best route.I looked at myself ... Continue»
Posted by cdpaula 2 years ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 666  |  
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An afternoon at the Mall

If you read my story "Sandy Comes to Visit Me" you will know that I finally was able to meet my friend Sandy, who was in town for a business meeting. You will recall that I had just graduated from the University and happily living as a woman, even though I still have my boy parts. You will also recall that I’m tall and slender, with long legs and a tight little bottom. I have longish sandy blonde hair and smaller breasts as I have only been on hormones for just a couple of years. All in all I am considered to be an attractive young lady.

Sandy is an incredibly spunky girl about my age, a ... Continue»
Posted by Rickicd 2 years ago  |  Categories: Shemales  |  Views: 592  |  
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