Shemales Porn Stories
Page 69

The Making of A Sissy-Part Four

After an exhausting evening Bella was made to wait at the door and humbly kiss the guests as they left; some of the males groping her pretty arse as they departed. She was glad of the alcohol she had been treated to as this masked from her the ugliness of some of the brutes she had been f***ed to entertain, though she remained reasonably coherent. Bella eyed the vase in which the phone was hidden, which was tantalisingly close. Jane ushered her into the embrace of one of the leaving males, who was also a little worse for wear; he cupped the sissy’s sweet little balls in one hand as he pulle... Continue»
Posted by midsummerman 2 years ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 795  |  
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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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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: 909  |  
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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: 3940  |  
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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: 4144  |  
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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 11 months ago  |  Categories: Masturbation, Shemales, Voyeur  |  Views: 3030  |  
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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 1 year ago  |  Categories: First Time, Shemales  |  Views: 2097  |  
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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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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: 2990  |  
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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: 2449  |  
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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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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: 536  |  
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What Happens in Vegas ( A trip to Vegas changed hi

Every year I go to Las Vegas for a convention and it is always a good time. I eat like a king, drink like a fish and spend like Rockefeller. I usually meet up with friend while I am there and play a few rounds of golf and go to a few strip clubs too but this year none of my buddies could make it. I was kind of bummed about flying solo but it ended up being the craziest and most memorable trip ever.

The craziness started the first night after dinner at Paris with one of my sales reps. He had to leave soon after dinner to meet up with another client so I was on my own. I spent an hour at the ... Continue»
Posted by germanboi4bbc 10 months ago  |  Categories: First Time, Shemales  |  Views: 2539  |  
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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 2 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 3657  |  
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First Date

My urges to be with a man had been growing every day, so I decided to start an online dating account, to see if any guys were interested in me. In a matter of hours, I received hundreds of messages from interested men. One in particular stood out to me. He was 6'5" and muscular and a former marine. He sent me flirty e-mails and I flirted back and sent him a few pictures. After about the 10th email he told me that he had re-read my profile and he didn't realize that I was transgender. He told me he had never been with a t-girl but that I was so sexy that he didn't even care, he needed to take m... Continue»
Posted by xjessica88x 22 days ago  |  Categories: First Time, Shemales  |  Views: 3835  |  
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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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