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Joseph got fucked in ways he never imagined Shemale Sex Stories

Joseph has been in search of a girlfriend for months now. Ever since his last breakup, nothing seems to work out for him. He is tall, handsome, and has a beautiful body. His green eyes occasionally captivated women. And yet, he could not land a date ever since Kelly left. This was probably because he tends to get tongue-tied around women ever since she left. But after almost three months without sex, he was getting desperate. He would occasionally check through different dating sites. This is...

A shemale couples vacation in Thailand Part 02

Welcome to part 2 of my story

My First Time with a Shemale

I had watched porn for a long time, graduating from straight porn to videos of shemales, falling in love with TS stars such as Leilani, Julie Bond, and the gorgeous hermaphrodite Dane Harlowe. However, as much as I fantasized about being with a shemale or cross-dresser, I never thought it would happen.Then one night when I was living in Indianapolis, after being out drinking and dancing, I stopped at the local adult video store. I had parked near a white van and, as I was drinking some more of...

Real event OMG shemale and another surprise

This is a true event, a lil back history, for about 3 yrs ive become fascinated by shemales, no porn will do without a shemale cock, i dont see myself as gay but i do wonder that if i like penis there must be some gay in me, but i do not like men at all. Now regular porn just does not do it for me and i alway fantasize about a shemale cock, a big juicy shemale cock and what i would do if i had the chance, i envy every man i see in the videos that get to suck and get fucked by shemales.cut the...

Fucking A Hot Shemale In Bush

Hi guys this is Avinash from Chennai.. I am 21 yrs old and this happened few years ago to me in a local train in Chennai. This story is about how i fucked a shemale and got robbed by her. Now to tell about me i am a fit guy with muscles shaped up.. My cock size is 13cm ( yes u read correctly.. My cock is 5 inches.. I cant lie that its 10 inch huge monster and all.. Now coming to story i used to go to my school by local train in Chennai.. From Guindy to Chrompet.. We all know beggars will get in...

Overdose of shemale cock

I had been at college for almost three weeks when the events I am writing about took place. My name is Karl. I’ve always considered myself a pretty normal guy. I played football in high school, dated a cheerleader, and usually got decent grades in my classes. Alright, enough about me… let me tell you how my freshman year started. I was sitting in one of the hang out areas on campus one evening, trying to figure out which of my new teachers would be least upset were I to turn in a...

How I Ended Up a Submissive Shemale Slut Part 1

How I Ended Up a Submissive Shemale Slut...Part 1 I am sitting here in my studio apartment, and I am alone and depressed and looking for guidance from a very dominant woman who wants a very submissive shemale slut that is 30 years old, horny as hell, and shares the same likes and tastes that I do. Mainly forced blowjobs, and lots of different outfits, everything from leather, latex, lingerie, you name it. Let me go back 5 years ago to how it all started for me. We all have our own...

Had Amazing Sex with My Crush Who Turned Out to Be a Shemale

My name is Nick. I am Software Engineer residing in Las Vegas- the perfect place to be working by the day and partying by the night. I absolutely loved the night life of Las Vegas. Occasionally on weekends, I went out partying at a nearby nightclub and casino. That is where I met Cassandra. She was a regular visitor too just like me. I often noticed her and sometimes even stared. It did not go unnoticed by her and she made the first move to get introduced. Soon after, we were making plans...

Sex With Shemale By Mistake

Mera naam Sumit hai me chandiagarh me rehta hon meri umar 27 sal hai mere ghar ke pass eaka 35sal ki ek ladki rahti heunka naam Rani hai, wo dekhne me mast sirf uska awaj ladko jesi hai uska boobs kam se kam 36 hogi aur gand to bahut badi hai. Wo dekh ke mujhe ek alag tara ki smile deti thi mujhe kuch pata bhi nahi chalta tha. Ek din hamare ghare me sab bahar gaya hue the me beth ke tv dekh raha tha to hama door bell ring hua me jab darbaja khola to dekha rani khadi thi, use ek white color ki...

My First Shemale

A little about me first. I’m in my early 50’s, regular build, and I say average looking man. I have never had the women chase me like some hunks would, but did Ok in my younger days. My cock is average size, but at the lower end of the range. I’m happily married to a wonderful wife for near 25 years. Like some guys I think I spend time on the net looking at porn. It all starts of fine, your fantasize about the girl next door, the trophy wife across the street, and so on. Well for me it went to...

One man rsquo s trip to the shemale dungeon

My phone rang just as I had finished cumming into Jess for the fourth time. It was Maria, who told me I should head down to their friend’s house as soon as possible if I wanted more cock. I had been enjoying Jess’s pussy so much that I hadn’t even realised it had got light, and I asked her if she wanted to join me. Jess said that she needed to get showered and go to work – something about the thought of her heading to the office with my cum still sloshing around inside her wrinkly hairy pussy...

Craigslist shemale

One day sitting at home edging, I decided to go on craigslist t4m most of the ladys were black with huge scary cocks then I happen upon a thai girl Tia, we started talking and asked her if she wanted to meet up, she didn't drive so I had to pick her up. as she walked to the car I took notice she was about 5'8 she had tight jeans on and a decent ass for a Asian girl. she had a leather jaket on and I could see she was pretty flat chested. Tia had shoulder length hair and her face all dolled up....

Shemale Surprise

This is 100% true, I know it may sound difficult to believe and I know if I read what is detailed below I’d struggle to believe it but this is what happened to me on Wednesday.I needed to take Wednesday off from work as a holiday to get some work done to my home, as the day wore on I had planned to get a tribute made, but I felt too horny to tribute I’d been to Northwich Sauna before (Which I’ve posted about before) and seen that they run a TV/TS day on Wednesdays, all are welcome to dress how...

i cant baleave i just fucked a shemale part 2

so it ben 3 days since crystal took my wife home I have not seen here in that time so I went to crystals house and knocked on her door she open the door wearing nothing but red hot pantie hoes and neon green corset she said well well well wat brings you to my home and I said im looking for my wife she said right this way we went down the stairs into her basement it all dark and there she was bent over naked tied on her table and there was another super hot shemale named Brittney she white lady...

Wife Shares Shemale

"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an hour see you." She hung up. The phone call made me really nervous.I had reasons to get nervous if not get a nervous break down. Tara and her husband owns a few restaurants in different cities across the States. I have known...

shemale sex slave

BDSM JOURNEY.Let me first say i am no writer by any means.This story starts 5 years ago. I was looking to move up in the mountains off grid with a homestead. I was a single man and wanted a parnter who could share with the daily chores and have for sexual gratification. Finding some one to leave everything the city offered to move to a rural area was a quest in itself. I knew I wanted a completely submissive woman ant my feet.So I put a ad on craigslist and it went a lil something like this"...

wife fucked by shemale

Wife fucked by shemaleThis is the story of me Rittu married to a guy named Harvinder in 1996. We had 2 k**s from our marriage .Harvinder was very fond of girls and even before my marriage he use to fuck prostitutes right from young girls to middle aged women. He used to get his cock sucked and even used to fuck these prostitutes in their ass. After getting married to him he used to apply all the tricks on me. He made me watch blue films and he get his cock sucked as women in bluefilm. He even...

wife fucked by shemale

Wife fucked by shemaleThis is the story of me Rittu married to a guy named Harvinder in 1996. We had 2 k**s from our marriage .Harvinder was very fond of girls and even before my marriage he use to fuck prostitutes right from young girls to middle aged women. He used to get his cock sucked and even used to fuck these prostitutes in their ass. After getting married to him he used to apply all the tricks on me. He made me watch blue films and he get his cock sucked as women in bluefilm. He even...

Shemale fun

Recently I've been chatting with a very feminine and beautiful shemale named Lisa.We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to concoct and excuse as to why I had to go to (city name withheld) and my wife didn't see any reason not to bnelieve me. My wife knows that I love porn, but I've never expressed to her that cock also turns...

My shemale mother

I know there is a similar story similar to these but be assured, the other story only served its purpose as a catalyst for this one. This is a pure fantasy, the top fantasy that has been lingering in my mind for several years..here it is....I am 35 years old and had always been living with my mother, who is almost 50 since my father left us 20 years ago. I am not sure of the reasons but I do know that my mother is an average looking woman with nice looks and a not so fantastic body. Her pear...

Buffy the Shemale Vampire Slayer Part XII

Buffy the Shemale Vampire Slayer, Part XII By Cal Y. Pygia "Let's get this over with," Buffy suggested. "The sooner we start, the sooner I kick your demon ass." Baphomet smiled. "You will fuck the witch," he said, "while I fuck you." Buffy shook her head. "Willow's my best friend. I can't--" "Then you have lost before we've begun." "Buffy, it's okay," Willow said. The Slayer looked at her. "Will, we've been friends since high school." The redheaded witch smiled....

Ek Raat Ne Mujhe Bana Diya Shemale 8211 Part 1

Hi, i’m akansha from noida(up) but currently i’m in newyork,its my first story, professionally i’m a fashion designer,age-25, my color is fair, height is 5’6,híp size 34,breast 32,penis-4to5inch basically i’m a shemale. Now i’ve been start my story. Ye baat uss time ki hai jab mein 20saal ka tha or noida mein naya tha kyuki mera admission wha k ek college mein ho gya tha. Maine noida mein rent par ghr liya or sath he Maine ek calcenter mein job karni shuru kardi wha meri shift dophar k 4se raat...

Shemale on Shemale

We were in the back of a taxi, our tongues deep in each other’s mouths, tasting and sucking and swirling. My hand slowly moved up her perfectly toned thigh and under her skirt. I lightly caressed her half hard cock through her thong, barely touching her, just tenderly stroking with my fingertips. She responded by grinding herself against my palm in a seductive, circular motion. I could feel her getting harder and she moaned softly. I felt that moan vibrate on my tongue, causing my own cock to...

Gas Station Shemale

Before I begin this story let me say this: I know that a gas station is a place where one would not likely see a chick in a short skirt with heels and even if you did it wouldn't happen in the wee-hours of the morning.........would it??? On this night I hadn't paid close attention to how much gas I had in my car and when it was time to drive home from the party I'd been at I realized that I absolutely had to stop to get some (probably not a real good idea but I had no choice). Signage along...

Taken by Force a Shemale

Taken by force a shemale! By venisss It started very simply. I was on vacation in goa, and stayed the hotel, overlooking a nice sunny beach, with dozens of various palms around. Once I saw an attractive woman at the hotel bar and offered her a drink. She accepted and we conversed. I was not planning to pick this girl up and make it out with her, just normal decent chatting. She appeared to be a very good listener and glib, it was very interesting with her. Soon, we were laughing and joking like...

Nazoo aur Indian shemale and boyfriend

Heloo meri lesbo friends!mera naam nazoo khan hai.main 28 saal ki bahut gori chiti sehathmand sexy badan wali behad khubsorat larki hon.meri figure size 38 28 38 hai.mera aik boyfriend hai jis k 9inch lamby aur 2.5inch motay goray lund ki main dewani hon. Wo main usse khub chudwati hon,hum dono na bahut se khubsorat larkion aur jawan sexy aurton k sath sex ka maza liya hai.muhje yaqeen hai k ajj ki story ko read kar k mero lesbo dosto ki chuton se bahut pani nikle ga.ab ap meri real story ko...

Double dick The horny doctor and the shemale nurse Free Sex Stories and Adult Erotica Stories

Sheila was going to see Dr. Dray. He was a supposed gynaecologist who specialised in herbal medicine. â€œWhat was that?â€, Sheila had thought, but she went anyway. When she arrived at the clinic she was met by the nurse and told to lie down with her legs open and panties down. As she lay, she saw that the nurse was watching her and her eyes were glued to her cunt. She was going to meet the horny doctor there. Then the doctor arrived and said that he was going to check her. She nodded and watched...

I want to suck your lollipop the Shemale told me Free Sex Stories and Adult Erotica Stories

Shana was sitting on the bed with a sultry look in her eyes. I was going to fuck her, fuck a shemale. â€œ I am going to suck your cock and fuck your ass,â€ I tell her. â€œYeah, I will do the same to you. Now come here. I want to suck your lollipop,â€ she says and licks her lips. The tone itself makes me go wild. I go closer and let my naked and hard dick hang in from of her. She takes it in her hands and rubs it between her palms. I groan and thrust into her palms. She sucks the head of my cock and...

Sexy shemale a fantasy cum true

I had known Teanna casually for about 2 years. I always thought she was cute. Around 5’ 4” with dishwater brown hair and athletic toned body. You should know, I get very horny very fast sometimes. Anyway,last week Teanna was walking home and I saw her. "You need a ride?" I asked her. "Yes please!" She replied. She opened the door and hoped in the Beamer. "Where do you live?" "Off fremont ." That was kinda were I lived. I started to drive off chatting with Teanna... We got to her house about 25...

A shemale couples vacation in Thailand Part 1

I'm neither a professional writer nor a native english speaker. So let me apologize beforehand for my bad grammer and writing skills. This story includes mainly: Shemale on shemale , Interracial , Domination , Submission , White , Asian , Ladyboy , Some light cuckolding.I'm a Trans-girl also known as a Ladyboy, living around the area of Pattaya at that time. I was just 22 years old then but dispite my age, i had already multiple sexual encounters with other ladyboys. And yes i said ladyboys...

first time with a shemale

Anyone who has read my other stories will know that they are based on real events, this one is also based on an actual event. It happened on a recent trip to Thailand.We arrived in Thailand on a Friday morning, looking forward to a well-earned break. Jaq and I worked long hours, and we lived for our holidays. We had decided to visit Thailand as we were both curious about the availability of good looking shemales.It had long been a fantasy of ours to try a threesome with a shemale and hoped this...

My first time with a shemale

OK, I was wasting my time on shamble videos and pictures on the web for about 8 years! When I first entered a porn site I almost got sick, but soon I got really curious about it but didn't dare to click that button; couldn't explain why I wanted it so much though. Eventually I pressed it. I started with shambles alone, then shambles fucking girls, then shambles fucking shemales and end up with shemales fucking guys... I started loving it, watching it on a daily basis. My fetish for thong...

My first encounter with a shemale

I am a straight guy who had never strayed before.. however i had been having urges over shemales and started wanking to shemale porn every now an again online. i have always been interested with my ass being explored but i never found men attractive. with shemales it was different. they are beautiful, slender but also filthy at the same time. it seemed perfecti had planned a europe tour some years ago and my first stop was amsterdam. after a few hours of roaming the red light district i was...

The Studio and the Shemale Pt 3

4 years have now passed since I went to work for George as his apprentice. George has semi retired and left me to run the Studio with Amanda as my receptionist. Amanda and I are still as in love as ever. We leave our flat and walkk to the Studio at about 12 and stay open till quite late in the evening. Most of our work is with shemales now but we do have a few crossdressers on our books and we will do photographs for crossdressers if they want it. Amanda or Jessica will do their make up.We have...

My first Shemale a true love story

Even from a pretty young age, I loved Shemales. I loved everything about them. They seemed to me to be the perfect object of sexual desire. Beautiful, feminine, tits and a cock. My first introduction happen by accident, in a way. On the other side of town was a row of newspaper stands that sold adult newspapers. Late one night, I rode my bike to them and with a pocket full of quarters, bought every one. When I got home, i couldnt wait to look at them and in the darkness of my bedroom, saw my...

MY FIRST SHEMALE ENCOUNTER

I remember the first time I found myself in bed with a shemale. I had just broken up with my girlfriend. I was lonely, I was horny, andI had zero intention of finding myself in another relationship with a woman. When I told my buddy, Bob, he told me he knew just where to take me to solve this. So he took me to this club over in West Hollywood. The place was FULL of gorgeous women. My head was swimming - they were almost all slender and dressed in very sexy attire. Short skirts and sheer nylons...

me my daughter and a shemale

my last story was with my daughter for the first time now we both have shemale girlfreind very beautiful ones they would come over me and my daughter would put on our sexy heels she picks my shoes now lol and they would fuck us both on the same bed theses shemales are in good shape they would fuck me and my daughters tight lil asses and shoot globs of cum then they would watch us creampie it out one of them came over one night when i got off work my daughter wanted me to tougue out her shemales...

My First Shemale Encounter

I remember the first time I found myself in bed with a shemale. I had just broken up with my girlfriend. I was lonely, I was horny, and I had zero intention of finding myself in another relationship with a woman. When I told my buddy, Bob, he told me he knew just where to take me to solve this. So he took me to this club over in West Hollywood. The place was FULL of gorgeous women. My head was swimming - they were almost all slender and dressed in very sexy attire. Short skirts and sheer nylons...

How I Ended Up a Submissive Shemale Slut Part 1

I am sitting here in my studio apartment, and I am alone and depressed and looking for guidance from a very dominant woman who wants a very submissive shemale slut that is 30 years old, horny as hell, and shares the same likes and tastes that I do. Mainly f***ed blowjobs, and lots of different outfits, everything from leather, latex, lingerie, you name it. Let me go back 5 years ago to how it all started for me. We all have our own stories and beginnings, and this one is mine. I am a very...

Shemale Subway Sex

I was out at a dance club with some friends on Saturday night. Clubbing isn’t really my scene though, and I soon found myself very bored. Looking at my watch, I saw that it was almost 1 o’clock in the morning. I was having an awful time, and if I didn’t leave then, I would miss the last subway train and have to take a $50 cab ride home. So I said goodbye to my friends, and caught the very last train home. The subway ride from the club was going to be around 40 minutes. At first, the car was...

One of my shemale escapades from back in the day

A number of years later, after my first shemale expereince, I still had a penchant for a hot shemale or a slender sissyboy who was passable. That's when I met Gina, who fit the mold of a slender sissyboy who was much more than passable, she was gorgeous.The first time we got together was on a rainy Sunday afternoon. My wife was out of town and I was cruising aroind on AOL in the SoCal Shemales chatroom. I came across her screenname and we started to chat. We traded writen descriptions of one...

The Studio and the Shemale

When the company I worked decided to relocate to the north of England, it was made clear to me that there would not be a job for me there and so the decision whether to move woth or leave was decided for me. The redundancypayment was extremely generous, as it should be, I had been with them since I left school. So now I had to find a new job and the decision was whether to stay in the line I was in or change careers, but With the redundancy payment as it was there was no rush.Quite by chance I...

Erotic Massage From A Shemale Masseur

Hello, this is Rahul. This happened when I was on a business trip to Dubai. I am a bisexual guy and like she males, crossdressers. Anyways I found an ad by a shemale offering massage. I booked an appointment and went to her place. Her name was Maria. She was an English speaking shemale from Brazil. I was happy that she was from Brazil since my earlier encounters with Brazilian shemales was very good and satisfying. Maria greeted me with a smile and asked me to undress and lay face down on the...

my shemale GF part 7 Bukkake

My birthday was like a week ago or s o, and Christy got me what ive been wanting, a bukkake. I finally got this present like two days ago. We went to dinner, we meaning me Christy, Brittany apparently another shemale who I didn't know about but also my friend, and Jennifer, who I did know was a shemale. There are apparently plenty of shemales where I live, awesome. We went to Buffalo Wild Wings, Christy wore a short jean skirt, and nothing underneath, I know cause I dropped my fork and she...

Shemale Subway Sex

I was out at a dance club with some friends on Saturday night. Clubbing isn't really my scene though, and I soon found myself very bored. Looking at my watch, I saw that it was almost 1 o'clock in the morning. I was having an awful time, and if I didn't leave then, I would miss the last subway train and have to take a $50 cab ride home. So I said goodbye to my friends, and caught the very last train home.The subway ride from the club was going to be around 40 minutes. At first, the car was...

How I Ended Up a Submissive Shemale Slut Part 1

I am sitting here in my studio apartment, and I am alone and depressed and looking for guidance from a very dominant woman who wants a very submissive shemale slut that is 30 years old, horny as hell, and shares the same likes and tastes that I do. Mainly forced blowjobs, and lots of different outfits, everything from leather, latex, lingerie, you name it. Let me go back 5 years ago to how it all started for me. We all have our own stories and beginnings, and this one is mine. I am a very...

shemale on shemale

Hi dear it just a story may be its real cany sure some 1 told me & i write this 1 for u Hi mai ap ki friend ap ka leya aik or story la kar aee hoain, mujha 1st three stories ka jo respons mila vo to mai ko bata nahi saktee, par ap ka tnx zaroor kartee haoin dil sa. Isee ka sath maree 4th story ap ka leya. Ya mara sath hona wala aik ajeeb or anokha waqia tha. I mean really very different, mujha movie dakhna ka mood huva to mai cenma chalee gae wahan khelade 420 film aksha ki lagi thee new film...

Jimmy Olsen Shemale Bimbo Chapters 12 to 13

Jimmy Olsen - Shemale Bimbo by Mistress Tawny Suede Chapter 12 - Frustration! Thursday morning. Jimmy woke up and stretched. He rolled over and sat on the edge of the bed. He momentarily lost his balance a bit. Despite weeks of having tits, they still threw off his centre of balance a bit. And his back hurt. But he smiled when he realized that was because his boobs had gotten much larger since his initial transmogrification. He giggled as he took his breasts in his hands and...

Passionate Sex with a Beautiful Shemale

Passionate Sex with a Beautiful Shemalea man and his shemale lover get down to businessWill led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sarah lightly ground her ass into his crotch, rubbing herself against his hardening cock.“Mmm,” she moaned, feeling Will’s lips kiss the nape of her neck, causing...

1st time with a shemale

I have always enjoyed playing with my ass hole, about two years ago I was in Chicago and went online to Eros and chose a shemale named with held. I called her up and she came to my hotel room. I was very nervous when I opened the door. She was about 6' tall and was a very good looking Latino. She bent down and gave me a kiss right on the lips and man where her lips where soft. She went into the bathroom and asked me to relax and she will be right out. I was lying on the bed and she came...

My First Time With A Shemale

Hello Indian Sex Stories readers, thank you for your continuous support. Your support helped me to experiment more and more with different kinds of people. This time it was an unexpected encounter with a shemale. I hope you like this one. Email me at & tell how hard I made you cum ;). And also if anyone from Mumbai or Thane want to have a session with me than you can email me without hesitating. I don’t judge people don’t worry. So let’s come to the story. This is a recent story that happened...

Crossdressing Adventures With Shemale Teacher

I am Abhishek. Since childhood, I have been little feminine in nature, for which I have even been bullied sometimes. I have been blessed with really soft, smooth and fair body, with not a single trace of hair on my body and face. I have a slim and athletic body, and if you saw me from back, you might mistake me for a teenage girl. This incident that I am about to narrate, happened when I was studying in class 12, with my teacher whom I always thought was female until that rainy day in...

First Time with a Shemale

This is a true story about my first time being with a shemale. I happened just over a year ago on the tail end of a business trip to Amsterdam. I had a couple of free days at the end of my trip to enjoy and explore the city. So naturally, I decided to check out the night life and that meant a visit to the Red Light District.I spent a lot of time just walking around and taking in the sights and sounds of the area. There were so many people walking around and it was alive with all their energy. I...

Threesome In Thailand With Hooker And Shemale

Hi friends. It’s your favorite writer Abhay from Jaipur. Thank you all for the huge response for my last sex stories. Now I am back with my recent real encounter. You all know my vitals and so I am skipping that part. Suggestions and comments are always welcome. I respond to every email I get. So, let’s start with my real life incident. It all happened in May 2018 during my vacation trip to Thailand with my wife and another couple of friends. Our vacations were nearing the end and I wanted...

Massage Sex With Latina Shemale

Hello, I happened to be on a trip to Brazil, when after my meetings, I went back to the hotel and took a nap. After an hour or so I was fresh and charged up, I decided to go for a massage. I looked at the online sites and fixed up a house call to my room, by the way I had chosen a transsexual for my massage. After an hour, Maria knocked on my door; I opened it and led her inside. Maria was around my height, with dark jet black hair, chocolate color skin, Though her breasts were not huge they...

Crazy Hotel Sex With A Shemale And Her Husband

Hello readers, this story is about Munira, an introverted, chubby girl from Chennai. She enjoyed with a shemale couple. First, a bit about Munira – aside from being introverted, she reads many fantasy novels and secretly smokes in her best friend Arpana’s room. She lives alone in a two-bedroom flat and works as a data analyst in Bombay. She is 5’2”, wears black-framed glasses, has curly hair. She looks a bit like Nithya Menon, except her skin tone is a bit duskier. Now that you have a picture...

Wife with a Cock The Sexual Adventure of a Shemale Free Sex Stories and Adult Erotica Stories

Laura was married, happily married to Matt for a long time. But today she was nervous, she had no idea how to tell this to Matt. Her phone pinged. The message was from her husband asking if she is excited about tonight. She was, but she was nervous and little scared as well. She finished cooking the dinner and went to take a long hot shower to calm her mind. She slid into the bathtub and started soaping herself. For some reason, she was feeling particularly hot tonight. Matt has been away for...

My first time with a shemale True Story

This is a true story about my first experience with a shemale. I was sitting around the house the other day horny as fuck. My usual girl that i call on when i get that way had family in town for christmas so she couldn't meet me. So i decided that i would look on craigslist and see if i couldn't find someone that wanted to fuck as much as i did. As i was looking through the ads and as usual not finding any women that were real on there i clicked on the T4M section. I had always been a bit...

Sex date with a sexy shemale

For already several weeks I surf through a website that advertises women, men and also shemales. Since my great experience with the other shemale during my holiday (see one of my other posts) the craving grew bigger and bigger to meet up with one again.So last night I decided it was that far. I drove to the address I got from her on WhatsApp and rang at the door. After paying her the agreed amount (love the humiliation factor of this, need to pay someone to fuck my ass) she showed me the...

First time with a Shemale

First off this is a true story. I lost my virginity at a young age so sex is always been something usual for me. As far as how I lost my virginity... thats another story. I have always dated women that were openminded, bi-sexual and down right sluts. I have been in strange conversations and situations because of being soooooo "openminded", heres my story... Bella and I were getting dressed for a night on the town. We had plans to meet a couple from a a website we were members of. So we were...

Shemale Fantasy

Recently you've started to wonder what it would be like to be with a shemale. You've always been attracted to women and have no homosexual interest at all, however the fascination of a women with a penis has made you curious of what a sexual encounter with a shemale would be like. Curiosity finally getting the better of you, you decide that you're going make it happen just once.

Shemale at the airport

The first shemale story I ever read and still one of my favourites...Layovers are a pain at the best of times but the prospect of five hours at theairport was not a good one. My inbound flight had been delayed and I had missedmy connection, so there was nothing for it but to wait out the afternoon andcatch the next 'plane home to the wife and k**s.The only saving grace was my business class ticket, meaning that at least Icould loaf around in the executive lounge and not in the main...

Shemale at the airport

This is the first shemale story I ever read and is still one of my favourites...Layovers are a pain at the best of times but the prospect of five hours at theairport was not a good one. My inbound flight had been delayed and I had missedmy connection, so there was nothing for it but to wait out the afternoon andcatch the next 'plane home to the wife and k**s.The only saving grace was my business class ticket, meaning that at least Icould loaf around in the executive lounge and not in the main...

My second shemale A true love story

Having just left Amanda’s, my very first shemale, I found myself still lusting for more. I had just cum twice, (the joys of being young) but wanted, needed more. I quickly flipped through pages of my adult personal newspaper and found “Jennifer.” She looked beautiful in her ads picture. There is nothing more attractive, nothing sexier than a shemale and my lust for them seemed to have only increased. Jennifer lived in a busy apartment complex and I nervously searched for her door. “Paul” I...

A teenie niece s first shemale experience

I heard my phone buzz one afternoon, just as my hard cock was sliding effortlessly into Lela’s smooth arse tunnel. “I’d better just check that” I said to my panting shemale lover, given that I was supposed to be working from home.It was a text from Jess. It simply read, “I’m bored and fingering my hairy cunt. How about you come over and fill it with something bigger?” Jess knew I was at home, and she knew I wouldn’t be doing any work! However, she was about to be surprised with a threesome. “We...

My First shemale Mag and a little More

It was late afternoon when I ventured into the local public toilets , I had been a few times and had been reading the graffiti for ages , so was already excited to be going back.I went in and checked out the first couple of cubicles and read a few new additions and was already hard and turned on , there is just something so primitive and seedy about wanking in the toilets reading dirty messages , wonderful.I moved into the third cubicle and discovered a carrier bag stuffed behind the toilet ,...

2nd Shemale experience

All my stories are based on my own experiencesAfter my first experience with a shemale (also pasted on here, She was a He) I wanted to have a second, but this time for me to knowingly know what I was about to do.I trolled chat rooms and dating sites for a few months, getting to know a few girls and then approached the subject. I soon was going to go on my first date with a shemale. We meet at a local station and she was as stunning as her pictures and so convincing, she was even turning heads...

Wife Fucked By Shemale

This is the story of me Rittu married to a guy named Harvinder in 1996. We had 2 k**s from our marriage .Harvinder was very fond of girls and even before my marriage he use to fuck prostitutes right from young girls to middle aged women. He used to get his cock sucked and even used to fuck these prostitutes in their ass. After getting married to him he used to apply all the tricks on me. He made me watch blue films and he get his cock sucked as women in bluefilm. He even used to make me drink...

My Shemale Mom and Aunt

I'm 5 feet and six inches tall I weigh 135 pounds soaking wet with long brown hair. Mom and Auntie Karen are both 6'2" with huge breasts and long legs. I walked into the Den to see them watching some shemale porn together. I sat down across the room from there with trembling knees and tears running down my cheek on the right side. Mom said come and sit down next to us, so I crossed the room and sat between them they both kissed me on the cheek and said We have a confession honey.Timmy I'm not...

wife fucked by shemale

This is the story of me Rittu married to a guy named Harvinder in 1996. We had 2 k**s from our marriage .Harvinder was very fond of girls and even before my marriage he use to fuck prostitutes right from young girls to middle aged women. He used to get his cock sucked and even used to fuck these prostitutes in their ass. After getting married to him he used to apply all the tricks on me. He made me watch blue films and he get his cock sucked as women in bluefilm. He even used to make me drink...

Being a shemale s toy can be fun

Joliet called and asked if I would be interested in having some fun...I thought about the last time and how pissed off she got. I hesitated long enough for Joliet to whimper in the phone 'I promise to make up for my last theatrics, no bondage and I will reward you very handsomely if you attend to my needs this week end.' Sensing desperation, I gave my demands 'reward me up front in large bills in an envelop that I will address and drop into the post office before we do any thing, you will give...

Meri Shemale Teacher

Disclaimer : All characters in the stories are fictional. The story is about a sexual relation between a shemale teacher and her student. If your name is used as one the character it is a coincidence. If you are against anything above stated please stop reading. I hope you enjoy! The ideas for this story are taken from many others as I’m regular reader to many erotica websites and blogs. For any comments and ideas Email me – Mera naam Tanish hai, yeh tab ki baat hai jab mein apne medical...

Shemale Supermodel

SHEMALE SUPERMODEL ? by: Charlotte Bollinger CHAPTER 1 We were already late as the plane taxied to a stand still at Charles de Gaulle because of the atrocious winter snows, as the seat belt signs were switched of there was the usual click, click of seat belt buckles being undone but non of the usual pandemonium and mad rush to be first of the plane that I had experienced before when I had traveled in economy class. Now being one of the privileged few who can travel first...

Buffy the Shemale Vampire Slayer Part II

Buffy The Shemale Vampire Slayer, Part II By Cal Y. Pygia Buffy waited until twilight, hiding out in her bedroom, as she tried to come to terms with the bizarre fate that had befallen her, thanks to the Feral demon's bite. It wasn't easy, psychologically, physically, or otherwise, to have gone to sleep a girl and to have awakened a hermaphrodite. She wasn't sure how to feel about the weird transformation that had changed her into a shemale. It was strangely titillating. At the same...

Buffy the Shemale Vampire Slayer Part IX

Buffy the Shemale Vampire Slayer IX By Cal Y. Pygia Buffy had emerged, at last, from the cavernous planet-pussy awash in semen, only to find herself in a landscape filled with phallic plants. The strange stalks could elongate instantly, swelling and stiffening to whatever dimensions were needed to reach and penetrate their prey--and, Buffy realized, "prey" described her status perfectly. As the Slayer, she was not used to being a victim, and her newfound role did not suit her, not...

Gang banged in bondage by shemale co workers

I had just got home when my cellphone started to ring. When I anwered I heard my boss on the other end of the line. And she told me to come to her house for some "Fun" in a very ¨seducing voice.After I took the buss there and walked up her driveway I kept wondering if my great looking boss and her sexy secretary was gonna tie me up again. The first time had been a real suprise but I had still enjoyed it in the end.When I knocked at the door her secretary opened it and beckoned me in.When I came...

t gurl shemale at straight singles dance quo

ok....so if u don't know, a t-gurl is what is commonly called a shemale.....but tgurl is preferred by us gurls. anyway, my true story revolves around a singles club in a city in ohio that gets together at the end of every month and they have about 300 people that show up, hang out, dance and socialize. well, three of us t-gurls decided we'd go and see what it was like. since we look pretty good nobody guessed who we were and so we just set about enjoying ourselves by having some drinks and...

Wife Fucked By Shemale

By : harryshanty63 This is the story of me Rittu married to a guy named Harvinder in 1996. We had 2 kids from our marriage .Harvinder was very fond of girls and even before my marriage he use to fuck prostitutes right from young girls to middle aged women. He used to get his cock sucked and even used to fuck these prostitutes in their ass. After getting married to him he used to apply all the tricks on me. He made me watch blue films and he get his cock sucked as women in bluefilm. He even used...

Idndian shemale in pakisan

I’m shemale actually name kuch be jo ap ko pasand ho or name main kaya rakha hai or wasa be hamara name o roz change hota hayin, magar mai bilkul larkee lagtee hoain. Quainka maina skin ki surgory karae hai, or maina apni chal dhal sab kuch girls ki tarha kar leya hai, maree 35 age hai kanpoor ki rehna wali hoain akalee rehtee hoain, girls ko cheat kar ka unha chodtee hoain. Mara boobs ka size 36 hai, waste 30 hai, looking average. Lets start. Maree 1st story to ap na parhee or bohat acha reply...

Shemale

"What is this?" My wife asked me as she opened my suitcase.'Fuck', I sighed to myself. I had just returned from a business trip where I purchased a butt plug. Truth be told, I felt like I was having my mid-life crisis. Instead of buying a Porsche or Lamborghini, I got curious about my sexuality. I wondered what it would be like to suck a cock, even though I did not find men sexually attractive at all. I felt more and more compelled to be on my knees, to have a cock in my mouth. This became my...

First shemale experience Sierra PT 1

I was about 24 when I met her, Sierra. A petite ebony colored skin shemale, about 5'6 and maybe 160 pounds. Sierra had breast implants and several other cosmetic surgeries done to include laser hair removal, she had her adams apple shaven down and she was on estrogen shots. Although, very slender Sierra had curves like a female gymnast. I was truly taken back by her. I would randomly see her in different places. i lived in Cocoa Beach at the time, in the mid 90's. I eventually...

Shemale Shilpi banged my pussy

I am Nargis. I am an in a kindergarten school in Hyderabad. I am 32, age, beautiful, fair, married with no kids, and blessed with a 36d-30-38 figure. Life at my school was a fixed daily routine, boring. The majority of teachers were mature. They were always busy in areas in which I had no interest. I started working here 3 years back. My friendship started with a new trainee teacher Shilpi, who recently joined here after her graduation. She was a bubbly girl, and soon, we became friends. We...

Shemales An Appreciation

Androgyne, futari, girly man, he-she, intersexed, hermaphrodite, kathoey, ladyboy, newhalf, shemale, tranny, transgender, transsexual--there are lots of names for chicks with dicks--maybe too many. As whenever such a case presents itself, it is helpful--no, mandatory--that one define one's terms. As used in this essay, "shemale" is reserved for pre-operative transsexuals who have decided that breasts have made them womanly enough and that they will forego sex-reassignment surgery, opting...

Sex with an Shemale Prostitute

An while ago I visited an Shemale Prostitute. It was in an neighbour City. I discovered her Ad Board online. The reason why I chosed her was her cock size. It was 9 inch. Horny as hell I went into my car and drove about 20 miles, until I reached the house which she rented for customers.As I saw her I was a bit dissapointed. She didn´t look like on her pics. She kinda looked very masculine. Anyways, I wanted to see her cock. So I gave her the money and took her panties off. I noticed her prick...

Shemale Mistress borrows my Submissive Wife For a

I received a call from a friend of our's a Michelle a shemale Mistress asking if my sub wife could be available for a weekend party. I asked my wife last night if she wanted to be lent out ? She said it would be fine. I called Michelle and said she would be ok. Michelle said she would text me instructions. A day later I received a text of instructions have wife completely shaved pussy, ass and head . Have her dressed as follows cuffs on ankles and wrists. Butt plug and garters and heels and 6"...

Shemale Funpark

You go to a Funpark in Miami, Florida where you are supposed to meet your Friends. You really like them and drove all the way out here just for them. Right as you enter the Funpark to get to the meeting point, your Friends call you in a groupchat. They tell you that their Car broke down a long time ago but their Phones had no Battery and they were in the middle of nowhere. They could only call you now to tell you that they sadly can’t come to the Funpark. They say that you have to go on the...

My First Shemale

Early May 2006 or 7, standing on the northeast corner of 46th and 3rd, a rather nice New York City day, except Belinda wasn’t answering her phone for our 3 pm “appointment”, and I was not keen to just hang around smoking cigarettes on the corner wondering if I had been stood up. I had no prior experience but it dawned on me shemales, especially shemales for hire, might not be the most dependable group of people, well, maybe if they were a shemale cop, that thought hit the erogenous spot of my...

Visiting shemale goddesses

Sexy hung shemales have long been a favourite of mine and over the years i have had several sexy encounters of all kinds. As ive got older it has become more appealing to have these beauties top me if possible. Most ive met have been quite abrupt and arrogant and have suited the top position well. Not every experience has been nice. However my last one was a really nice suprise.I was in Amsterdam working for a week and had a 3hr slot early afternoon to amuse myself so took a short walk around...

Shemales An Appreciation

Shemales: An Appreciation By Cal Y. Pygia Androgyne, futari, girly man, he-she, intersexed, hermaphrodite, kathoey, ladyboy, newhalf, shemale, tranny, transgender, transsexual--there are lots of names for chicks with dicks--maybe too many. As whenever such a case presents itself, it is helpful--no, mandatory--that one define one's terms. As used in this essay, "shemale" is reserved for pre-operative transsexuals who have decided that breasts have made them womanly enough and that...

Shemale Park Shame

Park Shemale Shame Hi All, Now I’m as straight as the next man, I’ve got a cute little blonde girl with a great arse who I love to ride, lick and tit feel, but, well, here’s a cautionary tale. This is a warning for you fellas who sometimes find yourselves looking at pictures of pretty shemales, in all their frillies, on the internet when you just wanna have that added pervy kick so as to cum. Right, the other day I was walking home from the pub after a couple of after work drinks with...

First Time Surprise Shemale

I'm an eternal masturbator. I've always like wanking and playing with myself. At a young age I worked out that I likes playing with my ass hole, sticking things in it, walking round all day with something in it. With the advent of the internet I was like a pig in shit. So much porn to be had and so many things to see and do. One day I discovered the true beauty of the shemale. Wow. Gorgeous women, with cocks. Prior to this it had been women with strapons that got my attention, but this?...

My first time with a shemale

This is a true story, probably the wildest thing that ever happened to me. It happened when I was about 19 years old and lived in Hamburg, Germany. At the time I was one of those willowy, thin guys, little body hair and a healthy appetite for sex but not much experience yet. At a young age I discovered how exciting it is when I fondled and fingered my ass while masturbating and I developed a real fascination with anal sex.At the time I used to visit a club ("disco" in those days) somewhere...

Me And Two Shemale Lovers

The ad in the local “underground” paper said “2 hot she-male lovers looking for inexperienced open-minded male for exciting new encounters….” It added a few brief descriptions etc. I thought to myself. “Why not, you’re open-minded and adventurous?” So I gave them a call, wondering about the details. I’m not totally new to the scene and have dabbled a little in being in the bottom or receiving side of anal and while I never have travelled the shemale route, it always intrigued me. I have seen...

She turned into a Shemale

The weekend had just got under way and from the start of that Saturday you could tell something was in the air. She was acting like a shark with blood in the water.The day started with her rolling over and grabbing my Ballz with an aggressive fist, stretching them out, shaking my cock.The signs were there for a day filled with wonder and experimental crazy sex. The day moved along slow after that, we went out shopping, she tried on dresses to tease, we ate and just spent the day wandering...

A shemale transformation part 7

So i woke up in my room thinking i just fucked my mom but it was a dream also the name that i gave in my dream was not her real name my mom name is Jennifer she got big hug tits i mean nice round big perfect. She got big booty thin body thick legs anyway. As i was wakeing tho my door had been kinda open. I know somebody been watching me sleep or as come in my room i never leave the door open. I walk over to the door mmm nobody there then i close it and start geting ready for school i took my...

Shemale Assassin

Sarah was lining up a shot with her bow, preparing to take down the deer she had been stalking for ten minutes when there was a loud cry from the North-East of her hunting blind. The cry startled the deer, causing it to flee from the noise that permeated the forest."There goes a few meals." Sarah sighed with frustration.Within seconds of shouldering her bow, Sarah noticed that the cry was actually a call for help and she made her way through the trees towards the screaming woman that was making...

Shemale massage

It has been one of those long and stressful weeks. I’m in desperate need of relaxation and relief so I head over to an Asian massage parlor for a typical happy ending massage.The girl who usually massages me isn’t available so another girl is suggested which I accept. I think to myself that she can’t be much different than my usual so I don’t care much. I just need a massage badly.She comes out of the back from another massage and introduces herself as Jessica. I smirk a bit knowing there is no...

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