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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...

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...

Suprised by a Shemale

I had met Tara during lunch at a business conference. It was a fairly boring conference but the lunch was longenough we got the chance to talk at length. We hit it off right away. She was gorgeous and I couldn't take my eyes off of her. Much to my surprise, she asked me for my number. I was kind of in shock because no woman had ever done that but gladly obliged.We met for dinner and a movie one night and wound up going back to her place at the end of the evening. We made out for a bit, but...

I am a Straight Guy meets Shemale

I had the perfect level of alcohol in me, the amount that took away the fear without making me too drunk to function properly. Otherwise, there is no way I would have gone up to her. She was undoubtedly the sexiest girl in the bar- probably the sexiest girl in the city. And she was alone. Only for a minute, no doubt, before some other loser tried it on. Not this time, I thought. You don't shoot, you don't score.She was tall, dark, slim but curvy. Black hair, a tight red dress, dark red...

MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous during a flight, so I needed a drink to calm my nerves. I sat at the bar and ordered my meal and drink. After a few drinks were gone, I noticed this stunningly beautiful lady enter the bar. She sat a few...

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...

My first threesome with wife and shemale

My sex life with wife was becoming monotonous and we were looking for ways to spice it up. We explored different options which involved fantasies of both of us which we had not been able to fulfill. I had a long time fantasy of having a threesome with wife and a shemale which I shared with wife and after some discussion we agreed to go ahead with it. I had always watched shemale porn with interest. Recently my interest had increased and I was watching more and more of those videos that had...

Wife Caught Me with a SheMale

It all started out one day I was sitting around in my apartment watching adult porno on the computer. My wife had just left for work. I was horny and my cock was hard so I started jacking off. I was lying on my back pumping my cock hard when I started to cum it had been a week or so since I had any pussy and the cum shot out of my prick like a loaded gun.Some of it hit me in the face and some of it landed on my lips I stuck my tongue out and licked it off my upper lip. It tasted a little salty...

I have to tell someone My first shemale

I could not believe how beautiful she was! It was as if I was struck by a lightning bolt or ran straight into a wall. Absolutely gorgeous, long red hair, beautiful, perfect tan skin and just a dream petite body. I will tell you now, I had no idea that she was a shemale, and this is how I found out, and it changed my life.I was working and assigned to build some sort of temporary, private offices, but that doesn’t matter. What matters is that’s were I first saw her, that’s were we first met. Her...

Cat The Shemale

Follow me on insta @raqm0900. IF you love my stories.I am a closet CD and seeking a owner.Introduction:I could not believe my luck.In my sophomore year of college I started dating one of the hottest girls on campus. We had met in my History of the Roman Empire class and hit off right from the start. It took me almost a whole semester for me to work up the courage to ask her out. When her reply was, "I've been waiting for you to say something." I almost creamed myself.Let me explain. I am pretty...

A young teen and a much older shemale

I was drawn to her. There was something different about her for sure, something special. Big for a woman, but very feminine and sensual. At first, I’m sure her flirtations were innocent, just for the fun of teasing a horny young boy. For me however, it was so much more. An infatuation and lust that burned and would not die down. Although I was so much younger than her, it did not stop me from pursuing her. Too be honest, looking back now, although I didn’t know she was a shemale, I probably...

Fucked by shemale

I've always thought myself as a straight guy. However, I always fantasised about serving a big cock. The problem was that I didn't fancy guys. That is when I came across shemale porn, OMG, what could be better?! A hot ass girl with a huge cock. Unfortunately, convincing shemales that aren't escorts are hard to come by, if not impossible. I started scouring escort sites and found a local shemale offering her services. She was Latino, 5"10, big tits, and best of all, and 8inch cock. I was really...

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...

Fucked by shemale

I've always thought myself as a straight guy. However, I always fantasised about serving a big cock. The problem was that I didn't fancy guys. That is when I came across shemale porn, OMG, what could be better?! A hot ass girl with a huge cock. Unfortunately, convincing shemales that aren't escorts are hard to come by, if not impossible. I started scouring escort sites and found a local shemale offering her services. She was Latino, 5"10, big tits, and best of all, and 8inch cock. I was really...

Her perverted mother and the shemales

The next day, Jess was busy at work and texted me to ask if I would mind doing her a favour. She wanted me to go around to her sister’s house to pick up some of Ellie’s textbooks. I agreed I would, partly because I was intrigued to meet Ellie’s mother, imagining a mature version of the beautiful student whose mouth had made me come the previous day, crossed with the elegant dirtiness of Jess.I had also heard from Jess the real reason why Ellie was staying with her during her exams. Officially,...

From Female to Shemale

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Boss Turned me Into a Shemale

I should've guessed something was up when my boss Victoria winked at me on our way into the office. She's about 5'9", 130lbs, she just got a boob job last winter, and as she walks by her ass bounces in the sexiest way I've ever seen. Work started normal enough. Our company was in the testing phase of software for a military application. I wasn't clear on its purpose at the time. One of the women in my team walked into my office and told me Victoria needed to see me. I walked into Victoria's...

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...

Hands free self facial with a shemale

I was out at a little casino in Reno talking to this black girl. Her body was smoking and she was showing it off proudly in this tiny outfit and knee high boots. She was about 5'8" she had about a C cup. She was thick in all the right places. Sexy thick thighs. She was almost considered fat or a BBW. We talked, flirted, and had drinks for about an hour. After a while I asked if she was hungry. We got up and when she was getting she put her hand on my shoulder, I took a chance and leaned in...

First love with a shemale

This happened around 10 years back. I never had a chance to share my experience. After getting some free time at my work recently, i thought of sharing my erotic stories.I will cut the chase and jump into action. I had been browsing horny shemale videos for a long time but never had the opportunity to spend time with. The place where i stay does not have good transgenders and 80% of them are just fake and try to loot money. I searched the craigslist and from one of the websites luckily found an...

My Stepsister Was A Shemale

My Stepsister Was A ShemaleI won't bore you with all the crap so Ill make try and get you up to speed quick. My parents divorced when I was a k** and I lived with my mom most of the time (I was an only c***d). I moved away when I went to college. By the time I started grad school I had my own place and things were going fairly good. About that time my dad married this lady who had a daughter that wasabout my age. I met her at the wedding and I thought she was a realdish. Her name was Sheila,...

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 time with a Shemale

By the time I turned 18, I had already done a lot of fucking - mostly with women in their 30's and 40's. As a k**, I was kind of a stud, mowing lawns in the neighborhood. I had a bod, and went shirtless, in shorts and sneakers, for effect. The women in the neighborhood did love me and tipped me well after mowing their lawns and eating their "bush."I did finally land a job as a pool boy at the Fountainbleau Hotel. The sexual encounters remained the same but in much better surroundings, and the...

My first time with a shemale

My First Time2009, I was stationed in Camp Pendleton, CA at the time, just back from having been in Iraq and Kuwait for the previous 9 months. I had been looking at transsexual porn for a couple years at this point, having stumbled upon it somehow almost by accident. Still don’t know exactly how it got on my computer in the first place; probably one of the many hard drive contents exchanges that happened while deployed. Either way, moving along, when I returned, I began thinking more and more...

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....

Mile high shemale

“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual.For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator).The community I live in has lots of shemale beauts; maybe that started my interest. One such ravishing creature has a gallery close to my office, and I fantasize every time I see her in the coffee shop. She also has an eye popping diamond on her ring finger.Once in a while I’d visit...

forced by Shemale

After the shower I dried off and went into the darkened front room. Two dull red lights were lit, casting a warm glow around the room. She was sat on the bed as I approached, my little cock shriveled up and sitting on top of my tight balls. She smiled, stood, and sauntered over with a mischievous look in her eye. She was the one that initiated the kissing. It was hard and forceful: biting and pulling on my bottom lip, sucking my tongue hard into her mouth, forcing her tongue down my throat. I...

Transformed Into A Shemale

crossdresser – leather – virgin – shemale – lingerie – thrusts deeply – clad cock – tight denimI was 18 when I first had sex with a man. This is the story....I am a very hot looking guy. I say that knowing that some may consider me vain, or arrogant, but over the years I have had so many women and men tell me how fine I am, that I know it is true. I am 35, blond and blue eyed, 6'1," 180lbs, with a tan athletic body and a 7" beautiful cock. I have been dressing up as a sexy girl ever since I was...

First time hooking up with a shemale

Well the first time I hooked up with a shemale was an escort visit (night out, massage and the rest :)), this was when I just started to gain interest in shemales (about 2 years ago), so I became curious and wanted to know what it was like to spend a night with one, after all they say its having the best of both worlds. I looked up a Brazilian shemale online and when I saw the pictures, I couldn't resist a visit. I mean her femininity was beyond this world, stunning from head to toe. I gave the...

I lost my virginity to a shemale

As living in an Asian country where sex is very personal thing and no body wants to share any thoughts regarding that.Me as a person wants to try it in a different way and which took me to another level of that,which I had never thought of.Being a young 18 year old boy I use to see porn just to control my thoughts and body,like every guy use to do.Then while searching on net I came to know a word called shemale.I had heard that word earlier also when I was 14-15 but didn't paid attention...

i cant baleave i just fucked a shemale

I was at work and the express had hired a new sectary for me I asked her I said hey crystal can u get me my papers please from my printer cause I was writing and needed to save time crystal walked over and bent over a little she was dark black I mean real black she had thick legs big booty nice thin abs big lard tits long blood red hair red lips bright green eyes panties hoes on red thong red dress shirt black dress suit and skirt crystal said it ok to stair I said im not im working she...

First time fucked by a shemale

I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon. I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.Her hair was dirty blond...

Double Anal With a shemale

....He answered the door and there she was beautiful as ever. He had just paid 500 dollars to have a transsexual escort come directly to his door and greet him. She had on a long pea coat and thigh high boots. When she took the pea coat off all she had on was a one piece swimsuit. Her tits were a 36 D and she was 5'9 with heels on. She went over to him and kissed him with lots of tongue. She then grabbed his dick through his sweats and said "Hard already we haven't even started. Where's your...

My adventure with a shemale

My friend’s son was getting married and he wanted us all to go on his stag do in Amsterdam. Having flown from London we were soon settled in our hotel and the beers kept coming, it didn’t take us long to get steadily pissed. Soon everyone was pissed out of their skulls except myself and were soon falling asleep, I decided to have a walk around the city.I went from one bar to the next and when I went in the fifth bar this girl came up to talk to me, she was 21 years old, long black hair, slim...

Russian Shemales

(Translated from the Russian)We lived in small village, no work, nothing to do but smoke all day. Friend Serge and I sitting by road one day, when black sedan, shiny from city stop near us. The man inside wearing a expensive suit, and ask if we want jobs as models.Serge and I think must be joke. But man introduce himself as talent scout. He speaks Russian but with accent I don't not know where from. He says he is from modeling agency and is looking for new talent to model. Introduces...

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?...

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...

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...

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...

Boy gets Fucked by Shemale

This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when I was sixteen, I decided to see what it felt like to be a girl. I had never tried anal before (I could never bring it up to my girlfriend) but I knew I had to try something. So I gathered all the...

My First Time with a Shemale

When I was living in Indianapolis and horny one night, I went to a local adult bookstore at just after 3 AM in the morning. Already hard and as I parked, I noticed what appeared to be a woman in a van next to me. She was definitely looking at me…I figured that she was one of the models who fingered themselves while men jacked off. Nevertheless, she started her van and so I started my car and began following her down the road.At one point, she pulled into the parking lot of an abandoned gas...

My First Time with a Shemale

When I was living in Indianapolis and horny one night, I went to a local adult bookstore at just after 3 AM in the morning. Already hard and as I parked, I noticed what appeared to be a woman in a van next to me. She was definitely looking at me…I figured that she was one of the models who fingered themselves while men jacked off. Nevertheless, she started her van and so I started my car and began following her down the road.At one point, she pulled into the parking lot of an abandoned gas...

My Wife s Affair With The Shemale

My wife Tracy were not married for that long when she had her first affair. I met Tracy in high school and we dated for years before we got married when we were twenty two. I hit the jackpot with Tracy because she is absolutely gorgous and just an all around sweetheart. She has long blonde hair with brown streaks, hazel eyes, long legs, large tits and a tight ass. Tracy has always loved taunting her body wearing cloths like short jean shorts to show off her legs and tank top shirts to show off...

My first time with a shemale

Let me tell you a little bit about myself I'm five feet 10 inches tall around 220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer.Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort Lauderdale, when one night I heard a commotion in the parking lot. There were several men beating up a beautiful woman, when I tried to break it up I ended up getting very banged up myself.Her name was misty, she thanked me for helping her and asked if I need a ride...

MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous during a flight, so I needed a drink to calm my nerves. I sat at the bar and ordered my meal and drink. After a few drinks were gone, I noticed this stunningly beautiful lady enter the bar. She sat a few...

My Wife The TOP ONLY Malay Shemale

Hi all, my name is yarra (not my real name perverts!!!) and I am a proudly married matured male, now 57 years old.My wife, 52 is a (or was a) biological female technically, been married to me for the past 24 years.Let me tell you my fantastic and totally out of this world story.Flashback to 24 years ago, that is the 1989, when i just reached my 30'ish age, you had read my earlier life story in this "Xhamster" site, where I started my strange relationship with my shemale mother, the one who had...

My First Fuck With A Shemale

Hey, everyone, it feels so good to be back again here and share with you all yet another fascinating and horny story. This is your friend cum pal Dr. Raj from Gujarat. Just to remind you about . Do check them out. Coming back to the current story this was my first ever experience with a trans woman or shemale. And my God. it was one hell of a ride. To cut it short I met this shemale lets call her D through Locanto website. Of course, it was a chargeable meet. As far as my knowledge goes you...

My First Experience With A Shemale

It was a Saturday night and I had just arrived in Coimbatore by bus. I got down and didn’t get any taxi or auto. So I decided to walk to my home which was 3 kilometers from the bus stand. It was pretty dark and I was walking through this deserted street. All I could see was parked vehicles and some stray dogs playing. I saw a bright light from behind and quickly noticed that it was a scooty approaching. I signaled for a lift and the scooty stopped. It was a lady in dark blue saree and black...

My one and only experience with a tranny shemale

One Friday night I decided to take a ride to Hollywood to check out adult theaters as i had always gotten my cock sucked at different adult movie theaters. As I parked my car on a side street i walked to this one particular movie theater I found myself at entrance and paid the 5 bucks to enter. as you all know, when you go into any movie house, its always dark and you wait for a few minutes for your eyes to adjust to the surroundings. i was standing near the entrance and looked around to...

Memorable Night With A Shemale

Hello everyone, my name is Ajay Kumar and I am staying in Gachibowli, Hyderabad. A little introduction about me. I became bi-curious under different circumstances. I was later diagnosed with erectile dysfunction which made me more drawn towards the bisexual world. I have met with guys. But always felt that something was missing which made me more curious about meeting a shemale or couples. But found out that they were next to impossible. I signed up on various websites to search for shemales or...

Losing my Virgin Ass to a shemale

I’m not a person with a lot of friends; the few friends I do have don’t share much of my interests or places to go out to. Also didn’t date much. Which never bothered me, I was always happy going to a random bar on my own, and sometimes getting to know people and just have a few drinks and laughs for one night, a social butterfly if you will. But I can’t deny I felt my penis becoming fully erect in an instant when a cute girl with a fine ass walked by. I don’t have a preference towards a type...

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...

Sex With A Hot Shemale

Hello everyone, my name is Ajay Kumar and I am based out in Visakhapatnam. The following story is a work of fiction as the real-life situation slipped out of my hands miserably. The story is a bit long so bear with me till the end. A little introduction about me, I became bi-curious under different circumstances and was later diagnosed with erectile dysfunction which made me more drawn towards the bisexual world. I have met with guys but always felt that something was missing which made me more...

Sex Massage With Beautiful Shemale

Hi, I am Rahul; I was on a business trip to Singapore, when I decided to go for a massage, searching in Locanto I found a beautiful, good-looking woman offering the Ultimate Massage. I was somewhat surprised and intrigued by the ad and fixed up an appointment. I reached her place and the door was opened, “Hi, I am Sonia, come in “she said. “Hi, I am Rahul” I responded. Sonia led me to a chair where I sat before she brought me a cold beer. When I took it from her, our fingers brushed and I felt...

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...

My Sister 8217 s A Shemale

We are a family of four. Me, my parents and my sister. I am 23 years and my sister is 18 years old. She is very beautiful, fair and very sweet looking with small perky boobs and a very petite slender body. I, on the other, am a regular gym goer and have a very good physique, but the thing with me was that I was gay and loved gay and shemale sex. I have done gay sex a couple of times but have never been with a shemale. I always knew there was something different about my sister as I often...

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...

first time i had a shemale

It was no secret to me that my victoria was bi; we had talked about it and I encouraged her to express and explore her bi side. When I managed to get us a date with a hot girl that was goth and always wears neon red fishent pantie hoes neon red and black corset with black skirt with neon green dragons she realy truns me on when i walk by her but, I decided to keep that a secret. I took my victoria to a nice dinner, and while being seated our date for the night showed up and introduced herself....

Her first shemale

It was no secret to me that my girl was bi; we had talked about it and I encouraged her to express and explore her bi side. When I managed to get us a date with a hot girl, I decided to keep it a secret. I took my girl to a nice dinner, and while being seated our date for the night showed up and introduced herself- her name was Ann. We had a nice dinner, and on our way back I asked the girls to sit on the back seat. Ann was not shy, and neither was my girl, so before I knew it Ann had her hand...

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...

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...

my first time with three shemales

this is a true story it happened to me back in 1988 when i was still bi i was in a local gay bar it was shemale night close to midnight when i saw this very tall gurl walk in with some friends she was hot about 6' 2" tall with 6" heels" all legs and ass she was blond and so senual with red lips and blue eyes all her friend we shemales too. After the got a table and ordered some drinks the music started so i went over and invited her to dance and to my surprise she said yes so we dancwd this...

Magical Ring Turned Me Sexy Shemale

Hi, guys, this is Rii and you can find me on Facebook by searching Rii Femboi. Now coming to the sex story. I am 28 boy and an absolute nerd, always studying and as a result had no friends since my school days. I thought things would change in the college, but I was wrong that time too. After completing my college I got a very good and a high paying job, but there too nobody wanted to befriend me. I had to move away from my parents to Delhi for a critical project that my company entrusted me...

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...

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...

When A Straight Falls For Trans Shemale

Hiya guys.This is Aaxer with a new plot and a new story.This story will be different and actually is from the last story.I entered a real different experience this time.It feels shy and embarrassed to express it but I won’t keep you from experiencing it once you have read this story.Let’s jump to the story. Alright, here I’m in a bus moving out to my room as I’m a student in a good reputed college in Pune.I used to catch the bus from PMC depot.I always spotted a girl every time on the ride...

An Erotic Threesome In Delhi Me Rich Woman And Shemale

Hi reader, Now I am back with sex story of me (Sam) and the rich woman (Geet) name changed due to privacy. I am Sam a 27 year from Delhi. I had many casual sex encounters with married women and girls. Any women or girl can contact me at hangout Geet is a rich Delhi-based woman who has lots of money to waste on anything but that’s not much for a living. She sometimes feels alone even having around her as her hubby who is businessman always out for business. By looks, she is a gorgeous lady...

My New Girlfriend Turns Out to Be a Shemale

Where do I start?How about at the beginning. My name is Cal I am divorced and living alone. I am not a bad catch I am five foot eleven, short black hair, green eyes and no visible scars. I am a regular at the gym so I am in shape but not ripped. A seven inch uncut cock that I can use well. I dress nicely and have a good job. My friends Don and Lisa were feeling sorry for me they knew how ugly my divorce was and how lonely I was so they invited me to their pool party last weekend. They...

First time with a shemale

I must have been 16 back in the day, but I always looked older so it didn't really affect anyone's judgement in the sex world that I had loved since I can remember jerking off for the first time.I was walking the streets of Amsterdam that day, the Red light Disctrict looked like paradise on earth, all those hot hot girls smiling and telling you to come in...I don't even know how much they wanted, I didn't care, just walking in those tiny streets and seeing those creatures was more than...

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

I was on a vacation when I had my first shemale. It was a regular december day in Sweden, rainy and cold. I was in a rented motel room with my friend Katrin. She was from ecuador so she had a natural tan and a great body with curved hips and breasts that were large but not enourmous. She had been bored lately and called over her friend Fiona to have some fun. I was sitting in the bathroom when Fiona knocked at the door. Katrin opened it and I heard hushed tones from the bedroom. I exited the...

Selene and the Shemale

I had been friends with Selene for six years - we had met in our first year at university - at a film society party. I was a science major specialsing in partying. She was a music student. She had a sultry, sexy singing voice that was perfect for jazz and blues and even back then, she was earning a little money singing at parties. That was why we were both at the party that night, and why we ended up being friends with benefits during our college career, though never more than that. We stayed...

You ve Got Shemale

This is my first story of this type, so please, be gentle ;) It's a semi-true story, but definitely more fiction than fact, and it will be at least two parts.I moved to a smaller town when I was in college and found that I didn't fit in at all. I actually got so lonely that I took up a friends advice and joined a dating site.I had gone through a large number of messaging women on that site to find most remotely near me wanted nothing to do with me. My age range of early twenties had little...

Transsexual Shemale

TRANSSEXUAL You are not a woman; You are not a man; You are opposites united In a hermaphroditic plan, Perfection, Completion, Wholeness, No longer a person divided Into separate houses, Separate camps; Your genitals--penis and testicles-- And your jutting woman's breasts And buttocks transform you, Save you from the curse With which the rest of us are cursed, Remaining only men or women Instead of a goddess Born of hormone therapy, Surgery, And a desire to...

Autobiography of a Shemale

Autobiography of a Shemale Dominatrix By Barbi Satin Introduction Among many in the transgender world the term shemale is offensive. Transsexual in considered a proper, politically correct term. Transsexuals are persons born into the wrong gender and have the psychology and even brain structures of the opposite gender. They go...

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...

Passionate Sex with a Beautiful Shemale

a 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 her to break out in goosebumps. She...

My first time witha a shemale

I was holiday in Spain with my friend and his Mum when i was 17, we didnt have any problems getting served in the bars so went out every night drinking. Half way through the holiday we all went out and me and my friend ending up in a club quite the worse for wear, a girl was dancing against a pole and keeped looking at me so i look backand maintain eye contact, she danced in my direction so i danced up to her and as she started to grind against me i started feeling her tits, she turned round...

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...

The Epiphany of Pain and Soliloquy of the Shemale

THE EPIPHANY OF PAIN The belt rose, ceiling high, And fell, hard, upon my buttocks, Which were arched to receive The painful, slashing strokes: Ten times, the leather strap Smote my cheeks or cleavage, Each swat harder than the one That came before, until I thought I'd faint and tears had gathered, As an army of repentant reprobates Doomed to an agonizing fate. Three times ten times more, the belt Fell, ever harder than before, And now my bottom's not only sore, But the...

Sweet Julie Birth of a Shemale

Sweet Julie Birth of a Shemale by Mistress Tawny Suede Chapter One Is It Just a Role? The dress rehearsal for the drama club's latest production was over. The curtain fell, the audience of excited parents applauded enthusiastically. The curtain rose and the performers stepped forward to take their bows. The curtain fell again and still the crowd applauded. The two stars, Troy and Julie, took their positions centre stage, holding hands as the curtain rose one more time. They...

I Was a Reluctant Shemale

Author notes: I wrote several stories back in about 1995 or so, but due to certain circumstances, I ended up purging them off of my computer. Over the years I have found those stories on the net and resaved them to my hard drive. The story you are about to read is the most recent story that I have found. It was harder to find because it has been posted to a site (Kristen's Archives) by someone else claiming it to be their writing. It is not. It is my story and I am now reclaiming it...

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...

The House of Shemales

Rudy stands about 5'9" and weighs about 140 lbs and if you look at him say from 9' away would think he is an attractive lady with a real short haircut. Rudy was tired of the old hangouts and he saw a large building that said The House of Shemales. First, he passed it but than turned his car around and went to the parking lot. After about a 5 minute hesitation he went inside out of curiousity. The lights were dimmed and the first thing he noticed were really attractive passable...

Sunday afternoon with 2 shemales

It is Sunday afternoon and I had a rough night. Ricky has been away for 3 days on business. I have been horny all night and morning. I used my toys but I need a warm body. A cock. I called Mark and asked if he was available but he told me was working a double shift and wouldn’t be finished till the morning. I called my girlfriend Carol and she told me she had a male friend coming over and plans on having a great time. I called Ricky and told him of my problem; I needed to get fucked and I could...

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...

Truckstop Shemale

True Story. Coming home from a late-nite clubbing excursion at around 3am I realized I was passing one of those big truckstops and instantly remembered that I'd always wanted to get picked up by a trucker, suck and swallow in the cab and be on my way.....just a kinky little fantasy of mine. Well, I was feeling a little too frisky to deny myself a chance to pull this off, so I pulled off the freeway and into the truckstop property to have a look around. What I discovered is that the trucks all...

Dominated By Shemale

By : Sam2mas Hi this is Sam and I am going to share my experience with a Shemale and this is true. Once I was travelling in a bus and I was seated in the last row and my next seat was empty. After travelling for 30 min a stopping came and some people came into bus. A lady around 35 came in and took the seat next to me. She was wearing a shirt and a mini-skirt. Her boobs were 34 D and she is looking sexy. After sometime she started talkingand we introduced ourselves and I came to know her name...

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...

Different Pleasure Fucked a Shemale

Hi ISS readers, I think all you know me. For the new readers, at first I introduce myself. I am Moni, late 40 and 5’-7”. I was born in a middle class Bangladeshi Muslim family and serving in a public organization. My whole life is lustful indeed. As I gained some practical experience about sex at my childhood, I became a sex-maniac and whenever I got chance I tried to fuck any aged girls or women with many tricks without applying force or at least to peep the uncovered boobs and pussies from...

Sex With Beauty Shemale

Hi everybody.mera naam Imran Hai.main 35 yrs ka hoon aur kolkata mein rahta hoon.Aaj main aap ko apni ek aur real storie batane ja raha hun.Ye kahani aaj se almost 6 yrs pehle ki hai.Main dikhne mein average honaur bi seual hoon.Ladkiyon ke sath bhi sex enjoy karta hoon aur ladkon ke sath bhi.ladkon ke sath main pure top hoon.yun to mujhe chodna aur chuswana pasand hai lekin chuswana mujhe zyada pasand hai. Aur bhi zyada maza aata hai jab mera partner elder ho.Ab main start karta hoon meri...

Passionate Sex with a Beautiful Shemale

Will 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 her to break out in goosebumps. She turned to face him, wrapping her arms around his...

A night with two shemales

I’m an oil geologist and spend considerable time traveling to the Gulf of Mexico. . I stand 5' 10" wet, have wavy brown hair with already early bits of gray, (which runs in my family). Good genes have also blessed me with keeping the fat off. With moderate exercise I match up well against guys who power exercise once a day. My face has been described as triangular and my eyes are blue with bits of gray. I'm said to have a good personality and women always tell me they feel comfortable around...

Lesbian Shemales

Melissa lay on top of me, one hand gently groping my breast while her tongue explored my mouth. I ran a finger down the crack of her ass, stopping to gently massage her ass-hole through her thong. A small whimper escaped her lips as she ground herself against me, her hard cock rubbing against mine. She pulled away from our kiss and straddled my hips, her weight resting on my cock. She looked amazing. Long, wavy brunette hair framed a delicately feminine face. She reached behind and unclasped...

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...

Untold Love 8211 21 My Wife With A Shemale

On the weekend night, my wife had told me that she would wake up a little early next morning and will have a massage from the girl that would be sent by the neighboring Bhabhi. Next morning, I too woke up at 10 AM and found my wife missing from the bed. I knew she might be in the guest room having a body massage. I went to kitchen, had breakfast and after going through the news papers, thought of going down and peeping in to the guest room to watch the massage and the girl. When I reached close...

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