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3 years ago
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Shemale Aunty Ne Gaand Mari

Sanket : Iss kahani ke saare vayqukti ek kalpana ka hisa hai. Agar aapka nam kisi se milta hai tho ye ek saiyog hai. Iss kahani mein gay sex hai. Agar apko ye sab pasand nahi tho mat padhiye. Yeh kahani bohot lambi hai aram se padhna. Iss kahani ke liye mane kayi kahaniyo ke ideas liye hai. Agar aap mujhse baat karna chahte ahi tho email kare : Mera naam Tanish hai, mein 21 saal ka bisexual ladka hoon jisse marna aur marana dono bohot pasand hai. Yeh tab ki baat hai jab meri 12th ke exams...

Gay Male
2 years ago
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SheMale Pussy and Cock

I once had a friend who always said "never fuck anything you can't bench-press". He was right, the biggest benefit of having sex with someone smaller and lighter than you is you can lift them easily !On a recent trip to Thailand I couldn't take my eye's off a stunning, short, tiny but beautifully proportioned woman sitting on the bar-stool close to where I was eating.She had a silk-blue clinging chinese style wrap on with a huge slit running all the way up her thigh revealing a beautiful...

4 years ago
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Shemale boss fucking

God, I felt like it wasn´t my day.I had been sent to the boss office one day and I tought that I was gonna gett fired or something like that.When I came into her office I saw that she was dressed kinda sexy. She was wearing a suit that had a lot of cleavedge. When I got there she said:-Do you know why I have called you here?-No. I answered-I wanted to ask you if you can come to my house tonight and have a litle chat. She said.-OkayWhen I got there I was a bit nervous. I knocked at the door and...

1 year ago
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Shemale Shock

My sister Louise was always trying to set me up with women she knew. Somehow she felt as if she were responsible for my love life. Louise's latest scheme was to throw a party and invite me and all her women friends that she could. I arrived at my sister's party and to her credit there were other men there besides myself. Unfortunately most of the women there didn't interest me in the least. Some were real tarts, some were loud drunks, but most of the women didn't know I existed. One woman there...

2 years ago
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Shemale Fantasy

I had wanted to be with a she-male for some time. I had purchased several she-male DVDs and found that being with someone as sexy as that really turned me on. I would fantasize for hours on end about being with one of those 'special' girls. Several of my male lovers couldn't understand my attraction to these women. They didn't see why I would want to be with a she-male when they were more then ready and willing to fuck my tight ass anytime I desired. Well the big thing for me was the fact that...

4 years ago
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Shemale sex is Best

I had been in sex with gays for 1 year, but had always been intrigued by those hot looking chicks who packed more than a pussy between their legs. I had no idea where to find one in Pune I was definitely bi-sexual, still seeing whores, and still going to gloryholes for my cocksucking needs. Pune was a dream come true for me, I found a beautiful girl to have some really hot sex with. For a total slut like her, it was like dying and going to heaven. On my way into the street one afternoon, I saw...

Lesbian
1 year ago
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Shemale Fantasy Suck Fest

This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behind me. It's all there laid out on the bed and on the dresser. It's my outfit for the night along with the makeup. And everything is just the way I like it. Before I get changed let me tell you a little...

She Males
1 year ago
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Shemale Surprise

I'm a country boy. About a year ago I left my small town and moved to the city so I could attend university. Initially, I had nowhere to stay so I was going to move into my cousin Mike's flat for a few days with him and his room mate, Sandy till I found somewhere of my own. Mike and Sandy worked together at a law firm in the city. Mike had a fiancee` but he didn't live with her because he didn't want to upset her parents who were very traditional and devoutly religious. Actually, I found it...

She Males
1 year ago
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Shemale customer in a strip club

I am an exotic dancer, one night a couple came into the club, he was late 40's or so, handsome in shape and rich looking, she was very sexy,mid 20's, tall with a low cut top showing off her great boobs, I am bi and love dancing for women, it is not uncommon for a guy to bring in his woman and buy her some lap dances while he watches. It is a big turn on for me, I really enjoy doing it. So after they sat down I went over and introduced myself and asked if they wanted a dance. He said she would...

She Males
2 years ago
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Shemales The Martini affair Part 3 finale

I could not stop thrusting back with my ass on her face as her tongue went crazy over my anal clit and tight bud. But I could not take it for long as I fell to the floor turning around to face her on my back. As if knowing what I had in my mind, she looked into my eyes and slowly took my cock throat deep in her mouth. Just as she did that I pulled her ankles and she knew what I wanted.So very gently she moved her hips towards me and came over me with her glistening throbbing precum weeping cock...

3 years ago
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Shemales in Barcelona

due to my job, I had the opportunity to travel a lot. Once I had to travel to Barcelona and the complexity of the meetings required that I had to stay there for about 2 weeks for consultations with customers. After long working hours, normally we went for a nice dinner (nothing better than begin the evening with tapas and wine or sidra, concluding with a excellent dinner and a nice Rioja wine (or a white Albarino, one of the best kept secrets from Spain)After I was left in the hotel I searched...

3 years ago
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Shemales better than males

It is 10:00 a.m. When she gets to my place. She shuts the door, locks it, and well, we attack each other. Oh god her kisses are so sweet….caressing the soft smooth flesh against mine, nipples hardening, hot breath wisping across my breast. She pushes me back into the bedroom and across the bed. She grabs the lotion and starts massaging my legs, going up and down my inner thighs just slightly touching my clit. She, then, leans over and starts kissing and licking my thighs and groin area. I feel...

Lesbian
3 years ago
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ShemalePrey com

(Apologies that this is not in the Guidelines, but the term 'shemale' is used only for the purpose of erotic fiction and should not be as a term or to represent trans women in real life. Apologies to any people it may offend) As the alarm clock goes off on my phone and your mom shouts your name 'Ryan' to come down for breakfast I jump out off bed to look at yourself within the mirror. I find to see a 19 year old naked body looking at myself, at 5'9" ft tall, a lean body which sports a few good...

Transsexual
3 years ago
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  • 19
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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...

1 year ago
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Suprising Shemale

A storm had just passed and the asphalt glistened as he crossed the street. Fuck I’m horny I thought. As I crossed the street I saw this beautiful black girl walking crossing the street towards me. It was dark and she was completely unafraid. Normally I would not have had the courage but I was kind of drunk so I asked if she was coming home from a hot date. To my surprise she turned to talk to me. Unlike many black girls she was slim with slight hips and small breasts. The had long...

1 year ago
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The life of Jamie a well endowed shemale

7:25 AM: The buzzer on Jamie’s alarm goes off and she lazily pushes the button to turn it off, she gets out of bed, stretches, pull the blinds open and lets the sun-shine in, she looks down at her crotch and notice an extremely big hard-on. Normally she would just jack-off in the morning, but today she had to rush a bit, so she prayed her erection would go away after she went to the bathroom. When she got finished, her cock was still hard and wasn’t showing any signs of getting flaccid. She...

1 year ago
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Long sex story 8211 I Was A Reluctant Shemale

Marilee’s fists tightened in despair as she sat at her secretarial desk and listened to the muffled moans emanating from the office of her boss, JC Wyatt. JC was one of the youngest and most famous casting agents in Hollywood and was the most blatant offender of the “casting couch” which degraded women. The young actress, a stunning blonde who couldn’t have been more than sixteen years old, had looked so hopeful when she had entered that office only twenty...

3 years ago
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My Boss Is a Shemale

I slowly put my tongue on it. It’s so hard and solid. I feel like I could break my skull on it. I can feel her breathing and shiver as I slowly put the head in my mouth, so warm. I alternate between suck the head and licking the shaft, even giving some attention to the balls. I had a really bad week. Actually, bad would be an understatement, shitty would be more appropriate. Problems after problems had punctuated my Days. I managed to get a new job as an assistant executive at an...

2 years ago
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Wanking with a shemale

Every couple of weeks or so I go a get a hooker. I have a few favourites. All of them have big tits and either I watch them play with them whilst I jerk my cock, or I let them jerk it for me. But that’s where I have some trouble. Whilst these girls are beautiful, I know they have never had a cock, and I don’t think they know how to handle one. So the last time I went for a handjob, instead I browsed around for a she-male. She was stunning. Perfect female facial features and body...

3 years ago
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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...

3 years ago
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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...

4 years ago
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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...

1 year ago
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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...

4 years ago
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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...

Trans
4 years ago
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Create a Shemale

*Author’s note: This story is Public, if you have an idea, start writing!* Robots, science and chemistry have all advanced further than the public is aware of. Due to patents and trade secrets, nobody knew it was even possible to create a sex bot. They can have gravity defying shapes and sizes. They can even alter their owner with chemical cocktails. Cockbot Inc took all these ideas and added a penis. Their robots only come with a penis. You think, well, it’s better than nothing, and set to...

3 years ago
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Fuck a shemale

Congratulations! You've been selected by AR Industries to take part in their AR Sex Suite Programs. Based on the responses you gave on our survey, we've determined that you have an interest in screwing chicks with dicks. Before we begin, we'll just need to figure out what exactly you're looking for: your partner's race, breast size, penis size, and outfit that they're wearing when they meet you. So, let's begin.

Fetish
4 years ago
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Celebrity Shemales

Here, you can fuck the shemale version of your favorite celebrities! Feel free to add new celebrities! IMPORTANT: Leave a like for whichever celebrity you want me to write a shemale story for first!

Transsexual
3 years ago
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Scarlett Johansson shemale

You pull up to the house of Scarlett Johansson. You get out of you Mustang and walk up to Scarlett Johansson's door. Before you can knock on her door she opens it. "Oh hi Vic," Scarlett says "why don't you come in." You walk inside and take your jacket off. "So what brings you here" Johansson says. "Just want to see how my favorite actress is d-" before you can finish Scarlett takes of her shirt and kisses you. "why don't we have some fun" Scarlett says and pusses you on her couch and continues...

Transsexual
4 years ago
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Cree ta propre shemale

Un homme dans la rue vous as aborde. Il vous a donne un papier avec une adresse, vous etes curieux n'ayant pas compris ce qu'il vous voulait. Une fois arrive a l'adresse vous entre. C'est une boutique plutot classique. Vous approche la vendeuse et lui donner le papier. Elle vous explique que vous avez ete choisis pour tester une machine unique. Vous allez tester une machine a cree des shemales. Vous penser d'abord a partir ensuite vous vous dites que ca doit etre un jeu un peu stupide pour...

Transsexual
4 years ago
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My best friend s a shemale

I had known her all my life, even before she became a girl.My name is Johnny and I am eighteen years old. I am not the most handsome guy around, but I good looking enough to hook a sexy girlfriend. That girlfriend used to be my best friend, a guy.Jesse was always an effeminate guy. He was soft spoken with soft features. He was always shy, but not with me. He always had long hair and when it wasn't tied into a man-bun he looked very much like a girl.Shortly after his sixteenth birthday, he told...

Trans
3 years ago
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Pure Shemale

I’m Bobbie and I’m your every dark, dirty fantasy come true. I’m not some surgical chop shop masterpiece, I am the real deal, a hermaphrodite, born true with both sexes, I’ve got a dick, and a pussy, and I love to fuck with them both, at the same time if I can. More than just a genetic anomaly, I prefer to think of myself as blessed. I don’t need hormones to avoid shaving or give me tits, my tits are perfect, all natural C cups, perky and round. I’ve kept my body trim and slim, but dyed my...

Fetish
2 years ago
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The Dirty Little Shemale

I am Nicola, a 25 year old shemale. I am 5'7", slim, athletic, I have shoulder length light brown hair, green eyes, 34D tits, a 6" cock and am a dirtly little fucking slut that will do anything. It's Friday night and I head to the local club dressed in my tight black top that I'm almost coming out of, very short denim skirt that only just covers my crotch, sexy black panties and black leather knee high boots. I get inside and the club is packed. There are sexy men and women everywhere I look. I...

Fetish
1 year ago
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Taken by Surprise 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...

3 years ago
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Taken by a sexy shemale

I was getting pretty horny that week; since my sweet wife had gone out of town to attend a conference.I talked about it with some of my office mates and one of them, Jimmy, said he had the perfect solution for me.He said he had a she male friend; a hot ass girl with a huge cock.I laughed, saying I was straight and did not want a cock in my ass.But Jimmy convinced me that the she male had an ass to die for.I finally accepted and I made some arrangements with this sexy she male, to meet at a...

1 year ago
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First time with a surprise shemale

So me and my friends were out for a few drinks in town. After a few beers in the bar we decided to hit a club on our we up to the place i seen this sexy girl in line she was tall, long dark hair, big tits obviously fake but real nice she was wearing a short white dress showing off her sexy long legs, wearing nice high heels. Just looking at her was giving me a semi. I seen she got in and was keeping an eye were she was going. After we got in with little trouble from the door man we headed...

2 years ago
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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...

3 years ago
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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...

2 years ago
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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...

3 years ago
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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...

2 years ago
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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...

3 years ago
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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...

3 years ago
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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...

3 years ago
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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...

3 years ago
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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...

4 years ago
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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...

2 years ago
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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...

2 years ago
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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...

1 year ago
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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...

3 years ago
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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...

3 years ago
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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,...

2 years ago
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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...

3 years ago
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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...

3 years ago
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The Morning After Pt2 Wow Public bondage Shemal

Irea talked with Rosa for a while in between mouthfuls of scrambled eggs and small bites of bacon; inconsequential things really, just small talk and friendly jokes while the inn woke up around them. The usual regulars wandered in from their homes in the wan hours of the morning as the rising sun shone through the windows, a few casting lustful glances in the bound demon hunter's direction. Most noticed she was occupied talking to the friendly death knight, but a few approached and began to...

2 years ago
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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...

3 years ago
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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...

2 years ago
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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,...

3 years ago
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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...

1 year ago
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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...

4 years ago
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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...

3 years ago
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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....

4 years ago
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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...

4 years ago
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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...

2 years ago
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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...

3 years ago
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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...

4 years ago
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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...

3 years ago
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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...

3 years ago
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  • 18
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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...

2 years ago
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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...

3 years ago
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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...

3 years ago
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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...

3 years ago
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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?...

2 years ago
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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...

3 years ago
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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...

3 years ago
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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...

1 year ago
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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...

2 years ago
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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...

1 year ago
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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...

1 year ago
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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...

2 years ago
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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...

2 years ago
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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...

2 years ago
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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...

2 years ago
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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...

2 years ago
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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...

4 years ago
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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...

2 years ago
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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...

3 years ago
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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...

4 years ago
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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...

1 year ago
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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...

Gay Male
4 years ago
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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...

Gay Male
4 years ago
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  • 21
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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...

Gay Male
3 years ago
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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...

Gay Male
1 year ago
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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...

2 years ago
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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....

3 years ago
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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...

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