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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...

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...

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...

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

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...

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...

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 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?...

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 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...

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...

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...

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...

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