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Shemales Porn Stories

Discovery

ShemalesTaboo

"What the hell are you doing!!?" I heard my s****r scream. My eyes snapped open, my hand flying away from its grip around my cock. With our parents away and my s****r out I'd thought I'd be alone for the evening and decided to have a wank. Now Michelle had come home unexpectedly and discovered me. It got worse. "Are those my knickers you're jerking off into?" She screamed again. I nodded shamefacedly. "You little shit. I'm telling on you." "Please don't Michelle; I'll do anything you want." I pleaded. She looked down at my lap where her panties were still wrapped around my now wilting… Read more

Posted by sparkyking 3 years ago 8 8,752 97%

A new fur slave

FetishHardcoreShemales

A new fur slave I’m laying here fucking another hooker, a rabbit hooker, and I’m about to cum and this is where my story begins. "Take my hot horse cum, slut!" I grunt as I cum in the rabbit’s pussy. My cock grow bigger as each string of cum stretches my cock and her eyes widen as her pussy is opened wider until my cum reached the head and flows straight into her womb. Three more strings shoot out and her belly grows bigger with each one until she looks four months pregnant. I lay her down on the bed having fucked her in a chair and pull my cock from her tight pussy watching my cum leaki… Read more

Posted by pinki-husky 3 years ago 1,099 88%

Closet Crossdresser Fantasy

FetishGay MaleShemales

I find your ad on CL and we exchange a couple of e-mails. You tell me you have some of your wife's things to put on me, my stiff cock pulses harder. I show up and you invite me in. You're a larger gentleman that is in need of some attention. You offer me some wine and then show me to the bedroom. You open the drawer with her nighties and let me pick one. I find a stretchy red camisole with some matching red fingerless gloves. Then you pull open her panty drawer. I rummage around while noticing the tent in your grey sweatpants. I find a black spandex thong that feels so nice an… Read more

Posted by cumquarts 3 years ago 2 1,762 100%

Sissified for three cocks

FetishGay MaleShemales

I think you are about ready my wife “Jen” exclaimed and she rotated me towards the mirror. My cock was already rock hard and sticky soaking the silky panties as I looked at my reflection. I gazed at my blonde shoulder length wig bounded into two braided pig tails, my face heavily coated in foundation, my eyebrows and lashes painted dark, around my eyes multi shades of blue and my lips a glossy pink. I could feel the silky tiny cup bra as it rub across my nipples, I could feel the top of the multi colored leggings clasping my thighs with the feeling of the tiny skirt that just covered my pantie… Read more

Posted by iheartm2f 3 years ago 7 3,547 100%

STORY of SkyDancer

AnalGay MaleShemales

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 home since I was so beat up. I told her I was just doing my job but since my glasses we… Read more

Posted by ClassicCockx 3 years ago 3 1,802 92%

My Big Sister Ch. 02

Shemales

My head gently landed on my desk as the last bell rang, signaling the end of school. Usually I'd be the first one out of the door, but right now I'm having....certain difficulties with the lower part of my body preventing me from doing anything too suddenly. "Yo, Pete!" Paul's voice caused me to suddenly jerk up in my seat, and that particular motion caused my ass to start burning once more. Paul noticed me hissing in pain, and arched a confused eyebrow at me. "Dude, you alright?" he asked as the students continued leaving the classroom. "Yeah....I'm fine," I groaned. "You just sta… Read more

Posted by sparkyking 3 years ago 7 4,026 95%

Sissy Son Taken to Costume Party

Shemales

I was making my way to my moms and dads house to house sit for them as they were going to a party that night and I had agreed to be there to watch the house and hand out candy. I was going to be alone in the house. I loved being all alone as it gave me a chance to partake in my fetish of dressing up in girls clothes. My s****r still lived there and she had some of the best lingerie anyone could ask for. So I gladly accepted watching the house almost as soon as mom asked me to over the phone last week. I made sure to grab an overnight bag as mom said I could sl**p there and head home in the… Read more

Posted by sparkyking 3 years ago 9 4,319 98%

My Big Sister

Shemales

I must say I never pictured this event happening to me in my lifetime, I mean I'm a pretty well rounded k** living in a quiet suburban town. Nothing big happens here, and I'm not some guy that's always finding himself in trouble, so getting bent over and fucked in my ass was the last thing I really worried about, unless I was gay of course, which I'm not. But no, here I am at eighteen years old, a grown man feeling his ass burning as I try my best to sit comfortably at my desk. As the instructor goes on and on I find my eyes darting back and forth around the room, making sure no one looked… Read more

Posted by sparkyking 3 years ago 8 14,441 99%

Start of a new life

BDSMGay MaleShemales

One day I got a text massage on my mobile while I was at work, it was from an unknown number, it said come home now. So as I only work down the road from where I lived and also I was just going on lunch so I made the 5 min drive home. When I got there, there was a man standing in my door with a box in his hand. When I got to him he said do you live here and is your name Lucie, I said yes but a bit puzzled as I only use Lucie when I am dressed as a girl. He said good now open the door and let me in. After we got in he gave me the box and a letter. I read the letter it was from my master, it sai… Read more

Posted by dallasrose 3 years ago 9 6,653 84%

A New Dawn Arises

FetishShemales

A New Dawn Arises - Chapter 1 The Arising To celebrate my transformation and to increase the effect of my feminization, Mistress Lynn decided a name change was in order. "What's a good name for a useless, slut French Maid," she asked herself aloud. "I shall call you Dawn. I think it's appropriate because you are at the dawn of a new way of life." Another belt was strapped around my waist. It had a number of loops. My mistress attached my wrist restraints to the strap. This allowed me lim… Read more

Posted by klammer 3 years ago 2 3,598 86%

Double trouble

AnalShemales

First of all this is a true story. My name is Jessica Judd and ive been dressing for 15 years. Ive always been interested in putting on panty hose and panties but it wasnt till about 7 yrs ago that I really took it to a whole new level. Ive been with a couple guys while dressed but my last episode stole the show. I decided to rent a room at a local casino and gamble a little so I decided to take several outfits and all my accessories just in case I get wild. While at the casinos I began to loss my money too quickly so I decided to slow down and have myself a couple drinks. It was then… Read more

Posted by jessicajudd 3 years ago 4 2,642 100%

Boy gets Fucked by Shemale

AnalGay MaleShemales

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 necessary tools and went into my room. I locked my door so my mom wouldn't accidentally walk in on me a… Read more

Posted by ClassicCockx 3 years ago 24 9,907 98%

The Haunted Blue Jeans

Shemales

The Haunted Blue Jeans By: Jessica Rabbit "I hate extended business trips". This is the second time I have had to use the hotel laundry facilities. "It is bad enough to be gone so long that you use all your travel clothes, but then to have your company not reimburse you for the cost of having a laundry service perform this deed makes it even a more bitter experience", I thought as I rounded the corner to the laundry room. It's a small laundry room with only 3 washers and dryers, plus a table to fold your clothes on. As I dump my jeans, shirts, and Jockey shorts into the washer… Read more

Posted by lana100 3 years ago 1 2,122 100%

The Secret Manor of Trans-Supremacy Part 3

BDSMFetishShemales

PART 3. TS.MISTRESSES TRAINING THERE SUBS TOO STRAP-ONS... As one of the Manor Houses beliefs is in Sexology that came from Medieval times in sexual methods by Mistresses... Everyone should receive Anal with Thanks gracefully at all times, she says to the room... She f***ed me too take the Twister as she screwed it in then pulled it out over and over agian as I was in stocks bent over with my arse positioned that she could comfortably use my Pussy arse for her Sadistic desires in Fucking me with many Cocks and allowing the other ladys too train themselves in screwing male bitchboys… Read more

Posted by tvisabellacoupe 3 years ago 2,172 92%

The Secret Manor of Trans-Supremacy Part 2

BDSMFetishShemales

PART 2. MY LADY TRANSEXUAL MISTRESS JESSICA/JESSIE OF FINE OUTSTANDING, DIVINE BEAUTY... The lady says I should been taken upstairs as too change into what there requirements too stay with them here for a few days in Her chambers... before such she Tie's my Balls up with a bondage rope and pulling it backwards between my legs that goes through the sides on my harness & up through the O rings of my Collar too the Mistress standing behind me as I'm cuffed too the wall in front watching my Mistress in the Mirror as she pushes her stiletteo heel up my anus too that of pain & pleasure as of… Read more

Posted by tvisabellacoupe 3 years ago 2,119 100%

My son got seriously hot

FetishMasturbationShemales

Well, life sucked after divorcing my little sheboy, he was everything to me, but I had to let him go see the world, he went to college, after leaving his job as a freelance babysitter to find himself, he was very good at his job, he worked as a babysitter for a filthy rich f****y, he used to make over £400 in 6 hours spread over a whole week, sometimes he takes overtime, however this overtime was more like parentsitting than else. He would stay for a further hour to take care of the parents by getting into naughty games together, the couple were rather young, the man was just midway through… Read more

Posted by starlight8998 3 years ago 3 5,924 83%

Fuck My Bitch

Gay MaleShemales

I had exchanged emails and photos with Jennifer. She quickly answered the door and I noticed her plus size shape peeking through a sexy black teddy as she guided me in the room. As I stepped in the suite I saw the focus of my attention, Alexia. She was sitting on the hotel couch I was floored by her beauty. She looked a little Hispanic and Asian with blonde hair and black roots peaking through. She looked to be in her upper 20’s with a smooth face covered in a bright orange tinted foundation, light pink lips, light charcoal colored eye shadow all the way around her eyes with dark black eye bro… Read more

Posted by iheartm2f 3 years ago 3,130 100%

Party Favor(s)

Gay MaleInterracial SexShemales

My getting into Blue Mountain State U., in the early 1970's was a blessing in so many ways. For one thing it got me out of a bad living environment in my little "Hick Town". I got accepted on a Music scholarship, not Football or Basketball, like most Black students there at the time, so I had to make the most of it. Back then no one asked bout sexual orientation, but since I managed to become the Drum Major for our high school band it was assumed, that I was "lite in the loafers", for some reason. It just happened to be true, but like so many back then I buried it deep and tried to no… Read more

Posted by Keith_Walters 3 years ago 5 2,803 100%

Caught cumming

ShemalesTabooVoyeur

When we moved into our new house I got first pic of bedrooms, instantly I chose the bedroom in the loft with a nice big skylight, I love having the sun in my room and when it's raining I like watching it drop all on the window. One day I decided to have the blind open while I went to bed, waking up the next morning I had discovered my favorite place ever. I stripped naked and lay on my bed again, my huge tits flat on my chest as I lay there I began to wank. Where we had moved to was across the road from an all girls school, what I noticed was at the right angle I could see up under the bri… Read more

Posted by shemalecharlotte 3 years ago 12 13,933 98%

Honey poses for the Camera Club.

AnalGay MaleShemales

A fantasy of mine is to be the model for a Camera Club of older men. I would love to be the centre of attention as their point their stills and video cameras in my direction. I would first pose for some fully clothed pics and video - see through blouse, tiny mini skirt, stockings & suspenders and high slutty heels, lots of tarty make-up and trashy jewellery. Giving a flash of seamed stocking top, bending over and wiggling my arse, putting my finger in my mouth as I pull up my skirt to reveal tart red and black lacey panties bulging with my stiffening tranny dick. The sight of five or six older… Read more

Posted by honeybtgirl 3 years ago 20 4,428 99%