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Shemales Porn Stories

don b an glendaa at drive-inn part #3

Gay MaleShemalesMature

don b asked me after our hotel if we could go to the 5 drive-inn in oakville ,ontario next saturday night , i said yes. i have always liked sex at the drive-inns and i got dressed for don b with this in my mind. i was so looking forward to some hot sex in his car . my toes were painted red and i decided to wear a garter belt and black stockings with the reinforced toe and heel and seam up the back ,red thong and high heel open toe mules, with my black and pink bra over which i wore a black see-thru blouse and my short blue skirt . my fingernails painted red and my short greyish colored wig and… Read more

Posted by glendaa 21 hours ago 1 435

Jill and Joan

FetishHardcoreShemales

Jill and Joan Joan saw Jill giving her a leer, she giggled saying “you must be horny”? Jill sat beside her smiling then reached under her skirt, feeling her crotch, Joan said, “Honey, I'm tucked deep”. Jill rummaged into Joan's panties, slid a finger down her cock and felt it going under her saying, “you have the head inside you”? Joan grinned “yes”. Jill leaned over Joan kissing her as she cupped her crotch and began pushing Joan's cock deeper into her as she felt it thickening. Joan slid lower as their kiss broke and spread her thighs wider… Read more

Posted by GurlTown 1 day ago 892 100%

My New Trainer byNearMiss

ShemalesAnalFirst Time

"So, do you need a spot?" she asked. Wisps of red hair, which had fallen from her pony tail, framed her face as she looked down on me. "Ummm sure," I lied. The equipment at the bench press station where I was working out was designed to be used solo. With a quick flick of the wrist I could lock the bar into any safety position, if I had gotten into danger, but accidents do happen and you can't be too careful. Besides, I wasn't going to turn down help from the most beautiful girl in the gym. She also happened to be the only girl in the gym at this late hour, but she was still hot as hell.… Read more

Posted by mooolemooola 1 day ago 8 1,470 100%

Afternoon

BDSMShemalesHardcore

Thanks Michael... On second thought, maybe I shouldn't have said yes. This experience has turned out to be much more than what I expected. The amazing combination of discomfort- muscles and joints pulled into places where they don’t belong- and the tightness is almost too much. My body is completely invaded… My mouth is open enough to breathe, though the hood blocks all but muffled sounds. I can’t speak because my face feels constricted, pressed tight all around by the delicious leather. The smell alone is enough to send me to the brink of orgasm. The thing inside my sex is not a simple… Read more

Posted by rtialooking2 2 days ago 964 100%

Boss Turned me Into a Shemale

FetishFirst TimeShemales

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 office and closed the door behind me. "Chris, what's the darkest secret you have?" I still didn'… Read more

Posted by 425olds 2 days ago 2 4,414 81%

Sissy Rules - Reads like a proper job description

ShemalesFetishHardcore

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clitty Rule#2: A sissy wears a bra and panties Rule#3: A sissy loves cock Rule#4: A sissy loves cum Rule#5: A sissy takes it in the ass Rule#6: A sissy loves pink Rule#7: A sissy loves her toys Rule#8: A sissy dresses like a slut Rule#9: A sissy shares Rule#10: Sissies love facials Rule#11: A sissy must have a tight ass Rule#12: A sissy must have perfect bimbo makeup Rule#13: A sissy grows big fake tits Rule#14: A sissy is a pro cock sucker Rule#15: One is not enough Rule#16:… Read more

Posted by Liliiflora 3 days ago 780 100%

Julie out on her own – Bowling Aftermath – CD/TV/T

ShemalesFetishGay Male

Julie out on her own – Bowling Aftermath – CD/TV/TS, MM So last time I wrote about how my roommate Mike hooked up with flirty Vicky at the bowling alley, how I knew about it, how Mike knew I knew, and how Vicky knew I knew, but how Vicky didn’t know that Mike knew I knew. Confused? Read last entry! Anyway, when Mike and I got home that night, we thought it was hilarious how Vicky’s horny lusts had gotten the better of her, how she’d blown Mike in the bowling alley men’s room while I watched over the stall wall, and how he’d accidentally cum a little on her blouse. Now she sort of owed me a f… Read more

Posted by BeehiveTV 3 days ago 2 775 83%

Carla and Mike

AnalFetishShemales

Carla and Mike Carl and Mike had been high school friends. Both were average students, Carl better in the classroom, Mike a natural jock. Carl chose college, Mike the military. After being separated a decade they were meeting again. Carl had been an introvert, often the subject of rumor of being gay. Yet never in school had it ever been proved. Mike didn't question and had been a “girl slayer”, but they had a mutual interest in the “Old West” since Carl's great grandfather had been an actual lawman. Carl now lived out west, 40 miles away from t… Read more

Posted by GurlTown 4 days ago 4 1,519 100%

Velma Dinkley's Dirty Secret Part Two

ShemalesBDSMMasturbation

"How..." Velma gasped, blancing horribly. Her hands shook so badly it took her a full minute to open the door. When she did, her eyes fixated on the smartphone she'd seen through the peephole. She watched herself masturbating as her lips moved silently. "Should I turn up the sound?" a firm voice asked almost sweetly. At the sound of it, Velma started so hard she nearly leapt out of her shoes. With a little laugh, the stranger shut her door, turned off the smartphone, and slipped it in the side pocket of her white jeans. The stranger was a very tall, toned, black woman with piercing, brown,… Read more

Posted by TheMidnightTalebeare 5 days ago 4 878 83%

Caught dressed - what happened after .......

ShemalesGay MaleHardcore

Hi All this is what happened after i got caught by another guy while i was dressed ( Read the intro here http://xhamster.com/posts/745048 ) Well on to the real thing now.... I just sat there in my room smoking and thinking whether i should call him or not. Well a cpl of drinks and a smoke later i decided if he wants me as a gurl then i might as well have a bit of fun myself. So i called him on the room phone...he picked up in 2 rings Me- Hi.. is that Rajesh ( lets call him 'R' from now on ) R- Yes who is this Me- I am from 201 R- ohh ... Hi ..I thought you wouldn't call What's your na… Read more

Posted by hornyboyind 7 days ago 4 2,986 100%

Fun at Bangkok

AnalShemalesFirst Time

On Holiday and Pick up A ladyboy Hooker for some sexy fun As I drove my rental car through the crowded streets of Bangkok, Thailand I stared at the dozens of ladyboy hookers touting for business on the streets. I have always had a thing for transsexuals. Ever since I can remember I have trawled the internet for pictures of shemales and trannys. I just love to look at their huge dicks and big shemale tits. I spend almost every night either looking at pictures or watching pornhub videos of shemale sex. Sometimes I also use a live tranny webcam site and interact with them on there but it has alwa… Read more

Posted by hunter043 7 days ago 2 2,522 90%

What Internetporn did to me and my ex girlfriends

ShemalesFirst TimeTaboo

I love to collect porn in all kinds of ways and use a program called picassa 3 , an video editing tool from google which they stopped supporting and changed to a new program (Which completely sucks in comparison) . I love to make prinscreens and then edit al those dirty pictures of woman getting destroyed and degraded little by little. It came to such an perverted mindset that i wait for the shot that captures how the slut is actually suffering...or gets surprised by cumshot or a pisslaser in the nose or when she almost had to gag and puke ...which i love ofcoursese .. But why , am I sick? Wh… Read more

Posted by Anoniema 8 days ago 1,546 100%

Business trip with rough fuck. <3

ShemalesAnalHardcore

It´s June the 11. 2018. This evening i was on a business trip and my mistress Mrs_Petra ordered me to write a paper as i took my dinner in the hotel restaurant to tease a guy and to show what a bitch i am. I asked the waitress for a paper and a pencil and started to write the following text on the paper. "Hello sexy bull, i am a submissive trans bitch who love it to be used. I am wearing sexy lingerie under my jeans and shirt you can see them when i walk away at my back. I will lift my shirt if i walk away. If u are interrested to use my service as a dirty sub slut for free give me a sign and… Read more

Posted by Tina_the_Kitten 8 days ago 1,566 100%

Karen My School Teacher 18

FetishShemalesTaboo

Karen, My School Teacher - Part 18 By HosieryQueen Part 18 I felt a bit frightened that she just left me like this. I looked in the mirror, but I couldn't see anything at all. Just me with a pink ballgag in my mouth, a pink dog collar with ‘pantyhoseslut’ written on it, all bound up. I felt something start vibrate. It went straight to my horny pussy. “Mmm!” Then the machine shoved the dildo, shape gently in my pussy. My god, she wasn't k**ding. It started feeling good. “Mmmm...Mmm!” The next ten minutes were just pure pleasure, but the more I started moaning, the more violent the machine… Read more

Posted by HosieryQueen 8 days ago 4 1,733 57%

Crossdressing and Jocks (Part 1)

ShemalesFirst TimeGay Male

what they don’t know is that I still dress in women’s clothes to this day. I always longed for my sister to leave the house so I could sneak into her room and wear her panties. My parents running on on me wasn’t a problem because my dad lived across the country and my mom had to work two jobs, so growing up, I pretty much raised myself. I was a year younger than my sister, and when she hit puberty, that’s when the fun really began when her wardrobe updated with bras, thongs, crop tops, short shorts, and other slutty clothes. My sister was especially slutty, and I don’t blame her, seeing as we… Read more

Posted by EllaRoseCD 8 days ago 1 1,920 100%

sissypuss sucks hot black man

First TimeGay MaleShemales

Hi If you have looked at my hamster profile,its obvious that I am a sissy that took the long road to accepting and eventually be quite proud to be a sissy cocksucker. Today ,I had a vacation day to use up so I couldnt decide if I should put on my faavorite outfit and drive an hour to a great adult video/bookstore or spend the day in the sun at a close by "clothing optional" spot in the woods by a beautiful stream. The weather was forecasted to be 80 with no clouds and no humidity.. A rarity where I live and even more rare so far this late spring. If I went to the video store I would have my f… Read more

Posted by sissypuss 9 days ago 1,575 100%

She turned into a Shemale

ShemalesTabooFetish

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 together. The connection between us was intense, and passionate with little grabs and pull ins with… Read more

Posted by pyxxx 9 days ago 2,335 100%

Waiter to waitress

AnalShemalesFirst Time

I cant believe that I finally dressed up like a girl. I was living down the beach at Cape Cod {CC} for the summer .I shared a large 3 BR {Bedroom }house with my sort of GF, 2 other girls and some dude without a job.{He was selling MJ but was buddies with the landlord.} We had to share one bathroom and it got a bit hectic with bras, nylons and tampax all over.I am about 5'9 '' with strawberry blonde hair. I was in good shape from jogging but had one constant problem. 3 inch cock.My GF was giving me less sex and… Read more

Posted by robin48 9 days ago 4 2,705 92%

Aunty Honey Part 1

ShemalesMatureGay Male

Aunty Honey invites me to visit her Part 1 It seemed strange to receive an invite from my Aunty Honey, I hadn’t seen her in years, though when I was younger I used to be a regular visitor. Still I thought, how nice, the old girl still remembers me! So I bought a train ticket and went to her house once again. Knocking on the door it all came back, how she seemed just a little different from my other relatives, I was much younger of course and I just couldn’t quite put my finger on it, anyway, too late! The door swung open and there she was. Just as I remembered, tall, certainly classy, slightl… Read more

Posted by ff365 10 days ago 8 3,329 96%

Jesse (Jane) and the Landlord

ShemalesFirst TimeGay Male

James was in guy mode, but sitting like a prissy princess, browsing his favorite online crossdresser store, looking at lingerie, breast forms, and sex toys. He was just about to hit the “check out” button, when suddenly he heard someone at the door. Knock. Knock. Knock. James quickly shut his laptop lid. He cleared his throat and checked the door. It was his Landlord, Ronald. He wasn’t supposed to be here for another fifteen minutes. He guided him in to the kitchen. It was rather hot that day, so James was wearing an old gym short-shorts. James could feel Ronald’s eyeing his legs. "Would you l… Read more

Posted by EllaRoseCD 10 days ago 4 1,826 75%
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