Shemales Porn Stories

HELPING MYSELF TO THE PLUMBERS HELPER

The plumber was nothing to look at short kind of fat ugly hair on his lip and he smelled like Ben-gay but his helper on the other hand was an a dream come true tall blond muscular with deep blue eyes I couldn't keep my eyes from straying to his crotch where a telltale bulge was visible...I knew the plumber thought I was a real woman but his helper kept stealing looks at me I suspected he was on to me even though I look totally hot as a woman and most times they can't tell some guys just know...he didn't look turned off if he did so who cares right...I showed them where the leak was it was comi... Continue»
Posted by laceysgirl 19 hours ago  |  Categories: Anal, Shemales  |  
2386
  |  
94%
  |  3

First time stallion

So there I am analysing myself in front of my hotel room mirror for a final check that I’m ready to greet my man when he knocks on my room door. Hair, brown shoulder length combed straight , check, Full makeup bronzer, blusher, foundation, mascara, eye liner and of course pretty pink lipstick all in check and a flutter of my false eye lashes for good measure . Perfect, one final pose for sassiness in my leopard print mini club dress being stretched at the breasts to accommodate my 34DD silicone bra infills. The bottom of my dress stopping just shy of the top of my super smooth silky black self... Continue»
Posted by dirtyjenna 1 day ago  |  Categories: Anal, First Time, Shemales  |  
1653
  |  
100%
  |  1

First time anal with a huge Dom cock (real story)

I was at home alone feeling really horny, I hadn't cum for about 1 week... I started watching porn and soon after I found myself on a dating website that I used to go on at the time...I was cross dressing occasionaly wearing stockings and knickers and I loved it. I had only sucked cock twice and now I needed more...
That night I started talking to someone who was crossdressing also, we chatted for ages and the conversation was getting more and more horny. He was looking to meet the day after, I was anxious about the whole thing but I was so horny that I was ready for everything...At some poin... Continue»
Posted by lidacd1 2 days ago  |  Categories: First Time, Gay Male, Shemales  |  
2794
  |  
90%

sissy rules

sissy rules to live by

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 suck... Continue»
Posted by bigsissy 2 days ago  |  Categories: BDSM, Shemales  |  
856
  |  
60%
  |  1

My first time with a shemale

My First Time
2009, 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 about the idea of a beautiful woman with an amazing, thick cock just pounding the absolute shit out ... Continue»
Posted by izach00 2 days ago  |  Categories: Anal, First Time, Shemales  |  
2328
  |  
100%
  |  1

Shemale Amazon Goddess

This story is based on a dream I had about shemale porn star Meghan Chevalier around 15 years ago.

I'm sitting up in bed. There is an empty glass on the nightstand; I know that I have recently d***k whatever was in the glass. I'm wearing a light violet silk robe, and nothing else. It seems quite feminine. Then I realize that my body has become quite feminine as well. The fat I've been carrying around for years is gone and my waist has tapered down to about 27 inches. My legs are long and slim. My hips are now softly curved with an ass that is far more female than male. My hair is now... Continue»
Posted by Entrapped 2 days ago  |  Categories: Celebrities, Fetish, Shemales  |  
1187
  |  
100%

Misadventures of Karen

Wrote this for someone. Might be a small series, i dunno.

Late in the Winter evening, Karen sat down at her computer searching through her email with a glass of wine as she did almost every night after a long day of work at the office. Strolling through her emails Karen noticed a peculiar one from a coworker titled "Busted!". Karen was curious and opened the email to find picture after picture of her dressed up in super revealing women's clothes and exposing her ass for the world to see. Normally this would be no problem, but you see Karen, the protaganist of this peculiar tale, was born ... Continue»
Posted by ConvertedGirl914 2 days ago  |  Categories: Shemales  |  
1390
  |  
100%

TRANSVESTITES NOT s****rS VS ZOMBIE APOCALYPSE Ep5

All characters are over 18

Béa was sexy femboy when she found a wild runaway boy. She raised him and together raised their feminine side to grow up as s****rs into beautiful transvestites girls. Discovering each others body and transforming together they soon became lovers, living perfect girl life together until zombies attack the city. The girls discovered that people could be cured by having sex. Girls were on their way to inform the news star announcer Jim J.J Johns that zombies can be saved when Lilly was turned into zombie and had sex with a zombie girl that delivered a weird tentacle... Continue»
Posted by Baachan 2 days ago  |  Categories: Anal, Group Sex, Shemales  |  
471
  |  
100%
  |  2

The Ultimate Humiliation and Entrapment of a Sissy

In the dingy motel room where my life turned around in such a short time is where this story begins but the beginnings of this story were many years in the past, a past in which dressing up, spanking, bondage, cocksucking, public outings and humiliation had occurred in bits and pieces. I was not so much a real submissive as much as someone who felt like it was edgy to see how far I could come to the precipice of my fantasies that aroused me so much without becoming trapped by them. In the end I hoped I would become trapped and feel all that goes with being stuck living such unusual fantasies... Continue»
Posted by dorisTVmaid 3 days ago  |  Categories: BDSM, Fetish, Shemales  |  
1390
  |  
100%
  |  1

Indian sissy maid: Wife Returns

the night while pressing aunty feet, she told me how girly i become, she wished she could have Wife like me. She told that village life is harder ,as she has to woke up early ,do all the house ,dairy and farm work, she get little sl**p.next time ,she planned to take her with me as her sissy maid.Doing all the chores,entertaining her and her guests. she already planned to retire ,she planned to purchase a young boy for 20 lakhs, make her as Hijra(live in sissy maid) slave.Whole village knows about it.Even my wife too.
Mother in law slowly fall asl**p, i put her legs from my lap on bed ,covered... Continue»
Posted by tanyakrish 3 days ago  |  Categories: Fetish, Shemales  |  
841
  |  
50%

Cross Dressing Cock Slut Party

Sadly this wonderful story is just a fantasy, but who wants to make something similar a reality!?!

The evening had taken a while to arrange, but had finally arrived. All 5 guests turned up within 15 minutes of each other and as they did, I fixed them a quick drink and showed them into the living room to get to know each other. Alan was a suited businessman in his mid thirties. Dave and Brian were dressed casually in jeans and Tshirts and both in their mid forties. Jeff and Keith were my age, early fifties and dressed in a shirt and smart trousers. We looked like a bunch of golfing mates who... Continue»
Posted by sissydonna 4 days ago  |  Categories: Anal, Group Sex, Shemales  |  
1354
  |  
100%

My new assistant - her story, part 2

The next week the office renovations were finished and I started working for Mr. Anderson full time as his assistant. It was a busy week since the office was closed for renovations the week before. I dressed carefully for work every day: makeup, dress, panties, bra (lightly padded), skirt, stockings, and low heels. Although I was born male, I pass easily. I am 5'6” tall, 135 lbs, with a small frame and a small face so I was never masculine. I've been female all my life in my mind; with a little makeup and a little estrogen, no one is the wiser. I plan to keep my penis – it has been a source of... Continue»
Posted by MassMan669 4 days ago  |  Categories: Fetish, First Time, Shemales  |  
1484
  |  
100%

FLOWERS AND STEMS

She set herself next to me on the couch in the lobby of the hotel I was staying. I was in a lousy mood and everything to lift me up was welcome. I had noticed that elegant strut that only Asian women have and the short summer cotton skirt that made her look younger than she was. Mid thirties, straight short black hair, her white shirt showing a promising decolleté.
"Do you like women?" she asked looking straight ahead.
I nodded.
'Do you like men too?"
Äre you a professional?" I asked.
'No, I am in heat." She replied off-handedly.
We hadn't looked at eachother and I felt she wanted to kee... Continue»
Posted by FetishFreddie 4 days ago  |  Categories: Masturbation, Shemales, Voyeur  |  
1064
  |  
86%
  |  2

SHEER PLEASURE AT CHATEAU FEMME 2.

SINDY & PENNY’S PLAYTIME
INTIMATE SHEER NYLON TRANSVESTITE PLEASURE

For an hour Sindy and I posed for Susie around the house trying to look as glamorous and feminine as possible. She took pictures of each of us individually and together and all the time there was an air of sexual tension. With every movement, I could feel the taught straps of my feminine lingerie tugging against my smooth body and my legs felt so arousing whispering together in wrinkly nylons. Soon Susie could tell that perhaps we were ready for some fun so eventually we made our way back into the dressing up room. Her... Continue»
Posted by SheerNylonPenny 5 days ago  |  Categories: Anal, Fetish, Shemales  |  
558
  |  
100%
  |  2

My new life as a brainless d**g house whore

Look I am not like your typical gurl. I am well educated from a good home and I have a great practice. I am clean disease free and always smell nice. I have always been a sex addict since I was little. As I got older my tastes got kinkier and kinkier. I have now been a submissive since my teen years and I just came to the extreme side of that. It all started a year ago when I started seeing a new mistress. She was into feminization so she started dressing me. I liked it ok as she would use dildos on me but what I really liked was being called names and made to go out in public. I found I liked... Continue»
Posted by dncn31 5 days ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
2321
  |  
100%
  |  1

Rebirth

I knew I should have checked the long range weather before I left the
airport. I had been airborne for several hours and the weather was rapidly
getting foul. November weather can be very tricky in this area and can change
quickly...warm one hour and cold the next. It was snowing heavily now, I was
hitting strong, gusty headwinds, and I wasn't exactly sure I knew where I
was. I estimated I had about an hour's worth of fuel left in my single engine
Cessna 172. Unable to make radio contact with anybody, I really felt alone in
this unfamiliar white world. For the first time, I felt a stran... Continue»
Posted by lana100 7 days ago  |  Categories: Shemales, Fetish  |  
3383
  |  
93%
  |  2

My hot dreams

bad english, sorry ) (online-translating)

My girlfriend
tattooed slut with piercing, which substitutes his holes for any cock and loves to lick her girlfriends. She takes on five men at a time, and then smears their cum all over my body. She wears the engagement ring your hubby-Sissi as the piercing of the clitoris and is not taken out of the ass anal plug. Every year it is fucking at the wedding directly to the wedding dress, and she's masturbating on this video all year.
But most of all I love to see my bitch fuck Threesome in front of me, while her mistress Fucks with a strap-on up my... Continue»
Posted by LexDong 7 days ago  |  Categories: Taboo, Shemales, Fetish  |  
1243
  |  
50%

wedding breakfast

Hi all. This tale of mine is 100% true and happened 5 or so years ago.

I'd been invited to a wedding at some stately home in Essex. One of my old uni pals was getting hitched to his long term girlfriend. As was the norm with these occasions I left booking a hotel till the last minute so ended up in a travelodge or it could have been a premier In rather than the plush hotel where everyone else was staying. It was just off the a120 nr Braintree opposite a retail park so could be good for some hotel fun I thought.
The day of the wedding I drove up checked in and threw my bag of Clara clothe... Continue»
Posted by claracduk 8 days ago  |  Categories: Anal, Fetish, Shemales  |  
3682
  |  
100%
  |  2

The unexpected awakening

This was an era in which sexual fulfilment and experimentation was the norm. It wasn't uncommon for people to host parties at their homes. Nearly every single sexual experiment one could imagine would take place at these parties, legally of course. It was a great time to be alive.

And this mark Dave's first time going to one of these parties. Dave wasn't a strapping man, he wasn't a man who's body was that of a greek god. He stood six foot one, thin body frame and thin arms, and viewed the world through his glasses. He could feel his nerves shaking his body as he made his way through the r... Continue»
Posted by pornfan1976 8 days ago  |  Categories: Anal, First Time, Shemales  |  
1861
  |  
100%
  |  1

My First Visit to the Adult Book Store (part 1)

My First Visit to the Adult Book Store

After I checked out the Store and Bought that Big Beautiful Cock I went into the booths put some money in the machine (these are more like rooms then a booth you could get about ten people in there) and took off my street clothes to reveal my Pink Mini Thigh Highs Black & Pink Pantys Black Bra small fake Boobs & Chastity Cage and sat down to watch and rub my Sissy Clitty about ten minute the door opened I forgot to lock it and a guy walks in looks at me and says Nice do you mind if I stay?
I said ok, he put more money in the machine and sat down and ... Continue»
Posted by Bi_Norfolk_cd 9 days ago  |  Categories: Anal, First Time, Shemales  |  
3174
  |  
91%
  |  4