Shemales Porn Stories

Pirate Erotica Chapter 2

The captains cabin is well-supplied with moaning, cross-eyed wantons, either masturbating, or having rabid sex in a delirium of excitement. A complete lack of law, an atmosphere of indecency pervade here. The captain’s will is the only truth, and all the crew know how to please and displease him. The captain, I must now mention, has hooks for hands, and pegs for legs. In addition, he has but one good eye, his bad one lies partly hidden under a tattered, ragged eyepatch. The triangular patch is made from the boiled, shrunken scalp of a former first mate, a mutineer, to whom some of the captain’... Continue»
Posted by buggiebug10 2 days ago  |  Categories: Anal, Hardcore, Shemales  |  
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First meeting with Dom sissy mistress

I was a longtime secret panty sissy who played in private and only dared dream of finally meeting someone face to face when I met Miss Jamie on xhamster. We had an immediate rapport online and before long she suggested meeting. Of course, with her long experience as a sissy, and with me being an obviously natural submissive, she would take the role of teaching me my proper place as a submissive sissy. This is the account of that first meeting.

Miss Jamie's logistics were simple:
I was to park at a nearby shopping center and wait for her.
When she arrived, I was to get in her car.
She wou... Continue»
Posted by Shelleyisasissy 3 days ago  |  Categories: Fetish, First Time, Shemales  |  
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Daddy's Little Slut

Here I am, surfing on my favorite porn site. My dirty little urge has taken hold of me again. After a long period of deniying myself the need to dress up, i relapsed again. I bathed and thought of trimming my pubes a bit, but ended up shaving myself completley again. I tend to do it in my urge to cam and show off my sexy body and after cumming i regret it instantly. It makes my life difficult because i have to hide my hair free body from all my workmates and friends. So here i am, shaved, smelling really good from my favorite gucci scent, wearing my dark hair wig, my sexy stockings and lingeri... Continue»
Posted by ignitron 3 days ago  |  Categories: Fetish, Masturbation, Shemales  |  
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Dragon's Hole Part 2

On the long trek back to the room, something else catches your eye, another sign. This one says Dragon’s Persuasion. Just the name on the sign is enough to pique your curiosity, so you turn and head down this hallway. Unlike all of the other halls that are adorned in medieval decorations, this one has various colors running horizontally down the hall. The colors, you notice, are the colors of the rainbow, but very faint. You wonder what could be down this hallway and continue along until you reach a heavy oak door. You push this door open and right away, you hear moans. Not the same moan... Continue»
Posted by sabre72 3 days ago  |  Categories: BDSM, Fetish, Shemales  |  
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tv sex

4 week I was in a well known high street shop that sells men and ladies clothes..i was looking at jeans I went to try them on in cubicals men to the right ladys to left .as I shut main door it caused a draft and blew a curtain open I see this guy with good size cock in suspenders belt black stockings with his cock and balls on show he was clean shaven.i didn't bother buying any think as all I could think of was his little arse and cock I wanted to fuck him as its been about 14 months since my last had tv sex.i waited out side for him to come out wen he did he was dressed in the black stocking... Continue»
Posted by feormale 3 days ago  |  Categories: Anal, Group Sex, Shemales  |  
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The new "Girl" On the Boat, Part 2

A recap: My career was spent as the Captain of a 100' high-end charter boat in Alaska. I had a crew member leave the boat on an emergency, and my office sent up a new crew member for me. Normally I interview a potential employee before hiring them, but in this case I needed another crew member fast, so he was hired sight unseen by me. His name was Louie, and he was a short, slight of build young man in his 20's. It turned out that he was also a cross dresser, and when a 'woman' her name was Louise.

The first night we had sex was while we were at anchor waiting for a storm to end. Loui... Continue»
Posted by 1kaaboom2 4 days ago  |  Categories: Fetish, Shemales, Taboo  |  
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Following on from the signing of the contract ...

I lay on the table, my erection had disappeared and my limp cock still smeared with maids lipstick lay on my thigh. The restraints were so tight that i was already noticing that my feet and hands were without feeling and i could imagine them biting into my flesh much as they had done with maids when she was strapped onto this same table moments before. I waited looking around me and taking in more of the surroundings, i noticed just how many fixing points were around the room, there were O rings and O bolts screwed or fixed into the walls and ceiling wherever i looked and i could only begin to... Continue»
Posted by oldognewtrix 4 days ago  |  Categories: BDSM, Mature, Shemales  |  
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My Fondest Memory

As my friends here and anyone else who has visited my profile page will tell you I am a frequent visitor to adult book stores that have viewing booths. I will admit up front to being a glory hole slut. At one time I would visit them at least once a day but nowadays not so much. As can be expected I have had my share of both good and bad experiences over the years and today I would like to share one of my best and most memorable.
It was late afternoon when I stopped into my favorite place, Video News and Book on South Main Street in Waterbury Ct. I have been going there now for over 20 year... Continue»
Posted by DeniseTV 9 days ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
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The new "Girl" On the Boat

I have mentioned in previous stories that my career was spent as a Captain of a high end 100' charter yacht working the waters of Alaska. It was a job that provided me many opportunities to 'play' with men, women and couples, most of them older, and all of them very well-off financially.

Passengers and crew had to sign agreements that I could inspect their rooms and belongings for any reason whatsoever, though I assured them it was very unusual for me to do so. For the crew, my main reason for conducting such inspections would be to check for i*****l d**gs.

But another reason for chec... Continue»
Posted by 1kaaboom2 9 days ago  |  Categories: Hardcore, Shemales, Taboo  |  
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Mon nom est Angie [1]

J'ai 18 ans et j'habite dans une petite ville du Vaucluse. Comme tous les adolescents de mon âge je me branlais devant des pornos après les cours ou lorsque mes parents n'étaient pas là. De nature curieux, j'ai voulu savoir ce que ça faisait d’être une femme. Pourquoi? Je pensais que c'était mieux que d’être un homme. Depuis que je me suis mis cette question en tête, j'ai essayer de trouver un moyen de se sentir femme au moins une journée. Le seul moyen que j'ai trouvé était de me travestir, alors je me suis mis en quête de féminité.

Je me suis préparé pour aller a une soirée chez des amis ... Continue»
Posted by AngieTv 9 days ago  |  Categories: Fetish, Masturbation, Shemales  |  
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True Story - about Fucking my Mouth.

We walked into his apartment and he said we can be comfortable here in the living room. He started to remove his pants, so I did also. He was down to his bikini panties and after he took off his shirt, he pulled his panties down and off. He was now nude and I got my first look at his cock. He looked large, long that is and he was cut. I finished removing my shirt and stood there in my garter belt, black stockings and black bikini panties.

He said, “Nice.” I had told him over the phone what I was going to wear.

He sat on one end of the couch and I sat on the other and looked at his... Continue»
Posted by guycd 10 days ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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There Are No Limits, part 2

I didn't see Connie again after the experience, and after a couple of days (okay, a week) of waiting for her to call me (I'd given her my number and explained that I wasn't good at phoning) and realizing she wasn't going to, I returned to normal, that is, Asshole Cop Mode. On May 24th, Martinez came into Wesley Avenue practically singing. Since Sheridan and I were going off shift, I only had the briefest opportunity to ask him what was up. He looked both ways, lowered his voice, and said "Tonio, I met a girl last night that practically blew the roof off my house." Sheridan, overhearing, came b... Continue»
Posted by asphalt3 10 days ago  |  Categories: Anal, Shemales, Taboo  |  
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My Affair With jenny

I met Jenny online after I liked a sexy photo of her while beating off one day and left a comment. Shortly after she sent me a friend request and we begin exchanging hot emails. She was coming to my area and wanted to meet. I was really nervous I had been with my sexy TG girlfriend for 20 years and never cheated but unfortunately we were like some old married couple just fucking every other week and my hard wet cock needed more.

When I got to her room Jenny was even cuter in person than her photos. She had been dressing for a few years and had some mediocre CL encounters and wanted a more... Continue»
Posted by hardonforporn 11 days ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Pirate Erotica

Were are sailing off the West Indies. A pirate flag is spotted. The sailors begin preparing for battle. The captain advises me to go to my cabin, to keep the door locked. I pace. I fret, wondering whether the ship is prepared. Cannons are fired. I hear the sounds of fighting outside. Then there is silence. It’s an agony of waiting. There’s a knock at my door.

Who is it?

I am the only survivor from my ship. My life is spared because of my youth and good looks.

As I’m taken into custody I hear the pirate captain tell his first mate, “Don’t kill this little whelp. He’ll fetch a pretty ... Continue»
Posted by buggiebug10 11 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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Couple Uses Katie

So let me start off by giving you a bit of background here. This is a couple who I have played with a few times. They are really nice and understanding. They even allow me to come over and get all dressed there before we play. And yes they are an interracial couple. With that said.......

I don't know where I was or what I was doing, but I was bored and horny and looking for some fun to occupy my mind. Come to think of it, I'm pretty sure I was just in my house on a typical Saturday afternoon. I put out an online post for BBCs. I'm sure if you know me, then you would understand I... Continue»
Posted by Ivygurl86 11 days ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Chapter 20 Chrissie hears wedding bells

Chapter 20

Chrissie hears wedding bells

It's been six months after I first started working in the brothel with
Kate and mommy and I've made friends with most of the girls who work
there and, more importantly, they are starting to think of me as a she
instead of a he. I think getting castrated was the best thing for me. It
boosted my confidence in my appearance and took away all vestiges of my
manhood. I do have a little penis but I don't think it detracts from my
appearance at all. It is easily hidden in clothes as it lies flat when
pressed against tight knickers. It's just a bare... Continue»
Posted by klammer 12 days ago  |  Categories: BDSM, Fetish, Shemales  |  
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Chapter 16 Chrissie & Kate

Chapter 16
Chrissie & Kate


It was the end of our first day of the working week and mommy and I
sneaked into one of the empty rooms, locked the door and climbed on the
bed. She lewdly spread her legs allowing me to lick her pussy clean,
savouring the scent of her juices and the remnants of the many men who
had been inside her. She let me tease her clit briefly but was too
sensitive to let me carry her to a climax. After I was finished I wiped
my lips with my hand and looked down at my mother's beautiful body.

"I'm leaking like crazy, as usual," I said with an embarrassed laugh.
... Continue»
Posted by klammer 12 days ago  |  Categories: BDSM, Fetish, Shemales  |  
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Chapter 17 Chrissie sees Magic Mike again

Chapter 17
Chrissie sees Magic Mike again


It's difficult making polite conversation with a guy whose wife is quite
obviously getting drilled by someone else in the room directly above but
I've got firsthand experience being cuckolded and it's happened right
before my eyes a few times. Furthermore, the Australian I was sharing a
sofa with had married my mother and any man who did that with his eyes
wide open would know how unlikely it would be that she would remain
faithful. Nevertheless, I did have some sympathy for him. He had, after
all, been in a plane for over 20 hours and tho... Continue»
Posted by klammer 12 days ago  |  Categories: BDSM, Fetish, Shemales  |  
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Chapter 18 Chrissie looks forward to getting debal

Chapter 18
Chrissie looks forward to getting deballed


Kate and I watched the video of Magic Mike in bed later that night or to
be more accurate, Kate watched the video on her laptop while I licked her
well used pussy. I could sense that she was having a hormonal rush at the
same time my careful attention brought her to an orgasm.

It is strange having a relationship with a woman I'll never be able to
have sex with, particularly when sex is her livelihood. I know Kate has
been a hooker for ten years and simple mathematics tells me that she's
had sex with thousands of real men duri... Continue»
Posted by klammer 12 days ago  |  Categories: BDSM, Fetish, Shemales  |  
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Chapter 10 Chrissie licks mommy clean again and ag

Chapter 10
Chrissie licks mommy clean again and again


My mother called out to me as she entered Helen's apartment through the
front door, which I was not allowed to use. I was consigned to the
service entrance at the back of the apartment, as most servants were in
Victorian England. In the 21st century it was rare to have a maid in
London, let alone an indentured sissy maid that, not only waited on her
mistress hand and foot, but worked during the daytime as a t-girl
prostitute for the sole financial benefit of his owner. It was a fate I
was led into over three years ago when my w... Continue»
Posted by klammer 12 days ago  |  Categories: BDSM, Fetish, Shemales  |  
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