Shemales Porn Stories
Page 59

Clare


I shouldn't have tested her. Or, maybe I should have. I'm not sure anymore. I'm not sure which emotions are mine. I'm in a happy relationship. I think. My name is Clare. Now... Anyway. Sorry, I realize how confusing this is. Let me attempt to make sense out of it. My name is John. Or, my name used to be John. My best friend is named Hunter. We did everything together. Now we do everything to each other. You see, Clare was dating Hunter. I didn't know her last name, whether or not she had a f****y, or anything like that. The strange thing is, neither did Hunter. He assumed she was shy or emba... Continue»
Posted by klammer 4 months ago  |  Categories: Fetish, First Time, Shemales  |  
1791
  |  
100%

Irresistible



Irresistible



My wedding day... I suppose all brides cry on the day of their wedding. But maybe not for the same reason my bride was crying...

---------------------------------------------------------

Becca and I had been engaged for nearly a year. Being that we both came from prominent families we had a huge wedding planned. All of New York society would be in attendance. Her father tried not to show it but he was incredibly perturbed at how much he had to shell out for this huge wedding.

"I don't know where this stupid tradition of the father paying for the wedding ca... Continue»
Posted by klammer 4 months ago  |  Categories: BDSM, Fetish, Shemales  |  
3198
  |  
100%
  |  2

Thougt i could fool the staff

Realized this day would go on so decided to go buy lightbeers an two packs of ciggarettes..

Uppon arival i smoothly asked two female store attendants where i could find makeup.. yeah sure over here, they where holding back giggles i swear and as suave as james bond i just flat out lied someone is gonna look really pretty for his birthday! (u know im just getting supplies) then i asked them about what i thoght was foundation and they wher like yeah u use it to blabla and i said yeah just wanna make sure i got this note with me im not al so sure of what everything is...
So far so good..
... Continue»
Posted by tinyswede 4 months ago  |  Categories: Sex Humor, Shemales, Taboo  |  
2117
  |  
100%

Bi MMF, FemDom, Cross Dressing, Cuckold

I have these friends, a husband and wife. For the longest time, I've wanted badly to have sex with both of them. First I wanted just him, but I thought it would be even better if I involved both of them.

I'm bi, but they don't know that. Anyway, after years of hanging out with them, I see how domineering she is over her husband - my friend. She really puts him down, bitches at him constantly and belittles him, in front of anybody. She's really tough, but she's mostly been nice to me. She's got a couple of extra pounds and she's pretty and blonde. My friend is not very handsome, more "pretty... Continue»
Posted by chrissylegs 4 months ago  |  Categories: Anal, Gay Male, Shemales  |  
2271
  |  
100%
  |  3

Brandi Cums After MNF

This guy calls the e****t services and it seems like he is going to have the best sex in his life…

So, I come home from watching Monday Night Football with some guys at the local pub. I turn on the TV and some infomercial for an exercise machine comes on. The model working the machine has a great body and seeing her workout is really working me up. My cock even gets a bit hard.

Feeling a bit on the adventurous side, I open the phonebook and look for an e****t service that has shemales. I find one. Just talking to the dispatcher and describing what I want makes my cock hard again.

The ... Continue»
Posted by princessamyov 4 months ago  |  Categories: Anal, Fetish, Shemales  |  
599
  |  
100%

Shock and Awe Part 2

Have you ever been with a shemale before? This guy experienced what it’s like to be ass-fucked by a half-man, half-woman and it seems that he really enjoyed it…


Carla lay back on the white sheets and said ‘I want you to lick me down there first’

I was a bit shocked to be honest. I mean every guy imagines what it must be like to suck a cock at some point in their lives (and I just had for the first time, it was lovely), but anus licking had never entered my mind and I was hesitant.

Carla noticed my reticence and sat upright again. ‘Let me show you’ she said ‘ turn round and bend over... Continue»
Posted by princessamyov 4 months ago  |  Categories: Anal, Fetish, Shemales  |  
678
  |  
100%
  |  1

Shock and Awe

This guy goes on a business trip and makes one of his long dreams cum true…

My name is Frank and I’m a decent looking Irishman in my mid 40′s. Every now and then my work takes me to London for a few days and I like to let my hair down if I can. I try and find a hotel in the Earls Court area so if the mood takes me I can visit one of the many hookers that has apartments in the area and advertise their services in local phone boxes.

Last month was one such occasion and I checked into a hotel I had booked at random on the Internet. It was a small place but comfortable and my room was ‘theme... Continue»
Posted by princessamyov 4 months ago  |  Categories: Anal, Fetish, Shemales  |  
1145
  |  
100%
  |  1

beautiful tranny

This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong?

Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s not that I should worry about! Men of my f****y have always been stocky, and thickset. So a big nose and stocky figure are not a trouble! I’m working in a Western City College as a tutor of English Literature. I teach student best masterpieces of Shakespeare and Charles Dickens, and so I am in my whole best! I ... Continue»
Posted by princessamyov 4 months ago  |  Categories: Anal, Shemales, Taboo  |  
4415
  |  
100%
  |  1

Becoming My Girlfriend





"UUNNNNNGGG...." Bernard moaned as he speared the soft, wet mound of
his girlfriend, Allison. "OOOOOH!" she cried as she was mounted, and
wrapped her supple, pale thighs around his hips, her legs scissoring
behind him to pull him even deeper into her slick canal.

Bernard was in heaven as he started thrusting hard into Allison,
savoring the pleasure of her soft, curvy body. He found it odd that
she was so willing to have sex now, when their relationship was on the
rocks, but he had waited so long for a chance to ream her that he
wasn't going to complain.

"Oh! Oh! Oh!" she... Continue»
Posted by lana100 4 months ago  |  Categories: Shemales  |  
3422
  |  
100%
  |  2

Bondaged and fucked at a hospital: Pt 2

I ate my lunch watching tv, when I was done Lisa cleaned up after me and she gave me some time to rest as she left the room, sort of like "nap time" at a daycare. I was about to drift off when I felt a sudden strong urge to pee but as I moved my legs around in the bed to get up I was instantly reminded of the thick crinkly diaper I had on under my hospital gown. I thought about what the nurse said, about having to use diapers for a whole week and I didn't want to disobey her orders seeing as she really knows how to discipline a "naughty diaper boy" which is what she referred to me as. I also d... Continue»
Posted by adblman 4 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
1486
  |  
100%

End of the Week

Ernest Gaines, known by most as ‘E’ or ‘Big’, bounded down the corridors of Presbyterian Regional Medical Center wheeling a patient towards discharge. It was shortly before 8:00 a.m. on Saturday which meant this was his final task of his shift. He made it to the waiting area and brought the chair to a stop as the elderly man peered out the window for his f****y.

“What’s going on,” a fellow orderly asked.
“Can’t call it,” E replied.
“I hear ya, man. You gettin’ off soon?”
“Yeah. Goin’ to the crib and chill. Got three in a row off.”
“I’d do that. But I got too many people at home to get a... Continue»
Posted by faggyboi 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  
1533
  |  
100%
  |  2

Horse Cock Girl part 4



It had been nearly a year since Amy, Lucy and Scarlet had begun living together for their college studies. In that time, they'd all grown closer together. They effectively had a secret, three-way relationship going.

Amy had, the year before, grown the large cock of a horse by a freak accident at a lab on a field trip with college. She had told her best friend and classmate, Lucy, who had immediately started thinking of uses for it. It had scared Amy, at firsts, but soon after they started, she was enjoying their lesbian relationship.

They'd opened the spare room in the flat. Lucy had... Continue»
Posted by drew1207 4 months ago  |  Categories: Anal, Fetish, Shemales  |  
1608
  |  
100%
  |  1

Horse Cock Girl Part 5

Author's note:

I got a fair bit of feedback on Chapter 5, stating that the chapter were too short and that the description had been lacking.

I know this will end up being under a page on here, but it is the second-longest chapter yet. I hope you all enjoy the work I put into it.

It's not been easy to keep this story going for so long, so I think I'll likely only write one or two more chapters to wrap it up. I'm not sure how it'll end, so please, don't ask me.

Once again, thanks you too everyone that reads the story. I hope you enjoy it and I welcome constructive feedback.

***
... Continue»
Posted by drew1207 4 months ago  |  Categories: Fetish, First Time, Shemales  |  
1668
  |  
100%
  |  1

How Kenny got his promotion.

For the last 15 years I have been working in the same boring office and as a result I have actually worked my way up to quite a high up position, my own parking space, my own office, all of those benefits you get, and as part of my job I am responsible for and have to support the work experience fellows we have that do general admin duties and sorting out mail, there's very rarely any complications.

One day I'm just finishing up some paperwork and can't wait to get home as I have a nice a lovely bit of pulled pork steaming away in the house, when all of a sudden a work experience boy comes ... Continue»
Posted by wherethewhitewomenat 4 months ago  |  Categories: Anal, Gay Male, Shemales  |  
34233
  |  
100%
  |  5

"When I became a girl...": Part 2

...We stayed up talking about my revealed secret and Peter was very curious to hear about all the small details. I told him that when we first met, as our moms talked to each other, I was shocked to hear his mom refer to me as a little girl and instead of correcting the honest mistake, my mom just accepted it. I continued by saying, "Yea... Well, from then on I was made to wear girl clothes, play with girl toys and even act like a girl, which I thought was fun anyways. My mom even encouraged me to start potty training by sitting on the toilet like a girl and I would wear the pink girl pull ups... Continue»
Posted by adblman 4 months ago  |  Categories: Gay Male, Shemales, Voyeur  |  
4441
  |  
100%
  |  4

my HEAVAN

This dream is for my super sex goddess mistress HEAVAN123 i worship the ground on wich she toers over me on ,i kneel at her feet waiting for her permission to show me wild devotion to her super temple of lust.
This is for you my goddess---

I am your son in this dream i am a short young man of only about four feet six inches tall,You being my mother on the other hand are a towering stacked wonder of nature standing a full eight feet tall your bust thrust out huge like two massive beach balls thrusting against any clothing you wear stretching your dress so tight they would swing & sway heavi... Continue»
Posted by huge_cock_rules 4 months ago  |  Categories: Fetish, Shemales, Taboo  |  
1517
  |  
100%
  |  2

Playtime Stories Ch 1.

1.

I am such a slut.
I was soft a few minutes ago after cumming hard, but now as I drive to my motel I’m getting hard again. I keep pulling my cock out of the side of my panties and rubbing the sticky head as I remember the man behind me gripping my hips and pumping my ass. Precum lubes my thumb work. My ass is a little sore and leaking lube after a hot slow fuck from an older Hispanic man who was a little too gentlemanly and a bit too small for my tastes. I fixed my makeup but I should have done a better job with my thick auburn wig. Although I just came and I got fucked like I w... Continue»
Posted by 6988slutty_rbckyy 4 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
1518
  |  
100%
  |  3

Playtime Stories Ch 2

2.

My cock is so hard as I write this. Occasionally, one hand strokes while the other types.
Most guys love a good blowjob. Most guys are afraid to try a finger in the ass, but love it after they do. Most guys want a woman to be a total wanton slut or act like the nastiest whore of their wildest dreams. Most women aren’t loose enough to be that “hot” or that incredible of an experience.
I picture myself as everything I wish I could find in a slutty bitch. You know, a total nympho who really will do anything and then ask for seconds.
Before I tell you about what happened th... Continue»
Posted by 6988slutty_rbckyy 4 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
1402
  |  
100%
  |  1

Playtime Stories Ch 3

3.

As I left the booth I was in heat. But first I needed to pay a visit to the rest room and finish my browsing, so I replaced myself wet and adjusted my clothes. I thanked him again and he thanked me and then complimented me on being hot. He closed the door and locked it behind me.
I turned right and followed the maze of booths to the restroom. I went inside and locked the door, remembering that night years ago when I had been all but f***ed to suck off a really big nasty guy who “made me.” It wasn’t cool at the time but it was a source of stimulation and fantasy ever since. On ... Continue»
Posted by 6988slutty_rbckyy 4 months ago  |  Categories: Anal, Group Sex, Shemales  |  
934
  |  
100%
  |  3

A recent date.

Normally I don't use Craigslist because of the fakes, flakes and phonies but this guys add caught my eye and his pics did as well. I wrote him and we set a date for the following evening at 8:00pm sharp. I gave him the directions to my apartment and told him that I would be expecting him. I added a pic of the outfit that I would be wearing as a tease and to fuel his imagination. The next afternoon I started to prepare for the evening's activities. I shaved my face smooth to remove any stubble and then drew a hot bath with lightly scented oils. I shaved my legs smooth, paying extra attent... Continue»
Posted by nickelwound 4 months ago  |  Categories: Anal, Gay Male, Shemales  |  
2730
  |  
100%
  |  1