Shemales Porn Stories
Page 65

Clara Bow's Academy For Would-Be Ladies: Part

Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his anus tingled and gripped the soft rubber plug she’d also chosen for his first day. His stepmother had allowed his soft ginger hair to grow to shoulder length already, and his dosage of hormones had been already been increased. He had been suitably attired in a gingham dress with pink socks and red... Continue»
Posted by midsummerman 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 969  |  
98%
  |  6

Cross dressed slavery

Oh just try it on, don’t act so…stereotypical.”

I started to protest again, I mean I was not trying to be a jerk, but I did not feel like serving as Leena’s dress dummy all afternoon. I felt uncomfortable enough around her and her clothes. The way she dressed made me crazy and I knew she would tease me all afternoon if I let her. It was my own fault really, I approached her at her last ‘fashion show’ and offered to take some pictures. I really did like her designs, but mostly because of my own peculiar fetishes. Leena worked a lot with sweaters and wool, knit creations she called them, ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1664  |  
98%
  |  12

Trip to LA

I was out in Los Angeles on business and as I would dress up every nite and see if there was anyone who wanted to play a bit. On Friday around 5 pm I decided to go all out and I dressed in a corset with garters, panties, bra, stockings, red heels and a black lace cocktail dress. I finished it off with a blond curly wig and some rhinestone earrings. I had taken my time with my makeup so I looked pretty hot.
I had some conversations with Tom during the week but they always ended up with just talk so I figured Friday’s conversation would be the same. I was chatting with a few guys as well and... Continue»
Posted by MichelleSEmass 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1295  |  
98%
  |  6

first time meeting with another CD

I was online and a message popped up from another Cd who lived local. He was married just like me and loved dressing up. We chatted for a few days and then he asked me over to his place as his wife was working. I had a few hours spare so i packed a few things and went over to see him.
when i turned up he was ready dressed and waiting, So as soon as i was in there i stripped and dressed up and aplied my make up. We admired each other for a while and donme all his house work between us.
We got close and looked into each others eys and then we just kissed. It was wierd at first but so nice.We ... Continue»
Posted by xdrespauline 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1063  |  
98%
  |  12

caught cross dressed part 2

"As Pippa is now completely unable to move her head... I think that we should begin with her eyebrows." Alice told the others.

The others each nodded their consent, and Alice began her work on me. My already thinned eyebrows were plucked pencil thin, and were shaped into a high arch over my eyes. Once this had been completed, Alice tattooed over them, making them a permanent feature of my face!

The tattoo gun still in hand, Alice began working to give me my permanent 'eye-liner' ...by blackening the areas around my eyes with a solid line of black ink. Long, thick, 'long-lasting' lashes ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1778  |  
98%
  |  7

strap on gang bang....

Well hello boi's and gurl's,
Just had a evening of bliss and really wanted to tell the world...
I am tall, slim, sexy CD. Have been X dressing now for over a year.
Never new it but after attending a Halloween Wedding as a female I
was hooked...

I have had sexual experience with male's and couple's in my past,
and am very kinky too...
I also tend to be more submissive when dressed up.
Love to please others before myself type...

So I had set up a meeting with a very nice member of the military and
his wife.He was bi BBC, She was white and very dominant. Both where very sexy, and ... Continue»
Posted by dawncd1 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 993  |  
98%
  |  4

Stephon fucks Sora and her sexy ass tranny ass

Ya know what fuck it since my last story wasn't good apparently imma just cut the bull and tell the whole story now shit.

So my dick is in her ass and im in heaven, like on some cloud nine shit.the head board is knocking she screamming, im not sure how loud though cause im pretty focused.And like i said before she released the dragon or sme shit like that i mean, what she did quite literally was with me inside her flip her whole body so she is now all fours and im like... the fuck did i get myself into. but still i don't punk out. the she told me to go deeper. Alright how hard can that be. ... Continue»
Posted by cooler34 2 years ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 1061  |  
98%

markie dunlap Kansas city sissy for all black Mast

I am a Sissy Faggot! I have been programed by hypnosis to write (beg) to be owned and femenized by a black Master in Kansas City Mo. For months I have watched repetedly sissy hypnoses videos and black cock worship videos. My girl freind set it all in play when she found me dressed in her panties bra and stockings. She has comanded me to tell all who read this that the phrase (black cock sissy) will in fact make me your sissy cock slave to dress me and use me as you wish. She has also instruced me to make it more intresting and let you know I live in Lees Summit and that Since I will not rememb... Continue»
Posted by markie2269 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1152  |  
98%
  |  6

Rubber Ball

Hi All,

This is my first ever real attempt at writting a story to post. It is ALL fiction, and most of it is just made up and what I think it would be like but never experianced. I was inspired to write this after looking at some pics from a friend. I have an overactive imagination which is probably much better in my head than on paper. I suppose I should have proof read it, but I'm assuming I'll probabl be the only person to read it. Please have mercy when commenting... if anyone reads this at all.


I scurry up the sidewalk quickly, thankfull that its night and no one seems to see me ... Continue»
Posted by GreyMan44 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1262  |  
98%
  |  7

jobsite surprise

The other afternoon I went to deliver an estimate for a large gardening job I had been working on. When I arrived at the house I rang the bell and waited. There were two cars in the driveway but no answer at the door, so I walked around the back to the pool. As I came around the corner to the large hedgerow separating the back yard from the pool I heard two female voices talking and giggling. Passing the hedge, I froze dead in my tracks. My eyes flew open wide and my jaw dropped at what I saw.
Beside the pool, the lady of the house was making out with one of the most beautiful women I had eve... Continue»
Posted by leadpencil21 2 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  Views: 2128  |  
98%
  |  3

Unique Misadventure

I always felt I was one to walk in a path of two worlds. both parallel and at at times, they cross and go there seperate ways within me. it can be stronger then others, but in all cases.... I always felt feminine by nature, lacking a dominate soul I suppose. it felt more natural, and in luck or fate; people referred to be by 'mame' or 'miss' then as a guy. it would be considered a insult, but deep inside... it made my smile silently.

my misadventure starts on a nice autumn evening at the beach. partly to enjoy the breeze, and otherwise just to be in a quiet place. I would watch the fis... Continue»
Posted by QuietSoul 3 years ago  |  Categories: Anal, Sex Humor, Shemales  |  Views: 450  |  
98%
  |  6

my transformation

is fiction


It is strange where one’s desires can lead one. Take me as an example. Always entirely enamored of, infatuated with and completely submissive to all things feminine, a true devotee of Female Supremacy, my lifelong fantasy has always, since before I can remember, been to find a position as the submissive sissy maid and sex slave of a commandingly beautiful, dominant Goddess, spending virtually all of my time that was not devoted to domestic duties with my sissy face, mouth, and tongue smothered by and buried in the delicate, sweet, pungent pussy and ass of my Owner/Mistress and/... Continue»
Posted by elisatv 4 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 934  |  
98%
  |  6

The Hotel Part 1

I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days.
Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, f***ed fem, huge dildos, and giant buttplugs are just a few of my fetishes, and I expected every fantasy to be fulfilled this week.
As I pulled up under the awning of the front enterance I was met by a woman in a French Maid uniform. I introduced myself, and said I was checking in fo rthe week. She smiled, as she opened my car door, helped me out of the car, took my ba... Continue»
Posted by NJStraponLover 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1321  |  
98%
  |  8

Caught cross dressed part 1

My name is Philip. I am married to a beautiful woman called Helen, and a few days ago... I did something very stupid!

My wife, her mother, her beautician, my P.A. from work, and any of their friends, (in fact, anyone that they choose,) are now completely in control of my life. They are my Mistresses, and I am fully subservient to their every desire. In fact, I am now nothing more than their sex-slave!

Recently, whilst I thought that my wife was visiting her mother, and would not be back all weekend, I decided to indulge myself.

I resolved to use the time to pamper myself, and to pan... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2914  |  
98%
  |  8

Bi male and anal sex

Thru out my adult sex life I have always enjoyed having my ass teased and played with. 
Then I started dating a woman whom loved to tease a mans ass with her fingers, yes fingers where she quickly got me use to taking 2 of her fingers. 
Then one night things changed. After a hot night of wild sex, she slowed things down before excusing herself. But before she left, she rolls me over on my chest, which to me means she want to tease my ass. I hear her in the bathroom , toilet flushes and I hear her returning to the bed, straddling my legs, she racks her fingers up and down my back before she l... Continue»
Posted by rogue-1966 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3679  |  
98%
  |  19

My journey into hedonistic crossdresing, Part 1

Part 1 deals with events that had transpired which lead to my first sexual encounter with a man, and ultimately, my first relationship as Elaine. Almost impossible to believe, and the thought of Vince, even today, still makes me yearn for those wondeful days! The ending is where you'll find the sex part, if you need to jump ahead!

At 6 months shy of my 19th birthday, I had just discovered that I wasn't the only "whack job" on the planet! Before the internet and broader social acceptance, it was pretty hard to be a crossdresser, transvestite, drag queen, etc...especially being fr... Continue»
Posted by elainetgrl 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 617  |  
98%
  |  14

Fresh Pussy and a Shemale cock!

We all meet people who turn us on, and make our cocks hard or pussies wet, and i was lucky enough to meet a hot straight girl at a party awhile ago. we really hit it off, and i asked her if she wanted sex, and she said yes, but only a hard cock... I had to tell her that i was a shemale with a 7 inch thick cock and would love to fuck her and eat her sweet pussy. She did not seem shocked, but said show me, so we went upstairs to the host's bedroom, and i pulled out my cock and bam, she did not waste any time, getting on her knees and began to suck my cock. I quickly got naked as did she, she had... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 1474  |  
98%
  |  6

Shemale massage

It has been one of those long and stressful weeks. I’m in desperate need of relaxation and relief so I head over to an Asian massage parlor for a typical happy ending massage.
The girl who usually massages me isn’t available so another girl is suggested which I accept. I think to myself that she can’t be much different than my usual so I don’t care much. I just need a massage badly.
She comes out of the back from another massage and introduces herself as Jessica. I smirk a bit knowing there is no way her name is Jessica but I go with the bit and am happy as she is quite attractive and alread... Continue»
Posted by malesub01 1 year ago  |  Categories: Shemales  |  Views: 7607  |  
98%
  |  12

Breakdown!

Break Down


It could have been a perfect evening.


Earlier, I had taken a long, luxurious bath and gotten myself completely smooth and silky. I spent 45 minutes on my nails, painting them a robust “Romantic Red” with luscious lips to match. A black and white polka-dot bra and panty set came next and then I rolled on a pair of silky, sheer stockings that made my legs look like they went all the way up to heaven. I slipped into a beautiful sheer bodice black velour cocktail dress that flaired (well) above my knees, and then strapped into a pair of black patent leather pumps with criss-cr... Continue»
Posted by 1kara 2 years ago  |  Categories: Shemales  |  Views: 1010  |  
98%
  |  14

Lucky Afternoon Part 5

The day finally arrived whe I absolutely had to get my boat out of the water and fortunately it was a slow day at work so I asked a couple of my employees if they wanted to assist me? They eagerly agreed because they would still be on the clock and it was a very nice day. I had them drive one of my company trucks and I took my own truck and told them to meet me at the boat dock. I decided to stop and pick up some beer and ice and figured we could run around the lake for a few times to use up some of the fuel before it was parked for the winter.

I hadn't talked to Nikki for a couple of da... Continue»
Posted by rcpeters 4 years ago  |  Categories: First Time, Shemales  |  Views: 284  |  
98%
  |  2