Shemales Porn Stories
Page 77

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 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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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 4 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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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  |  
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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 3 years ago  |  Categories: Anal, Fetish, Shemales  |  
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my mom turned me into her sissy




"Mom! I called out as I got home from baseball practice, "I'm home!"

"Hello Danny, we have to talk," she responded, while exiting my room.

When I saw what was in her hands, I became nervous. Some of the guys I pal around with talked me into shoplifting a few things from a department store.

"Please explain where these items came from."

I should have told her I was sorry, and that it was just the one time,

But instead I said, "Tommy made me do it. He said it was a dare. I didn't want him to think I was a sissy."

The next thing I knew, I was in big, big trouble with Mom. I... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Fetish, Shemales  |  
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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 3 years ago  |  Categories: First Time, Hardcore, Shemales  |  
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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 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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The Pre-Nup Agreement (a Chrissie Conway Story)

The Pre-Nup Agreement


Several years ago one of Kellys' friends had a b*****r who was getting married in Reno and a bunch of us girls
decided we would all get together for a wild weekend reunion. I unfortunately had several of my regular clients to see
on Thursday and Friday afternoon and wouldn't be able to depart for Reno until early Friday evening. Needless to say by
the time I arrived the ladies were already in a crazy celebratory mood. I'd had several drinks on the flight so I wasn't entirely
unprepared once I got to Reno.
I had the valet hire me a taxi and headed for the Cal... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Sex Humor, Shemales  |  
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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  |  
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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 4 years ago  |  Categories: Shemales  |  
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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  |  
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My CD / Sissy story and 1st meet humiliation

I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before talking about the meet up, skip the first few paragraphs to get to that bit.

I have always known I love girls clothes, lingerie, miniskirts, colourful sheer blouses , anything satin or lace, since a very young age. When I was 18, I finally had a credit card, and bought my own lingerie. I bought clot... Continue»
Posted by indoblu 8 months ago  |  Categories: BDSM, First Time, Shemales  |  
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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  |  
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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  |  
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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  |  
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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  |  
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Part 1.. An Idea forms

My plan was pretty simple really… Find a fem-boi looking for a Sugar Daddy and change him to a her over a period of time… Simple in theory, Much harder then it would seem in reality. Being in my mid-40’s and rather well off from a few investments and a wealthy grand-mother I had plenty of time to indulge my more twisted desires. I got into Trans-Sexual porn a few years ago and I was hooked almost immediately. I do not think I am actually gay because the thought of ass fucking a man does nothing for me.. But on the other hand if that man had very feminine features, a small quiet voice, creamy ... Continue»
Posted by Azmodaz 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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Gloryhole Gurl Part 1

Making of a Gloryhole Gurl! Part 1
By Kristy

Just Like in any marriage after fifteen years ours was getting pretty routine. Every three months I could have sex, in the missionary position, with her wearing flannel Pj’s. Even in the summer she would wear long pants type pajamas and when I would buy her something sexy she would just say it’s not my type and never even try it on! It was only six months after our marriage that she told me she doesn’t like to have oral sex!
Well like any red-bl**ded male I started hitting to gentleman’s clubs around town. The sight of t... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  
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HOW I BECAME A TRANNY WHORE (PART 2)

HOW I BECAME A TRANNY WHORE (PART TWO)
After my first night working for Mama T, I was hooked. At least once a week I was a worthless whore at her trailer. I would be at her trailer, ready to serve her cliental. Of course most the Johns picked one of the real girls over me, but there were the occasional guys that wanted some thing different or couldn’t wait. I didn’t mind. I just craved being in this sleazy environment knowing I was nothing more than a piece of useless meat on sale. After all I was tainted merchandise; I had a cock between my legs instead of a juicy cunt. The other gir... Continue»
Posted by littleoralvee 3 years ago  |  Categories: Shemales  |  
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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  |  
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