Shemales Porn Stories
Page 80

The Martini affair

I was having a drink at the crowbar in Chicago when I noticed her amidst all the gaymen around. After being pissed by all the rude and intrusive men I had found secluded spot at a lonely bar stool by the counter to enjoy my Martini. I was wearing a tight hip hugging jeans and a tanktop to flaunt my navel and stomach.

She came aside me and asked for a wine. "White" I heard her stress to the barman. She looked at my colorful drink and asked "What are you having"? Martini I said quickly running my eyes over her curves. "Pretty hot gurl" I said to myself. But i was in no mod to socialize. The ... Continue»
Posted by socuri 2 years ago  |  Categories: Shemales  |  Views: 771  |  
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tranvestite in trouble part 2

How could i have been so stupid?

Here i was, trapped by a guy twice my size and weight, dressed as a sexy secretary, just as he'd asked me, kneeling on this filthy floor, with his solid 8" cock buried deep in my mouth, gagging me.

Andrew was clearly loving acting out his scenario, with his submissive tranny slut, his eyes were bulging from his head. his hips were pumping, back and forth, litterally fucking my mouth, fucking my face.

i could taste the pre cum oozing from him, so much, i'd had to swallow loads, but i could feel it running down my chin, onto my chest. Still.....he couldn... Continue»
Posted by hornyTVluvr 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 771  |  
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Dating Sites Surprises

I like to chat on dating sites, like to look for people there but i had never moved on an actual date. The farest i had been was a cam chat. I was always afraid of a real date. The stories i had heard about were pretty horrible most of the times.
A few years ago i was relocated to another country due to my work, as a newcomer in a not so liberate place i was always scared not to show my sex orientation. Both the gay one as the crossdressing. My only way out were my dildos and the chat rooms. On a chat room i met a guy who sounded really interesting, after several hours of talkinh we both dec... Continue»
Posted by demetracd 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 770  |  
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The Making of a Sissy - Part Twelve

Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as she pulled her indoors.

“Well, you’ve certainly impressed Mr Roberts, and it’s nice to see you with your clothes on again. We are quite the little harlot now aren’t we? We’ll soon have you back down to earth; I’ve lots of chores for you!” Now it was sandy who was downhearted as she drove away fro... Continue»
Posted by midsummerman 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 773  |  
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The wonderful feeling of a sissy penetration by yo

Nothing like that initial penetration is soo wonderful however there is so much more for me. just knowing that i intend to give myself to him submitting to his Big Hard Man Cock is a turn on. He wants me ready for him so he can show me his love and make me his girl.

The act of preparation, the douching and initial lubing, knowing I'm going be taking a real man cock inside me builds on the sexual emotion and makes me feel so submissive and feminine.

laying there in my nighty and panties and assuming the position he desires, normally face down, pussy up, legs together, wiggling my botto... Continue»
Posted by sissygirl 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 770  |  
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My new feminine compulsion

Until I saw shemale porn on the web back around 1998, crossdressing had never occurred to me. But when I saw those doubly-sexy bodies, with both breasts and a cock, my sexual life really changed. I searched out every shemale porn site I could find, and found myself especially excited by hot shemales sucking a man's hard penis. It just turned me on so much! Over time, I started to see pictures of the men sucking the shemales - oh my god! Once I saw that - those beautiful bodies, the stiff cocks, and the men taking them in their mouths, I knew what I wanted.

It started with buying a tube of ... Continue»
Posted by marlynn 1 year ago  |  Categories: Shemales  |  Views: 772  |  
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Panties For ME

Ok, here's a quick story and true at that. I was away on business one night and surfing for sex on Craigslist. The title of my post was "If I'm so strait then why do I want to get fucked like a girl?" It was a popular post and I got a bunch of replies, and a bunch of men wanted to fuck me. I'd just broken up with a girlfriend and I'd decided I'd finally give in to my urges and try the sissy thing for a few months.

After many advances, I ended up going with someone a little older and little less hot than the others because he had the ingenuity to ask what my fantasy was and actually asked m... Continue»
Posted by rikkk72 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 769  |  
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Trapped and Trained Sissy Ch. 16

Trapped and Trained Ch. 16
I slowly opened my eyes, feeling how heavy my eyelids were and how cloudy my vision seemed. I was drowsy, as if I was fighting a bad hangover and still a bit d***k from the night before. I didn't know where I was - it certainly wasn't the room I had fallen asl**p in, my last memory being drinking some fluid that was supposed to offset the chemical imbalance in my system that was causing a need for me to ingest cum. I shuttered as the vivid details from the night before came rushing back through my mind, closing my eyes tightly and shaking my head to try and f***e th... Continue»
Posted by hpm12 4 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 777  |  
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Brought to Heel 2

Brought to Heel 2

Tom was bored. The shops had all shut and he had a long night shift ahead of him. He had received a call from the Manager 10 minutes ago to inform him that Ron, his shift mate, had called in sick and that he would need to do the duty on his own.

The night shifts where bad enough when there were 2 of you but on your own they were a dull and boring trudge. On the day shift you could at least use the extensive CCTV to follow pretty women around the shopping centre, zooming in where an inviting view was offered; but at night, when the place was empty there was no such light... Continue»
Posted by drooroo 1 year ago  |  Categories: Anal, Shemales  |  Views: 768  |  
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ROCKY YOUR MY GIANTESS

I have been having this wild hot dream of a friend that lives close to me a great tall CD I know on here and have been fantasizing of him getting much taller :

I see Rocky walking up the walk my huge breasts are heaving in my tight dress as I rub my big long gurl cock in my tight silk panties ,a knock at the door tells me he is here as I open the door he even with out his heels on is much taller by almost six inches his eyes are wide as he takes in my huge swelling chest that looms just below him my big clit is rock hard by now as I watch my friend get dressed he already has his long legs e... Continue»
Posted by rachels_pimp 5 days ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 796

Groundhog Day - from sissifyourself blog

The alarm went off at 6 AM, like it always did. I stirred groggily and
looked over at my fiancée Leah. She looked so scrumptious lying there
that I had half a mind to blow off work and make passionate love to her,
but instead I gave her a little shake on the shoulder. She moaned that
she was awake, and she padded off to the shower. Only having one
bathroom in the apartment meant I was shaving while she was showering. It
was hard to see in the steamed-up mirror, and sure enough, I nicked
myself.


We didn't talk much at breakfast. She had a big presentation she was
making today, so s... Continue»
Posted by slim_krak 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 767  |  
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a fantasy im wishing to come true

I always go out to the same bar on thursdays. The women are hot and long legged and they always wear pantyhose. Like usual, I dress in jeans, collared shirt and a jacket, deck shoes or dress shoes. Underneath, pantyhose. Always sheer to waist, no underwear and always nude. My jeans are long enough that no one can notice I'm in nylons under my jeans. That thursday was no different and I headed out after coming home from work and changing.

At the bar, I try to get a corner seat not far from the entrance, but along the corridor so I can see people come and go. It's a casual place, lots of busi... Continue»
Posted by leadpencil21 1 year ago  |  Categories: Anal, Fetish, Shemales  |  Views: 765  |  
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Jen big black bang

Hi my names Jen and I just turned 18 . A little more about myself I still go to highschool
like to think im in pretty decent shape . I have brown hair 34 d breasts , I guess thats why the guys
try and get at me all the time . Well my freind cindy shes 17 had met a few guys , we never really hanged out
with black dudes . They were a little older , and I dident do anything bad. I drank ocasionally but anyhow while
we were at the mall and we met them.

One of the guys was like 23 a big guy .He was really dark skinned and seemed to like me better . His name was Jamari
and his freind wa... Continue»
Posted by robd1 2 months ago  |  Categories: Shemales  |  Views: 764  |  
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The Hotel

The hotel room door clunked shut as we stood there embracing each other. The trip to the south coast had taken around three hours and I had plenty of opportunities to look across at Rachel's legs as I drove. Perhaps I should rephrase that - I had three very long hours of torment as I had just wanted to pull up into the nearest layby after leaving home and run my hands up those legs encased in black pantyhose, and up further under her mini skirt to caress her sex, but no, we both knew it was going to be worth the wait. So there we were, our pent up desires evident by our erections, holding each... Continue»
Posted by michaella_cd 2 years ago  |  Categories: Shemales  |  Views: 762  |  
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Joanna Tranny Prostitute

Joanna stood on the street corner and casually shifted her posture from one leg to the other. So far it had been a quiet evening for her with few punters around. Not many girls were plying the streets either. She’d had one customer earlier. He had been an Asian guy in a Toyota who’d stopped asking for business and after she’d explained the she was a cross dresser and he had readily agreed to anal sex .He was young, quite handsome and had treated her with kindness and respect. They’d driven to a local builder’s yard that Joanna often used and after exchangeing the money and some small talk had ... Continue»
Posted by joannacd1 2 years ago  |  Categories: Masturbation, Shemales, Voyeur  |  Views: 763  |  
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Sex in the Bar

Being a old Ex sailor it is no surprize to me that I am not shy.
I live in Thailand and worked there a couple of time over the years.
Down south near the Malay border there is a great little town where a lot of expats work and live.
I am a sociable guy and love a few beers with the boys/girls/ anybody who wants a drink.
We have a bar in one of the darkside of town where anything goes.
After dark or even during the day you can do anything in the bar.
Lady boys sucking you, young girls sucking you in teh bar besides your mates when their drinking. No shame no problems.

One day I was the... Continue»
Posted by xmas69 2 years ago  |  Categories: Shemales  |  Views: 761  |  
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Deep sexual fantasy part 1

Let me start off saying that i am a spiritual person, deeply believe in god and TRY to follow his way (which is hard being the sexual person that i am)....but i feel like this is a good way to air out my sexual desires.


Imma start off my talking about my sexual experience.

I first lost my virginity at the age of 13 when i first entered high school. The girl that i fucked was 17 years old, at first i didn't find sex to be as great is people say it is(we probably didn't do it to the fullest idk) but at the age of 17 i started have sex again. The reason behind that i was a athlete in my ... Continue»
Posted by Caribbean_Freak20 2 years ago  |  Categories: First Time, Mature, Shemales  |  Views: 760  |  
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Letting Debbie Out

Ok, this story has some explicit sex stuff, so if you shouldnt or dont want to read naughty material then please go away.

Also, I write because I want and like to. I am not a writer. Typically I write in one sitting and just do a stream of thought. I rarely edit.
But please let me know what you think. I will hopefully improve over time. And if i get enought replies that i need to edit or do something differently maybe I will.

Luv Submissive/Slutty/Sissy Sally

"I'm not sure what to do" Don said to Sam, "It sounds fun and all, but I really dont typically hang out with my employees"
"... Continue»
Posted by GreyMan44 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 760  |  
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The Bondage Whore, Chapter 7

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.



Chapter 7 - Payday Surprise

On Monday, Rachel woke up in a perky mood. The start of three days off, and also her first payday! As she swung out of bed, for once she barely even noticed the chastity belt. Rachel had spent much of her time these past two weeks daydreaming, and planning what to do with her new-found wealth. As she showered, all she could think of is what $4,000 would feel like in her hands. She'd never had that much money at one time before. One thing she knew she wanted to do, was get out of the "fleabag", in... Continue»
Posted by thongcutoffs 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 759  |  
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lesbian adventure

I had worked a day shift - I got off at about 5 and wanted to go do something. My two buddies, Niles and Will, were there and they asked me if I had ever been to this little bar in the same strip mall as the club I worked in. I hadn't. It looked dingy and dark from the outside, and since I didn't drink, there hadn't been much to tempt me in I thought. They told me I should check it out.

So we go into this place - it didn't even have a doorman! - and my eyes have to readjust to the dark. There's a stage, but no one is dancing. They order drinks - and a club soda for me - and tell me to relax... Continue»
Posted by leadpencil21 1 year ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  Views: 758  |  
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