Shemales Porn Stories
Page 111

Kelly gooes to college Part 2

I was a little shocked to here him say this, and i was a little buzzed, so i challenged kenny right then and there. "If you think I'm so hot big boy, why don't you fucking kiss me?" I said sassily as i stood with my hands on my hips as if to challenge him physically. To my suprise he took two steps towards me, wrapped his arms around me and kissed me deeply, our lips touching softly as they melded into one for a moment, then parted, our hungry tounges darting and probing each others mouths as we stood wrapped up in the heat of one anothers passion, never wanting the feeling of ecstasy between... Continue»
Posted by dirtygurl4u 3 years ago  |  Categories: Shemales  |  Views: 691  |  
98%
  |  3

The Bondage Whore, Chapter 1

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


Chapter 1 - Job Interview

It was around 4:30AM and Rachel St.Clair was beat. Walking the streets for such a small amount of money really sucked!!.. And no pun intended, Rachel wryly smiled. The streets were now deserted, no more money to be made tonight. Rachel started to head towards the seedy hotel where she barely managed a one bedroom fleabag. "I've got to find a way to make some better money", she sighed to herself.

Rachel was now 24 years old, and had been walking the streets since she was 16, after an abusive sugar... Continue»
Posted by thongcutoffs 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 999  |  
89%
  |  11

The Bondage Whore, Chapter 2

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


Chapter 2 - The Fitting

The next day Rachel arrived at the office. It was mid-afternoon, around 3pm. Today Rachel was wearing her shortest denim miniskirt, too short to completely cover her ass, strap-on heels, and one of her favorite tops which displayed several inches of midriff. Monica greeted her, and introduced her to Phil, who would do the "fitting".

"Come on into my office Rachel." said Phil as he directed her through another door. Monica followed.

Phil was very business-like and proceeded to measure Rachel's ne... Continue»
Posted by thongcutoffs 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1042  |  
89%
  |  10

My first time witha a shemale.

I was holiday in Spain with my friend and his Mum when i was 17, we didnt have any problems getting served in the bars so went out every night drinking. Half way through the holiday we all went out and me and my friend ending up in a club quite the worse for wear, a girl was dancing against a pole and keeped looking at me so i look backand maintain eye contact, she danced in my direction so i danced up to her and as she started to grind against me i started feeling her tits, she turned round and led me by hand to the girls toilets, there was other girls in there but we went straight to a cubic... Continue»
Posted by JD85 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2159  |  
78%
  |  2

Road trip


I enjoy dressing as a female. I do it as much as I can. I wear nylons or tights, support panties or girdles, and bra’s regular or long line under my clothes. I have a pair of knee high boots with 4” heels that I wear when I can. I am also into bondage.

Every now and then I get a chance to do both. This is the story of one of those times. I had to make a trip from Memphis to Nashville. It was to be an overnight stay. It also was going to be a daring fetish bondage trip.

I packed for the trip. More bondage and cross-dress than anything else. I took ropes, cuffs, my favorite vibrating dil... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1008  |  
100%
  |  4

June 3rd 2011, Dream Come True!

Friday June 3rd, 2011, I went out to a local bar. Not crossdressed, just the man in me. I am normal on the outside, beer drinker, hell raiser, party kinda of guy. So anyways, im sittin at the bar with my buddy sam, drinking coors light and shots of cuervo. well sam had to cut out early cause his wife was getting bitchy, so he left and i stayed and got d***k. at the other end of the bar i was eyeing this gorgous red head, id say, 5'3, slim body nice tits, drinkin beer, which is a turn on for me when women drink beer!! And she noticed i was lookin at her. So i got up with my beer and went outsid... Continue»
Posted by sissypantyhoseboy90 3 years ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 844  |  
94%
  |  5

Kelly gooes to college!

this is another installment of my life as a girl, im gonna flit around the different parts of my life so enjoy!

Wheni was eighteen i went off to college, no more sexy playtime with my best friend B (or nicole, which is what i will refere to her as) no more sl**ping in panties and a babydoll or short slip, or anything kinky! My first year i lived in a double and my roomate was a partier, constantly bringing home d***k girls and having loud, sloppy sex as i lay in my bed stroking my girlie cock and fingering my tight little whole, imagining it was me being a dirty slut and getting fucked goo... Continue»
Posted by dirtygurl4u 3 years ago  |  Categories: Shemales  |  Views: 904  |  
86%
  |  2

My night of first times!!!

I was sitting in the bar with my friends when she walked in. Black short dress, low cut neckline. I can see the garter straps holding her stockings. I think that is what caught my attention first. I had seen garters and stockings in movies but never in real life and her legs looked great. I couldn't keep my eye off her all night. I had to seem like a stalker with my eye's, I wasn't paying much attention to the conversation at the table with my friends she was lust at first sight. I had to make a restroom trip and when I walked out she was standing there. My heart skipped a beat and my stomach ... Continue»
Posted by Trudru 3 years ago  |  Categories: Shemales  |  Views: 1955  |  
97%
  |  6

My first time with another crossdresser.

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my b*****r and s****r. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer to waist with reinf***ed toe suntan wolford pantyhose. They were incredibly silky and soft. i rubbed t... Continue»
Posted by sissypantyhoseboy90 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 4460  |  
18%
  |  18

Passionate Sex with a Beautiful Shemale

Passionate Sex with a Beautiful Shemale


a man and his shemale lover get down to business
Will led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sarah lightly ground her ass into his crotch, rubbing herself against his hardening cock.

“Mmm,” she moaned, feeling Will’s lips kiss the nape of her neck, causing her to break out in goosebumps.

She turned to face him, wrapping her arms around his n... Continue»
Posted by adel5000 3 years ago  |  Categories: Shemales  |  Views: 618  |  
92%
  |  1

Gang banged in bondage by shemale co-workers

I had just got home when my cellphone started to ring. When I anwered I heard my boss on the other end of the line. And she told me to come to her house for some "Fun" in a very ¨seducing voice.
After I took the buss there and walked up her driveway I kept wondering if my great looking boss and her sexy secretary was gonna tie me up again. The first time had been a real suprise but I had still enjoyed it in the end.
When I knocked at the door her secretary opened it and beckoned me in.
When I came into the living I came to the conclussion that I would be tied up again. There was bondage equ... Continue»
Posted by Ankakalle 3 years ago  |  Categories: Shemales  |  Views: 1357  |  
94%
  |  4

Gang banged in bondage by shemale co-workers

I had just gotten back home after work when my phone called.
-That´s strange.
When I answered the phone I heard that it was my boss that called.
- Can you come over here please?
She said in a rather seducing tone.
I guessed that I didn´t have much of a choice so I said yes and drove to her house.
Just like the last time her secretary opened and asked me to come in.
-Ms Boss is waiting for you in the living room.
She also said that this might take some time.
Whe I entered the living room I realised that I was gonna get tied upp again. There was bondage stuff al around the room! Dildos,... Continue»
Posted by Ankakalle 3 years ago  |  Categories: Shemales  |  Views: 734  |  
95%
  |  5

Fucked by the Mailman

This is true, One day last year I was home and dressed, Nails lipstick, and a very short dress. I was watching porn and using a large toy! I was hot and horny! The doorbell rang and without thinking I got up and answered the door. It was my mailman. He is a big guy, 6'4 white and a bear type! When I saw him the first thing I said was OH SHIT!

He looked at me and said I never knew! But if you don't suck my cock I will tell your neigbors! What would you do? I let him in! More later... Continue»
Posted by Cherrycd 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1942  |  
62%
  |  1

First time getting caught wearing Pantyhose

When I was 16 years old, I babysat for my moms best friend. I had know Joanne (my moms bff) all my life, she was my second mother. and a single mother at that. And Joanne was smokin hot! Had thee biggest crush on her since i can remember. Joanne always wore pantyhose or stockings, and i mean always, one night i slept over at her house, i peeked in her bedroom and she was wearing a teddy and pantyhose, and ofcourse i had to masturbate, because like i said, she's a woman who gives an instant boner at first sight. Anyways, she had asked me to babysit her 2 boys on a friday night. Not a big deal e... Continue»
Posted by sissypantyhoseboy90 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 5909  |  
90%
  |  28

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 3 years ago  |  Categories: Masturbation, Shemales, Voyeur  |  Views: 757  |  
95%
  |  2

Becoming the girl i am part 2

I smiled impishly at B, standing there before me looking so sexy in his see-thru camisole, skimpy thong panties and heels. "Sooooo, can i dress up too?" i asked as i stood up and walked over to my best friend. "Sure, if you want to!" he replied excitedly, "you really want to?" Of course i do!" i told him in an excited voice, my own inhibitions overcome by the heat of passion we were having. "Go thru the other bathroom door into the spare room, my s****r clothes are all in there! Pick out something sexy!" he whispered as i slipped into the spare room. I opened the pantie drawer and spent som... Continue»
Posted by dirtygurl4u 3 years ago  |  Categories: First Time, Shemales  |  Views: 424  |  
81%
  |  3

Shopping

As I walked through the shop my heart raced. I was here for one reason. To buy women’s lingerie. I had always chickened out at the last second and was determined to go through with it today. I slowly made my way into the small shop browsing over nothing in particular when a older good looking guy came up to me.

"Is there anything I can help you with" he asked with a grin.

"Uh...yeah....I was uh, looking for something for my girlfriend." I asked nervously.

"What exactly are you looking for?"

"Uh, something sexy."

I just knew he could see right through the lie but he didn't let ... Continue»
Posted by welshcd 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 2312  |  
95%
  |  11

becoming the girl i really am part 2!

I smiled up at my best friend, dressed up in sexy lingerie and smiled, "Can i dress up too?" i asked in a hopeful tone of voice. "Oh, wow, really? Yea sure!" brian answered with excitement in his voice. "Go into the guest room, my s****r keeps all her clothes in the dresser and the closet, and pick out soemthing you like!" he said, "Pick something really sexy" he whispered as i slipped out the door and into the guest room.

Going through the dresser i found a drawer full of panties, i felt a rush of excitement as i examined the soft, silken panties....thongs, bikinis, g-strings and boy s... Continue»
Posted by dirtygurl4u 3 years ago  |  Categories: First Time, Shemales  |  Views: 487  |  
100%
  |  2

Morning Routine at the Mansion of My Misstress


My eyes open with the gentle humming of my small alarm clock. I quickly shut it off so as not to disturb anyone else in the room. Its 4:30am, well before light creeps into the day and the room is now pitch black. Very quietly I rise up on my hands and knees and crawl off of the small doggy bed on the floor next to the big bed. It‘s embroidered with my name “Heather” in pink because it’s my bed and I’m the pet of my Mistress.

I’m silent when I move because I have done this so many times before. On all fours I make my way to the master bathroom and gently close the door behind me. I then st... Continue»
Posted by heatherlingerie 3 years ago  |  Categories: Fetish, Shemales  |  Views: 1142  |  
96%
  |  9

A night out with my s****r

Following in from Shopping with my s****r - Please read my other stories first to set the scene.

Jane and I lie embracing on her bed, our naked bodies merging into one as we hold each other closely.

"What do you want to do tonight?" I ask

"I was thinking we could have a night out together, maybe a meal and a few drinks, see where the night takes us!" Jane replied.

"That sounds good to me, I haven't been out for a few weeks because of my exams."

"Well, I'll treat you to a nice meal and a bottle of wine on one condition" Jane offered with a devious smile on her face.

"Go on,"... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3244  |  
13%
  |  10