Shemales Porn Stories
Page 7

Hotel breakfast with the Waiter Part 2

Dee and I lay in bed for a while after, and then I got up and went through into the sitting room to see what we could eat from the breakfast laid out on the coffee table. I picked up the toast as the rest was now cold and walked back to the bedroom.
“God I’m so sore. Was it good idea to take up Tobias’s offer to come up tomorrow morning?” Before he had left the waiter had told us that his name was Tobias, Toby for short, and if we were on for it, he and his chambermaid girlfriend, Cori, could come to see us the next morning for more fun. Dee of course was up for it, me too when he mentioned... Continue»
Posted by bendee555 2 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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First time as a girl

I have been dressing a bit since I was a teen but my first time dressing for a man was something. I had found him online, 40 years older than myself and talked quite a bit online. He had never been with a girl like me before but was quite interested. He bought me cloths he thought would be appropriate (love it when a man choses my cloths!) and invited me over.

At first we just sat on his couch, drinking a bit of wine and discussing life. After perhaps 30 minutes he asked me if I was interested in playing. He told me my cloths were waiting for me in the bathroom. He had bought me nice black l... Continue»
Posted by kat4daddy 2 months ago  |  Categories: Shemales, First Time  |  
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Cockatoo Part 19

Cockatoo Part 19



Nikkie Silk

I froze in the open door watching Nin and Shane fucking each other on
the bed. Nin had her back to me and Shane’s hands were on her breasts as
he drove upwards into her. They were both grunting loudly and I could
see the sweat shining on both their bodies from the effort. Nin arched
her back as she squatted over Shane taking him deep inside her. She
threw her head back and groaned loudly as she slammed down onto him
thrusting up at her. Shane yelled, ‘I'm going to cum.’ which snapped me
out of my daze.

I didn't think Shane had seen me, His mind ... Continue»
Posted by nikkiesilk 2 months ago  |  Categories: Gay Male, Masturbation, Shemales  |  
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When I first discovered nylon.

It all started for me as a young teenager when my parents split up and I went to live with my aunt and uncle and my cousin in Dagenham. Back then Dagenham was great place to be as a teen with lots to do and I made friends with other guys within days so all was good.

My aunt and uncle both worked at the ford motor company and my 19 year old cousin Vicky worked for a local firm as a secretary (I changed her name as we still see each other) The summer holidays had just finished and we had only been back at school for a couple of weeks when I fell ill and had some time off and this is when it a... Continue»
Posted by paddy-paddy 2 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
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Life changing first anal as a sissy slave

This is about my first time as a submissive sissy with another crossdresser. This was also was also my first anal with a real cock...which happened to be 8+ inches long, thick and as I figured out later also on viagra.
At that time I was cross dressing occasionally wearing stockings and knickers. I had only sucked cock twice
and although I had played with toys I never had a real cock in me., it was something that was scary to me but at the same time I was craving it.
So one night I was online talking to another crossdresser, we chatted for ages and the conversation was getting more and m... Continue»
Posted by lidacd1 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Dominated by a shemale over omegle

Stranger: i come in, dressed in a mid knee skirt, tight tube top with my d's poppingout
Stranger: grab you by the shirt and telll you to take me to you room
Stranger: i close the door and tell you to strip
Stranger: long blode hair drapped down my chest
You: *starts to strip, with a silly dance*
Stranger: i give you a pair of panties
Stranger: put htese on
You: *i try to look confused, but you can see it on my bugle that i like it*
You: ''yes mistress'' i say
Stranger: now sit on the bed
Stranger: i walk over leavingmy heels by the door
You: *sits down on the bed*
Stranger: i star... Continue»
Posted by admadma 2 months ago  |  Categories: First Time, Shemales  |  
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Amy Pt. 1

I'd not been working in the shop for long when Amy came in for the first time. She was petite, mid twenties and about 5'4" I guess with short cropped hair and wearing a loose, flowing summery dress. My first thought was of a cute little summer pixie.

She used to come in fairly regularly and I always enjoyed chatting and flirting with her. sometimes she seemed almost shy and reserved while other times she could be quite suggestive so it was kind of difficult to get a handle on just how far the flirting might go. I couldn't help but wonder what it would be like to undress her and run my hands o... Continue»
Posted by oober 2 months ago  |  Categories: Anal, Shemales  |  
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First meeting

It was the beginning of the third hour of her time in his garage. Bound to the work table that was the perfect size and height for her head to be over one end and her ass the other just perfect for a cock to enter either entrance.
The only way she knew how long she had actually been there was by looking up at the clock on the wall, she suspected that he arranged it that way just to add to her torment.
As she laid there she began to think back to the beginning of this day. She had chatted with him for a week, telling him of her desires and how watching his videos and looking at his pic... Continue»
Posted by daninrocklin 2 months ago  |  Categories: Anal, BDSM, Shemales  |  
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My date with a tranny

I had been alone for a while and I was really horny. I am not the best looking guy but cute and a little over weight. I am 6'1" tall and about 280. So going to a bar was not going to work so I started to search craigslist for some one. I found a couple women but after emailing them I found out they all wanted me to join some web site and I was not looking for that. So I kept looking and I found a woman who was real and interested in me after we exchanged emails. So I set a date with her to get together and she was excited for it as was I. I went to her house to pick her up and she was beautifu... Continue»
Posted by wildbill975 2 months ago  |  Categories: Anal, Shemales  |  
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First Time

Part 1
I knew when I was a young boy that I was different. I wanted to be a girl so bad. I wanted to dress up and look like one. I was also more intereted in boys than girls and I had an insatiable fetish for girls panties. I loved the array of wonderful colors and how smooth and silky they felt. Then every time I was alone, I couldn't wait to get them from their hiding place and play with them. I would brush them against my skin while wondering how girls didn't go around being horny all the time. Especially when their panties were so tight and with the soft fabric pressing against their love... Continue»
Posted by TS-Crystal 2 months ago  |  Categories: Fetish, Shemales, Masturbation  |  
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Cockatoo Part 18

I'm sorry it has taken me so long to produce out a new chapter. I had to stop writing for a while due to some f****y issues, which are now, thankfully, settled. Thank you to all of you who have emailed me asking how thing are going. I really appreciated those messages. I hope you haven't gone off the story in the meantime.

Previously, Nin had persuaded James to come along with her as Scarlett to meet with Joe and Nancy, two Americans who wanted a foursome. The session had finished and Scarlett and Nin were about to leave.

Cockatoo Part 18

Nancy stroked my face, looking serious. ‘Alth... Continue»
Posted by nikkiesilk 2 months ago  |  Categories: Anal, Shemales  |  
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Wife's surprise for husband

Paul and Stacey had been married 10 years and for 12 Paul had been banging on about a threesome and getting nowhere. Until one night on holiday while d***k Stacey said out of those two woman over there which would you have a threesome with? Paul replied don't know he didn't know how to answer Stacy said I'd pick the brunette Paul seizing his opportunity he says shall we see if she will? She replies no we can have one at home aslong as you promise I'm in charge and you'll do everything I say? Paul hurriedly says yes miss and they both laugh and chat some more then have the best sex they have ev... Continue»
Posted by whiteenglishbigcock 2 months ago  |  Categories: BDSM, Shemales, Taboo  |  
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Dogging by the Dock

In the areas to the east of Salt Lake International Airport, there is an area called North Salt Lake. Primarily an industrial disrict, many of the business are empty, hollow shells of a time gone by. It was one of these places that I was told to arrive at 7 pm on cool summer night.

I began my preparations around 3 pm and got a manicure and pedicure, painting my fingers and toes a deep, dark red. At 4 pm, I got waxed from the neck down. Then I went to a dear friend who is also a hair and makeup artist. We began with a shot of Jack, then she bent me over and inserted a medium buttplug in... Continue»
Posted by cdsexslut 2 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Dear Diary (glory-hole)

Well I haven't posted a story from my diaries in a while. I was changing the summer wardrobe to the fall wardrobe in one of my closets today and came across another box of my diaries. Sitting on the bed thumbing through them shaking my head thinking what a slut I was (still am LOL). Anyway i came across this entry and remember it so well I thought I would share it.
Age 21 rainy Friday night I went to the adult store to purchase a new toy. Walking in the door "Hi Michelle" the store keeper (Henry) said. I smile Hi hank how are you my love. He giggled as I did. Henry (Hank) was in his middle t... Continue»
Posted by MichelleSissy14 2 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Drag Queens in the Dorm

The head coach of the Mississippi Agricultural and Industrial University basketball team spoke to the apprehensive woman on the phone. It was Thursday, the Second of March 2006.

“Ma’am,” the former NBA power forward said. “I can assure you that we will put Mario’s education first.”
“Are you sure,” inquired Betty Ellis. “The reason Jaric went to junior college was because his grades were terr-buhl. He done got better and I want him to get his Bachelor’s cause I don’t think he can make it to the NBA.”
“I understand, ma’am. This is the last place most of our players paly competitively. We ha... Continue»
Posted by faggyboi 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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My hot wife let me watch her with bigger, ha II

What do I do with the sexually searing knowledge that my hot cheating gf is having orgasms with another man right this very minute? There is drama. There is longing, lust, trust …and provocative visions of her wearing long black satin gloves to jack another man off.

[Caption below was under a heart pounding pic of Lola sitting on our bed in black seamed stocking, satin gloves as slippery as panties. She had pulled him between her thighs so she could stroke and fondle his 8" boner. His bulge is magnificent, His fat mushroom glistening and red from her lipstick.

This was her very good frie... Continue»
Posted by bicdcuckold69 2 months ago  |  Categories: Shemales, Taboo, Voyeur  |  
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A Night with Daddy

I was little nervous but everything was ready. I had a blunt rolled and an assortment of alcohol ready for Daddy when he arrived, I love to please and everything should be perfect when my man comes to visit. I spent the afternoon pampering myself in preparation as well, every inch of my body smelled like roses, every nook and cranny ready in case a tongue came to visit or hands ventured to explore. I decided to wear something simple but sexy, my sparkly red top and tights to show off my booty, Daddy is pretty casual so no need to overdress ...we weren't going anywhere but the bedroom tonight. ... Continue»
Posted by Donna_Belladonna 2 months ago  |  Categories: Shemales, Interracial Sex  |  
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Roxanne - from ,my 'Engendered Species'

Roxanne (transexual/bisexual story)
It was a normal Saturday night apart from the fact that the world cup was on and England where playing their opening match against Italy. I had visions of most of the pubs being very busy for the 10 o'clock kick-off. Now I have nothing against football but I am not a fan, my parents where never into it and my friends often only passive supporters. I enjoyed playing football, but I wasn't good at it, I was very small and my exposure to sports at primary school was further disillusioned when one year someone kicked the football to me at full throttle, I froze ... Continue»
Posted by TVTasmin58 2 months ago  |  Categories: Shemales, Fetish, First Time  |  
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Cara TG - 'Engendered Species'

Cara (TG/shemale) - part of my ‘Engendered Species’ series

I got ready as usual, a nice close shave, both face and genitals, well you never know and I always like to look my best. I see a lot of single guys my age, mid 50's, who do not seem to make much of an effort to attract the ladies so I try to get the advantage over them. A dab of aftershave, a nice shirt and smart pants and shoes, and off we go. Confidently strutting into the local boozer, I glance around as I go past the smokers at the entrance and see a few more people than normal for this time of year, many ladies of assorted ages, ... Continue»
Posted by TVTasmin58 2 months ago  |  Categories: Shemales, Fetish, First Time  |  
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Slovene Tranny and Her American Men

Milena Dorin awakened from her slumber. She grabbed her iPhone and pressed the button to see the time. It was 6:14 a.m. She decided to get up and bathe. She walked into the master bathroom of her palatial two-bedroom, two-bath downtown condo. She pulled her douching apparatus from beneath the sink. She cleaned out her 40-inch ass. After completing that task, she hopped in the shower. The steamy, hot water felt good against her milky-white skin. She scrubbed her curvaceous figure with a purple loofa sponge and salted-caramel-apricot-scented body wash. She spent considerable time on her 36DD tit... Continue»
Posted by faggyboi 2 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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