Shemales Porn Stories
Page 114

How Nick became Nicki. A sissy story

This is the story of Nick. Nick was straight.
It was Friday night and she was getting ready to go out, she had something special planned tonight. She had her favourite pair of red and black lace lingerie on, the panties cupping her round smooth cheeks, her light blue pencil dress that hugged her figure and gave her a passable cleavage, white heels that make her look sexy even though they squeezed her toes and rubbed her heels and she had barely got the hang of walking in them. She had done her make up too, as well as she could, a little eye shadow and a cherry red lipstick. Her stomach was af... Continue»
Posted by ilgreturns 8 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Tranny orgy

You can live with someone and never really know them.
I was running a car wash in West Palm beach and every day I would take lunch at a cafe down the Blvd. The food was good, and cheap and I had the hots for Debbie, this built to the hilt redhead chick working there. She wasn't any great beauty but she had a body to die for. 36 DD tits. big hips and thick legs. Just my type. After a couple weeks I got the nerve to invite her to TGI Fridays for some drinks.
After a few, she started talking about her past. She was on parole from Ohio for cocaine trafficking. I found that interesting because a ... Continue»
Posted by kwhagie 11 months ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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Sissy crossdresser and her Black Daddy Part 2

After nearly a week of almost nonstop creampies, facials,deepthroating blowjobs and bareback anal fuckings, my black daddy and I were sad to know we had one more night in which to have our nasty, kinky fun before our respective f****y remembers return. I had dressed in all manner of nasty lingerie and costumes for his black cock to use and I loved every second in which he entered my holes. This being our last night together my daddy told me to "take a shower white slut, and make yoself pretty. I got a surprise for dat ass babygirl". My cock could hardly get any harder I was so excited. I enter... Continue»
Posted by AllisonCumms 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Gloryhole slut last night.

Well I was a horny slut last night and went to this little arcade in the city last night. Fully slutted out and in a new pair of silky nude hose I was hoping not to be disappointed....I was not!

I payed my fee and went into the back to the booths where there were a massive amounts of guys in the booths and just standing around. I was a little nervous waiting on a gloryhole booth to open but was catching the eyes of all the horny cocks also waiting for a turn in the boths. Finally after a few minutes 2 booths opened up and I went in hoping to get my hungry lips working right away. No soon... Continue»
Posted by luvpantyhose67 5 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Helping a friend

Anna has been working in my office for a year now. I have never heard her talk about a boy or girl firend. Anna is 5'7'', long legs, light brown hair almost to her waist, very pretty. I have always talked to her, had lunch, but she had never opened up until she needed some help.....

Anna had bought a house that needed work. A couple of months after she bought it, she was complaining that her sink leaked. I told her i had done odd jobs through out my life and i would be more than happy to check it before she called a plumbler. She told me to come over friday after work.

Friday came,... Continue»
Posted by edukateme 5 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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During the divorce 15 years ago

I am older maybe wiser but still a k** at heart and love to pretend. I get home Saturday around dinner time, after horrible (He’s Cheating, Has other women) things are said by my supposed loving wife of 15 years about how I mentally abuse her or the he doesn’t love me anymore innuendos. A Saturday meeting with attorneys because she cannot meet during the week due her job, this won’t be cheap. The divorce is painfully slow, meetings about this and that are beginning to feel like a hot sweaty day covered in glue rolling through broken glass! I get home and pretend that my c***dren are st... Continue»
Posted by Chartless 1 year ago  |  Categories: First Time, Masturbation, Shemales  |  
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the real me part five

Well mom and Becky left the room.I sucked Mike and let him fuck me in every postion could think till we fell asl**p.I didn't sl**p to long and got up to go get a drink down stairs.As I walked down stairs my well fucked hole felt loose and very wet and i loved it.
I went into the kitchen figued I'd make pot of coffee since I couldn't sl**p and was on cloud 9.Well I my mom came in the only thing she had on was a black gartor belt and black fishnet stockings an heels.She laughed a bit and said,dam hun you smell like just like sex.We talked while coffee was being made.she was sitting on the tabl... Continue»
Posted by cdpaula 4 years ago  |  Categories: Shemales, Taboo  |  
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my shemale GF part 7: Bukkake

My birthday was like a week ago or s o, and Christy got me what ive been wanting, a bukkake. I finally got this present like two days ago. We went to dinner, we meaning me Christy, Brittany apparently another shemale who I didn't know about but also my friend, and Jennifer, who I did know was a shemale. There are apparently plenty of shemales where I live, awesome. We went to Buffalo Wild Wings, Christy wore a short jean skirt, and nothing underneath, I know cause I dropped my fork and she opened her legs, she also had on a my Odd Future shirt on. Brittany has blonde, about 5'8, busty, big as... Continue»
Posted by germanface 4 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Retirement Home Visit

Every other month I meet a man on West Congress Street for a drink. He buys me lunch and then some drinks. The son bought me three shooters and minutes before we left I drank them all down real fast. Done. I follow him in my car to a retirement home three miles away to visit with his dad. The father is in his 70's and lives in a three room suite. The son takes me to his dad and then I go into the bathroom and wash up then change. Once I'm done I come out and put my regular clothes in an overnight bag then the son leaves.

I do this because over the past year i now like his dad and he enjoys ... Continue»
Posted by CrossdresserAtlanta 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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My ts fuck

Patong beach thailand a few years ago, a few drinhs at a bar with some friends on going to toilet at public loo which was next door to ladyboy bar. Standing and relieving myself in runs two lovely ladyboys from next door. Who proceed to do there make up and have a good look at my cock for good measure! Now at this point I hadn't any feelings one way or another, but now I was very curious indeed!
So I made my way back to my friends at the bar finished my drink and with a lame excuse left in the direction of the ladyboy bar, feeling nervous as hell I entered. It was dark with loud music a... Continue»
Posted by kawa696969 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Tranny's First BBC

Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me.

Normally it’s just the usual crowd of guys but several weeks ago a big muscular type African guy in his mid 30’s kept going past me and looking at me out of the corner of his eye. After about his third walk past I gave him a little smile. When I could see him coming down the hall the next time, I got up and slowly walked around the corner into the next hallway so he... Continue»
Posted by kbking64 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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A Day at the Beach

A Day at the Beach
By Lorenqt

I lay face down on my towel, basking in the sun, almost falling asl**p. My boyfriend Jake, he would be my husband if it were legal where we live, walked up and sat next to me. He gently stroked my left arm, "The water is great, Loren. You should try it."

Without opening my eyes, I turned my head towards him, "I think I'd rather just lay here in the sun."

He started rubbing my shoulder a little harder, "Come on, sl**py head. Get up."

"Stop it Jake!"

He gave me a quick kiss on the cheek then he whispered in to my ear, "Or, would you like me to ma... Continue»
Posted by lorenqt 3 years ago  |  Categories: Anal, Shemales  |  
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double date fun

It was just normal saturday when the phone rang.I answered it an my mom was on other end.She said can I ask you to do favor for me? I depends on what it is.Well she said, you know Cathy (moms lez lover) she called me and ask me to go out on date tonite.I yea so go, she said want to but her son just moved back in with her.I said yea don't he know about you two?Yes he does but we were wondering if you go out with him with us.I said well let me think,she said he very tall handsome an 46 yrs old.I said but does he know I am fulltime crossdresser? Mom paused a minute and said yes he does.I said ok... Continue»
Posted by cdpaula 4 years ago  |  Categories: Mature, Shemales, Taboo  |  
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FUCKING UNCLE BOBBY

The title of this story isn't really accurate as I wasn't fucking Uncle Bobby see Uncle Bobby was fucking me! He wasn't really my uncle he was just my mother's boyfriend but he lived with us so it was kind of like he was my Dad I really like him a lot he gave me lots of attention and took me places and gave me money for doing chores for him he really was a good guy! He had a boat and it was a nice one too he kept it docked at the Marina and one weekend he asked me if I wanted to go fishing with him well I loved to fish and I loved boats so hell yes was my response and we set out to go fishi... Continue»
Posted by laceysgirl 2 years ago  |  Categories: BDSM, First Time, Shemales  |  
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Through The Studio Window

November had arrived once again. The long days of summer were now firmly in the past. I contemplated such situation as I walked home from work. I changed my route recently to walk passed a ballet studio. There was a vision of beauty training on her own in that studio. Long legs, supple body and blonde hair tied up in a bun showing her sensuous neck. I loved to walk by the window and take a quick look as she practised. There was never anyone else there and the curtain was always open. I always stood there looking through the window. My penis enlarging as legs descended in her tightfitting pink ... Continue»
Posted by mrboomboom 4 years ago  |  Categories: BDSM, Shemales, Voyeur  |  
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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 5 years ago  |  Categories: Shemales  |  
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My very first experience with my classmate (episod

He was amused by the sight...of me in lingerie..standing on the porch,it was obvious he was in a shock (or state of extacy?) and couldn't take his sparkling blue eyes off my firm body inside the dress...he closed the door behind,like he was worrying if someone could see us ..I don't know why but i felt the tears running down my cheeks as a result of this emotional discharge and hugged him,saying ''I was scared to death..of losing you...I thought you would never talk to me again''...Maybe i was being hysterical but i really wasn't thinking healthy at that moment..a typical girl:) I started to ... Continue»
Posted by Slave4str8twinks 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Duty Bound- part 3

Hannah and the girls sat between the suited males with whom they felt reasonably secure; they did not know just how ‘secure’ they were to become. Hannah’s tight skirt and flashy red shoes made her feel exquisitely effeminate; she studied the bulge in Scott’s crotch and imagined being on her knees to him, looking up submissively at his stiff cock. Her soft submissiveness was to help her in the days to come; her life was to change forever. As the girls drank more and more, they were unaware that the rounds bought by the men contained no alcohol in the three drinks for the males, fairly soon so... Continue»
Posted by midsummerman 4 years ago  |  Categories: Anal, BDSM, Shemales  |  
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the feeling you get,when wearing female attire

since I was 14,I started wearing women clothesborrowing my s****r;s bra,and panties,putting them when I would shower,how the felt against my body,pantyhose,clinging to my legs,the cool sensation as I would walk across the floor.I even tryed on her majorite out fit,with thigh high boots,it was hot.now a days,when ever I'm wearing something sexy,and i'm all dressed up,makes feel like a real woman.when I would watch a porn video,I sometime wish that could have her body,long flowing hair,small breast,and of coarse a shave pussy.love wearing those tight little shorts,that would shape my ass,or the ... Continue»
Posted by blonde68 4 years ago  |  Categories: Shemales  |  
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Tranny Slave to BBC

I took a drag from my cigarette as I waited on my ride to appear. Looking around it was pitch black outside with only a waning moon and a few stars to light my way in the night. I had been waiting for about ten minutes when headlights finally appeared on the road in front of me, illuminating the sidewalk I was standing on and the stop sign beside me. I could barely contain my excitement. I had been waiting for this moment for a while. I had been fantasizing about it for around five years and I had been trying to get it to happen for about a year. It was a lot of effort, but Lord, I prayed that... Continue»
Posted by Slave_Alice1389 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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