Shemales Porn Stories
Page 113

I Knew I Was A Sissy (Part II)

For the next months I kept serving Nick at his will, usually every Saturday morning. It was convenient as his parents would go at the Super Market for shopping and I could use studying as an excuse.
We would meet at his place (not the garage anymore but his room) and I would give him a blowjob and let him fuck me. He kept his part of the deal (not spreading the news about me) and I kept mine.
I was enjoying it to be honest. At the same time on every chance I would go over my s****r’s room and “borrow” some of her thongs and stockings and dress up. My cock was getting hard every single time... Continue»
Posted by georgette32hk 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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My First Time as a Girl

I was hoping to hook up with a straight guy.

I have 2 b*****rs and a s****r I’m the youngest and a Freshman in high school. Always been fem preferred to play with my s****r and her dolls. My dad is an ex-marine. Tough guy. My b*****rs are following in dad’s footsteps, military orientated. I‘m a big disappointment. My dad accepts me for what I am now. My mom always stands up for me when my dad criticizes me for acting like a girl.

My b*****rs look on me more as a s****r than a b*****r. Weird as it sounds I am more fem in a way than my s****r. I like to dress up in my s****r’s clothes and... Continue»
Posted by kbking70 2 years ago  |  Categories: Anal, First Time, 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 9 months ago  |  Categories: Group Sex, 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 4 years ago  |  Categories: Anal, 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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Halloween fun

Here's an interesting story that happened to me last Halloween, hope you like it. Last October, a local bar had a Halloween costume contest. Since I had nothing better to do (I'm too old for trick or treat) I decided having a beer and checking out all the silly costumes would be fun. I sat near the bar and almost immediately a sexy, slinky brunette caught my eye. She was wearing a light blue dress, black seamed stockings, and dark brown "fuck-me" pumps. After a short time I went over and said hello. She was smart and funny, and we really seemed to get along nicely, but with the loud musi... Continue»
Posted by throbbinghardboner 4 years ago  |  Categories: Gay Male, 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 4 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 3 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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Daddy at the Truckstop - 1

--This was an encounter that almost happened with a Daddy a while back. We talked about doing this for a first meet to make up for other times that didn't work out, and while talking about it with him was undeniably hot, it ended up not happening for a few reasons, chief among them safety. I think about how hot it would have been to smash a lot of my boundaries this way, though. Enjoy, and comments welcum :) ----

I couldn't believe I agreed to this, but here I was. The truckstop is maybe an hour from my house, and I was pulling into it from the highway now, dressed in stockings, panties... Continue»
Posted by StaceyDeprave 7 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
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My First Time With Old Man in Girls Undies

First, me say, this is a true story of how I lost my anal virginity but to protect my privacy and the people in the story, I will be changing people’s names.
This story is set when im s*******n and had just began experimenting with crossdressing and having gay thoughts. My favourite categories on this site are Bisexual, Anal, Shemale Fuck Guy, Guy Fucks Shemale and Latex. I was also broke as fuck and unemployed and summer was just around the corner so I needed money fast. It was around this time I remembered about the casual encounter section of Craigslist. I had been wanting to experiment w... Continue»
Posted by TeenTranny 9 months ago  |  Categories: Gay Male, Shemales, Taboo  |  
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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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Dr. Visit.

I turned 50 and the Dr. called and said I needed to make an appointment for my birthday physical. Well my birthday fell on a Friday and my appointment was the doctors last one of the day.
I was sitting in the waiting room and saw all the employees left the office. I asked the last one exiting if I had been forgotten? She laugh and said no, then she said that I was the last one of the day and that the doctor was running just a few minutes lat. I thanked her as she was walking out the door.

About three minutes after the last employee left the building the doctor came out from the back and ... Continue»
Posted by scottyj53 4 years ago  |  Categories: Anal, Hardcore, 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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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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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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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 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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