Shemales Porn Stories
Page 81

How my chastity started

There was this woman where I worked at. She had a thing for retro and would wear business skirts, high heels and actual real stockings every now and then. She had a body to die for and legs that just simply made me melt. When she walked by I would simply melt. Could not explain it this power she had over me, it was more than just sex or lust, it was like the magnetic pull that keeps the Earth in orbit. I started small talk with her and over time we began chatting now and then. I WANTED TO HAVE SEX WITH HER SOOOOO BAD!!! But would not even flirt with her in that direction because I knew from of... Continue»
Posted by debbielynn 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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Exiting second time

After the first time had already passed, I decided to take some time as my ass still hurt a few days after my encounter. The guy I used to talk still had not sent me any message a 2 weeks after the events of the previous story so I decided to do something. After the pain went away I noticed I coul very easily play with my ass and I would not hurt at all! I went to the point that I could fist myself and it would rarely hurt.I played putting things in my ass and it felt awesome. I decided I was 100% bi and wanted to try something new, so I began crossdressing more seriously. I went to swimming l... Continue»
Posted by Ktm999 7 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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me my daughter and a shemale

my last story was with my daughter for the first time now we both have shemale girlfreind very beautiful ones they would come over me and my daughter would put on our sexy heels she picks my shoes now lol and they would fuck us both on the same bed theses shemales are in good shape they would fuck me and my daughters tight lil asses and shoot globs of cum then they would watch us creampie it out one of them came over one night when i got off work my daughter wanted me to tougue out her shemales ass while she shoots in her pussy she has a big dick mine would never reach in that far i loved watc... Continue»
Posted by keiporn 4 years ago  |  Categories: Shemales, Taboo  |  
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total sissy humiliation

my phone buzzed.

looking at the screen the name before me both puzzled and startled me.
I had posted an ad on craigslist 10 days ago, offering to suck cock. i was 32 and had been dressing as a girl and fantasizing about sucking cock since i was 13.....and now being single, I'd decided to act. within 12 hours of my ad going live I'd had 10 emails from guys...some of which i deemed timewasters. I'd quickly narrowed it down to a guy named Lee...at least thats what he said his name was.

Lee lived locally, and worked as a bar manager for a local pub. I knew the pub, it was a normal quiet pu... Continue»
Posted by hornyTVluvr 10 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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My Sexual Resume

About Me

I am a very sexual crossdresser who enjoys all sorts of activities. I have a small cock which I milk on a daily basis. I love to be photographed when I am with someone. You might say that I am a exhibitionist, when I am dressed like a slut.

Sexually

I am bi sexual and love women as much as I do men. I am very oral, anal, and a kinky submissive. I like to be used by men and women when I am dressed. Those that have been with me usually leave satisfied, which for me would be a face full of cum. I love those hollywood pop shots all over my face. I love kissing and fingering of m... Continue»
Posted by slut2eatcum 5 years ago  |  Categories: Shemales, Taboo  |  
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shemale sex slave

BDSM JOURNEY.

Let me first say i am no writer by any means.

This story starts 5 years ago. I was looking to move up in the mountains off grid with a homestead. I was a single man and wanted a parnter who could share with the daily chores and have for sexual gratification. Finding some one to leave everything the city offered to move to a rural area was a quest in itself. I knew I wanted a completely submissive woman ant my feet.
So I put a ad on craigslist and it went a lil something like this" tall single white dominate male iso single submissive woman to move to a homestead in a very ... Continue»
Posted by bigfranks36 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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One experience with two blak men!

Hello again this is EvA…I am a 40 year old tranny. I do not consider myself a cross dresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine lady boy. I have been taking also hormones for 4 years, on and off and I already saw many changes…my boobies are growing, becoming poutier and have sensitive nipples. My skin is sooo soft and my hips are getting bigger giving me a pear figure… I also see changes in my feelings, being more sensitive and sometimes I cry when I watch a romantic movie…haha. One of the biggest changes also is that I am alway... Continue»
Posted by transeva69 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Deep throat Made Easy

Deep throat Made Easy -reposted fro menext


Here for the first time ever are simple and explicit instructions on how to deep throat a penis. Position is important; you'll want to in position where you can extend and straighten your neck by slightly tilting your head back. This helps line up your throat with your mouth allowing the penis to slide in deep. The best position for beginners is with the receiver lying on his back with the giver lying on the stomach along side. You can prop yourself up on your elbows.

The penis must be THOROUGHLY LUBRICATED! I can't stress this enough. An... Continue»
Posted by bigdaddycoolzz 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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The Hotel Part 1

I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days.
Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, f***ed fem, huge dildos, and giant buttplugs are just a few of my fetishes, and I expected every fantasy to be fulfilled this week.
As I pulled up under the awning of the front enterance I was met by a woman in a French Maid uniform. I introduced myself, and said I was checking in fo rthe week. She smiled, as she opened my car door, helped me out of the car, took my ba... Continue»
Posted by NJStraponLover 4 years ago  |  Categories: Anal, Fetish, Shemales  |  
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First Time By Transsexual

When I was 21, I spent a summer in a southern city doing a service project. I was engaged to a girl and excited about marriage, but I was also extremely curious about the male body. I was one of those k**s that masturbated constantly, and almost always about sex with a man or a transsexual. The summer before my senior year, I was down in this southern city living completely on my own for the first time. Since I was doing a service project, I only got one night a week off. I wasn't sure what to do with that night since I didn't know anyone, so I decided to get d***k. Several times, I just went ... Continue»
Posted by kbking64 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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The Ebony TS of my dreams


This story is about one of the most memorable piece of cocks I've ever experienced in my 30 plus years of getting fucking. I just thought I'd write it down and share it simply because I'll never forget it and because I'm a married man and it most likely will never happen again.

It happened about three days ago with TS Dominique I met through the internet(EROS). She was 23, but she easily looked 20. She kept her body pretty fit. She was about 5'11 and 135 lbs. I love tall women because I'm physically a big myself--6', 245lbs. It's hard to be fucked by a woman bigger than yourself. Plus, I... Continue»
Posted by yesamwilling2 4 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Old Black Carl (part 3)

Old Black Carl (Part 3)
After the long night, we slept in late, the next day. Carl made me suck his cock again, and of course, I enjoyed it. He said he had some things to do and that he would drive me home, so that I could rest, and that he would be picking me up again that evening. He drove me home with his arm around me, and of course, he had me play with his big cock while he drove. He dropped me off in front of my parent’s house, and told me to be ready about 6. I nodded, and walked into the house. I knew I probably smelled like cum and sweat, so I went directly to my room. I thought abou... Continue»
Posted by cocksucker4bbc 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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A Girl To Remember

Senior year is supposed to be the best year of high school. For me it was absolutely remarkable. Junior year, second semester, I went to the office for my teacher. A girl I liked helped in the office for her free period. She was Japanese with long black hair that fell down her back. She had icy blue eyes that were accented by her black eyeliner. She had on black lipstick, black converse, and a black and purple skirt with black pants on and a black t-shirt with purple letters that read, “If you think you’re normal. You are weirder than me and I’m a Goth.” She looked like a little Gothic fairy. ... Continue»
Posted by nightheart13 2 years ago  |  Categories: Shemales  |  
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CD And Trucker

CD Adventures Truckers Ch. 02a
Part 2A: Portland to Bakersfield
I turned....
At least four things went through my mind the moment I heard Hank ask me to go along with him.
- One my wife was gone for at least 2 weeks so that was no problem.
- Two, with wireless connection and my laptop I could take my job on the road.
- Three, I had hardly any clothes in my bag that I was carrying. All the clothes in the bag were girl
clothes; my boy clothes were in the back seat of my car.
- Four, my ass (oops, my pussy) was on fire and now stinging a bit from Hank's big cock taking my
virginity just ... Continue»
Posted by pr1456a 3 years ago  |  Categories: Shemales  |  
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The real me part one

Well let me began Iam not in the closet, I grew up in small town my mom raised me cuz my dad was not around. This town was dead and in my school days there was only myself and friend of mine that were the only k**s in town. It was summer and my friend had left to go spend the summer with his grandmother in other state.
My mom was a 5'9" 130 lbs d breast woman that raised me and worked her but off doing it as only hair stlies around for a 100 miles. She always wore dress and skirts and heels dolled up everyday. So oneday I was bored around the house when she was home taken a break. We were... Continue»
Posted by cdpaula 4 years ago  |  Categories: Gay Male, Shemales  |  
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xdresser foxxiroxxi fucked by daddies poker buddie

So I have finally got my men doing what ive wanted for a long time now and I have never been so horny . John is licking and fingering my ass while im getting marcuses tounge shoved in my mouth all the while my daddy and his buddies are outside . Fuck me im so fucking horny these guys could do anything they wanted to and I wouldn't stop them. Johns fingers start at one then two big black fingers slowly stretching my virgin ass then he slipped a third in and out licking and sticking his tounge in my ass then fingering me ,he kept the same pace making sure he didn't rip me so it would be a pleasu... Continue»
Posted by foxxiroxxi 3 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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Daddys whore


I had always been fascinated by the feel of womens clothes against my skin, and today was no different. Mom was away on a business trip to Canada, and dad was away at work for the next couple of hours.

I had always had an effeminate look to me, with me being 6’1” and thin as a twig at 19, I was scrawny. I had bought a black wig to go with the outfit that I had picked out. It was black 6” heels, black pantyhose, a black garter belt and panties, with a short black skirt and a little black tube top. I was hard just thinking about what I would look like.

I took a shower and completely shav... Continue»
Posted by nicoleinberlin 3 years ago  |  Categories: Gay Male, Shemales  |  
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Alice 2

Alice part two

I checked out and drove home in deep thought, I knew I was in love with Carol, I could only hope that she felt the same about me. How am I going to explain to my dad about dressing up and most importantly about my job. I decided that I would be dressed when he got home from work, then tell him what has happened, he obviously would have found me out anyway. I arrived home about lunchtime, I stripped off, had a shower and douche, I picked out a nice black above the knee cocktail dress, nice silky black underwear, near black ... Continue»
Posted by ratty9uk 5 years ago  |  Categories: Anal, Shemales, Taboo  |  
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More Dirty Sex with Tania. Part One Hotel Sex

More Sex with Tania


Part One. Hotel Sex

It took quite some planning, after our last meet in the lay-by, but at long last we had both been able to get away at the same time. We, well actually Tania, had arranged our meet to be at the Premier Inn at Witcombe, just south of Cheltenham and just of the A46. Tania was arriving just after lunch and myself at about 3ish. We agreed it that way so it gave Tania time to dress and get ready, however it did mean that I would have to arrive dressed as Joanna. I have a lot of confidence when dressed, as Joanna but most of my forays have been either a... Continue»
Posted by joannacd1 5 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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my first time

this will be the last story i write unless someone asks me personally for more... as Andy i felt no one loved me and if i was a girl i could be that slut and try to feel some kind of love from someone. when i was Andy i dated 6 girls in the course of 2 or 3 years and 4 of the 6 cheated on me and the other two clearly hated me and made my life nothing but misery... Ana was my only way to feel any kind of love or happiness.. when i first dressed as Ana no one was interested in me i was shy and i was still trying to find the right look for me... one night i decided to go to a party and find the d... Continue»
Posted by drewcd 4 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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