Shemales Porn Stories
Page 110

A Sissy's Long Night Pt.1

We were to meet at a hotel, the seedy kind where nobody respectable would go. I was to meet him in his room, just down the hall from mine. I was very nervous. This was my first time meeting someone like this. Usually, I knew the person before hand, and always met at private parties where other people were around in case something went weird.

No, this time, we met online, chatted, exchanged pictures and then arranged to meet. I changed out of my jeans and workshirt. My clothes laid out on the bed, my make up already set up, wig on its holder. I took my time with the make up, I keep it... Continue»
Posted by sissystephanie2008 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 279  |  
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Back Seat Backdoor part 2

After our back seat get together, I was hoping that I would get chance to play with my big black stud in a more comfortable roomy spot. We chatted off and on flirting and teasing each other for a couple of weeks, and everytime I talked to him, my ass would quiver just thinking about how good that huge cock felt. One Saturday afternoon I got a message from him telling me to meet him that he was at a friends apartment and if I wanted to come over and play, he would love to. "have" me. I couldnt turn him down, and I got in the shower, shaved everywhere and made sure I was clean as a whistle. I sl... Continue»
Posted by LRock4fun 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 844  |  
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Straight man enjoys chubby fem guy

So I met the straight guy online he said he was looking for full figured woman nice tits nice pussy. I messaged him and asked him have you ever been with a somewhat chubby fem guy he said know. I explained to him I had breates like a female and a bottom like a pussy just tighter. He would make love to me same as he would a girl. He was gamed to give it a try. Oh and did we enjoy each others company. We got together at his house I came in we started talking a bit he had some porn on. We had a couple drinks so I grabed his hands and he leaned into me and kissed me as he would a woman tounge and ... Continue»
Posted by pussyboy76 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 510  |  
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THE FIRST TIME (FIRST STORY MY NOT BE THAT GOOD)

ONE STORMY NIGHT A MAN WHEN IN TO THIS CLUB TO GET OUT OF THE RAIN. WENT TO BAR TO GET A DRINK AS HE WAS WAITING HE SAW A BEAUTY AT THE END OF BAR. AS HE LOOKED HER WAY SHE SMILED AT HIM.AND SHE WAS WALKING OVER. AS SHE WAS HE SAW THE MOST SEXY LEGS HE EVER SAW. THE BLONDE WOMAN SAT NEXT TO HIM AND HI. HE WAS SHITING HIM SELF AND FINALLY SAID HI BACK. SHE SAYS SO U R U.THEN THEY A GOOD CHAT.SHE THEN SAYS OK LETS GET OUT OF HERE HE THOUGHT HIS LUCK HAD CHANGED. SO THEY GOT TO HER PLACE. SHE PUSHED HIM THE BED AND TURNED AROUND AND SLOWLY UNDOING HER DRESS AS THIS WAS HAPPING HIS COCK WAS GET HA... Continue»
Posted by LORDLONE 3 years ago  |  Categories: First Time, Shemales  |  Views: 331  |  
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My Feminization of the day

Ever love the feeling of a woman cummin on you? Well I felt that this evening after I picked up a random woman off the street who asked to be drive home. When we reached the house she asked me to come in. I did and she actually blindfolded me into here bedroom where she tied me up on her bed. I didn't need that but I just played along with it begging to be let go. Of course she didn't let me go. Then she started to tear off my clothing and found me wearing a bra and panty. Then she said,"Well aren't you dressed up nice?" she pulled on my panties and let go juggling my balls around. She laughed... Continue»
Posted by SissySlut9084 3 years ago  |  Categories: BDSM, Shemales  |  Views: 620  |  
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My New Mistress

Ever love the feeling of a woman cummin on you? Well I felt that this evening after I picked up a random woman off the street who asked to be drive home. When we reached the house she asked me to come in. I did and she actually blindfolded me into here bedroom where she tied me up on her bed. I didn't need that but I just played along with it begging to be let go. Of course she didn't let me go. Then she started to tear off my clothing and found me wearing a bra and panty. Then she said,"Well aren't you dressed up nice?" she pulled on my panties and let go juggling my balls around. She laughed... Continue»
Posted by SissySlut9084 3 years ago  |  Categories: BDSM, Shemales  |  Views: 525  |  
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First Public Experience

From my previous stories you’ll know I love to dress up in lingerie. After a small number of sexual encounters with men I decided it was time to take things to the next level. I told a lesbian friend of my cross-dressing and asked her to take me to a gay nightclub dressed as lady. I didn’t want to go on my own. She seemed surprised but agreed. All week I wondered what to wear. By Friday I settled on a skin tight white dress with matching high-heel shoes. I spent the previous evening waxing and plunking my eye brows. I wanted to be as feminine as possible. Friday evening i began to get ready. I... Continue»
Posted by monkeynuts0 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 579  |  
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Honolulu surprise

I haven’t written a story in a while because I moved from Asia to the US and have been busy with work.

Back in Honolulu, I used to fuck plenty of women as I was young, tan, blond, and in super shape with Triathlons. Mostly I would try to close the deal really quickly after I met someone, just going with “Hey you wanna go fuck?” question after a few minutes of chit chat. You would really be surprised how often this technique worked. I got slapped a few times and a few “fuck you’s”, but really it worked more often than not. Actually, looking back it is only logical I would continue to use thi... Continue»
Posted by mahuluvr 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 894  |  
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Cumming of Age

When I was younger I can remember summer vacations with the guys. We were a small group of six or seven close friends. I can't remember who made the suggestion but we would set or stand in circle facing each other and masturbate. I'm sure that is when I first sensed a curiosity of having sex with another guy. I know I've always enjoyed watching another guy get off ever since those early days. Glory holes would cum later.

When I got older my sexual thoughts pointed me in the direction peep shows. It was pretty much an age of sexual freedom when the only worry was how fast could I get a... Continue»
Posted by milkmanj 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 655  |  
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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 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1564  |  
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First time with a shemale

I must have been 16 back in the day, but I always looked older so it didn't really affect anyone's judgement in the sex world that I had loved since I can remember jerking off for the first time.
I was walking the streets of Amsterdam that day, the Red light Disctrict looked like paradise on earth, all those hot hot girls smiling and telling you to come in...I don't even know how much they wanted, I didn't care, just walking in those tiny streets and seeing those creatures was more than enough.

There pretty much everything there, from the porn starlet straight from Poland to the big Colomb... Continue»
Posted by joelo 3 years ago  |  Categories: Shemales  |  Views: 771  |  
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Fun with Stephanie-Gurl at the Park!!!

Fantasy Story: Fun with Stephanie-Gurl at the park.

After weeks of chatting online I was able to convince Stephanie to meet me but she had one condition it has to be in public place. Now I am not one to hook up in public but I was dying to meet Stephanie and have a little fun. I knew of a park that was nearby that we could meet at late at night and she agreed to the location. That night I arrived at the parking lot of the park around 11 o’clock and waited in my car. Of course being the sexy gurl she is, she made me wait. We had agreed to meet around 11 but I was waiting for almost 45 min... Continue»
Posted by Ryu1313 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1567  |  
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My wife dressed me and used me like a slut

I think you are about ready my wife “Jen” exclaimed and she rotated me towards the mirror. My cock was already rock hard and sticky soaking the silky panties as I looked at my reflection. I gazed at my blonde shoulder length wig bounded into two braided pig tails, my face heavily coated in foundation, my eyebrows and lashes painted dark, around my eyes multi shades of blue and my lips a glossy pink. I could feel the silky tiny cup bra as it rub across my nipples, I could feel the top of the multi colored leggings clasping my thighs with the feeling of the tiny skirt that just covered my pantie... Continue»
Posted by Zeffer1 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1903  |  
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First BJ

I have always felt that I was a Woman born into a Man's body. Growing up I remember seeing my Mother in a girdle, garterbelt & Nylon stockings. I always felt that I wanted to wear them also. In school I watched the Girls start wearing their first bras, Nylons, garterbelts, makeup, heels etc. & also listened to them talk about it along with their "Boy" stories. I so wanted to be able to join in but of course couldn't! I had worn stolen or thrown out pieces of lingerie & of course tried on my Mothers but it still wasn't like having my own. I also had wondered what it was like to suck a Man... Continue»
Posted by nyloned1 3 years ago  |  Categories: First Time, Shemales  |  Views: 692  |  
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dressing up

have been ‘dressing’ from a young age, the usual situation occurring, finding an aunties pink satin brassiere, a long line one which just hung on me, but that didn’t matter and also the matching corset also too large, but it felt so natural to wear these items, it gradually developed into wanting to dress more and more frequently, then it was dressing from there on.

My final transformation started about 7 years ago my wife had arranged to go away for a weekend with friends, a sort of girls weekend. I was ecstatic, my chance to dress for a weekend properly with no interruption. After she ha... Continue»
Posted by manfed 3 years ago  |  Categories: BDSM, Mature, Shemales  |  Views: 823  |  
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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 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1397  |  
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Unexpected Secret

My neighbor and I get together almost every day after my husband goes to work. We have become very good friends. We go shopping, watch soaps, play cards, and cook together, all kinds of stuff. Her name is Linda. She recently revealed to me that she has a secret and isn't all that she appears to be.

Linda said she is a man who has been living full time as a woman for ten years now. She said she had breast implants and electrolysis. I couldn't believe it! She is feminine in every way. Her looks, mannerisms, clothes, make-up, body language, voice, everything, is always a woman.

So, I asked ... Continue»
Posted by nova169 3 years ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 2792  |  
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car fun!

Some years ago, I had overnight business travel and I cross-dressed in my motel rooms after hours. I had some married men that I met online that would come see me when I was in their towns, and get some sweet head from me on their way home from work or whatever. One of my regular hookups, named Frank, pulled into the motel parking lot late one afternoon and looked up and saw me on the balcony. I was in a mini dress; heels and all dolled up, waiting for him, but was just getting a little "exposure" time in, as I waited. When Frank came in he said that he could tell that I was into being seen an... Continue»
Posted by dana213 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1091  |  
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Leila's Secret

I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most.

It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before.

I'd stayed over at a friend's house and after a nice leisurely breakfast I headed home so that I would be back home before dark. I had to be at work the next day and wanted plenty of rest.

I was driving along Highway 1 when I first saw her. And boy, was she a vision. It had been raining all morning and the woman who stood there beside the road w... Continue»
Posted by nova169 3 years ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 1381  |  
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All grown up part 1

It has been about 3 years since we all moved into our own house and my s****r even with her stunning looks and drop dead gorgeous face she could not hold down a relationship. The boys she went out with were all not very open minded and ended the relationship by the time they got the bedroom and over the months you could see she was a little down because of it.

when she was 21 years old she found a boyfriend and he was the friendliest of the lot she had met and we all got along quite well. After a couple of months into this relationship and one day she asked us to go out for the night somewh... Continue»
Posted by horndogs 3 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 937  |  
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