Shemales Porn Stories
Page 4

I Knew I Was A Sissy (part VII)

The months to follow were divine.
It was the period of summer holidays. I was living with Morten. I was a full time crossdresser (even if it was at home exclusively). He was treating me like a girl. What else could I ask?
Morten bought me a bunch of clothes, underwear, accessories and make up kits. I had to move my “men” clothes to another room since my closet was full of my new sexy outfits. I was staying home every day and I was enjoying it since I was dressed all the time.
Every morning I was waking him up with a nice blow. His cum was my breakfast! Then, after a shower we would spend ... Continue»
Posted by georgette32hk 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
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an akward encounter

once I made a guy cum like 8 times in one evening/night. he was the dad of my best friend. he was married with 2 k**s, both were in my school it was middle and highschool they were 14 and 18 at the time i was 18 too. i didnt know it was him untill the most akward time possible. he opened the door to the room I was in, there was music going I was about 8 feet from the door, face down with makeup and whiskers and cat nose painted on, furry paws(gloves boots), ass up in the air oiled up, hands spreading it, lights pointed at it, banana barely sticking out all while wearing my skirt and stockings ... Continue»
Posted by carefreeguy 1 month ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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My lovely Miss Elecdtra

I have this dream ,forming in my mind ,I see a beautiful transsexual living in Germany wearing a sexy dark skirt and a tight top matching she has lovely flowing hair and a wonderful smile that seems to light up very brightly when I am talking to her ,I am her friend a tall well endowed ultra busty Cross dresser ,Elecdtra makes Angel's panties get very full & tight with excitement when I think of holding her in my arms ,I stand in front of my floor to ceiling mirror daydreaming of her I look at my self in the mirror wearing my biggest bra a huge NNN cup custom made to hold my custom extra super... Continue»
Posted by brabuster_cd 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  
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WHY I BECAME A COCK SUCKING SLUT AN LOVE IT Part

As I lay'd on the bed next to Mike, his cock in my hand and the taste of his cum still in my mouth, I knew I needed more, i rolled over laying next to him ,my stocking cover'd leg over his, the feeling of it sliding over him,as I moved up and down the rush was new and exciting. I could feel Mikes cock becoming full and heavy ,the look on his face told me he was enjoying it,so I rolled over on top of him and began slowly sliding over his body, I could feel his cock rubbing against my panties so I slowly began to lightly grind on him,I felt him getting harder as... Continue»
Posted by geoff19 1 month ago  |  Categories: Gay Male, Masturbation, Shemales  |  
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WHY I BECAME A COCK SUCKING CD AN LOVE IT

I KNEW I was gay at an early age, all through school I only had a few friends that I spent time with, it was the same in high school, I wasn't a jock and really didn't bother with many of the girls, the friends I had ,well we spent alot of time playing video games after school. Thats how I started dressing , Ken and I were at his house playing games in his basement room and I needed the bathroom, I went upstairs as he played, and as I went down the hall I passed his moms bedroom,looking in I noticed an open draw in the dresser, and I got this strong urge to go in. Knowing it w... Continue»
Posted by geoff19 1 month ago  |  Categories: Gay Male, Masturbation, Shemales  |  
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Sissy Slave

Joanne, my wife, has for many years insisted that I wear lingerie and girly things under my male clothes when at work as part of my sissy training. At home I am a sissy slave.
“Sally” she said “Today we are going to make you feel more aware of the pretty things you wear”. After years of taking hormones my breasts are a nice 38C with dark brown shades round my nipples and Joanne had arranged for me have my balls and sac removed when we went to Thailand one year. Despite this and though my cock is now very small it can still shoot lots of cum which I am often given on my cereal for breakfast. ... Continue»
Posted by Sally5050 1 month ago  |  Categories: Fetish, Shemales  |  
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My first time with a guy part 2

As you will recall from reading part 1, I had just agreed to go up to a guys flat, situated above a' private' shop in Leeds. The shop assistant had just told me to select some sexy underwear from the shop to wear as I experienced my first taste of gay sex.

The lingerie in display was probably the best thing on sale in to shop, for a crossdresser it was heaven but I wasn't sure what to choose. There was school girl uniforms, French maid outfits, nurses uniforms, baby dolls, body stockings, I just didn't know what I wanted to wear. I finally decided on a pretty pink baby doll, it was very lac... Continue»
Posted by LeedsXdresser 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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The Life Class

It wasn’t something I’d ever consider doing, but I was in need of some extra cash as I’d not been asked to do any porn shoots for a while. So when a friend told me that a local art group were looking for models for their life drawing class I decided I’d get in touch to see if they’d have me.

I went along to see the teacher, a middle-aged guy who was Professor of Fine Art at the local college and ran evening classes for amateur artists. I arrived dressed casual, jeans and a tee shirt, my long hair tied back, little make-up, pretty androgynous, but my growing boobies were fairly obvious under... Continue»
Posted by mica_d 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  
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Megan sissy sauna gangbang.

I had just moved to london for uni and was really excited to get a chance to try out some of the bigger gay saunas and sex clubs.
I had spent the whole night before fucking myself with a dildo I had bought from a soho sex shop, wearing lingerie i had stolen from the halls wash room .A stripped thing with lace trim and black lace bra. I still had my fishnets and i had shaved my whole body, so i was feeling really girly.
The next morning i got up early and spend the first couple of hours of the day in the shower,slowly fucking myself with my dildo, sucking it then sliding it inside myself to... Continue»
Posted by hardcoresissy 1 month ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Moving in with Jim and Candy - Part 2

"A taste of Candy" - Fiction

Jimmy smiled at Candy and said, "I think you should show him your secret, Candy."

Candy smiled wickedly, "I think you're right."

With that, she hooked her thumbs into the edge of her bikini bottoms and slid them down. She the reached between her legs and rubbed from her ass all the way forward, and her surprise flipped out. She had a cock! Candy was a hot, busty TGirl! She was definitely getting hard looking at us. Her cock was slightly shorter than mine, but was thicker at the base and had a tapered tip. Now the reason for them not getting married was a... Continue»
Posted by Mrtommyboy 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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Moving in with Jim and Candy - Part 3

Learning how to take anal play - Fiction

So the next couple of weeks with Jim and Candy revolved around us having various types of sex. Sometimes all three of us, sometimes just two of us. Sometimes two of us having sex while the third masturbated, sometimes all of us masturbating and watching each other. It was fun and hot. The one thing we hadn't done was me taking a cock in my ass, whether it was Jim or Candy. I guess the part of me that was scared was stronger than the part of me that was curious.

One day while I was working in the store, I had an older gentleman ask me for some "Pop... Continue»
Posted by Mrtommyboy 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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Fantasy

It certainly wasn't the cleanest of toilets, The smell of stale piss and God knows what else hit me as I opened the door, once inside I have the seat of the toilet a quick wipe and sat down I looked at the No smoking sign. like I'm really going to follow that rule.
As I smoked a cigarette sitting there in the dim light of the dirty toilet I was wondering what could happen and hoping it would come true.
Let me tell you what I'm wearing, I'm dressed tracksuit bottoms and a fleece top well I was when I first came into the toilet, i'm now sitting on a dirty toilet in a silk blouse a padded ... Continue»
Posted by dog9335 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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A New Waitress in Town

THE NEW WAITRESS
Moving to a new community is always difficult, especially when you're alone, with no friends or relatives to turn to. The advantage though is that you can be anyone you want.

My name is Robin and I recently graduated from a Boston University, where my f****y has lived since coming to the US from Ireland. I was only two years old when we came here and have no recollection of Ireland at all. I was very settled in Boston, a good school, swimming competitively on the school team, an excellent job as a waiter at an upscale restaurant, girls, you name it. Things were about to ... Continue»
Posted by qudduse 1 month ago  |  Categories: Hardcore, Shemales, Taboo  |  
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My first experience with a guy part 1

At 18 I was popular with the ladies, good looking, good body and a a nice big cock that was constantly hard. I had a beautiful girlfriend and could have had any girl I wanted. Unbeknown to her and my friends, I was a closet crossdresser, a sissy who fantasised about dressing up and sl**ping with guys. It was a confusing time for me, I was almost certain I was straight but part of me craved cock, especially when I was crossdressed. I would dress all sexy in my own underwear and s****rs clothes (I was lucky to have an older s****r so access to a full wardrobe) and play with myself until my cock ... Continue»
Posted by LeedsXdresser 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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I Knew I Was A Sissy (part VI second half)

Me and Morten kept seeing each other for the next days. We would mainly meet at bars and encounter at hotels. I avoided asking him over my place as I hadn’t yet confessed about my crossdressing habits and I was not sure how he would react. My previous experiences were not the most positive ones and if he was to come in a house and see my wardrobe he would be surprised at least. I was having a good time but I wanted more, most important I wanted to be able to express myself while I was with him. I could understand that as time was passing by it would be more difficult to tell him and for sure i... Continue»
Posted by georgette32hk 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
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Office fantasies

This story is about a fantasy I had at work, thinking about
an amazing and gorgeous gurl whose name is Lolit*25
.
.
.
Today at work I was participating in a really boring meeting.
Luckily the meeting room was big and I was at the end of the room.
Lights were soft because a supplier was projecting some usless shit.

At some point you came into my mind.
Your pictures... your face... your body...your cock...and in a heartbeat I was so hard!
I started daydreaming that you were a colleague, and there you are... sit in the chair next to me

You have a hot makeup. Light eyeshadow, lon... Continue»
Posted by sukor 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  
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Gangbang at Ricks part 4



Gangbang at Ricks part 4

I got my C/D Sissy, BB bubblebutt tag teamed at my daddy's place. yes there was 9 big cocks, nothing under 7", Daddy Rick was needed a slut, party with his horny poker pals, was going to pay a hot cutie, it was a close friends daughter, found out later. 200 bucks + tips, Rick called me to help him out ASAP, get Dressed be ready to play the whole weekend. Well here is how fun we had un... Continue»
Posted by mrheat22 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  
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I Knew I Was A Sissy (Part VI and half)

I started dressing full time at home. The minute I would return I would immediately take off my clothes and transform in a girl. Men clothes became my outfit for my day life. Each time I was dressed my sexual desire was increasing immediately; I wanted to get fucked hard, I wanted to suck cocks. Unlike when dressed in man’s clothes. None of my classmates ever thought I was a sissy, very few considered me as gay. It was strange to them that I didn’t had a girlfriend but as I was staring all the time at them they were not suspicious. They just thought I was shy on approaching them. What they did... Continue»
Posted by georgette32hk 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
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The Business Trip - Part Two

Continued from Part One http://xhamster.com/user/mica_d/posts/517581.html

I really was lost for words. My boss had never come on to me at work and here she was suggesting we share a bed!
Are you sure about this?” I said, rather meekly.
Of course, if I wasn’t I would not have invited you along, nor would I have cancelled your room.

At that moment the coffee arrived. It gave me a few moments to reflect on what was happening. Here I was in a luxury hotel, with a woman I hardly knew outside of work, and was being tricked into sharing a room, a bed - and w... Continue»
Posted by mica_d 1 month ago  |  Categories: Anal, Shemales  |  
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The Making of a Sissy (Part 5: Boys Will Be Girls)

Struggling to keep my eyes open, I stirred my spoon around in my cereal slowly as if I were hesitating to get on with the day. In a way I was procrastinating. My mom had just woken me up to remind me that it was Friday, and this was the weekend I was supposed to go stay with my dad. Since their divorce, I only saw him for one weekend out of every month, which for me was more than enough. Don't get me wrong, it wasn't that I didn't like my father, I just struggled to keep myself entertained when I went to visit. As I sat on the stool in the kitchen, my aching sissy hole reminded me of how ... Continue»
Posted by briantid8 1 month ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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