Shemales Porn Stories
Page 78

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 2 months ago  |  Categories: Gay Male, Interracial Sex, 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 2 months ago  |  Categories: Anal, Hardcore, 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 2 months ago  |  Categories: Anal, Hardcore, 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 2 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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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 2 months 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 2 months ago  |  Categories: Hardcore, Shemales, Taboo  |  
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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 2 months ago  |  Categories: First Time, Gay Male, 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 2 months 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 2 months ago  |  Categories: Anal, First Time, 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 2 months ago  |  Categories: Gay Male, Group Sex, 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 2 months ago  |  Categories: Anal, Hardcore, 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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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 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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My First Submissive Experience

I was a dominate most of my life or so I thought. After a great BDSM time with what became my wife we both moved on to different lives. After a couple of tough years I finally met someone who said she shared the same interests that I did. I finally figured out that she was not into the fetish at all but she said she would try the dominant role and see if she enjoyed that. I started to train her on how to be a dominate and at the same time I was collecting some women’s clothes such as a bra and garter belt and fishnet stocking as well as spike heel and a wig. I proceeded to make our bedroom a ... Continue»
Posted by stokes52 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
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Happy Birthday Mike

All characters are 18+

Happy Birthday Mike

Mike cringed as he stood at the cutting board on the kitchen's island counter, his eyes narrowed at his parents, who were standing in the living room, putting on their coats as he chopped carrots.

"Chloe, honey!" Mike's stepmom called out from the living room.

Mike was practically scowling when his older step-s****r Chloe skipped down the stairs and into the room. She was wearing an outfit so typical for her, it was practically her trademark. A simple, pleated maroon skirt hung down to her knees, meeting the white, knitted stockings that w... Continue»
Posted by LordWesley 1 month ago  |  Categories: Anal, Shemales, Taboo  |  
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There Are No Limits, Part 3

"I'm not doing it." Sheridan said. "A thousand times, no!"

The five of us-Me, Sheridan, Bonds, Woodard, and Maurice-were all sitting at a round wooden booth at Kent's Restaurant-not a good idea if you're six cops in good physical condition-discussing Martinez's offer. I rolled my eyes. "Eric, you're being an idiot. Since when do you turn down free sex?" Sheridan's big fist crashed onto the table, but when people looked over at him, he smirked and said "sorry. Roaches." One old woman blanched and turned away, and we turned back inward. Sheridan looked at all of us and said "Look. There's n... Continue»
Posted by asphalt3 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  
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Cumming Home

My name is Joe but I am called Joanne. I am a preop transgender/transvestite but being in the Military I had to be careful not to be caught. Though it is easier now it wasn’t many years ago. I have been taking hormones for 15 years now and have a respectable 38C/D pair of breasts with nice large dark brown nipples which I adore having stroked. I love my wife Sally very much and she has been very supportive. I also have a boyfriend called Bobby – he lives with us now. All 3 of us sl**p in the same huge bed and lovemaking alternates between the three of us.

Ahead of my return from a tour in I... Continue»
Posted by Sally5050 1 month ago  |  Categories: Shemales, Taboo  |  
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Teen Transvestite in Public Loos (1970s) TRUE STOR

A small northern town, on the outskirts of Manchester, this small smokey place was quite unassuming. It’s people went about their daily lives in the normal busy body way. The town had about 50 shops, and the High Street was always quite busy and not like it is today. The small town even boasted a tiny Woolworths store, something that would just not happen these days, but mid 70’s it was commonplace.

On the back of the High Street was a very small and very dated public ‘swimming baths’, and next to this old building was a set of similarly aged public toilets.
The location was super. The sw... Continue»
Posted by SexyTinaTV 1 month ago  |  Categories: First Time, Shemales, Taboo  |  
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From Femboi to faggot Madison

From Boy to faggot sissy Madison

I meet Maddi Ng one night as I was heading back to my hotel form a sales meeting. I noticed this young lady walking down a dark street while being followed and heckled by 4 thug looking guys. I pulled over and asked her if she needed a ride or to use my cell phone, she jumped in so fast I thought she was going to rip the door off my suv. As I drove away I looked over and noticed that she was actually a very feminine boy. I asked “what was going on” and she whispered “I promised to meet those guys for some fun but chickened out”, I asked “why would you want ... Continue»
Posted by BigDaddyJSubStable 1 month ago  |  Categories: Fetish, First Time, Shemales  |  
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