Shemales Porn Stories
Page 16

Double teamed and a ‘noon delight’


This one had my cleaning woman [at the hostel] rolling her eyes again.

Two foreigners showed up at the hostel about four in the afternoon, this week. They were the typical travelers on bikes; the one bike was in need of some major repairs. After registering them I pointed them in the direction of the local mechanic. They were clean looking guys, in their early thirties, attractive and from Spain. Half an hour later they were back. As I had suspected, the one bike was in bad enough shape that it would be noon or later the next day before it was repaired.

I told them where they could get... Continue»
Posted by swat412 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Dinner time, Cum, from My Man

Ohhhh, Daddy! You are my Man!

You Use me like I'm Your Submissive Bitch, when You show me off, at dinner, with all Your Man Friends!

We arrived at the party and You whispered to me, in my ear, to wait for You, here, outside the Men's bathroom, with my bare arms folded behind my lower back, looking down at the carpet, with my legs close together, just like Your Friends Submissive Girlfriends have to do, till You got done in there. That, I'm to call out for You, if a Man approaches me and touches me.

Some of Your Friends noticed Us arriving and waited for You to go into the bathroom and... Continue»
Posted by SissyCharlie 5 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Donna! You wait for me, here, outside the Men'

Ohhhh, Daddy! You are my Man!

You Use me like I'm Your Submissive Bitch, when You show me off, at dinner, with all Your Man Friends!

We arrived at the party and You whispered to me, in my ear, to wait for You, here, outside the Men's bathroom, with my bare arms folded behind my lower back, looking down at the carpet, with my legs close together, just like Your Friends Submissive Girlfriends have to do, till You got done in there. That, I'm to call out for You, if a Man approaches me and touches me.

Some of Your Friends noticed Us arriving and waited for You to go into the bathroom and... Continue»
Posted by SissyCharlie 5 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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My new assistant - her story, part 3

The next week, Mr. Anderson told me to come to work early on Wednesday. We usually arrive at 8:30 but Mr. Anderson had a meeting at 8:30 and wanted me to help him get ready. I did not realize how heavy traffic is at that time in the morning and I arrived at 7:15. As I entered the office, my boss stood up and walked towards me.

As I rushed in I started my explanation, “I'm sorry I'm late....”

Mr. Anderson put his finger to my lips and quieted my breathless rambling. “One is either on time, or one is late. You are late.” he said sternly.

He took my purse and bag from my hands and set... Continue»
Posted by MassMan669 5 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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Looking a Little Knocked-Up


My one disappointment in life was/is not being able to get pregnant, especially with a few of my black lovers.
As I said in another story and, shared with a few in chat, is that my mother told me (later in life) that she was glad I wasn’t born a girl, ‘You would have been pregnant by the time you were 11 or 12.’ She was right…

We both remembered, when I was eleven years old, me asking her if I could get pregnant. I didn’t ask specifically about ‘me’ but if a guy could get pregnant. I asked her because, I’d recently lost my virginity and Ron was fucking me every chance we had. I was just ... Continue»
Posted by swat412 5 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Bookstore pickup

I'm a regular customer of a local sex store. They sell clothes, toys, etc. They also have a large video rental business. I'm there all the time.

About a year ago, I was in there looking at the transexual and bi videos when I noticed a larger woman standing near me. I took a closer look and realized it she was not a genetic female. She was wearing a red silk blouse, black skirt, stockings and 3" heels. Damn she looked sexy.

I stepped closer and and knelt down to look at the lower racks, but I really wanted a closer look at this sexy lady. She was about my age and clearly comforta... Continue»
Posted by RichVaman 5 months ago  |  Categories: First Time, Shemales  |  
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High School Sissy

Even when growing up I always seem to be on the fem side, my shape
was more of a girls shape then a boys. As I was growing up my parents would
always dress me clothes that were stuff that a boy would wear, because if
they dressed me in something that was sex neutral I be mistaken as a little
girl. As I got a little older I liked being a boy since jerking off was
always fun. But when I was alone I find a way to get into my older s****rs
room and try on here clothes. By the time I was 16 I have to say that there
were times I be able to get dressed in one of her outfits and almost pass
fo... Continue»
Posted by hottniklez 5 months ago  |  Categories: First Time, Group Sex, Shemales  |  
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High School Sissy

Even when growing up I always seem to be on the fem side, my shape
was more of a girls shape then a boys. As I was growing up my parents would
always dress me clothes that were stuff that a boy would wear, because if
they dressed me in something that was sex neutral I be mistaken as a little
girl. As I got a little older I liked being a boy since jerking off was
always fun. But when I was alone I find a way to get into my older s****rs
room and try on here clothes. By the time I was 16 I have to say that there
were times I be able to get dressed in one of her outfits and almost pass
fo... Continue»
Posted by hottniklez 5 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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Becominh sadi

Follow me
Insta@raqm0900
Quemmysissy.tumblr.com

Genre-Fiction, Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity

Introduction:
Cody has a secret...he wishes he were a girl! What will happen when an old f****y friend discovers his secret and is okay with it....really okay with it!
Becoming Sadi

Cody open's his eyes as he awakes, looking around at his familiar surroundings in his bedroom. Band posters, comic books and video games all over the floor.

His parents always gave him crap about the things he liked ... Continue»
Posted by qudduse 5 months ago  |  Categories: First Time, Sex Humor, Shemales  |  
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The walk

Follow.me
Insta. @raqm0900
Quemmysissy.tumblr.com
Introduction:
Ok, so this is a bit of a long intro to the story, and bit romantic and flowery? But its my fantasy so bear with me!
I thought id done a good job, my bits all neatly ‘tucked’ away, (being blessed with a small cock allowed me to push it back and have an almost convincing ‘camel toe’ in my skinny jeans) I was nicely made up, hoop earrings (not too large as to be too tarty) nice bra and panties, DD cup boobs, wearing my favourite brown modestly heeled over the knee boots, tight blue skinny jeans, cream cowl neck pullover and lo... Continue»
Posted by qudduse 5 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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Part three of hotel story

Hotel adventure part 3

7 months after their first accidental meeting. Another meeting had been scheduled for next Thursday and Friday, coincidentally it was with the same company but had a different venue. Namely about 3 miles from the CD in the chat room. As soon as he was alone he sent out to text messages, to the two people he would love to share the evenings with.

The responses he got back were almost instantaneous, both responded yes they would be able to share the evenings. He then started to plan what he would take with him for his alter ego to wear, certainly his female friends... Continue»
Posted by hottvcarole 5 months ago  |  Categories: Group Sex, Shemales  |  
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Meeting Tara.


During a fight with my wife i was so pissed off that i had to go for a walk to the pub, stressed from work and wanting not to talk to anyone i sat at a table and lscrolled some social media pages. Now i am a 6 foot 2 inch 240 pounds of a 32 year old male. I love shemale porn it started with straight anal porn, however that doesn't do it for me anymore. Its shemale or nothing. Since i was going through puberty I would play with my own asshole thinking what all these sexy women felt when they have a cock going inside them. It didnt take me long to realise there is a bit of prep for assplay, an... Continue»
Posted by b84bomber 5 months ago  |  Categories: First Time, Shemales  |  
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The alleyway

She pressed close against his body, so close that he could smell the leather from her jacket. As they walked along, her arm around his waist, he could feel her nails through his shirt gently stroking above his pubic region; with each stroke he felt the bl**d rush towards his cock.

They turned the corner and walked further into the alleyway, him guiding her into the shadows. He looked down at her face, her eyes staring back up at him and what little light there was reflecting off of her lipstick. He slid his hand down her back and slid it under her coat where her could feel her bare back bel... Continue»
Posted by ass_pussy_fucker 5 months ago  |  Categories: Shemales  |  
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Late One Evening

One evening late in the summer ... I had a weekend to myself. After supper I went through I huge ritual including renting a Transsexual DVD at a local Adult store (Strictly Adult) ;) I then returned home and collected my things. I don't have a large cock so I'm able to wear a medium size thong. I finally settled on a pair of black silk with pink roses on them. I feel so much sexier with them on. I used Nair to remove the hair from my legs and under arms. I went with a black garter belt and black stockings. Put on the matching black bra and inserted my breast forms inside. Then I put on a nice... Continue»
Posted by Jasmine_Fire 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Trailer Park Porn Star

As I drove down the dirt road, a thick forrest on my left and farmland as
far as the eye could see, it occurred to me for the first time this might
be a bad idea. Let me explain. I am a young virile male, aged 20,
weighing in at a healthy 185 lbs, 5’11 inches tall, and well muscled to
boot, if I say so myself. It’s not really bragging to say I’m good looking
because I can’t even count the number of women I’ve fucked by now. I guess
you could say I started young (the first girl I fucked was a slutty 15 year
old girl in my middle school when I was only 13). Still, once I got my
first tas... Continue»
Posted by keripinkpanty 5 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Weeks in chastity have changed me ( sissy crossdre

Just wrote this on my blog on accident so uploading again here.
First and foremost thank you to everyone who's given me amazing advice and support. Wouldn't be so confident if it weren't for you folk. At the beginning of May I finally got my first plug and chastity device. I'd been dressing up in girls clothes since I was a k**, and from time to time "experimented" with boys as I got older, dressed in girls clothes. A chastity cage with lock and plug had been long overdue in my arsenal of part time crossdresser, so to say I was excited about them would be an understatement. I quickly took a s... Continue»
Posted by LeeannaCD 5 months ago  |  Categories: Gay Male, Masturbation, Shemales  |  
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Feminization Training - Brat Perversions

Miss Brat needs some diversity today. Her it is a crossdressing day! Her sissy boy is ready and set for some really hard lessons. Let’s call him a “she”. She is excited for the beginning of the session. What do they say? Man in a body of a woman? Whatever, she feels sexy by dressing like a real woman, a slutty woman who seeks for cock and action.
Miss Brat is the right girl for this mission, to train a crossdressing sissy.




Miss Brat gave him some sexy clothes, pretty much a schoolgirl outfit. He went to change and the “she” was ready and willing to do everything that Miss Brat has t... Continue»
Posted by littlemissbrat 5 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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Dear Diary BBC (you will be surprised)

Hi All - If you had read any of my post you would know I kept a diary growing up and who, what I am and what I had to do growing up. Here is a short overview of one of those situations.
My 6th grade teacher (owner) told me one day after school he had arranged for me to meet a few men at the normal road side motel he used to drop me off at to service them many times before.
Sitting on the dirty bed of the run down motel waiting for the door to open to see who I would have to satisfy my mind wondered as always thinking will it be one of the regulars or a new guy.
I snapped out of my deep thou... Continue»
Posted by MichelleSissy14 5 months ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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An unexpected visit from friends

Working from home has its benefits. One of them is I can dress however the fuck I please. Which most of the time means I dress as a woman. On this particular day, it was pretty hot, so I was only wearing stayups, some cute, coral lace - a gift from my wife, and a light summer dress. Messy bun, and light makeup

As I was up in the kitchen making myself a cold drink, I heard my wife coming home from work. What I did not expect was hearing other voices downstairs as well. The voices of a couple we both know. I froze. What the hell was I going to do, cause there was not a chance I could possibly... Continue»
Posted by svgtv 5 months ago  |  Categories: Fetish, Group Sex, Shemales  |  
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Recent invite

He invited me over and asked me how I expected him to look as he answered the door? I knocked on the door and sure enough he was in heels, holdup stockings, a dress that only just covered the lace tops of the stockings, some makeup and a long black wig. I wanted to drop to my knees in the halway and get straight down to it but I resisted temptation as in sure that the sexy one in front of me would want to see me dressed the same. We had a chat and then I was shown through to the bedroom which had 60+ pairs of heels and a wardrobe full of lingerie and dresses. I was told to try on what I wanted... Continue»
Posted by Golum666 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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