Shemales Porn Stories
Page 13

My dream to be a d**g house whore

Who I want to be
Look I am not like your typical gurl. I am well educated from a good home and I have a great practice. I am clean disease free and always smell nice. I have always been a sex addict since I was little. As I got older my tastes got kinkier and kinkier. I have now been a submissive since my teen years and I just came to the extreme side of that. It all started a year ago when I started seeing a new mistress. She was into feminization so she started dressing me. I liked it ok as she would use dildos on me but what I really liked was being called names and made to go out in publi... Continue»
Posted by dncn31 4 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Choosing An Outfit.

Tammy was my next door neighbour when I grew up. We went to school together and were very good friends. She was beautiful, athletic and great natured, and would have been the perfect girl for me or indeed any guy. Alan was the son of my mums best friend, six months older than me so like Tammy we were at school together and because of our mums, we saw a lot of each other out of school too. Alan's parents had split up so he spent some weekends with his dad who was a big fan of the outdoors, so we often were out with him, camping, fishing and boating when Alan was at his dad's.

As we went into... Continue»
Posted by JemC 4 months ago  |  Categories: Gay Male, Shemales  |  
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Meeting Tara again

For a few weeks i replayed the night i had spend with Tara over and over in my head, each time i would get a hard and get super horny, to the point that i would jerk off 3 maybe 4 times a day. I practically lost interest in all porn other than shemale sections. My knowledge grew as did my interest. Tara the sexy trans woman of my dreams has sent me down the rabit hole. I am waiting to find out how deep it will go.
As i mentioned previously i am a tall guy 32years old with 240 pounds to my frame. I have an 8 inch cock and i am in love with trans women. I had been txting Tara and flirting with ... Continue»
Posted by b84bomber 4 months ago  |  Categories: First Time, Shemales  |  
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My first time with a shemale

OK, I was wasting my time on shamble videos and pictures on the web for about 8 years! When I first entered a porn site I almost got sick, but soon I got really curious about it but didn't dare to click that button; couldn't explain why I wanted it so much though. Eventually I pressed it. I started with shambles alone, then shambles fucking girls, then shambles fucking shemales and end up with shemales fucking guys... I started loving it, watching it on a daily basis. My fetish for thong tanlines was covered also, so I became addicted to shamble porn.

Eventually I watched so much shemale po... Continue»
Posted by lokojoro 4 months ago  |  Categories: Shemales  |  
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White Sissy, Chocolate City

This northeastern city was a world away from the two stoplight Oklahoma town where Bon-bon had grown up. The population in this metro area was a little over four million while his hometown could boast no more than three thousand residents. Back in the O.K. state, there were no Black residents, here almost half of the folks were Black. It would have been a culture shock for most people, but the O.S.U. Cowboys fan embraced it.

Bon-bon’s government name was Andrew Conway. He had recently celebrated his twentieth birthday after having moved to the city just eight months ago. He had attended cl... Continue»
Posted by faggyboi 4 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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The return of Sir Roger


** This was written as a follow-up to another story – which was a memory of some of my time living on St. Croix. I was in my mid-twenties then, lived there for five years and, mostly slutted around or, made money by being a TS prostitute.


A few weeks later, on a beautiful Sunday morning, the girls and I were having a late breakfast on the veranda of the good old King Christian. Molly was sitting directly opposite me at the table. Suddenly, she looked up, directly behind me, gave a twisted little smile and said, “Ut oh sis…here comes your boss man!” before I could react to her rem... Continue»
Posted by swat412 4 months ago  |  Categories: Anal, BDSM, Shemales  |  
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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 4 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 4 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 4 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 4 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 4 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 4 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 4 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 4 months ago  |  Categories: Gay Male, Hardcore, 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 4 months ago  |  Categories: Fetish, 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 4 months ago  |  Categories: First Time, Sex Humor, 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 4 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 4 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 4 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 4 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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