Shemales Porn Stories
Page 69

Brian My Cruel Master

Brian my cruel master

*note this is fiction based loosely on fact


I met Brian early one Spring evening when I was 20.
I was out for a walk, no job, no school, just aimlessly
walking about.
He was standing there on the sidewalk of the
pleasant, tree lined neighborhood with a younger friend
so I walked up to them and introduced myself.
Hell, I had just moved into the area, I was bored and lonely
and wanted to make a buddy or two, nothing more.
The conversation went something like, “I live the next
town over and I saw you standing here and figured,
what the heck, you look l
... Continue»
Posted by yutubeslut 9 months ago  |  Categories: Anal, Hardcore, Shemales  |  
390
  |  
100%
  |  2

Chubby legal male hooker

I guess one day somebody figured out that if it was legal to pay people to make porn, but not just to have sex, that the easiest way to 'legalize' prostitution was to have a camera running or take at least one picture at some point during the act. Since I am interested in all sorts of men this seemed like an idea with potential.

I started posting on all the free bulletin boards about my new 'business', Versatile Services. Catering to discerning gentlemen it would provide playful companionship and diligent attention. How do you like it? Perverted married guy who likes 69ing with chubby m... Continue»
Posted by cumquarts 9 months ago  |  Categories: Fetish, Shemales, Taboo  |  
733
  |  
100%
  |  3

My Next Meeting with Master part 1

One day I received a text message from my Master, who had asked if I would be free in a week and half time, I text back to say yea I would be free and then he said good and asked if I would be free for at least two days. I replayed saying yes I would be free. So we had arranged to meet at his place at 830pm. He asked that I would bring with me the straight jacket, all my hoods, mitts, collar, whip and brand new padlocks that were still in a sealed case for him to open when I get there. Also that I need to wear my mini dress that is wet look and boots.
I could not wait for this day to come as ... Continue»
Posted by dallasrose 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
991
  |  
100%
  |  2

Last weekend

I had arranged a meeting with a new gentleman lover.

I was excited about being naughty.

Knowing I was going to fulfill my craving with a big new cock to play with made me bulge in my panties as I drove to his place.

I arrived at my new friends place a little early.

He answered the door in a dark Tshirt and jeans that hugged him in all the right places.

There was a little chit chat, but we both knew what we wanted. He wanted to fuck me and I wanted to feel a hard cock fill me with cum.so why delay the fun!

After kissing me, his hands found my tits and pinched my nipples. ... Continue»
Posted by lornasababe69 9 months ago  |  Categories: Anal, Mature, Shemales  |  
1492
  |  
100%
  |  7

....just me being a slut

I whimper and moan with lust as your fat veiny cock slides in and out of my well trained slutwife asspussy.
i push my ass out to get as much of you into me as i possibly can, my cunt wants your whole cock.
you slap my ass with a loud smack "you lovely little whore, you cant get enough of my cock, can you?" you laugh while manhandling my body "NO, I want your cock all the time" I gasp from your hard and deep thrusts "I need to be filled all the time!" you yank my head back even further shove 3 fingers into my mouth and hold my mouth open not missing a beat plunging deep into my bowels. Your ... Continue»
Posted by bimbodollval 9 months ago  |  Categories: Anal, Hardcore, Shemales  |  
2147
  |  
100%
  |  1

Happy Trails

Once every so often, I go out of town to indulge in my crossdressing fetish. Nothing too fancy, just a reasonable motel within an hour drive. Just far enough away from the daily personal and professional grind.
Most of the time, this involves me playing dress up in the room and satisfying myself with my toys. Over time this has gradually progressed to a point where I have gone outdoors dressed up. The most recent event involved me enjoying a quick late evening dip in the hotel hot tub.
My most recent excursion was a step further for me. About a 10 minute drive from the hotel is a mixed use... Continue»
Posted by nikki_toyz 9 months ago  |  Categories: Masturbation, Shemales  |  
3282
  |  
100%
  |  7

The real me..

Finding the real me



I live in Perth, Western Australia and go to a place called Perth Steam
Works. It's a small building down a side street and not much to look at.
It's a place where Gay men can go, it's clean, discreet and unobtrusive.
I don't consider myself gay as I have no interest in men that is until I
am dressed. Is this the same for all like us?

I have been there a few times with the sole purpose of getting it off
with men. Normally I take all my gear with me in a bag and change there
but it's difficult because there are no changing rooms, or none that I
have seen, an... Continue»
Posted by klammer 9 months ago  |  Categories: Anal, BDSM, Shemales  |  
652
  |  
100%
  |  1

Made me a woman pt.2: Degradation

I'm regaining my senses... im on my back, in my bed, im naked, i feel an around me, and heavy breathing next to me. My big black man was sweating and panting. im sweating, my body is shivering, and my ass is raw and leaking out his cum. His hands start running all over my body groping my tit, rubbing my phat ass. i can feel myself getting excited again and getting hard. he notices that so he spits in his hand and grabs me by the crotch. again his massive hand completely takes me and he starts rubbing me. i start moaning and gyrating my hips on his hand. he leans over and whispers in my ear "yo... Continue»
Posted by alexismorel 9 months ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
1628
  |  
100%
  |  1

Introducing Jessica

Say hello to Jessica, she's 19 (at the time of this story) and very friendly.

The name I chose when becoming more and more of a sissy.

It was a quiet weeknight, and I was alone at home. Fresh out of the shower and sitting naked at my computer, online and chatting to lots of horny people.

After a while of chatting a while, some private chats were going on and getting hot and heavy. Some with new people, some with same people I've chatted before.

In this instance was someone I'd chatted to many times, henceforth known as John. We chatted often and about many topics, but mostly about ... Continue»
Posted by Want2BeTrans 9 months ago  |  Categories: First Time, Shemales  |  
2266
  |  
100%
  |  10

Meeting Mr Mac Muffin

Meeting Mr Mac-Muffin

Now it was like 11.30 pm Saturday night when I had finish work and was one my way home when i saw my old gurlfriend Loraine at the bus stop. Its like two years since we last saw each other so i figure hell why not an the bus would leave the terminal an 12 sharp . Since I always have a stash of clothes in the car, I pull into a park an pull out my girl clothes.
In less that 10 minutes I was a girl, my brunet wig was a little ruffle an some red lip stick made up my face . My homemade breast and pussy with my black lace panties took care of m... Continue»
Posted by hellpuss 9 months ago  |  Categories: Anal, First Time, Shemales  |  
1144
  |  
100%
  |  2

The Club and The Morning After

As we were leaving for the club I couldn't help but notice how sexy Linda and Kathy were dressed. Kathy was wearing a short black dress that seemed molded to her figure and nearly exposed her ass it was so short. Linda had on a pink, glittery looking dress that was flowing, short but not as short as Kathy's dress. Linda's nipples were visibly hard and both ladies were wearing high heels.

When we arrived at the club the doorman greeted Linda and Kathy like old friends, hugging and kissing both, then nodding to me and Henry. One could hear the music outside, but when the doorman opened the do... Continue»
Posted by trisexual69lvbbc 9 months ago  |  Categories: Fetish, Group Sex, Shemales  |  
1950
  |  
100%
  |  5

my 2015 dr visit

Every year I have my annual Dr's appointment and it seems it is getting a little different each year. like in the past years I've been seeing the same Dr. and nurse. I make my appointment and as usual I show up wearing panties and a a/b size bra. I only own panties and since they have seen me in them in previous years it is no big deal. I do wear pretty panties with lace around the waist and leg bands.

When I was called back by the nurse as usual she had me take off my shorts and top and put on a gown and commented on my pretty bra and panties and told me to keep them on since they were... Continue»
Posted by sissygirl 9 months ago  |  Categories: Gay Male, Shemales  |  
3300
  |  
100%
  |  3

My introduction and first "real" meet

Well to start off, I’m 6’, good looking, masculine and athletic, 40yoa. I’m very much opened minded and I use to dress some few years ago. I got married and it pretty much had to stay a secret. When I did dress, I dressed fully and was quite passable. It was a shame I had to get rid of all the sexy lingerie, heels, stockings, make-up and wigs. Yeah I threw a lot of stuff away knowing if I got caught it was over but now I don’t have that worry anymore. Thank goodness that relationship ended, but it was for the good. I met a few cross dressers, before the marriage, from the Colorado Springs and ... Continue»
Posted by stormietv 9 months ago  |  Categories: Fetish, First Time, Shemales  |  
2334
  |  
100%
  |  10

Gender bent – The ultimatum

Gender bent – The ultimatum

I Stared at my phones screen as I watched a video on me getting fucked not even 24 hours ago. I was angry. How could they do this? Why? I needed answers and fast. What if someone would recognize me? I would be ruined. I paused the video and look at who posted it. The user was called “The Feminizer” and private account meant I couldn’t even look at his pictures or his bio. All I could do is leave a message which I did. “Dave. Dude what the hell. This is Nick the one getting fucked by you. PLEASE TAKE THIS OFF NOW” And pressed the button to send. I then reported t... Continue»
Posted by youngprboi 9 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
983
  |  
100%
  |  2

Gender bent – Dolled up party girl

Gender bent – Dolled up party girl

“Welcome everyone, Thank you for coming out. I know you see a ton of new faces and a bunch of old ones but this is a fun party were we come to enjoy ourselves” The man said. He was a heavy set guy. Naked as per the rules for all men that attended that party, which was a few. “Ok now the rules. New sluts and drink girls are off limits unless they give you the green light, other than that if they are fucking they are open for play.” He chuckled out. “But first let me introduce some of the new girls.” He started calling out girls by their names, stating how ... Continue»
Posted by youngprboi 9 months ago  |  Categories: Fetish, Group Sex, Shemales  |  
790
  |  
100%
  |  1

Gender bent – a Mistake

Gender bent – a Mistake

I was dressed like a bimbo, my lips plumped up from sucking on shot glasses, Pink latex, Trashy fake tattoos of my back saying fill me and a black ace of spade on my ass cheek and Sissy clit on my pelvic area near my dick, My tits was pierced for this party and I had a Cumslut collar on my neck. 8 Inch thigh high pink latex and anime pink wig to make me look like a candy slut. It was either this or complete shaming of me to the point where my life was ruined. All I needed to do was be dressed like this and serve drinks and I just served my last one after Kandi took i... Continue»
Posted by youngprboi 9 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
1494
  |  
100%
  |  2

Gender bent – Ch 7 -The Gang-bang room

Gender bent – Ch 7 -The gang-bang room

Hey all. Thanks for reading my stories and all. I want to say if you enjoy them. Leave comments and let me know if there is something you would want to see. Sorry about the errors in advance. Also if you haven’t already noticed the stories are kind of out of order (Sorry) I took it upon myself to make this Table of contents as I will be numbering these stories from now on. I expect to get to chapter 12-15 and going to wrap this one up hopefully by the end of the month “Fingers crosses”. I do this for fun, so leave a comment and let me know what you th... Continue»
Posted by youngprboi 9 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
1121
  |  
100%
  |  2

A moment in Taos

I recall another meet I had with another dresser who happened to live in Taos NM. Again I met her on-line and after exchanging a few e-mails we planned to meet. At that point in time I was like an hour and a half away from there. She offered to meet at her place and she told me to text her when I got closer. But I had somewhat of a dilemma. Since the drive was going to take a while, I was debating whether I should dress first or find a place closer to change. I’ve only been to Taos like one other time so I wouldn’t know of a place to change in a hurry and wasn’t going to stop at some gas stati... Continue»
Posted by stormietv 9 months ago  |  Categories: Fetish, First Time, Shemales  |  
385
  |  
100%
  |  1

Trans girls first public sex with a stranger

I just had an amazing, and accidental public sex experience.

I was traveling home from an out of state Thanksgiving weekend with friends, and I had to go to the bathroom. So I pulled off the highway.

I always hate public bathrooms because they are usually dirty. So I found a pull-off on the side of the road next to a swimming area. It was just about to get dark so I decided to get out of the car quick and scurry into the woods. There were two other cars parked there with people just loitering, but I made little notice.

There were a few footpaths through the woods that led down to the... Continue»
Posted by SissyAtHeart 9 months ago  |  Categories: First Time, Shemales, Voyeur  |  
3469
  |  
100%
  |  14

Made me a woman pt.3: Swallowing my pride

I'm standing still frozen. After getting fucked, bred, degraded and then receiving slutty clothes, heels and jewelry by this big black man. He brought on three of his friends,equally as black and as big with muscles sitting on the couch eye fucking the shit outta me. I just walked outta the shower mmy long blod hair is did, my face looks extra whore-y. dark eye makeup, red lips and all. wearing a gstring and bra matching set. purple with black strings. a mini pink fishnet dress. a pair of 6 inch clear heels and an ankle bracelet with an engram an ace of spades. the clothes, heels, and jewelry ... Continue»
Posted by alexismorel 9 months ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
3142
  |  
100%
  |  1