Shemales Porn Stories
Page 57

A night with Louise....a very special "girl&q

Before telling about an evening of 'earthly delights' with a crew member on my boat, I want to say this story is dedicated to a new online friend, Zoe.

As I have mentioned in some of my stories, I owned and operated a 100' charter yacht in Alaska for over 20 years. My target audience could be any race, age, size, or sexual orientation. What they all had in common was they had to have the financial assets to pay top price for a 10-15 day trip with only 12-15 passengers.

One year I needed a crew member immediately and one was hired in Seattle one morning, and that afternoon he was landin... Continue»
Posted by 1kaaboom2 1 year ago  |  Categories: Hardcore, Shemales, Voyeur  |  
  |  7

The guy on the bus

I was not having a good day, my car was in the shop and would not be ready for three days.It was a fouteen mile ride home in the bus. I hadnt been on a bus in twenty years and was not looking forward to the journey. As I made my way to the bus station, I was aware of , a younger woman walking in the same direction. She had a nice ass and wore a shot skirt which showed off her long legs.
There were only a few passengers on the bus so I picked out a seat right at the back so I could stretch out and be comfortable. The same girl got on the bus and sat a couple of rows in f... Continue»
Posted by gjstott 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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An old story of mine but you might enjoy it


I couldn't believe my eyes when I saw the message and telephone number
written on the inside front cover of the book. I smiled as I recalled
the number of times I had idly opened these books in anonymous hotel
rooms on my business trips. It had started three years earlier when I
had joined the sales division for the company I worked for. I was
twenty-three and had never worked in sales before, but I was keen to
succeed in my new role.

I was going to have to adjust to quite a few new lifestyle changes, not
the least of which wou... Continue»
Posted by nikkiesilk 1 year ago  |  Categories: First Time, Shemales  |  

Public Panty Change

Bisexual male - mmm threesome – crossdress - panties – bra

It had been a couple of months since I'd met and dressed up for my sugar daddy. He'd had a lot of money and was willing to buy me any outfit I wanted, along with panties and makeup for the complete girly look. In exchange, of course, I dressed up and provided him with an afternoon of hot sex that had left my little girly hole stretched and aching. So, when he contacted me once more and suggested another day of shopping, I jumped at the opportunity. I made the usual preparations: shaved my girly hole smooth and rinsed myself o... Continue»
Posted by naughty_bi_interest 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  4

Panty Fantasies - Coleen's Magic

Feminization - body change – gender swap - sissy - panties – satin – lingerie – cocksucking

He swallowed hard, his body tense with anticipation and admittedly a small amount of fear. He didn't _really_ know this woman and her beauty was no guarantee of her honesty. He was exposing himself as he had never done before, all in a desperate attempt to capture his dreams, to experience the most intense pleasures.

Looking around the bathroom he saw that it was finely appointed with grey and pink marble and fine Italian tile. The towels were Egyptian and felt wonderful. The whole penth... Continue»
Posted by naughty_bi_interest 1 year ago  |  Categories: First Time, Fetish, Shemales  |  
  |  6

Lesbian Date.

She walked through my door looking nervous, like a first timer. I didn't ask if that was the case. All I tried to do was be myself. I've always been a very welcoming person and this situation was no different.
I offered her a drink as she sat on my sofa knowing full well it normally cuts through the tension and uncertainty from my experience as an e****t.

I poured a drink for both of us and sat next to her offering a comforting smile. I knew she felt uncomfortable as she was in male mode and perhaps felt threatened as I wasn't. "I don't have a male mode" I said jokingly and assured her "I'... Continue»
Posted by Bombshell_TS 1 year ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
  |  3

Back to School

Back To School
Nikkie Silk

I was so excited. This was going to be the first day at my new job. I had recently been appointed as the receptionist and administrative assistant at the local Elementary School. I set the alarm to wake me up early, so that I could get ready and make sure I would be on time. I was excited but also nervous. I had yet to meet my new boss, Mr Michaels, the Principal of the school. I had been hired by his deputy, so I would be meeting him for the first time today.

The State had just enacted an affirmative LGBT action hiring program. This meant that as a pre-op tr... Continue»
Posted by nikkiesilk 1 year ago  |  Categories: Anal, Shemales  |  
  |  20

Crossdresser Dominated For The First Time

Chapter 1: A Couple of Painters

One very long boring day in the middle of summer, i was home all alone, my parents were at work and my siblings out somewhere. I decided it would be a good day to dress up and have fun while i was home alone. I went to my secret stash of clothes i keep in my closet and picked out my purple lingerie. It consisted of a purple and black lace bra with matching thong and garter belt with black stockings. I put it on then went to get my cute blonde shoulder length wig, it fitted nicely as i applied my make up.

Once i looked like a sexy girly slut i... Continue»
Posted by Badassgirl123 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  
  |  15

Daddy at the Truckstop - 1

--This was an encounter that almost happened with a Daddy a while back. We talked about doing this for a first meet to make up for other times that didn't work out, and while talking about it with him was undeniably hot, it ended up not happening for a few reasons, chief among them safety. I think about how hot it would have been to smash a lot of my boundaries this way, though. Enjoy, and comments welcum :) ----

I couldn't believe I agreed to this, but here I was. The truckstop is maybe an hour from my house, and I was pulling into it from the highway now, dressed in stockings, panties... Continue»
Posted by StaceyDeprave 1 year ago  |  Categories: BDSM, Gay Male, Shemales  |  
  |  4


Daddy guided my head with the leash as I sucked him. It had been a while since I had a cock in my mouth, so he only gagged me occasionally to get me used to it. 'Good, Stacey, mmm. You need more practice, but that's why you came today, right?' I could only nod and moan into his cock as he thrust it in again, gagging me. With my hands cuffed and locked behind me, I was helpless to his whims, just as we talked about. It was scary to be tied and exposed like this - dressed like a schoolgirl slut- in the woods next to the truckstop, but it was turning me on so much, too.

I closed my eyes, los... Continue»
Posted by StaceyDeprave 1 year ago  |  Categories: BDSM, Gay Male, Shemales  |  
  |  7

My Ex-Girlfriend's Mom #3

The three of us were laying in Lana's bed, recuperating from an awesome sexual experience. Or at least awesome for me. I could only imagine what kind of sexual experience these two beautiful, busty, extremely hung ladies have had. Lana, the "mother", very sexy for an older woman, with a ten inch cock. And Jill, the "daughter", a knockout in her prime, with a twelve inch cock!

We talked about what we had just done. They told me I was a natural at sucking cock and couldn't believe I had never done it before. But it was true. I told them I had only had sex with real girls before tonight. But f... Continue»
Posted by naughty_bi_interest 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  8

My Ex-Girlfriend's Mom #2

I still couldn't believe all this was happening! I had just met up with my ex girlfriends mom randomly in a bar, found out she had a dick, (a big one at that), came home with her, given my first blowjob, received my first load of cum in my mouth, got caught doing so by my ex girlfriend, and found out she had a dick too! This had been one crazy night, to say the least! And it looked like it was about to get even crazier!

Jill looked amazing. Even better than I remembered. She must have had a boob job, because I remember her only having about a B cup. Now she had to be at least a D cup, proba... Continue»
Posted by naughty_bi_interest 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
  |  6

Wet dream PART 2

Driving to my place it was a conflict, I was totally wet and my companion I bet she was too.

Olga was my co-pilot and could not help to notice that she was day dreaming, I looked at her and under her glasses I saw in her dark sparkling eyes that she wanted something. Her imagination was running wild.

We came to a traffic sign and she in a sudden move got into my crotch, unzipped my pants and let herself into my manhood, moved again my thong and .... I had to go, the light was green, this little brat got me again!!!! We took the highway and she was kissing and pumping me at 90kh.
... Continue»
Posted by ilialenyc 1 year ago  |  Categories: Fetish, First Time, Shemales  |  

Gracie and her best friends son...

Gracie was attending a birthday party at her friend Rachel's house, who's son was turning 18...

"I've known Rachel for more ten years now and she is one of the few type of friends who actually stick around. It felt as if not too long ago I was turning 18, but I was now in my early thirties and Rachel probably felt old too now that she was was nearing forty!... But anyways let's continue with the story...

There was plenty of alcohol available, for those in the appropriate age range of course, and Rachel loved her drinks whenever the occasion called for it. I was the only other f... Continue»
Posted by adblman 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
  |  4

Me Jerking my cock

After a long day at work, I decide to go the local library to study for an exam. I'm already stressed out and I have a huge throbbing bulge in my pants that will not quit.

I'm at the back corner of the library on my laptop away from everyone else. With only a few people there I decide to take a huge risk. Fuck it, there's hardly anyone here and this hard huge lain cock is unrelenting!!

I can not concentrate anymore and I have to release this mind numbing pressure off my cock!! I bust out my headphones and plug them into my laptop. I put one on my ear and leave the other one out so I can... Continue»
Posted by HaloPorn 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
  |  2

Adult Video Store #2

I got up and walked into the next room as she closed the door behind me.

I took a second to look around the room. First I noticed the desk she had been leaning against when she first appeared on the tv screen. Looking to my right, I saw a nice camera on a tripod. Behind it was another desk with more camera equipment and a computer with a large monitor. On the monitor, I could see the room I had just been in. The chair I had been sitting in was clearly visible in the center of the screen. I had a feeling, while I was in the other room, that she was able to see me somehow. Now I knew she had ... Continue»
Posted by naughty_bi_interest 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
  |  4

Yesterday we went shopping...

Yesterday we went shopping.

Master Silk had decided that my undies were dowdy, and my heels not high enough, so we went shopping. Naturally, we shopped in a town not too local to us - we didn't want our cover completely blown! (OK, it was Bath! Lovely tea shops in Bath!)

I wasn't wearing my sissy outfit - I'd not convince anyone! But I was wearing tight jeans to show off my bum, and a girly blouse. A dog collar around my neck was disguised by a pink silk scarf. Our first shop was good old Marks and Spencers, a stalwart of the British high street. M&S may have an old fashioned imag... Continue»
Posted by sissy_jenny 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
  |  1

A Romantic Evening

“I’m pullin’ up,” Nate Jackson said into his smartphone. “You ready?”
“Yes, sir,” replied his roommate.
“Alright then. I’m bout to request the Uber. Just come on out.”
“Okie dokie. See you in a minute.”

Nate parked his 2010 metallic dark blue GMC Sierra 1500 extended cab pick-up in an empty space in front of building 17. He shut off the vehicle and opened the car service app on his phone. After completing the request, he stepped out into the chilly evening air. He grabbed his black faux-leather jacket from the seat and put it on. Underneath, he wore a 3XL navy button down shirt that was ... Continue»
Posted by faggyboi 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  1


It Started With Tattooed Eyeliner

"We settled on black, right?"

"I'll leave it up to you," I said. Lynn began organizing her bottles and
tubes, preparing the ink for the tattoo machine she used for applying
permanent makeup. In this case, she would applying permanent eyeliner to
my upper and lower eyelids.

"Good. Black is basic. Now, we never really settled on what style. There
are a lot of things you can do with eyeliner, and you've specifically
asked that I not take into account your being a male. Is that still what
you want? This is the last chance to change your mind."

"Y... Continue»
Posted by klammer 1 year ago  |  Categories: Fetish, Shemales  |  
  |  1

Good News, Bad News

Good News, Bad News

"Honey, I have wonderful news. I've decided I'm finally ready to have a

I perked up. "That's wonderful!" I said. My wife, Laney, had dragged her
feet on for years ever since we had married eight years earlier. "What
made you decide to do it now?"

"I'm 32, and while my biological clock isn't becoming a big issue yet, I
don't want to get into a situation where it is. So I'm thinking maybe
tonight would be a good time to ... uh ... work on that. How do you feel
about that?" She gave me a sly smile and winked.

"Sounds fantastic. I'll be lookin... Continue»
Posted by klammer 1 year ago  |  Categories: Fetish, First Time, Shemales  |