Shemales Porn Stories
Page 7

Date Coach from sissifyourself


Chapter 1


“So what brings you here today?”
Daniel looked at the date coach. He wasn’t sure of his height, taller than himself for sure, who stood at a paltry 5’ 4”, even though he was already 23 years old. He’d been made fun of his whole life for his height, but he still had a good bit of muscle, and some fat on him, as he weighed about 150 pounds, with nary a hair on his body. The doctor on the other hand, still looked athletic and muscular through his button down shirt, and didn’t look a day over 35. With his short clean cut hair and clean shaven face he could tell this guy was real ... Continue»
Posted by slim_krak 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
1351
  |  
100%
  |  10

The Making of a Sissy - Part Nine

As they sat sipping drinks and discussing what shots would be done indoors or out; Bella’s little cock bulged in her sari as the mature redhead licked her lips as she discussed the ways in which Bella should be trussed, collared and leashed, amongst other things. Sandy stood up suddenly and ran across the patio when she saw a tall figure emerge from the house into the sunlight; this was her Carl. Bella looked on enviously as the two squeezed and kissed at length. She could only dream of being that way with Adam, and so yearned for such a moment with him. Sandy tugged Carl over to the others;... Continue»
Posted by midsummerman 4 years ago  |  Categories: BDSM, Group Sex, Shemales  |  
500
  |  
100%
  |  3

Out of town, I broke free

So I was out of town on business, and I hadn't worn any female cloths out ever in my life, but this time I took some sexy cloths from my roommates girlfriend..and I had been chatting with this transgender girl in the city I was heading to for a few weeks, we would skype and get off together, and she would make me do things to please her..I'm a switch but for this girl I'm her sub slave. When I got to the hotel I took a shower and shaved myself..complete, then I call my Trans friend, for the sake of this story I'll call her Dana, so I called Dana, she told me to get dressed and meet her at this... Continue»
Posted by smonkeys32 4 years ago  |  Categories: Anal, First Time, Shemales  |  
387
  |  
100%
  |  4

The Making of a Sissy - Part Ten

Bella quickly gulped down her vodka and cherry, her bottom tingling with anticipation as her new mature friend gave her a commanding look; she had so enjoyed being submissive for her at the end of a leash, and now she knew she would be bound tightly on a soft inviting bed, and made completely helpless. Her cock stiffened sweetly at the thought; perhaps she would taste the cane again, she would love that. Ellen took Bella’s little hand and squeezed it tightly; though she had only just met this supreme example of a shemale, she knew instinctively she could trust her completely. The redhead smil... Continue»
Posted by midsummerman 4 years ago  |  Categories: Anal, Masturbation, Shemales  |  
550
  |  
100%
  |  4

The Making of a Sissy - Part Eleven

Whilst Bella showered, Ellen and Sandy went down to the poolside to ready some ice and bottles for drinks later; there was Bella’s phone, Ellen tapped in the number to her own phone, and also took down someone else’s number. Ellen smiled wickedly.

“I have a very sweet idea, but I’ll need a week to arrange it; I have to put a proposal to that aunt of hers first. I’ll need your assistance at some point.” Sandy was willing to help out in any way, and the two chatted and giggled as they too went back upstairs to shower and prepare for the evening. Roberts worked swiftly to get the videos and ... Continue»
Posted by midsummerman 4 years ago  |  Categories: Anal, Masturbation, Shemales  |  
474
  |  
100%
  |  2

Meeting a guy from online part #1

I had been talking to a guy Jim online for a few months he was white 47 and we got into some very erotic conversations on line and even had phone sex together a few time then we decided to meet,I was all too excited thinking about seeing him in anticipating what both of us knew what was going to happen.
I got into town showered getting cleaned up putting on a short brown skirt with a white top over my very little panties and padded bra finishing my outfit with a pair of three inch black pumps, looking at myself in the mirror I thought I looked cute thinking he was going to like what he sees... Continue»
Posted by MonicaBond 4 years ago  |  Categories: Gay Male, Shemales  |  
860
  |  
100%
  |  4

Sandy comes to visit me

If you have read any of my prior stories, you know that while I was born as a boy, I more closely resembled my mother and my older s****rs. I was the only boy in our f****y, and from a young age realized that I was destined to live as a girl. It started early in life, with me sneaking into my s****r’s rooms and admiring their pretty things. Later on, I actually began “borrowing” things from each of my s****rs. I lived in secret, ashamed that I was different.

When I graduated from high school, I moved to the big city to attend the University. I was fortunate, as my grandmother loved me dearl... Continue»
Posted by Rickicd 4 years ago  |  Categories: Shemales  |  
1747
  |  
100%
  |  11

Click, click, click....

Click, click, click…the sound of high heels contacting a hard surface has always attracted and aroused me. Whether it’s on tile floors in a hallway, the concrete of a parking ramp or the asphalt of a mall lot, I turn in anticipation to drink in some pleasing eye candy. How short will the skirt be, how long the legs and what manner of hosiery will adorn the object of my desire? Sometimes you can anticipate the leg length by the quickness of the steps, short light steps equal a petite form, slightly slower, paced steps announce a graceful flowing creature.
Click, click, click…today it was an ex... Continue»
Posted by MichelleFaye 4 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
988
  |  
100%
  |  9

My real story



I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him.

It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willing to do anything."

Now what I had written was the following:
"Young 48 year old, looking for an older man, early to mid sixties, still sexually active willing to be my top. Would love to get together and decide what our roles would be and then keep them going whenever we meet. I am a submissive who lo... Continue»
Posted by lookin02 4 years ago  |  Categories: BDSM, Gay Male, Shemales  |  
2176
  |  
100%
  |  16

sissy

He's wearing his favorite outfit. A nylon/spandex blended thong that encased his fullness, shaved and smooth in a delightful caress. A bustier girdle with four straps (he wanted six but the cost was exponentially increased for those two extra straps), and wolford thigh high stockings, his legs and bottom were completely shaved...he was delighted with how feminine he felt, he put her panties over his head. Acetate, full-bottomed, high-cut vanity fairs that bore her scent. His whole outfit was virgin white. He switched on yahoo messenger and put out the open invite.

It takes a while sometimes... Continue»
Posted by pau10s 4 years ago  |  Categories: Masturbation, Shemales  |  
616
  |  
100%
  |  2

Chrissie goes to Camp Pt 1

Since all of my clients are referals many of them know each other and in fact some are very close friends. There is a particular
group of them, four guys to be exact, who arrange a hunting trip each fall. The one guy, Brady, owns some wooded property near the mountains.
The property has a semi rustic three bedroom cabin situated on it. I say semi rustic because it does have
running water, electricity, and propane heat. The hunting trip is usually a one week affair but a few years ago they could only
manage a long weekend trip.
While Brady was in my office one day for his usual "confer... Continue»
Posted by chrissieCD 4 years ago  |  Categories: Anal, Shemales  |  
759
  |  
100%
  |  7

Sissygirls Sweet Adventure

She had spent an eternity with the finishing touches, making herself look as soft and girly as possible, not that she needed to do so. She was as nervous as hell and teetered just a little on the tall black stilettos with silver spikey heels she had waited so long to wear. The walk down the path to the waiting cab seemed three times as long as usual; would the driver think there was anything unusual about the girl who was his latest fare? He smiled warmly and watched the long legs enter his cab.

“Where to Miss?” Sissygirl was wary of speaking for the first time, a little scared that her t... Continue»
Posted by midsummerman 4 years ago  |  Categories: Anal, First Time, Shemales  |  
956
  |  
100%
  |  5

my shemale GF part 2

So today she , her name is Christy, she wanted to do something kinky, very kinky I said that's fine. We cleaned up, she went into her closet, which was filled with dildos, butt plugs, sexy clothing, fleshlights, cock rings, paddles, lube, videos, magazines, bdsm things, and a fuck machine. She came out with this red latex suit on, which exposed her tits, ass, and her sexy 7 inch cock, with red boots that went to that hot cock and a cock ring. She ordered me to get on the bed face up, she sat on my face with her big round ass. I licked her ass for about a minute, she then ordered me to get on ... Continue»
Posted by germanface 4 years ago  |  Categories: Anal, BDSM, Shemales  |  
992
  |  
100%
  |  4

My Addiction

My addiction
Is the sweet syrup
That drips from your dick
It’s like honey,
And the more I taste
The more I wish I could shoot it in my veins
It’s like my liquid cocaine,
Daily doses required to keep me sane…
And I will be your junkie
Just tell me how you want me
Down on my knees begging baby please,
Just let me taste you.
I would do almost anything
To have that every so sweet nectar
Trickle down the back of my throat
As I drain you dry
Nothing compares to the complete embrace
Or look in your eyes when I am pleasing you
This is all I want to do
Make you my 9 to 5,
But I work... Continue»
Posted by Hangdog90 4 years ago  |  Categories: Fetish, Shemales, Voyeur  |  
335
  |  
100%
  |  3

2nd date

So I previously posted a story about my thursday night at the gloryholes at Frenchy's on Polk in San Francisco. I met a gorgeous tranny and we went back to her place for some fun. Well since then we've had lots of fun.

A few days after meeting Bianca I was really wanting a repeat of the fun we had so I gave her a call and she invited me over. It was still kind of early when I got to her place, I was a bit nervous because I didn't know if we could have a repeat of the time before because it was so hot. Well she answered the door dressed in a tiny plaid skirt, white stockings, white shirt w... Continue»
Posted by tat2sf 3 years ago  |  Categories: Fetish, Shemales  |  
1133
  |  
100%
  |  3

Rebecca

I work at a large restaurant chain in their construction division. I spend my time co-ordinating the construction and remodelling of the stores in our chain. Part of my job includes travelling to locations where restaurants are being built, and ensuring that nothing goes wrong.

I was recently in another town, and on my first night in town I hooked up with Chantal, the woman who worked behind the counter. She was an aspiring architect, and so we discussed the construction industry at length over dinner. After dinner, we went back to my hotel, and after some very hot and heavy foreplay, she p... Continue»
Posted by pau10s 3 years ago  |  Categories: Fetish, Shemales  |  
1011
  |  
100%
  |  5

Afternoon's Delight


She stood at the folding table in the apartment's laundry room. She saw him across the room, reading a paper, but not really. She could tell from the glances around the paper every now and then that he was checking her out. She smiled to herself. She enjoyed being checked out, especially by an older guy. She stood five feet six inches, and had rich thick brown hair, with some sun bleaching, lightening it. Right now it was up in a pony tail but unpinned would fall to her lovely tan shoulders. She was wearing a halter top, one of her faves. It accented her full 36C breasts besides exp... Continue»
Posted by sliplover 3 years ago  |  Categories: Fetish, Masturbation, Shemales  |  
478
  |  
100%
  |  7

Becoming Alanna - Part 2

Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work with is there” she laughed looking at my small cock “but also not much to work with in the way of hair". She applied the preheated wax and then the strips to the areas around my cock and my asshole, the area connecting them and lastly my balls. She gently tugged them off and I cried with pain. “Oh shut up s... Continue»
Posted by KristyQuinn 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  
1658
  |  
100%
  |  13

The Football Jock and Chrissie

The Football Jock and Chrissie

Back in college, sharing an apartment with my BFF/roommate Kelly, a lot of my dates and hook-ups were arranged by Kelly. For some reason she always seemed to know just who was into what when it came to sex. She learned a lot about other people’s likes and dislikes from hanging with her lesbian crowd. She was also super inquisitive and fancied herself as somewhat of an amateur detective. I just thought she was nosy.
It was 1998, the middle of our junior year, and I had already been transforming from Christopher to “Chrissie” for 4 ½ years by this time. Needl... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Anal, Shemales  |  
702
  |  
100%
  |  9

TRANSLESBIANS [this is a true story ]

When I first got married in 1992,my exwife,and I were getting along well,everything inbetween,ecept for sex,either I was stressed out from work,or somthing else.well one night we were talking in bed,and were dicussing what we wanted to try out in the bedroom.I'd say well blindfolds,and being tied up sounds nice,or even whipcream,and some type of cream dessert,where we would smear over are bodys and lick it off.but then it happen,I told her that I use to dress in drag,she replied what?she new what I was talking about,and went to raing hell.after a few hours of arguing,she finaly calm down,wasn'... Continue»
Posted by blonde68 3 years ago  |  Categories: Shemales  |  
665
  |  
100%
  |  1