Shemales Porn Stories
Page 64

Daddys whore


I had always been fascinated by the feel of womens clothes against my skin, and today was no different. Mom was away on a business trip to Canada, and dad was away at work for the next couple of hours.

I had always had an effeminate look to me, with me being 6’1” and thin as a twig at 19, I was scrawny. I had bought a black wig to go with the outfit that I had picked out. It was black 6” heels, black pantyhose, a black garter belt and panties, with a short black skirt and a little black tube top. I was hard just thinking about what I would look like.

I took a shower and completely shav... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 1540  |  
100%
  |  3

Halloween Pt3

My enthusiasm waivered a little once his crotch was in my face. I could see his cock straining against his sweat pants. But, I considered the alternatives: He was horny, and he was expecting relief. We were in his frat house. And he was much bigger than I was. And, I was dressed like a young woman hot for the D. If I told him no, he could easily beat the shit out of me. And then tell everyone he was fooled. God knows what his frat b*****rs would do.

Besides, he'd sucked my cock. How bad could it be? Women liked giving blow jobs, and obviously some guys did too. It's not like anyo... Continue»
Posted by TransContinental 9 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1540  |  
100%
  |  4

A night to remember with G/F and a sweet little tr

At 52 years old i have had a extensive sex life. I have always been impressed by and i will use several words to describe Shemales, trans, Gurl, Traps, cross-dressers. I guess I like the fact that they take some time to look and or change into a better person and going from male to female can take some time and tricks.

Boston MA 1997: My G/F and I decided to add some spice to out very adventurous sex life. We went out one night to a alternative club that had a fashion show. Most will call it a drag show, this was a little slice of heaven for her. She played with my cock through my pants as ... Continue»
Posted by wankingamerica 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 1539  |  
63%

Delilah and the Deep Blue Sea. (Part One.)



This story has taken me forty years to tell and I only finally relate it now in the firm conviction that nobody will believe a single word of it. In many respects that doesn’t concern me. I have other motives than those of persuading the reader of the veracity of my tale. I write it more to exorcise a ghost that has haunted me for most of my adult life and will doubtless continue to do so for the rest of my days. It is a story, the memory of which, has been my constant companion these past forty years and has dominated my life in the sense that everything I am today has been shaped by tho... Continue»
Posted by Mikebasil 3 years ago  |  Categories: BDSM, Lesbian Sex, Shemales  |  Views: 1543  |  
91%
  |  21

Tgirl fun

Because it was a little cold I went out dressed in a nice pair of tailored jeans, which show of my bum beautifully, black bra, lacy top and a really tarty shimmering jacket. I was wearing a lovely pair of ankle boots and was able to quickly slip out the front door of my house and into my car. It felt wonderful to be dressed up and driving through the rainy streets. People were able to look at me when I stopped at traffic lights but no one seemed to notice anything amiss. I wasn't able to park too close to Mandy's flat so had a longish walk before I got to her front door. I loved the sound of m... Continue»
Posted by TaniaHarvey 4 years ago  |  Categories: Anal, Shemales  |  Views: 1537  |  
80%
  |  4

Transsexual Son Daughter

Now I’m a 51 year old mother of one and watching my Daughter who’d been once my son putting on that very nice silk blue bra from Harrods department store and lift up her huge breast in to them made me so wet. Now seeing my son all now transformed and transitioned in to a beautiful woman but she’d still had got her manly bits now that didn’t harm anyone but boy did she look awesome and lovely all 5’9 of her slim size 10 with her rather large 46DDs which shed always wanted and her slim lines like a guy would say about a classic sports car.

Now as I was saying I am a 51yr with a son that had b... Continue»
Posted by 1superhornyguy 1 year ago  |  Categories: First Time, Mature, Shemales  |  Views: 1537  |  
71%

My life at home.

This is a purely fictional story, and in no way reflects real events.


My name is Greg, I am 47, 5'11", 225lbs, and a widower. My wife died shortly after c***d birth. She was on her way to the store, when a stolen truck, driven by a man wanted by the police. She left me to raise our son, terry. for the last 16 years, I have been mother, and father to him, watching him grow from a little boy, to a young man.

Terry was never into sports, just accademics, and these he excelled at. He was never muscular, kind of thin, graceful. I work as a product designer for a multi-national com... Continue»
Posted by chefjohn2112 4 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 1536  |  
100%
  |  4

my fantasy part I

I've always been interested in being a prostitute but never had the guts! This is what I would do if given the opportunity!!

It was another morning alone in my dump of a one bedroom apartment. Sexy shemale porn playing on my laptop and me performing my usual morning edging session!! I was strolling the web and came across some pictures of sexy crossdressers hooking on the streets! This made me want to cum so bad but I couldn't because I was edging and it felt to good when I stopped myself from cuming. I usually edge for an hour or two until I get so much precum my hand is sliding up and do... Continue»
Posted by nebraskasissypussy 1 month ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1541  |  
100%
  |  3

End of the Week

Ernest Gaines, known by most as ‘E’ or ‘Big’, bounded down the corridors of Presbyterian Regional Medical Center wheeling a patient towards discharge. It was shortly before 8:00 a.m. on Saturday which meant this was his final task of his shift. He made it to the waiting area and brought the chair to a stop as the elderly man peered out the window for his f****y.

“What’s going on,” a fellow orderly asked.
“Can’t call it,” E replied.
“I hear ya, man. You gettin’ off soon?”
“Yeah. Goin’ to the crib and chill. Got three in a row off.”
“I’d do that. But I got too many people at home to get a... Continue»
Posted by faggyboi 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1536  |  
100%
  |  2

Interstate Reas Area Whore

Driving down the interstate the sign said Rest Area one mile. My heart skipped a beat and there was slight stiffing of my male meat in anticipation of events to unfold. This interstate rest area was always packed full of eighteen wheelers as many as forty. Surely one or two of these truck drivers would be horny enough to over look the fact that this slut had a little something extra a top her nylon covered legs.
I had a black merry widow corset on that pulled my waist in a nice four inches. Eight garters held up my coffee colored FF nylons. I had on five inch red stiletto pumps. My bla... Continue»
Posted by littleoralvee 3 years ago  |  Categories: Shemales  |  Views: 1532  |  
100%
  |  10

LOVE

I was work as a counselor for people with gender identification. One day a beautiful lady, Pham, approached me for an assignment related to her doctoral work at an university nearby. Her work was related with gender identification issues.

Our scientific bent of mind and approach to research enabled us to relate closely to each other. I would say that was an attraction. We met at least thrice a week for one year and all that we did was to talk and share notes on gender identification issues over coffee, tea, lunch and dinner. We spent days and nights talking about it over phone, at office ... Continue»
Posted by tran4mate 1 year ago  |  Categories: Shemales, Taboo, Voyeur  |  Views: 1533  |  
100%
  |  5

Tranny's First BBC

Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me.

Normally it’s just the usual crowd of guys but several weeks ago a big muscular type African guy in his mid 30’s kept going past me and looking at me out of the corner of his eye. After about his third walk past I gave him a little smile. When I could see him coming down the hall the next time, I got up and slowly walked around the corner into the next hallway so he... Continue»
Posted by kbking64 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1531  |  
95%
  |  4

xdresser foxxiroxxi fucked by daddys poker buddies

Well its all my daddys fault he made me dress up like a slut everytime he had a poker night to serve drinks and give massages the cheap bastard would not pay a girl to do it so he made me do it. I cant really complain but as after the first couple of times the awkwedness went away and I started to enjoy it when I got compliments and started getting better tips . My daddy was getting a bit annoyed and tried to stop me doing it but the players insisted that I was to be there waiter. This is when it all clicked into gear as it was my daddy who wanted this and now he cant stop it ,so I thought i... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 1531  |  
88%
  |  2

First Time CD In Public

Just got back from a Adult Bookstore with an arcade. Prior to going I had decided to dress in garter belt and hose, short mini skirt, bra and panties, with a see thru top. Put my sweat pants and t-shirt on over it all. Walked out of the hotel and into the car. Drove into the parking lot there were only a few cars there. Went in and proceeded to the arcade. Found a booth went in and locked the door. Put the card into the machine and found a hot she-male video. Took my sweats and t-shirt off leaving me in my outfit.

I must say that my heart was pounding and could feel my head throbbing.... Continue»
Posted by Bobcat_139 2 years ago  |  Categories: First Time, Mature, Shemales  |  Views: 1530  |  
90%
  |  15

My First Kiss

This is a story in progress so please be patient.

My name is Denise Babcock. I am a longtime transvestite having begun cross-dressing when I was 12. I began to have sex with other boys shortly thereafter. But it wasn't until I was 18 that I shared my first kiss with a boy. Paul had been one of my closest friends all through high school and we stayed friends even after graduation. Often when we hung out together complained to each other about our troubles with girls. One evening he called me up to go hang out at a bar with him. His girlfriend had recently dumped him and he was a bit depresse... Continue»
Posted by DeniseTV 11 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1531  |  
100%
  |  1

My shemale boss part 3

I was woken by the vibrating noise of my mobile and looked over at the time, the bedside clock said 1am. The caller I'D on the phone simply showed Bitch, naimly my boss Miss Jones, would she never leave me alone.

I answered the phone and still being half asl**p simply said 'yes'.
'Don't answer me with that tone Rob' she said. 'Sorry, but its one in the morning' I replied.
'Be a darling Rob and pick me up from the club, text me when your outside'. Before I could say anything she hung up.

I pulled my arse out of bed, slipped on some tracky bottoms and a t-shirt, jumped in the car and dr... Continue»
Posted by big_rob49 2 years ago  |  Categories: Shemales  |  Views: 1527  |  
93%
  |  7

First Time pt 4 by trans_love (Fiction)

It’s been a while since this happened but I remember it like it was yesterday.


If you remember reading previous posts, I was a brand new teenager, about 5’2” around 110 lbs or so… green eyes, long brown hair, small b cup boobs (thanks to granma’s estrogen pills) and a VERY fem ass!! I’m a transsexual male to female. I had just been introduced to group sex at an adult book store by my ex bf’s dad, James. Not too long after my last story happened, James felt guilty about what happened and stopped wanting to see me. So there I was, lonely again. I had met up with Brian again and realized he... Continue»
Posted by 1superhornyguy 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1526  |  
100%
  |  1

Bet You Didn't See That One Coming


I looked down at my cell phone. The two way talk ID popped up. I shuddered.
"Hey baby, come out, come out, wherever you are. Be prepared, cause when I find you; You're going to find out that life is a bitch.!"
My God! What the fuck was happening to me?---------- I've created some kind of a monster! It was just a little joke. It wasn't even mean. I don't do mean. But here I am on the run!
The cell buzzed again. "Come on my sweet. Trina wants to play."
Lord help me! I might not last through the night! I have to be calm. I have... Continue»
Posted by vosmou_vrot 1 year ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1527  |  
100%
  |  4

T V times

I had an amazing experience a year ago when I was on here previously , I became friends with a sexy cross dresser called Dark Angel; we messaged each other and arranged too meet when my husband was away .. well to cut a long story short we ended up in bed together both in stockings and heels . I am on my back with my leggs wrapped around angel whilst she is fucking me on top. Because we were alone I had left the door open, suddenly I noticed my husband standing there watching . I thought he was going to explode but he put his finger to his lip as to be quiet . To my amazement he pulled out his... Continue»
Posted by tiger061 3 years ago  |  Categories: First Time, Mature, Shemales  |  Views: 1525  |  
86%
  |  4

shes the boss

This story is 100% true well as true as I can remember. This year I celebrated 40 years of marriage. I am 60 and she is young 68. We met on a mini cruise from UK to Europe. I say cruise but it was just overnight boat trip to Denmark a day there and overnight trip back. I worked in a factory and it was a works trip there. There was about 40 of us going. I was 17 and just started work there. She was 24 didn't work in factory but her mum did. I hadn't had much luck with girls and was very inexperienced, she on other hand had 2 c***dren one age 8 and one aged 5. She had got pregnant when she wa... Continue»
Posted by tvtv11uk 10 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1525  |  
61%