Shemales Porn Stories
Page 64

Sharon's Mistress Throws a Sissy Party

Sharon’s Mistress throws a Sissy Party
(Prior chapter is Sharon’s Sissy Saturday)

The next morning Mistress was kind enough to let me sl**p in, but an alarm above the door to my little cell went off at 6:30, rousing me from a delicious dream of being naked and fucked in the woods by a handsome, dark-haired man who kept me as his personal sissy slave slut. I woke with the sensation of his hard cock filling my dripping pussy, and I realized I was still leaking cum from my day in the booth. I crawled from my cell and saw a note from Mistress Angela telling me not to wash up but to dres... Continue»
Posted by scatpetsmaster 1 year ago  |  Categories: Fetish, Shemales  |  
1715
  |  
100%
  |  3

The Bachelor Party

This is one of those stories that just popped into my head after looking at a friend's pictures of a bachelor party he had recently been to. I would welcome any feed back to this story.

What started out to be a normal bachelor party couldn't have turned out to be any less normal than the one I attended last year. I was a friend of a friend so I can't say that I knew the groom or all of the guys there, but I'm an easy going guy and as the beer started to flow of course we all became fast friends.

The word at the party was that there were some strippers coming over later and we were all ... Continue»
Posted by slatemhor 1 year ago  |  Categories: Anal, Shemales  |  
3268
  |  
100%
  |  5

Halloween Pt4

(If you haven't read Halloween Parts 1-4, you'll have no idea what's going on. Except for sex.)

He broke off the conversation with the guy he was next to, and strode purposefully toward me, a cup in each hand.

"Where you going, Baby?"

Colette tried to intercede. "She's going home?" she said, with the sentence starting out f***efully, but ending on a high note,

so it sounded like a question. It was obvious he was ignoring her completely.

"I said, I'd be right back. I was just going to get us something to drink." He held up his left hand, to indicate it was for me.

Not ... Continue»
Posted by TransContinental 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
887
  |  
100%
  |  3

chase the pool boy (fictional)

after the thunderstorm and hurricane wreaked havoc on our town, and we had a lot of damage, my house was repaired but my pool was full of crap from the hurricane, no one could come out and help, everything was pretty much shut down, food was being dropped in by helicopter.
well finally, everything began to fall in place, but my pool still needed work, so my neighbor lisa(the shemale) came over and and said her friend was staying with her due to the death of his father, and knew a lot about pool cleaning and we worked out a price for the next day. i awoke about 6am and went into the kitchen ... Continue»
Posted by rollpayer1105 1 year ago  |  Categories: Gay Male, Shemales  |  
863
  |  
100%
  |  2

Missed You

The gate agent walked down the jet way unhappy to share the news. She conferred with the flight attendant. The obviously gay young man phoned the pilots. Next the woman announced, “Ladies & gentlemen, this flight has been canceled. We need for you to gather your belongings and exit the plane. We can re-book you on another flight at the customer service desk.”

Nearly every passenger grumbled with disgust. Left with no other choice, they grabbed their bags and filed off the vessel.

Jessica Stewart waited patiently conversing with other unhappy travelers when an airline employee appeared sa... Continue»
Posted by faggyboi 1 year ago  |  Categories: Gay Male, Hardcore, Shemales  |  
955
  |  
100%
  |  2

Fucking a hot Sissy in the woods

Well, this is what got me into CD myself I guess. Despite getting off being the subbie from some men and women, I always liked girls, gurls and sissies. These I liked more from an angle of domination. So this beautiful early summer day I am out on the streets with my car, doing my "travelling salesman"-job. Taking a short break, I start browsing profiles in "gayromeo". I stumble over "Melinda23". The picture was only her chin and lipstick mouth and a sweet snub nose. She wrote that she's looking for a sensible, dominant man to explore the world and have a nice fuck :) She was obviously around ... Continue»
Posted by Cellboy1 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
2133
  |  
100%
  |  5

Fun with the Mechanic

Last weekend, I had a date to go out to a bar with some other CDs in another state and a 2 hour drive. I would get dressed when I got to the motel. On the way I had car trouble, but kept driving to the motel. Told the girls who were already dressed that I couldn’t go to the bar or play because I could not relax knowing my car was having problems. I was so horny because we had set this date up a few weeks ago and I had spent the day trying on my new sexy short black dress and getting ready.

I left the girls at the motel and headed home with the car having transmission problems. On the ... Continue»
Posted by hotcdsub 1 year ago  |  Categories: Fetish, Hardcore, Shemales  |  
7215
  |  
100%
  |  4

Sissy Sharon's Saturday

The day begins at 4:30 a.m.. I am awakened by the alarm next to my bed on the floor in my tiny cell. It’s barely big enough for the old mattress I have to sl**p on, but it has been my bedroom for the past 8 or 9 years (I’ve lost track). Every day is basically the same. I wake up and crawl from my room to the bathroom at the end of the hall in the basement. Cameras watch my every move, so trying to cheat by walking (ever) is a no-no. The punishment is far worse than the crime, so I am always obedient. In the bathroom I administer several enemas, being sure to expel all the nasty waste from my b... Continue»
Posted by scatpetsmaster 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
1732
  |  
100%
  |  5

My First Taste

She was beautiful. Blonde, shapely and very sexy. She said she just loved my outfit, a pretty pink summer dress. She was in a black floral outfit, with a pleated bottom that swished around when she moved, almost flashing her panties. It was very arousing.

When we got to my place, and I put my arms around her and held her tight, she softly kissed my ear, and swirled her tongue around it. I kissed her lips and lightly let my fingertips glide down her back, and down her skirt until I could feel her thighs. I put my hand on her silky leg and brought it up to her panties, caressing her ass... Continue»
Posted by pantyboykristin 1 year ago  |  Categories: First Time, Shemales  |  
1948
  |  
100%
  |  4

Hands free cumming

One day I really felt the need for an assfucking so I broke out my favorite toy and gave it a go. The toy is a realistic cock, with balls, that is 8 inches long and appropriately wide. I started watching a video of a hot looking redheaded Shemale with big tits that was fucking a guy in the ass. I lubed up my toy and worked it up inside of me and while sometimes matching the rhythem of the guy getting fucked, I was totally enjoying both the video and my toy. I began stroking my very hard cock a little bit but realized that I would make myself cum pretty quickly if I did that so I stopped an... Continue»
Posted by theintern 1 year ago  |  Categories: Anal, Masturbation, Shemales  |  
529
  |  
100%
  |  5

Shemale suprise Colt and Celia

Colt is a young man and doesn't have a girlfriend and just turned 21 years old
He has brown hair and brown eyes.

Celia is a shemale and is 20 years old
She has half long to long light brown hair and bleu eyes.
She's got small shemale breasts and a beautiful thick cock and looks really feminine.
She likes to fuck and get fucked.

Colt and Celia don't know each other yet but go to the same bar,
but on different days.

Now Colt gets the idea of going to the bar on saturday instead of on friday.
This is the same day Celia goes to the bar.

Colt ordered a beer and Celia just enters t... Continue»
Posted by J-art 1 year ago  |  Categories: Shemales  |  
1004
  |  
88%
  |  2

Leila Has a Big Secret

I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most.

It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before.

I'd stayed over at a friend's house and after a nice leisurely breakfast I headed home so that I would be back home before dark. I had to be at work the next day and wanted plenty of rest.

I was driving along Highway 1 when I first saw her. And boy, was she a vision. It had been raining all morning and the woman who stood there beside the road w... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Sex Humor, Shemales  |  
5771
  |  
100%
  |  2

Wife Shares Shemale

"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an hour see you." She hung up.

The phone call made me really nervous.I had reasons to get nervous if not get a nervous break down. Tara and her husband owns a few restaurants in different cities across the States. I have known Tara since 6 months now since she busted me from one of the restrooms of her restaurants. Well wh... Continue»
Posted by drew1207 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
3746
  |  
100%
  |  3

The Windowcleaners

I was home alone for the weekend as my parents were out of town. I had been instructed by my online master that i had to spend the whole day as a girl (a naughty teen slut at that). No matter what i had to do that day i had to do it dressed in girly lingerie and or clothing...
I got up, showered and looked through all my outfits to decide what to wear... First of all i put on my lingerie which consisted of a white and pink spotty thong, black fishnet stockings and a black and pink teddy/basque... I had to go to the supermarket to get some groceries so i completed the look with a pair of tigh... Continue»
Posted by slut_trish 1 year ago  |  Categories: Gay Male, Hardcore, Shemales  |  
2508
  |  
100%
  |  1

Car Crash

I woke up feeling incredibly horny, it was still pretty early, around 5am. I really felt like doing something naughty and risky, so i decided i was going to dress up in my sexiest 'girl clothes' and go for a drive in my car. I had done this a few times before but usually only in lingerie under my ordinary male clothing.. As it was early i figured there wouldnt be many people around at that time of the morning so i thought id be a little more daring and go completly in girl mode this time...

I laid all my girly underwear and outfits out on my bed so i could decide what to wear. As it was sum... Continue»
Posted by slut_trish 1 year ago  |  Categories: Gay Male, Hardcore, Shemales  |  
2149
  |  
100%
  |  4

Tentacle impregnation

I had just finished a session up at the gym and began walking back to my car. It was dark out and the large car park was empty, nobody could see me. I was wearing just a tight grey leotard.

My big bulging cock showing clearly up my stomach, small wet patch from a little pre cum, my tits free, no bra, nipples erect from the cold, wobbling as I walked, along with my ass and thighs.

As I got to my car I got in and got myself comfortable, suddenly I was locked in my own car, from under my seat crawled fleshy huge tentacles in the shape of huge cocks, all dripping pre cum. They tied me to m... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Sex Humor, Shemales  |  
2586
  |  
100%
  |  4

Charlotte and her sister go swimming

I did not write this story.

I am 18, I have a younger sibling who is 2 years younger than me called Emily. Even though she is younger than me and we both come from the same parents, she has a better body than me. She is curvy, taller than me, wider hips, small waist, amazing big round ass and huge tits. I'm a D but she is an E, almost F. She turns me on a lot, I know it's wrong but I get horny thinking of her naked.

We both love our swimming. Even though this is an awkward sport for me as I am tiny and it is hard for me to hide a big 8 inch cock. I usually tuck it between my legs pushing... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
4568
  |  
94%
  |  1

Charlotte and her friends little sister

I did not write this story

After a night out I stayed over at my friends sl**ping in the spare room. In the morning my friend had work and left without waking me but she told me the night before she had work and I could stay until she got home again.

Waking up in the morning I felt groggy and tired but one thing I did notice was I woke up with morning glory, I was rock solid and made a huge tent of the quilt. I needed to sort this out. I slid my hand down into my panties where it was stretching them and slid them off allowing my cock to grow to it's full size, I was so horny and instant... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Sex Humor, Shemales  |  
2983
  |  
100%
  |  1

Walk of Shame.

As I woke, I tried to stir, to move, but in all honesty I was as thick headed as a punch d***k boxer; no thought made sense, I did not know where I was, my arms and legs were numb and I could hardly breathe....

I knew where I was. I was sure of it. I had been sent here deliberately... As I licked my dry, cracked lips which were alcohol dry and parched, there were vague memories. I had been sent here. Moaning, I tried to rise but stiff linen bed sheeting was moulded to me, it crackled as I moved making me open my eyes to accept what was around me.

The hotel room was beige, very beige and ... Continue»
Posted by CorneliaO 1 year ago  |  Categories: Shemales  |  
1646
  |  
100%

Mile High (caught in panties and pegged at 30,000

Mile High (caught in panties and pegged at thirty thousand feet)

By Mikaho, Edited by g1dnshwrgr1

I boarded the plan and was taking my seat when I noticed the most mature of the three stewardesses.  She was beautiful with a classic flair; her pencil skirt perfectly presented an hourglass waist, defined hips, and a round butt.

The image of her shapely form flitted around the edge of my thoughts as I started answering email on my phone and quickly drifted into a hyper-focused state;  oblivious to the bustle in the cabin around me until I heard her ask me to turn off my phone.  I glanced... Continue»
Posted by Shelleyisasissy 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
2830
  |  
100%
  |  5