Shemales Porn Stories
Page 117

Caught again

So I’m finding it hard to get privacy to dress up of late. So I decide to go down the country and rent out a holiday home for a weekend. I brought all my gear including make-up,and wig. When i arrived at the holiday park I entered the reception area. Behind the counter was a pretty women named Jill. I introduced myself and filled out the required forms.

“You be staying in trailer 9, my husband will show the way……Mike!!!!. She yelled.

Mike walked in to room, introduced him self and took my bags. Little did he know one bag was full of lingerie and dildos. Mike was medium build and around ... Continue»
Posted by monkeynuts0 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1794  |  
97%
  |  9

A f****y Friend 5: The Party part 2

The continuation of A f****y Friend 5, wanted to input a huge fantasy of mine into this one, and I think it worked out really well. This is the longer of the halves, but I really think you'll all enjoy it. And I hope you do!

“Give us a striptease!” one of them said. So I began to dance around for the ladies taking off piece by piece of clothing. They told me to leave the lingerie and stockings on, it got them hot. “Now bend over and spank that ass.” I did as the ladies requested. I bent over and gave my ass hard spanks until the ladies had seen enough. “Now stand up whore” one lady said. Sh... Continue»
Posted by Virg 3 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 772  |  
84%
  |  2

Helping a friend

Anna has been working in my office for a year now. I have never heard her talk about a boy or girl firend. Anna is 5'7'', long legs, light brown hair almost to her waist, very pretty. I have always talked to her, had lunch, but she had never opened up until she needed some help.....

Anna had bought a house that needed work. A couple of months after she bought it, she was complaining that her sink leaked. I told her i had done odd jobs through out my life and i would be more than happy to check it before she called a plumbler. She told me to come over friday after work.

Friday came,... Continue»
Posted by edukateme 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3202  |  
95%
  |  14

Nancy finds out...

However, Nancy’s stay with us that summer was going to prove even more eventful than ever I could have imagined. Even after having been caught wearing her things by the neighbour’s son, Lesley, which led to a whole new dimension in our friendship, as you’ll know if you’ve read “Caught in the Act…”

Once again I found myself alone in the house. Dad was at work and Mom had gone to her Bridge Club and wouldn’t be back for ages. As you’ll know if you’ve read “Caught in the Act…” Nancy was really hot stuff and didn’t care who knew it. At 18 she’s a couple of years older than me, in the full bloom... Continue»
Posted by caroletv31 3 years ago  |  Categories: Lesbian Sex, Masturbation, Shemales  |  Views: 1775  |  
96%
  |  7

Caught in the Act....

One summer, my cousin Nancy came to stay with us for a while, as her parents had gone away on a cruise trip. At 18 years old, she was a couple of years older than me and in the full bloom of her young womanhood, so to speak. She knew it, too, and it was obvious that she had no problem at all in pulling any guy she wanted. Not only did she look good, but always dressed very sexy, just to make sure…

She was another of these girls I adored during my adolescent years, who LUVed to teeter around perched on very fine pointy hi-heel stilettos, and when she walked, her butt swayed from side to side... Continue»
Posted by caroletv31 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 3815  |  
94%
  |  8

wish cum true

A wish cum true

My wife and I have had a strong and open relationship from the start. We have accepted each other and all our wild passions, and we have always been open about our sexual desires. Having said this I will try to express what happened the other night with the same intensity I experienced.

I came home from work and saw Tara's car in the drive. Strange; she gets in after me most days. Never the less, it was a nice surprise. As I walked into the house she met me at the door dressed to the nines: short mini, fishnets, low cut top and those pumps that I love. Tara is 5'4" and 10... Continue»
Posted by tara-cd 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 964  |  
99%
  |  8

Becomming a Sissy Slut

Sandy's Life
My name is Sandy Johnson. I chose that name 35 years ago because I like Sandy and I knew a hot female with the last name Johnson. I first remember finding my mothers underclothes in the bathroom closet. We she and my Dad would go out I could go in the bathroom and put her slip on and find a pair of dirty panties in the dirty clothes hamper. I still love the feeling of an old fashion girdle!

I dated in HS and went to college, married, went to war, had c***dren, divorced, married again and divorced again. All this time I kept buying women's clothes and... Continue»
Posted by sandynccd 3 years ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 1322  |  
76%
  |  4

transvestite in trouble part 3

I felt his stiff cock at my asshole. I shuffled my legs a little further apart, partly to prevent him ramming it into me and it hurting, and partly bacause I just wanted him to fuck me!

"you fuckin dirty slut" he whispered...he'd noticed my little subtle movement " you want my cock don't you?....Say it slut"
"yesszz" i mumbled through the ball gag "please" i tried to say
I was terrified of the situation I was in....what the hell was he going to do with me after he'd screwed me, he'd pretty much ****d me....yeah, I'd let myself get in this situation, but he'd f***ed me and it was all on ta... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 755  |  
90%
  |  9

Gloryhole slut last night.

Well I was a horny slut last night and went to this little arcade in the city last night. Fully slutted out and in a new pair of silky nude hose I was hoping not to be disappointed....I was not!

I payed my fee and went into the back to the booths where there were a massive amounts of guys in the booths and just standing around. I was a little nervous waiting on a gloryhole booth to open but was catching the eyes of all the horny cocks also waiting for a turn in the boths. Finally after a few minutes 2 booths opened up and I went in hoping to get my hungry lips working right away. No soon... Continue»
Posted by luvpantyhose67 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 2874  |  
94%
  |  19

Tranny whore Samara Rosetti at a Trucker's jo

Last night I got a call from a client. He told me to meet him at a small bar close to Olga Street in Stuttgart.
He ordered me to dress as follows: Short black leather mini skirt slit up the side, button down red silk blouse unbuttoned 3 buttons, 16cm spiked heels boots, fishnet body stocking, no bra, and absolutely no panties. I dressed as he demanded with one exception. I wore red lace panties, thinking that if he got far enough to see them, he wouldn't care that I wore them. I'm an idiot.
I met him outside the bar. I was standing there he pulled up in a tuck. He stopped and told me to foll... Continue»
Posted by Sexysamara 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 634  |  
100%
  |  11

Summers of Love (Part 2)


The weekend following that memorable Ann Summers party saw part two of my sissy humiliation although to be honest, unbeknown to my wife, it was yet another dream coming true.

I was in my workshop grinding a cylinder block down when I became conscious of the distant sound of the front door bell ringing. It seemed to ring for ages and I was just about to wipe the excess oil off my hands and go and answer it myself when the constant droning stopped to be replaced by the excited chatter of female voices. I decided another coffee morning was in the offing so headed back to my workshop.

15 m... Continue»
Posted by MichaelaCD 3 years ago  |  Categories: Shemales  |  Views: 933  |  
98%
  |  2

Woke up in a fuck

This is a small story so dont get pissed off k?

Wednesday 2:00 AM
I woke up not realizing where I am and looked around.
I saw panties,boxers,bras,and about 5 guys fucking sl**ping girls (3 girls) i saw that my shirt and bra was off but my skirt remained untouched.
somehow i was atracted to them fucking so i watched and jacked off. About 5 minutes later i came over a guys sl**ping face. then i thought,"Why not try it out?" So i slipped on a rubber and got some lube and carefully slipped in and fucked him. It wasnt long b4 he woke up as soon as i took my rubber off and came on his face ag... Continue»
Posted by FuckmyhornyAss 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1372  |  
78%
  |  6

First Real Cock i got

I must have been around 15 and it was during a carnival festival. Most of the boys were dressed as cowboys, super heroes, firemen etc. For me it was the chance i was looking for to dress up on woman's clothes.
I had picked up a mini dress, fishnet and a small top that was letting my belly free. I got a blonde wig (not the best quality) and tried to make up as good as i could. The result was not the best but for me it was huge.
I went down on the streets to walk without fear as everybody was dressed up, ended up with a friend of mine in a bar. He was dressed as an old granny!!!
After half ... Continue»
Posted by crazysissy 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1611  |  
92%
  |  4

Summers of Love (Part 1)



A couple of weeks ago my wife hosted an Ann Summers party. I had hoped to sneak away for the evening as, though I would have been more than interested in the lingerie on display, I didn't fancy listening to the constant cackling common to "women only" parties and also the inevitable anti-partner jibes such as: "I ask are you in yet and he says I'm finished", "he picks his nose and farts afterwards" and "you'd think he was rodding a drain the way he goes about it" etc. The wife had other ideas however and I was drafted in to prepare the nibbles, pour the drinks and answer the door, the latt... Continue»
Posted by MichaelaCD 3 years ago  |  Categories: Shemales  |  Views: 974  |  
96%
  |  5

The Mechanic

My name is Bruce, I am one of those mobile mechanic chaps you call out when something goes wrong with your car. You get to meet a nice variety of people, some good some not so, with some very good looking ladies thrown in as well, which make it nice. A lot of the clientele are people you see a couple of times a year for a car service so you get to know some of them quite well.

I hadn’t had that much in the way of action for a long time. I had split with my wife a few years before and now I always seemed to be working. Anyway it’s not the most attractive of looks when you hands are covered ... Continue»
Posted by domestique01 3 years ago  |  Categories: Shemales  |  Views: 1502  |  
93%
  |  4

16 ladyboys jerked off in front of me! live!

Just got back from Thailand and had a very special birthday present. A big party had been arranged for me at my favorite ladyboy bar and a “competition” had been secretly arranged for me.

Had a nice party with balloons, food, drinks etc then a midnight I was told that it was now time for my birthday present. The door to the bar was closed a chair was bought out and put against the closed door and I was told to go sit on it. Then I was blindfolded and a bib put on me. I could hear all the ladyboys giggling and moving about.

The blindfold was removed and I was greeted with the site of ... Continue»
Posted by toniparr 3 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 1505  |  
96%
  |  10

Seven Minutes in Heaven

This is purely a work of fiction about two 18/19 year olds...


It is the summer before our first year of college and we are home alone at his house. My mom works from home, but his place will be empty until his s****r gets home from her summer internship. We have been playing truth or dare since we got up this morning. However, as close c***dhood friends there are few questions to ask when we keep no secrets. Our game has purely consisted of dares.

Early on, I was dared to put on women's lingerie. Most of the day I have been dressed up in a black fishnet body stocking with a matching b... Continue»
Posted by pantiedslave 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1313  |  
96%
  |  1

f***ed feminisation


It all started as just a game. i logged into a f***ed feminization chat room and portrayed myself as a slave being punished by my Mistress. Saying She had instructed me to enter this room for 5 minutes and obey any command given to me. It seemed harmless and exciting. How stupid could i have been. Instantly i began getting messages for me to strip and show my ass and my face in various poses. There was one in particular who led the show. He f***ed me to put on lots of makeup and lingerie and pose myself as a sissy slut begging for cocks to serve. Everything was done on cam. i was naked sprea... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3011  |  
98%
  |  24

SISSIES TRAINING PART 2

SissyIndy©

I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by the sight of this brunette in a pink corset and black stockings leading down to her pink high heels being pounded by this horrid machine from both sides. Knowing that the slut in the video was me, a man f***ed to wear these whorish clothes and caked on makeup with a brunette wig bounci... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1738  |  
99%
  |  7

His sexy flies catches my eye

Another routine day was passing as I carried my shopping bags back home. Turning up a side street the late afternoon sun shining I suddenly encountered the most sexy guy I had ever seen. He was so cool that I hadn't even seen guys on TV as cool and good looking as that.
He was an Asian guy in his mid 20s tall and with a really muscular and well toned body. He had a confident air about him maybe with a touch of manly arrogance too born of an awareness he had that he was a big guy. He was with two other Asian guys and together they maybe looked the sort of guys who knew they were big and used ... Continue»
Posted by emma66 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 521  |  
100%
  |  2