Shemales Porn Stories
Page 79

My proposal

As you know from my previous stories, I hooked up with one of my best friends, Sarah, and since then we were lover. After almost 3 years of loving each other, i decided to take my girl in a mini`trip to HongKong for our anniversary.

When we arrived there, we visited the town, and after some sex we went to bed. I couldnt sl**p so i`ve started to think about a way to propose to Sarah, and I had an awesome ideea, getting some help from a Shemale. I wasnt into shemale / male thing for a 3-way..but some of the asian shemales look too fucking awesome.

Next thing in the morning, while she was s... Continue»
Posted by mercander 3 years ago  |  Categories: Anal, Shemales, Voyeur  |  
1039
  |  
98%
  |  2

Stephons first run in with Sora

I'm a young, attractive, slender, african american young man. I'm on my grind everyday. I like to drink, sl**p, and fuck. I find that I can make any woman laugh until it is about that time to fuck. This is just one incident that proves this stament.

Alright so I'm in one of my classes doing my regular, being a class clown, and funny as hell. all of a sudden the most amazing looking female walks through the doors of our lecture hall and im like... Fuck, its time to calm down because if i want to sl**p with this female anytime this century I'm going to have to show that I'm a catch, and not ... Continue»
Posted by cooler34 3 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
779
  |  
98%
  |  4

In Hose and Heels for Daddy

It was shortly after my 14th birthday when I made the decision to seduce my Daddy. I mean, all of my girlfriends were having naked fun with their daddies. I didn't wanna be left out ;-) After all, me and my BFF, Ashley, had been getting naked and having fun with her daddy for 2 whole years now...and with her b*****rs...and with her uncles...and with her cousins...and with her neighbors...and with her...awwww, shit...you get the picture ;-)

It was the morning after my first experience with my Daddy. I was camping out in my back yard and had told some guys to come over for backyard blowjobs.... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Anal, Shemales, Taboo  |  
7553
  |  
98%
  |  11

The Intimate Dinner Party

Susan and I were filled with anticipation as we arrived at Victoria’s house. We had been invited to what the written invite referred to as a “Sexy and Intimate Dinner Party”.

Victoria was renowned for her unusual, and always different, dinner and cocktail parties. She certainly did not like doing things the way other people did them. You never knew what to expect, but you always enjoyed them and could say that you’d had a new and exciting experience.

My wife, Susan, was looking incredible. She had a short black skirt that really set-off our beautiful long legs encased in sheer black sto... Continue»
Posted by didi_galtier 3 years ago  |  Categories: Group Sex, Shemales  |  
1815
  |  
98%
  |  8

Caught by Neighbor

Caught by Neighbor


- 1 -

It was a beautiful warm day, and I had it to myself. My wife Sam was interstate on business for the week, and not due back for another five days. For me that meant housework to be done, but plenty of time to enjoy my own space, and entertain one particular hobby. I smiled to myself, and not for the first time, I stopped in front of a mirror and pulled my tracksuit pants down, admiring the bright pink, silky panties that I'd been walking around in all day.

I'd been cross-dressing for many years before I met Sam, but it really wasn't her thing. So I tended to ... Continue»
Posted by Femluver 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
11674
  |  
98%
  |  27

Passionate One Night

Passionate One Night

His name was Shawn. He was a cute, very cute, guy that was living in Houston when he was making his way to the small town of Llano, Tx. He was planning to meet f****y so he could go dove hunting. I had posted an ad that night to see if any of these dirty minded straight boys would respond. He responded late at night when it was about two in the a.m. I was a bit skeptical. He had that southern accent, great body, tattoos, seemed a little too good.
"Too Good" turned out to be...real?
After I had given him the address, directions to my apt, I could hear the loud noise fr... Continue»
Posted by GoodDickLoved 2 years ago  |  Categories: Anal, First Time, Shemales  |  
1041
  |  
98%
  |  4

olderman and mature crossdresser part 2

We left the park and drove to his house which was very nice.I knew he was wealth when he picked up due to his car was new jag. He fixed me drink and we sat on his couch and kissed and made out an heavy petting.He kissed my neck driveing me nuts as he did I rubbed his cock thru his pants which was hard.He asked me if he had gone to far I said to him if you did I would have stopped him.
I asked him how far did he want to go and he said it was up to me.I looked at him an gave him kiss an asked him were his bathroom was he told me so I stood up leaned down and whisper in his ear that I hoped h... Continue»
Posted by cdpaula 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  
876
  |  
98%
  |  6

A Quickie For Jemima

I checked my make-up and adjusted my brunette, bob cut, wig in the bathroom mirror. Pleased with the results I then ensured that my clothing was right. I was a vision of darkness: black G-string under black thin denier tights, 3 inch heels, black satin vest top and black mini skirt. I was sure Simon would approve.

I walked slowly yet purposefully to the bedroom. Simon was sitting on the edge of my bed naked stroking his cock looking at me “mmmmmmmm,” he said seeming to approve “ Why don’t you cum and join me the doors open?”

Out of habit I shut the door as I enter in case we made a lot ... Continue»
Posted by JemC 3 years ago  |  Categories: Gay Male, Shemales  |  
833
  |  
98%
  |  3

Old trannie gets a boys virginity

Oh dear I’ve been a bad, bad old trannie. I let a teenage boy seduce me.

I normally only go with guys over 30 at least. But this teenager contacted me on a dating site. I gave him the normal “Thanks but I’m in my 40’s you’re a bit on the young side for me” reply. However he kept contacting me on the site. He was very curious and quite sweet. I chatted with him online and he said that he would really love to meet me.

I told him if he wanted to meet me that he could find me at my local sex club. He said he couldn’t go there. After a deep thought I said it would be O.K to come round on the... Continue»
Posted by toniparr 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
4464
  |  
98%
  |  12

the man i used to be

It wasn't what she said; it was the way she said it that got him to do everything she commanded. It wasn't that he couldn't overpower her...after all, he was a man of six feet, and she was a woman half a foot shorter and 100 pounds lighter.

It was like a teenaged son having a confrontation with his mother. He could overpower her, but he wouldn't because, well, because she was his mother. Neil could overpower this woman, but he wouldn't because, well, because she was his lover.

She had measured him very carefully about six weeks ago now, chest, waist, hips, not just the circumference meas... Continue»
Posted by pcarter 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
967
  |  
98%
  |  2

My First Cock

I always knew I really was meant to be a girl. For a while I thought I was simply gay, but I loved wearing thongs and bras. I loved masturbating while pretending my asshole was a vagina. I never made it a secret. I'm very flamboyant and girly. I still managed to have lots of friends in high school. Several of them knew I wished I was a girl.

One night I was very upset about God knows what. I was crying with a good friend of mine at his house. He was straight and had a girlfriend (another good friend of mine). I began venting to him about wanting to dress like a girl and be treate... Continue»
Posted by hotchickinchitown 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
4139
  |  
98%
  |  24

Three's a Crowd

It was 8 pm and the guests were about to show up. My tight little bunghole was not virgin anymore and I felt like walking on clouds. I felt very feminine and quite demure. I had helped Carlos set up the table with snacks and put sodas and beers in the fridge. I looked in the hallway mirror and everything was still in place.
"You look adorable sweet cheeks", Carlos murmured in my ear and squeezed my ass. He went to answer the door as his guests arrived. A short plump blonde boy went past Carlos and to the guest bathroom to change. As he went past me, the guy winked at me. I could not imagi... Continue»
Posted by latinCharm 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
1861
  |  
98%
  |  9

I am such a slut.......18

"Hi Derek. I was just thinking about you. I haven't heard from you for a teeny bit" I replied. It was so nice to hear his voice on the phone and the sound of it caused me to stir within. Something about him, about what he did to me, about what he made me do, just had me.....and I think that he knew that.

"Baby, I have a favor to ask. It would mean the world to me if you would do it. And I would be there with you, okay?" he said, and my mind raced at what the favor might be. "I have this client and his wife....and they have a friend or two. I told them about you and showed them some of our ... Continue»
Posted by snuggle11 3 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
1304
  |  
98%
  |  6

I talk with my newest Slave

Now it was only virtual, but soon, I will fuck that slut in real!


Lady_Mandy
I want that you call me Mistress, do you understand that, slave? You will do what I say and you will satisfy your Mistress.
So you would like to such my cock, yes? Filthy bitch! I thought that you are a cocksucker! Mhh, suck my cock, pleasure your Mistress!
Don't touch your dirty cock! Suck your fingers like you would suck my dick, you filthy whore!

Slave
Yes Mistress, I want to suck you hard cock!
Oh, I wish my finger would be your hard dick! I want to taste you.

Lady_Mandy
Bitch! I would fuck your f... Continue»
Posted by Lady_Mandy 3 years ago  |  Categories: BDSM, Masturbation, Shemales  |  
755
  |  
98%
  |  7

How I Became Vanessa Chapter 1

PART I:

I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husband moved to our place with a beautiful daughter named Elena who was only 18. I was a handsome 22 year old blond boy, quite feminine in my features and certainly very shy with girls because of this very reason. My girlfriend, July, was actually my first one, and she did the first step towards me. I was not rea... Continue»
Posted by slutyvanessa 2 years ago  |  Categories: Shemales  |  
1870
  |  
98%
  |  11

Job Opportunity

So. A bit about me. I'm 5'4", 139 lbs, long brown hair and deep brown eyes. 5.5 cock, cute 'bubblebutt'. I had been looking for a job for a long while with no luck, and REALLY needed the money bad. I finally got a call from the female owner of a coffee shop I had applied to. I had actually filled out one of the old fashioned applications. As in paper, not online. I had handed it to this owner and she just smiled and said nothing. I felt kind of weird about that smile then, but said nothing and just smiled back.

The owner was a VERY cute voluptuous redhead at coffee shop who was to 'show me ... Continue»
Posted by rockywhoreor 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
1814
  |  
98%
  |  5

Baby Sitters Secret


The story that I am about to tell you took place on a day that started out very ordinary, but would end up as the least ordinary day of my life. Until that particular Winter day, I thought I knew who I was. I was Peter Fuller -- respected educator, devoted husband, loving father. I had never cheated on my wife, I had never lied to a friend, and I had certainly never slept with a girl that young before. All of that changed within a matter of hours. But you know what? I wouldn't change what happened for the world.

Years ago, I moved to the small town of Emberton, Rhode Island to take a job ... Continue»
Posted by drew1207 3 months ago  |  Categories: Anal, Fetish, Shemales  |  
9546
  |  
98%
  |  15

3 Teen Cross Dressers Misadventure - Part 3 Final

I was with two of them on the bed. One of them spread my legs and began to rub his cock up and down my stockings, I could feel him growing hard. The other sat over my chest and told me to open my pretty mouth. I did but no way could I take it all, he must have been around 8". He shoved his cock into my mouth and down my throat thrusting as I gagged. Although I couldn't see, I heard pleasurable moaning from the man on the bed with Sean. Craig, on the couch with Brett said "I’m gonna screw that pretty little hole of yours and make you scream like the bitch you are." No words came from his mouth,... Continue»
Posted by ClaireCD 4 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
752
  |  
98%
  |  3

The ConVentioN part

2. Arrival
Pulling against the chains that secured her arms over her head, Sasha whimpered in frustraition
yet again. Her bonds hardly rattled at all as she shook and twisted her body to try and get free.
All she succeeded in doing though was making her heavy tits jiggle and bounce painfully. Alone
and naked save for the few cow patterned garments her mistress had allowed her, Sasha cried
softly in the darkened room. Her breasts were swollen with milk, now each one was larger than
her head! Pink bands had been tied to the base of her nipples, preventing any of her milk from
leaking out.... Continue»
Posted by peterbtrs 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
1029
  |  
98%
  |  3

First Time By Transsexual

When I was 21, I spent a summer in a southern city doing a service project. I was engaged to a girl and excited about marriage, but I was also extremely curious about the male body. I was one of those k**s that masturbated constantly, and almost always about sex with a man or a transsexual. The summer before my senior year, I was down in this southern city living completely on my own for the first time. Since I was doing a service project, I only got one night a week off. I wasn't sure what to do with that night since I didn't know anyone, so I decided to get d***k. Several times, I just went ... Continue»
Posted by kbking64 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
1566
  |  
98%
  |  3