Shemales Porn Stories
Page 64

First time dressing up: Part 2

Dressing in my s****rs clothes became a regular thing after about 2 months of doing it, I would use her vibrator on my ass at least once a week. My f****y was gone more often so it gave me plenty of time to prefect doing my make up, hair and shaving my legs. One night when my f****y WAS home i was looking for a pen to write a card. I went too my parents room to look for one and on my step mom's dresser was a small blue key, i had no clue what it would go to and for some reason it seamed important. I put it back and continued on looking for a pen

Two days later my f****y was i out so imminen... Continue»
Posted by Badassgirl123 2 days ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 1145  |  
100%
  |  5

Lisa at last

My phone buzzed “in the parking lot” was the text. “Meet me at the side door” I quickly texted back. It was dark out as I opened the door and Lisa slid past. She followed me in silence as we went down the hall and I opened my room door. As I closed the door we paused looking at each other. She had long dark shoulder length hair, dark black eyebrows. Her brown eyes were sexy circled with dark black mascara and eyelashes. her lips were a mild pink, her neck had a dark black choker and she wore a necklace with a black heart. She was in a cute black dress that just covered her small chest with sh... Continue»
Posted by iheartm2f 11 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1133  |  
100%
  |  6

The Fanncy **Dress** Party

I went to a Priests and Prostitutes party a short while ago in South Africa and loved getting dressed up as a prostitute, it was so much fun and It made me really horny.

I had to get a cab dressed up like this and we all met in a bar before hand. I was the first one to arrive at the bar which was already packed as it was a Friday night and the early (going home from work) crowd had not left. I sat quietly at a table and ordered a double Vodka and Tonic and was watching the door hoping that someone else from the party would come to assist me. I must have been sitting there for 10 minutes an... Continue»
Posted by africangraham 2 years ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  Views: 1131  |  
11%

A Sissies Humiliating Confession

This is a real life situation that happened this past weekend. I am sissy slave jennifer and i am owned by my beautiful Mistress Rita. Mistress Rita loves nothing more than putting this pathetic lil sissy through the most humiliating situations She can get away with. I once confessed to Mistress that when i was 16 i wore my very 1st pair of panties. Mistress insisted that i tell her who's they were, where i got them, and how i got them. i was embarassed to confess that i actually stole them right out of my mother's best friends panty drawer. Mistress insisted i continue and to give her the com... Continue»
Posted by jenniferday 2 years ago  |  Categories: Masturbation, Mature, Shemales  |  Views: 1130  |  
100%
  |  11

sissies obey rules


1. A real sissy whore is always ready to be fucked at anytime and anywhere
2. A real sissy whore shows sissy clitty and cunny at every opportunity
3. A real sissy whore begs to be fucked hard
4. A real sissy whore sucks anything that's offered
5. A real sissy whore must be prepared to be fucked in any position
6. A real sissy whore does as told no matter how dirty and low the task
7. A real sissy whore plays with herself as instructed for others amusement
8. A real sissy whore loves being m*****ed in public
9. A real sissy whore moans loudly, especially when allowed to cum
10. A rea... Continue»
Posted by sissyteri 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1130  |  
100%
  |  3

extreme cuckold

There i was typing away on the keyboard chatting to others in the hope of a meet up for dressed up playing together.

The private screen popped open to reveal a message from a genuine girl requesting a chat, well as I was there and hopeing for a meet what was there to lose, she started by the introduction that she liked to be called barbara and her other half she would tell me later depending how things went.

babara stated that she wanted both a lover to give her some good sex and a tv to try sex with as that excited her also and she may want her other half to experiment with the tv, well... Continue»
Posted by natasha1975 2 years ago  |  Categories: Shemales  |  Views: 1129  |  
75%
  |  2

My First TV Cottaging Fun

My first time (And this is Genuine, I assure you)

I dressed under my normal clothes and took a rucksack with other bit's & pieces in and went to a nearby "Cottage" that had 2 Glory Holes, when I got there, it was empty, so I went in the middle cubicle, finished dressing: Stockings & Suspenders, High Heeled Lace up PVC Boots, PVC Basque etc.

I didn't have to wait long, the cubicle's then got occupied either side, through the peep holes in the door, I could see at least 2 other guys at the urinals.

Then I saw fingers appearing at the hole to my left, I looked through the hole on my rig... Continue»
Posted by uktvmaid 6 months ago  |  Categories: Group Sex, Mature, Shemales  |  Views: 1129  |  
100%
  |  11

him again :)

Since my roommate has moved out Ive taken it upon myself to begin exploring my Transgender tendencies. I shaved my legs, cock, chest everything. As I walked through work the first day, just feeling my jeans against my smooth shaven skin was a huge turn on, I felt my little sissy clit getting harder and harder as the day went on, tugging my panties tighter and tighter against my little bitty pussy ass, as they get stretched out. Its so erotic knowing that I am such a slut, that underneath my dirty grungy work clothes is a sexy soft girly sissy begging to be abused by cocks. mmmm. Spending all d... Continue»
Posted by Chubby_Decatur_Sissy 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 1128  |  
96%
  |  5

First Time pt 3 by trans_love (Fiction)

Introduction: This is a true story that happened to me when I was a young "woman"

Here's another. Again, I was 13 at the time, I was 5' 2" , 105 lbs, long brown hair, green eyes, ass to die for, I stole my grandma's estrogen pills and started growing boobies, I was now a full b cup.

A couple weeks went by and I only seen my younger black guy a few times. He let me suck his big cock but that was it. One day he told me he met someone else and to not come around any more. As I turned the corner and was heading home his dad, James, pulled up along side me in his car. He said, "Jessica, why d... Continue»
Posted by 1superhornyguy 7 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1129  |  
92%
  |  2

Elamehs night out

I Finally Got A Chance To Dress Up And Go Out My Wife Dosent Know Bout This She Went Away For The Weekend To Connecticut So I Dressed Up In One Of her Dresses And Finally Went To A gay bar Called The Cubby Hole In Manhattan NY


http://xhamster.com/photos/view/2889342-47848481.html



It Was A Nice Spring Night. So Off i Went To Finally Find A She Male. Oh By the Way I Have A Thong On And A 8in Butt plug Up My Mancunt.So I Hopped On The train To West 12st, And Let me Tell You It Was Great To See All those People Looking At Me On That train. So As I Got off And Started To Walk Down The... Continue»
Posted by elamehs699 3 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1127  |  
100%
  |  2

the real me part two

I took the mail in the house and mom was on the phone.She got off the phone and said we need to do something now. I said what she said go to my bathroom were she had me lift up my dress and take off my thong an bend over. I felt something cool and wet on my hole.Then felt her slide something warm inside me i moaned a little the felt warm liquid flowing in me,she ladies must douche and be clean and fresh.Then right in front she did her self her pussy was smooth with long lips.
Well it was close to 9 pm and she asked me if I would drive to the next town and get some stuff at the store.I grabb... Continue»
Posted by cdpaula 2 years ago  |  Categories: Shemales, Taboo  |  Views: 1126  |  
94%
  |  3

tranny e****ts are the best

Being a rather horny fellow who loves to get spun on meth and party, I occasionally had to craigslist and check out the casual encounters section to see what's out there. So after seeing The Hangover 2 and seeing sexy transgendered girls it got me a little curious to try it out i mean what could i lose they couldnt say no to my 10 inch cock. So doing a big bump my cock was leaking as if i just had a wet dream , I got home and dared to check the T4M section that was so naughty and off limits before. I came across an ad where a passable Latina wanted to have some fun and she included some pics. ... Continue»
Posted by brianlongham 1 year ago  |  Categories: Anal, Shemales, Taboo  |  Views: 1126  |  
43%
  |  2

White sissy tp black man

On the bed in the guest room, Jamie lay back against the flowered pillows, feeling pretty in his pink satin nightie, his stockinged legs spread wide, and the long black vibrator pressed to the mound in his panties that betrayed his tied-back cock. He slid the straps of the nightie off his shoulders and pulled one pale little tittie out a frilly lace-lined cup. He squeezed the small sensitive nipple and took the vibrator off his already wet panties and placed it instead against his tight asshole.

"Oohhh…" he moaned, licking the raspberry lipstick off his lips.

He opened his made-up eyes a... Continue»
Posted by jeffreybarnes 11 months ago  |  Categories: BDSM, Interracial Sex, Shemales  |  Views: 1127  |  
84%
  |  2

my first tranny pt. 2

it felt so good to cum in her mouth. that wasn't planned. her mouth just felt so good. nice & wet. told her what really got me off so fast was having her cock in my mouth.

"in that case, come here & suck it some more."

she laid down with her legs open & her dick in the air. without hesitation, I got between those nice long legs & put her dick in my mouth. she was moanig as I sucked her cock. she was about a good 6 inches. I just sucked & sucked. she put her hands on my head & was making me go up & down. I got her cock nice & wet.

I never told anyone this but, I loved sucking her coc... Continue»
Posted by radec_24 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1124  |  
94%
  |  3

Daddy always wanted a little girl

I SAW my daddy and his friends fucking a tranny one night and the next night he had a poker party. SO I got some of the sexy clothes he had. MINI skirt black lacy crotchless bodySUIT heels, wig makeup, EVEN IN my wheelchair, I LOOK LIKE LIKE a whore. Toward the end of the night I rolled out to driveway where his friends would park there. HE HAD one overweight friend about 350 whom i had seen fucking trannys several times. I WAITED BY HIS CAR, HE HAD A HUGE COCK, i wanted his cock.I GOT IN THE BACKSEAT OF HIS WITH AHUGE DILDO AND STARTED WORKING IT. When i saw him cumming, I pretended to be on... Continue»
Posted by cdaisy 2 years ago  |  Categories: Shemales  |  Views: 1124  |  
71%
  |  1

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 2 years ago  |  Categories: Fetish, Shemales  |  Views: 1124  |  
100%
  |  3

LAST NIGHT (FUN COUPLE)

Last night I got a call from a horny couple that i've played with recently.
I really liked this couple, Beth and Joe, they are in thier early30's and love to fuck.
It helps that they are Bi and Beth is the more dom of the 2, and has great control over Joe.
Beth asked over the phone if I wanted to fuck Joe, and I said sure, love to.
She said on one condition, that she just got a new strap-on and wanted to try it out. I really got excited and ran right over. I wore a matching bra and pantie set with a garter belt and stockings. I am a naughty little slut, I put my panties on after I put o... Continue»
Posted by jennifersusan 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1123  |  
85%
  |  7

Nipples are a gurls best friend


One night I happened upon a website that sold nipples clamps and thought to myself that must feel pretty sexy. Then I saw it... nipple pumps! My curiosity got the better of me and soon I had the mighty credit card out and had ordered some. It was a long 2 weeks before their arrival, and as soon as I was home I had the box open.

I put one pump on, then the second one and pulled on the bulb to create some suction on my nipples. OMG! these things work! My nipples immediately felt like they were being pinched, and pulled on, which I must admit felt really sexy.

Over the course of the wee... Continue»
Posted by thereal_raavii 1 year ago  |  Categories: Fetish, Shemales  |  Views: 1122  |  
56%
  |  5

MY SYBIAN

I have had my eye on the Sybian for about a year now. I watched a blonde sort of curvy girl use it once & they way she was convulsing made me envious of the toy. I really enjoyed watching her ride it, I could genuinely tell that she was getting off incredibly hard. Her screams alone made me hard. I finally decided to buy one and give it a test run. When it first arrived at the door & went running like a k** in a candy store. I practically ripped the packing to shreds, lol. When I opened it up I realized that they had sent all the attachments that I had requested. There must be 10 different att... Continue»
Posted by cocklover47 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 1122  |  
90%
  |  13

markie dunlap Kansas city sissy for all black Mast

I am a Sissy Faggot! I have been programed by hypnosis to write (beg) to be owned and femenized by a black Master in Kansas City Mo. For months I have watched repetedly sissy hypnoses videos and black cock worship videos. My girl freind set it all in play when she found me dressed in her panties bra and stockings. She has comanded me to tell all who read this that the phrase (black cock sissy) will in fact make me your sissy cock slave to dress me and use me as you wish. She has also instruced me to make it more intresting and let you know I live in Lees Summit and that Since I will not rememb... Continue»
Posted by markie2269 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1120  |  
98%
  |  6