Shemales Porn Stories
Page 121

jobsite surprise

The other afternoon I went to deliver an estimate for a large gardening job I had been working on. When I arrived at the house I rang the bell and waited. There were two cars in the driveway but no answer at the door, so I walked around the back to the pool. As I came around the corner to the large hedgerow separating the back yard from the pool I heard two female voices talking and giggling. Passing the hedge, I froze dead in my tracks. My eyes flew open wide and my jaw dropped at what I saw.
Beside the pool, the lady of the house was making out with one of the most beautiful women I had eve... Continue»
Posted by leadpencil21 3 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
2133
  |  
98%
  |  3

My new feminine compulsion

Until I saw shemale porn on the web back around 1998, crossdressing had never occurred to me. But when I saw those doubly-sexy bodies, with both breasts and a cock, my sexual life really changed. I searched out every shemale porn site I could find, and found myself especially excited by hot shemales sucking a man's hard penis. It just turned me on so much! Over time, I started to see pictures of the men sucking the shemales - oh my god! Once I saw that - those beautiful bodies, the stiff cocks, and the men taking them in their mouths, I knew what I wanted.

It started with buying a tube of ... Continue»
Posted by marlynn 3 years ago  |  Categories: Shemales  |  
797
  |  
94%
  |  6

My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the room. Like I said there were lots of beautiful ladys there but one caught my eye. She was not too ta... Continue»
Posted by wildbill975 3 years ago  |  Categories: Anal, First Time, Shemales  |  
4574
  |  
16%
  |  14

the hunt is on

So, now that I was hooked I had to find a way to get panties on my own. A friend of mine said he was he was going to Best Buy and ask if I wanted to go along. The closest Best Buy is about 30 minutes away and in another town, since I didn't get to go there often I quickly agreed. As we get near the Best Buy Store we passed a Walmart, a Kohls and a Marshals and I realized they are all just filled with NEW panties. I suggested that when we were finished at Best Buy maybe we should stop by the Kohls, since we do not have one in our town. I told him I wanted to look for new jeans. About half way i... Continue»
Posted by peggyacd 3 years ago  |  Categories: Fetish, Masturbation, Shemales  |  
741
  |  
100%
  |  1

the hunt is on

So, now that I was hooked I had to find a way to get panties on my own. A friend of mine said he was he was going to Best Buy and ask if I wanted to go along. The closest Best Buy is about 30 minutes away and in another town, since I didn't get to go there often I quickly agreed. As we get near the Best Buy Store we passed a Walmart, a Kohls and a Marshals and I realized they are all just filled with NEW panties. I suggested that when we were finished at Best Buy maybe we should stop by the Kohls, since we do not have one in our town. I told him I wanted to look for new jeans. About half way i... Continue»
Posted by peggyacd 3 years ago  |  Categories: Fetish, Masturbation, Shemales  |  
581
  |  
80%
  |  2

Bi male and anal sex

Thru out my adult sex life I have always enjoyed having my ass teased and played with. 
Then I started dating a woman whom loved to tease a mans ass with her fingers, yes fingers where she quickly got me use to taking 2 of her fingers. 
Then one night things changed. After a hot night of wild sex, she slowed things down before excusing herself. But before she left, she rolls me over on my chest, which to me means she want to tease my ass. I hear her in the bathroom , toilet flushes and I hear her returning to the bed, straddling my legs, she racks her fingers up and down my back before she l... Continue»
Posted by rogue-1966 3 years ago  |  Categories: Anal, First Time, Shemales  |  
3898
  |  
98%
  |  23

stranger at a hotel

this is very true,few years back my mother passed away,left me a bunch of money,afterward,i now had money,but no f****y,so i was wild,parting,having alot of,hot man sex,by the way,im a chubby,very fem. tan, smooth,i look, act,an love to be treated,like a girl,an love it when a well hung horny man is turned on by me..i was at a riverboat casino,staying at a very nice hotel..i always,had plenty of very sexy,outfits an loved to dress up an leave the curtains,half open (pretending i didnt realize it)an just like a worm on a fish hook,sure enough someone would walk by an see me as i was,walkin arou... Continue»
Posted by burds67 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
1064
  |  
76%
  |  2

Xdresser Roxxi's black cock obsession Part 1

This is only a fantasy of mine at the moment however I hope one day it comes true .For a long time now I have been going to hotels and dressing up spending the night wearing various sexy outfits .Taking pictures of myself fantasizing about being a girl and what type of guys I would like and what I want them to do to me .After years of doing this I have worked out what really turns me on and off, this story is my fav fantasy .I'm very submissive when I dress up as a girl ,i want to be man handled ,to feel a mans smooth muscles ,the strength of a large black man .He would be over six foot tall v... Continue»
Posted by foxxiroxxi 3 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
338
  |  
87%
  |  1

Xdresser Roxxi's black cock obsession Part 1

This is only a fantasy of mine at the moment however I hope one day it comes true .For a long time now I have been going to hotels and dressing up spending the night wearing various sexy outfits .Taking pictures of myself fantasizing about being a girl and what type of guys I would like and what I want them to do to me .After years of doing this I have worked out what really turns me on and off, this story is my fav fantasy .I'm very submissive when I dress up as a girl ,i want to be man handled ,to feel a mans smooth muscles ,the strength of a large black man .He would be over six foot tall v... Continue»
Posted by foxxiroxxi 3 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
407
  |  
97%
  |  1

My meeting with trannymilf Sandy 54 part 2

So I see she said when she saw it rise underneath my skirt. She kicked off her right shoe and stroke my dick with her white nylonfeet on the outside of the skirt. It felt so good I started to groan! "Fuck me" I suddenly screamed! Not yet hun she said and smiled first I wanna undress you! Stand up she said! I did so and she took off my black leatherskirt then she stood up and took off my red bra and started too squeeze my big trannytits she took of her white dress and then her white bra so there we stood the two of us in only panties and stockings with garter belt she was dressed in white I was... Continue»
Posted by NellieTranny 3 years ago  |  Categories: Shemales  |  
656
  |  
100%
  |  3

a crazy night

I soon as i got my Dl (16)i would always leave on the weekends my house. I got out of a late movie and i started to drive to a friends house. I was waiting at the corner light when see two sexy ladies standing outside. they saw me stairing at them and one of them winked at me and waved. I parked my car across the street, and i crossed over. We said Hi and we all talk for like2 min, when they invited me to come inside. As we steped in and they closed the door, one of the ladies started making out with me while the other girl watched. the girl that was watching she pulled her skirt up and moved ... Continue»
Posted by lucifer696 3 years ago  |  Categories: Gay Male, Shemales, Taboo  |  
2872
  |  
72%
  |  3

Busted

The guy turned back and walked up behind me and whispered, "I like your panties."

I was so busted. I turned to him and said, "Excuse me?"

"It looks like those panties you're wearing are pretty sexy. Maybe you'd like to show me them."

My face burned with embarrassment. I tried to look away but couldn't.

"It's laundry day. They're my girlfriends," I said.

He laughed loudly. "Bullshit."

"Alright. They're mine. I like to wear women's panties. Big deal."

"Hey it's cool. I think it's hot. I'd really like to see what you're wearing under there."

I smiled and blushed. "Oh yeah?... Continue»
Posted by koolstuff 3 years ago  |  Categories: First Time, Shemales  |  
2123
  |  
96%
  |  17

My meeting with tranny milf Sandy 54 part 1

Wanna tell you about my meeting with Trannymilf Sandy 54!

I met Sandy through an add in a pornographic magazine I was 23 then so she was 31 years older than me. Wanting for long to meet a much older tranny beauty I got really excited when she agreed to meet me. We met in her apartment after I rang the doorbell a beautiful woman in her midfifties with a white dress long blond hair,white nylonstockings and white high heels opened the door. Her face had a heavy-makeup I was stunned by her looks. Welcome Nellie she said I guess you would like to change? Yes I said with a trembling voice and she... Continue»
Posted by NellieTranny 3 years ago  |  Categories: Shemales  |  
1072
  |  
78%
  |  5

paying to be used as a girl

i's been dressing up in girls clothes since i was 11. my mom's and my 2 elder s****rs suff. they'd caught me on several occassions when i was younger, but had thought it was a phase i'd grow out of. only now it turned me on too much to ever stop

Just recently i'd developed a new even more outrageous fantasy. now when i dressed i would fantasize about being used like a girl by a man....sometimes the fantasy would involve several men.this had come about ever since my mom had bought our first home computer. I'd spend hours when home alone watching tranny porn on the internet. i'd even posted p... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
1747
  |  
94%
  |  9

Book Store Bop By Cumhunger



A lady friend of mine Kelly had been riding to work with me for the past week
and every evening on the drive home we past an adult book store.I mentioned
something to her in passing that the lot always seemed to be full.She looked at
me with a mischivous grin and said... yeah all the guys who's wifes won't suck
their dicks frequent the place.

I've been there a few times to suck a few myself she giggled,what I said to her
in shock? Not straight laced Kelly,she's the demure type I never would have suspected to frequent this... Continue»
Posted by cumhunger 3 years ago  |  Categories: Anal, Shemales, Voyeur  |  
2288
  |  
91%
  |  6

Letting Debbie Out

Ok, this story has some explicit sex stuff, so if you shouldnt or dont want to read naughty material then please go away.

Also, I write because I want and like to. I am not a writer. Typically I write in one sitting and just do a stream of thought. I rarely edit.
But please let me know what you think. I will hopefully improve over time. And if i get enought replies that i need to edit or do something differently maybe I will.

Luv Submissive/Slutty/Sissy Sally

"I'm not sure what to do" Don said to Sam, "It sounds fun and all, but I really dont typically hang out with my employees"
"... Continue»
Posted by GreyMan44 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
769
  |  
83%
  |  8

a real cd explains what cd on cd sex is like

alot of "strait" guys love shemale porn.I was one of them.Pre-internet I discovered shemale porn but it was hard to find.I had girlfriends but the sex was never great.like many i was more concerned with cumming to soon than actually enjoying myself.Plus,as a porn watcher my fav was anal.My girlfriends fav...not so much.after 25 years i realized that i was most unhappy when i had a girlfriend.even then I had bought and worn nylons and enjoyed anal dildo play alone.then came the net.and i bought a wig,shoes, and some makeup.I had wanted to be with a cd.I didn't realize i could be an attractive ... Continue»
Posted by tran1001 3 years ago  |  Categories: Shemales  |  
1666
  |  
94%
  |  8

The Night With A Transgendered Angel pt.2

So,I stroked harder and faster till I couldn't take the pleasure anymore,then I blasted fat wads of my hot cum into her pink asspussy. She moaned in extacy as I she felt my load splurge into her. I pulled my semi hard cock from her ass slowly so I can watch as it leaks out. Being the little cum slut she is she ate every drop that came out of her freshly bred fuckhole. I sat in the chair naked and lit a cigarette,as I was smoking Steph got onto her knees and cleaned the pussy and cum residue off my member. I leaned my head back in amazement as she cleaned my cock. By the time I was finished wit... Continue»
Posted by yungn1234 3 years ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
839
  |  
100%
  |  1

Fantasy fuck

Sitting in the toilet cubicle I have been horny all day my cock is semi hard and I run my finger over the eye as pre cum oozes from the slit, I taste it's salty flavour as I strain the p*o out mmm wish there was something going in rather than out! There is activity in the next stall and I see some flesh through the gloryhole as someone sits down, with my cock stiffer than ever and my heart beating I look through to see a beautiful tranny pull her satin panties down and strOke her cock her fingers wiggle at the hole as a invitation, so I go for it and place my erectiOn through the hole , wow ho... Continue»
Posted by kawa696969 3 years ago  |  Categories: Anal, Shemales  |  
1179
  |  
87%
  |  2

My life as Daddy's sissy

Hello Daddy,

I would so love this life…

I wake up thinking of you, dreaming of kissing you, of sucking your cock, of feeling it fill my boicunt.

I spend all day preparing for you, so impatient to be with you. You are at work and I’m home, enjoying my role as your slut and maid.

I clean the house wearing pink sissy sweat shorts and a tank top, pink sneakers and pink socks. I want our home to be perfect for you, and I take pride in taking care of the house you work so hard to provide.

I then go to the gym in sexy little workout outfit. No one there cares that I’m a sissy anymore. ... Continue»
Posted by NancyRoseTV 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
1875
  |  
90%
  |  9