Search results
3 Teen Cross Dressers Misadventure - Part 2

3 Teen Cross Dressers Misadventure - Part 3 Final

... start licking his ass clean. This was not the worst part as now I felt my panties being pulled around my heels ... ... Continue»
Posted by ClaireCD 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 699  |  
97%
  |  3

3 Teen Cross Dressers Misadventure - Part 2

... were handed to me."Now the wig,sit down and cross your legs faggot." "Slim, your turn." They handed him a bra ... man handing the clothes told him to sit down and cross his legs. Finally it was Sean's turn, same as before ... ... Continue»
Posted by ClaireCD 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 438  |  
94%
  |  1

3 Teen Cross Dressers Misadventure - Part 1

Two friends and I decided to take a trip to upstate New York for a weekend of skiing and some messing around. We were friends since elementary school and have been dressing in our s****rs and mothers clothes for over a year and then play around with each ... ... Continue»
Posted by ClaireCD 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 390  |  
80%
  |  1

Teen Cross dressers First Man.

... female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought ... I wasn't gay; although I did fantasize about shemales ever since I started cross dressing. He looked at me and said, "what do ... ... Continue»
Posted by ClaireCD 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2145  |  
92%
  |  9

Teen Cross dressers First Man.

... female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought ... I wasn't gay; although I did fantasize about shemales ever since I started cross dressing. He looked at me and said, "what do ... ... Continue»
Posted by ClaireCD 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 672  |  
100%
  |  2

A Cross-Dresser's tale

... being Fiona and now realize that she is a real part of me --- part of my mind, body and soul.

I dress in my ... fuck-up my marriage.

I do believe that a lot of us cross-dressers/she-males/Trannys have the XXY syndrome, as I unprofessionally call ... ... Continue»
Posted by prairieFreak13 2 months ago  |  Categories: Shemales  |  Views: 731  |  
100%
  |  4

Be careful what you dream of Part 3

... The third part in a series of bad science fiction--

Jean squirmed as the ... , your third genders--the ones you call she-males, transsexuals, cross dressers, transvestites.”
“What about our women? How do we know you ... ... Continue»
Posted by prairieFreak13 9 months ago  |  Categories: Shemales  |  Views: 407  |  
40%
  |  2

First Time: Slick&tyg:Part 3.

... an adult toy shop. It catered to big women and cross dressers I think because most of the clothes were for larger framed ... other days.

I have just uploaded the photo from Slick & tyg part 3. One of the few pics I got to keep. It is ... ... Continue»
Posted by tygress77 2 years ago  |  Categories: BDSM, Fetish, First Time  |  Views: 1548  |  
100%
  |  7

One Weekend

... I thought it
would be like. I felt my skirt rising up.
Part of me began to worry about what was bound to ... town. He was
bisexual, single and experienced with a thing for cross dressers. I asked him to come over and he
refused. His argument ... ... Continue»
Posted by pr1456a 8 days ago  |  Categories: First Time, Shemales  |  Views: 1350  |  
100%

cross dressed virgin

... was at work. I also loved tranny porn or porn where cross dressers were involved. I loved the idea of a cock in panties.

... fuck you”.
I was shocked. Was this a line I wanted to cross?. Without hesitation I said, “I never thought you’d ask.” I had never ... ... Continue»
Posted by pesty 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2514  |  
38%
  |  14

Slut bi cross dresser

... was at work. I also loved tranny porn or porn where cross dressers were involved. I loved the idea of a cock in panties.

... fuck you”.
I was shocked. Was this a line I wanted to cross?. Without hesitation I said, “I never thought you’d ask.” I had never ... ... Continue»
Posted by pesty 7 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3151  |  
98%
  |  17

How I Became a Cross Dresser

... that there are a group of men out there who loved cross dressers, and I knew I was going to spend the rest of my ... ... Continue»
Posted by kbking70 8 months ago  |  Categories: Fetish, First Time, Gay Male  |  Views: 1137  |  
98%
  |  8

TAKE ME HIKING (A gay tale)

...
Everybody applauded and there was some more jostling between a few cross-dressers who had obviously taken opposite sides.
Jamie took advantage ... they watched the couple start to copulate.

In the other part of the woods, Danny and Bob were engaged in ... ... Continue»
Posted by mib14 1 year ago  |  Categories: Anal, Gay Male, Voyeur  |  Views: 769  |  
92%
  |  7

The First Step With Hope- part one

... about it being a tad sleazy; neon lights, with scantily clad cross-dressers in need of a shave hanging around the entrance etc.; as ... ... Continue»
Posted by midsummerman 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 560  |  
87%
  |  2

Teen in a Towel - Part II

... me. She said, "Yeah, but I want to REALLY thank you!"

Part III to come. ... Continue»
Posted by goinstrong 1 year ago  |  Categories: Hardcore, Masturbation, Mature  |  Views: 842  |  
100%
  |  3

Teen in a Towel - Part I

... drink!"

I wished her a good evening, then returned to my room.


Part II to follow. ... Continue»
Posted by goinstrong 1 year ago  |  Categories: Masturbation, Mature  |  Views: 981  |  
88%
  |  5

When She became He

... my boyfriend, even that was a loose term. The first part was true, in two ways, he had a cock, therefore a ... And a gentle squeeze................

I had never really thought about 'T Girls', cross dressers or even Shemales, they had never crossed my path, ... ... Continue»
Posted by chchboy 1 year ago  |  Categories: Mature, Sex Humor, Shemales  |  Views: 959  |  
100%
  |  5

Willows transformation 1

... Then in June things changed dramatically. I'd kept some magazines showing cross dressers, and jerked off with them. I always hid them, until ... preliminaries are over, and it's time for the entertainment part of our evening!" I shuddered with the sound of her ... ... Continue»
Posted by stig1963 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2070  |  
97%
  |  2

Alice 1

... I heterosexual? well sort of , I like pretty girls whether they are cross dressers like us, or real ones’
‘When I first saw you, I thought ... you our heartfelt thanks’
‘Thank you Andrew, it is only part of my job’
‘I hope to speak to you again before ... ... Continue»
Posted by ratty9uk 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 3148  |  
100%
  |  6

SISSIFIED

... "Sissy Suck". It started to play. All the cross dressers, shemales and transvestites in it. Some were in some state ...

He could hear that both were laughing as they left.


Part 2

After his step s****r and his friend left, he whimpered into ... ... Continue»
Posted by stig1963 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1537  |  
96%
  |  12
Advertisement
Remove All Banners

Related Premium Scenes