Categories
Sort By
Date
Languages
Search results
cross dressed virgin

Judith on the Cross

... , like the Middle Ages. Then, hands roping him to the cross, dressed only in some cloth wrapped round his waist. Then, hauling ... they don't stint on the detail work either. Helpers dressed in Roman legionnaire outfits, bare-back whippings before they go ... ... Continue»
Posted by cdod 4 years ago  |  Categories: BDSM  |  Views: 622  |  
100%
  |  3

night out all dressed up....

... cross dresser what happened the other evening was quite amusing to me, i had spent the entire day around my home, dressed ... nothing to do so I got all dressed up, wearing white satin panties, bra ... she said there was a cross dressed bloke and two randy females ... ... Continue»
Posted by andicoral 9 months ago  |  Categories: Lesbian Sex, Sex Humor  |  Views: 447  |  
100%
  |  1

Cross Dressers First Time

... .

What I kept quiet and has since I was young was that I cross dressed. I now had a locked closet full of ladies, clothes, lingerie, shoes ... clients and my broker talking to me unaware that I was dressed up as (even though I say so myself) a sexy milf. By ... ... Continue»
Posted by webbyhose 1 year ago  |  Categories: Anal, First Time, Gay Male  |  Views: 1804  |  
100%
  |  8

Cross Dressing to go to Girls' School

... taken up enthusiastically by all present. They didn’t know that I cross dressed as often as I could and so instead of being embarrassed ... to wear.

I went to the girls’ school early next morning dressed as a boy but with the female undies on. I was smuggled ... ... Continue»
Posted by daviea9 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 2547  |  
100%
  |  2

Cross dressed slavery

... dark severe bangs. She was short, and very buxom, and dressed in her own clothes she was VERY attractive. I may ... Japanese men in with absolute confidence. They were young and dressed in sharp black suits, with black sunglasses. They looked surprisingly ... ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1665  |  
98%
  |  12

Caught cross dressed part 1

... any stubble that might grow during my 'dressed' phase. I lined my eyes with Kohl ... predicament!

"We can all see that you prefer being dressed as a woman... no, as a tart, and ... we say otherwise! We'll keep him dressed up as our fully feminised, crossdressed, ... ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2932  |  
98%
  |  8

caught cross dressed part 2

... strong adhesive.

"She's ready now ladies. Shall we get her dressed again?" Alice prompted the others.

"Yes, let's!" Helen replied. ... face me, and I was shocked to see them both dressed in leather 'Catwoman' outfits... their faces masked... their bodies ... ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1791  |  
98%
  |  7

caught cross dressed part 3

... I closed my eyes, all I could see were replays of myself, dressed like a whore, being strapped to a padded sawhorse while it fucked ... shots of the entire scene so you could see me dressed in my full outfit, from my glittery makeup and pigtails ... ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 662  |  
100%
  |  3

cross dressed cocks

... was the bulge in his panties i was interested in. I was dressed in pink thigh highs red strappy heels pink panties and ... me like a good whore i would walk him to the car dressed as i was. i was terrified yet it was a rush at the ... ... Continue»
Posted by amitokinki 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1558  |  
98%
  |  4

A Cross-Dresser's tale

... , to work and heal.

I don’t remember cross-dressing at this time, but I was drinking. ... I was not alone.
I remember getting dressed and going into transgendered chat rooms, swacked ... a huge, thick cock spreads my virgin boi-pussy and finally fills me ... ... Continue»
Posted by prairieFreak13 2 years ago  |  Categories: Shemales  |  Views: 1089  |  
94%
  |  18

JASON CAUGHT IN MOM'S PANTIES

... laugh. "Chad... you know me and...
well... I'm still a virgin... don't you know that is
still true; remember our conversation ... between them from
their discussion after she found him cross-dressed in
her underpants and bra.

Knowing she had to ... ... Continue»
Posted by famlover66 3 years ago  |  Categories: Mature, Taboo  |  Views: 7559  |  
86%
  |  14

My real story

... One was of him full length and dressed. From what I could see he was ... cross dressed when I had the chance and I LOVED the idea of 3 somes and 4 somes and I told him I was a virgin ... . He was particularly pleased that I cross dressed and liked 3 somes. He ended ... ... Continue»
Posted by lookin02 2 years ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 2137  |  
100%
  |  15

My real story

... One was of him full length and dressed. From what I could see he was ... cross dressed when I had the chance and I LOVED the idea of 3 somes and 4 somes and I told him I was a virgin ... . He was particularly pleased that I cross dressed and liked 3 somes. He ended ... ... Continue»
Posted by lookin02 2 years ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 659  |  
96%
  |  5

The Surprise Vacation

...
emotional trauma was much more severe.

My wife fucked my virgin ass - my cunt, she called it, her throat
clogged ... I was to become. In my mind, I was already a woman, not a
cross-dressed fag slut.

She walked up behind me, encircled my waist ... ... Continue»
Posted by klammer 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 4194  |  
100%
  |  2

The Surprise Vacation

...
emotional trauma was much more severe.

My wife fucked my virgin ass - my cunt, she called it, her throat
clogged ... I was to become. In my mind, I was already a woman, not a
cross-dressed fag slut.

She walked up behind me, encircled my waist ... ... Continue»
Posted by klammer 1 year ago  |  Categories: Masturbation, Masturbation  |  Views: 826  |  1

Sissy Sarah’s Story

... in me, yes I cross dressed when I had the chance and I LOVED 3 somes and 4 somes and I told him I was a virgin to this sort of ... he was close to Guildford. He was particularly pleased that I cross dressed and liked 3 somes. He ended by saying he would keep ... ... Continue»
Posted by cocksucker1966 1 year ago  |  Categories: Shemales  |  Views: 1565  |  
58%
  |  5

Surprise

... emotional trauma was
much more severe.
My wife fucked my virgin ass - my cunt, she called it, her
throat clogged ... I was to become. In my mind,
I was already a woman, not a cross-dressed fag slut.
She walked up behind me, encircled my waist ... ... Continue»
Posted by klammer 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 10820  |  
86%
  |  4

Cross Dressing play turned horribly wrong - fantas

... I have tried a little bit of cross dressing before but I was feeling very horny ... the bed contemplating fucking my own ass whilst dressed like a horny little girl.

I showered ... this white trashy slut is an anal Virgin.. hehe we will have you gaping like ... ... Continue»
Posted by clevelandzj 2 years ago  |  Categories: Anal, Gay Male, Interracial Sex  |  Views: 2750  |  
45%
  |  17

Chastity Belt Roulette

... have much choice for now. I
better get dressed.

After taking off my clothes, I was ... thought you
had, you are not cross dressed for our pleasure. Personally, seeing
... been
taught the art of fucking a virgin asshole.

The pressure gave way to ... ... Continue»
Posted by klammer 1 year ago  |  Categories: Anal, BDSM, Fetish  |  Views: 3008  |  
75%
  |  2

Chastity Belt Roulette

... have much choice for now. I better get dressed. After taking off my clothes, I was shivering ... thought you had, you are not cross dressed for our pleasure. Personally, seeing you ... been taught the art of fucking a virgin asshole. The pressure gave way to a ... ... Continue»
Posted by klammer 1 year ago  |  Categories: BDSM, Fetish, Taboo  |  Views: 1081  |  
69%