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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: 610  |  
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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 in ... got dressed she said that Christine had always been spoilt, them started to laugh about it, as she said there was a cross dressed ... ... Continue»
Posted by andicoral 5 months ago  |  Categories: Lesbian Sex, Sex Humor  |  Views: 443  |  
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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: 1800  |  
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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: 2524  |  
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Cross dressed slavery

... Japanese men in with absolute confidence. They were young and dressed in sharp black suits, with black sunglasses. They looked ... subject, but his natural desires, to be dressed like a woman, and especially to be dressed like this, in sweaters and wool, are ... ... Continue»
Posted by stig1963 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1666  |  
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Caught cross dressed part 1

... my predicament!

"We can all see that you prefer being dressed as a woman... no, as a tart, and a slut... so, if you ... fully feminised until we say otherwise! We'll keep him dressed up as our fully feminised, crossdressed, transvestite slut and sex ... ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2902  |  
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caught cross dressed part 2

... 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: 1777  |  
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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: 659  |  
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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 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1554  |  
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A Cross-Dresser's tale

... and cross-dressing porn would perhaps alleviate some of my cravings and desires. But as I began to watch the videos, usually dressed ... towards the inevitable night when a huge, thick cock spreads my virgin boi-pussy and finally fills me like the little cum ... ... Continue»
Posted by prairieFreak13 1 year ago  |  Categories: Shemales  |  Views: 1081  |  
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JASON CAUGHT IN MOM'S PANTIES

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

Knowing she had to ... ... Continue»
Posted by famlover66 2 years ago  |  Categories: Mature, Taboo  |  Views: 7313  |  
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My real story

... me, yes I 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 to this ... he was close to me. He was particularly pleased that I cross dressed and liked 3 somes. He ended by saying he would keep ... ... Continue»
Posted by lookin02 2 years ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 2137  |  
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My real story

... me, yes I 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 to this ... he was close to me. He was particularly pleased that I cross dressed and liked 3 somes. He ended by saying he would keep ... ... Continue»
Posted by lookin02 2 years ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 655  |  
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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 11 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 4309  |  
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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 10 months ago  |  Categories: Masturbation, Masturbation  |  Views: 634  |  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 9 months ago  |  Categories: Shemales  |  Views: 1465  |  
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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 8 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 10537  |  
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Cross Dressing play turned horribly wrong - fantas

... cross dressing before but I was feeling very horny and for some reason decided today was going to be the day I dressed ... 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 ... ... Continue»
Posted by clevelandzj 2 years ago  |  Categories: Anal, Gay Male, Interracial Sex  |  Views: 2746  |  
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Chastity Belt Roulette

... we
explain why you are dressed this way. Contrary to every thought you
had, you are not cross dressed for our pleasure. Personally ... was if she had been
taught the art of fucking a virgin asshole.

The pressure gave way to a burning as she stretched ... ... Continue»
Posted by klammer 1 year ago  |  Categories: Anal, BDSM, Fetish  |  Views: 2961  |  
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Chastity Belt Roulette

... we explain why you are dressed this way. Contrary to every thought you had, you are not cross dressed for our pleasure. Personally ... was if she had been taught the art of fucking a virgin asshole. The pressure gave way to a burning as she stretched ... ... Continue»
Posted by klammer 9 months ago  |  Categories: BDSM, Fetish, Taboo  |  Views: 1086  |  
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