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Teen Cross dressers First Man.

Teen Cross dressers First Man.

... female relationships before. I started to do a little bit of discreet <ddd>cross</ddd> dressing in my house about a year ago and thought about ... up in the air. He just looked and said "who <ddd>first</ddd>" and I actually wanted to feel a hard cock pumping my asshole ... ... Continue»
Posted by ClaireCD 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 704  |  
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Teen Cross dressers First Man.

... female relationships before. I started to do a little bit of discreet <ddd>cross</ddd> dressing in my house about a year ago and thought about ... up in the air. He just looked and said "who <ddd>first</ddd>" and I actually wanted to feel a hard cock pumping my asshole ... ... Continue»
Posted by ClaireCD 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2264  |  
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Cross Dressers First Time

... I had never had a sexual encounter with a <ddd>man</ddd> and saw myself as curious only.

It ... and enjoyed the films of some hot <ddd>cross</ddd> <ddd>dressers</ddd> I stroked myself through my panties but ... hardening. It wasn't huge but for the <ddd>first</ddd> hard cock I'd seen in real life it ... ... Continue»
Posted by webbyhose 8 months ago  |  Categories: Anal, First Time, Gay Male  |  Views: 1798  |  
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3 Teen Cross Dressers Misadventure - Part 2

... a world of hurt.


What else could we do? I was the <ddd>first</ddd>. I took off my jacket and then practically before I even took ... thing we are fucked. Again the <ddd>man</ddd> handing the clothes told him to sit down and <ddd>cross</ddd> his legs. Finally it was ... ... Continue»
Posted by ClaireCD 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 477  |  
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3 Teen Cross Dressers Misadventure - Part 3 Final

... got off of me and I had my <ddd>first</ddd> view of the room since Sean’s <ddd>man</ddd> switched with one of mine. Brett was ... a couple minutes he flipped me over and said, “bitches cum <ddd>first</ddd>.”


I was almost fully hard but the pain prevented it. Out ... ... Continue»
Posted by ClaireCD 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 749  |  
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3 Teen Cross Dressers Misadventure - Part 1

... and on our 6th drink or so we headed out, <ddd>first</ddd> to grab some snacks at the gas station across the ... ... Continue»
Posted by ClaireCD 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 466  |  
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My first man Fuck buddy.

... is dating a wonder woman. When her and I <ddd>first</ddd> meet she would suck my cock anytime I wanted ... I think I would be getting naked with another <ddd>man</ddd> none the less be wanting to have ... me back to hardness so I could try my <ddd>first</ddd> <ddd>man</ddd> pussy.But that will be another ... ... Continue»
Posted by mycocknurass 2 years ago  |  Categories: First Time, Gay Male  |  Views: 2931  |  
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A Cross-Dresser's tale

... was “becoming a <ddd>man</ddd>.”

It was about this time…timelines get fuzzy because of the booze…that I saw my <ddd>first</ddd> she-male ... -up my marriage.

I do believe that a lot of us <ddd>cross</ddd>-<ddd>dressers</ddd>/she-males/Trannys have the XXY syndrome, as I unprofessionally ... ... Continue»
Posted by prairieFreak13 1 year ago  |  Categories: Shemales  |  Views: 904  |  
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Slut bi cross dresser

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

We ... you. But you have disappointed me. Letting a <ddd>man</ddd> cum in your ass on the <ddd>first</ddd> date, I’ll have to teach you some ... ... Continue»
Posted by pesty 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 3247  |  
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cross dressed virgin

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

We ... you. But you have disappointed me. Letting a <ddd>man</ddd> cum in your ass on the <ddd>first</ddd> date, I’ll have to teach you some ... ... Continue»
Posted by pesty 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2634  |  
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Party Surprise - First sex as a Crossdresser.

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

We ... you. But you have disappointed me. Letting a <ddd>man</ddd> cum in your ass on the <ddd>first</ddd> date, I’ll have to teach you some ... ... Continue»
Posted by SatincdAus 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2735  |  
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The Cross Dresser and The Big Fat Fuck

... said she was a woman trapped in a <ddd>man</ddd>'s body wear as I was just a ... "

(YES! YES! YES!)

For our <ddd>first</ddd> date Debbie gave me a tour of ... lesbian couples, straight couples even a few <ddd>cross</ddd> <ddd>dressers</ddd> here and there.

Debbie and I found a booth ... ... Continue»
Posted by loriannthetran 4 years ago  |  Categories: Fetish, Hardcore, Sex Humor  |  Views: 661  |  
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A Night with Mike (his first with a man)

... watching boy on boy sex and having his <ddd>first</ddd> ever blow job from a <ddd>man</ddd>, Mike and I needed a bit of a rest to ... It’s much more complex than you think.”

“So trannies and <ddd>cross</ddd> <ddd>dressers</ddd> are nothing new/”

“Nope, perfectly normal really. Speaking of which ... ... Continue»
Posted by daviea9 8 months ago  |  Categories: Gay Male, Masturbation, Voyeur  |  Views: 2382  |  
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First Time: Slick&tyg:Part 3.

... shop. It catered to big women and <ddd>cross</ddd> <ddd>dressers</ddd> I think because most of the clothes ... I wasn't ready for it to be my <ddd>first</ddd> time for sex. I had been feeling a ... wriggling into my pussy. Never had a <ddd>man</ddd>'s mouth ever been there... I was struck with sensations ... ... Continue»
Posted by tygress77 3 years ago  |  Categories: BDSM, Fetish, First Time  |  Views: 1555  |  
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How I Became a Cross Dresser

... his cock started pulsing in my mouth, and I felt the <ddd>first</ddd> hot squirt of cum hit the back of my throat ... that there are a group of men out there who loved <ddd>cross</ddd> <ddd>dressers</ddd>, and I knew I was going to spend the rest of my ... ... Continue»
Posted by kbking70 1 year ago  |  Categories: Fetish, First Time, Gay Male  |  Views: 1142  |  
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My First Time!

... I lived in at the time a lot of transvestites, transsexuals, <ddd>cross</ddd> <ddd>dressers</ddd> and their admirers would hang out on forth street ... bent over with my *** in the air anticipating my <ddd>first</ddd> *** *******. <ddd>First</ddd> Christine took some petroleum jelly from the jar on ... ... Continue»
Posted by cute_girls_with_dick 1 year ago  |  Categories: Anal, First Time, Hardcore  |  Views: 1632  |  
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A man anally molests a stranger on a crowded commu

... <ddd>cross</ddd> dressing, homosexual lifestyle," said Peter.

"My <ddd>cross</ddd> dressing homosexual lifestyle?" Not even an official couple yet, they were already having their <ddd>first</ddd> ... ... Continue»
Posted by fotisampini 5 months ago  |  Categories: Anal, First Time  |  Views: 3626  |  
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The First Step With Hope- part one

... about it being a tad sleazy; neon lights, with scantily clad <ddd>cross</ddd>-<ddd>dressers</ddd> in need of a shave hanging around the entrance etc.; ... I held out a hand instinctively and our fingers touched for the <ddd>first</ddd> time; there was a sharp jolt as static electricity stung ... ... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 588  |  
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LUST FILLED FUCKING OF YOUNG TEEN CUNT

... and he then slowly slid his massive grown <ddd>man</ddd> cock into her hot hairless <ddd>teen</ddd> pussy he gasped and then moaned out ... cock..take it cunt... you wanna mess with <ddd>man</ddd> cock <ddd>teen</ddd> you will get <ddd>man</ddd> cock" he said through clenched teeth in a lust ... ... Continue»
Posted by dewdrop 2 years ago  |  Categories: First Time, Group Sex, Taboo  |  Views: 4147  |  
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Cross Dressing play turned horribly wrong - fantas

... still horny and wasnt satisfied. I have tried a little bit of <ddd>cross</ddd> dressing before but I was feeling very horny and for some ... a bulge like my cock would make, this looked big.
The <ddd>first</ddd> <ddd>man</ddd> in the doorway was much more toned, I could see his ... ... Continue»
Posted by clevelandzj 1 year ago  |  Categories: Anal, Gay Male, Interracial Sex  |  Views: 2728  |  
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