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first time web hook up crossdressing dominatrix

first time web hook up crossdressing dominatrix

... crossdressing has always been my secret pleasure I even had a cache of out fits make up wigs ... on you can chat video post pics and meet guys to hook up with even couples and women were on here. I used ... other times I would just open my cam up and let anyone watch while I got wild and kinky for them. I... Continue»
Posted by lillolly 3 years ago  |  Categories: Shemales  |  
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First time hooking up with a shemale

... Well the first time I hooked up with a shemale was an e****t visit (night out, massage and the rest ... about it being my first time with a shemale. The night was over and she gave me a big hug ... the best of both worlds. I looked up a Brazilian shemale online and when I saw the pictures, I... Continue»
Posted by mensah9 6 months ago  |  Categories: Fetish, First Time, Shemales  |  
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My first time with another crossdresser.

... masturbating. and in the last story was my first time being with a woman wile crossdressed. now ... this story is about my first time with another crossdresser at the age of 18.

it was a friday night ... to come." we parted and i went out to my truck and got on the phone with johnny, set up a time... Continue»
Posted by sissypantyhoseboy90 4 years ago  |  Categories: Fetish, First Time, Shemales  |  
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crossdressers first time

... crossdressing slut for about a year!now i croosdress all the time, when i can. ... i first started to wear tights when i was 18,i was shocked when i first realised i loved tight ... panties and sheer tights. i was staying with my friends mother who was 65 at the time,she wore... Continue»
Posted by nylonfiona 5 years ago  |  Categories: Mature, Shemales  |  
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crossdressers first time with a guy!

... out again. I slowly made my way to my knees for the first time. with this nice big black cock ... a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from ... this simple thought I became massively aroused and started trying on her underwear, make up, and even... Continue»
Posted by cdnorwich22 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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First time web/cam sex

... time I try to reach out and talk to the earth. I was on the web for about a couple of mins when I ... ckeck it out for fun. What I discovered was I ended up seeing international dick from all over ... to day life, instead I ended up just clicking next to unburn my eyes of shlapping schlongs... Continue»
Posted by ffjester 3 years ago  |  Categories: First Time, Masturbation, Voyeur  |  
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First time crossdressing with another CD

... part of me. Any help would be great.

First Time Crossdressing with a mate part 1 ... , but ever since I dressed up like a slut for the first time, I couldn't stop thinking about meeting ... - attached, bi, recently got into CD and wanted to dress up with another CD for the first time. He... Continue»
Posted by kumquat 3 months ago  |  Categories: First Time, Shemales  |  
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First time dressing up

... the first time i crossdressed in my s****rs clothes, i just had to do it again. It was a week until ... thong, the blonde wig and make up bag from last time, I went back to my room and locked the door ... the vibrator and put the dress and everything else back in her room.

After that day any time i dressed up i... Continue»
Posted by Badassgirl123 1 year ago  |  Categories: First Time, Masturbation, Shemales  |  
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Beginnings: My First time as a crossdresser (PT 1)

... practice from borrowing my mom’s from time to time. When we got over to the mirror I took my first ... went jelly on me and I had a hard time staying up in those heels. Mikki wiped off her lips and smirked ... way up and down the shaft. This wasn’t my first rodeo so soon I was sucking like a pro, stopping... Continue»
Posted by sbobbi66 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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First Time Crossdressing with a mate part 1

... with guys before, but ever since I dressed up like a slut for the first time, I couldn't stop thinking ... the first round of drinks, he suggested we move up to the room. By this time I was feeling totally ... for the first time. He said that although he wasn't smooth, he was willing to become so if I would... Continue»
Posted by obm_cd 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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Crossdressers First Time

... knew I would be dressing more often and the other time I visited an e****t and wore panties ... unattached and had no need for a long term relationships but were happy to meet up for sex or go away ... closet full of ladies, clothes, lingerie, shoes , wigs and make up. I would indulge myself and dress... Continue»
Posted by maninnylons 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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My first time as a Crossdresser

... extra confident....and with a little Dutch courage, i decided to take up one of many invitations ... to him. At first i was sceptical. What would people think??
He assured me that it would be fine, its ... the the taxi drivers eyes on me. A middle aged man, looking at me, what was he thinking? Was my make up wrong... Continue»
Posted by mileslong34 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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Crossdresser Dominated For The First Time

... but not violently push me back down be i could get up.
“We’ve spent plenty of time with woman who were home ... to dress up and have fun while i was home alone. I went to my secret stash of clothes i keep in my ... wig, it fitted nicely as i applied my make up.

Once i looked like a sexy girly slut i went to go... Continue»
Posted by Badassgirl123 4 months ago  |  Categories: First Time, Group Sex, Shemales  |  
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school teen gay crossdresser first time sex

... and gathering up some courage I said. “you know I do it all the time” he quickly looked up and said ... , about to be a CD for the first time in front of another guy.

I was nervous, I reached ... it, admiring it and for the first time, with a lot of care I kissed it, I kissed the head of his cock, felt... Continue»
Posted by allisontranny 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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My first time crossdressing for a friend

... when i was younger as she didnt want a little brouther, i dressed up a few times on my own after ... swallowed it all down it burnt a bit but i loved my first tast of cum. I set back up and finished my ... had.


thank you hoped you enjoyed reading about my first time. if you liked it let me know and ill wright more.

debby r.... Continue»
Posted by deborah_riggs 5 years ago  |  Categories: Anal, Fetish, First Time  |  
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firsts time I'm seen as cd (crossdresser)

... him no one had ever seen me crossdress.... and that he would be my first encounter as a cd. I ... From a young age I liked dressing up in womens lingerie and clothing.... as I got older I grew up ... over weight a little and more so the older I got..... by the time I was I was in my late teens I had... Continue»
Posted by peta74 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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First time with a crossdresser pt1 True Story

... Ive been married for a few years now, but I always find myself straying from time to time to get my ... break one time when the wifie was away visiting her parents for a few days. I was good at the start ... in knots from nerves and excitment i mustard up the courage to meet at the hotel. He answered... Continue»
Posted by bjsmith94 5 years ago  |  Categories: Fetish, First Time, Shemales  |  
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first time crossdressing exp

... of drinks as it was our first bi experience, so he went upstairs to get changed and i got changed ... with wig/make up,we sat next to each other both quite nervous so he put on a tranny dvd ,it wasnt long ... it wasnt long before we had our blouses off revealing our lacy bras to each other i got him to stand up... Continue»
Posted by mumlover1960 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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First time fucking on web cam

... So I always had this fantasy that I wanted to fuck my girl friend on web cam in front of strangers ... had recently bought her. It showed off her tight little ass and pushed her tits up making them look ... . They asked to see my cock which was rocked hard in a tight pair of boxers. I obliged and he sprang up... Continue»
Posted by jasoncoyle 2 years ago  |  Categories: First Time, Masturbation, Voyeur  |  
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First time dominatrix

... up and started talking to her for quite a while. Then I noticed he took her aside in a small room ... distance. Then I saw the guy put his hands on my wife's hips, moving his hands up and down ... . It was lifting her short skirt up where I could see her panties. He then put his hands under her skirt, feeling... Continue»
Posted by mrrocknroll2012 4 years ago  |  Categories: Fetish, First Time, Voyeur  |  
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