Categories
Sort By
Date
Languages
Search results
My first time crossdressing for a friend

My first time crossdressing for a friend

... had.


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

debby r. ... when i was younger as she didnt want a little brouther, i dressed up a few times on my own after ... , in my mouth or do you want to fuck me? He said bouth that he can cun 3 or 4 times a night. I... Continue»
Posted by deborah_riggs 5 years ago  |  Categories: Anal, Fetish, First Time  |  
6923
  |  
95%
  |  28

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  |  
5767
  |  
24%
  |  20

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 ... teenage girl. Once I even dressed in her bra and panties while I sucked off my best friend ... she wrapped around my waist, completing the Madonna look that was so en’ vogue at the time.
After... Continue»
Posted by sbobbi66 1 year ago  |  Categories: Anal, First Time, Shemales  |  
2992
  |  
100%
  |  8

crossdressers first time

... panties and sheer tights. i was staying with my friends mother who was 65 at the time,she wore ... 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... Continue»
Posted by nylonfiona 5 years ago  |  Categories: Mature, Shemales  |  
1077
  |  
99%
  |  7

My first time as a Crossdresser

... eyes on me. This time i didnt feel judged. I was the only woman in this bar. My date quickly removed me ... and forth, i lowered down to my knees. My nerves kicked in, this was the first dick i was about ... first 69. Amazing feeling of a hard cock in my mouth and a tongue in and out of my hole. It was getting... Continue»
Posted by mileslong34 7 months ago  |  Categories: Anal, First Time, Shemales  |  
3214
  |  
100%
  |  11

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 ... bigger and much more wet. I felt no breath on my ass this time. instead I felt hands on my hips. I ... . he was in control of me, pounding away at my tight ass. it hurt so much at first but it started... Continue»
Posted by cdnorwich22 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
2512
  |  
97%
  |  7

my first time with my friend

... they were soon hard and enlarged. Each time I did this her body would rise up to meet my hand and she would ... to proceed slowly and gently down the outside of her thigh. After doing this a few times I brought my ... touch her pussy lips. I didn’t linger there the first few times.

When I thought she had relaxed... Continue»
Posted by iamsuperman007 17 days ago  |  Categories: First Time, Interracial Sex, Mature  |  
8943
  |  
89%
  |  2

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 ... . lighting a cigarette I open my laptop and log on to a crossdresser networking site im a member ... 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  |  
753
  |  
100%
  |  7

school teen gay crossdresser first time sex

... , held my breath and it a wonderful second my gay ass was being fucked for the first time ... , horny as hell and dreaming of my first gay experience since sitting in my new red lace thong ... afternoon jacking off in my new bra and panties and watching my first porno when it happened, I saw... Continue»
Posted by allisontranny 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
15446
  |  
97%
  |  40

Made My Friend A Crossdresser

... worked in same company and he was a friend of a friend. At that time I was crazy about my physique ... with awesome bubbly butts.

This started a few years ago when we met for the first time in India. We ... joining me in gym.

Few months later he moved to my apartment and we became good friends. We became... Continue»
Posted by ajbasu 2 months ago  |  Categories: Anal, First Time, Gay Male  |  
1160
  |  
100%
  |  2

First Time With My Friends Wife

... awoke with a hand on my cock. I was a little startled at first then I realized Mary was in the room ... are my friends wife, this is wrong." I tried saying that out loud to not only remind her it was wrong ... to whisper "fuck me" numerous times into my ear. The fact that she seemed to be so into it just made me want... Continue»
Posted by BadRonald 5 years ago  |  Categories: First Time  |  
1868
  |  
96%
  |  5

One of my friend first time

... I wanted to start writing by speaking about of my friend first time. She and I spoke a great deal ... know how she was dressed as she asked me on this before hand :)
She confessed it was the first time ... for her and even a little jealous she got to be so well prepared for her first time!

However she still... Continue»
Posted by Debbyzoo 1 year ago  |  Categories: First Time, Interracial Sex  |  
1961
  |  
100%
  |  5

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 ... another crossdresser for some horny mutual fun. I had been faithful to my girlfriend, but after... Continue»
Posted by kumquat 3 months ago  |  Categories: First Time, Shemales  |  
435
  |  
100%

First Time with my best friend Christine

... mouth. It was the first time a woman gave me a deepthroat. I suggested to her that we do a 69 so we can ... Me and Christine are friend for over 13 years. I move away to the US and I had not seen her ... a while and she was feeling very horny.

She suddenly lift her top and bra and said "See, my nipples... Continue»
Posted by dragonlove69 2 years ago  |  Categories: Anal, First Time, Hardcore  |  
3066
  |  
100%
  |  1

Crossdressers First Time

... as my alter ego Paula at least once a month and enjoy time being a sexy lady. The dressing relaxed me ... knew I would be dressing more often and the other time I visited an e****t and wore panties ... of lube in my ass.
“Time to lose your cherry Paula.”
He took his time entering me until I... Continue»
Posted by maninnylons 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
5766
  |  
100%
  |  4

Crossdresser Dominated For The First Time

... loosen a sissy with my fingers first, before i fucked them. But i can tell you're the type who can ... over on my back. He put me in missionary and entered my sore and cum filled asshole. He spent no time ... alone, my parents were at work and my siblings out somewhere. I decided it would be a good day... Continue»
Posted by Badassgirl123 4 months ago  |  Categories: First Time, Group Sex, Shemales  |  
3193
  |  
100%
  |  10

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 ... about meeting another crossdresser for some horny mutual fun. I had been faithful to my girlfriend ... crossdressing occasionaly when we had sex, so I felt comfortable telling her about my secret fantasy.

I... Continue»
Posted by obm_cd 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
2428
  |  
100%
  |  5

crossdressing with my moms friend

... back down on the bed. Linda next to me, still kissing me, she took my cock from the panties.
First ... Mom opened my bedroom door. she stood there in the doorway and stared at me obviously repulsed ... . after 10 or so seconds she closed the door and walked away.
i was mortified. i was kneeling on my bed... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
4256
  |  
26%
  |  18

First Time With Friends Mom

... with my friends hot mother. I was 18 at the time, and horny as hell and always on the look out ... that this was my first time being with an older woman and god damnit, I'd never had a blowjob that felt ... I've written a story so I've decided that my next one will be about my first sexual experience... Continue»
Posted by TheLantern 4 years ago  |  Categories: First Time, Mature, Taboo  |  
8530
  |  
96%
  |  9

First time with friend,

... My story is of me and my best c***dhood friend and if I ever get finished writing it spans 6 year ... .

Intro and background:

My friend Mike, names changed to protect all, is 4 years younger than me ... talking of his girl friend sucking his cock.
Mike told me that he didn't think my cock could be sucked... Continue»
Posted by JnEastTx 4 years ago  |  Categories: Anal, First Time, Gay Male  |  
1203
  |  
87%
  |  2