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My first time with another crossdresser.

My first time with another crossdresser.

... this story is about my first time with another crossdresser at the age of 18.

it was a friday night ... masturbating. and in the last story was my first time being with a woman wile crossdressed. now ... 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  |  
  |  20

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 1 month ago  |  Categories: Anal, First Time, Shemales  |  
  |  11

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 ... she wrapped around my waist, completing the Madonna look that was so en’ vogue at the time.
After ... at the time how hard it would be to get them off!) These she painted the same red as my heels... Continue»
Posted by sbobbi66 8 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  8

My first time with another girl

... gave my ass a squeeze as I past to get another drink. Most of the time I spent watching Tom and Sam. I ... playing around with others from the beginning of our relationship. John wrote about the first time him ... was willing to do.

The first few time we had sex with others people, I would be d***k, almost... Continue»
Posted by plez2tease 29 days ago  |  Categories: First Time, Group Sex, Lesbian Sex  |  

My first time with another woman

... of myself for getting her off first and for getting any woman off for the first time, as the grin spread ... . That was great for your first time. Heck! That was great for ANY time!”

She suddenly jumped up onto her knees ... , welcoming her touch there. Every time she passed over my bud, she slowed down as I moaned loudly... Continue»
Posted by _PussyManiac_ 1 year ago  |  Categories: Lesbian Sex, Masturbation  |  

My first time with another man

... as he pressed it on my ass.Or was it me pushing my ass on his cock as I received my first wank from another guy.And maybe more... ... and with a loud grunt,he came all over me.He shuddered a couple of times,then pushed my hand off his ... It was no big deal when my mate Mark came out as gay a few years ago. Most of us sort of knew... Continue»
Posted by jackelaine 3 years ago  |  Categories: Gay Male, Masturbation, Taboo  |  
  |  12

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 4 years ago  |  Categories: Anal, Fetish, First Time  |  
  |  27

First Time Crossdressing with a mate part 1

... about meeting another crossdresser for some horny mutual fun. I had been faithful to my girlfriend ... with guys before, but ever since I dressed up like a slut for the first time, I couldn't stop thinking ... 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  |  
  |  5

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  |  
  |  5

Crossdressers first time

... So let me begin and say this is my actual first time of being dressed in front of someone and my ... first time with a guy.
It all started when i was 21. I was in college but on christmas break ... and my friend pat was having a party. Living only 5 minutes away i said i would go. Party was small 5... Continue»
Posted by Missterious999 8 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
  |  3

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  |  
  |  7

My first time fucking another man (repost)

... fucking that it just received, I wasn't feeling any pain, only pleasure. So for my first time ... his cock. It felt awkward at first but then good to feel his cock sliding back and forth between my ... did. She gently slapped the head of his cock on to my tongue a few times and moved it back... Continue»
Posted by theintern 10 months ago  |  Categories: Anal, First Time, Gay Male  |  
  |  12

my first time with another guy..true story

... had to offer each time. I made sure the 2nd and 3rd time when i was going to cum he would pull my ... fishing. I got to the lake and in my favorite spot was a tall (6'6" about 150 pounds) skinny young guy ... definately so I got my chair, pole and tackle boc and set up. I asked if he was catching anything... Continue»
Posted by jdm3196 4 years ago  |  Categories: First Time, Gay Male  |  
  |  31

school teen gay crossdresser first time sex

... , about to be a CD for the first time in front of another guy.

I was nervous, I reached ... , 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... Continue»
Posted by allisontranny 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  33

The first time my gf was with another man

... place and I'd make sure it was well worth his time. He seemed confused and got my directions ... thought it was hot having my girlfriend with another man. He shot me some glances and seemed okay ... never been with another man before." My girlfriend replies, "Nope," unsure of how... Continue»
Posted by pith 5 years ago  |  Categories: Fetish, Interracial Sex  |  
  |  3

Another First Time Story

... This is another first time story as told to me by a friend. It happened about twenty years ago ... , fingered her, rubbed my cock on her clit. Shelly sucked my cock, swallowed my load several times ... will get to lose my virginity in some real pussy and I know Shelly has had this fantisy to be with another... Continue»
Posted by zimabean 1 year ago  |  Categories: Mature, Taboo, Hardcore  |  
  |  4

First time with another lad

... Back in the summer of 1987 the time was perfect to experience my first lads holiday. The 3 of us ... position yanked his cock out, put his throbbing bell-end between my lips and began to suck my first ... at the same time.
"Fuck i'm gonna cum" I shouted so loudly the whole of Lloret could hear, "in my mouth... Continue»
Posted by fufkina 1 year ago  |  Categories: Anal, First Time, Gay Male  |  
  |  4

Another First Time Story

... they have a huge holiday party at their office building. This was the first time I got to go as my parents ... . I had to pee like a race horse and the first time I went pee the bathroom was total chaos so I ... much to drink. My cock was getting hard as this was the first pussy I had ever seen. The redhead... Continue»
Posted by zimabean 1 year ago  |  Categories: First Time, Mature, Taboo  |  
  |  5

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 ... over weight a little and more so the older I got..... by the time I was I was in my late teens I had ... online and meet with them in a car the back of my car with me all dressed up as a cd. I... Continue»
Posted by peta74 2 years ago  |  Categories: Anal, First Time, Shemales  |  
  |  9

My first time with another persons shoes, my aunts

... The very first time I fucked another persons shoe was when I turned 18. Before that I had been ... doing it with my own shoes for years, but we will skip that for another story.

One day I went to see ... . I didn´t know what to do, I just had taken away her shoe from my nose but my cock was still half way... Continue»
Posted by merrell69 11 months ago  |  Categories: Fetish, Masturbation, Mature  |