Sort By
Search results
my older cross dressing friend

my older cross dressing friend

... trim build... almost a woman's shaped ass. My cock started getting very stiff. Tim, "Well ... rated. He slipped his hand around my balls "follow my lead", Tim coaxed. I felt his ... . The suction was perfect, I could feel my juice flowing into his mouth. "mmm, tasty ... ... Continue»
Posted by TenderLoins 2 years ago  |  Categories: First Time, Shemales  |  
  |  5

Bi MMF, FemDom, Cross Dressing, Cuckold

... were queer, especially you!", she said to my friend. She then walked up to us, my friend now covering his cock with a throw pillow ... too good to be true, but there I was, fucking my friends cross dressing ass. If you saw him from behind, you would swear ... ... Continue»
Posted by chrissylegs 8 months ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  4

How I started Cross Dressing and other first times

... always said was the true cause of my cross-dressing. It was right around puberty, so ... around here when I had my first orgasm as well.
My friend across the street and ... runs in the bl**d!

As I had gotten older, I had more responsibilities around the house, ... ... Continue»
Posted by pantiesdave 2 months ago  |  Categories: Fetish, First Time, Taboo  |  
  |  2

Dogging - Cross Dressing and Porno

... the neighbours wife fitted an older fetish the “milf”, she ... explained that the pub was a cross dressing haven which peaked their interest.

At ... friend. Joan sucked my cock hard and pulled my ball sack from my trousers and squeezed my plums, releasing my ... ... Continue»
Posted by daveaverage 25 days ago  |  Categories: Anal, Group Sex, Hardcore  |  
  |  1

Cross Dressing, Pegging and the Promise of a Three

... session with Ann, the gorgeous older woman (we’d call her a MILF nowadays) who’d discovered my love for cross-dressing, things were quiet for a ... of watching two boys have sex. Do you think your friend might like us to have a threesome?” The idea appealed ... ... Continue»
Posted by daviea9 1 year ago  |  Categories: Fetish, First Time, Mature  |  
  |  2

Cross Dressing play turned horribly wrong - fantas

... horny and wasnt satisfied. I have tried a little bit of cross dressing before but I was feeling very horny and for some reason ... heavy black man, his cock covered in my lipstick ...his muscley friend continued on my ass... and he started with steady short ... ... Continue»
Posted by clevelandzj 2 years ago  |  Categories: Anal, Gay Male, Interracial Sex  |  
  |  17

My Cross-Dressing for a couple fantasy

... have found myself having a recurring fantasy of wanting to try cross dressing for a bi-sexual couple. Several years ago i did try ... up on their driveway i could feel my heart pounding in my chest and my nerves tingled throughout my body, just as i stepped out ... ... Continue»
Posted by marcusp1979 4 years ago  |  Categories: Fetish, Gay Male, Mature  |  
  |  3

Cross Dressing to go to Girls' School

... or something. But that didn’t have anything to do with cross dressing.

There was an all-girls school a few miles from mine ... to extract myself from the school grounds fairly easily. However my girlfriend was suspicious – she wasn’t the girl involved in ... ... Continue»
Posted by daviea9 2 years ago  |  Categories: Fetish, Masturbation, Shemales  |  
  |  2

my first cross dressing play time

... sucked my first cock the other day. i posted a ad on craigs saying i like to cross dress ... posted a few pics of me from my xhamster profile and actually got alot of replies ... while he would reach down further and stroke my cock for a few seconds. then i could ... ... Continue»
Posted by floyd1985 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
  |  5


... have a mom that is so sexy everyone wants to be my friend and I can ask them for anything as long as they ... lad quite big for his age and slightly older?
Yes that’s him he’s my best friend Mom
“ It’s up to you bring who ... ... Continue»
Posted by bobbyblue53 1 year ago  |  Categories: Mature, Sex Humor, Taboo  |  
  |  4

My first time

Her is a lil story for everyone during one of my early cross dressing experiences. Both my parents worked during the day and I didn’t feel like ... a lot so all the fabrics could rub on my hard cock. During my posing my bra strap had fallen down as I have no ... ... Continue»
Posted by kaos420 2 years ago  |  Categories: Fetish, First Time, Masturbation  |  
  |  3

Me and my Older s****r Lucy

... pistol in my fingers spraying against the Wendy house with Lucy looking on, giggling.
One day Lucy had her friend around ... Rubbing and thrusting her wet lips on to my tongue, making her cum instantly, my older s****r pussy juice sweet and tasty.
We went ... ... Continue»
Posted by nckboy 4 years ago  |  Categories: Taboo  |  
  |  14

Learning form My Older s****r's


After a few years, I was very accustomed to doing what my older s****r told me to do. So when I was summoned to ... to undress completely once again, this time in front of my s****r's friend(s) whereupon I was fondled by other curious girls. This usually ... ... Continue»
Posted by brianbigdogsmith 6 months ago  |  Categories: First Time, Taboo, Voyeur  |  
  |  2

Living with my Older s****r Lucy

This story follows on from; Me and my Older s****r Lucy which goes in to more detail about our early ... exploded, pumping torrents of hot creamy sperm in to my s****rs friend. I don’t know who came first but Jane and Lucy were ... ... Continue»
Posted by nckboy 4 years ago  |  Categories: Mature, Taboo  |  
  |  13

Story of my Life: My Brother's Friend Brandon


In the last story, I told of my first time masturbating. For two years that was ... particular night, my older b*****r Jacob (who at the time was thirteen), had his friend sl**p over.

His friend was a ... ... Continue»
Posted by v-a-gina 1 year ago  |  Categories: Sex Humor  |  
  |  3

my teen arse fucked by my older boss (gay)

... there was really nice , a girl called louise and an older

Women called karen .

I only worked thursday friday but he ... wrong with that ?

Me - true , but obviouslt your my boss and a friend of my mums that's all , it
Just feels a little wierd . ... ... Continue»
Posted by bigwillyuk 2 years ago  |  Categories: Anal, Gay Male, Mature  |  
  |  12

My wife , a old friend and new cockhold who is me

... ben go's on to say that my great uncle and a " friend " of his well be here in ... , I hear voices and I hear sarha laughing my uncle walks in and he has just a T-shrit ... up and it was my older cousin jon. we both we kinda were shocked my uncle says calm down ... ... Continue»
Posted by iceman56 3 years ago  |  Categories: Fetish, Group Sex, Hardcore  |  
  |  1

I'm hot for my older s****r

... on one of her juggs I began to run my hands all over my older

s****r's body, squeezing her ass and rubbing her pussy lips ... effort to stop me. So I

continued to saw my cock in and out of my older s****r's tight pussy, faster and

faster, our hips ... ... Continue»
Posted by adel5000 4 years ago  |  Categories: Hardcore  |  
  |  16

Me and My Older s****r

... she started to unbuttoned. Lucy is 28 and three years older than me and nearly six feet, size six to eight ... started to gyrate her fanny over my face.
This is it, my cock erupted in to my older s****r’s mouth and she is managing to ... ... Continue»
Posted by nckboy 4 years ago  |  Categories: First Time, Hardcore, Taboo  |  
  |  7

My son and his friend, the perfect MILF

... I relied smiling, remembering the incident well, as his son Gaza, my son's friend, was watching his father put his hand between ... stockings, as I kissed his friend welcome into our home, my eyes watching my sons contented face, my cunt was aching for the boy ... ... Continue»
Posted by MarieL 3 years ago  |  Categories: BDSM, Fetish, Group Sex  |  
  |  15