Sort By
Search results
my first time with three shemales

my first time with three shemales

... three of them i sad i would die trying so we got into my car and headed to there condo where ... me back over and sat on my cock and road me like a bucking bronco until i came for the third time ... it was shemale night close to midnight when i saw this very tall gurl walk in with some friends she... Continue»
Posted by jaygomez1958 3 years ago  |  Categories: Shemales  |  
  |  36

My First Time with a Shemale

... of my head, and, for the first time, I took a guy’s dick fucking my face.

Just before she was about ... I had watched porn for a long time, graduating from straight porn to videos of shemales, falling ... . However, as much as I fantasized about being with a shemale or cross-dresser, I never thought it would... Continue»
Posted by TSfanxxx 2 years ago  |  Categories: First Time, Shemales  |  
  |  4

My first time with a shemale

... enough my ears still start glowing with excitement. It wasn't the first time that I sucked cock ... , neither the last time. But it was the first time I got fucked in my ass and it was a hell of a ride.

I ... it at first, so she took my one hand and led it under her mini skirt, rubbing it against her crotch... Continue»
Posted by HOLY-SMOKE 4 years ago  |  Categories: Anal, First Time, Shemales  |  
  |  11

My First Time with a Shemale

... her stomach and the sight of it instantly made me shoot my own cum into her ass! For the first time, I was cumming in another man’s ass!
... themselves while men jacked off. Nevertheless, she started her van and so I started my car ... station and I pulled in behind her. I got out of my car and approached her driver’s window…still... Continue»
Posted by omnisexual2 1 year ago  |  Categories: Lesbian Sex  |  
  |  1

First Time Having Sex With A Shemale

... this was the first time something when into my asshole as she pound my ass i can hear the cum i shot ... background she said Thailand. I was like that was one of my three guesses and she was like really i ... in my mouth so she pull out i was sucking that dick for the third time that night then as her dick... Continue»
Posted by TheGhost08 4 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
  |  22

My first time with a BBW Shemale turned into a thr

... mine. I was in shock that my first shemale experience was with 2 hung, fine, BBWS and how fast ... head. I had secretly masturbated to shemale porn since I was in my early 20's and had the best orgasms ... as it can go. She starts to fuck my mouth and Im in passions throat and Im in BBW shemale heaven. Ms... Continue»
Posted by Champdick 2 years ago  |  Categories: Shemales  |  
  |  9

My first time with a shemale(True Story)

... This is a true story about my first experience with a shemale.

I was sitting around ... told her that i would definitely come back and see her again.

That was my first experience ... the house the other day horny as fuck. My usual girl that i call on when i get that way had f****y in town... Continue»
Posted by wild_wolf_03 11 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  16

First Time - Surprise Shemale

... on a rubber and then sat back, as for the first time in my life I began to give head. I started ... , i'd seen many shemales on my PC, via webcam, in pics and video. But I've never, ever been so ... in close to whisper. This time she said "would you like me to fuck you?"
"Yes" was my sub second... Continue»
Posted by hungrymanx 1 year ago  |  Categories: Anal, First Time, Shemales  |  
  |  3

First Time Shemale Encounter

... . Not knowing and spanish i tried to tell the owner what i wanted. If it was going to be my first time ... in. My lucky day! The manager, who spoke english offered me two women since it was my first time. I ... and the other took my shirt off. Im standing naked while two beautiful shemales are looking at me. i... Continue»
Posted by iLoveShemales12 4 years ago  |  Categories: Anal, First Time, Shemales  |  
  |  3

First time fucked by a shemale

... buns, I can tell this is your first time at this and I promise I'll be gentle." she said. My boner ... to say. I had fantasized about being with a shemale many times, but never thought about actually ... start to harden beneath the t-shirt and bra. She started pulling my shirt off. "Wait," I said, "I'm... Continue»
Posted by surferboy_ibiza 4 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  8

first time with a shemale

... Well this is my first story i have wrote so bear with me and comment on what you think...

well ... in my mouth and ass but i wasnt attratced to men jusst the cock so i decided to find a shemale. i live ... had in my butt. this was my first cock but i had tried some toys but not many... (always remeber im... Continue»
Posted by wildmanxd 3 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
  |  2

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 e****t a call and asked to see if she was available for night out and it must have been my lucky... Continue»
Posted by mensah9 1 month ago  |  Categories: Fetish, First Time, Shemales  |  
  |  6


... I remember the first time I found myself in bed with a shemale. I had just broken up with my ... to fall in love with them - they just want sex with a straight dude!"

Well, my first thought was "Fuck ... with a woman. When I told my buddy, Bob, he told me he knew just where to take me to solve this. So... Continue»
Posted by madnessx 3 years ago  |  Categories: Anal, Masturbation, Shemales  |  
  |  7

My first encounter with a shemale!

... not to bite. i tried my best. it was the first time i had ever seen an erect cock let alone touch one! i ... and started wanking to shemale porn every now an again online. i have always been interested with my ... years ago and my first stop was amsterdam. after a few hours of roaming the red light district i... Continue»
Posted by onceuponanas 3 years ago  |  Categories: Anal, First Time, Shemales  |  
  |  6


... eyes made contact. My first reaction was that she was just being friendly, but I was very mistaken ... talked the small talk for a time, all the while I stammered over my words. Feeling my nervousness ... with her beautifully raging hard cock. I blew the hottest load of my life with a hot shemale cock deep... Continue»
Posted by fukkerguy 2 years ago  |  Categories: First Time, Shemales  |  
  |  5

My first time with a girl - Part Three

... yes, I got out of bed and stood near her.
My top came off first, then my bra. Louise was right ... ideas. I wanted to lick Louise like they did in the videos I saw. I wanted to put my hands inside ... snuggled up to each other. There was nothing in that usually, though that time it meant a lot to me... Continue»
Posted by sarahyork 5 years ago  |  Categories: First Time, Lesbian Sex, Voyeur  |  
  |  3

First time with a shemale

... judgement in the sex world that I had loved since I can remember jerking off for the first time.
I ... am, walking and finding my self say "No thank you" to girls that I knew I would never ever meet ... if my memories are playing games, but I remember her really really cute and splendid... As usual she... Continue»
Posted by joelo 3 years ago  |  Categories: Shemales  |  
  |  4

First time with a Shemale

... First off this is a true story. I lost my virginity at a young age so sex is always been something ... usual for me. As far as how I lost my virginity... thats another story. I have always dated women ... and situations because of being soooooo "openminded", heres my story...

Bella and I were... Continue»
Posted by trannincestluva 5 years ago  |  Categories: Shemales  |  
  |  5

My first time witha a shemale.

... I was holiday in Spain with my friend and his Mum when i was 17, we didnt have any problems getting ... and me and my friend ending up in a club quite the worse for wear, a girl was dancing against a pole ... and keeped looking at me so i look backand maintain eye contact, she danced in my direction so i... Continue»
Posted by JD85 4 years ago  |  Categories: Anal, First Time, Shemales  |  
  |  2

Unexpected Three-way and My First DP

... An Unexpected Three-way…a true story.

I have been estranged from my f****y for a long time ... it but a lot ran down my chin onto my T-shirt.

Andre was moaning oh fuck oh fuck, damn girl you ... and they started fucking me. I was trapped. I was having my first double penetration with two black men I had... Continue»
Posted by CatnJammer 2 years ago  |  Categories: Anal, First Time, Interracial Sex  |  
  |  6