Categories
Sort By
Date
Languages
Search results
My first time with a tranny

My first time with a tranny

... I was very nervous and it was my first time I asked for a blowjob. She told me to drive around ... that it was my first time. She smiled and kept going faster. I knew she would try to rip me off taking ... district in my city where all the trannys were.

At the party we got extremely wasted and it was fun. We... Continue»
Posted by feinor11 4 years ago  |  Categories: Anal, First Time, Shemales  |  
6496
  |  
94%
  |  18

My first time as a bottom and with a tranny

... and I told her that I was looking for my first time, not only with a shemale but as bottom all ... .

And that's how I my first time as a bottom was. Hope you like it ... So this is the story about how i got my first experience being a bottom, and why... Continue»
Posted by Pepmeister 7 months ago  |  Categories: Anal, First Time, Shemales  |  
9609
  |  
100%
  |  10

A Steamy Photo Session with my wife

... A steamy photo session with my wife
Part 1
Hello mera naam hai Aseem, 35yrs aur meri ... saath saath nahane ke time hota hai, kabhi standing position mein, kabhi doggy mein aur zyadatar baath ... climax ko dabne nahin deti aur orgasm ke time pe sara dum laga ke chillati hai.
Marriage ke baad... Continue»
Posted by Tee_Rex 3 months ago  |  Categories: Anal, Hardcore  |  
18

Fucking my first tranny - Fun times with Jennifer

... something about it and I just didn't want to fuck a woman this time. I've been really curious about ... trannies for a while now, I once fucked a friend of mine when were fooling around (I should write ... a story about him too!), but the combination of tits, smooth ass and a cock would always catch my... Continue»
Posted by Sylf 9 months ago  |  Categories: Anal, First Time, Shemales  |  
3643
  |  
100%
  |  6

FIRST TIME TRANNY

... couldn’t help but slowly grab my cock, the feeling of pleasure intense.

Another note ... lost all sense and took my jeans, t-shirt and boxers off which I dropped to the floor ... guided it into my mouth, just the bell end at first.

“good girl, now get that tongue to work... Continue»
Posted by stig1963 6 years ago  |  Categories: First Time, Gay Male, Group Sex  |  
3435
  |  
93%
  |  21

first time with a Tranny

... My first tranny I had was back after I graduated from high school. I was working with her/him ... the car down and spit the cum out. First time for all, she was a virgin well so was I. She told me ... if she ever suck my cock again warn her so she can be ready. So weeks went by and now at that time she... Continue»
Posted by theho_1 4 years ago  |  Categories: Anal, Shemales  |  
4448
  |  
83%
  |  9

First Time With Tranny

... the story of my first experience with a tranny. Let me know and I will share my second experience! ... . Soon I was chatting with this hot asian crossdresser. She was about my age (21 or so at the time ... first time. Her cock was very nice, probably about 6" and fairly fat. Now she (her name was Sarah... Continue»
Posted by jay01973 6 years ago  |  Categories: Anal, First Time, Gay Male  |  
2831
  |  
94%
  |  10

my first tranny..................

... ," hello donnie, 'i'm ida. i haven't seen u here before." "i know," i said. "this is my first time ... kissed and i saw the time/ it was almost time for me to p/u my girlfriend from work so i cleaned up ... [iim donnie, i had just dropped my girlfriend of at shipyard to work graveyard shift. i wanted... Continue»
Posted by tvsucker4u 7 days ago  |  Categories: First Time, Hardcore, Shemales  |  
2481
  |  
89%
  |  2

My First Tranny Experience

... I was in my mid twenties when I first became attracted to trannys. This was before the internet ... .
I arrived on time at a small apartment block near the city centre. I was extremely nervous as I ... and there was soft music playing. She told me to lay face down on the bed. I did so and turned my head to watch... Continue»
Posted by mjam21 3 months ago  |  Categories: Fetish, First Time, Shemales  |  
2652
  |  
100%

My First Tranny

... xhamster page titled,

"My First Tranny". We corresponded through the dating site quite regularly ... wanted me to stuff her fat ass with my thick dick. Almost each time during these phone encounters ... to

make sure she would be there being that this would be our first meeting. It seemed that my dick... Continue»
Posted by ghostdawgg62 4 years ago  |  Categories: First Time, Shemales  |  
1109
  |  
96%
  |  7

My first tranny

... them and me. I may not have been with a tranny before my first but Im hooked now and love to fuck ... to her. Thats when I saw her cock for the first time. It wasnt very big but it still suprised me. I ... tranny lover. We fucked each other several times a day and night. I had not cum so much in so long... Continue»
Posted by wildbill975 3 years ago  |  Categories: Anal, First Time, Shemales  |  
4843
  |  
18%
  |  14

My first time with a tranny

... on the ground between her legs she guided me onto my knees and told me to suck her hard nipples. She ... then said she wanted to see if I could suck her big cock. I lowered my head to the glistening head of her ... lovely big penis and licked the tip. She pushed my head and guided the full thing into my mouth... Continue»
Posted by ross80 3 years ago  |  Categories: Shemales  |  
3370
  |  
25%
  |  1

my first tranny pt. 2

... a tranny dick in my mouth.

I blew her for a few more when she said she needed me to fuck her. I stood ... vibator in my ass several times but it was small. I always wondered what it felt like to get fuck ... was all the way in. I felt her balls on my ass. she was moaning the whole time & saying how tight I... Continue»
Posted by radec_24 4 years ago  |  Categories: First Time, Taboo, Shemales  |  
1133
  |  
96%
  |  3

First time with a tranny I met on grindr!

... in search of a tranny to fulfill my fantasies and finally I found one!

Her profile read "looking ... gonna waste my time, if you're not serious about meeting then delete my number" I didn't wanna miss ... by her dick pressing against my hole, she pushed harder and f***ed the tip in first, I thought she... Continue»
Posted by Datrap6 8 months ago  |  Categories: Anal, Hardcore, Shemales  |  
2151
  |  
100%
  |  5

my first tranny (pt. 1)

... you always remember your first time.


I remember my first blow job from an ex. (believe me ... . the first time I fucked a woman in the ass. & I'll always remember the first time I was with a tranny ... , thats another story.) the first time I touched a pair of tits. the first time I ever ate pussy... Continue»
Posted by radec_24 4 years ago  |  Categories: First Time, Taboo, Shemales  |  
2927
  |  
97%
  |  7

my first tranny pt. 2

... .

"fuck me harder. fuck my ass with your tranny cock."

"you like it, do you? you feel really tight ... a little tranny whore."

"fuck me harder! harder! fuck my pussy!"

thats all she kept saying. I ... first transexual. BROOKE! she will not be the last. I really love trannies..... ... Continue»
Posted by radec_24 4 years ago  |  Categories: Anal, First Time, Shemales  |  
1500
  |  
96%
  |  3

My Frist time with a tranny

... My Frist time it was back when AOL frist came out. I was in a miami chatroom and I met ... out throu pics what a tranny was. I must of been 13 at the time or so. She gave me her address ... at the same time. She asked me When I was leaving my age, and i Lied to her said i Was 18 , I asked... Continue»
Posted by lucifer696 4 years ago  |  Categories: First Time, Shemales  |  
1359
  |  
85%
  |  3

Finally, My First Tranny!!!

... and immediately went to my bedroom. She kissed me and opened my pants at the same time. When she had ... own cum off of her cock. It was really wild. These were the first time I have ever eaten cum. I ... I just came out of the doctor's office in downtown Philly from my 3 month check-up. I was pretty... Continue»
Posted by adw276 4 years ago  |  Categories: Anal, First Time, Shemales  |  
2939
  |  
96%
  |  12

My First Tranny

... machine, doing whatever she desires at the moment. When I felt my cock enter her throat the first ... time, and felt her tongue slide up my cock to the balls, and she sucked the cum right out like my ... my cock into her throat to the balls, Cheryl is sucking my nipples, first one then the other, I’m... Continue»
Posted by fishkiller 2 months ago  |  Categories: Fetish, Mature, Shemales  |  
4530
  |  
100%
  |  2

My sister, my first, the tranny

... by myself. She said my s****r would be checking up on me time to time. My s****r, Amy, lives about ... took my time and shaved my legs, my underarms and I trimmed my pubic hair into a neat triangle. I ... . All this time, my own cock was getting harder and harder until it was almost as rock hard as his I... Continue»
Posted by 6270daniel 1 year ago  |  Categories: First Time, Taboo, Shemales  |  
11652
  |  
98%
  |  15