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Ilive406's Stories | xHamster

A Weekend Transformation

Once when I was a young teen, my parents decided to go away for the weekend – Friday to Sunday night – and left me at home with my sister as babysitter. She was allowed to have her friend Dolores over as long as there were no shenanigans. So on Friday night, after dinner and after my parents had left, we three were ensconced in the lounge room, watching TV. I hadn’t noticed the two girls were whispering and giggling. Then my sister Alice pointed at me and said: “He wants to be a girl.” Dolores spluttered with laughter. “How do… Read more

Posted by JayneBrayne 5 years ago 17

Role Model: Transition of Sienna Grace

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Posted by SidneyGray 6 years ago

HOW TO HAVE A PROSTATE ORGASM

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Posted by SidneyGray 6 years ago

My First Dildo Play (GIFs) Re-upload

Hi Horny Sluts, Daddies, Masters, and Mistress Re-uploading my GIFS from the Galleries i posted it got removed, for some reasons? anyway i can't make another galleries so i'll just post them here for you guys, I hope you guys enjoy P.S the white thong and temporary tats was a gift from Corgasm, great stuffs =) Please don't remove xHamster! i Love You! please love me back!! ( lol ) https://media.giphy.com/media/l0Iyk3OWRead more

Posted by TiffanySecrets 7 years ago 87

My Fantasy 1

Jenny and I were friends since high school. She is super cute; was on the dance team with a ballerina body, short blond hair/blue eyes, tall. I was a swimmer, have a thin, cut build that I think she found pretty sexy. We dated for a while, but didn't stay together as we both went our separate ways to college. I think she may have suspected that I was at least bi when we were dating as I didn't want to constantly have sex with her as her previous boyfriends did. When I came home this summer after my freshman year, we met up for lunch. I had changed quite a bit during my first year in college… Read more

Posted by sissydanny21 7 years ago 16

How I Became a Sissy 4

After my first real experience, I could think of nothing else but his cock. I couldn't even look at him during swim practice without getting immediately aroused, which, turns out everyone knows when you're wearing a speedo *hehe*. In the locker room it was even harder (no pun intended) as I couldn't help looking at his tight smooth body, perfect bubble butt, luscious cock. I had to stop showering after practice with the other guys because I couldn't keep it together. He knew right away I wanted his cock all the time, but we had to be discrete. When my roommate was gone, we would occasional… Read more

Posted by sissydanny21 8 years ago 18

Truth or Dare: 1st Sissy Explorations and Fucking

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Posted by sissymissy00 8 years ago

My first and only foursome (so far..)

This happened years ago when in was college… of course a bit of alcohol was involved... youth and alcohol made for an amazingly crazy combination. With alcohol having been involved some of the details are a bit hazy but they are accurate to the best of my recollection as I had put much of it down in my journal/blog that week not wanting to forget that night. It was in my 3rd year of college and I was seeing a guy for a few months. His name was Val and he was one of the first guys I had been with at the time when I started a… Read more

Posted by UnDressed2Thrill 9 years ago 28

Dressed For Threesome

My wife and I enjoy an open and honest relationship, she's been aware of my cross-dressing and how wearing lingerie really turns me on, hell, it turns both of us on! What she didn't know about me was how much I crave cock when I am in gurly mode. All that was about to change. My wife and I had talked about me sucking and getting fucked by another man's cock before, usually as she fucked my pantied ass with her dildo. "Would you like it if this was a real cock" she would ask as she slowly slid the dildo in and out of my ass and stroked my cock. At first I used to just giggle and say no but… Read more

Posted by kgbcd 11 years ago 11

How I Became A Sissy 3

After my first orgasm with a dildo, i realized I wanted nothing more sexually but to be a girl. I fantasized constantly about everything girly: getting up in the morning in a little frilly nighty, spending hours on makeup and painting my nails, silky smooth skin from careful shaving of *everything*, shopping all day trying on cute outfits, sexy outfits and lingere, going to ballet class in a pink tutu and tights...... Not only did I want to do all those girly things, but I became turned on primarily by boys and imagining myself with them. I still watched the occasional straight porn, but no… Read more

Posted by sissydanny21 9 years ago 26

How I Became A Sissy 2

.......after that first afternoon, everything changed. I would play dress up any chance I got. I kept my body shaved and grew my hair a bit longer so I could part my bangs and hold the rest of my hair back with a flowery, sparkly harband. Sooo cute. I experimented with makeup styles: subtle eyeshadow with shiny pink gloss to thick eyeliner with dark red lipstick, always with lengthening mascara. By the end of a month I had modeled all her panties, bras, stockings, tights, swimsuits, ballet and dance costumes, dresses. I think I looked cutest in a tight, low cut, yellow sundress with pink fl… Read more

Posted by sissydanny21 9 years ago 15

How I became a Sissy

when i was in jr high and hs i used to get turned on and masturbate to girls in tights, frilly dresses, pinks, purples and fantasized about having sex with them. pretty typical boy. my life changed when i decided to see how i looked as a girl. my older s*s was my size and i snuck into her room while she was away one afternoon. as soon as i opened the panty drawer, my cock got hard and i was hornier than i had ever been. i sorted through all of the panties: boy shorts, lacy thongs, pink, light blue lacy, tight black hip huggers and chose a lacy pink thong to try on. i slid it over my legs a… Read more

Posted by sissydanny21 10 years ago 44