Twink Stories

289 results
Orientation
Length
Source
Infinite Scroll

Her Crewcut and Masculinization

by Trapper_Jock_Mcintyre on Sep 12, 2017
Transsexuals & Crossdressers

It had to stop. She was spending far too much money on her hair with frosting and tints. The bill for her nails was ridiculous. It was as if she picked the most expensive place in town. And lingerie! For what she spent, we could have bought an entire Victoria's Secret. It was always spend spend spend, yet, she never once lifted a pretty finger to even try to...

Sissy Gets Outed

by nancyvasquez on Sep 16, 2017
Transsexuals & Crossdressers

I was married for 3 years before I finally got caught. It happened when my wife went through my notebooks and found all the gay fantasies I had been writing about. The story she found was one I had just written. It was about a young guy who applies for a modeling job at a gay magazine called TORO. In the story, The young guy goes to the modeling session, w...

First Time for Everything

by bootwhore666 on Sep 15, 2017
Transsexuals & Crossdressers

At the time I was living in Paris and on sheer whim, I decided to go to Amsterdam for the weekend. I thought to myself, "what better place to act out my fantasies than in Amsterdam?" I packed some of my slutty clothes. I decided on my slutty cowgirl outfit complete with flannel top, jean skirt, white mask, cowgirl hat and my favorite pair of boots, black vin...

Perfect Couple

by saqazij on Sep 16, 2017
Transsexuals & Crossdressers

Michael Michael should be first described as how he looks. He is a typical blonde. He is almost 5.8 ft with brown and little long hair, blue eyes like sapphires and pink lips. The lips are so pink that it looks like he is wearing lipsticks. The most striking feature of his face was his cherubic smile. He can melt million hearts with it. He was lean but not...

Master Noah's War Ch. 01

by RedShambhala on Jan 8, 2018
BDSM

"Master Noah's War" is supposed to become a long-running "series" with a multitude of characters, and both maledom as well as femdom elements. The series will be largely, albeit not exclusively, heterosexual, and also involve queer elements, bisexuality, a twink/ish femboi character, etc. Furthermore, I imagine a kind of low fantasy setting with a few Gore...

Sigma Omega Sigma Ch. 07

by SEVERUSMAX on Jul 3, 2018
BDSM

Fucking Jessica was beyond delicious. That Beta knew precisely what to do with my cock and how to pleasure it to the max. She sucked it, rode it, and was used by it hard from behind plenty before I finished with her. She certainly creamed herself more than once, though she had to bite her bottom lip and fight the urge to scream her release as I pounded her m...

Girlfriend's Encouragement

by PleasureAddiction on May 16, 2018
Erotic Couplings

Editor's note: this story contains scenes of gay male sexual content. * I was lucky, for a number of reasons. I had a gorgeous girlfriend, one who stood 5'3 and had a slender build but having been such a strong emotional support for me, she was much larger than that. Shelby had dark brown hair on tanned skin, piercing green eyes that were always full of l...

Belle South

by Oldfarticus on Sep 14, 2017
Erotic Couplings

After awhile, all location photo shoots look about the same. You've seen them all, done them all, and are bored silly. Half the time, you're just going through the motions, wondering when you will get to go back home this time. Now and then, however, you hit one that stands out in your mind for a very long time. So far, this wasn't it. In days past, this gi...

To Protect and To Serve

by John_the_Author on Sep 12, 2017
BDSM

Author's Foreword— This is my eleventh offering to Literotica and her readers. You're invited to leave a public comment and access my profile to see what other goodies can be found in my archives. Enjoy! * * * * * * * * * * * * * * * * * * * * * * * * * * * * It was a boring evening to be out on patrol. Thursdays usually were. Officer Jose Ocala t...

The Basement Ch. 02

by FiveDots on Dec 24, 2019
Transgender & Crossdressers

I received a text the next evening. 'Hey dude, come down here and check this out.' Not yet ready to confront him with a revenge plan but not willing to ignore him either, I traveled down the stairs to the basement. My roommate had used the threat of exposing my questionable internet history to coerce me into letting him shrink me temporarily to pleasure him...