Chapters tagged sissy

by Coy-toy

Chapter 10

Moaning out at the incredible skills of the latex covered trap, you feel your balls start to tingle as your need to cum increases. The little slut can tell, and clamps around your balls as her lips continue her work. Soon as you wriggle from the overpleasure and the inability to...

by Coy-toy

Chapter 3

As a guy you are hardly intimidating, standing just under 5’6 with a lean frame. The only part about you that isn’t skinny is your unusually wide hips, giving you a more feminine frame than you ever wanted. In fact, many seem to mistake you for a girl sometimes... which always tu...

by Coy-toy

Chapter 5

She smiles as she begins to go over the rules. “Well this competition is very simple. The first to cum loses. So your objective is to make the other gurl cum before you” Taken aback by all of this, you focus your first question on the gurl part. “Um... I’m sorry, but I’m a guy”...

by Coy-toy

Chapter 8

After applying a decent amount of makeup and styling your hair, the gurls pull out a skimpy latex schoolgirl outfit. With a poofy white collared blouse, a black tie, knee high white socks, white panties, and a black skirt that is so short it looks more like a belt, the entire ens...

by Coy-toy

Chapter 9

“Can’t decide? Well since you chose to be a cooperative little slut... I arranged something special for you” Mistress Alex laughs. You smile nervously, not sure what she means as she leads you by your tie to a entrance. “Wait here for when they call for Slut, and come out.” She l...

by Coy-toy

Chapter 11

After hearing your options, the cupcake sounded like the easiest chance for a win. And though you’d never had sex with a Femboy before, as long as you won it felt like it wouldn’t matter. You ask Penny if you can have a go at him, to which she responds “of course! Here, we have t...

by Coy-toy

Chapter 16

You try to flail at a moment you think he won’t expect, but the veteran Femboy was ready, and used it against you. He got you on your back, his panties bulge pressing against your face in a pinned 69 position. You whimper into his groin and having another guys cock separated from...

by Coy-toy

Chapter 20

The next day you wake to an exhausted body, with a very sore jaw and ass. It takes you a minute to will yourself up enough to truly open your eyes, and are puns then you remember the night before. After that debaucherous last round, much was a blur. You had somehow got dressed a...

by Coy-toy

Chapter 21

Opening the email, you see Penny’s message. “Congrats on such a well received match! You are already on your way to being a fan favorite.” She attached a photo of you mid debauchery, covered in cum while you are lifted up riding her cock. You barely remember it, but see your cum...

by billybobjenkins362

Chapter 11

You hear a door slide open. Panicked, you look over your shoulder to see two figures, one masculine and muscled, one feminine and slim, silhouetted against and hidden door. "Wait! Let me try again! Please-AAAHK!" You scream as a heavy hand pulls you up to your feet. "Didn't you...

by billybobjenkins362

Chapter 12

The man hooks a finger in your mouth and pulls your head back so you are to look up at him. He towers over you and looks down with soft hungry eyes. "Hmmm. Those are some dick sucking lips." His voice is like velvet. "She's titillated at the very thought" The women has li...

by Sparkee23

Chapter 8

“Ok Matt, since you are being so brave, and I couldn’t help but notice your interest in my story, I dare you to become our latex sissy for the night!” You are shocked at the boldness of their dare, but you only live once, and you are surrounded by friends, so what’s the harm? Yea...

by Sparkee23

Chapter 9

You are handed a strange outfit, one that makes you wonder but you begin to dutifully abide by the terms of your dare. You put on the lace panties and latex garter belt, and the black latex garters which both feels restrictive and not at the same time. The contradiction gives you...

by Coy-toy

Chapter 10

Tony holds up a mirror for you, and you finally got to look at how stunning you are. In the mirror staring back is a drop dead gorgeous if extremely kinky latex maid. Your cock strains more against its cage as you see the reflections hands roam up and down the shiny body. All the...

by Coy-toy

Chapter 11

Even turned on as you were though, you still had that mental barrier of ‘isn’t this kinda gay?’ Holding you back. That was, until your horned up brain came up with a work around. “I’ll tell you what. I’ll be your willing maid, serve you to the best of my abilities... on one cond...

by Coy-toy

Chapter 4

Behind the fiery redhead was a leashed and embarrassed teenager. Short and skinny, he would just be an average if not scrawny 18 year old boy if it wasn’t for the slutty maid dress. This embarrassing outfit was accentuated with fishnet stockings, locked Mary Jane heels, and a fri...

by Coy-toy

Chapter 6

Emma sticks her tongue out, and pushes you playfully as she evades with “now now Cory, would little old me ever plot something nefarious? Any-who, lets start with classic smash brothers!” You grimace at her, trying to figure out what she could be plotting, but are disrupted as N...

by Coy-toy

Chapter 8

If you were in your right state of mind, you would never agree to that deal. Just for the chance of cumming in this sissy’s toying mouth, which you could probably do anyway if you really wanted, you would possibly give up complete control to your wickedly sadistic friend? You sho...

by Coy-toy

Chapter 9

“So the bet will not be against me, but my little sissy here. If you beat the twerp at the game of my choice, I’ll have my sissy release you long enough to cum before I lock you up again. But if you lose like I suspect you will, you have to do any one thing my pet wants. What do...

by Coy-toy

Chapter 7

“Ok the games begin now! Though Cory, I gotta say would a good sub be on the couch?” You give her a glare at first, knowing she is living this situation. You hop of, getting on your knees outside her foot as your competition is inside her legs. “What no apology? You must want t...