Chastity Boyfriend Stories

60,738 results
Orientation
Length
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Infinite Scroll

Howie Hangs

by justincbenedict on Aug 7, 2019
BDSM

Giulia ran her long dark nails up and down Howie's swelling cock. He was hanging just above the floor with his hands tied to the rafters of the barn. Giulia and Howie loved going up to his parent's country place. Howie's folks summered in Miami now, and so the farm was deserted. Giulia shook her thick ash blonde hair and re-adjusted her sunglasses. She to...

Platonic Chastity

by Cagedcompliance14 on Aug 24, 2020
BDSM

Platonic Chastity * Author's note: I wanted this story to be a bit slower and explore the real life implications of a femdom relationship on a man and woman. This first chapter is mainly setup for the remainder of the tale but I hope the reader enjoys it nonetheless. CH 01 Taylor sighed in frustration as he looked at his cell phone, he had overslept again...

Connie Throws a Party

by cmorehead on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. In a previous story, I described some of the kinky activities enjoyed by my boyfrie...

Neighbourhood Terror to Sissy Pt. 08

by Fibaro on May 20, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Chapter 9 Once off the bus Mark snuck to his house as good as he could. Hiding behind bushes and hedges whenever he spotted someone. He really didn't want to run in any of his neighbours with this big pink shopping bag. It would mean nothing but trouble since he realised f...

Black Wife Cuckolds Black Hubby

by Samuelx on Sep 12, 2017
Group Sex

Watching my Somali Muslim husband Omar Suleiman's soulful brown eyes, I smiled as I began sucking on Tyson Jacobsen's long and thick Caribbean dick. Omar Suleiman, a short, slender yet muscular, forty-something Black man of Somali descent with light brown skin and a cool bald pate, watches as I, his darling Somali-American wife, suck off another man. That's...

The Perfect Man Ch. 02

by Freakboy80 on Sep 18, 2017
BDSM

Please read the "Perfect Man" before reading this. This story is a continuation of that story. * It had been a week since Justin had seen Sandra. He talked to her on the phone everyday, but she had refused to see him until another week had passed. When he would ask to see her she would always remind him of what she had told him the last time they saw each...

An Ever Changing Story

by Helenthemaid on Sep 16, 2017
Transsexuals & Crossdressers

Caught Out and Permanently Punished I was wearing a ultra short black leather mini skirt, a tight leopard print low cut top, which revealed my cleavage entrapped by my pink lacy bra (with matching panties). The straps of my 6 inch leopard stiletto heels were securely padlocked around my ankles. Recently I had been often going to the local park dressed in...

The Roommate Pt. 12 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Chastened, Josh/Lori nursed her wounds for days, and little was said between her and Miranda, except when the dominant asked how Lori had opened her chastity when with Cassie. "I bought a master key on the Internet," answered Lori brightly. "Actually, my penis is getting a little irritated by the plastic over such a long time." "Give me the key. It obvious...

Olivia's Liberation

by aweatherly on Sep 16, 2017
Fetish

"Are you even listening, Liv? Seriously!" My focus suddenly snapped back to my workmate, Nicole, who was waggling her hand in front of my face. My thoughts scrambled as I tried to recall what she'd just said, while I was too preoccupied thinking of what I planned on doing that evening. "Yeah, sorry. God, I'm so out of it after that meeting. What did you sa...

Black Women Cuckolding Black Men

by Samuelx on Sep 16, 2017
Interracial Love

Gleefully I spank my ebony sub's ass while thrusting my strap-on dildo deep into his hole. The tall, skinny Black dude moans deeply. Smiling, I continue fucking him. My name is Valerie Blackstone, and I'm a five-foot-eleven, curvy and sexy Black woman of Jamaican descent living in the City of Ottawa, Ontario. My slaves call me Mistress Africana. I'm one of a...