Sissy Plug Stories

24,564 results
Orientation
Length
Source
Infinite Scroll

Eyes of Tessa Ch. 02

by XDrake on Sep 17, 2017
BDSM

Mistress had me bent over the bed, my bottom bruised from the cruel beating she gave me a few days ago. I was still sore, even her gentle pats of reassurance hurt as she secured the front of the chastity belt on me. She put a lock on the front and wore the key on a necklace around her neck. "You have been very good the last few days. Don't think I have not...

Master's Love

by BrazenVixen on Sep 17, 2017
BDSM

The house is clean, the kitchen is spotless and I wait naked, kneeling by the door. Master will be home any minute and he expects me to be right here, waiting, naked. I have been with Master for 6 years. He found me dancing at the Lounge. The first time I saw him, I had no idea that he would completely change my life. He always sat close to the stage, al...

An Ultimate Fatasy

by Firemutt on Sep 17, 2017
BDSM

I’m sitting watching the football game. You’re working in the den on the computer. The kids are up north at grandpas for the weekend. It’s Saturday morning, & it appears to be another boring day at home. But unbeknown to me you have other ideas. After closing the blinds to the rear sliding door & then locking the door, you innocently walk past me into the b...

An Evening at Home

by lilsubalex on Sep 12, 2017
BDSM

Hi, Please leave me comments and don't forget to vote! As with all other stories at literotica... adults only please! * i was kneeling between Your legs, facing away from You, naked wearing a loosely tied robe. As we watched a movie, the rosebud was lodged in my ass keeping my sexual imagination stirring and reinforcing my submissiveness. You brushed my ha...

The List

by ElleEss on Sep 12, 2017
BDSM

Master has written me a slut's to-do list. I'm to present to him tonight. I've slipped on my short plaid skirt and a low-cut top. I like to play dress-up. I leave myself bare so Master can lift my skirt and fondle me until I'm wet and begging for his hard cock, rubbing up against me beneath his clothing. I have a surprise for my Master. Tonight he breaks...

Punishment

by Blushingsub3262 on Sep 17, 2017
BDSM

PRELUDE I hear the sound of the door closing behind you and my heart skips. I've never felt this particular frisson of fear before, but this time is different. I provoked you to this; to this point of anger and frustration, to this point that has culminated in that most ambiguous and challenging of words in an M/s relationship. Punishment. The word calls...

I Shall Be Serving You

by crazygirl18 on Aug 16, 2017
Fetish

All characters in this story are fictional, over 18, and consensual. I tried to take some people's comments into consideration when writing this one, but descriptions of the characters are still minimal. Make the people you would like to see in this situation. Enjoy, comments are always appreciated. ***** I woke with a start as my phone buzzed loudly, lig...

Dollhouse

by Littlemissdoll on Sep 16, 2017
BDSM

Emma struggled against her restraints for the hundredth time. "P-Please! Please, Professor, let me..." A sharp sting on her back made her stop talking. "Little Princess Doll..." He started, his hand gently caressing her bare ass where he had just slapped her. "How many times do I have to tell you to be quiet?" "I'm sorry! I..." Another slap and she bit...

Barbara's Cuckold Story Ch. 07

by HOTMOM_BARB on Sep 16, 2017
Interracial Love

This is a true story by a drop-dead gorgeous mid-thirties housewife (so I've been told) who has been proudly black owned for the past three years. Many of the details may not be as graphic as you would like, but I am putting this together from three years of memories. The phone rang, once, twice, three times and then I heard James voice from the other end....

Submission is the Ultimate Pleasure

by StephaniePlayland on Aug 7, 2019
Transgender & Crossdressers

Another installment of Stephanie and Sir. There isn't much time to get ready. Luckily I keep part of myself shaved, so it's a quick shower. Take an enema and douche to clean myself out. A girl needs to be ready to receive. A little lube to help slide the plug into place I need to be nice and relaxed so Sir can fuck me. Next I tuck and tape my little clitty...