Boy "butt Plug" Chastity Literotica Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

Sensitivity Training Can Mean a Lot Ch. 09

by JimAner on Apr 25, 2018
BDSM

Introduction: This can be read as a stand alone story, but if you want to understand the Island, you should read Chapter 8 at least. It is probably best to read the entire tale, but it is not necessary. For those of you who are following the series, Beercan is not in this chapter, but he will be in all of the following ones. ***** A Week in Femdom Villa...

Cucked by Princess

by Subboi23 on Mar 10, 2020
BDSM

i glance down at my phone, still nothing. i shift in my chair and feel the plug in my ass push in a little deeper. The resulting combination of pain and pleasure causes my cock to strain in its cage. One simple movement and now my ass and dick ache. Such is life when you are plugged and locked in chastity while the woman you worship and adore is out on a dat...

Prime Merchandise

by RonWCB on Sep 15, 2017
BDSM

I've always believed that people should use whatever talents they have to their fullest ability. Some guys are born athletes; some excel in business or the stock market. Me, I've always had an uncanny knack for reading women, or more specifically, spotting submissive women. There are more of them than you realize. In fact many women don't even fully realize...

The Ten Game Pt. 03

by THEGREATDANE99 on Dec 17, 2017
BDSM

Hi all! Thanks for reading and please feel free to leave feedback! * Summary: -Sam and Marina get invited by their highschool friend, Catherine, to an exotic sex club -They pass the initiation test with the help of a red headed waitress named Audrey -Sam can't help openly bragging about the Ten Club to anyone that will listen -Trixie, a dominatrix from...

When You First Spoke to Me...

by MoodyFeline on Nov 6, 2018
Erotic Couplings

It would be safe to say that you have the sexiest voice I've ever heard. That and the fact that you're tall, dark and, well dorky-handsome? These positives help me cope with your inability to grow a beard. Man, you would kill in a well-groomed, perfectly shaped beard. Call me fickle, but physical attributes play a huge role in one's definition of attractive....

Keyholder's First Week

by exploring_couple on Apr 11, 2018
BDSM

It all started with a letter. Beth got a letter in the mail. She opened the enveloped and a pair of keys fell on the table. Her fiancé lived a few towns away and with work and kids, they didn't always get to see each other as often as they would like. Due to busy work schedules, she knew that it would be a full week until they could get together again. Just...

The Modern Boardroom

by sexualsituations on Aug 24, 2020
BDSM

Philip shifted nervously in his seat as the Board meeting dragged on. As the General Counsel, he had been through many such meetings before, but he was dreading the last item on the agenda this time. On paper, it was an innocuous update by the head of a new employee group called Talent Advocating for Change that included a presentation suggesting the standar...

Mama Mia Pt. 02

by grizzley123 on Jul 27, 2020
Fetish

This story contains many themes including cuckolding, gay sex, bsdm, incest and submission. If these are not your things, please skip. This is the second installment and it obviously helps to read the first part. The starting point here: I have just finished sucking off my temporary neighbor's cock. I have been set-up by my wife and her lover to be a submis...

Boy's in the Hood

by PBEnis on Jul 11, 2018
Fetish

After reading about and discovering male chastity, I wanted to try it, not as a lifestyle but more as a fun experiment, just to role play a little. I was a bit embarrassed but brought the topic up with my wife, Kate, to feel her out. She's a "whatever blows your skirt up" kind of woman and has always been willing to indulge my perversions and fantasies. "S...

The Office Boy Ch. 02

by Aussie Worm on Sep 25, 2017
BDSM

It had been a whole month since I was locked in my metal chastity belt. Samantha had been right, its comfortable but frustrating; sometimes you forget you are wearing it but at the same time you know its there. I constantly hope I will be released soon but Katrina hasn't hinted about it and I know better not to bring the issue up with her. At least she doesn...