Plug Training Stories

51,411 results
Orientation
Length
Source
Infinite Scroll

Maggie's New Life Ch. 04

by sadkins116 on Nov 20, 2018
Illustrated

Editor's note: this story contains scenes of incest or incest content. This story was inspired by the recent news about the NXIVM secret society, DOS. The lead character, Maggie, is desperate to rejuvenate her marriage to her husband of many years. She is befriended by a couple who are members of the cult. By the time Maggie realizes what the cult really is...

New Ponygirl

by Boxlicker101 on Sep 14, 2017
BDSM

CAUTION: This story is nothing at all like the happy sex romps that I usualy write. The young woman doesn't feel too unhappy now, but things may get a lot worse for her. Madame Top Hat, as she was known to her associates, happily watched the new ponygirl in training as she strutted on the treadmill. The trainee was tall and young and beautiful, with chestn...

Violet's Anal Training

by Powerone on Sep 25, 2017
Anal

Michael sat in the chair as she entered. Powerone had described her perfectly, long black hair, green eyes, pale skin, very small hands and fingers, DD breasts and small hips. She had a gothic look to her, the black clothes standing out dramatically to her white skin. "What am I doing here?" Violet questioned, but she already knew the answer. Powerone had o...

Proud No More Ch. 04

by Red_Anticius on Jun 19, 2019
Celebrities & Fan Fiction

Chapter 4: Archmage Subjugated Jaina Proudmoore could no longer keep track of the days that passed. Time blurred as one session with the Pride Breaker blended with the next. In between her so-called training, she was given 8 hours to rest. But all too soon, she would be brought before the dreaded goblin tech again, and forced to take it up the ass for anoth...

Serving Miss Nikki

by incorrigiblesatyr on Sep 17, 2017
BDSM

The phone rang, waking me from a deep sleep. "Hello", I mumbled – half tempted to curse the caller on the other end of the line. Looking over at the clock, I saw that it was 1 AM and I had just barely gotten an hour and a half of sleep. "Wake up, pet – and be up here in a half hour. I want you wearing that thong pouch that I bought you and nothing else whe...

Putamia

by DoxyTrainer on Jan 15, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** This is not a "pure" BDSM story, I did not intend it to be. It doesn't follow the "rules" even though I know them well. This story needed telling and is only for entertainment. Comments are welcome. *** The ringer jolted me from sleep. "Who is it?" I flailed for my glasses o...

Let's Go to the Movies Pt. 01

by coquette_redux on Mar 2, 2020
BDSM

God, this plug is so fucking heavy. She shifted in her seat for the 300th time since climbing into the passenger seat. She'd already been wearing it for half an hour and she could only be grateful that he hadn't tasked her to do something like grocery shopping with the plug the plug in...again. But sitting on it for this long wasn't much more comfortable....

Day Two - Morning

by buxxxom on Sep 17, 2017
BDSM

Please read Day One for this story to make sense. Day Two-Morning A soft, unknown sound penetrated the barriers of my sleeping conscience. I awoke, slowly, limb by limb, and stretched each one to relieve the tightness in my body. Shivery tingles and strange aches in uncertain places served as a reminder of the previous day's ordeal. I woke, strangely comfo...

Anal Training Ch. 03

by Catchandrea2397 on Feb 3, 2020
Transgender & Crossdressers

Hello pet. Welcome back. Are you ready for the next stage in your training? Good. You're such an eager obedient pet aren't you? Such a slut. Today you are going to need the following items - Bra and panties - Stockings, ideally with suspender - Butt plug - Vibrator/dildo - Lipstick - Perfume You will also need plenty of time. I'm not going to...

Chronicles of the Special Stretch

by AngelPie4Mongo on Sep 14, 2017
Anal

CHRONICLES OF THE "SPECIAL" YOGA STRETCH My boyfriend/ live-in lover/ best friend of three years had mentioned anal sex many many times. We had tried it 2 or 3 times and had to stop because it was VERY painful for me! A few weeks ago, I had a short discussion with him that I didn't know if we'd ever be able to have anal sex unless I went through some "anal...