Dildo Training Stories

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Trapped and Trained Ch. 01

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often moving the same piece of furniture to what seemed like the sam...

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...

Comply Ch. 01

by mslv4Her on Sep 13, 2017
BDSM

I am awaiting your entrance. As you've commanded, I'm naked and kneeling in the center of the room. My head is bowed, my legs are spread, and I am very anxious. You have told me that my behavior during our last few encounters has not been as you'd expect and you plan to help me modify that situation. I'm not sure what to expect but can only imagine I will be...

Kellie Gets Cock Training

by Tropical_Passion_420 on Dec 10, 2018
Erotic Couplings

Kellie and I have been married for nearly 20 years now. We were married young with virtually no experience in relationships or sex. Prior to our two-year romance just after high school, we only dated a few people, and never went all the way with any of them. Although we had some sexual encounters we were actually virgins when we started dating at eighteen!...

Trapped and Trained Ch. 03

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

The next few days felt like a lifetime for me. I couldn't sleep at night - every time I closed my eyes, all I could see were replays of myself, dressed like a whore, being strapped to a padded sawhorse while it fucked me from both sides. Everything I ate and drank had a horrid aftertaste of that bastard's cum - it was as if that taste was permanently embedde...

Always Read Before You Sign Ch. 03

by Reaver90 on Apr 6, 2020
Transgender & Crossdressers

"Wakey wakey sleepy head," Paula said. Samantha groaned. "What time is it?" "It's seven in the morning," Paula replied. "It's time for your boosters." Samantha got up slowly and yawned. She felt the two pricks on her arm. "All done," Paula said. "I would let you sleep for longer. But I've got to go out." "To the office and do shopping, yeah?" Samantha r...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

Mastering Submission Ch. 15

by sdbnnc on Sep 15, 2017
BDSM

In the manner of Gregory Maguire, who provided us with a version of the childhood standard The Wizard of Oz through the eyes of the "wicked" witch, I have re-written my favorite BDSM story, Both Master and Slave, written by Martin Sharpe (published in 2001 by Silver Moon Books in Great Britain), from the point of view of the submissive, rather than the Maste...

The Priestess, or, The Ceremony

by theredheadboy on Jul 15, 2020
BDSM

The boy awoke, the morning light streaming in through the window on to his face, warming his naked body. Already the day was warm, the hot dry desert air causing the small room to be uncomfortably stuffy before the sun had yet fully risen. Today though, there was an electric current upon the air. Today was his eighteenth birthday. Today was the day of the gr...

Training Him to Take Dick Ch. 01

by magic_tantra on Sep 19, 2017
Fetish

Training My Stud Boyfriend to Take Dick! Ch. 01 My name is Belinda I am a college coed who loves sex with both girls and guys. I am a hot brunette with long black hair down to my butt crack with ivory white skin and piercing blue eyes. I have a nice shapely body and love my real 36 C breasts with strawberry sized nipples. I have a clitoris that protrudes fr...