Sucking The Headmistress' Clit Literotica Stories

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RTFM

by astuffedshirt_perv on Sep 26, 2017
Toys & Masturbation

Note: This story takes place in the near future. The toy in this story was inspired by a story on another site, "The Curator," and is used with permission. Google "Streetwalker Squid Stimulator Deluxe with Partner Play" to find it. Karen started to shake in her silken sheets as her orgasm hit. Despite being alone in her apartment, she instinctively grab...

Mrs. Shepherd Learns To Dominate

by harryflashman1970 on Sep 14, 2017
Group Sex

This is another sequel to and Observed Threesome and Foursome. This tale just about stands alone, but I think it'd be more instructive (and would be more arousing) to read the earlier stories. This story picks up immediately from An Observed Foursome before going off in another direction. Thanks again, for the comments, messages and ratings. It's very nice...

SOAR University Ch. 01

by AubreyWright on Sep 14, 2017
First Time

Izanagi dropped his backpack next to a desk in the back row. Low profile, he thought to himself. That's how he got through secondary school, and as his first day at university, why should that be any different? But, it would be different. Different for Izanagi and, he had to keep reminding himself, for everyone else, too. This was university, and not just...

A School Girl Crush

by Debbie on Sep 12, 2017
Mature

Gary was pissed off as the foreman informed him that he would be traveling to Auckland with two of the reps for their company to fix some chairs at a school in Auckland. They were leaving straight away as the school's headmistress had been on the phone complaining several times already. Gary had tried to get out of it but the foreman wouldn't take no for an...

A Visit to the Headmistress

by adoration on Sep 14, 2017
BDSM

I was 25 and randy, but I was also curious. Well, they say curiosity killed the cat, but in my case curiosity got me the cat. I'd better explain. It was about five years ago and I was just coming off a torrid affair with a lovely colleague, who had dumped me for a much older man, the bastard! The older man, not the lovely colleague. Sandra said that while...

#4's Auction Pt. 02

by LiseKLord on Sep 19, 2017
BDSM

As the Headmistress had promised the former #4 was prepared for travel the next day. But as she had also promised, the night after her auction had been one of unending pleasure. It began upon entering the Mistress' sumptuous suite. Still in her red catsuit the woman who had owned #4's life during training and now sold her to the highest bidder poured two fl...

The Desk Ch. 02

by fishophile on Sep 16, 2017
BDSM

[Note: This is a follow-up to "The Desk". Read that first if you haven't done so already.] 1 Chloe walked nervously up the garden path. It was a detached house on the edge of town, in one of the nicer suburbs. Despite the sunshine, she was glad of the long coat which kept away the breeze that whistled through the trees. And, of course, it also was glad th...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

Long Term Nudity Project 2035

by zoejoey on Sep 14, 2017
BDSM

Hi folks, Zoe here. I recently submitted a story in Exhibitionist/Voyeur called the 'Long Term Nudity Project' right here on Lit and I haven't yet decided whether I will continue with it. However, the scenario has opened my eyes to other interesting possibilities that I would like to explore a little before I make my final decision on continuing with the lad...

SSCG Ch. 05

by Crystal_Ash on Sep 16, 2017
BDSM

Chapter 5 -- A Hunch About Lunch The school day was finished, much to Jenny and Sarah's relief, and it was time for lunch. On the way to the dining hall, a question surfaced in Sarah's mind. "I wonder whether there will be anything out of the ordinary about lunch?" she asked her companion, "After all, look at the classes. I have a hunch about lunch; someth...