Private Lessons II - Teaching Mommy
Copyright© 2022 by Master Jonathan
Chapter 1
Romantic Sex Story: Chapter 1 - A continuation of the story "Private Lessons" this one brings her mother into the game!
Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa Reluctant Heterosexual Fiction School Workplace Exhibitionism Masturbation Oral Sex Voyeurism Teacher/Student
The second semester parent/teacher conferences were held all week and as usual, I was there during the conferences in case any of the parents wished to speak to me about the school or their children. Allison Walker, my beautiful blonde student-slut had her conferences scheduled for that Friday.
School at Bancroft Academy where I am principal lets out at 3:30 in the afternoon but on Friday after school, Allison knows she has an appointment with me for some private “lessons”. She had been meeting me like this since early in the school year, when she was caught cutting class with two other girls by the security guard at Ravenwood Mall. The guard had called the school and our security went to pick up the three truants.
After meeting with each one individually, it was revealed that Allison, despite her protests to the contrary, was the ringleader of the band and so in an effort to keep her in school and also relieve some of my own sexual tension, I blackmailed her into becoming my personal cumslut and we had been meeting both after school and on the weekends sometimes for some private “lessons”.
But soon after we began, I had realized that Allison, who at first resented the idea of becoming my slut, now craved it and we both looked forward to Friday afternoons together and every Saturday we could spend time together.
She had learned a great deal on how to please and pleasure me – she was a quick study and really gave it her all once she got on board with the idea. And she had also learned that in return she received a lot of pleasure as well.
As I had instructed her, she had gotten rid of all the other boys that were chasing after her and now I was her only source of cock, which I was more than happy to dole out whenever she needed it. I just didn’t want any surprises – STD’s or otherwise!
She had become such a slut since that first meeting in my office, that now she was always ready for a good hard fucking. She wasn’t the type who wanted to be made love to; she wanted to be fucked ... hard, deep, and repeatedly.
She was the perfect fuck; drop dead gorgeous, a great cocksucker who loved to swallow and deepthroat (now that she had been properly trained of course), had a tight hot cunt although it had seen some use, and her perfect ass could now take all eight inches of my big cock.
Once I broke through her snooty, diva personality, I discovered she was quite the submissive deep down and she had the filthiest mouth of any chick I had ever fucked. She was the perfect fuck. Knowing she was graduating in under a month was disappointing, as she had really brightened up my Friday nights.
This particular Friday night, however, would prove especially momentous. The school day was over and the school was virtually empty. The students couldn’t wait to get their weekends started and after a week of parent/teacher conferences the teachers were tired of looking at these walls as well. A few teachers – those with conferences – would be back in a couple hours, but the rest just wanted to put this hectic week behind them.
Allison was in my office as usual, laying across the width on my desk, with her head hanging off the edge on one side. I was facing the upside down blonde with all eight inches of my cock shoved down her throat. Allison was practicing her deepthroating skills and doing pretty good at it.
While she made those delightful sexy gluk-gluk-gluk sounds as she boobed on my cock, I was busy toying with her young full tits and tweaking and tugging on her nipples. Allison had confided to me that all of the boys that she had dated and let fuck her in the past were always treating her like a china doll, afraid of being too rough and hurting her. So their lovemaking was soft and gentle and caring. Which she said has it’s place, but she liked to fuck.
She wanted to be treated like a slut; like a whore. She wanted to be fucked hard and deep. She liked to talk dirty and be talked dirty to. And that’s exactly what I gave her every time we were together. Now she couldn’t get enough of it and it had made her a very dirty little slut!
“Fuck me, Sir, I need to feel your cock in my cunt,” she begged, popping me out of her mouth for a moment. Since all three of this blonde sluts’ holes are equally amazing, it made no difference to me which one I was plugged into, so long as I was in one of them.
I moved around the desk to the other side and between her widely splayed legs. I had a perfect look at her lovely blonde cunt. Allison had been fingering herself while she gobbled my cock so her whole pussy was wet with her juices. Her fat swollen lips glistened in the room light and she looked so beautiful.
She raised her head and looked up at me, her hunger for my cock obvious as she moaned, “Please come and fuck my slutty cunt, Mr. Stewart. I need to get home soon and get ready for my parent/teacher conference. Mom said she wants to come and see who is responsible for my good grades!” Her hands had moved between her thighs, holding her pussy open as if holding the door for me.
I questioned, “Is talking with your teacher more important than being my dirty cumslut?”
She quickly apologized, her tone seeming sincere. “Oh no, sir! Nothing is more important than pleasing you! It’s just that Mom wants...” she started to say.
“I was just kidding,” I smiled, “yes your Mom should meet your teachers.”
“Well I want her to meet you too, after all she wants to meet the person responsible for me getting good grades again!” she smiled. “And I want her to meet you with your cum in my cunt!” she added with a devilish grin, her nastiness never getting old.
“Well let’s make that wish come true then,” I offered, moving forward to fill her hungry pussy in the most satisfying way possible.
My cock easily filled her young cunt and she let out a joyous scream as all eight inches filled her. “Yesss! Ohhh fuck,” she screamed, “that feels so good!”
Once deep in her, I began pounding her cunt, my body slamming into her forcefully with each hard, deep thrust forward. Her breathing increased as I literally fucked her like I wanted to break her. “Fuck, your pussy feels so good!” I grunted, knowing I was not going to last long at this pace.
Her hand frantically rubbed her clit and as she orgasmed from my cock and her hand, her pussy tightened around my cock, literally trying to milk me of my cum. The intensity and excitement was too much – I had been looking forward to our rendezvous for days now.
As she exploded and filled her pussy with her juice, I blasted my cum into her pussy to add my part, our two fluids mixing together into some kind of sex cocktail which filled her to overflowing and leaked out around my still pistoning cock.
She lay on my desk moaning and trembling, occasionally spasming as the last of her orgasm left her body. I collapsed on my chair, my own legs too wobbly to be trusted. Once we both recovered, she weakly got up, her make-up a mess. She looked in her compact mirror and joked, “I look exactly how I feel.”
“Until next week,” I said, getting dressed.
“I’ll be here,” she promised giddily, before leaving to head home and get ready for her meeting with her teacher. As she got to the door, she turned back “Are you going to be here to meet my Mom, Mr. Stewart?”
“Yes I’ll be here. I’m looking forward to meeting her,” I said. She smiled and turned to leave.
I cleaned up my office and the mess we had made and then went home to shower and change clothes before having to be back at school in a couple of hours.
I got back to school and was in my office in case any of the parents wanted to talk with me. I was also there because as a private school, I had to be present whenever the school was open just in case something was to happen and I was needed. A couple parents stopped by because their kids wanted me to meet their folks but it was just a social call.
I was eagerly awaiting Allison and her Mom ... I wanted to see the spring from which such a beauty would come forth. Plus, if genetics had anything to say about it, Mom just may be as much of a slut as her daughter – after all, she had to learn that somewhere!
It was about 8:30 or so when I saw Allison and her mother come into the front office. My office – the Principal’s Office – is in the back, but with my door open, I have a good view of whoever comes in the reception area. I came into the reception area and Allison came forward with her mother.
My cock stiffened almost immediately upon seeing Allison’s mother – she was an older, but still just as beautiful, version of Allison.
“Mr. Stewart, this is my mom, Barbara Walker. Mom, this is my principal, Mr. Stewart,” Allison said, introducing us.
I extended my hand, remembering that Allison had told me she was a divorcee. My brain already started to think of how I could get her out of her panties and my cock into her pussy.
“It is nice to meet you Mrs. Allen,” I said, trying to cover my thoughts.
“It is Barbara, Mr. Stewart,” she politely replied, her soft sensuous voice only feeding my fantasy of fucking her.
“Well, if we are on a first name basis, then I insist you call me Tim,” I smiled back, already working up a blackmailing scheme.
“Okay then, Tim. My Allison tells me you are the one responsible for completely changing her outlook on school,” she said. Barbara smiled sweetly – evidently she was used to her charm winning over any man who came up against her.
“Well, Allison and I have worked things out,” I said, glancing at Allison who had a devious smile on her face.
“No, I am serious. Allison was quite a handful there for awhile, and I was very worried she wouldn’t graduate. I’m sure she has told you that I am divorced and that her father lives in San Francisco with his new wife. She hasn’t had a father figure around to help and frankly, it’s been hard raising her on my own.
But since you started keeping her after school on Fridays and helping her, she has been a totally different person. I don’t know what you have been doing for her, but I can’t thank you enough,” the naive mother gushed, unaware she was really thanking me for fucking her daughter!
“Oh trust me, the pleasure was all mine. Once I got past her diva resistance, she was an eager learner,” I said, winking at Allison.
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