Finishing School Ch. 01

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Tiffany Goes To School.
3.4k words
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Part 2 of the 5 part series

Updated 06/15/2023
Created 12/31/2022
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"You understand, Mr. Fredericks," I said, sitting at my big, impressive desk, my best serious look on my face, "that the $60,000 tuition is just the base rate. There will be additional charges billed to your credit card and I won't be calling for approval."

He chuckled and said, "David, I grew up middle class, went broke, now I have plenty of money, and at no point did I worry about nickles and dimes. I've signed and I won't be bitching about charges at this point."

"Okay," I said, "the lawyer says I need to remind you for the record and on tape."

I turned to his trophy wife, and what a piece of work she was. I figured she was still getting asked for her ID if she went into a bar. She was blonde although to my trained eye it was clear that when I had her naked her natural hair color would be something else. She was over-made up, that blonde hair piled high, and over-accessorized (if it's not a word it should be) with a half dozen rings and studs in her ears, a Goddam nose ring, what I always called a snot hook, rings on each finger and a half dozen gold chains around her neck, showing nicely on the expanse of well-enhanced cleavage she was displaying behind the expensive silk blouse unbuttoned three buttons down.

And just to complete the image of a trophy wife brat, she was chewing fucking GUM!

Oh, sweet cheeks, I'm going to handle your orientation myself, I thought.

"And you, Tiffany," I said, wondering if that was actually what was on her birth certificate, "do you understand what the Finishing School is about?"

She was leaning back in her chair, exuding insolence.

"Anything for my baby," she said, flashing Fredericks an adoring look so fake I expected a movie director to materialize and yell "CUT!"

"Where do I sign?" she asked, deigning to lean forward.

I pushed the contract across the desk, the little stick-on "Sign Here" tags showing the half dozen places she needed to sign. She sighed, theatrically, and scrawled something unreadable. That was okay, though. I had a video recorder going and Mrs. O'Neil as a witness.

"All right, then," I said standing and walking around the desk.

"Kiss your bride goodbye," I said, offering my hand and shaking as Fredericks stood, "she'll be a new woman the next time you see her."

Tiffany stood too and kissed him and it was obvious how she had bagged her sugar daddy. The kiss absolutely oozed promise and pleasure. She was molded to him, one hand around his neck, one entwined in his hair. One foot raised in a scene I knew she had watched in a movie somewhere. Her hips rocked in minuscule motions, almost too tiny to see, but I'm certain Fredericks was feeling them.

Hell, my dick got hard watching that scene and I was pretty jaded when it came to women being sexy.

Finally, he broke the kiss and caught my eye. In that instant I understood. He knew exactly what he had, and enjoyed it, but wasn't about to be taken in by it.

I grinned back.

He patted her cheek, turned, and left without looking back.

When he was gone her act turned off.

It was like a switch turned off her adoring trophy wife persona the instant the door closed behind him.

"All right, let's get this bullshit over," she said, all haughty Lady of the Manor, another scene I was sure she had watched on the big screen somewhere.

Well, I had seen this act before too.

I reached out, quick as I had been taught in those hundreds of hours in a karate dojo, and grabbed her by the hair, twisting, the sudden pain and shock immobilizing her. Mrs. O'Neil moved in, expertly, this wasn't our first rodeo, stuck the needle into her neck and drove the plunger home.

I held her while the bolus of Ketamine did its job and she quit fighting. She wasn't exactly unconscious, but she was very much open to suggestion.

We walked her down to the little surgery room.

When Mrs. O'Neil told her to undress she did so without hesitation. Then we got her situated in the special gynecological chair we had developed. We laid the chair back until she was prone. I enjoyed watching Mrs. O'Neil work as she tightened the strap that ran around the headrest to hold her in place by looping around her neck, not tightly enough to choke but enough to prevent any movement. A second strap across her forehead, this one much tighter, held her head absolutely immobile.

Similar straps at wrists and elbows locked her arms to the armrests and a wide belt across her hips fastened her to the chair. She worked one of the little foot pumps at the base of the chair and Tiffany's hips rocked forward, pushed up by the cushion. Two more straps, one at her ankles and one at her shin just below her knee, clamped her firmly to the stirrups, and as I watched Mrs. O'Neil moved first the right and then the left stirrup to its maximum point, leaving the lovely Tiffany completely exposed.

I wasn't surprised that she was smooth as a grape. So smooth, in fact, that I assumed it was permanent, something involving lasers and chemicals I figured.

Mrs. O'Neil finished the preparations with strong surgical tape. She used a special wet wipe to clean Tiffany's clitoral hood and then parted the very top of her vaginal slit, stuck the end of the tape on the bare skin she had cleaned, and then pulled the tape up, pulling the clitoral hood out of the way before sticking the rest of the tape to the skin of her belly, holding the hood back. She did the same thing to both of Tiffany's full, plump, outer lips, her labia majora, taping them to her thighs.

She carefully cleaned the skin around Tiffany's clitoris, a very distinct, VERY pink little button, plainly on display in this position.

"Now, the tricky part," she said, tearing open the little package that held the device that was the key to the Finishing School's success. About the size of a hearing aid battery with a very thin wire about a half-inch long exposed.

The wire was like one of those acupuncture needles, so fine it was barely felt as it probed. And she was probing now. It's important that the Training Aid be located precisely in that ganglia of nerves that offer a woman her pleasure.

Suddenly Tiffany screamed and you could see her body straining against the straps that bound her to the chair.

"There you are, you little rascal," Mrs. O'Neil said in a satisfied tone as she carefully marked the spot while Tiffany's screams echoed around the room.

Her screams stopped suddenly as Mrs. O'Neil turned the training aid off.

"Now, let's get you fixed, dear," she said in a voice that would have calmed a frightened fawn.

This part always fascinated me, so I watched as she filled the syringe with Novocaine and administered a half dozen shots around Tiffany's clitoris.

She made a small incision with a scalpel, very little blood, and carefully placed the little device where she had marked. Then she used a dozen tiny stitches to suture the little wound, clipped the threads, carefully cleaned the area, and then covered the wound with a flesh-colored material, essentially super glue, before stepping back with a satisfied smile on her face and saying, "Done!"

Tiffany was still very much under the influence of the drug and offered no resistance as we unstrapped her from the chair, dropped a fresh white shift over her head, and led her to her quarters.

"Take this, dear," she said, offering two Ramelteon tablets and a glass of water.

She took them.

"Now lay down, honey," Mrs. O'Neil said, "and get some sleep." She turned on the speaker built into the wall and restful, quiet music filled the room.

I watched, always fascinated, as the drugs took effect and Tiffany went to sleep.

"And now, me?" Mrs. O'Neil asked, a speculative look in her eye.

I grinned. "You know me too well," I said.

She smiled. "Oh," she said, "you men are so predictable."

"Come along, then," she said, taking my hand.

In her room she turned, faced me, and slowly, holding my eyes with hers as she did it, lifted the fine chain that was around her neck over her head and handed it to me. I smiled and caressed the fob suspended from the chain.

"Sadist," she said, the desire clear on her face, the womanscent of her excitement in the air.

"Masochist," I said, grinning, and pushed the button.

Her body went rigid and she was breathing in sharp little pants as she accepted the agony I was giving her.

Her will broke. I was always amazed at how much she could take. Our girls fell to the ground, screaming at the first touch of the Training Aid. But Mrs. O'Neil stood it for almost a minute before falling to the ground and crawling to me.

"No more, please, sir, god, please, no more," she said, wrapping her arms around my knees and kissing the material of my pants at my knees.

I made her beg and grovel for another half minute or so before releasing her.

She collapsed, sobbing, curled into the fetal position, hugging herself where she hurt.

I watched for another minute or so and then pushed the other button.

The orgasm might be artificial, but it is no less real. She was screaming again, but this time she was screaming, "YESSSSSS, GOD YESSSSSSSSSSSSSSSSSSSSSSSSSSS."

When I released her this time she was gasping for air, great whooping breaths like a swimmer breaking water after too long underwater.

I moved to sit on the edge of the bed and watch while she got herself back under control.

Finally, she stood.

"Take off your clothes," I said, "entertain me."

She smiled and put on a record, yes, an actual vinyl record, and as the soft music, what she called "torch songs," started up, started her strip tease.

I loved watching her. It was such an interesting contrast. Her face and her hair and her body were all the 50-something matron she was. But in her head, she was still the high school cheerleader who had gone steady with the running back and got knocked up at 17.

Now, at 50-something, her body showed the child she had born, and the years in between.

She parted her legs, a bit more than shoulder length, and stood still for a moment or two, picking up the beat. Her hips started moving, snapping side to side. She did that thing only a woman seems to be able to pull off, running the fingers of her right hand through the left side of her hair and then doing the opposite, her left hand through the right side of her hair as her body picked up the rhythm.

She made each button of her jacket a little two-act play, first working the button through the buttonhole and then popping the button free. When she shrugged out of her jacket and tossed it, artfully I thought, to lay in the chair in the corner of the room, that matron's body was on display. Her bra showed through the not-quite-opaque material of her blouse and she started doing the button thing again on her blouse.

The blouse joined the jacket and before the next song was over, the skirt joined them.

Part of the reason she's so damn good at her job is that she lives the part she teaches. Her bra was so white it almost glowed. Her girdle was the same way. Her nylons had seams that were ruler straight, hooked to the girdle in the old-fashioned way. The 3-inch heels on her pumps did good things for her legs and her walk as she strutted as part of the dance.

The bra came off next, a heavy-duty thing to handle heavy breasts. Her breasts sagged dramatically, very dark nipples and areolas still pointing straight at me. A faint tracery of blue veins and stretch marks added to their allure.

She had to break the rhythm of her dance to get out of her shoes, undo the stockings and roll them down her legs, and then push and squirm out of that girdle.

Finally, only her panties were left, very white, very traditional, what we call granny panties.

She closed the distance between us and said, "you can do some of the work."

I grinned and rolled the panties down, smiling at her as I got them past her knees and let them fall to the floor.

She had a classic "mombod." Her waist was a distant memory, and her pot belly gave her a bit of a belly apron with the girdle off.

It was her pubic hair that was the center of my attention, though. Very thick, very dark, very curly, it made a thick mat from the bottom of that little roll of her belly and spread a bit down her thighs and to that hollow of her hip bones.

Her excitement was obvious in the womanscent that she gave off and the thick nectar, almost like Vaseline, making the hair at the bottom of that mat of hair wet and shiny.

"Will you touch me?" she asked, her eyes holding mine, her face very serious.

"Ask nicely," I said.

She smiled and leaned forward, breathing the words into my ear, her voice very soft, "please, sir, touch me."

I reached forward and very slowly, very deliberately, reached between her legs, almost touching her anus, and then dragging my finger forward, slowly, parting that thick hair and her meaty labia along the way, until I brushed against her clitoris as I finished what I was doing.

My finger was thick with her nectar when I lifted my hand clear, looked at it, and then touched her lips with it. She opened her mouth and took my finger in, sucking gently, her tongue massaging where I was slick with her honey.

"Such a naughty girl," I said.

She pulled back slowly, sucking my finger as she went until it came loose with an audible little pop.

"I am what you made me," she said, and then leaned forward and kissed me lightly on the lips, "for which I thank you."

"Will you make love to me?" she asked in that same soft voice.

"Ask nicely," I said, grinning now.

Her smile was almost angelic right then.

"Please, sir," she said, her eyes almost too close for me to focus on them, "show me you love me, show me I'm beautiful and desirable."

I stood and said, "up on the bed, girl."

She giggled at that. "I love when you call me girl," she said.

I undressed, not making it a strip tease as she had done, but taking my time. Okay, I liked that her eyes never left mine.

As I finished, pushing down my boxers and stepping out of them, I was hard.

Oh, don't get me wrong, pretty much anything with tits and a pussy will get me hard, but I do have a soft spot in my heart for the first graduate of our school.

And she IS good in bed.

So I crawled up onto the bed, keeping my knees outside of hers, moving forward until my face was directly over hers.

I kissed her, very gently, lips barely brushing, before caressing her cheek with my lips until I could say softly into her ear, "does a beautiful woman like you know the effect she has on men?"

Yeah, okay, it's a line, but it usually works to some degree or other.

She giggled at that. "Such a bullshitter," she said.

"All true," I said and this time the kiss was firm, more than a light brushing of lips.

I scooted around, working my knees between hers, and said, "relax now, let me feel the natural you."

She sighed. "Baby," she said, her voice plaintive.

"Relax," I said, letting a little snap into my voice.

"Yes, baby," she said and I could feel the residual tension leave her body.

As I slipped inside she was so loose there was no friction at all. I liked her like this. She had told me once that her son hadn't been a particularly big baby but he had, as she put it, "really stretched her out," and this was very true. She thought it made her unattractive but I liked her like this.

"What a good girl," I said and she giggled.

"Please?" she asked in a high-pitched, whiny voice.

"No," I said, and she sort of whimpered.

My rhythm was speeding up now but without any friction, I was still not getting any of that slow building of pressure deep in my belly.

But it was working for her, and that's what I wanted. Her breath was starting to catch and I could feel the way her love honey, her natural lubricant, was changing. It was becoming thinner and hotter and even slicker. Her womanscent was strong now, and I was inhaling it, the best aphrodisiac in the world.

Her fingers were digging into my back and her hips were bucking, her breath was wheezing, almost whistling, as her excitement had her sinuses swelling.

And she was pleading for what she needed.

"Please, my love, please baby, please honey, God, please," she was whispering in that wheezy breath.

"Relax," I said, my hips thrusting hard now, each lunge into her making our pubic arches meet almost violently. There was an audible slapping sound of flesh on flesh and a little splash from the way she was flowing.

Her heels were making a little drumming on my ass as she pulled me deeper with each thrust.

Throughout our lovemaking I had been talking to her, telling her how beautiful she was, and how much I loved her. And I had been covering her face with kisses, reinforcing her sexuality and desirability.

Finally, I said, "squeeze."

Her eyes got big, her mouth opened, and her face turned red as I felt her bear down with those muscles all of our girls are trained to use.

I felt her squeeze on my erection and then her sudden release soaking my balls and my thighs. Her mouth was wide open in her silent scream of ecstasy as her hips thrust, soaking me more with each thrust.

"Tighter," I whispered into her ear and felt her bearing down, so tight she was almost painful around me.

She was grunting now, really working those educated muscles.

"Please, baby," she was saying now, her words changed now, "fill me up, give me what I need, give me your gift, please baby."

I kissed her, said, "I love you," and let my control go.

As I came she screamed her pleasure and her love.

And the thing is, she meant it.

Our procedures at the Finishing School are VERY effective.

As her breathing slowly returned to normal, okay, as OUR breathing slowly returned to normal I just looked at her, enjoying what I was seeing.

She looked like exactly what she was, a 54-year-old widow, into her second half-century, who knew how to make the best of what she had. Right now she looked like a 54-year-old woman fresh off of a good fuckin'. Her makeup was gone. The sweat and tears left mascara streaks down her cheeks. Her hair was a mess. There was a little wet line from the corner of her mouth where she had drooled a little.

She looked, in other words, like a Finishing School graduate should look after she pleases her man.

"Get some sleep," I said, kissing her gently, "I have a feeling we're going to be working hard tomorrow. It looks like Tiffany is going to be a handful."

She smiled, kissed me, and said, "Nothing I can't handle, my love."

I smiled back, kissed her again, brushed my hand across the soft thickness where her waist had once been, and said, "night night, I love you."

"And I love you," she said, her arm laying across mine in a light embrace.

We slept a tired sleep that night.

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