Dear Shoeblossom,
Enclosed is a journal I kept after hiring a dominant couple to supervise me for a period of time. I actually first read about Sergei and Kyrsten from "Letter from Maui" and was determined to meet them and hopefully hire them.
And it was financially quite steep! And, Sergei and Kyrsten were fun and lively, but they were a tough pair. (I can't believe I had to wear a butt plug for five months.)
And they were worth it, and quite well known in the community.
I was on waiting list for nearly two years to "rent" this expensive couple, but they certainly kept their promise to make me a true submissive chastity slave, to make me obedient and get me to the point that when they left I would be able...
To STAY crotch-locked except for when they returned to give me an occasional release session.
So basically it would be six months of intensive training from this couple, and then very occasional visits where I'd be released from celibacy for a weekend of torture and teasing and then, based on my obedience, a supervised masturbation or an orgasm-less milking (if I was bad.)
Why would I put up with this? And Pay for it?
I know I've got something weird going on. My first wife, Pomfret, cheated on me and ridiculed me for eight years, and still comes by for her alimony check with whatever stud she's boinking...he generally kicks me in the nuts, and she walks off with the money!
My second wife, whose name I sill cannot say, once threw me out of the house stark naked after I caught her sleeping with my best friend...
So I'm a sick puppy!
Basically, I've given up all hope of a normal sex life with what I went through, and you and your readers can enjoy the journal-
March 8-Tonight Kyrsten moved in. She's quite something. Late twenties, with teased honey blonde hair and a pixie-ish grin...freckles dusting her pug nose. Very hot.
She has 36 C tits packed in a hot pink sweater and yes, long legs in seamed stockings. Oh wow, the high heel type.
I helped Kyrsten put her things away in the master bedroom, watching her cute little ass as she bent over to unpack. I've always lusted after girls like her, the "smoking section" girls who hung out with the greasers and leather jackets.
I sure hope she likes the master bedroom. I discovered to my disappointment that she won't let me sleep there even now, when Sergei hasn't shown up yet.
"Serg is finishing up with our last sub, a Mrs. Creighton, who is using her divorce money to introduce a little BDSM in her life. I sure enjoyed whipping that fat, saggy 60 year old ass." laughed Kyrsten.
After we'd settled her in, and I'd made her dinner, Kyrsten led me into the parlor and sat down on the couch. I was kind of standing in front of her, wringing my hands, and probably looked ridiculous in my sweater vest and plaid pants.
"Why don't you take all that crap off, Normie, let me see what I'm working with here."
"Well-uh-we don't-"
"I don't have time for a lot of bullshit from you, hon. I can rip your clothes off myself, but it won't be as much fun as you think."
I was a little embarrassed, since she wasn't undressing at all (though her nipples were hardening under the snug pink top.)
I slowly pulled off the sweater and unbuttoned my shirt, and stepped out of my pants, Kyrsten laughing at my Argyle socks. When I was naked, I stood awkwardly in front of her, and my cock began getting hard. I tried to cover it with one hand, but Kyrsten shook her head.
"Hands always in the way. I bet you started covering your penis when you were in the gym, so bigger guys wouldn't make fun of you. But I bet they did anyway, and probably whipped your ass with their wet towels."
I flushed. How did she know?
Kyrsten pulled handcuffs, real police ones, out of her purse and instructed me to turn around, and then she locked them behind my back.
And then I spun back around and I was standing nude in front of this beautiful clothed girl, and my hands were indeed out of the way, and the humiliation was killing me, but getting me really hot, too.
My dick got kind of thick!
Kyrsten reached out casually and glided her glittery purple nails up and down my penis, and I tried hard to stand still.
"I bet you pound that pud all the time, don't you? You probably shot it all over my picture on your computer screen. That's so sad."
Kyrsten tickled my scrotum and smiled.
"This is why you're going to have to go into chastity. God, while I rub your dick, your thighs tremble, Normie. You don't get laid much, do you?"
"N-no. Miss Kyrsten, not much."
Part of the problem of course is I'm not very hip. Mother forbade me to listen to rock music, preferring to have me hear Gregorian chants. Once, when I was getting my M.B.A., Mother caught me humming a Beatles tune, and made me sit in the driveway of our house, wearing adult diapers...
"Now I'm going to wake you up a little. These are Victor rat-traps. Don't wince, you told me you saw a dominatrix who put clothespins on your nipples, so the metal of the traps can't be that hard on your chest...
Oh, stop weeping. That doesn't hurt that much, does it? See? I 'm playing with your dick, babe. That distracts you from the pain, doesn't it?...
Fine! Bitch and moan then, I'll just knock the rat-traps off your nipples, and...you're howling louder!"
But, after a few moments of her stroking, I forgot the intense pain on my nipples.
"We'll put the traps on for half an hour every day, and eventually you'll get used to the pain."
Kyrsten really knew how to give a hand job. Her nails were long and sharp and her fingertips were soft, in a contrasting way.
Kyrsten's forefinger tickled my bulging glans and she rubbed it a bit more, and I began producing pre-ejaculate, which she massaged into my penis.
Then, suddenly, Kyrsten pulled her fingers away as I was about to spurt. But it was only so she could pull her sweater off!
And there were her breasts, perky, marvelous, the nipples barely covered in a little jogging bra, and what a cleavage, wow.
And she kept rubbing, bending over slightly so I could look down the adorable divide between her boobs.
"You'd love it if I let you put your dick in between my pink round tits, wouldn't you Normie?"
I nodded shakily.
"What you really need is a big dick in your mouth. You can't suck cock, can you?"
I blushed and shook my head.
"You understand you're not a real man, don't you? You're paying me ten grand a week out of your Roth IRA to tease and humiliate you, and to have you watch me fuck my boyfriend, before you suck his dick...
Because you don't deserve a girlfriend. You understand that, right?"
I began weeping softly.
Kyrsten went into her purse again and pulled out a foot long, thick black dildo.
"Open your mouth, honey."
I gasped, and in the big rubber thing went.
My mouth was incredibly stretched now. How uncomfortable.
Kyrsten giggled. She grabbed the end of the dildo with her delicate fingers and rammed it in and out of my mouth until I spat it out, coughing, and she lay back on the couch and laughed hysterically.
"You are such a little wimp. I bet girls have taken advantage of you forever, right?"
"That's right, Miss Kyrsten."
I hung my head as I stood in front of her with my hands manacled. I thought of the girls who I'd tutored in college. English Lit, trigonometry, physics...I was an expert in all those subjects, and the coeds kept approaching me.
But although they gave me deep hugs for my efforts, as I tutored them for free, that's as far as it went.
One girl, Shelly Caldwell, had promised me a big surprise if I got her the test answers to a big French test, and as I was a teaching assistant, I risked my scholarship to do this.
Shelly had told me to go into her bedroom and strip and she'd give me a reward, as she'd gotten an A on the test and in the class, as I'd also written all her papers.
"Put on that garter belt and the stockings, Normie, it turns me on, we'll have a real party in there." Shelly had whispered.
But then, instead of Shelly, five guys from the football team had run in, along with a photographer, and the guys had beaten the shit out of me and thrown me out on the lawn, where Shelly and her friends (all of whom I'd tutored) had laughed uproariously at me...
They'd even taken my glasses away (I can only see shadows without them) and watched as I staggered and fell into mud puddles...
And Mother had given me a hard spanking when I'd gotten home (as someone had e-mailed her the photos.)
But after being the laughingstock on campus, I realized that whenever I had thought of my humiliation, I would be overcome by a desire to masturbate. Whenever campus jocks snickered as I slumped by on campus, I would fantasize that they were forcing me to service them...
And I told Kyrsten of all this, my voice shaking as she continued to rub and prod my hardening penis, and of course she laughed, cruel peals of unsympathetic giggles, as she continued to rub and tickle my frustrated penis.
"That's a scream of course you thought that Shelly would probably let you fuck her but no one gets fucked when they're a sad little four eyed geeky weirdo do they, Normie?"
"And I bet you continued to tutor her the next semester, and still charged her nothing right?"
I nodded sadly.
Kyrsten laughed harder. She took a delicate forefinger and flicked my glans hard with the nail and the pain combined with the humiliation arousal was too much. I shot my spunk all over the tops of her plump breasts.
Kyrsten looked down at her smeared rack and stared back up at me in mock outrage as she sat there on the couch, legs crossed in the tight mini.
