tagBDSMLetter from Frost Haven

Letter from Frost Haven

byjustincbenedict©

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.

"How could you have an accident like this, and make a gross mess?" Kyrsten grabbed me by the scalp and pulled my head to her cleavage, and instinctively, I began licking the semen off her bosom.

How disgusting.

"You have to learn self control, Normie, otherwise this will never work. I'm afraid I will have to punish you now."

Kyrsten pushed me back and, not having my hands to balance me, I fell on my ass, the pressure pushed against my cuffed wrists.

"P-punish me?"

"You shot your wad all over my tits. Who the fuck do you think you are?"

Kyrsten slapped me hard across the face, her punk-rock finger rings scratching my face.

As my face stung, she went on breezily.

"Sure, I let Sergei shoot on my tits after I've sucked his dick a little, but remember Serg is a real man. You're a catamite, a freak. I still remember your pathetic e-mails about how your mother made you go to music lessons while the other boys were playing ball, ugh...and ballet dancing too?"

Then Kyrsten let me into the dining room and lay me across the table. She darted back into the parlor and pulled my belt out of my discarded pants.

When she returned to the dining room, Kyrsten gave me the whipping of a lifetime, it probably hurt even more because I had just had an orgasm and wasn't horny. It really was like pure punishment.

My paws were still locked, so I couldn't cover my butt, and I was soon sobbing loudly from the viciousness of the belt.

But my cock began getting hard again. Kyrsten had given me a "safe" word in the early e-mails, but a stubborn part of me refused to use it, and finally she stopped whipping me...

And just listened to me crying lustily, and taunted me.

"I can see we are going to have to do some serious work with you, my little faggot."

Kyrsten now had me on my knees in the living room.

"I expect you to be able to hold back your orgasms when I tease you, and also to take your punishment like a real man, with no crying."

Finally, Kyrsten removed my handcuffs and informed me she was excited by all she'd put me through and asked if I had any oral skills.

As my tongue was the only thing that kept my girlfriends even briefly interested, the penis being tiny...

I nodded assent and we went to bed where I serviced Kyrsten for nearly three hours.

Kyrsten wouldn't let me touch her breasts or even see them, as she kept the jogging bra on.

Still, it was quite arousing to lick her shaved snatch to many orgasms, and then she let me kiss and rim her bubble butt and give her a long massage.

March 9-Today I took the day off from work and Kyrsten took me to meet her friend Saskia, who is a piercing and tattoo expert.

Saskia pierced my cockhead and my testicles, and locked my penis into what is called a "Prince Albert."

"Saskia says that we should give the piercings time to heal, but I want you to buck up and get locked up now. It may be a little painful for a few days, but you'll get used to it."

Kyrsten chugged a Budweiser with Saskia before adding...

"Now I can tease your dick without you having accidents, Normie, the piercings being looped together."

I was just mortified, standing there naked and bleeding slightly from my dick in front of the two clothed women...but I had to learn to deal, right?

Kyrsten played with my dick all the way home while I tried to concentrate on my steering. Then she dressed in a little violet teddy and stripped me down and stroked my manacled dick until it was screaming for release.

Oh, her tits looked so good in that little negligee! I ended up servicing her orally for quite some time! I was so frustrated.

March 15-Wow, it's been seven days since Kyrsten got here. Sergei still hasn't arrived which is nice in my opinion.

I like having Kyrs all to myself. We go on bike rides and to movies together, and have gotten together with some of my friends. They all think she's my girlfriend, and I've never kept company with someone quite as beautiful as she is.

At home, Kyrsten keeps me pretty busy. Sometimes she ties me spread eagled to Mother's old Princess bed, which of course is in the master bedroom.

Then Kyrs necks with me and tickles my armpits and toys with my cock for hours. Sometimes she unlocks me and lets me jerk off into a hankie and suck the semen out of it, if she is especially pleased with me.

But now I've not cum in 2 days and I think Kyrsten's plan is to work me into longer periods of chastity.

Kyrsten put a hook in the basement ceiling and has begun hanging me there for short periods of time while she whips my naked ass. It's scary and painful, but then she tickles me a bit, and that's fun.

March 19-Kyrsten had me dress in full makeup and a slutty dress and heels, total drag last night. She had me walk up and down Ellis Avenue, which is the Frost Haven red-light district.

I had a few guys approach, but then they realized I was a tranny and threw discarded beer cans and rocks at me.

I continued to strut and Kyrs followed in my Beemer, the headlights shining off my twitching Pleather covered ass in the disgusting Spandex suit. and those size 16 heels!

Finally, Kyrsten led a drunkard over to me and made me kneel in the alley and suck on his smelly penis.

I didn't literally give the guy a full blowjob, but he peed in my mouth (ugh) and then jerked off onto my face.

But when I got home, I was so horny to cum. The humiliation and degradation really turned me on. I rubbed my dick but couldn't get an orgasm because of course, I was pierced.

March 22-Today it's been 10 days since I got to orgasm. It's making me crazy.

March 25-I am crushed. Today Kyrsten told me that if I could take my cock being whipped with a radio antenna I have for three minutes, she'd let me suck her breasts, or at least kiss them...

So I took down my pants, and she undid the piercing and lay my penis across the dining room table and gave me ten harsh ones, and whenever I jumped, or tried to touch my penis, she reminded me of the prize, those tits in a cute little Seventies tube top.

But at the end, when my penis felt shredded, Kyrsten laughed and said she'd been kidding, and I'd never get to touch them. What a betrayal...but it was hot, too.

March 26-Kyrsten made me put on lip gloss and service a big thick dildo...during my lunch hour, and Monique watched and was laughing her ass off.

March 28-Wow. Kyrsten dresses like a bar slut constantly, tight jeans, short skirts, cut-off shorts, it's really something.

In addition to the constant tease, Kyrsten is quite the disciplinarian. Caned me five times, paddled me twice, and has hit me again and again with the belt she used on me the first day.

Kyrsten also cut a switch from the spruce tree in the park and whipped my cock once, even pierced as it was, to take my mind off my celibate situation.

Kyrs did let me jerk off night before last, but it was only after she came back from partying. I had come in from work and made her dinner, and then Kyrs had stripped me naked and locked me in the closet while she went bar-hopping.

She brought a couple of cute, drunk girls home and brought me out and ordered me to jerk off in front of them.

The girls didn't even get undressed-Kyrs told me if I complained, she'd bring home a guy the next time and have me service him. I still am a little traumatized from my time in drag.

April 2-Kyrsten came to work with me today. I introduced her to my secretary, Monique, and Tasha, the office manager.

Monique and Tasha are both cool, contemptuous types. I had made the mistake of telling Kyrsten that I have jerked off to fantasies of Monique punishing me.

Kyrsten told these fantasies to Monique as I stood there, flushed.

"And, sexual harassment aside, I'll have Normie give you a five percent raise if you whip him with this paddle."

As Tasha walked out of the office in disgust, Monique took the paddle in her hand, fingering it with her red nails.

"Why does it have holes in it, Kyrsten?" Monique asked.

Kyrsten laughed. "It's a Spencer paddle. the holes cut wind resistance so you can hit him faster and harder."

Monique laughed and told me to take my pants down. Monique apparently has quite the tennis arm. I run a call center for telemarketers of ad space, and employ mostly women, usually pretty ones...

My fault for being the hiring manager. Anyway, the girls all came and looked into the boss' private office after they heard me screaming and carrying on, having my ass massacred by the cruel and determined Monique.

Finally I knelt in front of the crowd of giggling women, my pants around my ankles and my penis sticking out of my shirt sleeves. Kyrs explained the whole thing to the assorted staff.

"You know," Destiny, one of my sexiest saleswomen remarked, "Normie is always threatening to cut our salary if we don't sell enough."

"But I also reward you with commissions and bonuses when-"

Monique slapped me across the face (she learns pretty fast) and Kyrsten told Destiny to continue.

"Why don't we see if he can make three sales this afternoon?" Destiny said. "Normie gives us shit if we can't do that-and it he can't we should be able to take turns on him with the paddle, why not?"

Sidra, my bookkeeper, who had it out for me ever since I'd drunkenly pinched her bottom at the Christmas party, volunteered "I'll beat his ass and his balls with my high heel if he can't make even one sale!"

I am no good at sales. It was a horrible afternoon.

April 4-Kyrsten tied me to a tree last night in the backyard during a thunderstorm.

April 7-Work is getting so weird now. Whenever I have to write someone up or when I try to give the girls a pep talk about their sales efforts, someone tries to humiliate me.

Monique pulled my dick out today when I was on the sales floor. Monique has a key to my Prince Albert piercing, and she unlocked it and made me hang my hard penis out of my Brooks Brothers suit pants while I lectured the girls, who of course wouldn't take me very seriously.

April 9-At work, Monique and Destiny made me go down on them on my knees in the Ladies' bathroom. I am in a catheter at work now, so that's all I could do.

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