Kip's Letters & Kip's Diary

(MmB) (anal, fist, oral, rim., scat, ws) (humil) (beast, inc) (some female)
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  • L 07
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  • D 01
  • D 02
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  • D 04
L 01

November 26, 1999

Hey, how's it hanging? My name is Kip Ketter and I am an eighteen-year-old gay kid from the Midwest. I am five-feet, ten-inches tall with short black choppy hair. I have a nice smooth muscular body as I was on the swimming and diving team in high school. Although I am shy, Dale has instructed me to tell you certain other intimate details about myself. He says to tell you I have well-developed pecs with nice big nipples, a flat tight tummy, a well-trimmed prick bush, an eight inch cut prick that is nice and thick with a big head, a pair of huge low hanging balls, a tight smooth ass, until recently virgin, strong swimmers legs and size ten and one half feet. There. I guess that describes me. Although I could get good grades in high school when I applied myself, I was a jerk-off too often and so didn't do particularly well. If this little project turns out as Dale intends, he has promised to send me to college and take care of my financial needs.

What is this little project? Little for you, huge for me. Well, Dale wants to turn me into a completely degraded, humiliated fuck slut. I don’t know how else to describe it. You see, he found out I get turned on by the fantasy of sexual humiliation and he decided to turn my fantasy into a reality. However, I'm getting ahead of myself here. Let me describe my sexual life and my relationship with Dale.

I first fucked a cunt when I was sixteen. I was pretty popular in school and known as a wild partier. The cunts have been after my body since I was fourteen.

My home life was and is shit. I've got no dad and my mom is a wine sipping suburban alchy who whores around looking for her youth and someone to love her. I feel sorry for the bitch, but she is such a sow. My little brother and sister are even more neglected than I was, and I fear will turn out worse.

So anyway, I fucked my first twat at sixteen, at a party. The twats really love my big pink dick cause it is very thick. I fucked girls more as a status symbol than for enjoyment, although I didn’t know that at the time. I thought that’s all there was to it – fucking I mean. In-out, bam-bam, fuck-fuck, shoot!

Frankly, I enjoyed beating my meat more. And when I beat off, which was a lot, I often fantasized about guys getting worked over by other guys. You know stripped in public, hazed, club initiations that sort of junk. I found myself thinking about other guys bodies and imagined them working me over. I would do stuff like tie shoelaces around my nuts, stick Q-tips in my pisshole, shove a pen up my asshole .and it would get me very excited, but that’s as far as it went until I met Dale.

You know him as the writer of the Mr. Black series and Lakeland Lads and stuff like that for assgm. I first knew him as the director of a theater company in our city. You see I had dreams of becoming an actor. Still do and Dale says he will help me get into a good drama school if I complete this project. I auditioned for one of his shows and got a part. He's forty, good looking and openly gay.

I was seventeen, good looking and in the closet and what resulted was inevitable. He fucked me silly. He turned my tight, virgin, boy asshole into a stretched out fuck tunnel. He made a fucking dickwhore of me.

It started when I was getting measured for a costume standing there in only my underpants. Dale pushed his hand up under my balls to get an inseam measurement. I threw a tremendous boner. It surprised me as well. I admit now I had a slight crush on him already. He is popular, very talented and is surrounded by good-looking guys all the time. I don't know if he sensed my submissive nature or if he was just testing me or what, but he told me to follow him and he walked out of the costume room, down the hall to the stage with me following him in only my underpants.


It was like one of my fantasies come true. I felt terribly humiliated and embarrassed, but excited all the same. Why was I following him? What was it? There were about fifteen other guys in the theater and I just tagged after him like a puppy, almost naked wearing only small white briefs with my big package pushing out the front.


The supposed reason for the journey was for Dale to ask the advice of his production manager about a costume, but it really was to expose me to the crowd and to see if I could take orders. They talked about my big nipples and how good they'd look on stage. They poked and prodded my crotch and ass as they pretended to talk about costumes. I got so fucking excited I almost came right there. He kept me in just my underpants for over an hour.


After that I hung around with Dale all the time, going out after rehearsals for burgers and stuff. I learned a lot about theater and was smitten. I also sucked his dick after three dates, if that’s what you want to call them. I'd never had a prick in my mouth before, and Dale's is quite a meaty mouthful. He fucked my face hard with little romance. I dug it. I felt so good just being a dickhole. He could sense that. He would unload wads of cum into my mouth insisting that I swallow and he had me taste it, gargle it, spit it into a dish and lick it up again. Stuff that was freaky, but really turned me on. That weekend, he fucked my virgin ass for the first time. It hurt like hell and turned me on even more. He fucked me hard and deep like a cheap whore. Slamming into me as his big balls slapped my asscunt. I thought he was going to rip my asshole out. I 'd never felt such pain, such pleasure, such piggish dirty slutty sex. I never felt so hot being used like some useless cumdump. I told him about my feelings, and he said he'd guessed that was the case. That's when he gave me some of his stories to read. They blew my fucking mind. The things done to kids in those stories were much wilder and more freaky than I had ever allowed my imagination to be. Then he told me my real life could be like that. We could play games – sex games, submission games, humiliation and degradation games. We could make my fantasy a reality. The only difference would be that in the stories the kids are forced to do stuff. I would submit of my own free will.


We tried some mild experiments. He gave me a part in a show, Oscar Wilde's Salome, where I had to appear in front of the audience in just a pair of tight small underpants and tongue kiss another guy on stage. I really dug it. I beat off all the time thinking about what I was doing in front of audiences. It was much better than any of the cunt fucking I had ever done. Meanwhile, if I was a good boy, of course, Dale rewarded me with his dick. If I fucked up at rehearsal or out of it, he deprived me of his cock and fucked some other young kid instead. It got me insanely jealous. I could have had gay sex with other actors I met, but you see with me it’s not just the sex, it is definitely the humiliation and abuse and degradation. I get most turned on when Dale give me some really gross order and I have to complete the task to his satisfaction. The worse the command, the more it excites me. After a show, he'd tell me, ":go and collect the dirty jockstraps from the guys for the costume lady, will you?" I'd trudge around carrying the sweaty prick pouches of the actors in my bare hands.my dick straining to shoot. He know exactly how to push my buttons.


Next, he had me appear completely bare-assed in a show letting everyone see my cock and balls. Not only that, but for the last few weeks of rehearsal, he made me rehearse bare-assed naked with the rest of the cast clothed. He told them it was to get me used to it, but I knew it was to humiliate me. All the guys and gals kept looking at my cock and balls. Of course, I was forbidden to date any other girls or guys – not that I wanted to. Dale did have me suck off lots of his friends. I became a cast party mouth fuck.


He would wander over at the party with a couple of dudes and casually say, "These guys think you're real cute, Kip, just suck them off for me will you?”


I was a dick whore at seventeen. Sometimes he'd order me to dance for the guests at cast parties and of course strip until I was bare-assed with my big dick and fat balls flopping about to the music. I felt wanted, needed, appreciated for something. For my eighteenth birthday, Dale took me to my first gay bar. When we were there, he ordered me to undress in front of about fifty guys. It really freaked me out. I was a little drunk. I cried and cried, but I stripped. All the guys fondled me and I got a big hard on right in front of everyone.


I've been living at Dale's house now four or five nights a week. The games have become more intense. He often keeps me naked around the house even ordering me to answer the door bare-assed. It’s awful when the paper boy comes to collect or a pizza is delivered. He knows it secretly excites me, even though it is very hard to do. He makes me eat out of a doggie dish on the floor at times. I can only piss and shit after getting permission from him.


Now he wants to step up the game. He conceived of this project. He will pay for my college or drama school if I become a total fuckslut, cuntboy, sex slave for one year. He knows it is what I secretly crave, but am too scared to initiate. I long to be completely degraded, worked over, made to do the most disgusting things like one of the boys in his stories. I want this for real, but am terribly shy. Christ, I never even wanted to undress in the locker room at school.


Well, I agreed to Dale's conditions. The first time I refuse to follow an order or do what is asked of me, I am out on my ass. I could have continued just as Dale’s sometime boyfriend, but the excitement of this project completely dominated my mind. Dale has promised me that no damage will be done to my body. Who can say what will happen to my mind?


So far the commands have been easy. Dale says my descent into becoming a boycunt, cumslut must be gradual so we can savor the humiliation. He has ordered me to suck off two guys a day – two strange guys so I have to go out hunting. Of course, I am young and good looking.so it is not difficult to pick up guys, especially older guy. The only trouble is they often want to suck me off and I have to convince them to just let me give them head. I love the taste and smell of dick. I am becoming addicted to dick. Fucking and sucking is all I think about. Dale has put me on a temporary sensory deprivation routine. I am allowed to watch no TV or movies except gay porno and read nothing except the plays we are working on and porno magazines so cock is constantly on my mind. He makes me describe to him what I imagine the cock of every guy we meet looks like. He makes me write long papers on dicksucking and ass fucking. He even made me write a paper for him imagining what my fourteen-year-old brother's dick and balls must look like and how it would taste. Imagine me thinking about my own little brothers prick and sack.


My fourteen-year-old brother just started to fuck girls, so Dale makes me shove a dildo up my ass and pretend I am one of his young school cunts being fucked by him.


"Oh fuck me harder, Mike. Fuck me harder." I have to scream, ramming the dildo in and out of my ass pussy in front of Dale and his friends. Sometimes he even makes me kiss and lick a photo of Mike while I play with my swollen, dripping dick. He keeps my dick that way, right on the verge of cumming. It drives me insane. I am a totally sexed up teenager twenty-four hours a day. Dale tells me I am at the age when a male is most horny and I believe it. I almost go crazy at times sucking and fucking and not allowed to shoot my load. When I do cum, of course, it is like a fucking firehose. I cum so hard it hurts.


Well, here's where you come into the project. Dale would like to try a totally new internet experiment. He wants you to help with my training of humiliation and degradation. He wants you to give me orders or even just suggestions. He will see to it that I obey them and write about them in my letters. They can be as far out and sick and twisted as you like as long as no permanent damage is done to me. Shit, I got my dick all hard and dripping just writing about this. I will not only write about my completion of your orders, but I will email you personally to share my feelings with you. I don’t mind telling you I am scared. Dale is excited about this project. He says together you can really fuck me up and work me over real good. He says the things you can make me do are endless. He suggests that you start out slowly and mildly, one step or crawl at a time. He will monitor the orders and give them to me in the order he thinks best. I am really scared, but also more excited than I have ever been in my whole life.


So here, I am at your mercy. Your own eighteen-year-old private, cuntboy. Your twat mouthed pussy assed teenage boy. Do with me what you will. Your every wish is my command.


Some things you should know about my life.


I work at a trendy restaurant where all the fashionable young go to party and pick up fucks, guys and girls alike. I am a waiter and not a night goes by when several guys as well as chicks don’t ask me to fuck.


I belong to Bally's Health Club, but don’t go much as I say I am actually very shy. I want to swim more.


I live at Dale’s most of the time and will email you from there, but I do go home every few days.


At home is my mom trying to be young again and looking for love in all the wrong places. She often has her latest young stud staying there with her. My fourteen-year-old brother, who is pretty wild and uncontrollable and my twelve-year-old sister, who is pretty much to herself.


My brother has a dog and a cat. The dog, Soldier, was mine, but I can’t take him around with me and my brother really likes animals.


I currently get ass fucked about ten times a week. About three or four times by Dale and rest by his buddies or some guy in a bar he will order me to go with. I love the adventure and thrill of letting a strange man fuck my asspussy. I love feeling as if I am just a young cunthole for him, the way most teenage guys treat girls, just dumpholes for their dicks.


I currently suck off about twenty to twenty five cocks a week including Dale’s whose I suck almost every day. Dale says I can do a hell of a lot better in both the ass fucking and dicksucking department, but he says the increase will be gradual. He tells me his goal is eventually to have me sucking and getting fucked all day and night. Constantly.


I of course am not allowed to jack off without permission. I last came a week ago. My balls are really heavy and swollen with cum. I get blue balls real bad getting fucked and sucking, but not being able to cum. Dale says I have to learn to serve before I deserve getting serviced. Reading porno and watching porno videos keeps me on edge all the time. I am always sexed up and sometimes cannot stand the pressure. If I cum without permission Dale beats my ass – sometimes with a belt.


My body is kept hairless except for a small well-trimmed pubic bush and a bit of hair beneath each armpit. Sometimes Dale makes me pluck out my ball hairs with a tweezers. He loves to play this game. He told me he plays this a lot with the boys in Thailand. He pays them to pluck out their nut hairs. To teach me humility Dale will make me take out my dick or undress in public places – in shopping mall toilets, in movie theatres, in the car. He’ll make me sit bare-assed and beat my meat in his car as he drives the highway passing trucks where they can see down. I get so scared I get sick, but it still thrills me. Dale says I need a lot more public humiliation.


So, I appeal to you. I am only eighteen, but I hope I can degrade myself enough to please you. Nothing is taboo. Join Dale, won’t you in my training. I await your orders.


Yours in all humility,



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