Letter from Chicago

LETTER FROM CHICAGO

Dear Shoeblossom:

My name’s Noelle. I was just reading “LETTER FROM BOSTON”…That dopey rich boy Franz the Fool wrote you about how I was his Candy Striper, when he was in the hospital in four cast traction…and how I teased his cock and balls, and beat the crap out of him…and made him suck off my gay cousin! God, it brings it all back!

Truth be told, I was only on the Candy Striper volunteer bit because I had to do three hundred hours of volunteer work as punishment for selling crack jumbo red-top vials at St. Floriana’s, where I was a sophomore. Shortly after I broke off with that idiot Franz, I stole his car (didn’t tell you that part did he) and drove to Illinois, first to waitress in Skokie, and then moving to Chicago…

My first chastity slave when I got to Chicago was a Certified Financial Planner called Voltaggio DePinero. He was a strange fellow, and needed a lot of strictness, apparently. I put him in a glass chastity tube that didn’t allow him to masturbate or even urinate…and he had to buzz me with a beeper when it was time to go to the bathroom.

I was very entertained by Voltaggio, because I was working as a hot dog stand attendant in front of his big-ass office, and he’d buzz and buzz, and I’d take my time putting mustard and chili on various wieners, and then I’d lock up and slowly walk up to his office, taking the stairs as I gotta keep my ass small with exercise. When I’d see Voltaggio, he’d be jumping up and down in his office, and sometimes he’d be peeing out the side of the glass tube, ruining his expensive Armani pants.

“You sure you need to pee, sucker?” I’d say, as I stood in front of him in my little hot dog apron, which covered my meager bikini top and short shorts. I’d make poor Voltaggio drop to his friggin’ knees, begging for the key, so he could run into his private john and pee…and there was almost always an accident.

Then I’d lock his hands behind his back, take off his pants and shorts and toy with his dick for forty-five minutes or so, until he was ready to let me wheedle a tip out of him…and then of course I’d lock him back up again, and go back to the hot dog stand. He begged me to give up selling hot dogs, but it was such a great way to get a tan, you know?

I eventually split from the Italian and found a sub hubbie…and life has gotten even better! I turned poor Voltie over to  Caligula Simms, who owned my hot dog truck, and his sexy Negro daughters, Calcutta, Caledonia and Chinchilla…and now Chinchilla is Mrs. DePinero, and they all live with the poor bastard, keeping him in line!

And I married Elgin Pincus, a sweet and pliant attorney. My roommate had gotten in trouble over a bankruptcy thing, and Elgin handled it free of charge. and I, who of course sold my ass now and then, waved my boobs at him and said I’d make it up to him with a blowjob or something…and Elgin instead stripped naked and took a coiled cat o’ nine tails out of his briefcase and handed it to me! It’s been progressing from there…

My husband Elgin is a big fan of your Letters—he is also a pitiful chastity faggot! Well, not really a natural fag. He has no interest in men, but he has been trained towards servicing them for some time. I met Elgin through his sister, Indigo…Indi and Elgin were raised in a female dominated family, and Elgin’s mom put him in a CB-3000 when he was in high school, and gave the key to Indi!

It was up to Indigo, a shapely minx with a thatch of curly blue-black hair, to get her brother into shape. She started by whipping his bare ass in their playhouse in the back yard when he wouldn’t play doctor “right”, and then she continued on to developing training regimens and rewards to get Elgin to work towards  the privilege of jerking his dick.

Putting her older brother in diapers, giving him baths, and shaving and massaging his cock and balls without relief was part of Indi’s regimen, and then making him do nasty shit…such as sucking off his teammates on the basketball and hockey junior varsities…Elgin was known by the other student-athletes at the Chicago Lab School as “The Encouraging Mouth!”

In the sports that Elgin didn’t actually play in, such as football, baseball and wrestling, Indi, after a few vicious canings, convinced Elgin to go through depilation treatments and then he became a cheerleader! El is, although a good athlete, a somewhat slight boy, and with a little makeup and a poofy wig glued to his head so it wouldn’t fall off during the cheers, became the perfect pompom girl. Indi was the coach of the drill team of cheerleaders, and she’d do other private drills at home, urging the naked (except for wig and pomp pomes)Elgin with her hazel cane…he was quite graceful by the time he graduated from high school!

Indi actually made poor Elgin take her fist in his mouth and she’d shove it down his throat to mimic having to deep-throat another horny teenage boy…and she got him used to the taste of semen.

“You just had to get him used to cum.” Indi told me with pleasure. “Mom didn’t let El go out much at night, but when I came home from making it in the back of some loser’s Audi, I’d hop my cum filled pussy on Elgin’s face, and he’d clean me out, lickety split (so to speak) It really worked out well!”

Indi explained to me that the best time to work on a young man’s chastity development is in mid adolescence, when sex is all he thinks about…pheromones, testosterone, and lots of girls! And Indi could get her girlfriends to tease and tickle poor Elgin as he struggled with the nasty plastic chastity device lurking in his jeans!

Indi loved shaking her gorgeous, curly hair out, lining her lips with frosty cherry gloss and putting on a little camisole top…tying Elgin naked onto a hassock and rubbing her fingers all over his penis until it was about to typhoon! She’d gotten plenty of progress teasing her dad and her uncles, and that was always a good way to get spending money out of them, as well as other things.

Indi also told me about using a long heavy black metal flashlight, probing poor El’s asshole, shoving it into his rectum, making poor Elgin scream and moan as the metal light, all sixteen inches of it went in and out of his sphincter!

And Elgin and I have a similar situation, methinks. I use my retired cop uncle’s nightstick instead of a flashlight, but with Elgin bent over and crying, I can get the little wooden “Dictator” to do considerable damage where the sun don’t shine! I’m thinking of using a crowbar or a lug wrench next!

Suspending Elgin’s wrists from the ceiling of our garage on a Saturday night, I shake my breasts in his face…it’s depressing for him, because of course I’m not going to let him kiss them—that’s for boyfriends. I found a discarded fan belt last year that I like to use on his stomach and his buttocks as he sways about, lifting his legs up to protect his balls.

“What’s wrong, faggot” I ask with a full lipped smile, “Are you afraid I’m going to cut off your nut sack…or just slap it around?” If Elgin forgets himself for a minute, I step right in and kick him viciously in the scrotum, and he howls with grief. Sound like a screeching girl sometimes, it’s kind of sad. I often rub a bit of Icy Hot on his penis and balls too, just to see what his reaction will be.

What else is fun is to tie a bit of clothesline around his cock and balls, and step back and pull him towards me, as he is swinging from the ceiling…I pull him closer with my right hand and bring the fan belt down hard on his penis and nuts with my left, and of course there’s more screaming and misery. I like to crack, scramble and sunny-side up his eggs before I’m done!

But Elgin is a hard core submissive, and his dick keeps swelling to erection. He really does get off when I mistreat him. Usually after about an hour or so in the garage, I let him limp back in the house, and then he tenderly goes down on me as I lie back and scream with animal pleasure.

Sometimes, after that, I let Elgin jerk off on a pair of my Capezios, or let him rub his nuts and penis against the wall and have a squirt that way. I’m not always cruel!

Elgin certainly is a loving husband, and understanding in a thousand ways. He’s a little older than I am, and not interested in going out partying and nightclubbing, which of course has been a huge part of my life since about seventh grade. When I’m out in my little shiny slut outfits, flirting with college boys, Elgin is usually at home, locked in chastity of course, usually reading Greek History or working on one of his jigsaw puzzles.

When I come in a night, he looks at me longingly, and I let him undress me and give me a full body massage…he loves to run his hands over my curves!  And then he worships my labia like it’s going out of style, if you know what I mean!

Poor Elgin’s cock is very crushed in his chastity device, and I am amazed, continually that he doesn’t complain at all. When I give him permission to cover my full breasts with kisses and to lick my stomach and then worship my sexy inner thighs, I can tell he’s in a bit of pain. After all, he hasn’t cum in some time, and his poor penis is helplessly getting over swollen with extensive back loads of cum!

Now and then when I come home from the clubs, I’m in a bad mood. Some guy may have rejected me, or behaved like a jerk. I obviously need to vent, and then again Elgin is incredibly patient and understanding.

Elgin sets out the implements in the bedroom, strips off his nerdy sweater-vest and the rest of his ugly clothes…and lays down on the bed quite patiently, waiting as I put on the tweezer nipple clamps, lock his hands behind his back and his ankles together, and push a pillow under his crotch to make his buttocks an enticing target!

One favorite of mine is the birch. A birch is a bundle of thick thorny twigs and cracks with real pleasure as I lash it across Elgin’s narrow ass…It’s given me real arm swinging!

Then I have what’s called a Liquid Cane…it’s eighteen inches of solid neoprene rubber, and long and sharp looking…I love it “This…asshole…at the Enclave club grabbed my tits and told me I was meat!” I screamed one night as I lashed the Liquid Cane against poor Elgin’s butt, and then I spun El over, and unlocked his dick and whipped that too, as a representative of evil men everywhere!

I have a cute thing called a Cowpoke, bound leather with about fifty tails coming out of it. It’s shorter than a whip, but has made Elgin scream so loudly that he almost fell off the bed, trying, while bound to inch away from the stinging lashes!

And then I have a seven foot bullwhip, and a twisted cane driving whip which is made from four splits of cane, and then covered with quite painful and effective nickel plated mounts….After I’ve worked Elgin over with these, I turn his weeping little body over and I’m feeling more generous.

Unlocking Elgin’s chastity device, I sometimes strip down and plop my pussy on his raging cock…but just the tip, you understand. Very, very lightly, I run the tip up and down over his purple glans, getting him quite excited, before I climb off again and just begin breezily rubbing and tickling his little wee-wee.

I love just tracing my forefinger up and over Elgin’s stuttering glans, running it down the sensitive underside of his dick..whaddya call that? The frenulum? Sometimes we have conversations about various household matters as I do this, and he of course is quite distracted.

I love to rub my hands over my clothed breasts. I’m usually still wearing my hottie clubwear at this point, and my cleavage is in plain appearance. Elgin’s glasses begin to steam over and I generally take them off and wipe them so he can behold my hottitude more clearly if you know what I mean.

Then I like to play with his full ball sack…by this time it is rather huge…after months and months of prolonged chastity. There’s a lesson there somewhere, eh Shoeblossom? Eventually I lock poor Elgin back up again and get him to make me a late night supper…all feeling better!

When I bring a lover home, it’s much tougher. Especially when Elgin has to watch us make it. Sometimes if the guy seems like he’d freak easily, I order Elgin into the closet, other times he kneels naked as we go for it.

I do not allow Elgin to kiss my breasts, except on holidays and birthdays, and he gets terribly depressed when whoever I bring home begins worshipping my cleavage, and then ripping off my bra and kissing and biting my breasts…but life is full of adversity, isn’t it?

It took me a long time and a number of whippings to get Elgin to participate when I had a guy who didn’t mind it. I like ordering Elgin to like, suck a guy’s balls while I suck his dick, or suck the balls while the guy fucks me.

At first I would tell Elgin that he could jerk off, a rare privilege after he serviced one of my boyfriends, but then of course I wanted him to do it for the joy of the service. Not because he was going to get some sort of bullshit reward. I mean, how fair is that?

I have one boyfriend, who is a former close buddy of Elgin’s named Jimbo. It was of great interest to Jimbo to discover that not only would Elgin no longer be able to watch football with him or throw darts, bowl or play pool…but also that I wanted Jimbo to assist with Elgin’s training!

“Please, Noelle darling” El begged me.”Jimbo and I have been friends for years. We took the Illinois Bar Exam together…don’t do this to me.”

“Look, if you want to just have a normal marriage where I suck your dick and treat you like a regular husband, that’s fine. You can play with my tits, and I’ll be faithful” I raged, “But if you want me to be your dominant wife, then you’d better do as I tell you, Elgin.”

But in the end, Elgin actually got quite excited by being forced to be humiliated and pushed around by his former best buddy. The first time Jimbo took Elgin over his knee and pulled down his pants, whipping him with my thick wooden paddle, at first there was some jokes between them…”Don’t enjoy this too much, Jimbo” and that kind of thing…

But by the end of the evening, Elgin was naked, cowering before “Master James” and kissing his feet, licking the grime from between Jimbo’s toes. He was watching respectfully as I fucked Jimbo’s brains out, and then he was licking my juices and Jimbo’s sperm off Jimbo’s dick and out of my pussy. Jimbo called him the “bidet.”

The first time Jimbo fucked poor Elgin in the ass, I think it really broke Elgin emotionally. Elgin is fairly masculine in a lot of ways, he can box and all that kind of thing…and he can actually kick Jimbo’s ass in a fight…but now that he is ordered to obey Master James, it’s all different, and I got Elgin to suck Jimbo’s dick until it was quite hard, and then turn around and take it with  nice big ramming, in his tender anus.

Sometimes I go to black bars, and bring home horny, African American bucks, and then I tell them they  have to whip poor Elgin’s ass for me. This produces quite a bit of mirth in most black men, who feel, of course that they are terribly oppressed.

They are amazed when Elgin comes out in full makeup, with his balls locked in a wooden Humbler behind his legs, and I go after him with the cane. It’s improbable and amazing that a white man, Lord of Creation and all that, would take that kind of treatment!

The other thing of interest is that Elgin’s son from his first marriage has come to visit us. He is called Bunny, the little preppie asshole, and reminds me of that idiot Franz. Bunny is in his mid-teens, and I have now locked HIM in chastity, and I whip his bare ass and twist his nipples violently when his grades are not up to par.

It really brings back the memories, when I have Bunny tied down and I’m rubbing his dick with Vaseline as I wave my tight sweatered honeys at him. Bunny gets so frustrated. I love to coax an orgasm right to the tip, and get him so he’s so thrilled that he’s about to lose his sixteen year old mind, and then I punch him in the balls and go in the next room, listening to Bunny’s wails.

I grant Bunny rare orgasms if he does something that is not in his nature, such as learning to knit a sweater for me…I began him on finger-knitting, and then we moved to the needles. As I kept him naked during the lesson, I could poke his balls when he seemed to be falling behind! Isn’t that hilarious?

I also give Bunny, otherwise Elgin Thaddeus Pincus IV, access to Stepmommy’s body, Not that he gets to fuck me, but all the kissing he wants…and he loves it, and rarely goes home to his permissive mother. It’s much more interesting at my place, though next year, when his Aunt Indigo and I train him to suck off his teammates at the Lab School, his attitude may change, right?

Best, Noelle.

Dear Noelle,

I am glad that the MidWest is also as interesting diversity and leather wise as the rest of the country.  Elgin and Elgin Junior are going to learn what the world is really about…through their gorgeous domme, and why not?

Best, Shoeblossom