Dear Shoeblossom:
I have read with interest your letters from chastity belt couples. I really thought I was an enthusiast, but now I think it may have gone too far. My love affair with chastity and denial began, I think, in my early twenties. In the summer after my junior year at Harvard, I wrecked Dad's BMW while drunk on the Montauk Highway, near our vacation place, and broke both arms and both legs, and I began getting visits in my hospital room from Noelle, a Candy Striper volunteer...she was an impish redhead, and after some conversation, began giving me an impromptu hand job one afternoon.
My family was of means, and I had a private hospital room, and Noelle locked the door. I of course couldn't move, but was happy to make out with Noelle, who gradually began shedding her Candy Striper outfit, until she was just in lace bra and panties...
Noelle shucked down my pajama bottoms and began stroking my cock, and she rubbed and toyed with it, and as I got more and more excited, Noelle of course rubbed faster...but when I got to the point of cumming, she stopped kissing me, pulled her hand off my cock and slapped my face!
"What-what's wrong?" I asked, stunned. Noelle laughed, jiggling her black-encased breasts at me, and slapped my face again. I was absolutely helpless, as I was in traction, and I just looked at her helplessly.
My dick, suddenly free, waved around, wondering where the wonderful stimulating hand had gone...my balls were quite full, as Noelle had been rubbing my dick for nearly an hour...what the hell was wrong with her?
"You don't remember me, do you, Franz? You and your preppie friends are always coming into the townie bars and making fun of us townie kids...and now you're a little lonely, right?" Noelle had grinned at me, and she began stroking my cock again, faster and faster. "You don't like not getting to squirt, but you're just a rich little shithead."
Suddenly, and with great vehemence, Noelle rolled me over on the bed, my arm and leg casts bouncing, and while on my stomach, she pulled my pajama bottoms down further, and out of the corner of my eye I saw her pulling my belt out of the pants on the chair.
"You're just a worthless preppie trust-fund pig!" Noelle shouted, and she lifted the belt and brought it down hard across my bare buttocks. WHACK! WHACK! WHACK! I screamed and tried to move but the casts held me down. I had never been spanked in my life—my parents had mostly been abroad and I was raised by indulgent nannies and governesses, before going off to boarding school at age twelve.
"Scream all you want, asshole, I told my sister, who is Head Nurse on the floor, to take a powder. She's had to put up with your whining since you've been here all week, and she's fucking sick of it." And Noelle recommenced with my belt, this time buckle first!
Finally Noelle threw down the belt, and I heard some noise, and incredibly, she cut the cord to the VCR and came up behind me again. The VCR cord whipping was like nothing I had ever experienced. I screamed and howled, and Noelle whipped me until I was cried out.
Then, she took a basin from the corner of the room, and I felt her rubbing a washcloth across my ravaged buttocks, getting the blood off, I assume. "You're going to learn that money's not everything...I'm sure you're a sweet guy in your way, but your behavior is just execrable." I was surprised that was a word in the lower classes vocabulary, but said nothing.
Finally she turned me over and began sponging my cock and balls, running her nails up and down my suffering penis. "See, that's all you think about...your pleasure." Noelle said. I hardly noticed when she picked up the VCR cord again, but certainly, as I was about to orgasm, the cord was brought to my attention.
THWACK! The cord hit my cock and balls hard. CRACK! "I think you're starting to get how annoyed I am with you, Franz."
The cord lashed my dick and balls five more times, and then Noelle dressed and left, and I couldn't wait for her to come back again. I had never gotten to cum, and of course I couldn't move my arms and legs, as they were in heavy casts.
I don't know why I didn't tell the doctors about this, probably because I wanted Noelle to return. I remember thinking that if she could just let me cum, she could beat me all she wanted!
Noelle came back the next day, and this time she brought some Astroglide, and she stroked my cock for four hours, still never allowing me to cum. At the end of the third hour, Noelle's best friend Anita showed up, and Anita was a bubbly blonde, and Anita thought it was hilarious to play with my balls as Noelle stroked my cock...When the girls left, I was out of my mind with frustration!
Twenty-four hours after that, Noelle showed up again, this time not dressed in her Candy Striper uniform, just wearing a cute little miniskirt and halter top. After she'd stroked me for a couple of hours, she asked me if I wanted to cum, and I, now having been teased for eight days, nodded my head. "Would you do anything?" But of course!
Noelle used her cell phone to summon her gay cousin Aidan...she reminded me that my pals and I had roughed him up one day, kicking his teeth in and bloodying his nose outside of the town's only gay bar. My dad had made the charges go away and Aidan's dental bill had been paid, but Aidan was still angry.
"I want you to make Aidan happy!" Sucking Aidan's dick apparently made him happy, and he came in my mouth, and I felt a little ridiculous, as of course I was still in full traction...but after it was over, Noelle pulled her panties down and hopped on my cock, and I came hard...and all was bliss!
But then Noelle found some Ben-Gay and rubbed it in my asshole and had Aidan corn-hole me for about an hour and a half. This made me regret my desire to orgasm...it really made the word hospital be associated with being sick, and all that!
After the casts finally came off, Noelle and I went out a few times...she'd make out with me, and accept expensive gifts, but the only way I got to cum is if I sucked Aidan off...and it was a long blowjob summer, let me tell you!
Much of my post-Noelle chastity training I owe to various professional dominants—before I began dating my present spouse, I was seeing a Chastity Mistress, called Mistress Maunders. MM, as I remember her had me in one of her own chastity devices, a tiny pink plastic thing, quite humiliating.
I'd found MM's ad in a seedy newspaper I bought in the Combat Zone, which is Boston's red-light district. Her advertisement was something like this:
"Are you a man in need of supervised masturbation? Does your sex life get in the way of your work or your studies? I am a trained Tantric Onanologist and lifestyle dominant, and will take charge of your orgasms. I also offer physical discipline and a very strict regimen of achievement...if you are a card gambler, you may well enjoy what I've got to offer!"
And I was a card gambler! A stupid rich boy, I lost quite a lot in bridge and poker games in the Student Union, but fortunately, had enough left to pay for MM's expensive "program."
I was about twenty and MM had to be my age or older, but she looked about seventeen, a little eighty pound blonde thing with big boobs and full lips, and enormous blue eyes...but quite tiny! She'd given me the price for the pink plastic chastity lock, which resembled a faucet, and also her weekly rates...and she'd locked the thing on me, after I'd handed her a thousand dollars.
Mistress Maunders climbed on my lap, after locking me up and kissed me madly. Plunging her tongue in my mouth, she whispered "You'll have a ball with me, baby...but only if you're a good little gambler, get it?"
She'd dismissed me then, and I went back to my dorm, and wouldn't you know it, the next night, I was making out with MaryAnne DiNardo, and when she said "Let's go all the way" I couldn't take off my damn pants, because of course, I had the little belt locked on me!
And I had to shower alone, and keep a towel over me. and within three days, I was going nuts, as I was a five time a day jack off junkie...but MM wouldn't see me again until I had $500 for the uh "consulting fee".
When I got there, MM showed me a deck of cards and told me that there was little chance I would be allowed to masturbate, but that I should pull a card from the deck ANYWAY.
Then she explained my chances.
If I pulled Seven of clubs, seven of spades, king of spades, ace of diamonds, ace of hearts, knave of clubs, four of hearts, eight of hearts, or knave of spades then I would get no key, and all I'd be eligible for was a thirty whack whipping from her trusty oak cane.
If I pulled Two of diamonds, three of diamonds, two of hearts, six of hearts, king of diamonds, five of clubs, two of clubs, five of spades, or three of hearts, I'd be bound naked and she'd tease me with her nimble little fingers for an hour, and then I'd be locked up again and sent home.
If I pulled five of hearts, six of diamonds, four of clubs, or queen of clubs, I would be unlocked and ordered to jerk off in front of MM's open window, without being allowed to orgasm at the last minute.
If I pulled five of diamonds, three of spades, king of hearts, four of diamonds, or ten of spades, I would be given a twenty minute "sand paper" teasing (very painful) and then be spun over and whipped with her hairbrush, locked up and sent home.
