Letter From New Piedmont

Dear Shoeblossom,

I can still remember Rebecca's first comment: "You sure you want to do this, kid?" A full-figured ash blonde with brightly glossed lips...pure Jersey girl.

"You really want to move in with me...the sessions aren't enough?"

Sometimes the sessions were way too much, but I was lost without Mistress Rebecca.

46 to my twenty-three, she'd been my Keyholder for about eight months. And now, having gotten a slight raise and a window office from the good folks at Dougall & Dermott Properties, I wanted to pay for a room in her castle...

I'm not that unusual.

They call me Thumbs (an old Little League nickname) and like a lot of your readers, I was hot for the idea of being kept in a chastity belt, and meeting with a dominant professional now and then to have the belt removed and cleaned...

And for me to get some teasing and discipline. Rebecca was great at this, and I loved talking to her.

Rebi had taught me to take a good spanking. I was raised by therapy-head parents, and had never been hit.

I'd fantasized about being whipped over the knee on my bare bottom, but even when I'd gone to other dommes, I couldn't take a lot of pain.

Rebi started me off with a cooking timer.

She'd set it the first time for about ninety seconds. "I'm going to hit you hard, Thumbs, and as many times as I can in a minute and thirty seconds.

Try to hold off as I whack you. And remember, it'll be over in a minute and a half."

That first time was so hard.

I'd bared my buttocks and lay across her beautiful fishnet stockinged knees, and the whacking started.

The whole humiliation thing that I got off on began to disappear as I began focusing on enduring the intense pain.

I began shifting, that first time. And Rebecca stopped the timer. "Shhh, baby." she soothed. "I'm going to start again, and you can be my big brave boy, can't ya?"

But I was falling apart. I nodded and she started the timer again, but within ten seconds I was trying to climb off her lap.

My butt felt like someone had fried eggs on it.

Rebecca let me stand up, almost stumbling over the Rogers Peet trousers twisted round my ankles.

Rebs had me sit very gently on her lap, and she rubbed my hair while I sobbed.

"Honey the only way you can determine your limits is by passing them. Y'know?"

I was gasping and quivering, and not too communicative.

"See, Thumbs, it's scary to change, and there's a lot of discomfort.

But if you're changing for the better, the tough times-like this valuable discipline-will make you a better man. Or not really a man, but a nice male."

Rebecca had kissed my tears away and I had tried to bite my lip. She'd taken off my chastity belt when I'd come in for the session, and I was still stiff with 38 days chastity that time...

Rebecca rubbed my tumescent, swelling penis with her reddish-orange nails, and the tender fingers got my penis all a shudder...

"You know Rebi loves you, hon.

I have to charge, but I care so much for you, and I know, Thumbsy, you can be a big, brave boy...

And not wail like a little bitch just because I hit you a few times. Don't you want to finish this, it's just a few more seconds, and I stopped the timer.

"I-I guess so." My penis had swelled as I thought of what a little sissy she thought I was.

During one of my previous orgasm release jack off sessions, Rebi had invited some construction workers over who had been working on the roof next door, and they'd laughed uproariously and thrown beer cans at me as I'd jacked away while wearing a pink frilly garter belt...

"I-I don't mean to be a sissy, I want to be a strong guy-Rebi"

"I know, honey. Like Pinocchio, you want to be a real boy. " She paused. "But Pinocchio at least, had wood." Rebi laughed before continuing.

Thumbs, you're basically a crybaby. You told me about how your big brother made you wear nail polish and the kids called you a little faggot-and then all those girls just wanted you just to be their non-threatening male friend.

"Y-yes, but I was a good listener."

"No, honey. It was cause you weren't very manly. They wanted you to carry their books, buy their sodas. I'm sorry you didn't lose your virginity till you were thirty-one-"

"No, I was twenty-three when I got laid the first time."

"No, baby, you said the first time you didn't pay for it, you told me was age thirty-one. On your wedding night to a girl who left you within ninety days...

Buying prostitutes doesn't count. But you can be manlier if you take a spanking from me, for what's on the timer, and not whine and bitch, okay?"

"Uh, okay"

"Seventy seconds still. Are you ready?"

I was still crying. "Y-yes. B-but can't we-"

"Be a brave guy and afterwards I'll let you kiss my titties while I give you a hand job. But only if you do the whole three minutes."

"THREE? But it was only-"

"You love my tits, kid. You wanna kiss them?"

"Yes, of course. I'll grit my teeth."

By the time I'd been visiting Rebecca six months, she could set the timer for twenty minutes, and I'd grit my teeth or bite a pillow through the hideous experience ("I stop when I hit blood, honey.")

But then of course, I was no longer rewarded with the hand job or the tits...I had to take it as a pure punishment...but I learned!

And of course when I screamed "FUCK" after one terrific swat, I was forced to eat an entire box...six Lifebuoy cakes of soap.

Hairbrushes gave way to canes, then razor strops, and finally the occasional bullwhip...

Diogenes was the head of a band of Gypsies who had come to New Piedmont with those home improvement scams.

But when he'd tried this on Rebi, she'd somehow hypnotized and enslaved him, as well as his entire group of malcontents.

Rebecca had the entire gang of Gypsies living a couple of miles away in an apartment building she owned, doing legitimate construction work now...and giving her most of the money!

But Diogenes didn't regret any of it-especially since Rebecca was sending his grandkids to university with a lot of the proceeds.

But he told me "I know the pain from the whippings hurts.

Let me give you a tip. Stay in chastity for longer periods of time, and the pain will be converted into pleasure through your sexual tension."

Diogenes laughed. "Once I annoyed Rebi so much that she had me masturbate BEFORE my whipping, and boy did that whipping hurt more...

Pure pain, like the thrashings I got from my father as a teen!

Yes, the secret is to hold off your orgasmic privileges as long as possible."

"Dio, is there anything you don't react well to?"

"I wish Rebi wasn't so fond of those ice cold chicken soup enemas."

"Chicken Soup?"

"Yeah, she wants it to be edible for me after I shoot it out my asshole."

I had seen Rebi give Diogenes and several of the Gypsy males harsh whippings at her dungeon expos...

And yes, they were all in chastity, as were the women...and all voluntarily. I was not aware this was a secret to withstanding pain-sexual tension.

I rarely was allowed to masturbate, and when I did, I had to lick it up. So I tried hard not to ask for release.

But I really became a good submissive!

The time in between visits to Rebecca was, of course difficult.

Being locked in the chastity belt was a tough time...no stimulation, and no release!

I couldn't jerk off, and being locked while watching hot little Megyn Kelly on Fox News, or when I foolishly surfed the porn on the Internet could be quite frustrating.

Sometimes two to five cold showers a night.

And, after one of Rebi's canings, I really did have a hard time sitting down...

And I couldn't work out for days, because of course the long weals and red marks on my ass and back and upper thighs would look creepy in the gym shower rooms.

Realistically, I knew if I lived with Rebecca, the punishments would be coming harder and faster, and that I'd be even more frustrated, because I'd be teased more, and released about the same amount-every six weeks or so?

But it was fun spending time with Rebi, even in the non-scene context. She was uneducated but bright, and made funny comments.

We went to the Zoo together because she wanted to see the penguins, which reminded her of submissives she'd had as a Domme in Washington, D.C.

As we walked by the lion cage, Rebi rubbed her red nails on my arm. "Yeah, you're so much like the husband in the cage there. The lioness does all the work, gets the food, raises the cubs, in the wild I mean."

Then, I recall I stared at some girl's miniskirted tush and Rebecca got annoyed and slapped me across the mouth-lots of rings.

Yes, when you get smacked by a hand with rings, it makes you wake up...

Everyone is staring at us, families, etc. I was horrifically embarrassed, and my jaw was numb. Even number than after I'd spent an hour between Rebi's legs.

"Goddamn it." Rebecca spoke loudly and sharply. "Thumbs, you shouldn't look at other women when you're with me. And, that girl was barely nineteen. Humiliating me at the New Piedmont Zoo."

And she'd stalked off, her own peachy posterior bouncing as her high heels clicked past the leopard containers.

I should have just walked home, but of course I followed her, beseeching for forgiveness, and then Rebecca turned back, laughing.

"That was hilarious.

You looked like such an idiot. I shoulda made you take your pants down, and used my handy-dandy razor strop on you, or at least pull your penis out for a little lashing."

Would she have done this to me at the New Piedmont Zoo? I was mortified and, of course very aroused at the idea of it.

She'd often insist that when we went on our "dates" I go without underwear.

And Rebecca would remove the chastity belt in the car, and play with my dick in the box at the Davin J. Piedmont Opera House.

Or stroke me at the stadium, where we had seats above the fifty-yard line, and separate from other people.

Once or twice we went to church together and Rebecca had cut a hole in my right pocket and just run her hand in right next to me in my family's pew and rubbed and stroked all the way through the sermon...

And of course, as we are leaving, me staggering with intense desire, my dick practically ripping out of the pants, Rebi winks at the bishop, who blushes.

And then she said...

"Mordecai, I'll be expecting you in garter belts and heels on Friday!"

And the bejeweled curate looked at his feet around the astonished parishioners..."Yes ma'am."

Madge, a bitchy commercial real estate broker ("I don't show houses, I build shopping centers.")has lived in Rebecca's house for some time.

"You know, I terrorize my employees, made men cry, etc. Then Rebi had me give a Pain Party-all my staff came, and I was bound, kneeling and naked.

Everyone, from fellow partners to the receptionist and the guys who mopped the floors-

They all took turns whipping my ass with paddles and quirts.

I was skull fucked by custodians and my executive assistant Atticus, who I routinely threatened firing for small errors, enjoyed putting out her Newport Slims on my breasts.

Yes, while our typist snapped a Victor rat-trap on my left nipple."

Madge sighed as she continued the story.

"Asher Milo, who runs our chief competitor, Duchamp, Bischofberg & Basquiat was there, as was his lover, Silas, and they had a contest with our employees as to who could fill my mouth with the most urine..."

At the end of the evening, after everyone on staff had been alternately fellated and licked by Madge, the bruised and battered sixty-ish boss was chained to the cellar floor, without being allowed to cum.

And, of course, Rebi had announced to the group that Madge would be belted and not allowed to cum until the next "party" and ONLY if the subordinates voted that she'd been a "Good girl"...

And Rebi suggested that Madge suck off as many employees as possible when they came into her private office, just to get them in generous moods when the party came again!

Madge had worried this might be the end of her business-her staff might blackmail her, or just not do their work well, as they had lost respect for her.

"But I was wrong, Thumbs." Madge said breezily.

"The whole party experience made my employees see me as human, and they were friendly, and endured my occasional rages, in return for more cash bonuses, and a monthly "Give it to the boss" party...

Which many, including me, look very much forward to! I owe Rebi so much."

I was a bit in shock...Rebi apparently had set these parties as twelve weeks apart for the first one, and then every eight weeks after that...continuously.

And Rebi and Madge had shared a house for nearly eight years, six of which had been under this chaste "arrangement"...

And the older woman really looked forward to being allowed to very rarely (employees can be capricious) being allowed to frig herself in front of the staffers...

If Rebi was this hard on Madge, what the hell would she do to me?

The chap who was to be my potential roommate, Pruitt Keilson III was a little jealous, I think.

A West Point grad, Pruitt fought in the Gulf and Kosovo with the 78th Airborne, brigade commander, that sort of thing, Pru was now president of the New Piedmont Burglar Alarm Emporium.

"It's just a little much." he groused to me.

"I've been paying Rebi twenty grand a month for room, board, and uh, services...why do I need a roommate?"

The whole idea was kind of baffling to me. Since...I would be in a bed, and Pru spent every night in an enormous baby crib...and at least once a month, Pruitt's cousin Purdue, who had been cut out of the family inheritance 'cos he was a homosexual punk rocker, would enter the room at midnight and jerk off into Pruitt's mouth...

Still, I'd do anything to get closer to Rebecca!

It's funny-you never know who else is a closet submissive. My best buddy Mason and I grew up together-

Kicking little girls in the mud in kindergarten, getting stoned in his backyard tree house in seventh grade, and pledging the Alpha Deltas at New Piedmont Central College.

Since high school, Mason and I and our pals Teddy and Walden had had a Friday night poker game, now going on nearly thirty years, and it was sacrosanct. Nothing ever disturbed it.

Mason was a tough guy, all man, we admired him so...quarterback, point guard, all the teams, and a spectacular card shark.

But one night we went to his house to play, and we found a girl at our table...my russet haired Rebecca!

Of course I had no idea who she was, and she merely explained that Mason was in the kitchen, and he'd be bringing out the chips and beer, and she'd start out playing with us.

And we'd never had a girl play with us before.

Nine divorces between us, and many weeping waitresses, but the Moody Boys, as we called ourselves (the fifth Moody, "Bink" Behrens, had moved to Colorado in '05) were inseparable.

But we found out that Rebi was really, really good at poker. (She's also a whiz at miniature golf, but that's another letter).

After her third pot-winning hand, a royal flush with an ace, a king, a queen a jack and a ten all in the same suit, we became somewhat restive.

Teddy actually burst into tears and threw in his cards, as he'd just lost the Rolex he'd gotten for graduation from Dartmouth.

"Where's Mason?" I complained loudly. I was wondering if he was fucking this old broad, or what the hell was going on. She wasn't hard on the eyes, but I had now lost nearly one hundred twenty-five dollars...

And then he came out...

Carrying a tray and wearing a garter belt, stockings and high heels.

Not even a French maid's uniform as your readers might expect. My best pal, a muscle-bound but yet highly intellectual osteopath...

Rich, smart, and quite the lady-killer...

But what the fuck was this?

The Van Dyke he'd we'd envied since he was nineteen was all shaved off. Mason had more Revlon on him than a five-dollar trollop.

Eye shadow, foundation...ugh.

And clothespins on his nipples?

"I-I can't do it, Miss Rebi." Mason sobbed, as he stood by the kitchen door, holding the tray and shaking.

"Mason, baby." Rebecca smiled as she lay down her cards. "This is your fantasy. Your humiliation fantasy. To expose yourself as a naughty little slut in front of your macho buddies. You're paying me five hundred bucks for the evening, not to mention what I'm shoveling in from these pathetic compulsive gamblers."

Rebi picked up the Rolex and looked at it critically. "You say your uncle gave you this? It's a weak imitation. You can have it back."

Indeed, as one looked at the watch carefully, it actually said "ROLEZ" but Teddy had always been somewhat myopic.

She tossed it to Teddy, and he caught it nervously, silently cursing his cheapo father's name.

Walden gave Mason the fish-eye. "What the hell's wrong with you, dude? Put some clothes on. What are you, RuPaul?"

Walden had always been jealous of Mason because the latter had edged him out as captain of the basketball team back in high school, and had also been the head of Mathletes...

And of course had had a better car, as Mason's dad owned New Piedmont Lexus Associates.

I was in shock. Because of course I had been going to dommes since my sophomore year of college, and had been subscribing to BDSM magazines from a post office box for years, until the computer revolution hit...

And the porn sites had given me all the fun I needed...

But I'd always wanted a hardcore Mistress.

I couldn't believe Mason was the same sort of weirdo I was...

And I was thinking at the time that Mason couldn't believe he was doing this in front of his old buds.

Turning and stumbling on his left heel, Mason (who I noticed was wearing bright red lipstick) said "I, I just can't do it, Rebi. I can't...it's too embarrassing."

And then Rebecca got up and walked over to Mason, the three of us watching her cleavage jiggle in her tight print dress...so low cut!

"Now Mason, you don't want me to go and get the cane, do you honey?" We heard this soothing purr and shook our heads.

Teddy, a bit of an airhead looked bewildered, and Walden looked a bit triumphant. "I always knew he was a goddamn wuss" Wally whispered.

"And besides" Rebi gently dragged Mason over to the table by the ear.

"You know you're due to get your cage off this Friday, right?"

Mason nodded his head.

"Remember? You were due to get it off back in May, but then you lost your temper when we were in the car, and I had to move your date to September 5th.

Oh, but then we both agreed that it would be better to wait till November, on your birthday-to make it more special."

"Th-that was your idea, Miss Rebecca." snuffled Mason.

"I-I had hoped to get one in November and then another jerk-off session on my birthday...

In early December, and then one on Christmas-"

"That's right my little greedums, and so when you suggested this, I remember deciding you shouldn't get any orgasm at all until Valentine's Day.

Which is next Friday...should I move your date till June? That'll be a year, babe."

"Actually eighteen months." Mason began crying again, as he stood there on his heels. We hadn't seen him cry since we were kids. And as I looked down, there was the chastity cage. With his dick bulging in it!

"That's right...you had your orgasm last January, and then you were going to get one in May, and then we've moved it for thirteen months...

Don't worry about humiliating yourself any more, Mason.

After tonight, these poker games will be a thing of the past, first because your pals won't want to hang out with you any more, and secondly, because I've won all their money for quite a while."

She was right. Never trust a woman who brings a credit-card charging machine to the table...

"Why don't you show the boys your cock-sucking skills after you serve the beer and the chips, Mason, honey?"