Letter from Courtfield Common

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How did his tough friend become a masochist sissy?
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Dear Shoeblossom

So the strangest thing happened to me recently. I am kind of a nerd, and I fix the bikes for friends of mine in a motorcycle club and I ride one myself, though possibly not as fast as they do!

Recently I found out that one of my very tough, muscular friends had another interest in common with me...Scruffy was in chastity, and had a long-distance key holder!

"Seriously, Scruff?" I asked in amazement. "But don't you miss getting laid? All these girls really like you. I know at least four..."

"Enzo, I got to tell you, man, Miss Tartlett is the bomb. I'd rather see her three times a year to get my rocks off, than fuck any of these dumb bitches."

True, I fantasize about chastity sometimes, but I'm switchable, and I've had some submissive girlfriends. Although when I fantasize, I don't really want to do the real thing and be locked in a belt, but I can really give a thrashing!

I told Scruffy all this. He was quite interested, his big, bronzed face grinning.

"Yeah, well, I really will do anything that Tarti wants me to" He showed me some pictures of his key holder. "Remember how everyone bitched and moaned when I shaved off my handlebar moustache?"

"Yeah, I thought you loved that moustache."

"I did, but Tartlett ordered me to, as a sign of devotion, and Enzo, I did it!" He paused. "What's a drag is, sometimes she wants me to punish myself, and it's mighty awkward, giving myself a paddling or an enema, you know what I mean?"

"You mean, actually self-spanking?" I tried to picture this, attempting to hit yourself on the butt with a paddle. "I've heard of people doing it, I think I've seen it on porn stuff before."

This of course was a difference between many kinksters and me. I was happier fantasizing about being spanked than actually being spanked-it hurt, and I was kind of a wuss.

On the other hand, I'd had girlfriends, usually big fat girls from OK Cupid who were true pain sluts and I had been happy, even gratified to hit them as hard as they liked.

I had told Scruffy about these experiences, being a dominant Master of sorts, me with my Coke-bottle glasses and skinny exterior, and he'd laughed.

One night I got a call, late from Scruffy. I work as a video editor for the nightly news in Courtfield Common, just local, and sometimes we work late. I was still at the station, and there went my cell.

"Enzo?" Scruffy's voice sounded a little anxious. "You there, man?"

"Oh, sure, what's going on, Scruff?" I thought Scruffy sounded a little weird and hoped he wasn't dong X again.

"I was telling Miss Tartlett, my key holder how weird and award it is to discipline myself?"

"Say again?"

"You know, to hit myself, I'm real clumsy at it."

"Yes, that's right, we talked about that, didn't we?"

I was so thankful no one could hear this conversation as I worked in the cutting room.

"Um yeah sure, Scruf, you have an interesting personal life-" Fuck this was getting weird.

"Well, Miss Tart had a-a suggestion, it's kind of a big favor to ask of you."

Oh, how the fuck have I gotten involved with this. A favor?

But I sat down carefully, and discarded my videotape footage of the Greater Courtfield Plum Blossom Festival.

"It's a little perverted, maybe, Enzo-"

I should have followed my sister's lead and become a born-again Christian.

"What do you need, Scruffy?"

"I know you're not gay or nothing-" Now Scruffy's voice was starting to sound a little strained.

"No, at all."

"But you are broad minded, right?"

This would be a doozie.

"I really should discuss this with you in person."

I took the cell phone from my ear and looked at it. Then, warily, I returned it to my ear. "Hey, tell me over the phone, big fella."

"Uh-"

"You can tell me anything, Scruf-over-the phone."

"Well Miss Tartlett suggested that I ask you if you would paddle me. She has sentenced me from her webcam to twenty with my Spencer paddle. The one with the holes?"

"Yeah, I was with you when you got it at the leather fair."

"Yeah. I would try to punish myself, but I can't seem to maneuver it."

Suddenly, I was intrigued. "Yeah, sure, that's cool. I'll be right over."

"I hate askin' you to do this, it's a little embarrassing."

"No, I'm broad minded. I get off in forty minutes."

"We could do it tomorrow, Enzo." Now he was backtracking.

Hey dude, if Ms. Tartlett said you need to be punishmed, that's what you need. Do you really think she wants you to put it off?"

I was grinning into the phone. "We can get it out of the way, and I can bring some brews and we can watch Stephen Colbert or the midnight Monster Truck show."

On the way to Scruffy's house I was all aflutter in my mind. I'm kind of a weedy little bastard, and occasionally I've gotten into hassles with bigger guys...

See, I have a big mouth for being such a little Italian, especially in sports bars?

And more than once Scruffy had to bail me out and kick the guy, or several guy's asses, which he could do, because he was tough and mean.

Yup, Scruf's a big, strong guy. A patched biker. Did a year with the Pagans. I wondered if he got mad in the middle of this thing, he might decide to take a poke at me.

It had happened before. I was whipping a stoner chick with a wooden dowel, or something, and she decided she didn't want to be in the scene anymore, and she punched me.

And like I said, I'm a big wimp, right?

So, I really hoped Scruf wouldn't do that, no reconsidering.

Also, was I a fag? Why was I hot to do this?

When I got to Scruffy's house, I knocked with some trepidation.

Scruffy let me in. Scruffy is at least a head taller than I am, nearly six foot five. He was grinning nervously.

"I have Miss Tartlett on the webcam now." Scruffy whispered, gently punching me on the shoulder.

It was now or never, I thought. But I remembered when I got out from under my Catholic mother's thumb, I had resolved to enjoy every minute of life and do whatever excited me and by George...

We went into Scruffy's living room. He had a fairly nice place, he'd recently upgraded from a mobile home after getting a good gig on an oil drilling boat.

Still, he never had a lot of spending cash and I was about to find out why.

"Okay, Miss Tartlett, this is my buddy Enzo." There was a Mac computer with a huge screen and on the screen was a cute girl, about twenty-eight with swirling hair in a pixie cut.

Miss Tartlett must have been some kind of punk rocker because her hair was blue, green, and purple and she had more piercings than...well, she would have killed a metal detector putting her pretty little metal engulfed face in it.

But she had a formidable figure and was wearing a leather bustier thing, and a leopard skin miniskirt.

Ms.Tartlett had her legs in these hot fishnet stockings, a little torn up, and her legs were crossed and she was sitting on a couch, I presume in her own living room.

"Hey there, Tiger." Miss Tartlett said. "You must be Enzo." She was actually smoking a corn cob pipe, like Popeye.

"Uh, how's it going, Miss Tartlett?" I smiled at the attractive freak show on the webcam. I'm always damned optimistic.

"Enzo, you can call me Tart. I am one, you know." She winked. "Scruffy has to call me Miss Tartlett, right, idiot-boy?"

"Yes ma'am." Scruf was staring at the floor.

"So you have some experience using a paddle, Enzo?" She was probably surprised such a geeky guy would be into this scene, but in this part of the country, often it was the best way a nerd could get some action with someone attractive...

After all, finding someone strange enough for whips and chains could be difficult.

I looked at Scruf doubtfully. He bit my cousin's Barbie doll head off and swallowed it on a dare in kindergarten...

A decade later, when Scruffy and I got six months with adult criminals in County lockup, it was Scruf who kept me from being corn-holed...

And look at him now...

But about the paddle.

"Yes, I've even used the big, long Spencer paddle Scruffy described."

On a zit-laden MS cripple called Imogene Dubrovkik who he'd met on OK Cupid, but whatever.

On the cam, Tartlett leaned back and casually pushed her tits together and smiled at me through the cam.

"I'm not as equipped." Tart said, smiling. "When Scruf visited me here in New Jersey I got great results with a two foot loop of cable wire. He danced when I swung that, the little pansy."

I just didn't think of my bulky friend, as a little pansy...but...

Tart paused on the camera to adjust her lipstick and then pointed. "Get naked, Scruffy."

Jesus, this was happening. Scruffy pulled off his Motley Crue shirt and undid his boots and then his jeans, and here my best friend was, standing his tighty whities, yes, right next to me.

Tartlett looked somewhat perturbed. "I said take off everything. C'mon, you cock-smoker."

"Maybe we could do it, get me spanked over my shorts?" Scruf paused. "I mean, if it was just you and me, Miss Tartlett..."

"Well you were just going to get twenty with the paddle. Now we're going to do twenty-five, just for your lovely attitude."

"Oh, please, Miss Tartlett!"

"You want me to have Enzo give you fifty, and have him watch while I have you do a full cosmetic makeover? Full Face?"

Tart snickered.

"We haven't done a makeup tutorial in a while, Scruffy. That or take your undies down. Not much Fruit in those Looms, anyway."

Jesus. a makeup tutorial. Now I understood why Scruf had shaved off his beloved moustache.

Beet red, Scruffy pulled his shorts off and there he was in his chastity belt, a little steel pouch covering his crotch.

And I noted with some satisfaction, now that Scruffy was naked, that he had a pot belly...

Without looking at me, Scruffy went to the mantle and came back with the long, wicked Spencer paddle.

And then he handed it to me!

It was about two feet long, like a fraternity paddle but not quite as wide, and had holes throughout.

I kind of fondled it, and then looked at Scruffy...

"Get over the table, you goddamned sissy." came Tartlett's perky tones from the computer. "Maybe Enzo should butt-fuck you, too. Hurry the fuck up."

Scruffy bent over the big table that we all used to play poker on Friday nights, and, with Miss Tartlett's verbal encouragement, I beat the shit out of him.

Little hostility there, Enzo?

Scruf's a tough guy, but after fourteen whacks he was sobbing.

I paused for a moment, viewing his blistered rear, but he sort of waved behind him with one hand, indicating it was all right to continue.

And, from the Mac, Miss Tartlett was emitting quite a bit of tinkling laughter.

When I completed the twenty-five whacks, Scruffy got up off the table and dropped to his knees and kissed my feet, which made me a little uncomfortable.

Then, he shuffled on all fours over to look up at the webcam.

"Here, Enzo, you like my tits? I saw you checkin' them out." Tart said.

"You wanna see them?"

Oh God, yes.

"Okay, put a blindfold on Scruffy, he's not allowed."

After all this time? I was staggered.

But Scruffy had a red bandanna ready, and was rolling it up.

Still, he argued with the webcam goddess.

"Please, couldn't I see your lovely breasts for just a minute, Miss Tartlett?"

I could see the metal pouch between Scruffy's legs bouncing.

"When he visited me the last time." Tart said to me, utterly ignoring Scruf. "I told Scruffy that he could look at my naked tits if he agreed to let me whip his dick with a thorny rose stem..."

My jaw dropped.

"But then after I really tore up his cock, I told Scruffy that I was lying, and he'd never get to see my candies. And he still can't. Put the blindfold on, now!"

Scruffy began sobbing while holding the bandanna in his hand.

"No titties for you, my little homo. Let's just give a show to the boy you got the punishment from."

"Think what a pathetic creature he is, Enzo. He can't cum until I visit soon, and he just endured a helluva whipping from you...what an idiot, right? A true masochist."

Scruffy handed me the blindfold and I wrapped it around his bleary eyes.

And her dulcet tones continued...

"Scruffy's a bad boy. We've been working together for almost a year, I think, since he began serving me, but I've never let him see me without clothes on."

She smiled. "He's not really mature enough."

Then this amazing girl undid her bustier slowly, and I stood, immobile, tempted to masturbate, but who knows, she might want me to shoot on poor Scruffy's face.

"It's fun watching me toy with my pretty nipples, isn't it?"

I nodded dumbly. She was exceptional. Rose colored nipples on nice little C bra tits.

Finally, it came to her.

"Why don't we do this? Guide Scruffy's head to your crotch, and let him suck your dick while I show you how I massage my tits with oil."

Before I could answer, Scruffy turned around blindly, and shuffled to where I was, and I coughed in astonishment as my pal, a two time loser from the state prison...who was a bouncer when still in middle school...

He groped for my zipper and pulled it down and fumbled and pulled out my cock!

"Now, while I play with my plumpies, you skull fuck Scruffy, Enzo. Grab his ears and slam it home."

I saw big, thick tears rolling from under the blindfold, but I guided my penis into his mouth.

She rubbed her tits and talked to me about how beautiful they were, and how her pitiful submissive Scruf would never, never get to touch them.

"Yes, I am playing with my big, soft tits that you'll never get to see, Scruffy. Remember how you had to suck my boyfriend while you were blindfolded and he was licking my tits? This is worse, isn't it?"

As this went on, Scruffy sobbed loudly around my cock, but I saw the steel pouch bouncing as he cowered on his knees.

"If I ever get to meet you on my next visit, Enzo, I'll let you suck these hard nipples while Scruffy can drool on a pacifier."

I paused, gasping.

"Scruffy made a really painful whip out of an old spring that used to be on my screen door? It's covered in leather and it can make him scream like a bitch. I'll bring it down and you can make him cry like a baby for its doll...

But he'll never, never get access to this beautiful body...or even see it nude."

Scruffy was blubbering and at the same time frustratedly stroking his steel pouch.

He was more turned on than I was, I think!

I came hard in Scruffy's mouth, and pulled out, and Tart pulled a big black T-shirt on and told Scruffy he could take the blindfold off.

I left, and shortly after this, I stopped riding with the guys...I went to a revival meeting that my sister encouraged me to attend, and I am thinking of going to Bible school to be a minister.

But Scruffy's number is blocked.

Yes, I think maybe my life will be better as a Pentecostal minister.

We'll have to see.

Best,

Enzo DeCecco

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