Letter From Scranton

I had taken fairly heavy pain but I was a bit of a crybaby.

"I can't abide a screamer." Edyn said as she glanced at our waiter, who refilled our wine glasses.

"So Terence" Edi said, reading the man's name tag, "Tell me does my date look like a weeping sissy to you? "

The waiter, a tall African-American snickered and then looked at my blushing face anxiously. He didn't want to be stiffed on the tip, and clearly I was paying.

"Hubie, give Terrence a twenty for his honesty."

That's how our first date went.

There were a few more chaste dates, and finally I got Edyn home, and she brought up the possibility of my crying again.

"Portsie told me you screeched like a ballerina when she put rat-traps on your nipples, and that you can't take much more than a paddling without becoming a squirming mess."

"It's been really difficult, Edyn" I confessed as I brought her an Amstel Light. "I want to be a tougher slave but..."

"I bet you were a hall monitor in school, and tattled on people."

"There was too much bumping and laughing when the students were changing classes." I said huffily.

"Also I was mad when the guys picked me last when we were picking teams...and I was kicked off the debate team for being too self-righteous."

"You poor, poor thing." Edyn murmured, but you could tell she was trying not to laugh.

I told her how the first time I got drunk, my so called friends took off my clothes and drew epithets on me and put nail polish on me and showed me naked, with shaved off eyebrows to the girls on the drill team...

And quite a few other stories. I got the impression, though that she was unimpressed by my youthful trauma.

Edyn leaned towards me and I was overcome by the fragrance, a la Chanel of "Chance El Fraiche" (if it's any of the readers business, I knew this because I splashed a bit on when I went out in drag some nights.)

"Do you trust me?"Edyn's pink tongue peeped out of her full lips.

"Always" I said nervously.

We went into my bedroom (The master bedroom and I haven't been allowed to sleep in it since Edyn moved in)

Edyn had me strip naked and lie on the bed (twice now she'd not undressed and I was naked before her.) on my back.

Edyn jacked my legs over my head and tied my right wrist to my left ankle and vice versa, using my very expensive neckties.

I suppose I looked terrified because Edyn sat down and began gently rubbing my nude butt and snaked her hand in between my legs.

Tonight Edyn was clad in a turtleneck and leather shorts, she was the sort of girl I dreamed about but never had the guts to approach...

As Edi absently stroked my penis between my upraised legs, she talked about pain "Volney never could take much pain, but I worked on him. Denying his orgasm for months seemed to make him more pliable."

Her burgundy nails tickled the underside of my lengthening shaft.

"And Volney's need got to the point that he became inured to the pain, and eventually could take so much more. And then he could suck cocks for me and do all sorts of other things, but pain tolerance came first!"

She paused as her forefinger grazed my anus. "It was so good for Vol to become a passive pain slut.

His behavior was so amazing that when his son, Placidus brought home the girl he was going to marry, a sweet redhead called Hyacinth, the couple took our philosophy quite seriously.

"Really?" I couldn't believe that they'd exposed their ways to their adult children.

"Hyacinth told us that Plass was arrogant and demanding, and I counseled them, and they took up a femdom lifestyle, and after Volney and I split, he went to live with them.

She laughed. "There's a little room in the upstairs quadrant of Plass's house that's called the Seclusion area, and whenever Plass or Vol acts up, Hyacinth just escorts them up there for quick bullwhip action."

Thinking about this got Edi excited and she rubbed my dick faster.

I couldn't get over how sexy Edyn was.

When I was a weedy honor students I'd see girls like Edyn covered in tattoos sometimes and piercings, flirting with the tough guys from Shop class.

There was a demon witch from those days...she was called Casimir, who I'd been especially attracted to and I'd let her look over my shoulder when we were in exams.

No gratitude, though.

In fact, Cassi would yell, "What you lookin' at, queer?" and once she'd asked me to meet her in the bushes outside the Prom.

Then Cassi's boyfriend a 25 year old ex-con had pantsed me and they'd taken a video, sending it all over the school. I was 19 then, and very, very traumatized.

But here Edyn was, her lips glossy with pink gloss, smiling tenderly as she rubbed my bare ass cheeks and then my penis with those sharp French nails.

As I went into a daze, she flicked the tip of my bulbous organ, and I squealed, and she laughed.

"Hubie it really will be all right. I am going to teach you to take your discipline lik a man."

She laughed. "My first husband, Ryleigh's dad was an absolute stud. His name was Euclid, and he took me around his house and showed me his belts and whips and told me that he wanted me to dominate him."

She laughed musically.

"I tied him down and was rubbing his cock and then asked if he wanted to cum, and Euclid said that was my decision. And so I ordered him to lose his hard-on, and after I'd whacked his dick a few times, Euclid did."

"You sound like you learned fast" I ventured. Edyn ran her fingers through a tuft of my pubic hair.

"Yup, and I wasn't even horrified when he suggested he only be allowed to cum around the time I menstruated, after he'd sucked a few tampons dry."

"But we have to teach you to be tough, not a crybaby. I don't suppose you have any punishment implements in the house."

Edyn looked over at my discarded clothes. "Here's a belt but do you have one that's thicker than this?" She dimpled at me.

I was so freaked out, tied as I was, wrists to ankles.

But I was so damned turned on!

And I told Edi my dad's old leather belt was in the closet, the one I kept for sentimental reasons.

"You told me your dad had a horse farm. Did he have a woodshed by chance" Edi asked giggling, as she went to search for the strap in question.

I gulped pushing back the memories. "We had poultry, too." That wasn't an answer, but it was a response.

Edyn brought my father's old thick belt out, with the big iron cross buckle. She was standing in front of my bound body.

Just looking up at her, I watched Edyn's hips tilt and those amazing legs, coming out of the shorts, all the way down to her powder blue stilettos.

Edyn sat down next to me again, reaching between my raised legs, she stroked and tickled my member until it was standing stiff and was glistening with precum.

I realized part of this was so I would stop trembling. Between the arousal and the fear, I was a mess!

"I want you to lean into the pain. Make it a part of you, you don't really have to resist it, Hubie." She rubbed faster, and then let go just as I was about to spurt!

Edyn pulled back and watched, laughing as I humped the air in desperation. When I calmed down, she resumed her stroke with one hand, while fingering Dad's belt with the other.

"My first husband, Euclid grew up in a fundamentalist family. When Euclid and his brother were watching TV with their father, and a hot girl came on, Euclid's dad would go. "I don't know about you boys, but I'm feeling tempted" and he'd leave the room.

Edyn tugged the crown of my cock as it empurpled once more. "When Euclid's dad died, Euclid came home to look after his effects, and found a chastity belt."

Edyn stimulated the pulsing vein on the underside of my wiener until it got very blue.

"He showed it to his mother who smiled, and Euclid realized that his dad was a chastity slave to Mom...is that where he got it? Who knows?"

Edyn attempted to stick an acrylic nail into my urethra, and I shrieked.

"Euclid has a twin sister, Egypt, and he had Egypt put him in Daddy's old chastity belt and keep him studying hard all the way through university, which really should be your ultimate girl banging time, but that's what he was about."

I was so excited, thinking of that, being around all that pussy and be locked up...worse than any pledging hazing my fraternity put me thru!

Edyn tickled my testicles again and I gasped. "The first night I was in Euclid's spacious house, he showed me his own punishment room, much like the one I told you about before."

Edyn let her fingers do the walking up my foreskin and then pinched it cruelly with her sharp nails and I moaned.

"Unlike the luxury of the rest of Euclid's house, as he was an heir to a heating oil fortune, the punishment room was soundproofed and bereft of anything except a blanket and a meager pillow."

Edyn drummed her nails on my glans and licked her lips at me as if she might give me good head later, though I doubt this was true.

"Since I have a private income" Euclid had said--that's how rich people talk "I am at home much of the time, and my last dominant girlfriend kept me in this room, and I had to earn my way out with chores and treats, and I think you should do the same thing with me, Edyn."

Edyn smiled reminiscently. "I remember I used to put duct tape all over Euc's body and rip it off to clear up all the body hair. "

She put her tongue between her teeth and snickered as she pulled out a few of my pubes.

"But when I married Volney, and decided he needed deforestation, I took him to a depilation place, which was probably less painful...But my first submissive, Euclid, was such a tough guy."

Edi poured some lotion on my penis, now resembling an MX missile, and wrapped her fingers loosely around it...she didn't go up and down, she just let her fingers tremble, and was that a sensation.

"I was this love struck girl of 18 or 19, and I said 'Don't you want to enjoy your beautiful house, Euclid?" And he of course smiled and shook his head. "I only should enjoy it when you allow it, Edyn."

There was a pause. "Now I'm going to use the belt on you, honey. Try to stay quiet, and if you can take ten with the belt, I will stroke your pee-pee some more."

I felt sort of infantilized by the "pee pee" appellation, but of course it excited me more.

Edyn smiled. "Oh, it's getting so excited. It's not much use for lovemaking, God it's tiny, but if I lead you by your cock, I can make you an efficient pain slut.

Edyn took a pillow from the head of the bed and shifted it right under my butt, which was of course, jutted up.

It felt so cool against my raised hips, the pillow, and here was my beautiful girl, Edyn...I tried not to think of the pain to come.

Edyn got up and looped the belt. "Ready, hon?""

"Y-yes, Edyn."

Edyn swung the belt hard. The first whack was a well-aimed cut, right at the sensitive area where buttocks and thighs meet, and then she went to work.

I gasped and bit my lower lip. Edi really had one helluva tennis swing. My eyes teared up, but I made no sounds.

She watched my lower lip trembling and a lone tear rolling down my chubby cheek and stopped. "You poor little thing, look at you trying to hold back the sobbing."

She smiled warmly. "It is so sad when I whip a man and he cries like a little girl. But of course most of you men are paper tigers...But you can be a big man if you want to, you just proved that!"

Edyn sat down again and reached through my suspended legs and began playfully massaging my rising dong. It had become quite flaccid during the thrashing...

But hearing her tease me about being a crybaby had excited me a little. What was wrong with me? Most men want to be macho, don't they?

"Now, cutie (At the "cutie" Edyn let go of my cock and moved up on the bed so she was sitting near my head) "Your Edi wants to hit you again!"

I hadn't quite gotten over the previous lashes, and I think a welt was rising, but I kept quiet.

"If you can stay quiet for 20 more licks with this little belt--"

LITTLE! Was she kidding?

"--I'll take off this turtleneck you've been gaping at, this pink, fuzzy top for you. It's much too snug anyway."

As Edyn said "Anyway" she wriggled slightly and her breasts bounced.

I gasped and she leaned down and gave me a big kiss. We had been dating for 2 weeks now, five dates in all, and this was the first time I'd go0tten more than a perfunctory peck on the cheek.

"Are you ready for a little more challenge?"

I nodded hesitantly, and Edyn rose and went back to the foot of the bed and gave me twenty more. I almost squealed at the ninth and then again at the fifteenth and eighteenth, but I stayed silent.

"Aaw" Edyn said. She looked at my butt sympathetically.

"It is singed, your poor rear, isn't it?" Edyn pulled her sweater off and there were her tits encased in a little turquoise jogging bra.

Edi's boobs were big but perky, and her cleavage was something else.

Edyn lay down next to me, trussed as I was. I am short and she's tall, so she was able to lean down and play with my cock while looking me face to face and yes, kissing me.

Edyn really knows how to suck face, covering my lips with long licks of her tongue and then giving me hickeys on my neck and soon my face was covered in her smeared hot pink gloss.

And Edi's fingers had dexterously massaged my dick until I was gasping.

"Now if you want to make another deal, for another 20 licks and ten minutes of strokin' and smooches, plus I remove my bra and a lucky boy gets to suck my long pink nipples...how's that?"

I got very excited and Edyn too k her time moving that glorious, cleavage away from me, and then she got up.

Edyn bumped and grinded her way to the foot of my bed again.

I am afraid to admit Edyn 's next 20 whacks with the belt--yes, it left me screaming and sobbing after eight, and I begged her to stop after fourteen. I realized the previous hellish spanking had been Edi going easy.

It was like a card sharp that let you win for a bit and then stole all your money!

Edi stepped back coldly after I became a weeping, quivering mess. "You couldn't even finish, what a little crybaby faggot. I know what Portsie was talking about now."

Edi threw down the belt and pulled on her cute little sweater.

"Why should I let you see me with no clothes on? You don't deserve to see a woman naked, you're just a wimpy little freak." She began imitating me cruelly, the way I sobbed....

"Puh-please, Edi." I said tearfully. "Jus-just give me another chance."

Edi looked sad now. "I don't think so, honey." she said regretfully. "Just go back for your pitiful pseudo sessions with Portsie."

"Oh no, please." I began crying in earnest. I couldn't lose her! As she taunted me, it excited me so...I was so humiliated.

And Edyn was so beautiful. I was quite aroused that I couldn't take a whipping and was just a little sissy.

"I'll do anything, Whip me some more. I'll go down on your boyfriends, anything you want, Edyn. I do dream of kissing your tits."

Edyn smiled. "I'll see you next week for another pain test. Do you realize that if you'd held out I would have gradually stripped naked and we could have made tender love?"

I nodded, thinking of how I wanted to nurse her glorious breasts!

"We'll do it next week, I promise, I'll have recovered by then, Edyn."

"On one condition that you don't jerk off during this week, thinking about my kisses. I want you all tense next week." Edi looked severe.

Still, I could surmise she was trying to restrain a giggle.

"I promise, Edyn."

Edi's lovely eyes rose to the ceiling. "Yeah, I can see how honorable that would be."

Edyn went through her miniscule handbag and retrieved what appeared to be a large thimble. It was about four inches long, and had a little loop on it, as if it were a tiny sand bucket.

Well, the loop looked like a ring in the side of the damn thing...and you can guess the rest. Edyn put the thimble thing over my dick.

My little peepster was about six inches erect, and was getting hard rapidly, but Edyn punched me neatly in the balls between my upraised legs, and I went limp.

The thimble thing had a lock and was apparently a horribly primitive, uncomfortable chastity device.

I had lost my father's chastity belt to Egypt, who had taken it to lock on her fiancée as soon as she married, my sister being no fool.

So I couldn't exactly protest here, and tell Edi to give me a more comfortable crotch prison, right?

After the thimble was affixed, Edyn untied the ties and told me she wasn't angry anymore. I was so pleased that my legs were no longer suspended in the air and that I could move my arms and legs properly.

Edyn lay down next to me on the bed and we necked like teenagers for an hour and a half until my dick was pressing hard against the thimble.

Twice I tried to touch Edyn's bosom and take her shirt off, but she slapped me and told me I would have to earn that right next week by taking the flogging with no bitching or moaning.

Otherwise, she was completely friendly.

"Why don't we go tomorrow to the fair you were telling me about?"

There was a state fair back in Plainfield, not as good as the Wilkes-Barre State Fair here in Scranton, but a fun place to take a girl to.

And I was excited for that! Edyn suggested we go to sleep and fully dressed, she pulled my horny body, naked except for the thimble in a hug against her...and then we spooned all night.

And Edyn stayed with me for the next week....She never undressed in front of me, but she took showers privately and then pranced about in a towel...and we had such fun...

One day she dropped by my office and asked Maurieta, my assistant, if I'd been taking shorter bathroom breaks. Maurieta said yes, and had wondered if I had found a urologist (I'd told her I had Bashful Bladder Syndrome AND Spastic Bowel Disorder to excuse my jack off times in my private executive washroom.)

I am afraid Edi told Mauri of the true nature of why I didn't spend as much time in the loo, and the ladies laughed in my office as I stood there, burning with shame.

But that night Edyn made it up to me...she dressed only in a bikini, and we showered together, she unlocked the thimble and washed my penis and balls slowly before locking me back up again.

After the shower, Edi had asked me to shave and put lotion on her legs and to give her a long deep tissue massage while she reclined in her bikini..

After this, Edyn returned the favor, giving me a 2 hour rubdown, rubbing everywhere but under the thimble, even right around it...

And then she turned TV time into some kind of teasing frenzy!

She sat in my lap while we watched "Ozark"...and seeing televised people getting murdered and being simultaneously erect is a strange experience, even with a pretty girl writhing shamelessly in your lap, and kissing your neck!

Then Edi had toyed with my dick for a while, using a half tube of Astroglide, before punching me in the balls and locking me back in the thimble!

By the time Saturday arrived, I was a horny, nervous wreck. I was ready to be flayed alive, if I got Edyn's clothes off!

We went to her house for a change, and I was impressed by her scented fuchsia tinted bedroom.

Edyn had tied her hair back in a cruelly plaited French braid and she looked at me severely. But her skin was creamy and her smile was elusively showing up now and then.

"Hubie we're going to do this again and I hope you will not squeal like a pig." Edi snickered. "I had to punish my ex for being such a screamer by making him wear a pink jumper and Mary Janes, and having him play hopscotch in the driveway. His big, strong friends loved that."

I shuddered a bit, but was tremendously aroused as well. I was astoundingly horny at the idea of being humiliated in front of my pals and then just being a constant sissy maidservant to this beautiful girl