Letter from Mount Chapel

I was trying hard not to giggle at the woebegone look on his face. "I want to give you a good time here, but you are too ready to cum, and you want to make a mess all over my cute little leopard skin frock."

I was looking at him severely. "That's why the paddle's here. You need a distraction."

I took Oscy by the elbow and bent him over my legs. Of course his cock felt a great sensation, after months in that hot metal prison, he was pressed against my cool thighs.

I lifted the paddle and brought it down as hard as I could against Oscy's bare bottom.

It was quite a good paddle, Oscy had picked it out himself, he told me once that two or three previous girls had used it on him before I had, but of course I was the best.

After the first whack, Oscy squealed and I swung again about four times.

Oscy was in true agony, and trying desperately to get off my lap. Still, he hadn't asked for mercy, which was kind of our safe word.

I held Oscy by his cuffed wrists, and after giving him about fifteen more swats I felt his cock getting small again.

Now I pulled Oscy off my lap and he was sobbing a bit, but I could tell his penis was starting to harden again. The humiliation of a clothed, gorgeous woman punishing his bare ass...

If you were a masochist, as poor Oscy was, this was a great thrill.

Now I was all sweet again, all rainbows and unicorns. I leaned over and kissed away Oscy's tears. My lipstick was leaving all these marks on his face, but I could tell he enjoyed it.

"Bet you wish I was sucking your cock with these big lips, don't you, Oscy?"

He moaned again, and his cock was bulging up again in my soothing hand.

"You are so luscious, Kelsea." Oscy moaned this... "But still, it's been so long since I got to cum, I thought this would be a reward time for me, and all I got was a spanking."

"Poor baby. That was just to refocus you so I could play with your pretty pee-pee again.

I looked down at Oscy's cock, which I had been absent-mindedly diddling and twiddling.

"You are getting roaring hard again, Oscy. I am so amazed by this swelling progress of yours. How it must have been heel you being all locked up the poor penis."

Oscy nodded wearily.

My fingers tickled the sensitive spot under his cock head., the part known as the frenulum. I leaned over and kissed Oscy again.

"Was it hard watching Craig and I making out and getting it on?" I paused, smiling.

Oscy nodded sadly.

"I bet it was difficult when Craig was sucking on my pretty nipples, which you've really never been able to touch with your mouth. You have to understand..."

"I know, I'm a wimp. Wimps are a turn-off" he said looking terribly sad.

But my God, his dick was still stiffening. The realization that he was just a faggy little critter drove him insane.

"I felt that when I licked you out after you'd fucked Craig, I was just getting Craig's after-party, his cast-offs, you know?"

I found this offensive, and I slapped Oscy's face really hard. "What kind of thing is that to say? I should lock you back up right now."

As Oscy protested, babbling and apologizing, I dragged him back across my lap and gave him fifty more with the paddle.

When Oscy rose again, he was sobbing torrents but his penis was as hard as a Louisville Slugger, the metal kind.

"I'm so sorry, Kelsea. I wasn't thinking." Oscy moaned. "It was just so hard being locked up all the time, being unable to sleep because I was so horny. And my dick would get stiff in the middle of the night, I'm still a young guy."

He sighed. "And when I'm out, there are all the pretty girls, secretaries, college chicks sashaying by, and then I'd come home to you and I love giving you a rubdown but it is frustrating. I am a man, you know."

"Of course you are, my prince." I said, and I squirted some lube into my palm and began rubbing and tickling his penis. I pushed his face into my cleavage with my other hand ...

Now Oscy's cock was nearly the size of a beer can in my hand.

I had always told Oscy that his penis wasn't very big, but it actually was a fairly impressive size. It might have even been bigger than Craig's.

But I had to emphasize Oscy's comparative wussiness, and often I had made him wear garter belts and stockings and high heels around the house, especially after I'd gotten him to sell the boat and was trying to make him understand he wasn't a manly he-guy type.

Now I massaged his cock a little faster. "Are you sure you need to cum today like a big boy, Oscy?" I asked. "I can do your anal prostate mimimizer so the pressure will be off, and I can just lock you back up."

"Oh please no-"

"Come on, Oscy." I grinned. "Let's do a makeover instead, we can work on your foundation and some nice blusher and lip gloss, and paint each other's nails. I could just lock you up and you can forget about all this orgasm nonsense."

Oscy began weeping softly.

I was inwardly enjoying this torture immensely. I could tell that Oscy was starting to fall apart, though he was hornier than ever.

"Wouldn't you like to serve me because you are devoted, not because you want an orgasm? Why do you need any more reward than that of serving your Mistress Kelsea?"

The poor thing's eyes were filled with tears. "Buh-but you said if we finished the remodeling-and I worked so hard."

"Oh, no, are you showing me attitude? I am so disappointed by you, honey, after all the hard work you did on the kitchen, showing your obedience...

Carrying planks and painting and stuff, going to the granite store. Those nice countertops you put in, yes I am so pleased, but now you want to order me around, to give you an orgasm like I'm your whore? Is this what needing an orgasm makes you? A monster?"

I stopped rubbing him for a moment. "I don't like that at all. Maybe I should lock you back up. Maybe you should be fixed, like a dog."

But then I began stroking him again, and tittering as he panted and cried at the same time.

"K-Kelsea, I have tried so hard to be a good boy. Please let me have my orgasmic reward. It won't take long. I -I didn't mean to order you around."

"Well" I pretended to consider. "I can't stand your bossy behavior right now, and of course I know this will happen again. You know when your NEXT birthday orgasm happens."

"That's a long time away to wait for another one. Couldn't I get one a couple weeks after I have this one?"

"How about I let you cum now, but you can't cum again till-say-Christmas. No! Valentine's Day! A day of love. You always deluge me with presents on V-Day and I can let you jerk off then, and it will be such a thrill 'cos you will wait so long."

"B-but Kelsea it's only July now. That will be so many months to wait for the next one."

"My God, you're going to get one today, right? And you're already worried about the next one?"

"It's just-" Oscy hung his head. It didn't occur to him that he could just get some bolt cutters and take the thing off, or throw me out of his house. He'd really lost any will of his own, it seemed.

"I mean, look at it this way, Oscy. You'll have the memory of this awesome cum you'll be getting now." I rubbed his dick faster and his legs began to collide and grow weak.

"Oh, I want to cum now so badly, Kelsea."

"I want you to start calling me Miss Crimmins. You are too familiar."

I rubbed and swirled my pretty nails over his bulging glans.

"That's condition one for this orgasm. If I give you an orgasm, you have to not p ester me for the next one, even mentioning removing the belt until Valentine's Day."

Oscy's eyes began tearing up again although he had been staring at my cleavage greedily.

"Oh, I want to cum so badly now, Kelsea."

I slapped him.

"I mean, Miss Crimmins."

I stood up and led Oscy to the bedroom by his cock. I lay Oscy on the bed and sat on his legs, smiling at him as he gaped up at me.

I began stroking and pulling Oscy's dork faster and faster.

"I can stop playing with your dick and we can table this discussion if you are unsure of my demands."

Oscy's mouth opened wide, and I wanted to spit in it.

"I didn't know how badly you were going to behave this afternoon, telling me I'm Craig's leftovers and all that other crap."

I began slowly stroking again, and Oscy's cock looked as if it might explode, although now it was waving about. I watched him sobbing and apologizing.

"O-okay Miss Crimmins, I'll do whatever it takes. N-no more orgasms till Valentine's Day."

"Excellent!" I got off Oscy's legs and pulled his legs over his head. I uncuffed his hands and waved. "Jack off all you like, baby."

"We-I thought we might make love-"

"I think if you don't masturbate quickly, I am going to lock you up for the next three years."

So Oscy jerked off and when he was about to spurt, with his dick over his mouth, I twisted his right nipple, and his mouth opened and he shot neatly down his throat.

"Now swallow all that nasty stuff, Oscy. Yes, right now." I held Oscy's chin with a firm grip and he swallowed it all, reluctantly.

And then I locked Oscy back up, quickly and efficiently.

The next few months were kind of hard on Oscy. I realized I loved the guy too much to have him call me "Miss Crimmins" so I let that one go.

But I saw no reason to change his chastity sentence...and why not have him do some more serious work around the house? And, for that matter, why not sign the house over to me?

This might take a bit of effort, especially since Oscy's parents held the note. They already didn't like me much, thought I was a gold-digging slut, and maybe I was.

Oscy's dad, Oscar Senior, did kind of watch my ass a bit, so I figured the best thing to do would be to get Senior into bed. We began fucking madly, and since Oscy was still locked up, to keep him from resenting his pop, I had him work harder on the house, fixing the roof, installing a sump pump in the cellar and closing off the screened porch.

Oscy's dad was consumed by my pretty figure, and I realized that he would do almost anything for more time with his hands on it. My Auntie Ingrid suggested that since Oscy's folks didn't fuck or even see each other naked (separate bedrooms) the wisest thing to do would be to put Senior in chastity as well.

I told Senior that this would intensify his feelings for me, if he was locked up, and implied that I would be celibate also, between trysts, but that was ridiculous, of course.

Not only was I fucking every low-life I m et but I was often bringing them home and making poor Oscy service their cocks before and after the sex act.

Finally at around Valentine's Day, I had had Senior denied for three months and Junior (Oscy) locked for nearly even, and I was able to get both their signatures on the real estate transfer before I allowed father and son to suck each other off.

Oscy's mother was insane with rage that her husband had become such a sap for this bimbo of her son's, who wasn't even technically a daughter-in-law.

Today my life seems to be thriving. I haven't had to work bagging groceries in years, and I have Oscy and his dad hanging out together in my house. I put them both in full drag and teach them to walk with proper posture, balancing books on their heads.

Learning to walk like a lady is so important!

Senior and Junior are very competitive and it doesn't even seem to bother them that this white-trash redneck girl has them so peculiarly attired.

Oscy's mother finally split, and Oscy's dad is living in the house with my Auntie Ingrid, and it looks like they may wed soon.

Should I marry Oscy? He has proposed to me several times. It's hard for him to impress me because I keep him either in a diaper or naked except for the chastity device.

Unless he leaves the yard, he is kept naked I have Oscy mow the lawn in his chastity belt, and then he gets on his knees to clip around the edges. I check his work, and when I spot a stray blade of grass, I go to town on Oscy's butt, and it has made him a better landscaper.

Sometimes I go away for the weekend with my new boyfriend, and Auntie Ingrid brings her latest stud and we lock Oscy and his dad back to back in the garage and they tell us this forced bonding leads to great discussions. Oscy's dad says that I am the only real woman he has ever known.

That seems a little ridiculous, doesn't it?

The other night I had Oscy tied to the bed, spread eagled of course. I was toying with his cock which has now been denied for seventy-three days.

"Kelsea, I can't believe it." Oscy said as I stroked his member lazily.

"Since you moved in, I quit smoking and I don't drink much anymore, and I have lost thirty pounds. Kelsea, I owe you everything."

"Well, I aim to please." I replied modestly as I pulled his foreskin over his glans and back down again in an enticing way. "I'm very proud of you too, Oscy."

"And my Dad is thinner and happier, and he told me he is really sweet on your Aunt, though if he marries then he'll be both your uncle and your father-in-law, that is, if you marry me...it might happen, right?"

"Maybe."

"Your Auntie Ingrid says she stripped and spanked Dad in front of his V.F.W. buddies, and he will no longer be drinking with them except for one or two..."

Yes, I'd heard, a couple of them want also to be Auntie Ingrid's submissives...it's a weird life, Shoeblossom!

Best,

Kelsea.

Dear Kelsea-marry the poor guy, he may not make it without you!

Best, Shoeblossom