Letter from Mount Chapel

Dear Shoeblossom,

I got into the sweetest deal. I agreed to play femdom games with my geeky male roommate. He owns the house and was renting me one of the rooms, and like so many nerds, he has the hots for us tattooed, embroidered jeans types, I guess.

Oscar is the sweetest guy, you know the kind. Comes to try and ask you out when you're smoking in the schoolyard, and then you and your girlfriends beat him up and take his lunch money.

There are guys like Oscy all over the place, at the mall, whatever. I wasn't really attracted to him, and even after we'd been sharing a house for two years, he still hadn't seen me m naked, and we hadn't really fooled around ...

But I looked kind of cute wandering around in cut-offs and a halter, right?

I'd been friends with Oscy's sister, and gradually gotten to know him. A real nice guy, and when he'd offered to rent me a small room when things were going hinky for me financially, I went for it.

I had previously had a great job as a dental hygienist until I got caught selling the laughing gas and embezzling a little. And then suddenly, I'm bagging groceries at Kroger's and don't have much moolah.

I'd slowly found out about the whole dominant mistress thing. Once I remember that I was hanging out in my short-shorts, and standing over Oscy as he was scrubbing his kitchen floor, and I began jokingly barking orders at him to work faster.

Oscy was always doing cleaning and stuff, he was a neat freak, and I was a terrible slob. We had a chore wheel, but I always seemed to forget that I was supposed to help out, and I noticed that if I let him, he'd clean my bathroom and make my bed, everything.

Then I began looking at Oscy's porn magazines and seeing his websites-kinky shit.

It turned out that Oscy was especially excited by women who were kind of bitchy and wore those lace crop-tops, high heels. When I expressed regret that I had no leather corsets or miniskirts, he went out and bought me some.

I gave him a hand job one night, to take his mind off the fact that I'd blown the grocery money on my boyfriend's methamphetamine habit, and Oscy asked me to tie him naked to the bed and tease my dick more with my long pink fingernails.

It was really interesting. When Oscy was on the verge of cumming he told me I could "calm it down" by whipping his dick with his handy-dandy geeky slide rule.

Tying a string around Oscy's cock and balls, and pulling it to make his dick engorge was a riot-and then I'd stroke it for a bit, running my forefinger up and down this big thick vein on the side of his penis.

Oscy's kind of a tubbo, and it was hilarious watching his dick leaning against all that flab as it ached for my tender touch...

Tickling his balls, also tickling a bit under his arms was a party too.

Usually I'd rub his dick for about two or three hours, once a week, and eventually Oscy stopped asking me for the rent completely, and he covered the food as well...

He would just tell me to write down what I wanted from the store.

And after this, Oscy got me a nice Visa Gold, and this covered me going to movies and out to eat, even when I wasn't with him.

Of course he liked it best when I spent money at lingerie stores, and stuff.

One Saturday morning, right after I'd returned from jogging, and was sweating up my tee shirt and shorts, Oscy approached me, stark naked.

He had sort of begun walking around wearing less and less lately, and I had become accustomed to walking in when he was jerking off in my dirty panties.

At this point, he had never seen me nude at all, so it was kind of a one-sided thing. He was embarrassed sometimes, because I would walk in and out of the bathroom when he was showering...

But on this Saturday, Oscy asked me if I would whip his ass while he leaned over the arm of the couch. He had this wicker carpet beater that had belonged to his mom (neurotic, right?) and hoped I would indulge him.

And hey, why not? Oscy had ponied up to pay for repairs to my car after I'd wrecked it driving drunk and done a lot of other things for me...

"Get over that couch end, you bad boy!"

Oscy screamed and cried as I whipped him, and I had a few annoyed resentments about the way he chewed his food, and that kind of thing. So whipping him got a lot of stress out and it was certainly upper arm cardio.

When he cried, I called him a little bitch as I swung the carpet beater again and again on his reddening ass.

I'd learned a bit about this stuff from other people. My friend Bonnie had married a geek and then decided at some point that she didn't want to fuck him any more.

She told me that Spofford had been actually aroused when she cheated on him, and got excited when she reluctantly allowed him to jerk off in front of her while kneeling.

"Seriously, Kelsea" Bonnie told me "I didn't even want Spoff to see me naked anymore, and I found out that he was kind of aroused by just being naked on his own with me parading around in tight clothes. Spoff even let me have the master bedroom for myself and my lover, Vincent."

Bonnie grinned, telling me that Spoff now gave her massages, and sometimes even gave Vincent massages as well, if she ordered him to...

What an interesting psyche poor Spoff must have, I thought...and Oscy too, apparently.

"I beat his ass and make him strip when he doesn't take care of the home chores, and it just makes Spoff kind of super-obedient. I am thinking of having Spofford rent an apartment and just come visit me at the house now and then!"

This really helped me in my relationship with poor, nerdy, Oscy. Oscy would often lie on the bed and I'd tie his wrists and ankles together, and whip his ass for about twenty minutes as he lay on his stomach, weeping...

And then I'd turn him over on his back, for a nice long hand job...

Yes, and sometimes strip down to a bustier and panties (he loved powder blue and pink as colors) Other times, like when the house was chilly, I wouldn't take a stitch off.

Just wear tight cashmere sweaters, and that was more than enough to keep Oscy going.

Teasing him "I'll never take off this sweater and let you see my nice breasts, they're for real men, you little pussy faggot!"

Man oh man, how that drove Oscy wild.

We didn't always do the talking like that, sometimes while I played with Oscy's dick we talked about sports, music, stuff on TV. But as I jerked him, Oscy would begin to pant more and talk less, and then finally he'd just be begging to cum, the poor creature.

My hand would get slower and slower on his poor dick. Up and down the manicured fingers would go, rubbing the engorged cock-head glans, very slightly...a feather touch!

And then I'd pull off one of my high heels and pound his dick into a tiny worm as he squealed like a pig!

Or, I'd keep my shoes on, and stand on his chest for a bit, pounding the spike heels into his nipples for a bit.

After he'd cum in my fist, and I'd untied him, Oscy would give me a big hug, and sometimes take me out and buy me something nice. We were big jewelry store customers.

I always wondered why my hot boyfriends couldn't be as considerate as my nice, beta male roommie-landlord.

One problem Oscy had was meeting his goals. He'd promised himself that he was going to remodel his kitchen, but the project had been lagging for years.

It was kind of annoying, everything half painted and nothing done.

So I told Oscy one day that although I'd continue to spank him and play with his dick, I wasn't going to let him cum again until he finished the remodeling.

It worried me, because I knew he could go to jerk off in some public restroom somewhere, and we couldn't have him cheating, could we?

My Aunt Ingrid is a classy dame. But, not really very rich. She loves cultural stuff, opera, and plays and the ballet, but it can get expensive.

Auntie Ingrid met various older men who liked taking her out. Some of them were gay, and just wanted her company at these cultural events, but others wanted her to fool around with them afterwards, especially if they'd taken her out for something expensive like surf-n-turf.

There was one chap, Gerhard, who kept pressuring Auntie Ingrid for sex. She wasn't really that into him, though she enjoyed the dinners and opera and the occasional gifts.

Finally Auntie Ingrid let Gerhard go down on her, and his oral skills were fairly good. Why not have a guy send you flowers, take you out, and then buy you jewelry and lick your twat?

And Auntie noticed that if she kept putting Gerhard off, he would go out with other women, who gave him more for his buck, and that couldn't work out well.

So Auntie Ingrid put Gerhard in a chastity belt. She even invited me over once to see the sad, pudgy old geezer (Foreign Service retired) standing in his nice living room, naked but for the "Iron Maiden".

Ingrid told poor Gerhard that she'd never fuck him, and she wouldn't let him cum, either, unless he took her to five dinners and expensive cultural events every month, and that he had to drop by and make her a meal and eat her out at least twice a week. Then, he could jerk off in front of her, once a month.

You'd think Gerhard would have taken pliers to the chastity belt and had Ingrid arrested, but he actually was kind of thrilled by it. Once or twice Auntie Ingrid invited me over as well as her daughters, Stella, Shasta and Sonja.

We would all sit, fully dressed as Auntie gave Gerhard the key to the belt, and he'd whack his Wee-wee right in front of us.

Stella, Shasta and Sonja would even play a "Red-light-green-light" game where Gerhard had to stop and start playing with himself again and again, and it led to an incredible white mess on the floor, and of course we had Gerhard lick that up.

Gerhard was so excited he wanted to marry Auntie Ingrid and have all of us live with him, but Ingrid felt it would be better to see him now and then, so she could still fuck construction workers.

"It keeps Gerhard focused, dear." Ingrid explained to me. "He can't touch himself, so when he doesn't see me, he just thinks about how attractive I am, as well as you and my daughters, and then wants to spend more money on a poor widow. Why not?"

And I began seriously wondering if Oscy could have the same deal. When I told Oscy about it, he told me he actually already had a chastity device that he'd never really used, and this would be just awesome.

But, after a few weeks of being locked up, Oscy wondered if the fantasy was better than the reality...

But it really seemed as if I had more leverage in the relationship. I made Oscy get a decent haircut and shave off his beloved goatee, and told him I was going to have my boyfriend move into my room, rent free, and I didn't want to hear any backtalk.

Because the kitchen-remodeling project still wasn't complete, I ordered Oscy to completely stop masturbating, and severely limited his time out of the chastity device.

Sometimes I would jerk his dick for a long period of time, before stopping and locking him back up, and more than once he threw quite a little shit-fit.

I began making Oscy bring Craig and I breakfast in bed before he started work, and then in the evenings, he and Craig, who was a licensed contractor, would work on the kitchen remodeling thing.

It annoyed Craig that Oscy was so clumsy and sometimes broke drywall with a hammer, so I gave Craig permission to take Oscy's pants down and whip him with a belt to help Oscy learn to do a more careful job.

After all, all that can be hoped for is that one does their best, but it's important that you really try, right? A little corporal punishment helped with that.

And of course it wasn't as thrilling for Oscy to have Craig whip him as it was when I did it, and this made him really strive to work his ass off, to avoid the consequences.

But, Oscy did pay Craig for his time as a contractor, and also gave Craig and his other crew blowjobs after work sometimes, since they were all bisexual carpenters...

It couldn't have been easy, going without an orgasm for poor Oscy and getting all this punishment, and I did ask him if he was happy...

Were Craig and I keeping him prisoner in any way. Did he feel like a hostage? But Oscy always insisted that he was a "happy hostage."

Sometimes Oscy would cry bitterly when I tied him up and then had him watch Craig and I fooling around, teasing him that a wimpy fag could never score with a real woman like me...

And of course my teasings and punishments were fairly tough on Oscy, but I kept assuring him that when the renovation of the kitchen was complete, he'd be having orgasms again.

Eventually Craig and I broke up, and the kitchen was, in fact, complete also.

I remember Oscy coming to me with pain and horninness in his eyes.

"Kelsea, the project is done. Can I cu m now?"

I did feel badly about this. It had taken nearly a year for the damn kitchen to be completed and it looked so nice now, granite counter tops, the whole thing.

I led Oscy into the living room and told him to strip. Soon he was standing in front of me in the nude, with me of course, clothed.

Oh, how he was looking at me pitifully, with that horrible chastity belt on. It looked like it was pulsating, the pouch of the belt, and that meant that poor Oscy was horny to complete distraction.

Over the past near-year of celibacy, Oscy had licked me to hundreds of orgasms, and had given Auntie Ingrid a few as well. He'd sucked off Craig and his carpenter friends many times...

Yes, did I mention that now I was letting Oscy lick me down there? Finally he was occasionally allowed to see me naked, and to worship my entire body with his tongue, which he enjoyed far more than his attentions to Craig and the guys...

But this had really made poor Oscy even hornier. Also, I had Oscy occasionally attending to me in the bath, and that was quite arousing for the poor thing as well, especially when I let him wash my breasts...

And of course for days poor Oscy had been following me around, watching my gorgeous ass twitch in the tight shorts...I had a habit of wearing stockings with denim shorts, and heels, and this made the poor bastard very distracted.

But today, when Oscy approached me for the orgasm he so-called "deserved" I was wearing a cute little scoop necked leopard skin dress. It really was the size of a long tee shirt, and of course my tits were busting out of it.

Oscy just hoped I'd unlock him and let him beat his meat, but there was a part of him that really wanted to fuck me. Which of course, wouldn't ever happen...

I just stared back at him and crossed and re-crossed my long legs.

Finally, after a moment or two of batting my eyelashes at him, I said "Let's cuff those hands behind your back, baby."

I smiled and Oscy's face fell. He thought finally he'd be handling his dick, or better, handling ME.

I had Oscy turn and I locked his wrists and then began removing the chastity device. I brought a little basin of soapy water from the bathroom and sat back down on the couch, smiling as he stood, naked and awkward, in front of me.

I began washing Oscy's cock and balls, which were fairly rank since they'd been locked up for so long, and then I shaved off his crotch hair. (Pubic hair is for "men" you see.)

Oscy looked with lust at my long fuchsia nails as they gently scraped his rapidly elongating penis.

"Does that feel good, baby?" I murmured. "After all this time, being locked up. I'm such a meanie not letting you out."

Oscy panted and stared at my glorious cleavage.

"I know I've been so busy I haven't had time in about three weeks to even take off your belt for a cleaning and a cock-tease, much less to give you an orgasm."

I sighed and my boobs bounced in the leopard skin dress.

"But I told you" I playfully waved my forefinger in his face. "No squirting till the work is done!"

Oscy was panting and thoroughly enjoying the penis rub.

"But it must be so lonely for your poor little thing in that nasty device, I know."

I licked my full lips at poor Oscy, and he smiled dreamily. But still, he was a little unsure, as if he didn't know if I was going to betray him and re-lock him for the fun of it, and make him wait for his reward for a few more weeks.

And Oscy had been so nice to me. He'd bought me a pretty set of diamond earrings that he'd gotten the money for after I'd convinced him to sell his boat.

Although he despised Katy Perry and Taylor Swift, he'd taken me to both their concerts when they came to Mount Chapel, and even stopped playing his heavy metal records around the house.

Also, Oscy had finally given up his lowlife friends and spent much of his time giving me long massages, which must have been intensely frustrating, as I lay, basking in the air conditioning in my bikini underwear.

I was now sleeping in his room, which had the big A/C unit, and he was sweating it up in mine, which just had a very inadequate ceiling fan.

And now his belt was gone and I was thoroughly enjoying stroking the swelling penis.

"I hope you understand how important chastity is, Oscy." I said in a nice way.

"Yes, of course, Kelsea. I need it. It reminds me of your incredible beauty, and I can concentrate on that. And not cumming whenever I want to makes me more obedient, you know? I'd much rather take you on long shopping trips than hang out with my loser buddies."

Oh, that sweet-talk. Boy he was really trying to con me into getting him off! It was funny, but on the other hand I could see how all these months locked up had not really been all that good for his penis, which was empurpled now, and so soggy with pre-ejaculate.

I tickled the underside of his organ and leaned over from my spot on the couch and gave Oscy's sweaty neck a long, deep, passionate kiss, following it up with an intense hickey.

"You know I love you too, don't you sweetheart?" I whispered this in his ear.

"Oscy, I don't think you're a very manly guy, and that's really too bad."

Oscy looked sad and a tear rolled down his cheek. "I know." he whispered back.

"I mean, I really need to bed a hard-fucking, hammering type of guy. Buy you are a sweet, sweet boy and that's what I need in the long run."

I paused. "It's too bad that little pre-mature ejaculating wiener of yours just isn't very big."

Oscy looked sad and was panting madly since he was now on the brink of release. My humiliating comments were kind of sending him over the edge as well.

I stopped stroking him suddenly, and kicked him lightly in the nuts. Oscy's legs buckled briefly, but he rallied.

"Oscy go and get me that wooden paddle on the coffee table, hon. I k now your hands are manacled, but you can certainly bring it here in your teeth."

Oscy looked a bit frightened. "You're going to spank me, Kelsea?" Of course he thought it would just be me giving him a nice orgasm. Should he rebel?

I gave Oscy an implacable look. Sighing, Oscy went over and bent over the table, grabbing the paddle in his mouth, gingerly, so his tongue wouldn't get splinters.

As he brought it back, his cock looked quite comical bouncing up and down.

I took the wooden paddle from Oscy. He really was starting to be freaked out by my puzzling behavior.

I stroked Oscy's cheek. "Now you're on the edge, and I don't want you to cum too fast. You've been looking forward to this, and I don't think I'm going to let you cum again after this orgasm until your birthday, which is just after Thanksgiving."

I paused. "It's because you really enjoy cumming more after you wait a bit, you know?"

Oscy looked somewhat alarmed. What was this? He thought of course that this five-month chastity period he had endured had just been about spurring him towards finishing the home improvements...after he finished the work he'd be free, right?

But from what I was saying now, he might have another six-month sentence coming up.