Bibbit Smithers's Ordeals

The Colonel's Chastity Tales
June 2018 Stories

BIBBS JUST CAN'T GET A BREAK

Bibbit Smithers, Senior wondered why he was spending an expensive week at the Thumbscrew Lodge. Bibbs had had his ass kicked by his older brother, "Smitty" which you would think would have been bullying enough, right?

And, Bibbs, no jock, had been charged with handing out towels to the athletic teams as his Work/Study job at Amherst, and the jocks had all enjoyed flicking the wet rags at poor Bibbs, and horse playing with him in the shower room.

Things had changed, and he thought he was happily away from the bullies now.

After all, the so-called "nerds" and "Geeks" and "Dorks" were men with brains, and those who ran the country, right?

Bibbs was fairly well off now, and left a tenured professorship in microbiology to start what was now hthe largest paper cup distributorship in the state, and was a big mouth in the Buttermilk Falls Chamber of Commerce now.

Aspen, Bibbs's fiancée, had told Bibbs time and again that size didn't matter, he had a nice penis, and if he couldn't stop the premature ejaculation, he was a nice man to cuddle with.

But Bibbs had dated other women who laughed at his little dick and made all sorts of cruel remarks.

His first wife, Trendi had often asked sarcastically "Is it in yet?"

Brioche, Bibbs's second wife had usually locked herself in the bedroom with a vibrator to get her orgasms...

But Aspen loved him, and he was a successful chap, and tutored inner-city chess champions.

Bibbs had arrived. Why would he go to the trouble of coming to Thumbscrew Lodge to be belittled and sexually sodomized by thugs, big, tough, gay male prostitutes...and paying for it?

Now, Bibbit was tentatively walking along a path and saw Peabody Dill, owner of Thumbscrew...

Peeb was stark naked, and pulling a cart with two dominant women and a male coachman in it, all dressed in leather.

The coachman swung a whip, which caught Peabody on the back of the neck and then again against his ass. "Move, it, horsie!"

The girls laughed and the coachman snorted.

Bibbs reflected that although Peabody had a controlling interest in Thumbscrew, and was making a fortune.

Of course Peabody had invested in this so he could serve dominant men and women full time, and had no better status than any of the other slaves, all of whom of course, were paying clients.

"There's the little faggot!" Bibbs looked around fearfully. Four big guys, two wearing absurd Fifties leather jackets, and one in a blue overall. Huge muscles, cigars, tattoos.

Bibbs knew the most interesting thing about this was, Bibbs was (sort) of heterosexual, and these guys were really all gay...but here he was the faggot wimp!

When his trainer had sent him out of the cottage that morning, Bibbs was stark naked except for nipple clamps and high heels.

And now was wearing thick pancake makeup, his penis, all four inches, straining hard.

He was supposed to be the effeminate target of these guys...

Yesterday, they'd tied a rope around his balls and made him run behind a convertible as they drove about five miles per hour...

And then he'd been forced to eat soap chips that evening...

And today, another plague?

But he was asking for it! No one had forced him to come here.

Bibbs had discovered Thumbscrew Lodge from a guy who had been panhandling in front of Bibbs's favorite car wash.

Stretch had told Bibbs that he made a bit of a "living" "using a nail file on Coke machines" but also dominated rich men for occasional profit, and had been fired from Thumbscrew some months before.

Bibbs had driven Stretch from the car wash to his house, where Stretch had tied Bibbs down, sodomized him, stripped him and robbed him...and then Bibbs had gone to Thumbscrew, assuming more of the same.

Now Bibbs was stumbling awkwardly in the mud wearing tranny sized kitten heels. He saw the guys advancing on him.

Bibbs had been given an assignment by his trainer to go in the woods and gather some blueberries in this ridiculous getup.

The guys of course were supposed to intercept and persecute him a bit, probably feeding him their cocks, and whipping him with willow switches, that sort of thing.

Decked out as he was with his earrings, heels and bright pink polish on all twenty of his nails, ..the men were joyfully moving in like sharks on a fat tuna.

"Where you going with that basket, queer?" Leather Jacket #1came close to Bibbs. "Nice earrings, queen."

"Um, I'm just minding my business guys. Got to get these uh, blueberries. I don't want any trouble." But of course Bibbs did want trouble, didn't he?

Bibbs noticed the growing bulge in Leather Jacket #2's 501s...he must have quite a big dick.

Yesterday, Bibbs had been locked in a little cage with a hood over his head and been forced to suck about forty dicks before jerking off...he had no idea if he'd sucked this guy or not.

Bibbs tried hard to placate the leader with the leather jacket, but this guy was looking for a fight.

Bibbs heard a scream and looked behind him and saw Claiborne Altwn IV, his roommate being dragged across a meadow by a chain between his clipped nipples.

The young man who was doing the pulling, a beefy chap with a goatee, or maybe a Van Dyke? stopped to talk to Bibbs's persecutors.

Clay was wearing shorts and a blue sailor suit top, and one of those naval berets, like Donald Duck had.

The blue top was ripped open, and the chain was hanging on Claiborne's exposed nipples, and Clay looked as if he were in a bit of pain.

But, as Claiborne was vice president of a humongous munitions factory just outside Buttermilk Falls, Bibbs kind of figured he was here through paying big bucks, too.

"Please don't whip me, Daddy."

The young man who was "Daddy" and actually about fifteen years younger than Clay, grinned. He had a long bamboo cane in one hand and swished the air with it.

Clay's actual father, the owner of the munitions factory was a bit of a controlling asshole.

Bibbs had seen Claiborne the Third acting up at the Rotary Club, so of course the sailor outfit and the cane, it was all-therapeutic, supposedly.

Not that Clay III had ever raised a hand to Clay IV, but the screaming that had gone on at the Rotary, from dad to son seemed familiar

Bibbs assumed this is what created this neurosis that the Van Dyke beard Master had to somehow medicate...

"Why have you disappointed Daddy, Clay?" The Van Dyke guy boomed.

"Sir I don't know, Sir. Please--I'll be a good boy."

Yes, I've heard Clay Four talk in a similar tone to his father, who was confined in a wheelchair and so much less threatening...

"Son I'm going to have to take you to the woodshed" the Van Dyke master said now.

"Nuh-no. Please Sir, not that."

"I caught you jerking off in one of my socks.

I know you like the scent, but it's offensive that you did this!"

"But not the woodshed, Sir."

The woodshed at Thumbscrew was not very big, but it was where a lot of implements were kept.

The Woodshed even had a pillory where one could be locked, bent over with head and wrists through the holes, and access to the rear end forcibly stuck out!

For whipping or sodomy...or, as Bibbs had seen once, having a target painted on the gluteus maximus, so the Masters and Mistresses could play darts!

Once Bibbs had seen Rosebeth McMillan, a sad-eyed commodities broker locked in the pillory.

Rosebeth's rear end had been the target practice for several Masters and Mistresses with BB guns...

"I didn't ask for your opinion, boy. You're a mouthy little shit, ain't you?" The Van Dyke guy winked at Bibbs's leather guy, winking, and they all laughed.

"Sir, I didn't mean" oh, Clay was whining now.

"You're not going to get the privacy of the woodshed, boy. Take down your britches right now. We'll see who is the big man with the opinions."

Claiborne burst into tears. "P-please, I didn't mean--"

Impatiently, the young bearded guy put the cane under his arm and reached over, undoing Clay's trousers.

He yanked them down, and underneath, Clay was wearing panties, which were also pulled down.

Now Clay's stiff cock was out, although it was encased in a little steel cage. Boy was Clay horny!

The leather guy and his pals were laughing at Clay's panties, and even Bibbs smiled, although he felt he was being disloyal to a fellow submissive.

"Motherfuckers got a garter belt on too!" the blue overall man remarked.

Then Van Dyke commenced operations with the cane.

There was a rustle, and coming out of the woods were two naked, middle aged men, they both had their hands manacled behind their backs.

But what was even more awkward was that there was a metal loop around each man's cock and balls, and a foot long chain connected the two loops.

Bibbs watched in horror as the fellows kind of ambled along, facing each other, as the chain forced them to.

Behind them was a slender woman, perhaps five foot three with a shock of bright red dyed hair.

"Guys!" How's it going?"

"Hey there, Cronyn" shouted the first leather guy.

"You're doing well, huh Turk?"

"Oh yeah." Turk said, grinning." I just have little Blueberry-Blue balls boy here."

Turk gestured to Bibbs, who stared down at his ill-fitting kitten heels.

"So I have Wart and Wick here for the weekend. They're brothers."

"Boy what a sick family they must come from." Leather Jacket #2 observed sagely.

"Yup. Their doms sent them here to be improved for seventy-two hours while their homefolk enjoy a Bermuda vacation."

"Wick, please walk slower." Wart pleaded. Wick just growled back at him. It was clear the two siblings didn't get on that well.

"Wart, learn to get a move on!" the redhead shouted, laughing, and she swung a short three wire whip that left long red welts on Wart's back.

"Oooh, I think I broke some pimples on your butt." Cronyn said, giggling.

Wart tried to walk a little faster but both he and his brother fell in the mud now.

There was uproarious merriment from Bibbs's gang, and the redhead began lashing down at the two to get up.

As she bent over, Bibbs enjoyed the view of her considerable cleavage in the snug black tee she was wearing.

Bibbs made a note to himself to see if he could have a private session with Cronyn that evening.

"This-this isn't my fault--Ow!" Wick screamed.

Wick tried to pull himself out of the mud but he couldn't get up until his somewhat overweight brother cooperated. This of course because of the damn chain.

Cronyn whacked away at Wart's chest, and he howled as well.

Cronyn smiled. "These two don't even live together, separate lives, but Wick's tranny and Wart's dominant girlfriend surprised them with this unpleasant holiday, being connected!"

"Oh, goddamit Wart get the fuck up, we'll be laying here all day and Cronyn will never stop hitting us!"

"That's for sure." Cronyn laughed.

Finally, after much rising and falling, the two men were on their weary feet again. They were facing each other in a rage, with fists clenched.

Both their crotches looked somewhat sore with all the dragging, because of course the scrotal locks were so tight...but Wick's cock was quite hard, and Wart's was getting there.

What the fuck is wrong with guys like us? Bibbs asked himself...what a curse masochism is.

Cronyn laughed. "They are true idiots, these two I am trying to get them to suck each other off, to take a picture for a Christmas card for their Nana--"

"Lovely family, I tell ya" Turk smiled.

"But I beat them all day and night with true abandon, and they refuse. Wick especially. Homo incest isn't their thing, right guys?"

"P-please, Cronyn." Wart begged. "We just can't do that. It's beyond--the pale."

Cronyn smiled. "Well, it's a good thing you two can eat my pussy and lick out my asshole simultaneously, otherwise you'd be completely hopeless."

After Wart and Wick and Cronyn had gone on their way, Bibbs's tormenters took him into a cave in the woods and enjoyed his mouth and ass for some time...

Driving home after his "Vacation" Bibbs felt like his ass had really been pounded between the whippings and the sodomy....

And his jaw was quite numb from doing you-know-what!

***********

Bibbs was eager to return home after this period at Thumbscrew. Aspen hadn't moved in yet, they were trying to live apart before getting married.

Of course Bibbs's peculiarities would be difficult for Aspen to get used to, but maybe he could get over them, or hide them, or something.

Yes, there was a lot of doubt on this matter!

Bibbs wished Maya was still around, even if just to talk to.

Maya had been one of Bibbs's housemates, and a technically platonic friend. When Bibbs had first moved to Buttermilk Falls, he and Maya had met through a mutual friend who shared some of their odd hobbies.

Although Bibbs was an old fashioned capitalist Episcopalian, and Maya a hippie-dippie Buddhist (though a cute one) they seemed to fit. And Maya became quite bossy.

She was an environmental activist, and not paid a great deal for this, and before long, Bibbs seemed to be picking up most of her expenses.

"You don't clean up after yourself, Bibbs, you're a snob...and you say you have submissive interests? Submissive to what, your ego?" Maya was a riot, wasn't she.

Although Bibbs never saw Maya in the nude, or shared her bed, he found Maya had a humiliating way of getting him to do things...

Penalties, some rewards, but certainly more stick than carrot. Bibbs was certainly doing far more than his share of the chore wheel. Maya began punishing Bibbs for slacking off.

Once, after promising Bibbs he could have friends over to watch the World Cup if he washed the curtains and cleaned the aquarium, it was decided a woman's prerogative was to change her mind!

Maya said she wanted Bibbs to do more to earn this privilege...

Of having HIS friends over to HIS house to watch HIS television.

But Maya was weirdly bewitching. Her nipples hardened in her little U2 tee shirt as she read him the riot act.

"No, you didn't do enough. You can't watch your game, or go over to Jerry's to watch it either."

Bibbs ignored Maya and invited Jerry over anyway.

"What the hell? I'm a forty-two year old man and I spent the weekend on the damn cleaning. I deserve to watch my game."

But Maya led Bibbs, who was arguing the whole way, to her bedroom, and she pushed him on his back on the bed and removed his pants and undies and locked an adult diaper on him.

The entire time Bibbs was shaking his fists in the air, lying there, and screaming about his rights. Maya had then led Bibbs into the living room and put him on his ass, sitting in the middle of the rug., and she put a pacifier in his mouth, and he became strangely quiet.

When Jerry and the guys had come over Bibbs had just sat there and wept in impotent rage.

"What the fuck's wrong with you?" Jerry had asked, and they'd all had a good laugh at his expense. (Maya added a bonnet, too, it actually covered up Bibbs's bald spot.

But then Bibbs spat out his pacifier and began shouting, when Maya said, you have to take your nap while the guys watch the game!

So, right there, Maya had borrowed Jerry's belt and pulled down Bibbs's diaper and given him thirty, and then led him to bed, as he sobbed his heart out in misery and humiliation.

Another time, when they were having a house party, Bibbs had become difficult about wanting to buy more wine, and then he'd made a snide comment about Maya's trashy friends.

"Okay. You think you're so hot? You're going to spend the entire party standing in the corner with your pants and underpants down, and everyone will look at your bare butt. And if you give me any shit about this, I'll whip your butt in front of everyone."

"I completely agree, Maya." Miss Primrose was a middle aged receptionist at Bibbs's company who rented the basement.

After Miss Primrose had noticed Maya's treatment of Bibbs when he misbehaved, she decided that this would be good for Miss Primrose to take on as well, even if Bibbs was the president of her company.

Bibbs had tried to explain to Miss Primrose that Maya and he had a connection with BDSM, and she really had no right to bare his bottom and spank him with a hairbrush just because he forgot to clean the cat litter.

"Well, it's either that, or when you forget, I'm going to pour the dirty cat litter in your bed, Mr. Smithers.

I appreciate you letting me live here at a reduced rate, you're a great boss, but you keep forgetting. Do you want to sleep in cat shit?"

Bibbs had finally conceded that he didn't want that, and Miss Primrose had taken his pants down and given him the business.

Miss Primrose had a razor strop and other things from her upbringing and it had really improved Bibbs's behavior.

The strop had certainly made an impression on poor Bibbs when Mrs. W. caught him jerking off into her pantyhose!

And then she began finding other ways to "improve" Bibbs.

"At work, Mr. Smithers, you are often grumpy, and I think you should go to bed at eight-thirty, and jog in the early mornings. I will follow you in my car."

"Miss Primrose I haven't been to bed at eight thirty since I was in elementary school! Forget it!"

"Seven-thirty. Do you want to try for six o'clock? Oh, dear, you're pouting. Mr. Smithers go into your bedroom and take off your pants and underpants, I will meet you with my trusty strop again!"

Actually, the early bed-times seemed to really do a lot for Bibbs's mood.

When Bibbs made boorish comments about a feminist who was running for Buttermilk Falls alderman, Maya and Miss Primrose had =purchased a Dr. Denton pajama, the large onesie with the drop drawers, in vivid pink

And they'd made Bibbs watch the Alderman debates wearing that!

And Miss Primrose had, more than once, gone in to Bibbs's private office at work for offenses such as forgetting to re-fill the coffeemaker, and Bibbs had quite a few cruelties there...but he did end up becoming a better boss, being whipped by the receptionist.

And no, Bibbs hadn't been allowed to see Miss Primrose naked either, although every couple of days he was stripped and whipped and occasionally given an enema by the ladies.

But now, a party? To be humiliated by both Miss Primrose and Maya? They couldn't put him through this.

Bibbs had become apoplectic over this, as there were friends from work, and from church, and although Maya was pretty and charming, he didn't want people to think he was her wimp.

All he'd meant was, his friends had college degrees and good jobs, and some of hers were dirt bags...there was no reason to, well, embarrass him.

Bibbs had worked hard on preparing for the party, and had hoped that Maya would forget, but oh no.

As soon as the first few guests started trickling in, Maya had led Bibbs to the corner and had undone his pants, and, crying bitterly, he had had to stand there for the duration of the party.

"But this isn't a kinky party" he'd protested.

"No one said it was, you're just going to learn not to be an officious asshole.

If you make egoistic pronouncements around people who've seen you with your pants down, you'll really be ridiculous."

Bibbs had hoped people wouldn't say much, but some of the younger women, including one or two that Bibbs had taken out once or twice, really had a ball making fun of Bibbs's tiny dick.

"And to think, Celia, that if I'd gone out with Bibbs a couple more times I would've had this nasty little shrunken surprise. Better that I see it now while my clothes are still on!"

One of Maya's friends, Orwell Jenkins, who Bibbs described as the kind of guy "who thinks he's smart because he watches Animal Planet.: had been at the soiree, and very interested in all this.

Orwell made some uncalled for remarks about Bibbs's position in the corner, standing with his little butt on display!