Miss Chianti's Troy-Boy

Chianti finished brushing her hair and gave it a cursory look, and the doorbell rang.

Chianti put her brush down, and pulled the scoop neck of her pretty pink sundress down a little, just so the jugs poked out a bit more.

The bell rang again. "I'm coming!"

What a beautiful dress, sleeveless and so short. Purchased by Ingersoll, a sad little man who needed his anus "fisted" by Chianti, using surgical gloves, at least twice a month.

Funny how sometimes men have better fashion statements than I do. Chianti took some translucent powder from her dressing table and rubbed it into her full lips.

Oooh, pouty. She smiled and spun on her heel, as the doorbell rang yet again (I will cane him!) and unlocked it.

"Troy, how nice to see you." Chianti kissed the cheek of the pallid little man...a nice neck hickey, why not?"

Troy smiled beatifically, and let her rub her bosom into his sunken chest. Chianti turned and led Troy by the hand into her living room.

"Thanks again for helping to install my sump pump."

"Don't worry about it, Miss Chianti. It's a side thing with me, when I'm not crunching my Dad's numbers."

"And you seem like you recovered from the activities at "Sidney's Kidney"

Troy decided to change the subject. "Miss Chianti, you look so wonderful. That is quite a dress."

There was a sheen of perspiration on Troy's balding pate.

Chianti traced a finger down Troy's shoulder and smiled impishly.

Giggling, she jiggled her cleavage, and Troy became very flustered.

"How has the month gone, Troy?" They sat down on her divan, and she took his hand gently. "I didn't really have a chance to ask about it the other night at the club."

Troy tried to not think about the other night at the club, although his jaws were still somewhat numb.

"Well, if course it's been quite frustrating, but we've been doing this a long time." Troy smiled weakly.

"I was laughing at your e-mail about how you at least don't have all the problems that your friends do with relationships and dates, you're all locked up 29 days of the month." Chianti beamed again.

Troy gave her a grateful look and handed Chianti a wad of cash, which she waved gaily and put on the little table next to the divan.

"I-some nights I keep waking up in some pain, but it's silly, I've been doing it so long now." Troy absently rubbed his crotch in memory. "And when I am out running, it bounces."

"I know." Chianti said understandingly. "But I felt like we had to switch to the new belt because you, you know, broke into a couple of the others, and you yourself said you want complete security."

And this was true. Troy now had a piercing that was locked into his penis and also into the metal shell. He was truly locked. He'd paid for the damn thing, and it had been expensive.

Chianti crossed her legs and took Troy's hand again. "So it's a little frustrating, I get it."

Chianti pouted, feeling sorry for Troy.

"Baby, I'm sorry if it was too much."

Chianti had this way of looking at a man, and making him feel like he was the most important thing in her world. She did this with about twelve clients a day, but it was quite a talent.

Chianti reached over and patted her long, dark pink nails on Troy's trouser zipper.

"Do you like my nails, Troy?"

"Yes, are those butterflies stenciled on them?"

"Yes., but if you don't look closely at them, they look like little diamonds, don't they?"

"Oh, God, yes, Miss Chianti. It's gorgeous."

"You know, you can just call me Chianti, don't you, Troy? We've been doing this for a couple years now, babe."

"I...I know. I'm just so, in awe, I guess."

Chianti laughed deep in her throat. "Do you want to undress now?"

Chianti wondered if Troy wanted to bring up the antics of the week before, although he'd ignored her broad hints up until now.

When Chianti and her friend Aveline had dressed Troy up in drag and taken him to the "Sidney's Kidney", the worst dive in Buttermilk Falls.

This notorious nightclub, owned by Sid "The Squid" Verrocchio, was usually filled with angry, horny mob boys. And, as soon as Troy, looking truly strange in a shimmering gold dress had been brought in there...

Chianti had taken Troy by his feather boa and pushed him into the men's rest room and whispered to a couple of bi-curious customers, who'd rushed in afterwards and had quite a little party with the startled ladyboy.

Troy's cock was locked, of course, but they made great strides with his mouth and asshole...Chianti had caned Troy for getting a run in his stockings, being forced to kneel on the floor, but what could you expect?

Chianti had put Troy in the trunk of her Uber on the way home, and then he'd been shoved out on his back porch, so he could clean up, as he shared his house with his brother...

But even with Chianti hosing him off, and giving him a pair of overalls to wear inside, Troy still had looked a bit peculiar.

Perhaps Troy thought if he endured this ordeal, Chianti might let him orgasm a week early, perhaps after he'd been hosed down...but she'd just made a rude remark about hopeful transvestites, and left the yard.

And truly, he was on a monthly schedule, and an early orgasm might have disrupted things...right?

Troy had said nothing about the unfortunate evening, and Chianti watched now with a gentle smile, as he undressed, folding his suit and putting his undies on top of the little pile of clothes.

Now, Troy stood in front of Chianti, his penis attempting to push out of the little steel prison. Chianti snapped her fingers, and Troy spun around and she locked his wrists behind his back.

Then she twirled Troy once again, and unlocked the chastity device, and removed the painful piercings. And Chianti smiled as the "snake" swelled in front of her.

Chianti left Troy and went to her kitchen, bringing back a bowl of warm soapy water, and she cleaned Troy's penis off, the grime of a month's sweaty detention.

Then Chianti dropped Troy's penis prison into the bowl, to soak, hoping it wouldn't get rusty.

After this, Chianti lovingly shaved Troy's now quite stiff member, and then plucked some stray hairs, which elicited a few squeaks from her submissive.

Chianti flashed a garter belt at Troy, pulling her dress up a bit.

"Like my stockings? Why don't you get on your knees, babe."

Chianti smiled encouragingly, and Troy knelt, his cock bouncing up at her.

"Now, I want you to push your pee-pee in between my calves and fuck them hard."

Troy became quite enthusiastic and began moving his hips, grinding his cock between her glorious gams. It was a little difficult moving his hips in and out without being able to use his hands, but Troy kept it up manfully.

"That's right, baby. Push and pull, but don't rush."

"N-no I won't, Miss Chianti. This feels so good, this stimulation, after thirty days of being all locked up."

"Yes, and you have visual stimulation too, babe. See, I'll flash you...no panties!"

"Oh God, this is your best tease yet. I hope I get release tonight."

"Heavy hinting, eh, Troy-Boy?"

Troy blushed but kept inserting his hopeful penis.

"Let's see, last month I peed on the bathroom floor, and you rubbed your nasty pecker into you exploded in it."

"Y-yes ma'am."

"Then you licked up the pee and semen combo, and drank the rest of my urine directly from the hole. And then the month before that, you ground your penis against sandpaper? Or was it gravel from my driveway?"

"No, (pant) That was November, Miss Chianti." Troy moaned. "Sandpaper was February.. "

Ingesting Chianti's perfume he watched her cute nails drum against her big boobs as she ruminated.

"Then there was last summer, where I told you that you had too much of a gut, which you still do, and I said you couldn't cum until you could jack your legs over your head and suck your own dick."

That had been awful, Troy recalled. He'd gone four months celibate, trying each session to reach his penis to his mouth, and mercifully, Chianti had given up that project.

But he sure had worked out more, and lost a lot of weight!

"Okay, stop now, Troy. You're going too fast."

"S-stop?" Troy gazed up at her as he continued to wiggle his hips.

Chianti clucked her tongue in irritation, and stood up. "I said STOP." Chianti grabbed a fiberglass riding crop and HIT Troy hard across the penis.

"When (WHACK!) I tell you to (WHACK!)stop pumping (WHACK!)

your worthless worm, (WHACK!)you do so (WHACK!)

immediately. Goddamn (WHACK!)it, shape up or(WHACK!)

ship out!"

"Yes-yes ma'am." Troy began weeping softly. He'd been so close to cumming. This was the best way he'd been allowed to spurt in the nearly three years he'd been having these glorious, if expensive dates with Chianti.

"Here, we'll use these to calm you down. Kneel."

"Those are metal jacks, Miss Chianti."

"Yes, I played with them years ago. I want you to kneel on them, or I'm not going to let you cum this month."

Troy looked stubborn, so Chianti went around to the back and commenced operations with the fiberglass cane on his bare bottom until Troy shuffled forward and with a groan set his knees into the sharp metal.

"There we go!" Chianti said brightly, as if they were preparing to go on a cruise.

"Y-yes ma'am."

"That's my obedient boy. Now I'm going to sit back down and let you do your push-push."

"Y-yes, ma'am,"

"Not as bad as when I made you dip your dick into Preparation H and then jerk off with my driveway gravel, is it?"

Troy was silent.

As Troy pushed in between her calves again, he felt the spikes in his knees and wondered if it all was worth it. But then Chianti flashed him again, and what are you going to do?

But he still looked somewhat glum.

"Aww." Chianti pouted. "Troy isn't happy, is he?" She paused, a butterfly tipped forefinger perched on her adorable little chin.

"I know!" Chianti smiled. "More stimuli." Chianti pulled off her little frock, and now she was clad in a demi bra and panties, and of course, the ever-present garter belt.

The enhanced breasts (and her succulent rear end) were a gratuity of Doctor Piggie-Snout, a plastic surgeon submissive who Chianti had seen back in 2009.

But fortunately, Troy didn't know that!

"You like this view, don't you Troy?"

"Yes I do, Miss Chianti."

Troy's left knee was bleeding a little, but he didn't seem to notice it.

Troy began moving his hips more enthusiastically in and out of the little crawl space provided by Chianti's glorious calves.

Despite the glorious distraction, Troy winced quite a bit, his knees were really in bad shape now. He tried desperately to shift so the jacks didn't always press in the same place.

Still, the combination pain and humiliation was terribly arousing.

Suddenly, Chianti leaned back in her chair and lifted her legs.

Using the tips of her toes to envelope Troy's cock, Chianti rubbed both feet against his organ, rubbing both feet against the tumescence.

It seemed almost narcotic for Troy, especially in the scratchy nylon stockings.

Troy was fascinated by nylon. A previous Mistress, Brandy Alexander, had put Troy in pantyhose with the crotch cut out, and had him clean her house...but that only made the fetish strengthen in his mind.

Chianti rubbed the toes of her stockinged feet all over Troy's glans, and it swelled and began to look somewhat purplish.

"You aren't going to make a mess just yet are you, Troy-Boy?" Chianti asked in a soft voice. "I mean, as the song goes, we've only just begun."

"I'll try to resist until you give the word, Miss Chianti." Troy was trying to hold back, but this was really something. Chianti had the most exquisite legs, and her toes were amazingly dexterous.

As Chianti continued to stimulate Troy's penis with her little feet, now sliding slightly up and down the shaft, she removed her demibra and began cupping her breasts.

"You like my boobs, don't you, Troy?"

"Oh God yes, Miss Chianti."

Chianti squeezed one of her nipples as if it were an errant pimple. She could squeeze it hard, as it didn't feel much, thanks to the surgery. (Doctor Piggy-Snout was a bit of a butcher, but it was pretty)

"It's sad, of course, because you'll never get to kiss anything as beautiful as a nipple like this."

Chianti held one foot firm under Troy's cock and used the other atop his organ to rub just a little faster.

"Only big, strong men get to suck titties, and fuck girls like me."

Troy blushed in humiliation.

"What kind of a sorry little wimp would let me dress him in tranny clothes, and then provide a cock sucking party for my friends?" Chianti laughed hysterically as she continued to rub Troy's cock.

"Y-you told me it meant a lot to you, Miss Chianti." Troy was near tears thinking about this.

Chianti flicked her nipple, and then pulled up her boob and sucked on it.

Troy, considering what a worm he was, began welling up with tears, but this made his penis even closer to an orgasm.

"C'mon, Troy. You like dick. Lots of dick. I should call you Tracy."

"N-no, I just did it to please-"

"Or Troyce. Troycie. I had a friend in school called Troycie."

Troy babbled, and his cock grew harder.

"I think maybe I'll take you down to the glory holes in the john at Buttermilk National Park, and see how many wee wees you can dry. We could take contributions like a Fun Run thing."

Troy began weeping in absolute despair and humiliation, but he kept on pumping. He did try to move his hands out of the cuffs holding him, but this was to no avail.

Still, how exciting. How he paid this young woman for weekly teasing and humiliation, and here he was, kneeling on metal jacks and having his penis manipulated by her toes...it was so arousing.

Finally, just as Troy's penis was going to spurt, Chianti pulled her feet away dramatically.

"Okay, Troy-Boy, I think it's time for us to lock you up and send you home."

"Wh-why, Miss Chianti?"

"Well you seem to have an unhealthy sex focus on me, and I feel impure."

"What?"

"Yes, I'm a good Catholic girl. I want you to spend the next month thinking about our relationship."

"But-but I always-"

Chianti, bored with this interaction, whistled between her fingers and the bedroom door opened, and out lounged Sid "The Squid", owner of the "Sidney's Kidney" nightclub where Troy's mouth and anus had been given so much gratis exercise a week or so before.

Sid was muscular, yet somewhat paunchy, and wore a "Wife beater" undershirt. In his mouth hung an ever-present Lucky Strike and, simultaneously, snuff.

"What the fuck, Chianti?" Sid's mouth upturned slightly. "This the little faggot who was kneeling in my toilet, Vinny and Vito and Cotton head told me he gave real good head."

Sid paused. "He gave head in my head. He communed in my commode."

"What a comedian you are, Sidney." Chianti said with a grin.

Not here, c'mon! Troy, bound and kneeling, felt a horrific betrayal He stared at Sid and then Chianti who was giggling.

Kneeling with bound wrists, just as Chianti had had him in the restroom of "Sidney's Kidney" and now this-this brute was standing there.

"Siddy, Troy doesn't want to leave. Can you talk to him for me?" Chianti asked lazily.

"Well he does pay you ten C-notes, right?"

"See, even Sid sees it my way." Troy said, before realizing he should shut his mouth before Sid filled it with you know what.

"Yeah, I know, but I'm tired now. Get him out of here and I'll make it worth your while."

"He can make it wort' my while." Sid looked greedily at Troy.

"No, that's all right." Troy said nervously.

"You little queer, who the fuck you think you are, rejectin' me?" Sid came over and lifted Troy up by the ear so he was now standing, naked and humiliated.

"Damn, he's hot for this, look at his wiener." Sid reached down and grabbed Troy's balls and squeezed them cruelly.

"You like getting action off my chick, don't you, faggot?"

"Wait, let me lock Troy back up." Chianti said suddenly. "I don't want Troy beating his meat when he gets home."

Chianti hopped up and took the chastity prison out of the soapy bowl and relocked it on Troy's crotch with quick little fingers.

"Y'know he can prob'ly take that thing off wit' pliers, Chianti."

"He pays me a grand a month to keep him in that thing, and he paid five grand to have it constructed. I think he'll leave it alone. And see, how I have to loop the piercings in, again? If he used pliers on it, he might eff up his penis."

"Yeah, but it ain't like he uses his dork for anythin' normal." Sid was overcome by his own wit, and almost swallowed his cigarette, laughing.

Driving home, Troy felt aroused and traumatized. Before leaving, Sid had thrown Troy across the couch and given him thirty-five with his belt and then he'd skull-fucked Troy to a creamy finish line.

Chianti had winked at Troy as he'd limped, crying, out the door.

When Troy arrived home, he felt his cock was so hard in the device that it was about to burst.

Troy took a long, quick shower. Troy heard his brother Trent banging the bottom out of his girlfriend in the rec room.

Troy went into his bedroom and sat n the bed and put his head in his hands.

Why couldn't he be normal? Trent had a sweet, giving girlfriend and Kathy had more than once offered to set Troy up with one of her pretty friends.

But Troy was only focused on the evil girls. He'd dated the bitchiest girls at Swarthmore, the sort who flicked their cigarette ashes at him and cheated regularly.

When Troy and Trent had gone to work in their father's firm, Trent had laid all the secretaries, typists, file clerks and receptionists (of either sex, Trent was a bi-boi) and Troy had taken the tearful ones to lunch the next day and listened to their complaints about Trent's infidelity.

Oh, shit, thinking of that one flaxen haired admin who Trent had dumped...was her name Chantilly? was making Troy hard again.

Would he have to take another shower?

There was a light tap on his bedroom door. Looking down at the cage, Troy quickly put a robe on and answered.

There was Trent's gal Kathy, in a little powder blue bustier and cut-offs. What a hot girl she was!

Kathy put a delicate hand on Troy's arm. "Hey cutie, I was going to make Trent an egg sandwich, do you want me to get you anything?"

Troy smiled at Kathy. "You are such a nice girl."

Kathy pouted, much as Chianti had. "Not a hottie?"

"You are too good for my brother, that's for sure."

Then Kathy's nose wrinkled and her chest heaved. "I'm not that nice, I'm naughty."

But of course Kathy most certainly was not naughty. Chianti was naughty.

Kathy was a flirt. Though. She pushed Troy back into his room and made him sit on the bed and she sat on his lap and kissed his neck playfully.

"You are such a foxy man, Troy. I wish you'd let me set you up with my friend Donna."

"The one with the moustache?"

"Shut up! She just shouldn't wear light lip gloss." Kathy kissed Troy again.

His dick was trying to pull out of the piercing. This was a situation.

Kathy undulated her butt cheeks on Troy's lap.

It was tough enough throughout the months between his dates with Chianti. Looking at the cute secretaries and college girls parading up and down Buttermilk Boulevard, but this Kathy business was unbelievable.

Obviously Kathy had just jumped out of bed with Trent, and had hurriedly put on scant clothing. Her tits were shifting in the snug bustier, rubbing against Troy's narrow chest.

Trent looked in. "You taking my girlfriend, big brother?"

That was the worst of it all, Trent was the YOUNGER brother, and he'd lost his virginity first, and had dated what seemed like thousands of women.

While Troy just went for a monthly visit with that evil bitch, Chianti!

Kathy looked up at Trent. "I bet he's better in bed than you are, Trent. I want him to meet Donna."