The Bet

I guess I'd drifted off. It was a surprise to wake up with my cock in a voluptuous Latina's hand. She was milking me, and her other hand clutched my balls in a tight, uncomfortable grip.

"You were sleeping. I thought this might be a fun way to wake you. I'm Angela, Miss Maggie and Miss Leslie's housekeeper. I'm in charge of keeping you fed and clean. Miss Maggie says I'm allowed to use you for pleasure, so I thought I'd get you ready. You have a nice cock, bigger than my Enrique's. I will enjoy it now. On your back."

She climbed onto the bed, straddled me and lowered her pussy onto my cock. Her pussy was sopping wet and easily slid around me. She began rotating her hips to fully settle me inside herself, then began grinding against me, pinning her clit against my pelvis.

The whole thing was very businesslike. She continued using me like a sex toy until she had an orgasm that I guess satisfied her and then dismounted unceremoniously.

She released my hands from the cuffs and handed me a bowl of some sort of stew like dish and a spoon.

"Dinner. Eat up, I'll be back in twenty minutes to bathe you for the Mistresses. I think they are having company tonight. I expect you will be offered to the guests. If you know what's good for you make the best of it. They can be very cruel."

The stew was tasty, and I made a point of savoring it. I assumed Angela's advice about what might be in store for me later was accurate and steeled my nerves for the unknown to come. All evidence I'd acquired thus far indicated that Maggie, Leslie and their friends were probably going to use me hard later and I steeled myself for the onslaught.

The stew was pretty good. Angela returned as promised and led me to the bathroom and into a walk-in shower. I was already naked, and she stripped before turning on the water. She used a hand shower head to spray me down, then lathered me up. She paid particular attention to my jewels and my ass.

"They like all the goodies extra clean."

"They?"

"Maggie and her friends like to play with each other's young friends. I don't know how you wound up in this house, but trust Angela, it wasn't your lucky day."

"Are you telling tales out of school again, Angela?"

Neither of us had noticed Miss Maggie standing in the doorway.

"Do I need to remind you what happens if you are disloyal to us?"

The fear in Agela's eyes was palpable.

"No, Miss, I'm so sorry. Please, Ma'am i beg your forgiveness."

"Go to your room, we will deal with this misbehavior later. Be there, kneeling in the center of the room, naked and ready to receive your punishment. I expect to find the crop, the heavy flogger, and the cane lying on the bed."

"Please, Ma'am, no, I'm so sorry."

"Now."

Without another word Angela scurried from the room and Miss Maggie walked toward me.

"I have to apologize for Angela, she has a tendency to be a bit of a drama queen, I'm afraid."

She stroked my thigh with a soft touch, letting her hand slip up to cradle my balls, then slide up to grasp my cock.

"I hope you'll find that last night was actually your lucky day, despite what Angela may have been telling you. You will be taken care of, all your needs met, and live a young man's dream sexually."

"I do need to get back to school, Ma'am."

Her hand on my cock was making my head spin with desire and hearing my words about needing to return to school was persuasive, but the extreme desire this woman and the situation I found myself in was amazingly powerful and tempting.

She led me back to the bed and reapplied the cuffs. She began fondling my cock and balls, gently and seductively. I quickly grew hard in her hands and received a pleased smile from her.

The door opened and Miss Leslie entered with three other unfamiliar women. She led them over to the bedside.

"Oh, Maggie, this one's very cute, may I?"

"Of course, Gail, be my guest."

The woman who had spoken, Gail apparently, stepped close and reached out to take hold of my cock. She handled me familiarly and then cupped my balls, rolling them in her fingers before squeezing them firmly. My initial yelp morphed into a moan at the pain.

Another of the new women pushed Gail out of the way to take her turn manhandling my junk.

"Where did you find him, Mags?"

"He was hitching up 95 in Virginia."

"Nice catch."

The third woman stepped in and pushed the second one away. She was larger and a bit older, probably fifty something.

"My turn."

She had a rougher, more aggressive touch, squeezing my balls with one hand and jerking my cock hard.

"You like being used hard, don't you boy?"

"Not really."

"Tough, I like it rough. You need to learn your place, boy. You belong to Maggie now."

She kept squeezing my balls and pulled them up forcefully. lifting me and making me grunt at the discomfort. She dug her fingernails into my cock, adding to the unpleasantness of being manhandled by this unattractive, mean woman.

"Don't worry you'll get used to it."

My internal dialogue was defiant, screaming thoughts of rebellion and planning escape from this horror I found myself apparently trapped in.

The woman twisted my gathered balls next and pulled even harder, making me cry out despite my desperate desire not to give her the satisfaction. She released my cock and slid the hand underneath me searching out my asshole with her fingers. When she found it she roughly jammed two fingers into my resistant hole.

"Have you pegged the bitch yet, Maggie?"

"I haven't."

"SO his ass is still cherry?"

Her eyes lit up as she asked this question, and her fingers forced deeper inside my hole. Her grip on my balls remained relentless, but her focus was now redirected to my rear passage.

"Have you ever been fucked, boy?"

"I'm not gay."

"How delicious. Maggie, may I cop this cherry. You know how much I love virgin assholes."

The direction this conversation was taking was horrifying. I wasn't enjoying being a fucktoy for these bitches, but if they were intent on ass raping me, I really needed to find a way to escape their clutches.

"We'll see Liz, I may keep that tidbit for my own enjoyment. I found him, after all."

"I'll trade you free use of my Billy's ass anytime you want for the first crack at this one. I've got Billy well broken in. You could be the first to fist him if you'd like. I've been preparing him to take it and was planning to do him soon."

"Interesting proposal, your Billy is cute."

"His ass is becoming very receptive, and I know you enjoy that sort of thing."

"I do. It's a very tempting offer."

Liz was finger fucking me intently at this point, drawing her fingers nearly all the way out before plunging them back in fully. I was trying my best to remain stoical, but it was becoming increasingly difficult, and I mentally cursed my traitorous cock that was stubbornly hard from the fiercely erotic energy in the room not to mention the pressure she was exerting on my prostate.

"Your boy is enjoying having his asshole probed, Maggie."

"I see that."

She reached out to take the subject under discussion in hand and stroke it seductively, rubbing the glans with her thumb.

"Do you like having your ass fucked, Jeff?"

"No!"

""The evidence in hand says otherwise."

She grinned lasciviously at her pun. I appreciated the lowest form of humor but scowled at the context. The other women in the room snickered and a slim, fairly attractive blonde reached out to take my left nipple in her finger, pinching hard and twisting it. She wrenched a yelp of pain from me and smiled brightly at my reaction.

"When y'all are done with this boy's asshole I'd love to borrow him for a day or two."

"Getting tired of your pool boy Catherine."

"He's getting too used to my games, Maggie. I need some fresh meat."

"We'll see Cath, I know what you have in mind."

"I'll go easy on him. at first anyway. I'll happily loan you Dickie so you have entertainment while I use this one. He does have a very healthy endowment as you know."

I definitely didn't like the sound of that. Her southern drawl was charming, but the subtext of what she seemed to be alluding to was scary. The grin she directed my way communicated a sadistic bent that would mean an unpleasant outcome for me if Maggie agreed to her proposal.

Meanwhile Liz had taken to rotating the fingers in my anus with a screwing motion. She also seemed to have reliably found my prostate with each stroke and my arousal built with every stroke. I tried concentrating on non-erotic things to forestall the humiliation that ejaculating would bring. That would only encourage these bitches in their evil plans.

"I think he really likes this, Maggie. I bet I can make him blow a nice load, what do you say, If I can make him cum from this can I please take his cherry?"

"And I still get to fist Billy?"

"Yes, absolutely."

"Have you fisted him yet?"

"Not yet, just my big boy dildo."

I couldn't believe what I was hearing, these bitches were betting my asshole's virginity as the prize based on whether Liz could make me cum from fingering me. I focused on suppressing the arousal her fingers were causing as she worked my prostate. I couldn't resist seeing the stares of the women watching my ass' invasion and my cock twitching in response. It was obvious they were all rooting for me to ejaculate.

Catherine reached in with a bright. lecherous grin.

"Here, darling, let me give you a hand."

She took my balls in her hands, gently at first, cradling them in her fingers and trapping them with her thumbs. She began with soft circular strokes, rubbing each ball. I had to admit it was pleasant. Soon she began increasing the pressure from her thumbs though and it began to hurt. As she dug them in, I cried out loudly. A collective intake of breath from the gathered women underscored their enjoyment of my suffering,

"I swear I love balls more than anything. So handy having them out there to play with."

The fingers in my ass were becoming more insistent working my prostate, Maggie's hand pumped my cock aggressively, and Liz rolled my balls sensuously, easing up on the painful pressure of her thumbs. My resistance crumbled and I shot a mighty plume of cum that actually reached my chin.

There was much oohing and aahing from the crowd at my explosion and the heavyset woman Gail whom Liz had pushed out of the way to explore my ass wiped a glob of cum onto my lips and pressed it into my mouth.

"Eat up, slut."

LIz was all smiles, exulting in her victory.

"Mmm, your ass is mine, bitch."

She punctuated her triumphant proclamation with a hard slap to my right buttock followed by a deep squeeze.

"You get Billy, Mags. I know you're going to enjoy that. He has become such a sweet ass slut. I bet you can get in to the elbow"

"A bet's a bet, just don't damage Jeff, and I'll take good care of Billy."

"Don't worry, I won't use Gargantua on him, at least not the first time."

Gail had found a spoon somewhere and was scooping up a full load of my sperm which she brought to my lips and fed to me.

"Eat up every drop you nasty slut."

She employed her free hand to grab a handful of my ballas and squeeze them painfully. More cum oozed from my cock and she scooped it in the spoon. She brought it to my lips and let the load slide between them while twisting and pulling harder on my agonized nuts.

Screaming while she dribbled my cum into my throat made me gag and I had a coughing fit. This seemed to delight her so she too the spoon and spanked my balls with the rounded side.

"You suffer beautifully, slut. I can't wait for my turn. I'm going to use you hard."

She acquired the last trails of cum from my stomach and poured it into my mouth

I couldn't believe what was happening to me as i nearly wretched at the mouthful of cum that was being ladled onto my tongue.

"I may let you suck my Georgie's cock and see how you like his cum. He has a nice big cock, and he loves having it sucked."

Then she climbed over me on the bed, lowering her dripping cunt onto my mouth and grinding it on my lips. While she rode my face she took hold of my balls much the same way Catherine. They were already horribly sore and I cried out in pain which was swallowed up by her cunt.

Was this nightmare ever going to end? I had to escape from these insane bitches.

Eventually they all grew tired of tormenting me and the party broke up. On her way out Liz paused beside me to grab my aching balls and whisper in my ear.

"I can't wait to stretch out that pretty asshole, boy. You are going to learn to love getting fucked. I promise. If you think I worked your prostate well tonight, just wait til I get my cock in there tomorrow."

She gave my balls a firm slap and kissed me before turning to leave, laughing.

On the way out I overheard Liz's southern drawl.

"We've got to teach that boy about latrine duty. He's going to love being our urinal. I do love the felling of peeing in their mouths almost as much as I adore torturing their pretty balls."

A fresh wave of revulsion wrenched at my stomach. I had to figure a way out of this hell hole.

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