Slowly, gradually, the level of socializing on the street picked up. Connor got taken to few different houses by one of more of his girls. Always on a leash, of course. He got to meet other boys and demonesses that way, and of course get fucked by the latter. He gathered that over half of them liked to fuck boys in their natural demon form, while plenty of others either alternated, or like Lita stayed mostly in human futa shape.
It was very fun getting to meet some of his peers, and get to experience yet more variations on getting stretched beyond all reason and pumped full of cum.
Even better than all that was when Lita and Monica finally convinced Demi that they should host a barbecue. The event being, as usual, an excuse to socialize and for boys to get pounded by a variety of cocks.
As part of the host team, Connor was already excited at being the ass of honour all day. It only got more thrilling when he discovered what Monica had set up for him.
"See, we get you all strapped in and lifted up, and you just have to stay there and take everything until we let you down," Monica explained.
Connor looked at the complicated series of straps and chains dangling from a solid tree branch in the yard. A tree he was certain hadn't been there the day before, even.
"How does it work?" he asked. "I can't even see how I'd get into it."
"Don't worry about it. I can handle that part. You in?"
Connor's heart beat harder at the promise of being all restrained and helpless all day, ass presumably on prime display and ready for using any way someone saw fit.
"Do you even need to ask?"
Monica grinned.
It turned out to be quite comfortable, actually. There were so many straps holding Connor that his weight was very nicely distributed.
Part of the complication of the whole setup was that he could be held in any number of different positions by careful and selective manipulation of various straps and chains. Once he was in, Monica played adjusting him many times until she had a good grasp of things.
Lita 'helped' by testing Connor out while he was hanging at various angles, legs and arms in different stages of spread wide, or held close and tight but out of the way.
They then had some fun with him by pushing him back and forth in his sex swing, teasing him by keeping their cocks just at the very edges of his arcs.
Connor was pretty sure he was going to spend the whole day hard and excited for more.
At least Lita actually lubed him up and fucked him before guests started arriving so that he was all ready for them. That was nice of her.
The rest of the day was basically a blur of taking cock after cock. He was both the only boy available for free use the whole time, and the only one suspended in the air, easily moved to any height or angle someone wanted. It made him a novelty on top of being such a smooth, supple, and willing cock holster.
Lots of other boys were brought around, and he got to talk and compare experiences with most of them, but that was only between getting fucked senseless or having his throat viciously filled. A game developed at some point of demonesses pairing up and taking him from both ends, trying to meet their cocks inside him. He had suspicions one of his girls was spurring on the friendly challenge, but it honestly didn't matter how it happened. The important thing was that he got fucked and filled over and over and over.
****
Monica kept an eye on Connor most of the day. She probably didn't need to worry about him. He was having the time of his life accepting every cock that came his way, either at his face or ass. Both at once, even, once she started suggesting it to some of her friends. The game of meeting in the middle was enough to amuse some, for reasons of sport or simply seeing what Connor could take.
He could take a lot. That was made very clear.
On occasion someone would get him to eat her ass or suck her balls or something, but mostly it was all cock all the time.
There were plenty of other little butt sluts around too. Monica helped herself to a few boys through the day, mostly taking their sloppy, gaping asses for a spin.
Once or twice she encouraged an eager boy to clean her up while she sat back and relaxed. They somehow universally took that to mean licking and sucking on her, despite her never saying anything of the sort. She grinned at their slutty, enthusiastic faces while chatting away with her friends, enjoying those wet, pink tongues all over her cock and balls.
The only thing Monica really needed to help Connor out with was to drain him every now and then. Not his balls, since he came regularly all on his own from getting railed by girls and demonesses. But he actually collected enough cum inside him to expand his tummy to dangerous levels, to the point where he was being pushed back and forth like a ball on a rope just to hear the sloshing in his belly.
It took several minutes each time for enough cum to pour of out of him that Monica could let everyone get back to it. The poor boy wouldn't be functional by the end of the day, but he undoubtedly would be pleased as could be about it. He only grinned dreamily at her when she came near, provided his mouth was currently unused.
"Mon?" Connor whispered to her once when he was able.
"Yes, little one?"
"Thank you."
Monica patted his head and made way for his ass to be filled once more.
****
Lita enjoyed herself in the beautiful sunny weather all day. She didn't get to fuck Connor much at all since he was so busy, and since even when he wasn't he was too stretched out for her.
She did, however, get to entertain herself chasing after newly arrived boys in games of tag that ended in fucking their butts. It wasn't much of a challenge until some other girls joined in, at which point it became a fiercer match of shoving one another away and trying to claim the prize first. All in good fun, of course. Hardly any serious injuries at all.
Lita went to sit with Demi or Monica sometimes when she wanted a break, curling up beside one or both of them for the security of their presence while she cat napped.
Later in the day, as everyone's energy waned from a fun day of hanging out and fucking, she was able to find some tired, well-used boys to curl up with on her frequent breaks. She would have liked to snuggle up with Connor for a proper siesta, but he didn't get any breaks, really. Plus it seemed so complicated getting him down from that swing Monica had him firmly strapped into.
She sometimes watched him bounce roughly around on other cocks, obviously having a grand old time with it, but there were other holes to fill, and time waits for no infernal being.
****
Demi padded up to Connor as evening broke and the last of the guests were slipping away, often having to carry the boys they'd brought with them.
"Still conscious?" she asked lightly.
Connor cracked an eye open. "What day is it?"
"Same day as when you went up."
"Oh. Then... probably."
"Would you like to get down?"
"Yes please. It's a nice swing, very snug and cozy, but I'm a bit sore."
Demi snorted. "A bit?"
"My everything hurts."
"Everything?"
"Everything. It doesn't really seem physically possible how many different parts of me I can feel aching."
"Well, you know, Hell and damnation. Physically possible is more a suggestion than a rule."
"Fair point." Connor sighed. "Seems a waste it'll all be good as new again tomorrow."
"You're such a little weirdo."
Demi considered the myriad of straps holding Connor in the air, then shook her head. She passed her hand along the length of his body, snapped her fingers, and smiled in rather petty glee as he fell in a heap to the ground.
"Ow," said Connor.
"So sorry."
Demi waited a moment, but he definitely didn't seem like he could move on his own, and she didn't have all night to wait around for him to recover.
Or, more to the point, she couldn't be bothered hanging around that long.
Demi bent down, scooped Connor into her arms, and marched him delicately into the house. He happily nuzzled at her while being carried along.
"How are you so heavy?" Demi grumbled. "How the fuck much cum did you take?"
"A lot. Mon drained it all out a few times."
"And you're still this swollen with it?"
"Yep."
"You slut."
Connor grinned lazily. "I know you only say mean things 'cause you love me."
"I'll drop you again."
"You'd have to pick me up again if you did that."
"Could just leave you."
"That wouldn't be nice."
"You're lucky we're here already," Demi said, nudging the bedroom door open with her foot, the carrying Connor in and depositing him summarily on the bed. "Get some sleep."
"M'not tired."
"Yeah, you look all full of energy."
Demi pulled the covers up and tucked them around Connor. "Get ready for more poundings tomorrow. I'm not gonna go easy on you just 'cause you had half the street running a train on you all day."
She turned to go.
"Demi?"
"Yeah?"
"You can cum in me, if you want. You look like you need to."
"Who says I need to?"
"You're all hard and dripping."
"So?"
"You don't have to be gentle with me just 'cause I'm tender right now. I can take it."
"Maybe I just don't feel like it, is all."
"You don't wanna hurt me. It's nice. But I didn't see you fucking anyone all day. You should cum. You'll sleep better."
Demi turned on Connor, glaring at him. It didn't faze him, though. It never did. He was frustrating that way.
"Do you know you're unquestionably the worst at being tortured?" she asked. "Just the absolute worst. I've never known anyone so bad at accepting a punishment."
"I'm very good at accepting it," Connor protested, rolling over and pulling his covers off. He wiggled his butt a little.
"Not like that. Bad at accepting that you're being punished, I mean. Like mentally coming to terms with it. Anyone else in your position I've ever worked with would be sobbing themselves to sleep right now, if they could think at all. You're here begging for more."
"You don't have to pretend all the time," Connor said, stifling a yawn. "It must get exhausting. Have a nice cum in me and we'll go to sleep, ok? You can berate some more in the morning."
Demi sighed and wished she could just walk away, but she really was horny. And, despite all his many, many faults, Connor was the only one she'd really considered fucking all day. All those other boys were as bad as he was, but with none of the rapport built up. The connection. Irritating as he was, Connor somehow grew on her after a time. He was a pain in the ass, but he was her pain in the ass. Hers, Monica's, and Lita's.
They were stuck with him indefinitely, and the more time they spent together, the harder Demi had to work to build up the same fury about it. It was getting to be comfortable in its own way. Maybe, just maybe, Connor wasn't the worst boy to be assigned to.
"A quick cum, then," she allowed, making sure to sound begrudging about it. "But then you're going to sleep, ok? No arguments."
"Just a quick one," Connor agreed. He struggled to lift his butt until Demi helped lift him up and he was able to get his knees under him. "It's sweet of you to not take advantage of any of the other boys," he said softly. "You didn't need to do that, though. I know you need to cum more often than that."
"They're more aggravating even than you are. Had nothing to do with you other than that." Demi tossed her hair as she climbed up behind Connor. "Just 'cause my sex drive runs high doesn't mean I 'need' anything. It's useful for my work. Doesn't mean anything else."
"But it's nice to cum more often," Connor insisted, wiggling his bum again.
"Yeah, well... maybe."
Demi ran her fingers over Connor's sloppy, messy, gaping butthole. There was so much cum everywhere that she didn't need to worry about any additional lube.
She didn't want to admit to him that she did, indeed, need to cum pretty badly or she'd spend a rather frustrated night. It didn't matter, though. He knew.
Demi thrust into Connor's ass, making him grunt and whimper softly. Even though he was tender and sore after a long day of taking cock and getting cummed in, he still pushed back against her, helping her get deeper inside.
There was hardly any resistance at all from his poor, overstretched bum. Demi was able to go balls deep in him quickly and relatively painlessly.
"I'm gonna pound you and cum deep in your messy ass," Demi warned softly.
Connor sighed contentedly. "I know."
Demi grabbed big handfuls of Connor's hips and butt, kept him spread wide for maximum penetration, and started fucking him.
Cum spurted back out of Connor on particularly hard thrusts, and he gave little whimpers from time to time. It bothered Demi just how cute she was starting to find some of the noises he made, and how adorably slutty he could be. He'd spent the whole day having his ass broken and was still enjoying having her pound him, even with how achy he clearly was.
She could have gone for hours on him if she wanted. Really drive home just how painful he was making things for himself. But it was late, and maybe... maybe she didn't really feel like doing that to him.
She was getting so damn soft on this boy. It wasn't natural.
Demi pounded Connor's ass long enough that she felt the point had been made, then allowed herself to cum. She hissed in pleasure as her balls pumped a long overdue load of thick, creamy cum into Connor's slutty boyhole.
Another trickle of cum leaked out of him as Demi pulled herself all the way free. His ass was so destroyed that if not for the nightly reset, she wasn't convinced he'd close back up properly for days. Weeks, maybe.
Demi rolled Connor onto his back and straddled him, slapping her sloppy cock on his face. "Clean me," she said.
She didn't need to bother. Connor already had his tongue out to start licking before she'd finished her brief sentence. He didn't have the mobility to do a particularly good job cleaning all the cum off her cock for her, but it was the principle of the thing that counted.
"Demi?" Connor asked between licks.
"Yeah?"
"Would you... stay in me tonight?"
"... with you?"
"No. In me."
"That's what I thought you said." Demi sighed and reached down to ruffle Connor's hair. "You won't be able to sleep at all, you know. If you have me inside you the whole time."
"I think maybe I won't be able to sleep without you. I'd feel too empty. I feel empty right now."
"Why are you so slutty?"
Connor grinned shyly up at Demi past her cock. "You bring out the best in me," he said in a near-whisper.
Demi loathed the sense of affection in her that made her agree. She rolled Connor on his side and slid back in, spooning him while balls deep in his slutty ass.
"Better?"
Connor nodded. "Yes, thanks." He snuggled back deeper against her tits. "You're so soft. And warm."
Demi wrapped her arms around him, hugging him to her. "You don't tell anyone about this," she warned.
"Pretty sure Mon and Lita already know."
"They don't know shit." Demi sighed. "No one outside this house, then."
"Promise." Connor sighed happily. "I'm so happy I ended up with you girls."
"I hate that I know you mean that."
"Thanks for being amazing to me. Love you."
Demi tried to muster some annoyance at the simple, genuine emotion expressed. But she couldn't. This boy had ruined her worse than anyone could ever ruin his ass.
"You're... not the worst," she whispered, keeping her voice low in case anyone else might hear.
She could feel the goofy smile on his face without even having to look.
Demi only got to lie there with Connor for a few minutes in silence before the door swung gently open. Demi groaned but refused to look up and show any guilt or shame at being caught like this.
"Well well," Monica purred. "Aren't you two cozy?"
"Tell anyone and I murder you in the face," Demi replied automatically.
"Perish the thought. Just came to check on our little one. Seems to be doing ok, though, doesn't he?"
Monica stalked silently over to the opposite side of the bed from Demi. Neither was the least bit surprised when Connor reached out for Monica and tried to pull her into bed as well. At least slightly surprising was how easily Monica let herself be dragged into the warm cuddle.
"You were a good boy today, weren't you?" Monica cooed to Connor.
"Don't encourage him," Demi said.
"Took so many cocks. You were just the sluttiest little thing," Monica continued, undeterred.
"What a magical fucking moment this is," Demi grumbled. "Only missing-"
"Hey!"
"-Lita."
Lita bounced in, pouting at the scene in the bed. "I was gonna come cuddle-fuck Connor! No fair!"
"Too slow," Demi said.
"I had things to do! That's... ugh. Not even any room for me. Rude!"
Despite her words, Lita clambered up on the bed, making everyone grunt a few times as she accidentally kneed or elbowed them before she finally settled. She cozied up right on top of Connor, the only place left she could cuddle with him, what with Demi on one side and Monica on the other.
"This'll do, I guess," Lita said, just before yawning loudly.
"So glad you could join us," Demi said.
Lita made a rude noise and otherwise ignored her.
****
Connor was warmer and snugglier than ever before. He hadn't anticipated this when he'd asked Demi to stay, but it was absolutely amazing that it was happening.
His three girls, all snuggled in a warm, loving ball surrounding him. Soft, lovely boobies pressing into him, one cock deep inside and two others gently poking him. Some tickling hairs on his skin, at least one twitching tail flicking against him, strong arms around his chest, and the overwhelming sense of love, protection, and belonging.
They'd had him going, at times. That he might actually have ended up in some kind of Hell. He felt silly for ever falling for that. There was no question. This was Heaven if ever there was one.
****
Epilogue: Sometime in the Future
****
Demi and Monica stood on the back deck, leaning against the railing, taking a slow smoke break. They watched the action in the yard with casual interest.
"S'nice seeing him with his friends," Monica commented.
Demi nodded distractedly as she exhaled smoke. "It is, I suppose."
Connor was mid play date. Which was to say he and two other boys from the street were face down, ass up on the lawn, positioned so they could talk easily with each other when they weren't getting pounded too hard.
Rayne and her colleagues had brought Jos over today, and Namila's crew from a ways down the road had come over with little Gabe.
Play dates had become fairly common over the years. Ever since that party they'd thrown, really. They gave everyone a chance to socialize and experience different cocks or buttholes, as the case may be.
Even as Demi and Monica just watched and smoked, all three boys were moaning incoherently as they all got their asses drilled deep. Everyone not fucking them at the moment was just kind of hanging out and taking it easy. Relaxing and sunbathing.
"You know his review's coming up," Monica said.
Demi blew out a more forceful puff of smoke. "I know."
"What do you want to do?"
"Push it back."
"We pushed it back last decade."
"I know."
"And the one before. And-"
"You want him going up for review?"
"No. We'd risk losing him."
"So why pester me about it?"
"Trying to see if you'll admit you don't want to lose him either."
Demi took a last drag and flicked her cigarette to the aether. "How would I ever get a chance to break him if he went somewhere else, hm?"
Monica rolled her eyes. "That excuse wore thin years and years ago. You still rolling with that?"
"What else do you want from me?"
"To admit you kinda like him."
"Maybe I do. So what?"
Monica grinned smugly. "Knew it."
"Yeah. Whatever. Every decade you think getting me to admit that's some kind of victory. Now who's wearing thin?"
Monica just grinned.
"You tell anyone-"
"I know, I know. Murder me in the face." Monica stubbed out her cigarette. "Haven't told anyone yet, have I?"
Lita came prancing up. "Hey, almost your turns again," she said in her bubbly voice she reserved for particularly good days of fucking boys.
Demi shook her head minutely. "Aren't you ever going to get out of that ridiculous form?"
Lita looked down at her cute human futa body. "Why? Connor likes me like this."
"Yeah, I bet he does. You can do whatever you want, you know. He doesn't get a say."
Lita shrugged. "Don't see why not? He's as much part of the family as any of us."
"We aren't a family."
Lita rolled her eyes. "Such a grump. How many years we gotta live together before you accept this, hm? Another fifty? A hundred?"
"She's coming around," Monica said. "She's old. Stuck in her ways."
Demi glared at the two of them. It had no effect whatsoever on their impertinence. "I miss the days when everyone screamed in fear at my approach," she grumbled sulkily.
"Yeah yeah. The good old days." Lita bounced impatiently, jiggling her cock in the process. "Are you gonna come fuck some boys or what?"
"Alright," Demi said. "We're coming."
Lita kept pace with them for the short walk to the well-fucked boys. "We pushing back review time again?"
Monica nodded happily. "Yep."
Lita smiled. "Good. I knew we would. Rayne and Namila are too. Most of the street, I think."
"Yeah, gee, that's not gonna look suspicious or anything," Demi muttered.
"We've been over this," Monica said. "No one wants to deal with this mess. We keep it handled, we've basically got free rein."
"That's the best kind of rein," Lita added.
Connor's ass was free, and Demi knelt down behind him, glad of an excuse to ignore her friends.
"You're all sloppy and gaping, huh?" Demi said, running her hands along Connor's messy ass cheeks.
Connor tried to look up at her, but he was a bit limp, the way he so often got after getting his ass railed for hours on end.
"Got my ass wrecked," he murmured. "It's been nice."
"Someday you're not gonna enjoy this so much."
"Nuh uh."
Demi rolled her eyes, but a small smile crept over her lips too. Without warning, she plunged her cock into Connor, going balls deep in one powerful thrust. He was very used to such moves by her, but still seemed to enjoy them every time.
"Heard my review's getting pushed back," Connor gasped when he was able to talk again.
Demi held herself deep inside him for a moment. "It is."
He smiled. "Thanks, Demi. You're the best."
"Shut up."
Connor only grinned wider. "Love you."
"... I'm not saying it back."
"That's ok. I know."
Lita bounced in front of Connor. "Come onnn Demi. You aren't even fucking him yet."
"Seriously? You want another turn already? How many centuries is it gonna take for you to calm down?"
"It feels good. Maybe I don't wanna get jaded and grumpy like you," Lita said, sticking her tongue out.
"You can fuck my mouth, if you want," Connor offered.
Lita looked around. "Guess your friends are nearly passed out, huh? Can't really talk to them anyway." She knelt down in front of Connor and had to help him get up on his arms. "You're a good boy, you know?" she said, patting Connor's head.
Connor nuzzled at Lita's cock. "You're all so good to me too. I love you all so much."
"Awww," Lita said with a faint blush. "Love you too, our little slutty boy."
"Is Monica there? She-"
"I heard," Monica said, fucking Jos next to them. "Ask him to please stop embarrassing us in front of everyone."
Lita nodded. "Mon says to please-"
"I heard," Connor said. He obediently opened wide and waited for Lita to shove her cock in. He wasn't waiting long.
Demi and Lita fucked Connor from both sides. They didn't bother being gentle. Not with Connor. They knew him too well for any of that.
Demi was unsurprised to feel his ass contracting and twitching around, signaling that he was cumming from their efforts. That seemed about right.
****
Connor was his usual floppy, sloppy, total mess of a boy by the day's end. Demi and Monica helped him into bed and tucked him in, then Lita read him a story. The latter would have been almost sickeningly sweet, except that Lita's stories were self-written, and generally so graphically sexual they could make a grown demoness blush.
Connor was soon fast asleep after his rather exhausting day, and being put so tenderly to bed. Demi and Monica each kissed his forehead before leaving him alone. Lita, however, snuggled right under the covers with him.
"We could stay too," Monica murmured as she and Demi padded out.
"Nah."
"He's good cuddles."
"I know. But Lita likes having him to herself sometimes."
Monica grinned and lightly nudged Demi with her elbow. "You're such a softie underneath it all, huh?"
"I am not."
"Are too."
Demi sighed. "You-"
"I won't tell."
"No. I was gonna ask if you wanna sleep together."
"What, like, you wanna fuck?"
"No. Actual sleep."
"Ha, you really are turning into a softie, huh?"
"... you want to or not?"
"Course I do."
Demi and Monica fell into bed together. They snuggled together under the covers.
"I mean, you didn't say it," Monica said, "but obviously no one hears about this."
"Yeah, no, obviously," Demi murmured back.
"This job's pretty great, huh? With Connor?"
"It has its moments."
Monica snorted. "Well I love it. And I know you do too."
"Maybe."
"Night, Demi."
"Mmm. Good night."