Damien went home shortly after breakfast. Tommy almost didn't want to let him go, and not even because of anything sexual, but because he really thought of Damien as a friend already. Mary Baker, Tommy's mother, explained a bit before he left that when her son was between episodes, he was pretty much a normal, innocent boy. It was while he had a flare up of his condition that he became incredibly lewd and horny, almost like another personality, but that otherwise he was a pretty normal 10 year old. he was homeschooled because of the unfortunate reality of what it would be like if he had a flare up at school, so without any other friends his age he really didn't get the chance to socialize much.

Before he left, though, Tommy reached up to him with adorable as hell grabby hands. At first Damien thought the cub just wanted a hug goodbye, but when he got down to embrace the cub, Tommy pushed his muzzle into his, and they shared a sudden deep kiss. Mrs Baker looked surprised by this, but didn't make any move to stop it. Damien was a bit flustered, but hugged the boy back and nuzzled him a little, promising to be back soon.

When Damien got home, he was surprised to see his mother sitting in the living room.

"Hello, sweetie, how did the babysitting job go?"

"W-well... I'm uh... I'm gonna keep being his babysitter."

"Oh, wonderful, sweetie. And Tommy? Did you manage to help him with his condition?"

"Uh, yeah. About that... you set this job up for me knowing what I'd have to do... why?"

"Because, sweetie, it's the least I could do for you, and it's the least I could do for Tommy's mother."

"W-what do you mean?"

"Well, a while back, when I was first starting to understand that you were interested in younger boys, I spoke with Tommy's mother. She is very kind, and was concerned that Tommy's condition was getting more prominent as he got older, and needed a friend willing to help with his flare ups."

"Wait, you knew?!"

With a bit of a smirk, his mother patted the couch next to her for him to sit down, "honestly son, you might think you are clever about it, but you do know how easy it is to figure out from someone's search history what they are into, don't you?"

Damien's jaw dropped. His mother giggled, and continued.

"And you are far from the only fur with those interests. It's actually pretty common, and not that unusual. Sure there are rules in society, but those are to protect cubs from being hurt by those that want to cause harm and control, not those that love. Nobody in this arrangement is getting hurt. Plus, it's a great way for you to burn off steam as well. I know first hand how hard Tommy can go sometimes."

"I, wha, wait, WHAT!?"

"Well, I am Tommy's pediatrician, honey. You didn't think I got to have an intimate knowledge of his condition by just looking at his charts and notes did you? Plus, where do you think you got it from."

"Holy fuck, mom." Damien could believe what he was hearing: his mom was into cubs too.

"Now, language. We are adults talking about adult matters, and we will speak like adults. Am I clear?"

"Y-yes, ma'am."

"Good boy. Now, we do need to have a bit of a chat about your new client. I have no issue with you having sex with Tommy, as you have seen he needs it. However, he is a 10 year old, and he doesn't understand a lot of the complexities of it. I do get that you have urges too, but outside of an episode, where he's not quite himself, being too sexual can actually do more harm than good. If he starts developing sexual urges during the everyday, that's great, but please don't try and pleasure him into things. There is a difference between the capacity to have a loving relationship with cubs and being a predator: I have had a lot more experience managing my urges, and you have to make sure you don't lose control. I trust you have a legitimate attraction and love for boys, and that you don't actually want to hurt them, yes?" The matter-of-fact, clinical way his mother was speaking was nothing new to Damien, she was a doctor after all, but the subject was so casual and... understanding.

"Of course not! He's... He's a sweet little guy. I would never do anything to hurt him. He is so nice, fun, really smart and..." Damien sat and thought for a moment, "...He was really scared I was going to leave, he's been rejected a lot. I can't imagine how hard this is on him. I wouldn't want to make him cry, ever."

"It is hard, but you'll be good for him. You have a good head on your shoulders. Just be gentle, and make sure you listen to him."

"Of course I will."

"Good boy. Now, if you don't have any other questions, I'd like to relax a bit. I was up rather late myself at the clinic, we had a couple emergency cases that were rather draining. And before you ask; no. I have never touched you, I promise."

"Right, yeah, I'm just, I'll be in my room." Damien was almost starting to get dizzy from the subject.

"Alright, sweetie, and thank you again for taking the job. It means a lot to both me and Tommy's mom."

"Yeah, no problem… Anytime." Damien headed upstairs, his mind reeling. Not only did his mother know about his interest in cubs, but she had an active sex life with them as well, and was actively trying to hook him up with one. What a day. He flopped down onto his bed, his mind naturally wandering to his time with Tommy, the way the fox had clung to him, the way his cock had felt in the boy's ass, the way his hole had clung to his cock. He felt his dick begin to harden in his pants, and slipped a hand under his waistband.

He pictured Tommy, naked, legs spread, begging to be fucked, his massive cubhood dripping with precum, and the wolf started to stroke himself, slowly. He imagined his tongue dragging over the boy's tight pink hole, his fingers teasing the sensitive skin of his taint, making the boy whimper and moan, and his cock twitched in his hand.

The wolf sped up his strokes, his mind filled with thoughts of the little fox, the way he'd pant, the way he'd beg, the way he whimpered when he came, his massive cock shooting onto the couch. He could feel his balls start to draw up, and his mind began to wonder if his mother had done anything similar to the little boy.

He wondered if Tommy was ever naked in his mom's office, suffering through an episode, and what his mother's reaction was when she found the little boy's tight, pink, needy hole, or how her pussy must have gotten soaking wet when she heard her patient whimpering as she pressed her tongue against him. 

His balls clenched, and he moaned as he came into his hand, his seed pumping out and coating his paw and his belly. As his orgasm faded, he sighed, and knew that while that had helped to clear his head a bit, it was going to take some time for him to wrap his head around everything that had happened, and everything his mother had said.

***

Meanwhile, at the little fox's house, he and his mother were also discussing the situation.

"I'm glad you enjoyed your time with Damien, sweetie." Mrs. Baker was affectionately petting her son's head, smoothing out his always wild head fur.

"Mmhmm, he took real good care of me, mommy." Tommy replied, nuzzling against the calming touch.

"Good. I'm also glad he seems willing to help you, and didn't run away."

"Yeah. I really like him... Is it ok that I want him to kiss me?"

"Of course. He is a very handsome boy, and very caring, and he will help you through your episodes."

"Can I do a sleepover with him sometime, at his house, mommy?" The little boy's voice carried with it a lot of excitement, more so than Mary had heard in a long time when it came to a friend,

"Maybe, sweetie. We will see. Now, I have a few errands to run, but I will see you later, ok? Your father is in his office if you need him."

"Ok mommy." Tommy walked into the living room, and curled up on the couch, his tail wrapping around him, and he watched TV.

After a while, his father came out of his office.

"Hey kiddo, what are you watching?"

"Dunno." There was some cartoon on, but the boy wasn't paying too much attention, more just staring at the screen and he thought about last night.

"Hmm, well, have you eaten?"

"Yeah, mom made breakfast."

"Good, good."

Tommy's father, James, had known about his son's condition since the day it presented itself, and he wasn't ashamed of it, or even bothered by it, but it was difficult. When the little boy would go into his episodes, he'd be lewd and horny, and be in so much pain if he didn't get the release he needed. But when he wasn't, he was his normal, cheerful, curious self. He was a sweet kid, and James loved him more than anything. He was happy that it seemed that they found someone  else that could love him as well.

The fox's father sat down next to him, and turned the channel.

"Why don't we watch this together, huh?" James said, putting on a wildlife documentary, something that his son did really enjoy.

"Sure daddy."

Tommy scooted closer, and the two watched TV, cuddling and enjoying their time together.

After a couple hours, they both started to get hungry, so they headed into the kitchen to make some lunch. They decided on sandwiches, and as they worked, James spoke up.

"So, now that you have had time to think about everything, how did your babysitting go last night?" James and his wife had made it a point to parent their son with the expectation and assumption of competence. Not ‘gentle parenting’ per say: honestly they spoiled him, but they made it a point to encourage and foster logical thought. The boy was sort of forced into an early maturity with his condition, so they made sure he could think things through and understand complex things as much as possible.

"Oh, it was... fun. Damien is really nice."

"Yeah? Did he take good care of you?"

"Mmhmm."

"Good. I'm glad you're happy."

"Me too, daddy."

James had no issue with his son's condition, and would have been fine with him having a physical relationship with a partner, but he did have a concern about the whole thing. He was worried the boy was going to grow too attached, and that if the relationship ended, he'd be crushed. So far, though, Tommy had seemed pretty nonchalant about it, but his wife had assured him that the boy was just happy to have someone who understood, and was able to help him, and wasn't going to let him go. He just hoped that Damien wouldn't close off suddenly after already opening up this much to his baby boy.

***

"Mike, dude, it was crazy." Damien had walked down to the neighborhood playground to meet up with his friend, to vent and process everything that happened over the last day. The boys were sitting on the swings, casually kicking back and forth, if anything to fidget a bit as they talked. Nobody was around so they were able to talk freely.

"So, you like, fucked the kid?"

"Well, technically, yeah." Damien said, blushing.

"What was it like?"

"Didn't you want me to spare the details?" the wolf teased, batting his friend playfully on the shoulder.

"Well, not now. I'm invested." The bear said with a chuckle.

"Dude?"

"C'mon, give a guy a break. I just like it when my friends get to live their dreams... So what was it like?" Mike had always been understanding about Damiens preferences. He was a weird sort of guy, had a sort of shitty home life, but not the worst. His parents just didnt care what he did. They were abusive, but very distant. It led to a carefree attitude developing in Mike as well, to where as far as he saw it, as long as you weren't hurting anyone and everyone was cool with it, do whatever you want. Back when he ‘came out’ to him, the only concern the bear had was that Damien was saying he was a rapist. Once he cleared up those fears, it was just the same to Mike as if his friend said he liked taller girls.

"Well, he had a flare up while we were sitting on the couch, and started to get really horny. I pawed him off, and then he sucked me. He needed more, so I used my fingers, and then... he said he needed my dick. he was tight, but not TOO tight, but he was... god, Mike, the way his ass milked my cock. Like, it was amazing."

"Holy shit, man" The bear shifted in his seat, the slightest of tents forming in his jeans. He might not have been into cubs himself, but how could you NOT find this a little hot?

"And then after, we took a bath, and I got him cleaned up, and then we cuddled, fell asleep, and then this morning, his mom thanked me."

"For fucking her son?"

"No, not exactly, more for not bailing." Damien looked off into the distance for a moment, remembering the looks of past rejection on the little guy's face. "He's had a lot of people run out on him. He doesn't really have any friends his age because he's homeschooled, and most everyone that watches him bails because they can't handle his condition. It's really not just the sex that makes me like him, Mike. I legit think the kid is sweet, nice, and really cool. He's also fairly mature for his age, but that's probably the trauma."

"Man, you're so lucky. I can't believe your mom set that up."

"You're telling me. And about that... So my mom kinda outed me? Not to anyone else, but like, she told me she knows I'm into cubs."

"Woah, no shit?"

"I know! She told me not to worry about it, and that she's glad I'm helping the kid, but holy fuck, dude, she told me she's the same way."

"Woah, so, wait, does that mean she's fucked the kid? her other patients?"

"I don't know, she didn't say anything about others, but she implied she had with Tommy."

"Wow. Dude. That's wild."

"I know." Damien feld the air shift a bit. Talking everything out let him feel how strange this all was. And weirdly, how perfect.

"So, what now?"

"Well, his mom said since the kid likes me, and I'm not a wuss about everything, she wants me to babysit again."

"You're the luckiest fucker in the world." Damien couldn't help but notice that his friend's paw was not more firmly over the now not-so-small tent in his jeans.

"Mike… You good over there buddy?"

"What, I'm not gonna do anything, I just... can't help it. You're describing this hot little boy, and... c'mon, cut me some slack. It's not like I'm gonna jerk off right here."

Damien smirked a bit. "Well, no, not RIGHT here."

Mike chuckled.

"Seriously, though, I can... you know... help with that, if you want." The two weren't complete strangers to sexual contact, but didn't make it a big habit. They were teenagers, after all, and hormones were raging. Usually when it got like that, they would paw off to a porno together, and sometimes do each other.

"Dude, yeah, but not here."

"I know." Damien's eyes and head gestured to the nearby play structure where there was a small, covered area, with a hole at the bottom to make a little fort. The playground was completely deserted right now, it started to get a little cloudy with the possibility of rain soon, so they hadn't seen a soul except for the two of them. The two exchanged glances, and headed over, and slid into the little tube.

They didn't have to say a word. Mike leaned against the back of the interior play tunnel, his legs splayed open, and his dick tenting his jeans, and Damien crawled between them, and unzipped his friend's jeans, pulling out the large bear's cock.

"Fuck, I always forget you're this big." Damien said as his hand wrapped around the thick member. It was a solid 6.5 inches long and had to be easily that much around.

"Yeah, so I'm told." Mike replied, his breath heavy with anticipation. "More to work with than your new little boy toy's cub cock, huh?"

"Ah, yeah, I forgot to mention... he's almost as big as me" Damien slipped in before leaning down and taking his friend into his mouth. He wasn't a pro by any means, but having given and gotten enough blow jobs in the last few years from various flings he knew what he was doing. His tongue ran along the underside of the bear's dick as he bobbed his head, and he could hear him try and stifle a moan.

"Fuck, dude." Mike panted. "He's really that big?"

"Mmhmm." The wolf hummed around the bear, who couldn't hold back the moan this time.

"Ahhn, fuck. Well, I bet he can't do what you're doing with your tongue."

Damien continued working, his hands on the bear's thighs as he bobbed his head, taking more and more of his friend into his muzzle, until the tip hit the back of his throat, causing the wolf to gag slightly. He backed off, and took a moment to catch his breath.

"I mean, he does already know how to suck cock, I didn’t even have to teach him."

"Holy shit, that's hot."

"Mmhmm, it was amazing." The wolf went back to licking the bear's dick, knowing from experience he didn't need it fully in someone's mouth to cum. He just needed someone to play with the ridge of his dick, his sweet spot, so he continued to work his friend up between licks. "He was so… desperate, Mike. I didn't… even get my dick out… before he was on it, his… little muzzle trying to… suck me off right through my… boxers."

Mike groaned, and his paw went to the back of the wolf's head, encouraging him. "Fuck, dude, please, dont stop."

Damien chuckled, and his tongue worked the bear's cock, lapping up the now constant stream of pre coming from it.

"And, ahhhh, what about... his ass?" Mike felt his orgasm building, he just needed a little more…

"It was... fucking heaven, man... You would not believe… He was begging for it… his hole was tight, but it was like... made for me."

"Fuuuck." The bear moaned as his hips bucked, pushing the tip of his cock against the back of the wolf's throat. "Dami, I'm... gonna..."

"Mmhmm." The boy hummed in approval around the bear's dick, and with a growl, Mike came, his seed shooting down Damiens the boy's throat, who swallowed every drop, and licked his friend clean as the bear shuddered, and the last few drops dripped from his tip.

Damien sat back and wiped his mouth with the back of his hand. "So, better?"

"Yeah, thanks, dude." Mike tucked his cock away and zipped up his pants.

"You SURE you aren't into cubs, bud?"

"Shut up." Mike laughed and nudged the wolf. "You want me to return the favor?"

"Nah, I'm good... I’m actually still drained from last night and a jerk session this morning, let's head back. Maybe we can get something to eat, my treat."

"Oh shit, food paid for with cub fucking money? Sounds like a plan."

The two left the play structure, and headed towards the main part of town. 

"Hey, uh, Mike?" Damien started, cautiously.

"Yeah?"

"You're not... gonna tell anyone about Tommy, are you?"

"Nah, dude, I wouldn't. Don't worry, your secret's safe with me." Mike reassured his friend.

"Thanks, I figured I just, you know, wanna make sure. Not everyone is gonna be cool about this stuff like you."

"I get it."

The boys chatted casually as they walked, the subject quickly turning to video games to get their heads off just sex, and the newest Furry Fantasy that was about to come out. Neither of them had been able to stop thinking about it, but they both had it pre-ordered, and were hoping to get their paws on it later this week when it dropped. 

What they didn't see as they were leaving, however, was a dark, shadowed figure laying down flat on top of the playset.

A little while later, the two were seated at the local pizza parlor, munching on a couple slices and their conversation looped back to Tommy.

"So, how do you think I should proceed?" Damien asked, keeping his voice hushed, though with the chatter through the restaurant it was easy to mask their conversation.

"Well, the kid obviously likes you, so, just be yourself. It sounds like he's got a little crush on you, he’s cute, funny, and you can fuck him. What's not to like?"

"True, and his mom's totally fine with the whole thing, and seems to want us to hang out."

"Then, don't overthink it, man. Just enjoy it. You have a cute boy who wants to be around you, and you have a crush on him too, and his mom's cool. You wont hurt him, I trust that, just, go with it. You got nothing to lose. Like, as long as you blab to the wrong person, but…"

"Yeah, I guess. Thanks, Mike."

"No problem, man."

Damien couldn't believe everything that had happened in the last day, and he kept thinking about what the future held for him and the little fox. One thing was for sure, his life would never be boring.

***

As for the fox himself, he had spent most of the day watching TV, or playing video games, and occasionally thinking about Damien. Eventually his dad had to go back to work in his office and his mom was doing chores around the house, so he kept to himself. They give him a lot of free time, because he's pretty good about not getting into trouble. He also knows they feel bad for him, but he doesn't mind.

Tommy wondered if his friend had had a good time the night before, and when he was going to babysit again, and when he could see him again. He hadn't had any more flare ups since last night, which was nice, because that means Damien did a good job of draining him. Sometimes he will have small ones after a big one like that, but so far he was fine.

 The little fox was just watching some TV, when his mom came into the room.

"Sweetie, do you mind if I talk to you?" 

"Sure, mommy, what is it?"

She sat down next to him and gave him a hug. "Honey, I know you enjoyed your time with Damien, right?"

"I really like him, Mommy. He took good care of me."

"That's great, sweetie, but there's another reason why I want to talk to you. Tommy, did you have fun with him outside of when he helped with your episode?"

"Mmhmm."

"And does it feel nice to have someone closer to your own age who understands your condition and can take care of you when you need it?"

"Yea, it's great."

"And he seems like he is gonna be a really good friend, doesn't he? You want to spend time with him, and he wants to spend time with you?"

"I think so."

She seemed to struggle with the words for a moment. "Tommy, honey, I know how much you like him, and... he's a sweet boy. He's smart, he's nice, and I can see why… If you really like him, and with what you were saying about wanting to kiss him and if you think you might love him: If you wanted, then I wouldn't mind if the two of you... dated."

"Dated?" Tommy was surprised, though a lot of the time they speak frankly about serious subjects when needed, there was a blanket of euphemism and playfulness about his condition and more grown up topics to keep him from being super uncomfortable. Not that he couldn’t handle it.

"Yes, sweetie. Damien is a very special boy, and he's good for you. I can tell. If you want, I wouldn't mind if he were your boyfriend."

"Well… I would need to talk to him about that."

"Well, yes, but I'd be ok with it, if that's what you wanted. Would you want that, Tommy?"

"Maybe... I need to know him a little longer right? But I think I would like that."

"Well, that's all I wanted to know, sweetie. It's up to you. Ok? He's a bit older than you, so we might have to work some things out, and might have to be carefull, but I understand how things are, and I think I can trust him."

"Ok, mommy."

She gave him a kiss on the cheek and left him to watch TV, and the fox was left thinking about what she had said. He hadn't really thought about it like that, but she was right. Damien WAS nice, and he really did like the wolf. He was nice, and the two of them had a lot of fun together, and Tommy really wanted to see him again so he could talk to him about this.

Tommy hoped that Damien would come babysit him again soon.