Ding Dong! The door to a suburban, two-storey home slowly opens. “Oh, it's you, Jack! Come on in!” A male raccoon with light gray fur stands at the door, allowing a somewhat shorter purple squirrel to walk inside. “Of course it's me, what did you expect?” Jack said, playfully pretending to sound annoyed. “I've got some pizza bagels made for our little get-together, and the Pretendo 69 is set up, too.” Jack nodded and scurried inside. He always looked forward to spending the night at Robin's house. Snacks, video games, anything you'd want for a weekend at a friend's house. The two boys headed upstairs, to a second living room of sorts, full of three-decade's old period pieces. Chief among them was an old TV with an even older game console plugged into it. Racks of dusty CDs lined either side of the beige cabinets, the black bulbous box and dark gray machine plugged into it sticking out surprisingly nicely. “Any others coming?” “No, Jack, afraid not.” The older male shook his head softly. “You know they're usually not interested in this kind of stuff anyway. Besides, I kind of like it when there's only two or three of us here anyway.” Robin flicked the console's power switch. Nothing happened. “Need me to get the cotton swabs and alcohol again?” Jack knew what the problem was. Sometimes these old games just don't wanna boot up. Robin of course nodded; his buddy knew his way around electronics better than he did. Soon he put the game back into the cartdrige slot, and turned it on. Normally, a typical game of Plumber Party would result in a typical group of four friends fighting, arguing, throwing food at each other, maybe even a broken controller if things got out of hand. But, tonight was obviously a bit different. The night was more relaxed, with fair competition between the two teens. Robin might not have the hardware smarts his squirrel friend had, but he sure made up for it by being somewhat better at this game than Jack. “Well played, well played.” The squirrel's tail twitches and he adjusts his shirt collar. “Thank you very much, now if you'll excuse me, I'll happily take the last pizza bagel.” Robin reaches in for the last snack with his black-furred paw. A white-furred paw lands there first, however. He holds the tasty treat above the raccoon's head “Jack, that's mine!” The squirrel laughed at him. Clearly he was just messing around with him. He gives the older male the bagel. “I know it's yours.” He sticks his tongue at him and flicks his bushy tail. “You better, mister.” The raccoon takes a bite out of the snack. He then licks his chops, and tosses the plate in the garbage can. “Of course. Mister.” Jack sticks his tongue out at Robin again. … Later in the night, the boys went though things in the room Robin's older brother used to live in. Back when he was around, he used to bring all of his friends up to the second floor for weekend gatherings, with some guests even staying over for the night. He has since gone off to university, and the younger brother wanted to have similar gatherings just like his older sibling. However, they weren't usually as successful, and in many cases, as was tonight, Jack would even be the only guest Robin would host. “Your brother did teach you everything you needed to know about partying, didn't he?” Jack said, as they looked through the dressers in the large, abandoned room, hoping to find something interesting. “Yes, he did.” Robin replied happily. “What kind of food and drinks to get, the kind of music that gets the guests dancing, and even sexual aspects.” The raccoon blushed through a whole face of fur. His older bro was indeed quite the horndog it seemed, having amasssed nice collection of sexual paraphernalia in his time. Plugs, dildos, harnesses, whips, handcuffs, and even some vibrators. “There's no way my own mom would let me keep any of this at my house.” Jack picked up a dildo. It was shaped like an anthro horses' penis, though with minimal flaring. Perhaps to make it easier to insert? “Neither would mine.” Robin scratched his chin as he looked through an old magazine. “But my brother, he knew of places to hide all this stuff. I didn't even know about it until I walked in on him once.” “Oh, right. How could I forget.” Jack scratched the back of his fuzzy squirrel head. “Didn't you say your first time was with him too?” “It was, I actually topped then, too.” Robin gave his friend a toothy grin. “I still feel kind of bad about you not wanting to cum in me the first time we...had...sex?” Jack blushed, while clutching a magic wand vibrator. “Jack, you know I didn't want to get you pregnant. I'm sure you don't want to get pregnant either.” “Of course not.” Jack twiddles his thumbs. “Say, after our nighttime showers, do you want to...try stuff?” Robin grinned! He always liked it when Jack wanted to do sexual things. They weren't lovers, just friends. But that did not stop them from having sex sometimes. “First, I think we need to hide all this stuff again though!” Robin quickly gathered all the dildos and shoved them into a drawer. Jack stops for a moment, looking at a small chrome bullet vibrator. He puts it in his shirt pocket before helping Robin out. They head downstairs, as the cell phone reception was just better. Jack called his mom while Robin poured a nice glass of cola for himself, and some flavored water for his friend. “Okay, I'll see you tomorrow night. Goodbye.” Jack hangs the phone up. “No change in plans, I'm here to stay!” “Great!” “I figured they won't change, but you never know.” Jack was right, sometimes parents could change their mind at an instant. “If you don't mind telling me, what do you have in mind tonight?” Robin knew this wasn't the best time to ask, but otherwise he wouldn't remember. Nevertheless, that didn't matter; Jack whispered into his ear, the raccoon blushing. “Y-you want something for your film stash?” He knew, thanks to him, Jack had a nice porn stash on his hard drive. But this was news to him. “Of course, maybe a few other things too. Like...No, not down here. We'll talk about it upstairs.” Robin nodded. “Of course.” … While Robin was taking his shower, Jack pulls his tablet out of his backpack, and sets it up on a tripod, screen facing towards the bed. Robin emerges from the shower, his towel wrapped around the lower part of his body. The lean, fit raccoon male, about a year and a half older than the squirrel, noticed the setup almost immediately. “You weren't kidding when you said you wanted to film stuff for your stash!” Robin's eyes shot open wide, he even set up his bedroom's light in such a way where it would make it look good on camera. “Here” Jack opens a folder on the tablet, and gives it to Robin. “While I'm showering, you can look through this.” “...Okay?” Jack already left for the shower. Someone's clearly eager to get started. Curious, Robin looks through some of the photos and videos. He taps on one image. It was of Jack's lower half, presumably laying on the futon. He's moved his tail out of the way, showing off his aroused slit. There were plenty of images just like it, from different angles, even a few videos of him masturbating for the camera. As the raccoon scrolled through a few pictures, he'd lay out some of his own sex toys. Unlike the one's his brother used, Robin never really used them a whole lot. He was more interested in topping, naturally. He manages to get his favorite dildo out, a knotted one, when Jack enters the room. Jack drops the towel, and smugly grins. His expression still holds a hint of meekness, but he relished in seeing his friend find his somewhat less toned body worth having an erection to. “I take it you like what you're seeing.” The tablet was playing a video of him having an orgasm. “Yes, actually. I do. I can see why you wanted to wait to try buttstuffs for the first time, though.” Robin's erection was rock-hard. The uncut cock was twitching out of its fuzzy sheath. “Mmmhm, yes, I did...put a finger in there once, but I found it to not be that comfortable.” Jack's ears flatten. He'd see other boys, boys with different parts than him, they'd take things in their ass all the time. “I take it you didn't have lube at the time?” Robin says, as he puts some on the canid-style dildo. “Never have used it. Never felt a need to buy it.” Jack blushes, back to his meek self again. He examines the other toy on the bed, wondering how different it would feel compared to something being in his front hole. Robin gets set up for the camera, spreading his tail hole and showing his back sack for the camera, Jack taking photos of him each time he changed position. “Are you ready to see this? I don't normally take these, so if I'm going to slow, let me know.” “No! Of course you can insert it slowly. It looks better on camera anyway.” Jack hits record on the tablet, the video now rolling. The canid dildo is set down on the bed, the male raccoon straddling it from the front, gasping as he slowly insets it. “There, so far so good, Robin” Jack felt himself getting tingly between his legs. He'd never seen him try to take anything up his rear end before, but it was clear this wasn't his first time. As he pushed it to the knot, he gently thrust the silicone toy in and out of him. “Hmm that's nice!” Clearly Jack was turned on by this. “Now insert the knot” Robin nodded. He lifted his large tail and his cock and balls out of the way, as Jack zoomed in on the toy spreading the raccoon's ass nice and wide. After a groan from the older male, the knot sets itself in with a “pop.” “Ahhh! It's big!” Robin squirmmed “it's so big!” Jack turns the video off, and sets the camera's photo timer on. He reaches him from behind, his soft, white-furred paws moving Robin's fuzzy nuts out of the way and gently pulling back on his sensitive foreskin. “Uhhh Jack?” Robin raised an eyebrow after the pics were taken. “Yes?” “He smirks smugly. “Please get this out of me.” The toy, when knotted was too much for his comfort. “Sure.” The squirrel gently pulls the canid toy out of his butt. His ass was sore, and the hole itself spread. “How did that feel?” Jack's tail twitches and flicks, he's excited to have his turn. “I think I will top instead.” The boys have a nice laugh. “Well, you'll get your chance now.” The squirrel twtittles his thumbs again. “It won't hurt too much, would it?” “No, it shouldn't I suspect you'll be much tighter than me, but that won't be a problem.” Jack lays on his back, the camera positioned ontop of his lower extremities, and off to the side so he wouldn't knock it over with his tail. “Now.” Robin looked at him in the eye, putting lube on his fingers. “I know you're excited, but just relax for me, okay?” The older male puts the camera on video, and his squirrel friend nods, taking a deep breath, and spreading his legs. He moans at the sensation of cold, lubed didgets spreading his wrong hole for the first time. The mostly undisturbed area finally getting gently spread apart by wet, cold fingers. “Are you doing okay?” “Yes, you can get the plug ready now.” Indeed it was a rather modest buttplug. Tapered at one end and flared at the other. It too was covered in a layer of lubricant, and was ready to be inserted into him. Robin gently pushed the plug into his friend's ass. Instinctively, the squirrel pushed it out, not used to having any foreign objects inserted in there. “Easy now, Jack.” Robin put a paw on the squirrel's slightly pudgy belly, helping him calm down as it got deeper...and wider....and just like that, it was in. “Hmmm, this...it feels new.” He was a relaxed rodent by now, his anus having gotten used to the object being there. Robin gently tugged on the plug, occasionally taking it out and re inserting it to get the andromorph used to the motion of having something in the wrong place. Suddenly, Jack feels a paw get close to his clit. The sudden feeling of having his genitals rubbed caused him to clench around the toy. Robin then pulled on the toy as Jack was clenching around it. “A-Ahh!” Jack's face filled with color, being toyed with back there was a real turn on for him it seemed. “Oh, so you do like it?” Robin teased him. “Maybe tonight you'll be ready for the real thing” “Y-Yes! I...actually, can we stop for a moment? “Sure.” Robin pulls the plug out of the squirrel's anus. Jack gets up and switches the camera off, looking through the footage. “Well, that's...what I was getting at. You see, I still feel kind of bad you didn't get to...heh...creampie me on my first time. I'll admit that that was my big reason to have...anal.” “So, you think you're ready for it? Already?” “Robin, it will be just like when you deflowered me. It will turn out fine.” “Well you seem confident.” Jack turns the camera back on and puts lube on the raccoon's dick, putting him in a laying-down position. He then straddles him, his body upright, his front side facing the camera, showing off his arousal for the camera. Robin lifts the squirrel's tail again to help prep the opening one more time. It was still super tight, but more than lubed enough to at least try it. “Okay, remember, just relax.” Robin sighed and gently inserted the tip of his cock into the younger boy's anus. Jack gasps and mildly yips, but is still able to relax, his opening slowly accommodating an inch at a time. Three inches Four inches Five inches Soon, all six inches. “Jack, are you okay? You seem stunned. “I'm fine, please, can we continue?” The younger boy's coochie flushes with color and glistens with arousal with the raccoons whole length in him. In the wrong hole, no less. Robin nods, and slowly thrusts in and out of him. They both gasp at the new sensations, the new feelings they both were experiencing. The raccoon wraps his paws around the young squirrel's hindquarters, and around his hips, gripping his soft fur. “Huff-, if you need me to stop, please let me know.” He grabs the squirrel by his flanks, keeping him upright while he thrusts in and out of his tight ass. Every small thrust he makes, he lets a soft moan out. One of those paws makes its way to the squirrel's pussy. Sensitive and having become harder to ignore, the raccoon starts by rubbing the area just above Jack's sensitive clit. “Ahhh!” By instinct, he once again tenses up, as being sexually stimulated would do. Before he could have any chance of getting close to climaxing however, Robin suddenly pulls out. “Hehe, I hate to ruin our fun, but I need this to be more comfortable for me, Jack.” “Oh, that's fine I guess.” Jack nodded, a bit disappointed he wanted to stop. Robin re-arranges some pillows so he could sit upright. He holds Jack just above his lap, and spreads his legs, holding him up with his thighs. The older boy then gently slips his penis back into the squirrel's ass, making sure he did not hurt him. This time, it went a lot more smoothly; even with an arousal he had no issues taking it in him. Within moments, Robin thrusts up and down, placing a finger on Jack's clit, rubbing it gently with each thrust. “Yes, ahh, right there” Jack says as he is then fingered and spread by the raccoon. He was clearly in bliss. The feeling of being dominated was one he always craved, where he's not in control. Robin meanwhile would buck his hips into the needy squirrel, his tight ass squeezing around his cock, stroking it with every thrust he'd make. At some point, they'd both need to cum. “Yes, please, I'm getting close!” Jack tenses up quite a bit before he releases. His pussy and ass release and contract as he breathes heavily in sync with each one. Already fairly close to cumming as well, the squirrel's orgasmic contractions clamp and release his sensitive dick, ultimately proving to be too much to finally keep in. He ejaculates full force into the squirrel's wrong hole, the raccoon more than willing to make up for not cumming in Jack before. Each squirt proved to tire Robin out further, until he finally ran out of cum to fill him with. He gently sets Jack down on his lap, and sighs deeply. Jack then pulls off of the spent raccoon, still panting from having a particularly hard orgasm. He turns around for the camera, showing off his exhausted pussy and sore ass. He spreads his tailhole, keen to show the present Robin left him in there. Cum drips out of his ass, trailing down the insides of his thighs. Having finally had plenty of new material for his porn folder, he turns the camera off and puts the tablet and tripod back into his backpack. “Robin” Jack waves a paw infront of his face “wh-wha?” “What? I had fun! I got lots of stuff for my folder. You wore yourself out!” Jack's tail twitched excitedly. “Jack, you'd understand if you had different...parts.” Of course, the concept of refractory periods was not one the squirrel fully understood. “I'm pretty wiped out too.” Indeed he was still breathing fairly heavily, even though his orgasm already ended. “But at least I don't feel like going straight to bed!” He wipes the sweat off his fluffy forehead. “I might fall asleep right here. You can play some video games or something if you'd like.” Robin slowly began drifting off to sleep as Jack put some of his clothes back on. The smell of sex, and an orgasm harder than even Jack's was simply too much for him to handle. Jack pulled the covers over his body. He then kissed him on the lips. “D-did you just?!” Robin woke up, clearly annoyed. “Oh, come now, we just had vigorous sex, and you're complaining about a kiss? They do that even in G-rated movies!” Jack gave him a most innocent looking face, sticking his tongue out at him...again. The raccoon groaned before flopping back into the pile of sweat-drenched pillows. “Fine. You have a point, friends don't usually have vigorous sex.” Jack then left the room, with his backpack with him. He pulls out the tablet, sets it back up on its tripod, and sorts through the folder. He opens the last file. The 55-minute sex tape where he has anal sex for the first time. The time where he had one of the most intense orgasms he'd ever had, and yet somehow his not-boyfriend ended up more worn out than him. In fact, he still wasn't quite finished after filming that. He reaches into his pants pocket. “I wanna try this thing out at least once before my mom finds it.” He takes his clothes off again. And he switches on the chrome bullet vibrator he had swiped earlier.