Reddit Confession - Backdoor Deal
Based off a Reddit Confession, Willa is a single mom struggling to make ends meet. When she is unable to afford a Christmas present for her son, she makes a deal with her younger and better off neighbour to get her son’s gift.
This is a work of fiction. Unless otherwise indicated, all the names, characters, businesses, places, events and incidents in this story are either the product of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are of legal and consenting age, likewise if you are reading this story, you should be of legal age in your respective country. All characters are my own creation, any resemblance to existing characters is purely coincidental and not intentional, please do not use them without permission. If you would like to use them in a story, please feel free to send me a PM. ********************************************************************************** These stories are based off of confessions people leave in the R/SluttyConfessions subreddit I find interesting enough to want to turn into a story. You can find the confession this story was inspired by here: https://www.reddit.com/r/SluttyConfessions/comments/1pvj44a/i\_36f\_had\_anal\_sex\_with\_my\_27m\_neighbor\_to\_get\_a/ ********************************************************************************** Life was tough as a single parent, especially around Christmas and birthdays. Even with working two and sometimes three jobs, Willa could never quite seem to come out ahead. The young tawny furred coyote was just barely scraping by and managing to pay her bills, along with her son’s school fees, there was hardly ever anything left over for herself, let alone luxuries. What made it worse was that her kid was so deserving of gifts and praise, he always did well in school and never gave her a hard time. Or at least, nowhere near as much as the average kid should, so she knew she had a good one. The older he got, the harder and more painful it became for Willa to accept her shortcomings. She knew she was doing everything she possibly could for the both of them, but it never quite seemed like enough. Especially lately, when Ethan started getting to the age where he really liked computers and video games but also programming and doing other stuff with them. It just seemed like something he could actually make a real career out of, so it was in her best interests to foster such a thing in her sons’ life. Willa had wanted to get him a new computer for a while; even though he had an older one already, but even she knew enough to know that it was not meant for gaming, it barely played Solitaire. But as usual, money was tight, despite her best efforts to I save up a little extra. Unfortunately, before she could save enough to purchase one on her own, computer prices had skyrocketed. Willa had put the purchasing of the system off until closer to Christmas, fully intending to roll Ethan’s birthday and Christmas gifts into one so she could get him something extra good. As she sat at her kitchen table late one night, with all her bills and accounts spread out before her on the kitchen table in a last desperate attempt to find some way to squeeze out the remaining money needed for her son’s gift, Willa sighed in resignation. There was just no way she could afford to get Ethan the gift he truly deserved, at least not in time for Christmas. She had already postponed it from his birthday months before; she couldn’t do that to him again. Just then she heard a familiar voice outside her window. It was her neighbour, Gregory the young buck, who she knew was some sort of a finance bro and who she also knew was relatively well off. Gregory hit on Willa all the time, but he had also helped her out in the past with other things too. Of course, she had been foolish and hooked up with him after he helped her out once, that had left the door open to a rather unprecedented relationship between them. “Hey Greg, got a minute?” Willa called out from her kitchen window. “For you, I have all the time in the world. Why don’t you come on over?” the admittedly handsome young buck offered. Judging by how he was dressed, he was either coming back from another MLM meeting, or a date. Either way, he looked like he had failed to get lucky, which would probably work in her favour. A few moments later, Willa was sitting on his sofa as he poured them both a glass of the latest expensive red wine he’d found. “So, what’s up, mamasita?” he asked in that painful way someone not from the culture often misused words and phrases they really shouldn’t. “I need a favour, a big one…” Willa began as she slowly turned the wineglass between her hands and stared down into the swirling red liquid. “Oh? What sort of help” Gregory asked with a grin, though she knew he probably already suspected what she was about to ask. “It’s almost Christmas and I promised him on his birthday, but I can’t afford to get Ethan the computer he wants…” the tawny furred coyote began to explain as she looked up at Gregory with her deep hazel eyes, while one of her hands brushed her long blond hair back behind an ear. “Oh, is that all?” the buck replied with a friendly smile and a reassuring pat on her knee. “But you know favours don’t come free” Gregory quickly followed up with, knowing she wouldn’t be put off or insulted by his advances. Hell, she had even traded him a blowjob once for some groceries, so this wasn’t anything new between them. “Well, what do you want in return for helping me?” Willa asked with a slight grin of her own, at least it seemed like he was open to negotiations. Truth be told, the buck was a good lay, so she didn’t really mind their arrangement. But being paid for sex did make her feel a certain way, but this was for her son, and she would do anything for him, so it was worth it. “Well, gaming computers aren’t cheap, so I’d need something special in return” the buck began slowly as he looked her over, as if gauging her reaction. “I think anal would be a good trade for a decent gaming rig, don’t you?” Gregory asked with barely restrained eagerness. Willa had to bite her tongue, she had only meant for him to help pay the gap in cost she was missing, not buy the whole thing! But Gregory had just offered to foot the bill and all she had to do was give up her butt for one evening? It wasn’t like she had never done anal before, granted it wasn’t her favourite, but it also wasn’t like she wouldn’t be giving up something precious like her virginity. At least this time, the guy doing her butt would be helping her out and not just using her to get his rocks off. “Have you ever done it before?” he asked carefully, when she didn’t respond right away. “Yeah, once…when I was in my twenties. It’s not for me” Willa replied honestly. She was hoping for something a bit easier, maybe even just to dress up like his favourite comic book character or something and let him fuck her brains out. That could actually be a lot of fun, she thought. “I only ask because I’ve never tried it, haven’t met anyone willing to let me try it either to be honest” Gregory replied almost nervously as he rubbed at the back of his neck. From past experience he knew most women weren’t so keen on even discussing, much less doing such things, some got rather defensive about it too. “Well, I’ll tell you what…if you get Ethan the gaming system he wants…you’ll get what you want too” Willa smiled as she reached out and gently caressed the shocked looking buck’s cheek. As they sat and drank their wine, Willa and Gregory hammered out the details and soon a plan was in place. The Sunday before Christmas finally rolled around and as agreed, Willa swung around Gregory’s flat after Church and after dropping Ethan off with friends for the day. Sure enough, the buck had come through for her again and the exact system was sitting on his living room table, along with a few extra accessories they hadn’t discussed. Willa picked up a pair of expensive looking headphones before turning to look at Gregory with a raised brow and asked, “What’s this?” “Relax, just a few extra’s I figured he would need…plus, they’re noise cancelling” he replied with a knowing grin. “Uh uh…you know I’m not planning on making any other big purchases anytime soon, so my butt will be off limits after today” the coyote replied with a knowing smirk back at him. “Speaking of…are you ready?” Gregory asked rather eagerly. “As ready as I’ll ever be, I suppose” Willa replied honestly, as she began to strip and head back towards Greg’s bedroom. “So, how long has it been since you last…you know” he asked, though clearly not as focused as normal, she could feel his eyes on her bare behind as she walked. It was flattering in a way, even in her late-thirties, it felt nice to be ogled by a younger man. “Took it up the bum? About fifteen years” she paused briefly to turn around and answer him. “Did you remember the lube and condoms?” “Yeah, I got everything you asked for” the buck replied as he scooted past her and headed into his room ahead of her. He sat on the edge of the bed and opened his bedside drawer to retrieve the items in question, which she noticed he had sprung for the expensive stuff too. He had even gotten the little vibe she had suggested, so she could have it buzzing on her clit while he did his thing under her tail. Willa had Greg remain sitting on the side of his bed, as she lay down beside him while she fished his length from his cargo pants. While she prepared him with her mouth, he would be preparing her behind with his fingers. Her soft groans and gasps were muffled by her mouthful of buck while his thick fingers gently and slowly teased her backdoor open to apply a more than generous helping of lube. She had warned him before hand not to be too eager or rough with her there, she had expected him to barely follow her directions, but what she wasn’t expecting was just how good he would be at it. Gregory took his time as he played with her butt, his touch was gentle and perhaps even teasing, he didn’t immediately try sink a finger into her either. Rather, he got Willa to the point she was lifting her tail and pressing back against his fingers willingly, finding his touch felt rather nice. When he finally did press a thick finger into her, she was thankful his cock was down her throat at that moment, otherwise she would have sounded like a real whore with how she groaned out, thankfully his dick muffled the sound. By the time he had two fingers slowly pumping in and out of her very well lubricated tail hole, Willa felt herself rather eager for something bigger. “Okay, I’m ready for you…” she finally pulled her maw from his length and panted, her soft hand grasping about the base of his length and giving a few last strokes. Though she tried her best not to sound too eager when she said it, she didn’t want him thinking this would be a regular thing and there was no telling how she would handle it after all. Gregory was on the above average side of things after all, and she wasn’t exactly a skilled expert at this sort of thing. Gregory didn’t say a word; he simply nodded down at her before helping Willa move to the middle of his bed on all fours. His clothing was shed in the blink of an eye and before she knew it, the buck was kneeling behind her as he hotdogged his eager prick between her buttocks while using her tail as a handle to hold her in place. Willa did her best not to tense up when he finally pulled back and pressed the tip of his cock against her pucker, knowing how big he was, but it didn’t matter. Greg had lubed his length up as well during his transition from sitting to kneeling behind her, combined with the prep work he had done under her tail, he slid into her with surprising ease after barely a moments resistance from her little pink star. “Fuck, you’re tight” she heard him groan, which was good. The way he had sunk into her, she was worried he had done too good a job on her backdoor. But then she felt it too, before he was even halfway in, that old familiar stretch made itself known. Last time had been painful, which she was worried would be the case now, only because back then her boyfriend was young and dumb. Thankfully, Gregory was neither of those things and he kept a steady pressure, always pausing when he heard or felt her tense beneath him. After what felt like ages, Willa finally felt his thighs touch her buttocks and knew he was all the way in. She only hoped he didn’t feel just how hot and slick her slit was below every time his large balls tapped and pressed against it from behind. “Y…you’re in…” she huffed softly, sounding almost surprised. She had expected there to be pain, but at most, there was just a little discomfort. She hadn’t expected to feel any pleasure though, especially since she hadn’t even turned on the little vibe for her clit yet, but when Gregory shifted and moved a little, there was definitely the spark of something there. If it felt this good without the vibe, Willa wondered what it would be like with it, to which she grabbed the small black cylinder from the bedside table and twisted the top, so it began to hum softly. The moment it touched her clit; she felt her eyes cross and a lewd groan spill from between her lips as a wave of pleasure crashed upon her. That was all the invitation Gregory needed, he felt the coyote MILF begin to move her hips and rear beneath him. So, he started to move too, his strong hands wrapped about her slender waist as he slowly and steadily worked this thick pink rod back and forth beneath her raised fluffy tail. She felt even better than she looked, as he stared down at her stretched little hole swallowing his cock. His dick was encased in an incredible tight warmth that swallowed him whole and felt like it didn’t want to let go. At one point she got even tighter, which he swore was her climaxing, but he wasn’t sure as she didn’t make any sounds to indicate as such. That and it was rather hard to focus on anything other than the pleasure in his dick, it was taking everything he had to not just let loose and fuck the coyote into his mattress. But he knew he needed to be careful not to hurt her right now. Willa bit her bottom lip as she tried not to cry out, she had not expected to cum from this. She definitely did not want to let Gregory know she had climaxed either, the last thing she needed was a horny buck that was interested in her butt knowing he had made her cum from anal. He would be pestering her for it all the time! If he thought she wasn’t that keen on it and didn’t enjoy it this much, she could leverage it for more help in the future. But that was whatever, right now she was enjoying a good intense cum, her mind felt all soft and pillowy, and her body was relaxed, despite having Gregory’s thick rod pounding her butt still. As they had discussed previously, Gregory knew to wear a condom, that way when he came, he didn’t have to pull out. Which was just as well as when his own climax hit, he was nowhere near mentally capable of performing such a feat. He’d have had better luck pulling the sword from the stone with his teeth than he would withdrawing his cock from that nice, tight hot little coyote hole. The buck leaned over the canine beneath him and almost bellowed loudly as he came so hard it felt like his balls were trying to turn inside out. He had never cum so much in his life, but as his hips jerked and bucked against Willa’s supple behind, he started to feel lightheaded. His head was swimming enough that he eventually collapsed beside her on the bed and stared up at his ceiling while his vision spun. “Holy fuck, that was intense” he huffed and panted, trying to catch his breath while his thick pink length slowly began to soften and droop over his left thigh. The condom felt heavy too, which was not surprising considering the amount of cum it contained. “Was the deal worth it?” Willa panted back at him with a little smile of her own, still kneeling on the bed, only now with her head resting on her folded arms and her ass up in the air. She could already feel a slight ache beginning to settle in beneath her tail, her behind was making it’s displeasure at being used well known and then some. “Oh yeah, worth every penny and then some” Gregory laughed and reached out to give the coyote’s still presented behind an affectionate little swat. “Good, but I’m glad his birthday and Christmas only come once a year” Willa said with a little laugh at the swat to her behind. “Oh yeah, how long until he starts driving?” Gregory asked with a knowing grin over at Willa. “My poor little ass…” the coyote groaned exaggeratedly, knowing there was another deal ahead sometime in her future she hadn’t yet thought of. A deal she would no doubt be knocking on Gregory’s door to help with, which in turn meant he’d be knocking on her backdoor again too. Greg was a good sport though, after they had both recovered from their sealing of the deal, he made them both a light lunch before helping Willa wrap the computer and the extras he had sprung for. Willa was kind enough to give him a thank you blowjob in return though, before she carried everything back to her apartment, although she did walk a little funny on the way there, but at least she had the new PC for Ethan. When Christmas finally came, Willa was only too happy to show Ethan his gifts, knowing she had the happiest son in the world. If only he knew what she did for it.