One Small Oversight

Story by ComfortableCreatures on SoFurry

, , , , , , , , , , , , ,

An overweight, lonely guy asks his bisexual best friend to take a pill and become the (furry) girl of his dreams for two weeks. What could possibly go wrong?

Finally finished this one after a great deal of procrastination, filled with some of my favorite fetishes, I hope you guys enjoy! I definitely plan to make a follow-up to this as well.

Whats next? Most likely I will do the follow-up to my first story, Meeting the Folks, and wrap up that story. Hopefully that one doesn't take as long, I plan for it to be very brief much like the first story.


Mark looked over his friend, Jacob was clearly nervous about this. It wasn't a big surprise though, so was Mark. This had all started when Mark had come out as bi, Jacob had asked if Mark ever thought about him...sexually. Mark had told him the truth, or, most of the truth. He always saw Jacob as a friend, his best friend. But Jacob's flabby out of shape body, pale skin, patchy attempts at growing facial hair, and his tendency to wear almost nothing but sweat pants and oversized t-shirts didn't exactly make him a total catch. So, no, Mark hadnt had any sexual fantasies about his friend. But Mark didn't tell him that, because that didn't mean Mark hadn't considered dating him, past the physical side of attraction, he was Marks best friend, they had everything in common, he was a talented artist, and Mark respected that. He told him that, and Jacob told him he was straight, and that was that. Until one night after a few too many drinks, Mark had told Jacob if he was ever interested in...fooling around, he might be open to such a thing. Jacob told him he was drunk, and helped him get home, at least thats what Jacob said happened, Mark doesn't remember the night at all.

And Mark hadn't though about the subject since, until he had told Jacob that he planned to go on a five month long trip, touring different countries around the world. And Jacob had called in that drunken favor, Mark didn't ask where Jacob got the money for a gender swapping pill, especially not a custom order one. Those cost as much as a new car, and he was likely going to be paying it off for years with how much he made drawing furry smut.

Mark rolled the pull around with his thumb. “So, whats the effects? I assume its going to make me a...y'know."

“Furry? ...yeah. One of my characters, she is a raccoon named Alicia, I'd love it if you would...well, uh, go by that name? While we...yeah." Jacob picked up his tablet, turning it around and showing Mark.

Mark looked her over, it was a reference sheet. On it was a rather skilled drawing of an anthropomorphic female raccoon. Her fur was fairly a standard gray and black pattern, aside from a small constellation of black stars, around seven in total, on her otherwise gray fur, trailing down the left side of her smooth belly. The rest of her body was thick and busty, but not unrealistically so. Lastly she had shoulder-length black hair with hot pink highlights. “Okay...Alicia it is. I didn't really expect you to be calling me Mark the whole time." Mark said, handing the tablet back.

Jacob smiled at this. “The pill lasts for two weeks, that's the shortest I could go. Something about your body needing to recover from the shock of the transformation before changing back. That's alright, right?"

Mark looked at his watch, and nodded. “Yeah, I got to leave next friday to make my east coast flight, but then I got about two days before I have to meet the travel agency, so I should be back to normal the day before that. Anything else I should know?"

“Uh yeah, there was a few...optional things I went for, to hopefully make it more fun for both of us?" Jacob said, a little more nervous.

“Like? Don't be nervous, I told you that you could do whatever you wanted with it, this is for you. Just remember, I am square for like, every birthday and Christmas from now on." Mark said, giving a joking smirk, doing his best to be patient. Despite both of them being twenty four, he knew Jacob was still a virgin and despite how weird and awkward this was, he also knew it meant a lot to him. Mark had seen first hand how hard he had taken rejection in the past, the fact that he even asked meant he was desperate, the least Mark could do was make his first time as special as possible.

“Well, a few things were to help you maybe get...in character?" He said, fiddling his thumbs, clearly still very nervous.

“In character?" Mark asked.

“Yeah, well, I was hoping you wouldn't just let me call you Alicia but also..."

“Act like Alicia?" Mark said, cutting Jacob off. “If you want me to roleplay that's fine, it will probably make it less awkward for the both of us if it doesn't feel like it's me in there, I get it. Just tell me what she is supposed to be like."

“Well, she is very sexual and uh, slutty." Jacob stared at Mark's face, clearly gauging his reaction. Mark made sure to just nod with a small smile, urging him on. “She can be very...assertive? Like if she wants sex, she gets it?"

“So she is dominant?" Mark asked.

“No, well, she can be, but she can also be submissive. Um..." Jacob rubbed his chin, his nerves obviously making it more difficult to articulate what he means. “You know, she will beg for it and uh...whats the word...needy!" He shouted that last word out, as he finally got it off the tip of his tongue.

Mark laughed at that. “Okay, a needy slut, like she will submit to anything that will fuck her, but might get a little rough if she is needy enough?"

Jacob nodded, clearly somewhat relieved that Mark understood, and wasn't rejecting the idea. “Yeah. I went through tons of the side effects they have to help that along. I got a few that should make you pretty horny."

Mark raised an eyebrow. “A few?"

“Yeah, a few. The first one is just a general 'libido boost' as they called it, I also gave you a heat cycle, like an animal...and you should be in it once you change." Jacob blushed. “And uh, the last one is scent based, since your nose will be more sensitive, they let you send in a sample of certain, scents, and it will trigger and aphrodisiac effect when you smell it. They recommend things like...sweat samples."

Now Mark was blushing, not at the fact that he was going to be turned on by Jacobs sweat, as gross as that sounded it was sensible and natural. No what had gotten to Mark was just how many libido boosts he was about to endure. “Well, I certainly wont have trouble with the needy slut part..." he said, chuckling.

“That was the idea...I also made tweaks for flexibility, tightness, elasticity, durability, vaginal texture-"

“Okay, I think I get the picture." Mark cut Jacob off again. “You covered everything. So, how are we doing this? I mean I am going to take this pill, go in your room and get undressed, lay down until it...does its thing. What do I do after that? Bend over and call you in? Come out? Do you want me to say anything?"

Jacob thought about it. “I was hoping we could do some kissing and touching first, but after that...well, I'm a little nervous about how I will uh, perform. I think I would like a blowjob as a warm-up, before we do anything else if that's okay?"

Mark nodded. “No problem. Its your first time, I dont expect you to have the stamina of a porn star. Now then..." Mark popped the pill into his mouth, swallowing it quickly. “You get undressed, and I'm gonna go let your girlfriend know what you want, then climb out your bedroom window." he said with a wink, making Jacob chuckle a little.

Mark stepped into Jacob's room, shutting the door behind him. His heart was racing, he made sure to make a show of taking the pill not just so Jacob would know he wasn't having second thoughts, but also to make sure he didn't actually have them himself. He had never considered, or really wanted to experience life as the opposite sex before, he was happy with his own body. Not only was he about to change into a new one, one not even human, but he was going to use it to have sex with his best friend.

Mark sat down on the edge of the bed as he struggled with this thought, even though Mark wouldn't be opposed to dating Jacob, this temporary arrangement though just made it feel...off, it was weird and awkward, but in some ways kind of exciting. Mark looked down at his cock, knowing it was the last he would see of it for two weeks. A few minutes passed, and he began to feel something, a tingling and heat slowly building from within. He crawled up onto the bed further, laying down. The tingling spread through his body fast, it felt like when your leg falls asleep, but it was all over, it grew in intensity alongside the heat, soon the prickling was starting to seriously hurt and his body felt like it was on fire, but before it became unbearable, he blacked out.

He awoke what felt like moments later, like being put under at the dentists time just seemed to flow differently. He groaned as he sat up, suddenly surprised by the difference in his voice, but not just that, how different his mouth felt, his tongue felt strange inside of it. He looked down at his body and saw those large, pillowy breasts now adding a new weight to his chest, and the soft looking fur covering them. Mark...no, Alicia, he was Alicia now. She was Alicia now, for the next two weeks she had a character to play.

Alicia moved a hand, curiously between her legs. Feeling her own soft fur on her inner thigh before her fingers reached her brand new pussy, eliciting a sharp moan as they brushed against it. Whatever sedative must have been still wearing off, as she now began to feel just how horny she was. Her nose twitched, as she took notice of the strong scents the room now contained, her groggy mind still just processing all of these things one at a time. She blushed, she was supposed to be turned on by Jacob's scent, and she definitely could feel it, the room reeked of him, reminding her of the times they would hit the basketball court in the park, how he smelled afterwards.

Alicia shook her head, and tried to rise to her feet, only to fall right back down onto the bed. Looking down, she took note of her new legs, bent like a dogs hind legs and ending in fluffy paws and pink pads underneath. She groaned out, before trying again, taking it slow as she got used to the feeling of walking on digitigrade legs. It was then that she made her next revelation about this new body, the reference sheet had not gotten across just how short she was, Alicia must have been at least a foot shorter than her old body.

On shaky legs, she made her way into Jacob's bathroom, looking in the mirror, audibly gasping as she saw her own face. She really was the spitting image of Jacob's drawing made reality, the level of accuracy the pill achieved was astonishing. She ran her hands along her new curves, brushing along the stars on her left side...she wondered if for the character he drew, that these were some kind of tattoo, or dye? But for her it was her natural coat now. Her hands continued down to her thighs, where she reached back, grabbing her new bushy, ringed raccoon tail. She tugged on it lightly, confirming to herself that it was a real tail.

“Damn it Jacob, did I need to be this horny..." she said, staring into the mirror. Since her hand had left her nethers, she had wanted nothing more than to touch herself more, the need only growing stronger as whatever sedatives the pills had packed wore off. She felt more intoxicated with lust than she had been with any other substance at even the wildest of parties.

She walked around the room, until she was used to her new legs and new center of gravity, once she was confident that she could walk stably, at least in a straight line, she pushed open the bedroom door, back into Jacob's living room.

Her eyes locked onto his form, his naked bronze skin dotted with sweat, no doubt because of how nervous he was. Not that she needed to see it to know how sweaty he was, she could smell it, it reeked of him in here more than his bed had and it was fresh from the source. Her eyes trailed down, to his unkempt pubes and the head of his flaccid cock sticking out of them. Then her eyes trailed back up his flabby form to his face, he looked awestruck at the sight of her. It wasn't the first time she had seen him naked, the two grew up together, took gym class together, went to summer camp together. She smiled and began to approach.

“A...Alicia?" he asked sheepishly.

He was clearly even more nervous now, understandably so. She would have been nervous too, but she was way too horny to care about how weird this was right now. “Mhm." She stopped right in front of him, bending forward and leaning in, looking him in the eyes. “I am Alicia. And my body..." She grabbed her tits, fondling them in front of him, watching his eyes widen as they flicked down to view the display. “...belongs to my boyfriend, Jacob. And his body..." She reached down with one of her hands, between Jacob legs, cupping his balls and eliciting a gasp from him. “...belongs to me." She finished leaning forward, pressing her muzzle against his lips, pushing her new, flatter tongue into his mouth eagerly while she continued to fondle his balls.

Jacob was stiff, in both senses of the word. She knew hearing something so over-the-top like that from his fantasy girl must have been something quite special, and his cock grew hard in an instant. The rest of him was unmoving, he was just too nervous. She grabbed Jacob's wrist, pulling it to her breast, as soon as she did that, she felt his fingers wrap around the soft furry orb.

Alicia moaned out, surprised as she realized her new nipples were actually pretty sensitive, treating her to an odd and somewhat surreal sensation. She wondered if this was how it felt for most women, or if hers had been tuned up by Jacob's pill. Soon after he began fondling her breast, his other hand moved, this time of its own accord, grabbing the other. Moaning softly into his open mouth, she let him play with her breasts for a little bit, letting him feel and fondle, his touches more exploration than actual foreplay. Ultimately though she broke the kiss, smiling at him as she pulled back, placing both hands on his, gently pulling them away from her breasts. She saw the pang of disappointment on his face as he was deprived of her, but that expression quickly turned back to a mix of nervous excitement, as she lowered herself down onto her knees, Jacob knew what was coming.

She pushed his knees apart and grabbed the bottom of his gut, pushing it out of the way. Leaning in, her nose twitched, then scrunched up, it was like passing through a solid wall of that musky smell, exceptionally strong to her sensitive animalistic nose, so much so that it stopped being the familiar scent of a sweaty, horny guy, its intensity making it unrecognizable. This only made her lust stronger of course, and her breathing grew heavier. She leaned in, and as that breath washed over his cock, she watched it twitch, his whole body shudder with pleasure. He was already on a hair's edge. She looked up at him, it was about as unflattering of an angle as one could get, but there was also something sexy about looking at someone from below, perhaps because it was just the proximity to their crotch, or it was how submissive it felt to be on your knees, looking up at a man you were about to service.

She smiled at him, then turned her attention back down. The time for foreplay was over, if she took any longer he would finish without her even touching him. She opened her muzzle and leaned forward, taking the head of his cock into her mouth. Sliding it deeper inside she went easy on him, her tongue unmoving as the bottom of his dick slid over it, tasting his salty pre and the musky masculine flavor that was so similar to that overwhelming scent she was experiencing. His cock was roughly average sized, but her new muzzle also afforded her an extra inch or two of depth to her mouth, making for a rather shallow deep throat, her nose twitching as it was tickled by the mess of pubes at the base of his cock. She quickly got into the rhythm of things, bobbing her head up and down along his shaft, listening to his grunts, moans, and even whimpers as he experienced his first blowjob.

The whimpering noises he was making, the constant twitching of his cock within her mouth, she could tell he was trying desperately to hold back, he was teetering on the edge and could cum at any moment. She was ready, ready to taste his seed. She wasn't ready however for his hand clasping her head from behind so roughly that he practically slapped the back of her head as he pushed her down, forcing her to take all of him while he groaned out, cumming straight down her throat. She coughed and sputtered around his cock, each twitch sending another hot, slimy shot of jizz directly into her stomach. Eventually his grip and body slacked, and she was able to pull herself free, still coughing.

“S-sorry!" Jacob stammered out. “I got a little carried away..."

Alicia reached up, putting a finger to his lips while she finished coughing, clearing her throat before speaking. “Don't. I liked it." She said, giving him a grin. “You can do whatever you want to me, remember?" She looked down at his softening cock, then back to his eyes, placing a hand on the side of his face. “And I can do what I want to you...lay down on your back." She said, pushing against his head, guiding him onto his back.

“Wh-what are you-" Jacob's question was answered before he could finish asking it, as soon as he was flat on his back, Alicia climbed up onto the couch, straddling his face, her pussy just inches from his head, now positioned between her thick thighs.

“My turn." She moaned out, lowering herself down, pressing her pussy lips against his mouth. As soon as she did she felt his tongue slip out, pressing against her folds, his hands reaching up and clasping the bubble butt he had given her. “Mmm, don't be afraid to really get in there." she said, grinding against his face teasingly. She felt him give her ass a squeeze, as he pressed his face up against her sex, taking her advice and pushing his tongue into her, earning a sharp moan from the raccoon girl. “Oooh, that feels good, keep doing that..." she said through pants and moans as his tongue found a sensitive spot, doing her best to let the first-timer know when he was doing something right.

She kept riding him just like that, when she felt one of his fingers traveling, teasing against her sphincter. Her hand shot down, grasping his wrist as though to stop him. She brought his hand up to her muzzle, and began to lick at his fingers, leaning forward slightly so that her breasts wouldn't block Jacob's view, making a show of it as she ran her tongue along his fingers, lathering them in her spit before letting go of his wrist. He took the hint, bringing his hand back down to her ass, and pressing his saliva covered finger against her back entrance. When she didn't stop him, he pushed forward with it, sliding into her ass with ease.

As his finger began to pump in and out of her tailhole, accompanying the pleasure of his tongue, Alicia began to feel something building up deep within her. Determined to not squander her time as a woman, she wanted to experience something she could never experience as a man. “M-my clit! Focus on my clit!" she ordered, Jacob quickly obeyed, his tongue rubbing against the small sensitive nub, eliciting screams of pleasure from the raccoon. Her thigh's clamped down on his head, her whole body trembling as her orgasm overtook her, her first female orgasm. “Faster! Harder!" She screamed out, telling Jacob not to stop. Jacob did so dutifully, adding a second finger to her ass before thrusting both harder than before, his tongue rubbing against her clit as quickly as he could make it.

That combined with her extreme arousal was all it took for a second orgasm to overtake her body, and to her surprise, a third. Her whole body trembled and convulsed, any words she said were incomprehensible. Eventually the intense bliss began to fade, Alicia panting, tapping Jacob's head to get him to slow down. He stopped and she stayed in that position for a few moments, basking in the afterglow, before realizing that she felt something she hadn't felt since taking the pill...clarity. She still felt aroused, enough that she could easily keep going, but not so much that it was nearly as all-consuming as it was before, seems the designers of these pills had some mercy.

Alicia crawled off of her friends face, getting back to her feet before looking at Jacob, laughing as she saw how soaked his face was. She reached down and grabbed the shirt he had been wearing earlier off the ground, tossing it towards him. “That, was incredible." She said, while Jacob sat back up, using the shirt to wipe her feminine juices from his face. Her eyes traveled down his body, to his fully erect shaft...it was no surprise he was ready to go again after that.

Jacob sat up, wiping his face dry on the back of his shirt before discarding it again. He looked at Alicia, smiling as he rose to his own feet. Alicia craned her head to look up at him, her and Jacob used to be the same height, give or take. Both of them having been somewhere around six foot, but now she had a sudden reminder of how the pill had made her a shortstack, now eye level with his chest. Jacob leaned in, planting his lips against her muzzle, giving her a short kiss.

“Anything I want, huh?" He asked, in a low voice.

Alicia nodded, then let out a surprised little gasp as Jacob grabbed her hand, gently guiding her to the side of the couch, giving her another quick kiss before spinning her around, and bending her over the arm of the couch. Alicia moaned contentedly, now he was getting into the spirit of things...he gave her ass a little slap, earning another little gasp before she felt the tip of his shaft prodding at her soaking wet sex, lining himself up...and with just one thrust, he was inside, the both of them moaning out in unison.

His cock was a snug fit, but not uncomfortably so, and it had no problem sinking in to the base in his first thrust either, that must have been part of the elasticity he had mentioned, it certainly made him feel even bigger. She could hear Jacob breathing above her, he seemed to be taking a moment, perhaps he was reveling in the fact that he had just lost his virginity? So had she in a way, and her mind was still struggling with that...her best friends cock was in her vagina...there was something very surreal to that idea, but it was...nice, and it certainly felt good. She felt his gut press against her back as Jacob leaned in, his breath on the back of her neck and his hands creeping around her, grabbing each of her breasts.

“I love you, Alicia..." Jacob muttered, as he began to slowly buck his hips in a short humping motion.

Alicia blushed, was he saying that to the Alicia in his head...or Mark in Alicia's body? “I love you too, Jacob..." she muttered back, feeling a little guilty to be saying that so romantically without being able to truly mean it. He was her best friend and she did indeed love him in many ways as a friend, but she knew loving him as anything more was just...not meant to be. But she still returned his words, no matter what he meant by them or what she herself meant, she had promised to play the part of Alicia for him.

Jacobs thrust's began to pick up pace, and Alicia moaned with each and every one, her sensitive nethers and high libido already working her up. Her fluffy tail wrapped around his waist instinctively, she never knew what to do with it, but it always seemed to have a mind of its own so she just ignored it. Jacob grunted into her ear, many people didn't like the sound of a guys grunts and moans in sex, and it certainly wasn't a flattering sound, but she always appreciated hearing her partner and knowing that they must be enjoying themselves to some extent.

His thrusts had already brought her to an early orgasm, she gripped the couch cushions while her pussy clamped down on his cock. She was just so damn sensitive, but she was already seeing that as a benefit, her bodies ability to keep going after an orgasm was already proving to be a lot of fun. That is when his thrusts picked up the pace yet again, becoming almost frantic.

“Ugh...sorry...I thought the blowjob...I am going to..." Jacob sputtered out, between his own frantic moaning.

“Shh." Alicia silenced him. “Its okay, you lasted longer than me..." she reassured him, it was his first time, and in a pussy he had designed to be more pleasurable than normal, had he not already cum once he probably would have blown his load in seconds anyway.

He bottomed out in her, gripping her breasts tightly as he pulled her against him, groaning out loudly as his cum began to shoot right into her.

Alicia moaned out, the rough handling of her breasts, the feeling of hot seed spilling inside her, it was enough to bring her to a second orgasm on the spot, her pussy now milking his rod for every drop.

Eventually the two were breathing heavily in a joined afterglow, Alicia held tightly to Jacobs chest. A smile curled across her muzzle, she knew this was going to be a fun two weeks of sex, pizza and video games.

Jacob looked at his phone, double checking the time. Mark should have landed by now and would be by any minute. It had been a week shy of four months since Mark left, he was still Alicia when Jacob last saw him, but the transformation would have ended a day or two into his trip. Jacob was excited, aside from a few text messages he hadn't had a chance to talk to his friend in all that time. Although it was weird he was coming home a month early, he had said he would explain that when he got back.

Jacob jumped up as the doorbell rang, rushing over to the door and pulling it open. However, where he expected Mark's face, instead was the raccoon muzzle of Alicia, and as his eyes traveled down her figure, to where her hands rested on the unmistakable bulge of a four month pregnant belly under her shirt. Jacobs mouth went slack, he had forgotten to put birth control on the pill he gave Mark..."Oh, shit."