My Quarantine Survival Guide, Part 1: Reenter Riley ([MF], cheating, long)

There are stories that start off as humble brags and end up being a cautionary tale. There are stories that are supposed to have morals that are really pointless. There are works of absurdity. I’m not sure where this fits into the mix. I’m bored of consuming content and want to create something, to have anything to show for weeks of isolation. And it’s a little bit of “here’s an interesting thing; I hope you enjoy it.”

On some level.

I think this is probably a survival guide for the pandemic. We’re all stuck in a completely bonkers environment with little sprinkles of normalcy pervading our quarantine clusters. There’s death all around you and you need to make the most of the little bits of life that you can get. That’s rule one in the plaugelands.

Before the lockdown or quarantine started, I was watching that Freddie Mercury biopic. He had a line where he was talking to a girl (probably more than one line actually; it was a refrain to match the eponymous song) where he said she was the “love of his life”. And it seems a little stupid, right? That Freddie Mercury, the gayest rockstar of an era, has a woman that is the “love of his life”. I mean, he ends up with a dude. With a lot of dudes in between. Takes him awhile to get there, but that’s his jam.

The more I think of it, the more I don’t think it’s stupid. I’ve loved a few people, certainly the vast majority of the girls I’ve dated, maybe all, however briefly. I didn’t trust all of them, and most of the relationships didn’t last all that long. They weren’t “loves of my life”. But some people, some people have an outsized impact. It’s not that I loved her more, or even liked her all that much for vast stretches of time. But Riley had an outsized impact on my life, on my entire sexual development.

We initially dated sophomore year in college, for basically a year. She’s the one I lost my real, Penis-in-Vagina V-card to. Technically, we were still together when we came back the fall of junior year for a few months, but it had lost its spark. She had cheated on me; I found out. The whole mess of details is sadder than it is sexy. We broke up. I hated her and acted petty. She acted petty. We fell out and didn’t really talk for a year, and in senior year only while in the company of mutual friends.

I retreated into my shell for months. It hurt. But I came out a lot better on the other side. And frankly, (humble brag), I crushed senior year because I saw relationships in a lot healthier of a light. I started going to the gym. I got out of my shell and talked to people that I might not normally talk to. I got out and did stupid social stuff on campus. I let flings be flings, hooked up with a bunch of cute girls, and met a bunch of people that I wouldn’t have otherwise. As everybody does, I moved past it and was better for it.

We all graduated and bounced around the country. After some time soul-searching, I ended up moving to do a PhD (in bioinformatics, much much less sexy than it is boring for our purposes here). And guess who happened into my college town in the fall of 2018 to do an MBA? Not only my college town, for the record, but the same building, one floor up.

Reënter Riley.

I could have done nothing. It would have been awkward when we accidentally ran into each other getting mail or whatever, but it would have functioned. The thing is though, I didn’t feel like I needed to. I’d mellowed out a lot in, fuck, half a decade since undergrad. Thank our lucky stars that we’re not stuck as the people we are when we are twenty. In some ways, Riley had changed too, and in some ways she was exactly the same.

We had dinner periodically; we hung out in small groups. It was nice. For orientation, I’m an introvert. Not the most socially isolating person you’ll meet, but a run on a treadmill in a deserted apartment gym followed by Netflix and/or Nintendo Switch is not a bad evening for me. Riley is the opposite, which is why people love her. When she wants to be, she’s charming as hell, she remembers everything about people she meets, she tells great stories and she makes you feel like your stories are better when she’s listening. She’s funny, smart as a whip, and she’s some kind of brilliant actuarial ninja – once she finished the MBA, her company would put her up for months at a time in executive apartments to fix (or demolish, maybe?) the myriad business problems that befell their clients.

She’s also manipulative, two-faced, and has dabbled in being a sardonic bitch. But as I said, people don’t stay twenty forever.

Fast forward to February 2020. Everything is great, I’m in my first year as faculty in the same place where I finished my PhD (this is generally not encouraged in academia; we refer to it as ‘academic inbreeding’, but there are very few people working on the platform that I’m an expert in, and this is one of the centers that does it). I’m teaching a small section of biology for undergraduates. Riley is out and about in the diaspora, me having last seen her on a double date with Becca, the girl I was dating at the time, and her boyfriend Tom, before she was going to leave us all for Portland to completely obliterate somebody’s creative accounting dreams.

And then the sins of some dude from Wuhan who thought he found an awesome deal on raw bat caught up with us all. I hope it was tasty.

Riley was immediately recalled from the hotspot, and had to self-quarantine for sick contacts. My university sent all the undergrads home at spring break. My section was taken up by an online learning curriculum administered by somebody who does a lot more undergraduate teaching, so aside from grading some assignments, my work there is done. My research depends on other people doing research (again, not sexy) so with most projects in hibernation, there’s not much to do there either. I can accomplish most of my ‘work from home’ in the course of a good half hour every week.

But, on the plus side, the grant funding is there. My job is relatively safe. 20-year-olds don’t die from this (*usually*), so they’ll be back sometime, when it’s safer. Someday, there’ll be a vaccine, and the world will shift a dozen times before that. Like a hundred million other people, I’m locked down, but not out. And it’s not so bad for us, the introverts. I didn’t want to travel anywhere and risk spreading things to my family, but I had a nice, functioning quarantine circle. I know a couple of guys who have been living in my hallway, Brian and Benny, of 214 and 202, respectively. We had hung out from time to time, moreso recently. Brian had been with his girlfriend Kylie for the past six months. She started in the larger apartment 202 with her gay roommate Benny, but slept over at Brian’s more or less full time.

This was my quarantine cluster of the second floor. We were happy. But the extrovert upstairs, she’ll blow up your phone with boredom.

The grating buzz of my phone vibrating on a cake plate (Christmas gift, mother, 2016) interrupted my careful tessellation of pizza slices to be resuscitated in the toaster oven for dinner.

“What are you doooooooooing???????”

It was seven question marks and a hell of a lot of ‘o’s. She was desperate.

>“Not much. Pizza for dinner. U?”

“People that are going to have coronavirus have coronavirus in five days, right?”

I started to type a response and was immediately interrupted with the blinking ellipses that inspires more patience than any other 4 mm collection of pixels.

“Because I have not had a fever.”

“For a week.”

“I’m cured right? You’re a doctor”

>“I’m not that kind of doctor, but it sounds like you want to be cured. Therefore I pronounce it so.”

“You work with doctors. I just want one other opinion that supports the virtual visit lady. I have something that would go great with pizza.”

>”Come on down, but if you kill me with pneumonia, I’m going to be moderately upset.”

“Me too.”

Fifteen minutes later we were watching *Tiger King* and drinking a bottle of red wine with reheated pizza.

“I’m so glad to have someone else to talk to!” I remembered a thing about Riley was that she never watched a movie for longer than 10 minutes straight.

“You had Katie, didn’t you?” I asked about her roommate. “Or did you kill her with your Oregon plague?”

“Oh, yeah, super dead.” Riley laughed. “Nah, I got tired of listening her masturbate all day and she went to go live with her parents in Iowa. Rob. Iowa.”

She looked at me very seriously, mocking affront that someone would choose corn over her company.

“I hear it’s very lovely in March.”

“It isn’t.” She slapped me on the shoulder and reached to refill her wine glass. “Shut up.”

I shrugged and watched a tiger pace in his cage, clearly annoyed by his imposed isolation. Or that someone was using him as the background for a music video. Riley “watched” for awhile too, which is to say that she drank her wine while directing her attention more or less in the direction of the screen.

“Rob.”

“Yes?”

“We are not going to hook up.”

An hour later I pulled off the condom, put a neat knot in it, and tossed it into the trash. She leaned up on one arm, breast hanging over my comforter. “You’ve gotten a lot better at that.”

“Pfft. I cum the same as I ever did,” I said over my shoulder through the bathroom door as I cleaned off my dick.

“No, the fingering,” Riley flopped onto her back and laced her fingers behind her head, “you’re way better at fingering.”

“I’ve picked up a thing or two.”

It had only been one thing, as a result of an offhand comment made by an obstetrician in a general human anatomy lab. If you don’t know, here it is: when you’re fingering, you should be directing pressure anteriorly, toward the front of the person (if you’re doing a speculum examination, the opposite – you can take advantage of where nerves are or aren’t). If that’s news to you, there you go, I’ve just improved your fingering by a whole letter grade. I’ve found women who reliably come from penis-in-vagina, but it’s relatively rare – and there almost always has to be some clit involved. Some of my girlfriends could orgasm from oral, but that seems to be largely dependent on the girl. I haven’t changed my technique much and gotten widely variable results. But fingering? I’m pretty reliable with fingering. Obviously, me as a college sophomore was not so reliable.

“Yeah, you were way worse in college.” Riley looked at me with mock severity.

I took a few quick steps and pounced on her, pinning her hands over her head. I was rewarded with a quick gasp. “And now?”

“Mmmm.” She licked her lips and thrust her pussy toward my cock. “Now things are way more interesting.”

I demurred to her exaggerated frustration, bringing my knees and body up and pulling my cock away from her body. “Oh yeah, was Tommy not cutting it?”

“Fuck Tommy.”

“You aren’t.”

“He wouldn’t.”

Tommy was her now *probable* ex-boyfriend. I have a rule, largely because of the sophomore fallout. I don’t sleep with people in relationships. Well, let me amend that. I’ve never had occasion to, but if a couple were open, I wouldn’t have a problem with fucking a guy’s wife or girlfriend as long as she had his consent. But I don’t volitionally help people cheat. This moral high ground, I’m sure, annoyed Riley (particularly when I had occasion to bring it up at a party in her presence) given her past behavior. But fuck, it hurt, and I don’t want to contribute to other people feeling that lousy if I can help it.

That being said, I’m a fucking human, not a private investigator. If someone tells me they’re not attached, then I take that as true unless I had some reason to believe they’re not. I’m not going to go stalking on social media to figure out a girl’s motivations. I’m not on most of them anyway; everyone knows social media stopped being cool in 2010, and now the uncool mostly takes the form of acquiring and ruining other platforms and vague insinuations of political corruption.

In the half hour between the finished wine and the finishing of Riley, she had mentioned that she and Tom were over. That he, like her roommate, had flown off (“…to fucking Texas. Texas. And not the cool part.”) and that their relationship was pretty much over. So, taking her word for it (and I don’t have any particular reason to think she hasn’t also evolved in six years), neither of us is attaché. My previous relationship having been summarily murdered like so many others by Valentine’s day. Too new to fully commit, apparently not developed enough to blow it off completely.

During the before time, when restaurants were open, I hated spending $200 because of surge pricing on Valentine’s day. Becca had felt otherwise. Intensely.

Another personality flea that I picked up, probably also related to the breakup, is I like dirty talk from women about their sexual past. I’m not particularly proud of it, but there it is. I’m sure a therapist would be able to paint the connection from the first girl I was fucking who had cheated. Hot girl. Sex with someone else. Hot Girl. Cheating. The human brain is not so complicated. It’s a connection machine.

“How does a 30-year-old even get erectile dysfunction? Is that even possible?” She squinted her eyes and looked up at me.

“Sucks for him.”

“For all of us.” She nodded.

I let my weight fall on her a little bit, pushing my dick against her mound. “What about what’s his face? Russ?”

She looked at me sidelong, searching. “Ross? Are you sure you want to know?”

I kissed her deeply, searching her tongue with mine. I felt her back arch up and she pulled one of her wrists free and grabbed my neck, pulling me in closer. I broke the kiss and growled in her ear, “Call it an academic interest. We’re not together anymore, so I can look at it more…” I tweaked her nipple, “dispassionately.”

“I don’t know. I might need some motivation.” Riley cocked an eyebrow and reached down for my re-hardening dick.

“Are you clean?”

She nodded. “And my tubes are tied.” I don’t think she’d ever lie about that.

“I’m not sure exactly where to begin…” Riley teased, working her hand along the length of my shaft.

I pushed inside her, my clock sliding without resistance into her wet pussy. “Was he a good lay? Was it worth the trouble?”

“That… is two separate questions.” She looked me in the eye mischievously. There was something in her that was eager to be able to air out some old dirty laundry. “Shit, I can’t do this with you looking right at me.” Riley pushed me up and popped up to a sitting position. “Get your tongue inside me and I’ll spill all my secrets.”

Who was I to argue? She cleaned off my cock with a couple pensive licks and thoughtfully stroked my cock as I maneuvered into position and started gently licking her labia.

“Worth the trouble? Nah.” She tried to sound carefree, difficult given the weighty emotional valence the issue had once had and the presence of her genitals in my mouth. “In bed…” She trailed off.

I jokingly inserted my small finger in her pussy. “Mm?”

She laughed and looked down at me over her shoulder. “Hah. No.” Riley rolled her eyes and glanced upwards.

I pulled my head out from under her, pushing her butt up in the air and inserting two fingers, taking the opportunity to push on her G-spot again. Riley bit her lip and ran a hand over her boob shaking her head.

“Really?” I said, as I licked my hand and then slowly and methodically worked a third finger into her pussy. I gently rocked my fingers, in and out, pushing deeper and deeper. I felt my saliva mix with her pussy juices and whatever petrochemicals passed for lube on that condom. Riley shifted her weight and worked her pussy against me, burying my fingers to the knuckle. I worked my fingers in bit by bit, pinching her nipple and listening to her moan. She gyrated her hips a little bit, and then stopped abruptly. I stopped thrusting my fingers, and saw her raise a single index finger over her shoulder. I spat on my hand again.

Riley had lost track of her nascent story this time as I first slipped two fingers in, pressuring the sensitive wall again for good measure. The third finger went in much easier this time, and I worked the pinky in, bunching my fingers and slowly working the entrance of her pussy as she pushed down against me. Her breathing started to pick up. “More!”

“Bullshit.” I said, not interrupting the rhythm of my gentle thrusts. “His cock was not that big.”

“Of course not.” She looked back at me, “It was the two fingers. But I wanted to see if I could get you to fist me.”

I slapped her on the ass. “Maybe if you’re good.”

“Hard to argue with that.” She shifted down to her elbows, pushing her pussy back onto my face. I resumed by gentle circular licking of her slick labia.

“Compared to you now? He was a fucking 21-year-old. His best asset in bed was that he could legally buy beer.” She grinned and tossed her hair. “Compared to you then…” Riley was testing the water, “he was maybe somewhat more precise.”

I rewarded her with a gentle flick over her clitoral hood. Riley continued.

“But he didn’t take the hint, didn’t quite get me what I needed.”

I pulled my head back, “Orgasms?”

“Usually not, but that’s not atypical.” She angled her hips, bringing her clit to rest on my bottom lip as I continued coating everything in the mixing wetness. “He wanted a threeway. I thought that sounded-“ her breath hitched as I took her clit in my mouth, “fine. I like that idea. But he wanted to fuck his ex with me.”

A little shudder went through her as I licked up and down her clit. “I didn’t really want to fuck that chubby bitch.” Riley moaned, organizing her story. “I wanted… his roommate… Samir.”

I pushed up on my ever more crumpled pillowcase for a breath of air. “Fuck, that’s hot. Did you make it happen?”

“No, I was without all my tools of seduction back then.” Riley pouted. “Namely, I didn’t ask for what I wanted.” She brought her pussy back toward my face, and licked the undersurface of my cock. I could tell she was deciding how much she wanted to admit. “Come like this.” She turned over and fell onto her back at the foot of my bed, pulling me over with her, and I went back to work with an improved angle. Riley continued.

“All he ever talked about was this fucking threeway. And anal.”

“Did you give him that?”

Riley gave me a naughty grin. “Nope.”

“But he had this party. And he kept talking about it at little intervals throughout. I… maneuvered it,” she emphasized the point with a little thrust of her pussy on my face, “so that the bitch would leave. No regrets. Naturally, he got upset and started smoking a ton of weed, and the party wound down. It ended up with just me, him, and the roommate, Samir, passing a bowl. Mostly it’s just Ross going to town. Rob,” she brought her head up to look me in the eye with mock severity, “I didn’t inhale.”

“I believe you, Ms. President.”

She let her head back down and opened her legs an inch wider as I pulled my tongue repeatedly over her pussy, labia open from the cumulative hour of intermittent fingering and fucking.

“Eventually, after telling us both how high he was like 40 times, *super* attractive by the way, he passed out. I leaned over, and grabbed Samir by the cock,” Riley ran her fingernails over my head, “you know, to gauge his interest.”

Riley breathed heavier as I picked up the pace a little bit, egging her on. “Finding him to be… amenable… I went to the bathroom…” she bit her lip and paused as I continued licking. “And…” she continued breathing. “I-“ I reached up and pinched her nipple and pulled her clit into my mouth. “I went to the bathroom and cleaned my ass.” The words came spilling out.

“Naughty girl.” I praised her. I wanted to keep her talking, keep her comfortable. “Had you had anything in your ass at that point?”

“Mhmm.” Riley’s words came a little easier. “My fingers.” I gave her pussy a lick and ran a finger around in the juices. “And these plugs – a little jewel one and- oh- yes-“ I worked my wet finger in a tight circle around her backdoor. Her breathing hitched again and the words came tumbling out, “And a bigger glass one.”

“Fucking slut.” I pulsed pressure with my fingertip on her taut butthole and gave her pussy a quick lick before continuing. “You wanted to be sodomized.”

“I like fucking. I want it all- every way.”

This might have been one of Riley’s guiding principles. The Tao of Everything. Pushing for new experiences. Milking whatever she could out of relationships. The everything bagel of fucking. But I had butt to consider.

“Did you give him your ass?”

“I did.” She tentatively lifted her pelvis a little bit, bringing her ass forward. I rewarded her with a cursory lick. “Mmphf. Yesssss.” I worked my tongue in slow circles, grabbing her ass with one hand, helping her spread her labia with the other as her hand moved over her clit.

“I came out of the bathroom in just my underwear. And I asked him if he liked what he saw or something stupid like that. And he came over and grabbed me and I told him what he’d be doing for me. I could feel his hard cock. Mmm. I knew that I had him in thrall.” Riley gasped a bit. “I brought him… yes…” she reacted as I pushed my tongue hard against her rosebud and scratched my fingers over her glute. “I brought him to,” her voice went up an octave, “Ross’ bed.”

“Did he take you right away or did you need to warm him up?”

“Just a bit. I think he was waiting- waiting for me to show him it was alright. I put his cock right at my ass and he held it there, just kind of letting my butt acclimate. Then I pushed down and it was like I opened the floodgates. He pushed all the way in. I’d lubed myself up in the bathroom, and they always say you should err on the side of overdoing it. It was a fucking mess, lube everywhere, all over his cock, on his balls, and he was barely moving, just holding deep inside me as I ground my clit into my boyfriend’s pillow, the whole of me-“ I could feel her muscles tensing to come, “pinned by him and filled by him.”

Riley came, grinding her tense hole on my tongue, convulsions running through her. I barely moved my hand and she twitched, rolling off to the side. She breathed heavily for a minute and purred.

“Fuck… academic interest, huh?” Riley leaned up and looked me in the eyes. “You professors fucking know how to do it.”

She straddled my cock, getting into cowgirl position and began riding. This was another of Riley’s tenets that I hadn’t had occasion to think about in awhile. She was really good about making you cum after you made her cum. Maybe not a golden rule, but a kind of drippy, sticky, pearlescent translucent white rule, anyway.

“And was that it?” I asked, taking the story out of the sexy zone, “you broke the boy’s heart and broke up with him?”

She rocked more gently. “I mean, in not so many words? Basically, I just started acting like an immature bitch, caused a huge thing, and he broke up with me. Didn’t see him for like three years and then he got super fat and married this Christian chick. Essentially the optimal exit strategy. Never saw Samir again though. You really like hearing about this shit?”

“I like hearing sexy things.” I looked at her. “About the adventures of sexy people.”

Riley gasped in mock shock and covered her mouth with her hand, squeezing her cunt around my cock. She clandestinely licked her finger. “Rob, you’re a voyeur.”

“Mm.” I shrugged. “Among other things.”

“Me too.” A Cheshire grin took her face, illuminated by a streetlight through the window. “Man, you’re gonna love my consensual non-consent phase.”

“Your what? What’s that?” I knew, but I wanted to make her say it.

“It’s an adventure undertaken by sexy people. I’ll tell you about it. Later. I have to take care of something first.”

She put her hand behind her back, angling her slick finger down to my asshole, rubbing around the edge. This, by the way – is in no way related to anatomy class – but is the best thing about eating ass. I don’t think anybody exactly tossing salad (prove me wrong, perverts), but it’s fine. And importantly, it sends the signal that you’re prepared to have all your erogenous zones used. It must have worked in this case as well, because there’s no way I would have let her try it the better part of a decade ago. Another mode of growth.

Riley continued just barely pressing on the entrance of my hole as I started timing my thrusts to meet her. Given that I’d come once before, I was getting a nice, long, slow buildup. But as I watched her tits bouncing in perfect rhythm and felt her wetness dripping down my balls to meet the finger that was rubbing my ass, I couldn’t hold it in anymore and pumped my cum inside her, probably voiding the warrantee on those tubal ligation clips.

Riley reached down and cupped her pussy gently as she rolled off, leaving a trail of cum on my abdomen in her wake. She deftly scooped it up with her finger and licked it. It was silent except for breathing… I’m not sure for thirty seconds or an hour.

“I’m not yours, you know.”

“I know.”

“Alright.” She gave me a pat on the chest. “So… I can’t stay.” She made her way to the bathroom.

“I know.”

Four hours later, I was reminded of one of the bad things about Riley. She hogs all the covers. Mercilessly.

​

Hope you enjoy the first attempt :p – so far I’ve learned that those tags are no joke. I think this attempt will stick. Probably a part 2 by this weekend, then maybe more…

Source: reddit.com/r/gonewildstories/comments/geb1ns/my_quarantine_survival_guide_part_1_reenter_riley