Sharing Is Caring 31

Jerry Hoskins closed his eyes and counted to ten, cursing for the hundredth time that he had ever accepted that fucking Craigslist ad looking for a roommate

He picked up his gallon of milk with a furious look in his eyes and shook it, watching the half-inch of milk left in the bottom slosh back and forth, growing frothy.

Written in bold, optimistic sharpie across the side of the jug were the words "JERRY'S MILK! BUY YOUR OWN!" As if messages like that had ever fucking worked on Chris. For a second Jerry weighed just letting it go. Their lease was almost up. In a month he would never have to see Chris Denson ever again.

But the principle of the thing was what mattered. Principle was why Jerry still marked all of his things in sharpie, even though it never even made Chris hesitate. And it was why he was going to march over to Chris's room, just like he always did, even though he knew that it wouldn't accomplish anything.

Jerry closed the fridge door with his hip and made a beeline to Chris's room, seething with resentment. Jerry didn't see himself as a difficult person. Disciplined maybe. Strict with himself and others perhaps. But difficult? Never. Jerry wouldn't even care if Chris helped himself to an occasional glass of milk, or a roll of toilet paper, or a frozen pizza Jerry had bought.

But it wasn't just once in a while. Chris's casual "borrowing" was fucking constant. Jerry's asshole roommate wouldn't buy anything if he could mooch it. And that wasn't the worst part.

The worst part was his fucking attitude about the whole issue...

When Jerry swung open the door to Chris's room, his huge, muscular roommate was lounging back on his bed as usual. The bastard had a huge bowl of fucking cereal in front of him, happily munching away, milk fucking dripping down his chin.

But Chris wasn't alone tonight.

Seeing Kelly North took a little of the wind out of Jerry's self-righteous sails. Kelly was Chris's girlfriend, and she was the sort of girl who made Jerry feel awkward and tongue-tied just from her presence. She was a petite, spunky firecracker of a woman. She was the head of the college dance team, and she had the lithe, tight little body to prove it. Kelly had thick, natural blonde hair perpetually pulled up into a casual ponytail, a sprinkling of freckles over her cute features, and playful brown eyes that always made you feel like you were either in on the joke, or the butt of the joke, depending on her mood.

Jerry usually felt like the butt of the joke.

Kelly was the sort of girl who had been able to easily attract the hottest guys in high school, and never considered looking further than that when it came to dating. Why would she when she had the hottest, richest, coolest guys drooling for her?

The fact that this impossibly gorgeous girl was dating his asshole roommate was enough to make Jerry feel awkward around her all on its own. But what had happened a few months ago made being around the gorgeous young woman sheer torture for Jerry...

"J-man!" said Chris, around a mouthful of cereal. "Ever heard of knocking? What if me and Kelly had been getting busy in here?" His voice was joking, but there was an undercurrent of cold cruelty that was impossible to miss. Chris was a mean, spiteful meathead who had taken one look at Jerry on move-in day and instantly classified his new short, thin roommate as beneath him in every way. He had treated Jerry with casual disrespect ever since.

Chris raised a thick eyebrow at Jerry. "Well anyway. What can I do for you?" he asked, conspicuously taking another big bite of breakfast cereal. Kelly suppressed a giggle, covering her mouth in amusement at the sight of Jerry standing flustered in the doorway with his empty jug of milk.

"Chris..." said Jerry vaguely, trying to fight through the sudden awkwardness of seeing Kelly unexpectedly. He raised the empty milk jug and sloshed its pitiful remaining milk around. "You can't just take my stuff. You need to buy your own shit." He had planned to come in with guns blazing, but in the moment, his voice sounded weak and whiny even to his ears. Kelly snorted another giggle, turning to bury her face in Chris's shoulder.

Chris grinned and held up a finger, raising the bowl to his lips and gulping down the remaining milk, making Jerry wait as he downed the last of it. He let out a loud "Ahhhh!" much to Kelly's breathless amusement.

Jerry could see it in Chris's shit-eating grin. He was about to say it. That same old fucking phrase that he used every time. The one that made Jerry's blood boil.

"Jesus, J-man, didn't they ever teach you anything in kindergarten?" asked Chris with nasty fake-friendliness, "Sharing is caring!"

Jerry felt his pulse rev up. This time he wasn't going to let it pass. He had heard enough of that fucking phrase. He was really going to let Chris have it. It didn't matter that Kelly was here. She could listen too. Maybe then she would stop looking at him that way.

But as he opened his mouth, Chris bulldozed over him with his booming, confident voice. "Now get the fuck out of my room, Jerry. Me and Kelly need some private time, and we don't want a little perv like you sniffing around. Right, babe?"

Then Jerry turned and saw the amused disgust in Kelly's deep brown eyes. The same expression she always wore when looking at him ever since that day a few months ago.

And he caved. Jerry turned tail and retreated from the room.

There was just no way he could face a beautiful girl like Kelly now that she knew all his deepest darkest secrets.

...

Kelly North stared up at the ceiling, listening to her boyfriend snore noisily next to her. Kelly could never count on pillow talk or cuddling from her big lug of a man. After every session, he would roll over and be out like a light within minutes, no matter what time of day. It was one of his many bad habits.

Kelly sighed and shook her head at her own bitchiness. She was being unfair. In a lot of ways, Chris was talented in bed. His size was perfect: big but not painfully so. More importantly, he had stamina and power, which was a must for Kelly: she loved a man who could take charge and throw her around a little.

It wasn't his fault that Kelly's mind had been... focused on other things lately.

No, it wasn't Chris's fault. It was that pervy little loser that Chris had been forced to room with.

Jerry gave Kelly the creeps. Ever since the day they had first been introduced, Jerry's eyes had always seemed to linger on Kelly's body whenever he looked her way. Jerry was obviously checking her out at every opportunity he got. As if a little dork like him could have a chance with someone like her.

So, while Kelly recognized that Chris was being a major asshole by messing with Jerry all the time, she couldn't really fault her boyfriend. Jerry was the kind of creepy loser whose baseline existence was just a little annoying, and it was sort of satisfying to see a superior guy like Chris put the little perv in his place.

But if Jerry used to creep her out, he just flat-out disgusted her after what she and Chris discovered several months ago.

Chris had just broken his laptop again, and the new one his dad bought for him hadn't come in the mail yet. So, one day, while Jerry was off doing whatever nerds do, Chris decided to borrow his roomie's laptop to get some homework done.

It was the whole "sharing is caring" joke that Chris thought was so funny again. A series of petty little power plays that her boyfriend knew Jerry was too much of a pussy to stop. Eyerollingly immature? Yes. But boys would be boys, and even Kelly had to admit it was pretty funny to watch the weedy little nerd get all flustered and angry when Chris "borrowed" his stuff. Regardless, this time it was easy, Jerry had forgotten to lock his laptop, leaving it open on his desk for Chris to borrow.

That was how they found the pictures.

An entire album of some of the filthiest, most erotic images Kelly had ever seen. A pale, curvaceous woman bound with ropes. With leather straps. Blindfolded. Gagged. Her ass spanked red. An entire bondage photoshoot. Kelly and Chris spent an hour flipping through the pictures with fascinated horror. Then they found another album. And another.

All of them were filled with photos of gorgeous, naked women. All of them were bound at the mercy of the photographer, and all of them were in a state of wild arousal.

Kelly laughed along with Chris as he mockingly paged through his roommate's "porn stash", but, despite her disgust, she couldn't help but feel a certain... fascination. Kelly had always enjoyed rough stuff in bed, and a dominant, commanding attitude was usually the fastest way to get her hot and bothered. So the concept of a man getting even rougher and stricter with her, even to the point of ropes and whips... it wasn't wholly unappealing.

Once, on Valentine's Day, a previous boyfriend had brought along a pair of fuzzy pink handcuffs, and, long story short, Kelly had cum her brains out. She had been too embarrassed about it afterward to request that they become a regular bedroom fixture, but the idea had always kicked around the back of her head. These pornographic images were bringing those thoughts back in a major way.

So by the time Jerry came back to the apartment to find Chris hooting and hollering at the private pictures on his laptop, was Kelly feeling the tiniest bit horny? Sure. I mean, that was only natural when you had just spent an hour looking at porn, right? It didn't mean anything.

Kelly had never seen Jerry get so angry. Chris just kept repeating his mocking "Sharing is Caring" line, but this time Jerry wasn't having any of it. Jerry started saying something about how those photos were private, and Chris looking at them was a complete breach of the pictured women's privacy. Then he said something that made even Chris stop in confused shock.

Jerry said that when he took the pictures, he had sworn to the women that no one else but him would ever see them.

It took a second for what Jerry was saying to sink in. Unbelievably, Jerry was claiming these were personal mementos he had taken himself. They weren't downloaded porn at all.

Obviously, Chris had called bullshit. There was no way Jerry was getting any pussy at all, let alone the total babes in these photos. The confrontation ended with a mocking sneer from Chris and some condescending advice for Jerry to not leave porn open on his laptop, and to think up some better excuses if someone found it.

At the time, Kelly had been just as sure as Chris. There was no way a weedy little creep like Jerry Hoskins could ever be in a position to take red-hot photos like the ones they had found on his computer. But as the weeks went by, Kelly found that her certainty slipped little by little.

The photos had looked good, but not, like, 'professional porn shoot' good. And if he had just downloaded them from a website, why would he have so many duplicate shots of similar angles, like he was trying to get the shot exactly right? Also, Kelly couldn't help but notice that, despite his introverted vibe, Jerry wasn't exactly a homebody. Whenever she happened to be over at her boyfriend's place on Friday night, Jerry would be "out somewhere doing nerd shit" in Chris's words.

But was he? Or was he out there tying up gorgeous women until they begged for more?

The idea was ludicrous! Even if a woman wanted to be tied up and spanked and played with in that disgusting, fascinating way, why would they pick a loser like Jerry to do it with? The idea of Jerry dominating and controlling a woman much hotter than himself stuck in Kelly's craw. For some reason, the idea of any woman submitting to a loser perv like Jerry was obnoxious to her.

She couldn't stop thinking about it.

After obsessing over the strange photos for a week or two, Kelly decided to do a little research of her own. She started secretly looking up BDSM porn. Just to see how she felt about it. Well, that was her original plan at least. Before long, Kelly found herself masturbating to hardcore BDSM porn on a daily basis.

And the worst part was that sometimes, just as her orgasm was gripping her, she would picture Jerry doing the things she saw in the video to her. It wasn't that she was attracted to the little runt. Far from it! That was sort of the point in fact. The idea of submitting to a man so far beneath her was so humiliating it felt filthy and taboo in the kinkiest possible way.

Eventually, Kelly decided that she had to try it.

Not sex with Jerry. God no! She wasn't that horny or dumb. But she had to get a taste of the bondage she was seeing on her screen every night. Kelly had always been a lot smarter than Chris. That was the way she preferred her men: big, handsome, and dumb. So it wasn't exactly hard to subtly bring him around to the idea of trying some kinky bondage sex with her.

But frustratingly, Chris simply wasn't good at it. He didn't have the patience. Kelly would try to coach him through tying her up with some basic knots and teasing her, but every time he would get horny, lose patience, and just end up fucking her before they had gotten to any of the bondage play she craved.

Kelly smiled to herself and hummed a little tune as one hand idly traced circles on her snoring boyfriend's back. Luckily, she had a foolproof plan. She had thought up a way that she could get exactly what she wanted from Chris without him getting frustrated. Just in time for their one-year anniversary, too! It would be a sweet little celebration for both of them.

And hopefully, when she got the satisfying taste of the domination she craved, she would stop having those humiliating fantasies about her boyfriend's loser roommate.

...

Three weeks later, Kelly grunted, straining awkwardly to position the mini-whiteboard just right: propped up against her tits so that the message was perfectly legible.

"Happy Anniversary, Baby! Enjoy!" Surrounded by cute red hearts.

There, now she just had to get everything else into place. Kelly was giddy with excitement. She could already feel her pussy moistening with anticipation for the night to come, and her nipples had been hard as a rock for hours. She slipped the blindfold into place and tightened her ball gag, then slipped her right arm into the waiting loop and tugged the binding tight.

A slight thrill of anxiety suddenly washed over Kelly. She gave the ropes binding her wrists and legs a few experimental tugs. Shit. She really was helpless. She couldn't get out even if she tried. Kelly forced herself to relax, telling herself she was being silly. She had timed it perfectly. Jerry hadn't been home until late all week long, and Chris would get home from his last class in five minutes or so, just like he did every Friday. When he got there, Chris would find his horny girlfriend tied up on his bed: arms bound, legs splayed and tied, blindfolded, gagged, and soaking wet. Pre-wrapped and ready to fuck, no boring knotwork required on his part.

It was the perfect setup for them to both get what they wanted.

She just needed to wait until he walked through that door.

Any minute now.

...

"Come on, man," said Kyle, jerking his head to the side to indicate Chris should join them. "We're going to head down to the Smokehouse and have a few."

Chris hesitated for a second. "Uhhhh, not sure I can," he said. His voice was gruff, trying to cover up his embarrassment. "It's... well, it's me and Kelly's anniversary today."

The group of guys burst into incredulous laughter. "Are you fucking serious dude?" crowed Kyle as Chris looked on with a scowl. "You guys aren't married! You can do whatever you fucking want. Come have a few beers with us, then go home to your girl."

Chris reddened as the laughter died down. Kelly had told him that he should hurry home today, but there was no way he was going to look pussy-whipped in front of his friends. Kelly would understand. His reputation as a man was at stake here. He would just shoot her a quick text and be a few minutes late.

"One beer," he grunted irritably, raising cheers from his buddies as they slapped him on the back.

"Yeah, yeah," said Kyle, "One beer, buddy. That's all."

...

Jerry returned from the club in a foul mood. This evening's sub had canceled on him at the last minute, and now he had no plans at all for the evening.

He wasn't used to getting blue balled nowadays. Because, surprisingly even to himself, Jerry had sort of become a hot commodity at his usual BDSM club, and was usually booked straight.

When Jerry first worked up the nerve to go to one of the city's BDSM clubs as a freshman, he had basically expected to be kicked out immediately. But somehow that hadn't happened. The older woman who ran the place decided he was cute, and took Jerry under her wing.

And, shockingly, it turned out that Jerry Hoskins was sort of a savant at domination. When he finally convinced (begged more accurately) one of the club's regular submissives to give him a shot, he had gotten good reviews. After he got more practice and experience, good reviews turned into rave reviews. It happened over and over again. A submissive would categorically reject the idea of submitting to a weedy little nerd like Jerry, then would get persuaded to try him out based on the buzz around the club, and then would beg him for another session after having their mind blown.

As fun as the attention and eagerness of the subs was, it wasn't actually complimentary. These women definitely weren't lining up to date Jerry. He was well aware that part of the effectiveness of his sessions was the humiliation of submitting to someone as seemingly pathetic as him. But Jerry didn't care. How could he when gorgeous women were lining up to have sex with him? It was like he had somehow won the lonely nerd lottery.

Well, except for tonight. Tonight he would be the lonely little jackoff that Chris and his stupid hot girlfriend thought he was. Speaking of Chris, Jerry had hoped that his roommate would be gone, but he could hear noises from Chris's room. Fuck.

Jerry decided that what he needed right now was a nice, hot, relaxing shower. There was no better way to wash away the stress and disappointment of the evening. He was halfway through and starting to feel a little better when he noticed that his bottle of shampoo was suspiciously light. Of fucking course Chris had used it all up, once again completely ignoring the sharpie on the side.

That fucking did it. Jerry was in no mood. With fierce, jerky movements, he turned off the shower, snatched his towel off the rack, and stormed over to Chris's bedroom to give that fucking asshole a piece of his mind.

Jerry swung the door open, ready to burst into an angry tirade. Then he stopped dead. His eyes widened and he unconsciously held his breath, still-warm droplets of shower water sliding down his towel-clad body.

Kelly's North's tight, petite body was completely naked, bound, and displayed on his roommate's bed. Shiny trails of arousal shone on her inner thighs, framing her perfect, juicy little pussy. The soft dormancy of her nipples indicated that, at this point, the fun of self-bondage had worn off a little, but her shapely tits, jiggling slightly with the heaving of her chest, were still a sight to behold.

"MMmmmfff!" grunted Kelly through the gag, straining futilely against the self-bondage she had trapped herself in. Jerry struggled to respond for a moment, just obsessively running his eyes over the alluring sight in front of him. He knew what the right thing to do was. He should close the door and forget he ever saw this, as hard as that might be. Maybe he should even call Chris and tell him to get his ass home and give his poor girlfriend a hand.

But the empty shampoo bottle was still rattling around the back of Jerry's mind. And the empty milk jug. And how he had been cock-blocked tonight. He thought about the mocking, disgusted expression Kelly had worn around him ever since she had gone snooping through Jerry's private pictures with her boyfriend.