I Bet You'll Like It

Author's note: This is a work of fiction. All characters are eighteen years or older. Don't expect realism and you won't be disappointed when you don't find it! Enjoy!

*****

"So," Judy said after gobbling down a huge mouthful of pizza, "what exactly did you find in her anyway? You could do so much better..."

I shrugged, taking a sip of coke, keeping my gaze on the TV. I could feel my roommate's piercing stare boring into me as she sat by my side on the couch.

"Come on, Judy," I said, "do we really have to talk about this? It's over, okay. She's a shallow skinny bitch and I'm happy to be done with her."

"Duh, of course you are. She was mean and selfish and boring, and you're nothing like that. But that's my point. Why, Greg?"

"Why what?"

"Why are you still bothered? Something about the whole Cindy business is still bugging you, I can see it. It's been three weeks now, and I tried not to pry too much, but..."

I snorted at that. "Yeah, you tried. And failed!"

We both snickered.

Judy and I were close. When I told her about my breakup with Cindy, Judy's reaction was a mix of surprise and barely concealed relief. She had never liked Cindy one bit, saying she was an evil plastic doll. All things considered, Judy was right. After Cindy unceremoniously dumped me to hook up with a braindead frat boy, Judy was all sympathy and cuddles with me, even more than usual. She showered me with attentions, hugging me and getting on her tiptoes to give me her typical smacking pecks on the cheeks at every chance. It was nice, very nice indeed. And, in truth, Judy had done a fairly good job of keeping her characteristic curiosity in check, respecting my wish not to discuss Cindy anymore. So far, at least.

"Seriously though," Judy went on, unperturbed by my defensive sarcasm, "I can see that you're still thinking about her. You're not sad like, the-love-of-my-life-left-me kind of sad, of course, because she was definitely not the love of your life. But you do miss her somehow..."

I chuckled at that, still trying to focus on the rerun of Game of Thrones. Judy could read me, I had to give her that. And I was happy to let her read me. Judy was cheerful, with a relaxed and kind attitude that put even a brooding loner like me at ease. She was also very smart, with a quick ironic wit that I couldn't help but love. Most importantly, she had a talent for making me feel comfortable.

All things considered, I wasn't really upset that she was asking me about my not so recent breakup. She was right, after all: I was still thinking about Cindy, in a way. I actually wanted to talk about it, but I was embarrassed. Still, if I was ever going to tell anyone, Judy would be the one. Sighing in resignation, I turned to my pizza-munching roommate.

Judy's pale gaze locked on mine instantly. Her eyes were as bright and spellbinding as ever. I lost myself in them for a moment, trying to finally define their color and failing, as always. Pale blue? Light green? Ice gray? Impossible to say. But I was glad I couldn't tell. It gave me a perpetual reason to stare at Judy's sculpted, delicate face and look into her sparkling orbs.

"Fine," I sighed, snapping out of my momentary trance, "you got me. I do miss Cindy, sort of..."

"I knew it! Now, define 'sort of', please."

I squirmed at that. "You really wanna know?"

She nodded her head, making her long dark ponytail bob. She had a curious yet sweet smile on her luscious lips as she kept her inquisitive eyes fixed on mine, waiting patiently.

"I don't really miss Cindy herself. Just, well, parts of her... Things we did, uh, one thing mostly..."

"Yeah, 'things'... So we're talking about sex, right?"

"Yes. More specifically," I said, trying not to blush like a schoolgirl, "anal. I miss her ass, that's all."

Judy raised an eyebrow, grinning. "She didn't have much of an ass, Greg, come on. Way too scrawny."

"True," I chuckled, "but she let me fuck it! Not that she was eager," I added, feeling better now that I could just let this recent obsession of mine out in the open. "I had to beg her and then she'd complain a lot that she didn't like it and it hurt too much to enjoy it. Still, it got me hooked. That's what I think about when I think about Cindy these days: the two times I got to fuck her ass. In fact, that's pretty much why I stayed with her at all, it's not like I loved her..."

Judy took a big gulp of coke from my glass and nodded sagely. "Yeah, well," she said, looking at me thoughtfully, "I guess that makes sense. I mean, now I get why you're still hung up. But you don't need to sulk, Greg. Other girls might give you their asses too. Some wouldn't even make you beg at all. And," she concluded with a teasing smirk, "a few of us might actually beg YOU to buttfuck them and they'd cum like crazy with your cock in their ass, because they like it, a lot."

Judy winked as she purred out 'a lot'. I stared at her, my mind reeling. Candid conversations like this weren't exactly unusual for us, but what she was suggesting definitely was. Unless I misunderstood, of course, or she was messing with me, both of which were possibilities worth considering.

"You mean," I mumbled, shifting to sit more comfortably while trying to make the growing bulge in my pants less obvious, "you like it... In the ass?"

Judy shrugged and looked away, suddenly bashful. Her pale cheeks reddened slightly. That was a first, I thought, intrigued by her reaction as much as I was by the subject.

"Yeah, I kind of like it," she said, still avoiding eye contact, speaking quickly, an uncharacteristic nervous edge in her soft voice. "I never tried the real thing, not yet. Just my fingers and my dildo. But if I touch my clit while I play with my butt, I cum like crazy. And I mean, nuclear bomb crazy."

"Oh. Okay," I said, my boner now achingly stiff and my mouth suddenly dry. Judy was still looking away, biting her full lips, when I recovered from my brief shock and teased her: "So that's what you do with your boyfriend during those videochats, uh?"

Judy laughed as she turned my way, slapping my arm playfully. "I told you a million times, he's not my boyfriend! He's just a guy I know from back home. We go way back and we're just keeping in touch."

"Yeah," I pressed on, "I'd say 'touch' is the key word..."

"Well, yes, I finger myself when we chat," Judy pouted, raising her delicate chin in an exaggerated pose of hurt dignity that made her words comical despite their hotness. "But that's because he lets me watch while he and his girlfriend have sex. It takes me back to the times we used to do it together, the three of us."

That hit me, hard. I knew Judy had some sort of virtual fuck-buddy back home in Oklahoma with whom she got together at least once a week. She had told me about this herself after I heard her scream out in climax one night and then asked her over breakfast if anyone else was going to join us. Giggling and shaking her head no, Judy told me she was just fooling around with a friend in videochat. She hated that I referred to this mysterious guy as 'her boyfriend', so of course I called him that at any given chance.

I blinked my eyes before talking. "The three of you? You mean you, this guy and his girlfriend... You used to have threesomes?!"

Judy laughed and nodded. "Yeah, sometimes. We grew up together, the three of us. She's my best friend and the two of them have been a couple since forever. After they started to have sex, they kind of invited me to join in. It was pretty natural, I guess, at least it was for us. He was the one who took my cherry, and we did some stuff all of us together sometimes, but mostly I just watched the two of them, like I do now. They are really in love though, like, actual soulmates and stuff."

I was blown away. "Wow, Judy," I gasped, "that's... So hot! I had no idea..."

She giggled and took another big bite off her slice of pizza. "You never asked, Greg. I bet you never thought I was into butt stuff either, eh?"

"No, not really. Let alone group stuff!"

"Well," she said, grinning mischievously, "I had got you figured out for an ass man a long time ago. Of course," she smiled, "the fact that you stare at my booty all the time gave you away easily."

It was my turn to redden now, but I was smiling as I did. "Yeah, guilty as charged. In my defense though, I'll just say that your ass is absolutely epic, I just can't help myself. And," I added with as serious a face as I could muster, "your tendency to wear boy shorts around the house is another extenuating circumstance I urge you to consider."

We both had a big laugh. After that, there was silence for a while as we looked each other in the eye. Then I chuckled and shook my head.

"What?" Judy asked.

"Nothing, you got tomato sauce on your nose."

"Oh," she said, crossing her eyes comically in an attempt to see the tip of her pretty nose. Then she giggled and leaned in, brushing her nose against mine. "So do you now!"

Judy lingered just a second with her nose pressed against mine. I could feel her hot breath on my lips. Maybe it was our talk, but even though we were pretty cuddly as a rule, this was the first time I felt a palpable sexual tension between us. It lasted just a second, then Judy gasped. With the corner of her eye she had caught something on the screen.

"Oh my god, Greg! We were about to miss the scene where Jaime Lannister bones his sister!"

We both chuckled and turned to the TV, snuggling closer on the couch, the smears of tomato sauce cooling on our noses. My cock was still painfully hard, and I could feel a new urgency in Judy's clutching hug as she rested her head on my chest.

We settled in our usual cuddling position and focused on the show, silent all through the episode, except when Judy asked me if she could have the last slice of pizza. And of course she could.

*****

When Judy first walked into the apartment at the beginning of the semester, I instinctively liked her. She was a freshman, a year younger than me, and she appeared at our door while looking for a room off campus. It took me all of ten seconds to decide that she was going to be our new roommate.

Even though there were three bedrooms in the apartment, Pete was almost never around. He showed up to hand in his share of the rent regularly, spent two or three days sleeping uninterruptedly in his room and then left again, barely saying a word, leaving me to deal with pretty much everything house-related. I'm not even sure he registered the fact that Luke from last year was gone and had been replaced by a pretty freshman named Judy. I didn't mind Pete's absence at all. With the place all to ourselves most of the time, Judy and I soon got very comfortable around each other.

It was normal for Judy to walk naked from her room to the bathroom to take a shower, or to stumble into the kitchen in the morning in just her panties and a tank top, shuffling around and groggily mumbling for coffee like a gorgeous little zombie until I handed her a cup, earning a smooch on the nose and a beaming sleepy smile from her.

It wasn't about exhibitionism or teasing either. From what I gathered, her family was, if not exactly nudist, something pretty close to it. Judy had been brought up not to feel ashamed of her body and of her sexuality. And why should she, I thought the first time I saw her naked, the day she moved in. I'll never forget the moment I saw her there, stepping out of her room, butt naked. She just said "Hey, Greg," while she passed by me, wearing nothing but her bright, warm smile. I couldn't reply as she kept walking down the hall, telling me she was going to take a shower but she wanted to hear all about me when she was done. I barely managed to nod my head as I took in her spectacular body.

Slim and gracefully girlish, blessed with soft curves that made my mouth water, Judy was beautiful. Her tits were round and perky, two perfectly shaped handfuls topped with long, puffy, upturned nipples. Her pussy was smooth and hairless, a pink fleshy flower that beckoned invitingly between her long toned legs. Her ass was definitely her best feature, as far as I was concerned. Heart-shaped, plump yet firm-looking, Judy's bubble-butt protruded roundly from her hips and thighs, jutting out like an invitation to spank it and test its juiciness. I never slapped it, but I did stare at that beautiful curvy ass, a lot.

After that first time, I got to admire my roommate's amazing body again and again, in various states of undress. But, sexy and exciting as it was to gaze at Judy's naked beauty on a regular basis, nothing ever happened between us. We did sleep together once, but I mean 'sleep' literally.

Judy had got a nasty cold and she was running a fever. She was so agitated and deliriously scared of being alone that night that she couldn't even get to sleep. I tucked her in and lay down by her side and she immediately hugged me tight, trembling and whimpering. She was so adorable, so vulnerable and cute, I just wanted her to get better as soon as possible. For a long time, while she shivered and coughed, I soothed her and caressed her hair, kissing her burning hot forehead and singing her favorite songs, trying to sound like Kurt Cobain, Bradley Nowell and Jack White, until she finally dozed off. I quickly fell asleep myself, holding Judy's feverish frame in my arms.

The morning after, her fever broke and mine spiked up. But it was worth it. Judy was deeply moved by the fact that I had got sick trying to make her feel better, she saw it as a noble sacrifice of sorts. Honestly it cost me nothing, it came very natural for me to do something for her. Still, it felt great to see the tender admiration and gratitude in Judy's spellbinding eyes. We spent a couple of nice albeit wheezy days curled up together, sneezing and coughing and watching TV on the couch wrapped up in blankets, until we both recovered. Talk about weird ways to bond.

I know it may sound crazy, but in many ways I saw Judy more as a sister than a friend or a roommate. She was so nice and warm and cuddly, it was so easy for me to get along with her. We synced smoothly on pretty much every level of day to day life. It was kind of a first for me, living in this emotional happy bubble. It was like I always imagined it would be to have siblings, something that I had desperately wanted ever since I was a kid.

As an only child whose one close relative was a taciturn and stern father, it was a totally new experience for me to live with someone like Judy, who came from a big family with lots of cousins and uncles and aunts always around. She and her relatives were very close, and she often talked about them, telling funny stories from her life back home and sharing her happy memories with me, all of which I drank in avidly. With her kind and open attitude, Judy made me feel part of that world and, even vicariously, it felt great and I loved her for it. Right from the start, the feelings involved in the whole Judy situation were even more rewarding for me than the fact that I got to see her naked pretty much every day.

Close and intimate as Judy and I already were, the conversation we had that night about butt stuff marked a turning point in our relationship. Maybe it was the fact that we almost kissed, or maybe it was the subject of anal sex itself and the discovery that we were both into it. All I know is that, in the couple of days after that pizza dinner, there was a buzzing undercurrent of excitement between me and my beautiful roommate.

Nothing out of the ordinary happened, but our daily gestures of affection were charged with a new intensity. Our hugs were longer and tighter, Judy's pecks on my cheeks were much closer to the corners of my mouth and, a couple of times, my usual adoring stares evolved into playful slaps on her fabulous bouncy ass, which made her giggle and purr huskily in turn.

This new sexual tension lasted until Friday night, when something weird finally happened: Judy decided it was time for me to watch Twilight.

For some time now, the fact that I had never seen any of the movies in the Twilight Saga had been a favorite teasing argument of Judy's. According to her, even a self-proclaimed disciple of Dostoevsky like me should know one of the defining pop culture references of our generation, at least in light of its social impact and regardless of its artistic merits. It was always more of a joke between us than anything else, but that Friday night Judy made it into so much more.

It was strange from the very start. Judy had me drink two shots of tequila 'to make the incoming visual agony less excruciating', as she put it with a smirk. After downing three tequilas herself, she led me by the hand to her bedroom to watch the movie on her laptop.

"Here, let's not take any chances," Judy grinned as she lay on her side on the bed, her laptop in front of her, "we should be prepared in case you fall asleep from the boredom!"

I was too baffled to argue, plus I was slightly drunk and too intrigued by this turn of events to say anything. Neither me nor Judy usually drank, and her giggles told me that she was feeling the tequila a bit too. She had a mischievous glint in her pale eyes as she looked invitingly at me. I stood by her bed for a second, admiring her.

She was wearing a tight fitting blue T-shirt that showcased her full perky tits and left her smooth tummy exposed. Her gray boy shorts were straining to contain the plump roundness of her ass. I couldn't help but slowly let my gaze roam from the swell of her hips to her shapely thighs, all the way down her long legs to her pretty little feet. She was wiggling her toes, a tell of hers that I knew to mean she was either nervous or excited.

"Come on, Greg," she murmured, patting the bedspread behind her, "I bet you'll like it..."

I just chuckled and joined Judy on her bed, spooning her and looking over her shoulder at the screen as she started the movie. I stifled a moan as Judy wiggled her luscious ass, pressing her juicy bubble-butt right against my tenting groin. Reaching for my hand with hers, she wrapped my arm around her waist, so that I was embracing her while she snuggled back into me.

The closeness of our bodies and the intimacy of the situation were especially intoxicating after the last couple of sexually charged days. The tequila did the rest. From the very start, I couldn't care less about the film. In a matter of minutes I was rock hard, my pant-clad boner nestled in the crevice of my gorgeous roommate's ass.

"Mmh, seems like you're enjoying the movie after all," Judy purred, turning to look at me over her shoulder. Her full lips were parted and her breath was labored as she asked teasingly: "Is Bella Swan turning you on?"

Wiggling her perfect ass, Judy trapped my erection deeper between her fleshy buns. "Someone is definitely turning me on," I moaned, locking gazes with her, "but it's not Bella."

I reached my hand to Judy's face, cupping her chin in my palm and brushing her smooth cheek with my fingertips. "This was never about making me watch Twilight, was it?"

Judy let out a little laugh, turning her clear gaze away from mine. "Well, no, but it might be..." she mumbled, shrugging her shoulders and thus making her tits jiggle deliciously. She was blushing, which didn't happen frequently but I always found it adorable when it did. "It's just that since we talked about anal sex the other day... Well, I kind of couldn't stop thinking about it."

"I've been thinking about it too," I admitted, brushing a stray lock of dark hair behind her ear.

"Really? Because I actually considered, you know..." she trailed off, arching a thin eyebrow. She blinked her piercing eyes nervously as she sighed and blurted out: "Well, I wanted to ask you, if that's okay, and I assumed it would be since you said you think about buttfucking a lot and you always stare at my ass, which I'm okay with completely, because you're great and I feel so comfortable and relaxed with you, and if I'm going to let anyone do me in the ass you are definitely my first choice seeing as... Oh my god..." she sighed, her cheeks burning red and her whole face flushed with arousal. She looked more beautiful than ever as she ranted away, trying to tell me what we both already knew. "I'm messing this up so bad! It was so much easier in my head, I should have had more tequilas, or less actually, come to think of it... What I'm trying to say is mmhph!..."