Breakup Sex

I lay in bed next to Serena, wondering how long I had to wait to touch her. We'd had a huge fight on the way to the beach, and had been studiously avoiding each other since. I don't even really know exactly what the argument was about. Sometimes, she just seemed to want to be mad at me, any reason would do. I think that I was some kind of weird rebellion for her. I didn't examine my motivations in the relationship too closely. When I shone a light on them, I was inevitably kind of disgusted with myself.

Serena and I had been dating on and off for about a year. She was a debutante, had gone to a fancy private preparatory high school, where she had worked her way through a variety of boring guys with Caesar haircuts in polo shirts. In college, her boyfriends before me had been almost interchangeable. Her regular wardrobe included real pearls; white ones for everyday, black ones for formal occasions. She was always perfectly coiffed in lots of designer pastels.

In contrast, I went to a public high school, and I was a fucking nerd. Hell, I was captain of the Mathletes, and there was only one other guy on the team. We'd had nothing in common except no friends and good grades. Looking back at the photos, I can see that my mother's home haircuts did me no favors. I was pasty and skinny, with thick, smudged glasses. My mom didn't believe in contacts, and she flat refused to pay for them. She was proud that I was a dork. My mother thought my lack of conformity showed strong character, and she desperately wanted to keep me sheltered, firmly under her thumb. I'm majoring in economics, but I added on a minor in psychology to try to understand her raging borderline personality disorder.

My dad was so avoidant that he was a nonentity, then he unceremoniously died when I was ten. I didn't have any siblings. I wasn't allowed to have hypothetical friends over, or go to their houses (if I'd ever been invited anywhere). I would have had no idea what was normal, except that I read all the time.

When I graduated, I was 140 pounds overstretched on a 6'2 frame. The summer before college, I completely reinvented myself. I was determined that as an adult, I would finally have real friends, people that I actually liked, who really knew and liked me back. I worked out for hours in our hotbox of a garage, lifting weights. I made money mowing lawns so that I could afford lenses and a new wardrobe. My older cousin, Caleb, taught me to play guitar and helped me pick out some new clothes. I think he felt sorry for me. His girlfriend was in hair school, and she gave my light blonde mop a good cut.

By the time I left for school, I looked like a different person. I'd filled out and gotten a tan. My clothes actually fit. My mother didn't understand my transformation, and when her inevitable histrionics failed, she emotionally bailed on me before I could physically leave her. I moved eight hours away, and immediately loved college. It was everything that I had hoped for. I finally felt good about myself. My grades were perfect, and my dad's life insurance was footing the bill. My new friends were supportive, and so refreshingly easy to be around. Pretty, popular girls were suddenly interested in me.

Settled in the dorm, I found (to my slight chagrin) that I didn't really miss Mommy Dearest. However, I still had this nagging tone in the back of my head that sounded annoyingly like her, telling me that my new life was all a carefully crafted ruse, a fragile house of cards that could easily fall to pieces at the slightest disturbance. Sometimes, when we were drunk, I talked about my fucked up family with Shaun. He understood.

At the beginning of our relationship, I liked being seen with Serena. It was fun, to go to events and dress up, to have her on my arm. I felt chosen, fancy. However, behind closed doors, she could be volatile. Her moods reminded me of my mother, which set off tiny internal alarm bells, but the instability also felt hauntingly familiar, oddly normal. Appearances were important to her, so she never lost control in public. It was almost as though I had imagined the fits of temper whenever we were with other people. I found through trial and error that Serena was repressed everywhere but in the bedroom. I admit that some part of me liked the dichotomy. It felt like I only got to see the real her when I was fucking her.

My girlfriend hadn't ever meshed with my friends. If I'm being honest, I didn't really care for her sorority groupies either. They were all wealthy, cosmetically enhanced girls with too much statement jewelry. It was always a little awkward, that the only thing we had in common was each other, and that was tenuous at best.

I'd noticed that it put Serena on edge to watch Bryan and Allison together. I think that they made her feel insecure about our relationship. I mean, it could be hard being confronted by the perfect couple. I got it, sort of, but we had our own thing. I couldn't figure out why she had to compare us to other people all the time. Really deep down, I strongly suspected that she might have a crush on my buddy.

Serena hated Tyler's new girlfriend on sight. Lisette was gorgeous, tall with natural auburn hair and a lithe, effortlessly proportioned figure. She was also incredibly laid back and sweet. I think it made my girlfriend jealous that Allison and Lisette had immediately hit it off. Allison was the closest thing that I had to a sister, but she and Serena were like oil and water. They just didn't mix.

After Allison met Serena for the first time, she told me to watch myself. I had brought my new girlfriend over to their place for dinner, our first (and last) double date. They made lasagna, a salad, and a chocolate cake. As usual, Allison was the cook; Bryan was the baker, and they cleaned up together, kissing and dancing unselfconsciously to country music in their little galley kitchen. I noticed a certain amount of unusual coldness from Allison after I excused myself to hit the head before dessert, but I chalked it up to weird girl politics.

The next day, when I went over to do the postmortem, I had gotten offended by Allison's comment. I remember snapping at her to elaborate. She bit her lip guiltily, like she didn't want to hurt my feelings, and took a deep breath.

"I don't trust that bitch. She's a snake in the grass. I think that girl is going to try and make you into something that you aren't. Without sex, what do the two of you really have in common? Did you notice how she kept correcting you? When she wasn't doing that, she just sat there, looking bored, or inappropriately staring at Bryan. Serena didn't ask us one question about ourselves. When I tried to take an interest in her, she looked at me like I was something disgusting on the bottom of her shoe."

I could tell that her comments weren't about jealousy. Allison didn't care how Serena had looked at Bryan. She wasn't at all insecure. She and Bryan were too solid, too in love. Her obvious lack of envy actually kind of smarted. I was chagrined. I already knew better. They'd shown me exactly what real love looked like, my self esteem was just too low to go after it. It was easier, safer, to settle. I already knew that Serena was prone to intense fits of jealousy. For the first time, I fully realized that it was a character flaw, a clear example of the fault lines in our relationship.

I remember that I shook my head, thinking hard about what Allison said as I mentally replayed the evening. I had looked over at Bryan beseechingly for confirmation, support, something.

He'd just sighed and shook his head resignedly. "Dude, relationships work when people are able to be themselves. That's all I'm saying... I really hate to be this guy, but please don't bring her over here again."

When Serena met the rest of the guys, they had all been noncommittal, uncharacteristically quiet. After she left, Tyler had just said that he hoped she was making me happy. Shaun thought she was spoiled, but that characterization didn't really bother me; he tended to be overly critical of privilege. Seth had seemed like he was going to say something, but I'd seen Bryan give him a warning look and he'd swallowed the words and made a stupid, unrelated joke instead. Since then, they all tended to nod along, performatively supportive whenever Serena's name came up.

Serena gave as good as she got. She had all kinds of criticism about them, and was constantly pouring proverbial poison in my ear. My girlfriend felt that Seth was too glib, that he tried too hard. In the next breath, she would bitch that Shaun was too quiet, that his natural brooding was off-putting. She just didn't seem to like people very much, so when she wanted to spend time with me, I felt validated in a weird, intangible way. That feeling unfortunately overrode a lot of my reservations.

We had a well-worn pattern. Serena would pick a fight over something stupid and inconsequential, seemingly for attention. I would inevitably take the bait; we'd yell at each other until we got tired, then she would sulk. Sometimes we broke up. The arguing almost served as foreplay. When Serena was prissy, difficult and insulting me, it somehow turned me on, which consequently made me ashamed of myself.

I had been a little worried, bringing her on the trip with my friends, but I figured it was time to create some make-or-break circumstances. With all of us stuck in the same house for a week, she'd either have to bond with my friends and be able to get along with them, or the experience would unequivocally show me that it was time to end the relationship for good. We were all about to graduate. I mean, it wasn't like I was going to ditch my friends for her. Over the last four years, they'd become my surrogate family.

Shaun and I spent Thanksgiving with Tyler's family. We went to Allison's parents' house with Bryan and his mom at Christmas. Every New Year's Eve, Seth's parents threw a crazy party wherever they happened to be living. We all hung out with his mom's military buddies, his dad's stoner friends, great people that they'd connected with while moving all over the world. Individually, they meant a hell of a lot more to me than Serena; collectively, I couldn't ever imagine my life without them.

Since I'd gotten back together with Serena two months before, I had been viewing my relationship with a confused amalgamation of alarm and priapism. Every time I tried to break up with her, Serena seemed to sense my ambivalence, and she reacted by fucking me seven ways to Sunday. It felt like I was selling my soul for pussy.

Hoping she was over our disagreement, I experimentally ran my index finger up and down the inside of her arm. When Serena didn't pull away, I leaned over and kissed her. She lay there like a dead fish for a minute, clearly still punishing me. (It had started over Pepsi instead of Coke from the drive thru. I don't know why I let her push my buttons. Who gave a shit about soda?)

I put my hands on her breasts, under her shirt, giving her plenty of time to say no or push my hands away. Other flaws aside, Serena had a great rack. Her ballet career had prematurely ended when she went through puberty. Her pendulous breasts always looked huge, buoyant on her short frame. I liked to watch them bounce.

I got on top of her, and she belatedly started kissing me back, opening her mouth for my tongue. I angled my hips between hers and started talking dirty in her ear, saying all kinds of perverted shit, anything that popped into my head. I wanted the other couples to hear us through the walls. I could hear them fucking, and it was turning me on. I figured that I should return the voyeuristic favor.

I talked about the time that she had pulled me into a lingerie store and had given me a fashion show in the deserted dressing room. I remembered all the bright, colored lace decorating her bronzed skin, the teasing glimpses of her nipples every time she changed. Finally, I couldn't wait anymore, and I tore off the panties that she was trying on. I went on about fucking her from behind as she clung to the top of the shaking divider, the way I could see her creamy cum coating the base of my cock with every stroke, going so deep that I didn't know where I ended and she began. When we were finished, the previously pristine pink lace was in shreds, covered in her juices and my cum, completely ruined. I had to buy them. The cashier looked horrified when I pulled off the tag and handed it to her to scan. I didn't think she'd want to touch the actual fabric. I remember being equally shocked when I saw the high cost of a wisp of lace, but it felt worth it at the time.

While I told the story, I kept moving against her, getting Serena hot and bothered, slippery and wet, ready to beg for my fingers. I punctuated my story with practiced nips at her neck. I was careful not to create any marks, following her well-established rules. My girlfriend didn't like me to leave any evidence behind when we fucked. I put my tongue in her ear and she practically purred.

It isn't that I have a problem going down on women. The smell, the taste, the squeeze of their thighs around my ears. It's dead sexy. However, through much trial and error, I have found that I am much better with my hands.

When I fingered my first girlfriend, Jenny Clapp, she was kind enough to tell me (in no uncertain terms) what I was doing wrong. Jenny said it felt like I was attempting to start a fire with two uncoordinated twigs, rubbing her like I was trying to find a secret passageway to nothing. I was also nowhere near her clitoris at the time. I won't lie, at the time, my ego was bruised, but then, like the saint of fumbling teenage boys that she was, Jenny taught me exactly what to do. I know that all vulvas are different, but I can tell when a woman is really having an orgasm, and Jenny's tutorial has yet to fail me. (Bless you, Jenny Clapp, wherever the hell you are.)

One thing that I really appreciated about Serena was that she would talk dirty with me. A lot of the women that I had been with seemed too insecure or shy to really engage. They didn't want to tell me what got them off, what they fantasized about while they touched themselves under the covers. I think part of it was that I haven't had that many real relationships. When I got to college, I was interested in playing the field, fucking as many women as possible, making up for what I imagined I had missed out on in high school. My philosophy was also somewhat self-protective. Often, the women that I really liked didn't seem interested in anything real with me.

For me, sex is so much hotter when there's good communication. I like to know all the twisty, weird little fantasies that get my partners going. Words have this way of erotically wrapping around my synapses and putting me directly in the purported scenarios. Maybe I'm more like a chick that way; I don't know. Regardless, I think that's the real reason that Serena and I have backslid so many times. You get in a psychological groove with someone, and it's daunting to think of having to be so sexually open with someone new. I'm into some pretty dirty stuff. It has been a little much for some of the women I've been with.

I segued into talking about the time that we fucked on a rocking chair on the porch at her parents' lake house. I sat there and she straddled me, swaying the chair rhythmically back and forth with her feet. Then, just as we'd hit a fever pitch, Serena had leaned away from me; she put her hands on my knees and arched her back, completely changing the penetrative angle. When I thought it couldn't get any better, she did Kegels, effectively massaging my dick until I came while looking out at the clear blue sky, smelling air washed clean with a recent rain.

As I talked, my fingers squelched inside her. I rubbed her clit with my thumb. I could tell that Serena was close. She was biting her lip. Her eyelids were squinched tight, and she seemed lost in my words. Serena's look wasn't natural, or at all effortless. She had a blob of a nose, thin lips, and a sharp chin. She wore a lot of make-up and false eyelashes. The pieces came together to form a perfectly nice picture, but there was still something about her features that always looked inherently displeased. Maybe that was just the way that she looked around me.

No matter how many times I managed it, I always felt immeasurably proud of myself whenever I made a woman cum. However, this time, when she involuntarily tightened around my digits, I felt strangely disconnected. Usually, when we hooked up, Serena kept her eyes open, almost locked on mine. This time, she seemed more interested in listening to the fantasy that I was providing. It didn't seem like she was picturing me. When her orgasm passed and she stopped moving against my fingers, Serena didn't open her dark eyes, but she started talking.

"Remember our first time together, Marc? We met at that party at ADPi. I saw you, leaning against the wall, drinking cheap beer from the bottle. I could see your Adam's apple bob every time you swallowed. You were talking to Seth; both of you were kind of laughing. I knew then that I would be taking you home, that you would be fucking me after the party. I texted my roommate that she'd have to clear out. Have I ever told you that before?"

She wound her body around mine, and spoke right in my ear as she fondled my cock, giving it little irregular squeezes that made my skin tingle.

"Looking at you, I thought that you would be really good at eating pussy."

Serena kind of chuckled then. It was a hollow, antagonistic snort.

"I mean, obviously I was completely wrong. I saw what I wanted to see. You always finger me. I don't think you've ever even tried to go down on me. Your sexual skills are pathetic."

"Hey, you always cum..."

I pouted, but Serena didn't seem to care. She ignored me and opened a rubber with her teeth.

As she pinched the reservoir tip and effortlessly rolled it over my erection. She said nonchalantly. "How would you know? Maybe I fake it."

I knew for a fact that she didn't. Serena was a terrible actress. I'd seen her in a bit part in the school's latest (pathetic) attempt at theater, and it took everything that I had to tell her she did a great job with a straight face. She couldn't lie for shit.

She got up on her elbows and knees without prompting, rocking her slim, fake-tanned ass back and forth invitingly. I could tell that she didn't want to look at me. Running my eyes over her body, I tried to think of something, anything, new that I wanted to do with Serena. When nothing came to mind, I thought harder, trying to land on any experience that I wanted to repeat. My mind was a total blank.

I realized that every experience we were talking about was in the past. We were just passing bastardized fantasies back and forth, trying to recreate an airbrushed version of something that had never really existed. I couldn't figure out when the things that used to irritate me and turn me on in equal measure had hardened into sharp shards of hate, but I suddenly, unequivocally, realized that we were having break-up sex. It was over for me.

However, apparently, Serena had at least one more thing that she wanted to try with me. I was shocked when she said flippantly, "I want you to hate fuck me. Make me feel cheap, like this sham of a relationship."

That was interesting. Typically, during sex, she forced me to play up a faux connection, to feign an emotional closeness that I'd never actually felt with her. I can't pretend that the sudden raw truth didn't turn me on. I liked rough sex. My cock bobbed with the beat of my heart, and I figured that one more for the road couldn't hurt.

I lined up behind Serena and twisted her long hair tightly in my fist. I pulled on the rope of her dark ponytail, and her back arched. When I slid inside her, I could feel how warm and tight she was, even through the condom.

I had always enjoyed fucking Serena from behind. Looking down at the pronounced knobs of her spine. I belatedly realized that it was because in that position, I didn't have to see her face, or to arrange my features into an expression that pleased her. I think by that point, we were both already imagining that we were with other people, people we actually gave a shit about.

That night, watching my friends with their girlfriends, I had viscerally wanted what they had. Bryan and Allison were always enviable, but now both Tyler and Seth were obviously going down for the count with their new girlfriends. Seeing them so happy, I starkly knew I couldn't love Serena like that. Worse, it was just occurring to me that I didn't even particularly like her. I wanted more. I was starting to realize, finally, that I deserved it.

Splayed below me, Serena started talking again. "I walked right up to you, and you stared down the neck of my yellow dress for the rest of the night. I was picturing your cock the whole time we talked. In my mind, it was really thick, kind of squat. I was right about that."

She turned her head and sneered at me. "You practically have a fucking chode."

I remembered that night vividly. Serena was right; I had kept trying to see through the sheer layers of fabric that made up her dress. However, I didn't appreciate her characterization of my dick. It is fucking thick, and I'm a grower, but my cock is still a solid seven inches when erect. There's nothing squat about it. I could tell that she was trying to piss me off.

Her superior attitude made my blood run hot. I interrupted her, going for broke. "How does my squat cock fucking feel now, bitch? I fucking dare you, insult my thick dick as it fucking splits your inadequate pussy in half. I'm going to make you scream."

I knew that I would want to parse the conversation, to remember the exact dip of her hips, the way her molten insides squeezed at me, but there would be time for that later. I was going to give her exactly what she had asked for. Our collective breathing was labored. Serena kept up her insulting monologue through gritted teeth, but she panted harder with every one of my punishing thrusts.

"That's right, try to fuck me good with your pathetic little chode. I never actually liked you, did you know that?! It just amused me that you tried so hard, and I wanted to see how many free dinners I could get from you. I mean, your dirty talk thing was mildly entertaining for a little while. I can't believe that you like watching footjobs. I was especially amused when I found your lactation porn. God, your mommy issues are so fucking banal. You're so boring, just like all of your basic little friends out there."

I drew back like I had been slapped.

"Clear your browser history, moron."

The degradation was actually doing it for me. Humiliation and embarrassment laced with arousal, and I suddenly wanted to make her pay, to show her that I was a man. At that moment, I realized exactly how much I viscerally loathed her.

"You didn't think my friends were so embarrassing when you pathetically threw yourself at Bryan after we broke up last time, at the Sig party. Yeah, he fucking told me all about that. Allison wasn't the least bit threatened by you. She actually laughed at the idea of him looking at you twice."

Serena seemed undeterred. Her delivery was that of an auctioneer. "My parents were so embarrassed that I was seeing you. They literally reupholstered the dining chairs because you sat on one of them. Every time I've fucked you, I've thought about their horrified faces. It's the only way that I've ever been able to get off with you. You can't even be rough with me the right way, you cuck bitch. Show me how much you fucking hate me. Slap my ass!"

I pulled back and smacked her ass until both cheeks were flaming red. With every whack, she tightened around me. I didn't know which I wanted more, to prove my sexual skill, or to deny her. I thought it would piss Serena off more to have to remember that I had made her cum, whether she wanted to or not, whenever she remembered the death knell of our pretense of a relationship. Decision made, without any warning, I shoved two wide fingers in her ass. Then, I snaked my other hand around and rubbed her clit.

"You like my fingers now, bitch?"

I was repulsed by myself, and her.

She shrieked, "I'm going to fucking cum!"

The abject relief of knowing that I didn't have to fake a connection with her anymore made me cum with her, hard. Sweat dripped down my forehead and landed on the handprints still decorating her ass. Pathetically, the break-up sex was probably the best fuck we'd ever had together. Her orgasm finished before mine. I was still firing off my last shot when Serena pulled off of me, got up without a word, and stalked off to her bag.

I lay there, milking the final drops of warm jizz from my softening piece. I kept breathing hard as I replayed the sex and every shitty thing we had said to each other. In my post-nut clarity, there was a complicated mixture of anger at her, sweet solace knowing that we were over, and a healthy dose of self-loathing.

Serena dressed in immaculate pale blue cashmere sweats and black Gucci slides, checking her bag to make sure she had everything.

I glared up at her. "Why did you even bother to come here with me? Couldn't we just have broken up at school, without the audience?"

Serena tapped her foot impatiently. She breathed out in a practiced huff. "I've been trying to psych myself up for this trip for a month. After just one night, I fucking knew. There's no way in hell that I can stay in this shitty little house, with THOSE people, and I definitely can't be with the idiot who actually wants to be here. Bye, Marc."

We'd broken up so many times, but this time felt entirely different, terminal. All that was left between us was contempt. Serena walked out, dragging her overstuffed bag behind her. A few seconds later, I heard the back door open and close with soft finality. I guess I should have just been grateful that she didn't slam it.