[MF] Trying to Rebound with the Worst Possible Person

Around a couple years back I broke up with my girlfriend. The constant feeling that anything and nothing was now possible pureed my mind after ending a long relationship which spanned some formative years. Fortunately, I had good friends that were happy to put me back together. Shaun, Rita, and I had been friends since college and through sheer luck, ended up living in the same city hundreds of miles away.

They had been planning a night out for a friend of theirs, Natalie, that recently went through a rough breakup of her own as a cliché, “get yourself back out there and feel good about yourself” kind of night. Upon learning of my super recent breakup they thought that it would be a good idea to haphazardly staple me into these plans last minute and turn it into a collective “relationships suck” kind of night. They even invited another one of their single friends, Kathy, to make it look halfway planned.

Where the night went from odd to ill-advised is that Natalie’s recent big breakup was with a friend of mine (a coworker specifically, named Matt) that I had set her up with years prior. My now ex-girlfriend and I had hung out with Natalie a few times before they started dating because she was friends with Shaun and Rita, so they must’ve thought it wouldn’t be terribly awkward for me to have a night out partially with a close friend’s ex.

They were wrong.

Having seen Matt in rough shape the last couple weeks because of his breakup with Natalie, this all seemed like an awful idea. All the same, I thought spending some time with Shaun and Rita would be a good way of getting my mind off my own breakup, so I picked the selfish path and resolved myself not to mention seeing Natalie to my friend. If you’re the kind of person that only wants to know just how “selfish” I got without any of the context, I bolded the start of that part below.

We went bar-hopping across the city, knocking back drinks and people-watching. Kathy even got the attention of some good-looking guys, and we gaged how long we stayed at any one bar by how good her prospects were.

We ended up staying at one spot for a while, and after venting a bunch of my breakup grief on Shaun at the bar, I wandered out to the smoking patio to discover Natalie doing the same to Rita. They were both smoking cheap cigars that I have to imagine were bought as a joke. Inelegantly trying to shift the topic due to my presence, Rita half-drunkenly asked me what I thought of Natalie’s hair. She had cut it after the breakup, and her once long, thick dark hair was chopped down to nearly a pixie. Trying to find the most non-committal answer I simply said it looked good.

And it did look good. Natalie was very much trying to make the most of the night. Aside from her short, straight dark hair, she had done her makeup up immaculately to match her ‘going-out’ outfit which consisted of a dark sheer shirt tucked into a skintight leather miniskirt finished off with a pair of black over-the-knee boots that must have been suede or velvet. It was the kind of outfit to make you go “Damn, I can see why my friend is all bent out of shape.”

Natalie gave a sterile “thank you” to my baited compliment about her hair as I pulled a chair up to their table. She continued to inhale from her cheap, fruity cigar as Rita began asking me how I was holding up from my own breakup. My ex had come out with us often throughout our relationship and even got along quite well with Natalie, it felt very much that I had the wrong audience at that moment. Fortunately, it was cut short as Rita caught sight of Kathy doing something of note inside the bar and rushed in mid-sentence.

Thus, the night reached its awkward worst-case-scenario of leaving Natalie and I alone. A sizable silence sat in the air before Natalie made a joke about not wanting to talk about her former relationship for the eighteenth time and that she’d sooner throw herself into nearby traffic if I brought it up. I told her that the same went for me and her dark lips peaked into a quick smile before reuniting with her cigar.

We proceeded to commiserate on our shared situation as Rita apparently remained busy with whatever Kathy was up to. Natalie insisted that she didn’t want anything to do with this night and she was mostly doing it to appease Shaun and Rita. I joked that her outfit told a different story, a joke she missed.

I explained that for someone reluctant to come, she clearly went out of her way to make a statement with her outfit.

Natalie gave me a puzzled look, giggled, and broke eye contact to study her cigar. My gaze fell too, accidentally lingering on the large circular pull-zipper on the front of her skirt which caught the patio light and reflected it back to me as though it was signaling in morse code. Another silence sat in the air, but this one felt strangely tinged with something I couldn’t place at the time.

She broke the silence, again joking about the pointlessness of the night. I gladly took the invitation to complain and our conversation flowed in all directions, both of us laughing and letting our guards down. We agreed that the last thing either of us was interested in was hitting on strangers in a bar and how for all the bad that comes with a breakup, gaining some time to yourself was a plus.

Bluntly, Natalie joked that it was “a shame you can’t have sex alone though.” Her eyes refusing to make contact with mine, she looked down to my shoes, explaining that it was the sole downfall to the peace and quiet. Not wanting to leave her hanging, I followed up about how even hookups would require you to unpack your last relationship and worry about people catching feelings. She smiled wide and nodded.

Enjoying a discussion of breakups for the first time all week, I pushed forward, complaining with a laugh that it was unfair that “the one cure for post-breakup feelings is raunchy sex.” She burst out laughing at the use of the word “raunchy,” to which I tried to clumsily defend before she cut me off, unassumingly resting the heels of her boots on the edge of my chair, and noting that I was right, “the ‘raunchier’ the better.”

I laughed and bit my lip, realizing our awkward small talk had somehow ascended nearly into facetious flirting. I thought of how Natalie and I had probably never talked this much when she was dating my friend, the thought of which struck like a cannonball of guilt to my gut.

Natalie took a hearty sip of her drink, laughed to herself, and pressed on mercilessly, “I mean, is it so much to ask for a guy to fuck you and then just leave?” A guilty smile came across her lips accompanied by an uneasy giggle. She made some follow-up jokes to justify her forwardness as I wondered just how much she’d had to drink.

I responded by suggesting that there are plenty of guys that would do just that. She took a pull from her cigar and peered at me through skeptical eyes. I was wrong, she insisted. Natalie uncrossed her arms, dangling the cigar off the edge of her chair’s arm, her black bra on full display through her sheer shirt, everything else beneath only barely left to the imagination.

Natalie clarified that guys are clingier than you’d expect, that she didn’t want to risk some guy texting her everyday about whatever bullshit she didn’t want to hear. I filled the air as she again took a sip from her drink, telling her she needed to find a guy that knew how to keep his mouth shut. Missing only the beat it took her to swallow her drink, she shot back “Or a guy that has a good reason to keep his mouth shut.”

Unsure if I heard her correctly, I asked what she meant. She said nothing, quickly retracting her legs from my chair, and looking past me, her eyes shifting abruptly from curious to wide. I turned as our friends were quickly making their way over to us. My alcohol-saddled brain caught up to Natalie’s statement like a match to kerosene as I watched her adjust herself in her chair, sitting up straight, wrestling her skirt so it wasn’t riding so high up her thighs.

For reasons I’ll never remember, the group explained that it was time we moved on to a new spot. We made our way over to a tightly-packed bar with a live band playing loud enough to snuff out pretty much any conversation to be had. I thought of Natalie’s less-than-subtle suggestion as I waited for a drink at the bar. I spotted her across the bar with Kathy talking to a couple guys I’d never seen before, smiling and laughing.

It could’ve been anything: Natalie’s outfit, jealousy at the attention she was getting, my deeply rotten moral foundation, or perhaps just the alcohol; but I could nearly hear myself groan internally at the realization that I was highly interested in understanding exactly what Natalie meant earlier, and quite possibly walking down whatever path came with it.

I got my drink and waded though an apathetic audience enduring covers of every rock song from the early 2000s to reach Kathy and Natalie. One of the guys quickly asked if either of the ladies needed a drink which Kathy enthusiastically agreed to, following him to the bar. His friend, presumably a wingman, instead told Natalie it was nice to meet her and what part of the bar he was hanging out in.
Shouting over what must have been some Red Hot Chili Peppers’ song, I asked Natalie if she’d met any “guys that could keep their mouth shut.” She laughed at my codeword and admitted she thought one of them was hot, but was, quote, “the kind of guy that would fuck you and immediately add his reaction to his snap story.”

I laughed having never seen this crass streak of humor in Natalie when she was seeing Matt. She greeted my laughter with a guilty smile as she bent over to fix her boot which must’ve sagged slightly down her leg. Committed to my earlier thoughts for better or worse, I leaned down to her ear to speak over the blaring guitars. “Well, I might know a guy,” I said.

She looked up at me knowingly with an expression that facetiously asked “oh, really?” and told me she’d be “very interested” to know who it was. Before I could reply, Kathy barged into our conversation with her new guy friend. The guy seemed eager to talk to Natalie, whisking her away to the bar, insisting he get her a drink too. An increasingly sloppy Kathy leaned over to me and told me that the guy was curious if Natalie and I were together, and that was likely the only reason he had bought her a drink.

She asked if it was awkward spending time with Matt’s ex. I played it cool and lied that I didn’t know she’d be coming out tonight, and had I known I probably wouldn’t have come for Matt’s sake. Kathy drunkenly made me promise not to tell Matt if Natalie fucked that guy, gesturing to the man buying her a drink.

I told her that “I knew how to keep my mouth shut.”

Time passed as I hung out with Shaun, Rita, and Kathy; at one point breaking off to use the bathroom. Upon coming out I saw Natalie waving goodbye to the guy and his friends, the whole pack of them unabashedly staring at her ass as she walked away. I write that as if I’m all high-and-mighty, but I was guilty of the same throughout the night.

It was a really tight skirt.

She caught sight of me and walked over. I asked if he was another “snap chat guy,” to which she laughed and scrunched her lip as if to say “almost.” She seemed to calculate her words, before announcing he was more the kind of guy that would “finish on your chest and then want a high-five after.” Natalie laughed loudly and told me that I ought to see my face when she makes those kind of jokes. She did truly catch me off-guard that night. Trying to keep up, I asked her if that meant he was a ‘no,’ to which she answered that she “just wasn’t a big fan of high-fives” as she drank in my again-shocked face.

Natalie and I regrouped with the rest of our friends, who looked as if they had grown seven years older since we last saw them. It was just bordering on the time of the night that you could call “late,” and Kathy, Shaun, and Rita seemed sufficiently drunk and tired. They said it was time to call it a night as though it was a unanimous vote.

A mix of feelings washed over me. Relief because I knew I wouldn’t be making any mistakes tonight, and disappointment because the very thought of Natalie was getting infinitely more sexy each minute I spent with her.

As the group got up to leave, Natalie blurted out that her and I were just talking about how the night was young and that we might stay out a little longer. Shaun and Rita looked to one another with a smile and gloated that both Natalie and I had “kicked and screamed” about coming out tonight, but knew we would have fun in the end.

Patting themselves on the back thinking they were good friends who had created a wholesome night rather than a monster, they left the bar with Kathy, instructing me to make sure Natalie got home safe.
Like runners at a starting line, we watched our friends pile into an Uber, their car leaving our sight like a starting pistol.

Immediately Natalie offered to buy a drink for “that guy I knew,” and we made our way to the bar, buying the night’s special which tasted like it was made of tequila and cough syrup. We found some stools in the corner of the bar and toasted to “meeting new people.” Natalie’s outfit fought with the height of the stools, forcing her to cross her legs and lean in close to hear me.

I couldn’t help but leer at the tantalizing amount of thigh I’d see above her boots before she’d again tug the skirt down to cover up, her hand strategically reaching out to my upper leg for balance.
Acknowledging my gaze without outwardly discouraging it, she mentioned that this was Matt’s favorite skirt on her, probably wearing it that night out of spite. Guilt hit me like a bucket of ice water. I nearly felt sick to my stomach as I considered the possibility of leaving right then, meanwhile my eyes never considered moving from her hips.

Natalie half-apologized, playfully noting that a night out was no place for “work talk,” either in reference to the fact that Matt and I still worked together or her image of the former relationship. She took a sip of her drink, letting me suffer through the reference, before challenging me on what I had said earlier, demanding I tell her more about the “guy who knew how to keep his mouth shut.”

Specifically, she asked if “he” could help her with “the one cure to post-breakup feelings,” reciting each clumsy suggestion and corny innuendo I made through the night, and holding me accountable for every one like a sexy Sherlock Holmes delivering a devastating report. She was meeting me nearly drink-for-drink through the night, and I certainly wouldn’t have had the kind of clarity, memory, or focus to do what she did. She was driven.

All the same, I met each of her questions with a ringing endorsement for “the guy I knew.”

I began to ask Natalie why “he” would want to meet her as she reached for her drink, but was interrupted by her losing her balance on her stool, again balancing herself by reaching for my leg, this time reaching dangerously far up my thigh. She slid herself onto her feet, pushing off my leg and taking the opportunity to position her hand nearly at my crotch and pose it as an accident.

Recovering quickly, Natalie lamented her ability to ride the stool as she exaggeratedly adjusted her skirt and boots in front of me. Natalie promptly handed me her half-completed drink, telling me to finish it for her. Downing the misguided attempt at mixology, she remarked that this venue really wasn’t the right place for this conversation. With a grimace born of the final sip I asked what she had in mind: she simply replied that I promised my friends to make sure she made it home before handing me my own partially-finished beverage.

Answering her challenge, I emptied the glass, gesturing to the exit and following her lead.

Before we had even reached the door, Natalie had an Uber ordered. She stood tall and confident on the sidewalk, scanning the horizon impatiently, paying no mind to if I had even exited behind her. In what felt like no time, the car came and we both climbed in.

I held the door for her. Natalie took the middle seat in a wholly unoccupied backseat row, forcing me to sit closer to her side. I remember neither of us wore seatbelts, I thought nothing of it as it was far from the largest risk I was taking that night.

Outside of asking for her name, the driver said nothing. Meanwhile Natalie spoke to me in a softened voice, too confident to be construed as a whisper. Her words felt dewey as she told me how grateful she was that I introduced her to “the guy I knew.” Her hand again on my leg she teased that she was not very good at keeping her mouth shut, asking me if that would be a problem with what I can only imagine were doe eyes in the darkness.

I teased back as well as I could, like a drunkard swinging at a prizefighter, telling her she couldn’t change the deal now unless she was prepared to deal with the repercussions. She had none of it, her hand briskly making its way up my leg telling me that the time for negotiations was over, and I still had an obligation as her hand finally found my cock, dancing lightly on it through my pants. I tensed up, her hand casually wandering back down my leg as the driver’s eyes looked fleetingly to the rearview mirror.

The car pulled up in front of her apartment and my heart sank again. This was the apartment Natalie and Matt were living in together until a couple weeks ago. I had been before. Pretty recently at work, Matt had told me he moved out. He said he was keeping his distance but still had a key. He was torn-up. His name was still on the lease.

I listened to Natalie thank the driver in a honey-sweet voice that betrayed her dark intentions. Frozen by recent conversations with Matt, I watched the car drive away out of distance, the last bastion of my conscience demanding I do something. But I couldn’t. Negotiations were over.

I had an obligation.

I followed Natalie to her apartment, a precarious staircase between us and her front door. The door swung open, the thud of Natalie’s boots on the hardwood floor a stark reminder of previous visits. The tension of the moment, the act, and the night pounded against my chest. I followed her in, desperately attempting to figure out what I’d say when the lights were on and the door was closed behind us.

**The lights didn’t come on.**

As soon as I crossed the threshold, Natalie threw herself at me. I scrambled to delicately close the door behind me as her lips swarmed mine, but her body had other thoughts, slamming into me, my body like a battering ram, the impact closing the door with a resounding boom. Pinning me to the back of the door, Natalie was unrelenting, her lips on a vicious conquest of my face, her hands violently acquainted with my groin.

I kiss her back. Sloppy, heavy kisses, wholly loveless, wholly lust. My hands still fresh from a long, loving relationship, navigated her body as if it were a lit piece of dynamite. Noisey kisses echoed in a hollow home. Both hands find her firm ass, the texture of her skirt feeling alien to anything my ex would have ever worn. My hands are magnetized to the newness of it and what it represented. Her hands meanwhile tug desperately at my belt, furious at its mere existence.
Natalie’s tongue clashes with mine, I grab her ass, her hands defeat my belt. She begins tearing down anything separating her from my cock. I remained entranced by her curves, my grip resigned to never leave them. Within seconds, we’re separated. Her ass slipping through my hands as she falls to her knees.

Prepared to officially cross the point of no return, I feel her come in contact with my dick for the first time. Her tongue her chosen tool of destruction, her soft mouth enclosed on the head of my dick before I can even comprehend what’s happening. My back still braced against the door to her apartment, I feel it rattle slightly in the loose frame as I instinctively buck back with each stroke of her tongue on my shaft. Hands falling limply to my side, Natalie’s lips cling airtight to my cock, a loud pop reverberating around the room as she completes a mercilessly slow journey from the middle of my shaft to the tip of my head.

I pound my fist against the door as her tongue hurries back to the tip of my cock, her mouth on a warpath of pleasure that I could only hope to endure. I curse loudly and pound on her door in pleasure again. There was no elegance to Natalie’s technique, simply raw passion and energy as she strived to suck the life out of me.
Eyes now somewhat adjusted to the lowlight, I look down to her. A combination of the muddled street lights peering in through unadorned windows and the dull glow of nearby appliance displays serve as our mood lighting. A door mat lays askew, partially under my foot and her knee. Her bangs fall across her face as she finds new angles with which to eagerly study my cock with her mouth.

Perhaps feeling my eyes boring into her very essence, she looks up to me. As we make eye contact, she withdraws my dick from her mouth, electing her hand to slowly jerk me in the interim before she caught her breath. I spy her glistening lips curve up into another sinister smile, a near-silent giggle heard as she cooed my name up to me. My name felt like a weapon from her lips as she teased me, her palm rhythmically slithering up and down my length as she chastised me for the terrible mistake I was actively making in a mocking tone.

I curse aloud genuinely, the complexity of the roller-coaster ride she had taken me on hitting me in that moment. She relishes her position with a laugh that could only be described as a cackle, knowing damn well that no matter how badly I was fucking up, there was no way I would stop now. Her words dripping with venom, she spares none of them, reminding me in no uncertain terms that I was putting my dick in “my friend’s girl’s mouth,” as I again feel her lips slide around me.

Even if they were broken-up, it felt filthy, just as she intended.

Natalie sucked me greedily, pulling me in and out of her mouth at a cruel pace. Possessed by forces beyond my comprehension this pace only accelerated, her hand gripped around the base of my shaft, urgently forcing her lips closer and closer to her knuckles. I curse repeatedly, my mind rapidly clearing of all other words I know as primal noises of exertion and pleasure rise from below me.

All-consumed by her, I feel the need to explode approaching at a breakneck speed. The physical euphoria battled how mentally turned-on I was, the latter refusing to let this reach its climax here. I groan out to Natalie, begging her to slow down, an indecipherable hum her only response as she maintains her feat of pleasure.

Her tongue taking control of my whole body, I desperately reach out and physically pull her off my dick. Natalie resists, equally desperate to return her lips around my cock. She succeeds, pushing hard into me, pinning my wrist against the door behind me as she bobs her head at my waist passionately, driven to break me down to nothing with her mouth. My eyes nearly roll to the back of my head, swaying on the line between refusing defeat and unloading into her mouth.

Again, I drive her off my cock.

Again, she dives back to it.

Her strength betrayed her looks as I found myself using considerable force on my third attempt, knocking her hard to the ground. I follow her down, hoping to catch her or buffer her collision with the hard wood floor. As I come down on top of her, I feel her hands reach behind my neck and pull me in for a deep kiss. I balance myself on my forearm, the grit of dirt knocked free from the door mat sitting uncomfortably between my arm and the floor. Brutish kisses are exchanged as I wrap myself around Natalie, rolling her onto her side, forcing her hips close to my exposed front.
I waste no time exploring Natalie’s body as our lips remained busy. My hands demand entry into the rear of her skirt as its tightness fights me. I slip my fingers below her waist just below the small of her back, untucking her sheer top as though it were tissue paper in a gift bag. She takes this as a cue to follow suit, busying her hands with any buttons on my shirt left secured before pushing it off of me and running her hands along my bare torso.

I can wedge my hand as far down Natalie’s skirt as the base of my wrist before it’s too tight to penetrate, my fingers reaching in vain for a handful of her ass. Frustrated, I unsheathe myself from her skirt, further dislodging her top in the process, prompting her to pull back and yank the sheer blouse over her head. She casts it into the unexplored abyss of her apartment, the once sexy piece of her outfit having served its purpose in her greater scheme.

Roughly, I pull Natalie back close to me and our lips again become intertwined in indulgent, wet kisses. Both of us now half-naked, I feel her skin slide against my own, blocked only by the black bra I had been eying all night. Mercifully, my hands make light work of it, the bra’s clasps a simpler foe than her skirt. Immediately, she pulls my hand to her exposed breasts which I thoroughly explore.

Past impressions from outfits I’d seen her in undersell the majesty of her chest. I grab at her insatiably, each breast a perfect handful. Our lips continue to dance effortlessly, as our attention lingers down below. My thumb traces the base of her nipple, intrigued moans vibrating through her kisses, increasing as my touch spirals inward. Nearly snorting in anticipation, I spare Natalie, my thumb flicking across her nipple. She groans and bites my lower lip as I deliver what she wants.

Spurned by the sensation, Natalie’s tongue nearly descends my throat in deep, relentless kisses. I feel her hips grinding against my own, the skirt’s large metal zipper playing a dangerous game with my cock. Her moans increase the more my thumb dances along her chest, the noise like rolling thunder contained only by my lips’ refusal to leave hers. Unable to contain herself, she pushes herself hard against me, jamming her tits against my chest before grabbing me by the back of my head and jamming my face into her cleavage.

I speckle her skin with slow kisses, drawing out my arrival at her sensitive nipples as long as I can personally muster. It’s not long before I give in, a cacophony of licking, sucking, and kissing as I take her curves in my mouth. Cute whimpers give way to delicate moans as accompaniment to my performance. It’s not long before these are joined by Natalie’s fingers pouring through my hair which in time develop to specific requests. My tongue flicking tirelessly on her nipple, these requests sour into demands which I follow, biting her gently as she pulls on my hair and holds her breath. As Natalie exhales she quietly asks herself when I’m “going to fuck her already.”

Reluctant to separate my face from her tits, I continue to tease her, which she greets with greater provocation. Natalie coos my name, begging me to “take her already” and “just put it in.” My fingers lay the groundwork to make her own up to these demands, taking a new approach to her skirt by pushing it up from the bottom. With little protest from the skirt, it gives way to her most decadent curves yet, half exposed to my gaze and touch. I raise my face from her breasts and can’t resist giving her newly revealed ass a slap before laying a trail of kisses up her neck.

I play with Natalie, questioning if she really wants me to fuck her. She confirms breathily, detailing how badly she wants it to happen. I plant two slow, strategic kisses on her neck as my eager hands yank her underwear down past her hips, returning my mouth to her ear and confirming that she wants me to fuck her right here on the floor of her apartment, eager to hear her repeat my words in approval.

And that’s exactly what I hear.

I struggle pulling her underwear past her tall boots. I grope in the dark for zippers or some way to get them off her, while she writhes in anticipation for my next move. Clumsy, I can’t piece together how these boots came on and off; meanwhile Natalie curses my name, returning to a pleading chorus of demands for me to “just put it in.” The sensation of trying to slide her boot off fills me with dread realizing I don’t have a condom. I whisper to Natalie if she “has something,” trying to avoid clinical language souring our lewd dialogue.

Seemingly puzzled, Natalie is quiet for what feels like an eternity as I fight for each inch her underwear gets down her boot. She pushes me off her and stands up, wriggling her underwear over her boots with a technique clearly born of practice. I stand up next to her, shedding any remaining clothing I had left. As Natalie reaches for the top of her boot to work whatever magic gets it off, she suddenly stops, my words click on a long delay.

She looks up to me and grabs my hand, leading me several steps in the darkness to her living room declaring that she was on the pill, this home clearly not having had this conversation in years. Callous to such a notion I inquire again if she has anything I can use. Instead of answering Natalie throws herself into the corner of an L-shaped couch, pulling me on top of her and demanding angrily and finally that I “just fucking put it in.”

My naked body poised over Natalie, I remember the scarce few movie nights I had spent on this couch with the happy couple. The damage I’ve risked to my friendships by letting this go this far felt infinitely more dangerous than unprotected sex with a woman fresh out of a longterm relationship. My rigid cock pointed at her like a rifle, my hands violently push up her skirt, unthinking to simply force down its zipper.

Natalie giggles excitedly at my newfound aggression and willingness to follow directions as she squirms to wriggle the skirt up above her hips which she elevates for my ease of use. My cock descends between her legs, my hands bracing on either side of her as the tip of my dick introduces itself to her lips. Natalie wraps her arms around me, her wrists resting on the back of my neck as if we were slow-dancing at prom. Her eyes look up at me with a devilish glint.

I slide slowly into her, her pussy greeting me tightly. My ex who I had broke it off with only a week or so prior had an intense fear of pregnancy and insisted I wear condoms even while she was on the pill. Perhaps the rediscovery of the sensation of going in raw heightened the feeling to unknown levels, but the first few seconds of entering Natalie were mind-shattering. I groaned loudly halfway into her, her sopping wetness encouraging me to push in all the way.

I thrust my entire length into Natalie and her eyes grow wide and vulnerable. She moans out my name, painting each syllable as a challenge to get out. I rear back to pump again into her, stifled moans of elation flowing from us both, discarded pieces of my name occasionally slipping out of her mouth. My mind is aflame with the reality I was in as I establish a pace and Natalie rolls her hips to follow along. What I was doing felt like a new level of immoral for me, the nastiness like an illegal stimulant to my arousal, yielding otherworldly ecstasy as I drilled harder and deeper into Natalie.
She calls my name with intention whenever I pull back, only to lose sight of whatever she was about to say as my cock fills her. For all her expert teasing, it was useless to her now. I followed her prior challenge to take her.

More lust than man, I fuck Natalie with an ever-building rhythm. Pounding into her, I feel her hand grab onto my arm and squeeze with all her might. Her bangs fall back from her face as she arches her back and leans her head far back on the unstable couch cushions. Marveling at my own handiwork, I’m unrelenting, only ramming harder into her as she silently clamors to catch her breath, my free hand toying with her nipple as her tits are thrust up toward me.

As if her spirit had left her body and only now just returned, a roaring moan comes from her mouth as her body collapses flat on its back. I push my cock deep into Natalie and hold as my name stretches from her mouth in a tone that is simultaneously impressed and alarmed. Weakly she pushes me back and I pull out of her completely. She rolls away from me, burying her face in the pillows at the back of the couch, I lower myself behind her, the furniture just wide enough to hold us both lying down.

I hear her curse into a pillow, her words muffled, her torso heaving as she catches her breath. I unintentionally wipe her wetness from my dick onto the rear of her legs, admiring her sexy back and shoulders. Still turned away from me, I look down at her body: a satisfyingly dirty feeling washes over me as I see her disheveled boots and skirt still clinging to her curves. I reach to undo her skirt from our spoon position, but such a courtesy is quickly corrupted by the temptation to tease her with my fingers while I explore the area.

Careful to let her regain her strength, I curiously slip my middle finger into her pussy, again shocked by how wet she was. Reluctantly delighted whimpers follow as my fingers take their time to pamper her. Unwilling to rest for long, Natalie reaches behind her, securing my cock tightly in her hand. I shift myself down the couch as I feel her guide me into her again, I gladly sink my dick into her from behind, both of us still on our sides.

Taking it significantly slower, my dick slides in and out of Natalie, our heads close enough to appreciate each unexpected sound of pleasure that sneaks out of us. I take a page from her book, groaning her name back to her with each thrust. She hums back approvingly, turning her head to deliver long, warm kisses to my cheek. The kind you would call “romantic” were it under any other circumstance.

I keep my precise, drawn-out pace; our bodies appreciating each other and flowing in sync. Retracting from a lingering kiss on my cheek, she pulls both of my arms around her, paying special attention to lay my hands on top of both of her breasts. Struggling to multi-task, I pull my cock too far back and slip out of her pussy, Natalie eagerly returns me into her before asking me if this was worth it. I look down to her face, and realize the sinister glint has returned to her eyes.

She asks again if this was all worth it. My purposeful pace begins to pick up steam, I hear her adapt with a stifled moan. I tease her, telling her I wasn’t sure yet, unwilling to confront any sort of real answer to that question. She pushes her ass hard against my front, playing coy, asking what more a girl could do. I push back hard into her with my cock, a slight yelp shoots from her lips.

Natalie muffles the noise by forcing her lips to my cheek, delivering another indulgent kiss. As her lips come away from my skin she remarks that I’ve been worth all the effort it took to convince me. My ego inflated, I pick up my pace pumping my cock into her. She jokes that I couldn’t take a hint and that we should’ve head out after “the place where I had my cigar.” I feel myself reaching my limits as she reminds me of the situation. Trying to keep myself from the point of no return, I pull out abruptly, and sit up on the edge of the couch.

Natalie follows me up, finally taking the opportunity to push off her tall boots. She giggles as she gets the second one off, its heel landing loudly on the floor, she asks me if this has been “raunchy enough” for me. I laugh, still ashamed at my obtuse phrasing from earlier in the night. Seeing it as an opportunity, I lean back on the couch and tell her there’s still room for improvement. Natalie looks to me with an unplaceable wildness in her eyes. She straddles me with her now bare and perfectly shaped legs.

She pulls my hands up to the zipper on her skirt, I place two fingers through the circle of it and pull at long last. It resists me, but I get the zipper down its track as Natalie unhooks whatever else was keeping it on. It falls to our feet, Natalie now entirely naked, each enticing curve of her body etched permanently into my memory. Gently, she places both of my hands to my side before coming in close to my face.

Wickedly, Natalie asks, “How does it feel to be the second guy to fuck me in that skirt?”

All hell breaks lose, I force her down hard on my cock, but she was already halfway there. Our lips at war with one another, she bounces and slides on my dick, her hips grinding against mine as I buck upward with every remaining ounce of my strength. Moans boil up her body, breaking our kiss to unleash them with thunderous volume. I don’t doubt that everyone in the building can hear her as the moans evolve into my name, Our eyes locked, my hands grabbing her ass tight for maximum force as she cries out for me to fuck her.

Placing her hands on my shoulders, she shoves her chest in my face, my mouth and tongue again in service to her tits. Neither of us are able to keep this pace for long, so I aim for a strong finish. I hoist myself up, hoping to take Natalie with me, but instead send us falling off the couch. We both land hard. I get to my knees above her and she spreads her legs. Planting my hands on either side of her head, I begin fucking Natalie missionary, I remark aloud how “fucking dirty” it all was, to which she had some smart teasing remark.

I gave her everything I had left, driving deep into her. She seemed to be at her end herself, only with the energy to groan my name loudly in case her neighbors missed it the 25 other times. Finally, I feel myself ready to erupt. Believing it to be the proper punctuation to a filthy night, I pull out and finish on Natalie’s chest. She groans out a final “fuck” and I collapse on the ground next to her.

We lie there catching our breath for a long while. It could’ve been hours or minutes, my very being was bent out of shape. Eventually I hear what I think was a “thank you.” I look over to Natalie, she’s where I left her, eyes closed.

In the dark I question every decision I had made with my life.

Realizing with horror somewhere in there that Matt theoretically could walk in right this second with his key, I scramble to get myself together. I grab my clothes which lie in a heap by a pile of boots and heels at the front door. I return to Natalie and offer my undershirt to clean herself up with. She waves it away. “Just leave,” she says with closed eyes.

I stumble with my words, seeking clarification. “Just leave,” she says again, her tone finally reminiscent of the woman I had known before the night. I remember our deal, I remember my brainless lines about being a guy that can “keep his mouth shut,” and I remember the weighty conversation we had about relationships earlier that night. I respected her wishes, got dressed and left, locking the doorknob behind me.

I remember that night well for so many reasons. I replay it in my head for so many more. It was heavy for me at that time. I hadn’t had a sexual encounter with that kind of intensity, risk, and reality before and it kind of messed me up for a while. It truly felt like a dirty dream, but one where you had to panic about the possible repercussions after.

I definitely felt used, for better or for worse.

Anyway, I heard a few weeks ago that Natalie is in a pretty serious relationship now. It’s her first one since this particular breakup, so it all kind of came to mind again. In some ways, I was happy to be her interlude, but am happier she’s back in something stable now. Writing it up here felt like a good way to close that particular book. If you read through the whole way, I appreciate it, it feels good to finally share the experience after all this time.

Source: reddit.com/r/gonewildstories/comments/b6vbm0/mf_trying_to_rebound_with_the_worst_possible