This story was originally posted by MindSketchWriter and recorded with their private permission. Check out the Cheeky Chapters Podcast for an immersive audio experience, with a new story every day.

“Nnng…”

Manicured, crimson-painted nails dug deep into the sheets of my bed as Jessica buried her face in my mattress to smother her scream as she came for the third time. She shoved her large, juicy ass into my crotch, meeting each aggressive thrust with equal fervor. Her long braid was wrapped around my hand like a rope and I was using it like a leash, applying steady force to it with each of her thrusts in an attempt to penetrate as deep as possible into my girlfriend of 7 months.

A smile creeped across my face as I enjoyed watching the juxtaposition of me forcing her down into the bed with one hand pressed firmly on her back while I pulled on her hair with the other. Jessica turned her face to the side and drank in oxygen between encouraging syllables, “Fuck… me… Marcus… fuck…

“Fuck yes! Cum for me! Cum on my cock, bitch!” I growled in response.

She turned her head and screamed into the mattress again, and I felt her body shudder under my palm as her juices coated my shaft - this was a particularly juicy one. I kept thrusting, feeling myself approach that critical moment. My eyes roamed over one of Jessica’s best features - her flawless skin. As someone who spent most of her time indoors reading and maintaining a rigorous skin care routine, she was almost translucent with a flawless complexion that I constantly marveled at. Her back, her shoulders, her ass… it was all a flawless work of art like the finest marble.

I leaned forward as I still pounded her, loving the feel of her shivering under me as she continued to ride out the final tremors of her own orgasm. I reached under her and cupped a heavy breast, kneading it roughly as I got closer to exploding in her. I kissed her ear, “That’s it baby… feel that dick deep inside of you. I’m gonna cum. I’m gonna cum in you Jess. I’m gonna cum -”

I sank my teeth into her shoulder and gripped the breast in my hand firmly as I let out a loud groan. My cock began spasming, and we both felt white ropes of warm semen coat the walls of her pussy. I reached up with my other hand and wrapped it around her throat. Now that both hands were occupied, my weight drove her completely flat on the mattress as I still continued to ram my hips into the cheeks of her generous ass, luxuriating in the way her pussy seemed to become almost soupy with the combination of our juices. I tightened my grip on her throat and bit harder into her shoulder, intending to leave teeth marks that would take days to disappear. Jessica loved it.

“That’s it, baby. Make me your fucking whore. Make me your fucking sex toy! Goddammit! Fuck!” she said through gritted teeth.

My orgasm began to slow down, and so did my thrusts. Jessica pressed her juicy ass into my crotch, helping me grind my cock into her as the last of my cum leaked out of the head of my cock. I could feel the mixture of our juices seep out from where our sexual organs joined. Our entire groins were soaked, and I could only imagine what the bedsheet underneath us looked like. I released my hand from around her throat and cupped the side of her face with it. My bites turned into kisses as I began trailing them softly across the fair skin down her shoulder blade toward her spine. We synced the gyration of our hips, and she moved her face to capture my thumb between her soft, crimson lips. The feel of her tongue lolling around my finger caused my dick to lurch, a bit more cum seeping out of its tip.

I began trailing kisses down her back, marveling at the flawless canvas that I’d painted repeatedly with my tongue and lips, tasting the saltiness of our combined sweat. I enjoyed exploring her body as I felt her moan and whimper around my thumb in the throes of post-orgasmic bliss. Finally, succumbing to the real fact that I would have to bring this session to an end, I crawled up her back and laid several more kisses along the nape of her neck before rolling to the side on my back. The air was filled with the smell of sex and the sounds of labored breathing as we recovered our breath.

I looked at her. She peered at me with one eye, half her face buried in the mattress, and gave me a small smile. I rolled to my side, placed a hand on her back and began letting my fingers trail over her skin as I leaned forward and pressed my lips to hers in a sweet kiss. Her lips remained unresponsive for a few moments before moving, her efforts meeting mine. I felt them give way and allow my tongue entrance to find her’s, forcing them to dance with each other in a way we’d perfected over the last week where we’d been inseparable.

After two full minutes of making out, she broke her kiss and rolled away from me so she lay on her back. She placed one hand behind her head and stared at the ceiling. My eyes wandered over her body - Jessica wasn’t about to win a contract as a fashion model - at 5’9, she was a big girl with fairly broad shoulders and hips, a juicy ass, and large tits that probably filled a double D cup bra. She was at a comfortable weight with just a bit extra to make her ass and tits even more formidable. As she laid on her back, I enjoyed the opportunity to paw at one, gently rolling the warm flesh in my palm in a way I thought was more soothing than arousing.

Jessica was solidly built, but that meant she could take a lot of punishment when things got rough in the bedroom, which both of us enjoyed. She was kinky, perverted, and there really wasn’t much that shocked her. In the seven months we’d been together, she’d taken a butt plug up her ass. We’d enjoyed tying each other down and dripping all sorts of things on each others’ bodies from hot wax to honey. She’d kept count as I spanked her. She’d submitted to me while I strapped a collar around her perfect throat. She’d blushed prettily when I called her a good girl and had licked my fingers clean when I’d cum in my hand. She was creative, imaginative, and exciting, and also just a lot of fun.

Physically, two of her best features were her face and her complexion. With naturally crimson lips, sparkling hazel eyes, and incredibly cute dimples she looked like a princess in a cartoon, albeit one with a bit of a different build. Still… she was beautiful, bubbly, and generally a lot of fun.

I glanced at my alarm clock, “An hour and a half.” I looked back at her, palming a large breast in my hand, “Not bad, if I say so myself.”

She only sighed and continued to stare at the ceiling. Then she muttered something under her breath.

“What was that?” I asked.

She hesitated, then looked at me, and I could see tears beginning to form at the corners of her eyes., “I said I’m going to miss this.”

“Aw. Me too, baby.”

Jess lived in Kansas. I lived in New York. We’d met online, hit it off really well, and ended up taking regular trips to fuck each other for the past year and a half before I’d made the move to finally make it official about seven months ago. Now we were entertaining the idea of her moving to New York so we could be closer… a serious step toward something more permanent between us.

She was leaving to head back home after a week of apartment hunting and fucking. We’d only seen a few places the second day she was in town, but she said that was enough… that she’d be able to make a decision based on what she saw. I didn’t complain, as it meant more time with my dick in her.

“But the distance won’t be an issue much longer,” I said as I leaned down to give her a kiss on her pale, pink nipple. It immediately hardened under my lips.

“No,” Jessica said as she placed a hand on my cheek and pulled me off her breast so that I was looking directly in her eyes. “That’s not what I mean.”

“What do you mean then?”

I wasn’t sure what she was getting at.

“I don’t think I’m going to move,” she replied.

“You’re not? Why?”

She shook her head, “No. I’m staying in Kansas.”

“Why?” I repeated.

She looked away from me, “I met someone.”

A chill ran through me. She’d met someone?

“Why?” I repeated the question again, but the meaning was very different this time.

“I’m sorry Marcus,” she said. She was no longer looking at me, but I could hear how upset she was. I felt my jaw ache and I locked it in place. She still hadn’t answered a single question.

“Seriously. Why?” I asked again, “I’ve been a great boyfriend. I’ve been incredibly patient. I’ve paid for you to come out here and half our visits have been me coming to see you. I’ve met your family for Christ’s sake.”

She didn’t immediately look at me or acknowledge my words.

“Please tell me you’re joking!”

“I’m sorry.” She looked back at me, clear tears streaming down her face, and I knew this wasn’t a fucking joke. “It’s just-”

“How long?” I asked. Anger was starting to overtake my shock. When we’d first started this thing, it had just been mutual lust and fun. Over time, it’d grown into legitimate affection, care, and love. At least, it was for me. I thought it was for her as well. No… fuck her tears. I’d been good to her.

“Marcus-”

“No. How long.”

She stared at me for a long few moments before responding, “A month.”

I launched myself off the bed and walked away from her. A whole fucking month? I’d been dating this woman for a month. I’d ignored other opportunities… remained faithful, and she was doing this behind my back for a month? I grabbed my pants and began pulling them on, trying to feel nothing again. It was either that or anger.

“Marcus. Look I-”

“I can’t be here right now,” I said, grabbing my shirt. “I thought we were good. Hell, better than good!”

“We were. This just… happened. You’re all the way over here and… it just happened. I didn’t-”

“No! You were moving!” Pointed at her, my shirt in hand. “You were moving, and I was going to ask you to marry me when you got here! Jesus Jess! What the fuck?”

It grew quiet and I used the opportunity to put my shirt on, stewing on what she’d just told me. She’d been seeing someone else for a fucking month, and I didn’t even have to ask how far they’d gone. Of course they’d had sex. Jessica was a very sexual person. Our distance had been the biggest issue between us, and it had been a little over a month since we’d last seen each other. Once she’d found someone closer who could satisfy her a bit more regularly, it probably didn’t take long for them to climb into bed together. The fact that it had probably happened only a week after the last time we’d seen each other only made the sting more intense.

“You were going to ask me?”

“To marry me, yeah,” I said. I started donning my socks and shoes.

“I didn’t know…”

“That doesn’t matter,” I snarled as I grabbed my wallet and keys. “Maybe I might have been able to forgive a one-time thing, but a fucking month? Jess, I’d probably just left your house! What? Did you bounce right off my dick and onto his?”

“Where are you going?” Jessica had climbed to her knees on the bed just watching me, tear stains on her face. She was still naked. Her messy red hair was cascading down her chest over one shoulder, partially covering a heavy breast. She looked alarmed at the fact that I’d thrown on my clothes so quickly. For some reason, her confusion was stoking my anger toward her. How the hell could she be confused at any part of my reaction? And why did she have to look so beautiful, kneeling in my bed nude and vulnerable!

“I can’t be here. Pack your shit and leave,” I said. We’d had lunch plans, then I was going to take her to the airport. Like hell I was going to do either one of those things for her now.

“…How am I supposed to get there?” She asked, a timid note in her voice.

“I don’t know, Jess! Call a rideshare,” I fired back as I walked toward the door. “There’s sixty-something dollars in the side drawer. Take it. I don’t give a fuck!”

Jessica was broke. She was currently working as an administrative assistant at a box company in Kansas, but it didn’t pay all that well. On top of that, she wasn’t exactly the wisest person with her money. She didn’t live paycheck-to-paycheck, but she wasn’t terribly far from it. I on the other hand was an analyst in New York that made a high 5 digits. I wasn’t about to buy a house anytime soon, but I did well enough for myself. Jess had relied on me for most of the financial burden of long distance dating.

“Marcus!” She called after me. “Can we talk about this a bit more!?”

I stopped at the door and turned to look at her, “Have you been dating someone for the past month while we’ve been in a relationship?”

“We’re not technically dating.”

That was enough of a yes for me. “Have you slept together?”

She didn’t answer immediately. Also a yes.

“When you said you were going to miss this, did you mean for the next month while you were back in Kansas packing to move here, or did you mean because this was the last time?”

She hesitated, “I…”

“That’s enough for me. Have a nice life, Jessica. Lock the door on your way out.”

I turned, caught sight of Jack, my cat, sitting on the counter. He slow-blinked up at me and then looked back toward Jessica. Jack preferred to keep out of the affairs of humans, as he thought our goings-on were beneath him. He was probably right.

“Jack, don’t let her steal any of the expensive shit in this house,” I said, opened the front door and walked out.

“Marcus!” Jessica called out behind me. I just slammed the door behind me. I didn’t feel like hearing anything else she had to say.

I started down the hallway toward the elevator when a head poked out of the apartment right across from mine, almost bumping into my chest. A gasp of surprise and Phoebe Lucas’ dark brown head disappeared behind the door again so she could avoid colliding with me. I swerved out of the way to avoid possibly crashing into her, and a moment later, she reemerged, her eyes wide as she looked from me to my front door.

“Everything okay?”

“Everything is fine, Mrs. Lucas,” I groused. “Jessica and I just broke up. She’s still in there but she’ll be gone soon.”

Phoebe Lucas was a woman in her early 40’s who worked as a bank loan officer in New York. I’d known her for three years, and we got along well. She was a lovely woman with a sweet disposition who just so happened to be married to a steel worker who made beating his wife a pastime when he wasn’t beating metal. At least, that’s what I suspected. Jim and Phoebe had a cute little 2 year old kid, and I suspected that he liked his dad as much as I did.

“Oh!” Mrs. Lucas said, “I’m… sorry?”

“Yeah,” I said. “Me too.”

“Are you okay? Do you need to talk?”

I shook my head, “I do, but I’m going to grab some coffee with a friend.” I tried giving her a smile, but it felt half-hearted. “Want me to bring you back anything when I get back in later?”

She smiled back at me, hers much more genuine-looking than mine felt. She really had a lovely smile and a sweet disposition. There were a few premature lines on her face, likely due to her moron of a husband. “No thank you. Jim will probably be home then. He…” She didn’t finish the sentence, but she didn’t need to.

“I get it,” I said. “Do you need anything?”

She shook her head, “No thank you. I’m good.”

I stared directly into her dark brown eyes for a long moment, assessing the situation. It was crazy how quickly you could forget about your troubles when you were concerned about someone else, even if it was your girlfriend cheating on you.

“Okay,” I finally said, “But you know I’m here if you need anything.”

“Of course,” she said. “The same goes for you. I mean… when Jim isn’t here. You know.”

“I know. Thanks, Mrs. Lucas.”

“I keep telling you,” she said. “Phoebe is fine.”

I nodded and gave her a weak smile, “I’ll try.”

I turned and made my way toward the elevator, then hesitated and turned around, “Oh, would you do me a favor and make sure my door is locked after the lying bitch is gone?”

“Order for Marcus!”

I retrieved my coffee from the counter and made my way to my usual spot in the back of the common room of Strange Mudd - a local coffee shop in New York. Normally, I visited here early in the morning before work when the customers were a bit more sparse. I rarely visited this late in the morning, and I was fortunate enough to find a seat - a small miracle. The din of a busy coffee shop slipped into white noise as I sat drinking my coffee, staring into space, and letting my breakup sink in.

My story was like the stories of so many others in New York City. I grew up as part of middle class America in upstate New York. I was one of four children to an architect mother and a musician father. Well… step-father. My actual dad skipped out on my mother the moment the stick turned blue. Or pink. Whichever one meant that my mom was pregnant with me.

It was a good childhood. My mom loved me and after I was born, she went back to finish school, leaning on her parents to help raise me while she was busy. Within a year of completing her degree and getting a job, she married Henry, and our family went from two to six due to Henry having a daughter a year younger than me. A childhood, two more half-siblings, and a degree later, I found myself in New York working as a financial analyst for a firm thanks to an education in finance.

I developed a pretty good life here. One cat named Jack, a single-room studio apartment, a handful of relationships, and a small group of friends, including-

“Sup nerd?”

Dillon dropped in the chair at my small table opposite from me, grinning ear-to-ear as he wiped his hands on his apron. Dillon was an aspiring actor who had tried his luck out in LA and through a string of events, had ended up in New York doing mostly stage. He liked it well enough, but New York wasn’t cheap, and he needed the coffee shop to supplement his income until he finally made it big.

“What’re you doing here? I thought you would have been chest deep in Jessica right about now.” He glanced at his phone then looked around, “isn’t she supposed to go to the airport in a couple hours? She here?”

I took a sip of my coffee and just stared at it as I placed it on the table.

“Yo. Everything alright?” He asked, his tone taking a bit more of an edge. Dillon was the least serious of my friends, but he was also the most empathic of the group.

I just shook my head and glanced up at him, trying hard to hide the fact that I was really confused.

“What happened?” He asked, looking genuinely concerned.

I shrugged one shoulder and finally piped up, “We broke up. She’s not moving here. There’s someone else, so she’s staying there.”

Silence reigned between us for a few moments and I resigned myself to studying my coffee cup again.

“Man… that sucks. When did she tell you?”

“About thirty or forty minutes ago,” I said, not looking up at him.

“Bitch…”

“Yeah…”

“Where is she now?”

“My apartment, getting her crap together. I told her to leave and lock the door on the way out. She’ll probably be gone in another hour or two.”

“You want me to call my uncle? I could have her arrested for being in your apartment. We could say she broke in or something.”

I chuckled at that. Dillon’s uncle was NYPD. It was tempting to do something like that to her after she gut-punched me like that, but it wasn’t worth it. Anyway, I figured Dillon was primarily kidding. There was no way someone on the force would risk his job over a favor for a guy with relationship problems. He’d probably tell me to get over it and remind me that I’m a fish in one of the biggest ponds in the States.

I shook my head, “Nah dude. You’re a real one for offering, but I think I’ll just let it be.”

“You did say she could be a little much at times,” Dillon pointed out.

“Yeah. I did. But I think I was getting used to it.” I hesitated, looking around at all the random people who had their own stuff going on. “I told her I was going to ask her to marry me.”

“Seriously?”

“Yeah.”

“Were you?”

“Maybe,” I shrugged. “I’d thought about it quite a bit. I didn’t have a ring yet, but I imagined proposing to her when she finished moving here.”

“Damn dude.”

“Yeah. I know.”

“But you probably dodged a bullet.”

“Yeah. Maybe,” I replied and took another sip of coffee. “It was comfortable though. She was comfortable. What we had was just nice… I don’t know. It just sucks.”

“Yeah.”

Silence fell between us again, and I just let the ambient noise of the busy coffee shop fill my head with its insistent buzzing… it was a good way to dissociate.

“Look at the bright side. You’re single now. In one of the cities with the largest populations of hot single women in the US. It’s a good place to fly solo.”

Well, if it hadn’t been Dillon’s uncle telling me that, it was bound to be Dillon.

I snorted, “That’s true. I just hate the whole dating thing.”

“I don’t blame you. It sucks ninety-eight percent of the time, but that two percent of the time?” Dillon gave a chef’s kiss.

“You’ll have to show me the ropes. It’s been a while for me.”

“Yeah. We’ll have to go out soon. I have an audition tonight, or I’d say let’s do it.”

“Soon,” I said and took another sip of coffee.

“I know a few too. And there’s my sister. She likes you, and she’s not seeing anyone.”

“I dunno,” Dillon’s sister was 19 and wild - two things I definitely wasn’t. “She might be a bit young for me.”

Dillon shrugged, “I’d trust you with her… and there’s Natalie.”

I hesitated mid-sip at the mention of that name. Natalie.

“You’re both available now, right?” Dillon continued. He glanced down at his phone. “Break’s almost up, my guy. I gotta get back to work. You got this though, dude. Stars are aligning… this is gonna be your time. And if you need to talk, you have my number.” He clapped me on the shoulder and gave it a squeeze. “Talk soon.”

“Thanks man!” I called out, raising my cup to him in cheers as he retreated from my table. I finished off my coffee as I mulled over what he’d just said. Jessica ending things the way she did hurt, but Dillon had a good point. There were literally thousands of women in New York.

And chief among them was Natalie.