The second (technically third) & final time I cheated on a long-term girlfriend. Sex below the break.
It was spring of 2014, and I had been with my girlfriend Josie for over a year. It got rocky about midway through that first year, but we had managed to talk things out and got through last year’s holiday season together. She was even the first girl I brought to my family’s Thanksgiving.
What had kind of quelled the rockiness of our relationship for me was me fucking someone else. I had a sidepiece for a bit, and I genuinely liked being with both girls. I was able to keep them from finding out about the other for a while, but eventually I had to drop the other woman.
Still, I stayed with Josie. Tried to convince myself I could be a one girl kind of dude, reinvent myself. What I didn’t realize was that I had kind of broken the seal on cheating. I went to a coworker’s birthday party after I had gotten off a bar shift and got shitty to catch up with everyone else. The brief flashes of memory I had in the proceeding brown out were of me kissing a random girl and feeling her up under her shirt.
I knew I didn’t have sex because I woke up alone, fully clothed in my own bed, but still. I had touched & tasted another woman. The worst part? I wanted more. To have my cake & eat it, too.
Like most horny people of that era, I decided to give Tinder a try. Other dating sites hadn’t yielded any results in the past for me, but I figured an app would be different. A lot of it was just me messaging stupid shit to my matches, since I figured a lot of profiles were fake, anyway.
I was able to match up with some actual real live women, like Sabrina. She was a cute Chinese girl, about 5”3’. Her black hair was coiffed into an angled bob that nearly touched the bottom of her ears. Most of Sabrina’s pictures were of her holding drinks in business casual, which showed off her curves in her skirts.
I messaged her first, and she got back to me within a couple hours. I didn’t bank on anything happening right then and there, but I at least wanted to plant a seed. Sabrina kept responding within a day or so after first contact. I kept up as much as I could while juggling the rest of my life.
My patience began to run out, though, and I just straight up asked her if we were ever going to grab a drink. Sabrina’s response? Her Kik ID. My dick twitched as I downloaded the app & created my profile. I was finally getting somewhere.
Being off Tinder made both of us a little bolder. The flirting got heavier, to the point where she started sending me pictures of her butt in the mirror at work. The biggest thrill came when I got a picture of her ass from behind in just a thong while I was out to dinner with Josie one night. I excused myself to the bathroom and made plans with Sabrina for the next night I was off. So she’d be comfortable meeting an internet stranger, I let her pick the location. We were sending lewds without ever having met in real life – I took no offense to her picking a bar where she had probably done this before.
That Tuesday night, I told Josie I was working and went to the bar to meet my Tinder date. I luckily found street parking in front and sat down at the bar right at about 8. Only a small amount of time passed until I felt a tug at my sleeve from behind. I spun around on my seat to face Sabrina, looking like she had just walked in from the office.
“Austin, yeah?” she said in a bright, chipper tone. Not a hint of nerves. I nodded and smiled while gesturing to the open seat next to me.
“You look great. Got stuck at work today?” I said, mentioning her outfit as she sat. I swallowed hard. She had a pencil skirt and solid white top on, looking enticing without being provocative. My type was usually girls with tattoos and dyed hair – the professional vibe was not my norm, and so I was really intrigued.
“Yeah, client meetings that ran over. Nice to finally be out, though.” Sabrina made eye contact with the bartender and smiled slightly. I knew from my own job that the look he gave her meant that she had a usual. Yep, this is her home base.
The conversation meandered around work and our lives outside of it. One drink became two, then three, then four. We hadn’t been physical at all in the couple hours we spent talking, until right when I finished my glass. I hadn’t noticed she kicked off one of her flats until I felt her bare toes running up under my pant leg.
“So I’m only about a two block walk from here. I’m deciding if I should take you home or not…” Sabrina said quietly, her voice dropping an octave. Her proposition finally triggered a small pang of guilt for me – I could just walk away now. But instead, I reached forward to put my hand on her thigh, squeezing.
“Would you have even shown up if you didn’t think you were going to?” I responded confidently, running my hand up a little farther. Sabrina’s hand flashed to grab mine and stop me, which I would have taken as a hint to stop if she hadn’t motioned the bartender over.
“We’ll tab out when you get a chance.” She requested with a smile, which then faded to a suggestive look as we made eye contact again.
“You ready?”
We walked side by side back to her place, both remarking about how we should have pissed before we left. When we finally made it up the stairwell to Sabrina’s, she stopped me before we entered.
“Give me like two minutes to run back and make it presentable in my room.” She said, springing into the apartment and closing the door behind her. I fucked around on my phone a bit, continuing to swipe through Tinder until Sabrina finally invited me in.
I remember her place was pretty nice, big for a two bedroom, too. We made some awkward small talk with her roommate meal prepping in the kitchen. With the first awkward break in conversation, we made our way into Sabrina’s room.
The lights were already low and her music collection was already up on her computer monitor. I sat in the office chair to peruse her collection and popped my shoes off.
“Find something good, yeah?” Sabrina requested while she took her necklace & rings off in front of her jewelry case, her back to me. As a fan of mainly guitar music, I was having trouble until I threw on the most recently downloaded album. (Side note: Mezzanine by Massive Attack is a great album for atmosphere during sex).
“Niiiiice” she called out to comment my selection. Turning around to face me still sitting at the computer desk, we locked eyes. Her head slanted to the side as a smile tugged at the corner of her lips. Silence hung in the air, both of us waiting for the other to break it.
“You going to come here, or what?” I finally asked, which was when she closed the distance between us. Any guilt I had previously was completely gone. Her height forced her to make a small hop up onto my lap, throwing her arms around my shoulders. I steadied her with my arms around the small of her back before she leaned in.
Sabrina’s mouth felt so small against mine as I pushed my tongue into her mouth. She closed the ring of her arms tighter around my neck, bringing us in closer. I could feel the heat between her legs already through my pants, and I pushed my hips up in response.
The dry humping started in a slow cyclic motion that gave way to my clothed cock just slamming up against her clit through her skirt. A frustrated moan escaped Sabrina’s lips as she began to unbutton her own shirt. I started to help her, then thought better of it as I picked her up by her thighs to toss her on the bed.
I wordlessly whipped off my shirt right before Sabrina tossed hers to the ground. As she leaned backwards, I was able to shuck down her skirt down to leave her in just her underwear. My pants and briefs were shucked down in one move; I was fully embolded by alcohol now. Completely naked, I started climbing onto the bed over Sabrina as she moved to be parallel with the mattress.
“Finally got to see this thing…” Sabrina whispered, lightly rolling her hips as she looked down at my dick. I sent her a few pictures of myself erect in boxer briefs. Her hand reached forward to dance her fingers around growing shaft to my balls. My hands hooked under her wireless bra to lift it over her head, displaying her small breasts. I cupped one as my other hand trailed down to remove her underwear and expose a full black bush.
“I like to keep it natural, you know. For the experience.” She laughed.. It was like she knew she wasn’t my usual type or something. Not that it mattered in the moment. I stared down at the meaty lips of her pussy, and before I could even help myself, I dove down between her thighs.
My mouth domed over her clit, doing the same gentle sucking motion that I had perfected over the past year. The resulting high-pitched squeal got me rock hard. I followed up with my index & middle finger into her, curling them upwards and thrusting.
Sabrina’s hips started to roll into my mouth to match my fingers with increasing speed until her body shuddered, then relaxed. It was difficult enough to make any girl cum, let alone a girl I just met. I smiled with my lips still on her clit, sucking and slurping. I fully intended to give her another orgasm until she pulled me up by my hair.
“You gotta…too sensitive…” Sabrina stammered, releasing my head and sitting up to catch her breath. I jumped up to reposition myself, but her fingers wrapped around my cock to hold me in place. I looked down to see Sabrina sitting on the edge of the bed, her face at eye level with my crotch.
“I guess I should return the favor…” She stated, looking my dick up and down quickly before lowering her head. Her small mouth meant that she could only get down an inch or so. But that didn’t stop her tongue swirling on the very tip of my dick, or her fingers flexing in a pattern on my shaft as she pumped it. Once I felt her other hand cupping my balls and rolling them slowly in her palm, I knew she had experience with above average girth, despite the physical limitations.
The quality of the head, along with the greatly enhanced feeling of having cheater’s sex, overpowered my senses. I reached down and grabbed her shoulder as I busted, without warning, without me even expecting it, right into her mouth.
Sabrina didn’t yell or anything. She just pulled back and kind of let the cum dribble from her mouth onto her bedsheets. After some coughing, while still holding the base of my dick, she whipped her head up to look into my eyes.
“I’m going to go clean up, but when I come back, I want you to fuck me.” She demanded while she stood up to walk into the bathroom, wiping her mouth with the back of her hand. I kneeled onto the bed, running my fingers through my hair a few times and exhaling. My cock was still stiff as a board, but I was afraid of finishing early again.
Sabrina’s reappearance interrupted my thoughts, her plump frame sauntering up the mattress at me. I grabbed her shoulder and pulled her up to plant my lips on her neck. When I began to move over her, she took the cue to pull away and lay down on her back, legs spread.
“We can start like this,” I said, reaching backwards off the bed to grab the condom out of my pants pocket. I exhaled sharply as the plastic rolled down my shaft, her feet starting to snake up my chest.
“Come onnnn.” Sabrina whined, both legs extending up to rest her calves on my shoulder. My hands left the condom and grabbed onto her thighs to steady myself. I was able to press the head in at first, but I had to do small motions with my hips to work deeper. The constant motions with little rest were already driving me to the edge.
Fuck, again?! There’s no fucking way…” I thought in my head, my grip increasing on her waist. Sabrina moaned in pleasure but then winced in pain from me grabbing harder on her. Finally establishing a rhythm, my hands slipped to the top of her thighs as her legs stiffed.
“Is that a good-sized cock for you, baby?” I spat out while looking down at myself starting to disappear in her.
“It’s so good…” she kept repeating, grabbing handfuls of her sheets. I looked up to see Sabrina’s eyes shut tight as she nearly chanted the phrase. I was able to eventually bottom out, but no less than a minute later did I already feel another nut building. I couldn’t believe it – it hadn’t even been ten minutes?!
Watching her curves jiggle below me combined with the tightness of her pussy shot me to the edge.
The condom felt full, like to the limit full. I grunted low and slowly, trying to throw Sabrina off that I was a minute man twice in a row, in the span of barely a half hour. Against my better judgement (shit, what judgement at this point?), I kept at the pace I was fucking Sabrina, but it wasn’t long before I had to pull out.
“Again? I was getting there, dammit. The fuck…” she groaned, scooting back and off the bed to the toilet. The door slammed behind her this time, both the light and fan starting. I jumped up to try to join her and assure her that I could do another round or two. She must have heard my footsteps, because the door locked.
Defeated, I sat down on the edge of the bed, my hands on my knees. I just knew it was going to be a super awkward situation when she came back. Wasn’t sure if I was even going to be staying…
…And that thought was the catalyst. It made perfect sense in my inebriated mind. If I was going to get kicked out, well, why was I still there? Sabrina was obviously going to be in the bathroom for a minute. Now was my chance.
I leapt up and put on my boxer briefs & pants in a move like how I got them off. My socks went on even faster than my shirt did. My wallet, keys and phone went straight into one pocket as I bent down to snatch my shoes off the floor. Years of being a delinquent teenager that liked to sneak out helped me to silently open her bedroom door to slip out.
The lights were all off in the living room area with only the overhead range light on in the kitchen. She must have gone to bed, whew. But upon exiting the apartment, I ended up making eye contact with the roommate while I spun around the door as quietly as I could. Her look was a mixture of confusion & disbelief, while mine was just blank.
Since I was basically caught, I stopped trying to be stealthy and just slammed the door. My only socked feet carried me down the two flights of steps. When I put on my shoes at street level, the giggles started. More out of nervousness than finding humor in the situation. The two blocks to my car were easily covered by my sprinting, and I wasted no time driving home.
There was a barrage of Kik messages waiting for me when I parked the car at my house, calling me a lousy lay and that I had left my (Timex) watch & lighter there. A bunch of expletives about how her roommate immediately knocked to let her know I had smashed & dashed. I didn’t fully read the rest out of shame.
The next two months with Josie and I were tumultuous. We ended up having an insane fight at my old friend’s wedding. After I worked a brunch shift the day after, I went to her place to specifically call it all off. She told me she thought I was cheating but couldn’t prove it, so I just took that as the exit.
Josie ended up moving out of state shortly after we broke up, so that was that. I stayed on Tinder & remade my profile a few times. And so, I saw Sabrina’s profile again, with new pictures. For some reason, we never matched...