[MF] The Time I Cheated On My Girlfriend With Our Waitress

This happened last fall. I just thought of it the other day because I got a text from her asking me when I was coming back into town.

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It had been ending for a year. Ever since we decided we could make a long distance relationship work. We couldn’t. Our face timing got shorter, our texts were spaced farther and farther apart, and I was almost positive she had started to fuck some dude she worked with at her restaurant. We had begun to fight a lot. Little snippy passive aggressive bullshit here and there, but then once or twice a week I’d randomly get a snap from her with a her finger in her pussy “come fuck me daddy.” I don’t know. It’s hard to end a relationship, even when it’s already ended and you both just need to accept it.

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We decided we needed a trip. Like the kind we’d take when we first started dating- something fun, out of town, a little boujie. We told each other we’d connect. Fuck like we use to fuck. Strip off all the grimy bullshit that accumulates on relationships that have grown stagnant. She needed to go to Houston for a wedding so I booked a room at one of the nicer hotels, and we planned to fly in separately and meet there. The week leading up to the trip felt like old times. She’d send me pictures. Outfits she wanted to wear. A pair of heels she had just bought. A picture of herself in nothing but the collar with a leash I had bought her years earlier- “In case I need to be taken for a walk.” We use to have so much fun. We did everything. Nothing was off limits. Nothing we said or did offended each other. It was like we floated above everyone and everything else. Their petty concerns. But for a year now it felt like all we did was navigate a minefield of hurt feelings or spent our conversations longing for a distant past or a seemingly unobtainable future. Sex had lost it edge. Sometimes, and this would have been unimaginable just a year earlier, we’d fall asleep watching Netflix every night during the weekends she’d visit me.

I got into the city first, checked in, dropped off my bag in the room and headed down to the bar/cocktail lounge for a drink and to wait until I needed to head to airport to pick her up. The girl who brought me my drink was named Ashley. Six hours later I’d have my belt around her neck while she demanded I fuck her like I paid for her.

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She had walked over and I looked up from the menu or my phone or whatever I had been staring at. It was one of those super hip hotel lounges and she was wearing a little black romper and white high top chuck taylors. She sat on the low table in front of me. “I like your hat,” she said and motioned to me with her lips. “Thanks,” I said, “My mom bought it for me,” which was clearly a lie and she laughed. I could see the outline of a stud through her right nipple. She was striking. Early 20’s and clearly italian. Short black hair with a small nose ring and a full sleeve of tattoos on her left arm. I told her about why I was in town. About the girl I was meeting and how I wasn’t even sure I wanted to be there. She told me about how she had been sober for a year and had gotten a job a yoga studio. She brought me a second drink and I asked her about a local musician I really liked. “Oh yeah!” she winked, “my dad loves him!” Her skin looked incredibly soft and she had begun to lean towards me when she talked. I could make out the bottom of a tattoo on her upper thigh. The bar was pretty empty and she ended up just sitting down across from me. We made fun of basic Houston girls in Lululemon pants. She asked me if I wanted to go two-stepping after she got off work- “you know… if things don’t work out tonight with that girl.”

“Sure,” I said, “if things don’t work out…”

“I’m Ashley” she said pointing at a her name tag that clearly said “Kelly”

“What is this, a fucking strip club?” I laughed.

“Just call me if things go as bad as I think they are going to go tonight,” and she gave me her number.

I told her I needed to go to the airport and paid my check.

Things did go bad. We fought. We fought about arguments from years before. From weeks before. We argued about arguing. We fought in one bar then went to another bar and fought there before we went back to the room and tried to fight, but there wasn’t anything left to fight about so she turned on the TV and pulled on my boots and went back to the hotel bar. Ashley was still working. She set down a napkin then my water. “You’re back,” she deadpanned. I smiled and rubbed my face, “fuck off” I laughed. Ashley handed me a menu. The bar was empty again and it was 10 mins until it closed. “She’s pretty,” she said, “really fucking pretty. I watched you guys walk back to the elevators.” She was standing too close to me and was tapping the menu on the bar. The bartender seemed to have disappeared. She smiled and leaned in close, close enough I could smell gum and cigarettes on her breath. she gave a little eyebrow raise and smirk “You just fuck her?” she asked. I laughed and ordered a drink.

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Then an hour later we were drinking coors light at some dive bar. Her arms wrapped around my neck as we slow danced to to some dude covering bon iver and my hands slid over her ass and I could feel her press her body into mine and I knew it was just tonight and that I was blowing up a relationship but I didn’t care and her mouth was on mine and I felt light and happy as her tongue slid between my lips and her hands ran through my hair and I didn’t care about my girlfriend back in our hotel room. Her breasts felt heavy as she pressed herself into my chest. The singer took a break and she pulled away from me a little bit. “How old are you,” I asked and suddenly realizing how young she looked. She let go of me completely and grabbed her beer that had been sitting on the lip of a pool table. “I’m 23,” she laughed and finished the coors with a last swig, “you’ll need to buy some condoms. I don’t have any at my place.” And 30 minutes later I stepped into her studio apartment downtown. And she closed the door behind me. The air conditioning clicked on. She stepped into her bathroom.

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We had talked about how she liked to be fucked, but I’m always hesitant to go really hard on a girl I just met. She had told me in the car, as we drove to her place, she could only cum if she was being slapped. That she loved being called names. And while I’m really into all of that- it feels weird to bring your hand across essentially a strangers hand the first time.

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She stepped out of the bathroom totally naked. Like totally fucking naked. God her tattoos were perfect. A mandala on her hip that ran up her side. A small cluster of roses on her her thigh. I ran my eyes up and down her body as I slowly pulled my belt out of jeans. She stood there the bathroom light casting a silhouette around her. Perfectly smooth except for a small landing strip directly above her cunt. She reached up and put her curly black hair into a pony tail as I stepped closer to her. I smiled. She smiled. God her body was fucking beautiful. Her slightly crooked nose. Deep brown eyes. My hand wrapped around her throat. Tentatively at first as I pushed her into a wall next to her bed. “Like this?” I demanded as I held her against the wall. We had talked about how much she liked being choked, but I always feel slightly weird that first time my hand wraps around a girl’s throat. She nodded and winked. She kept her hands behind her head. My belt was in my other and she pushed her hips towards me while I kept her neck and shoulders pinned to the wall. I kissed her deep and instantly her tongue was in my mouth. Her body squirmed as I tightened my grip on her throat and ran the smooth edge of my leather belt up her thigh across her pussy before giving it a light smack. She smiled and her eyes lit up. I quickly flipped around and firmly, but gently pushed the side of her face into the wall. She instinctively locked her arms behind her back and pushed her ass and hips toward me. “We still good?” I asked as I ran the belt over her ass. She laughed, “You’re at like a 3,” she matter-of-factly said, “and I’m good until we hit a 10.” I crack the belt across her ass. It instantly left a red mark. “Like that?” I demanded. She laughed again “Getting warmer, Tommy,” she whispered, almost to herself as I brought the belt down against her again.

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I pulled off my clothes and threw her onto the bed. “Where are we at?” I laughed as she pushed herself up on her elbows, her legs spread apart. Her pussy was fucking glistening. “Um” she ran a hand down her thigh, “about a 6.. ish?” I was standing over her by then, my hand pressed against the ceiling, and before she could say another word the back of her head was pressed into the headboard and my cock was in her mouth. She closed her eyes and gagged as I pushed into the back of her throat. Her spit ran down my dick and onto her chest as I pistoned in and out of her mouth. I didn’t even fucking think about my girlfriend. I dropped to my knees in front of her and without thinking grabbed her face, drool dripping down her chin, and rubbed my hand across her mouth, her nose, her eyes- her eyes lit up and she spit on my chest. I laughed and let go of her, running both hands through my hair. My fucking cock throbbed. All I wanted was to be inside of her. “God damn you’re a fucking whore,”I muttered and reached over grabbing my belt and looping it around her neck. Keeping it loose at first. “Ashley,” I took a second to check in, deescalate, “we still good?”

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She slid her body around so she was on her hands and knees. “Shut up, and fuck me like you paid for me,” she matter of factedly said as she pushed her ass into the air, “You’re not even close to making me uncomfortable.” I pulled the belt a little tighter around her neck and she pushed her face into the bed. I reached over, undid the wrapper of the condom with my teeth and free hand and rolled it over my dick. She spread her legs and I pulled the belt back, pulling her head and neck back with it and slid into her dripping cunt. She was so fucking tight and warm and wet. God she was tight. “holy fuck!” I muttered as I wrapped the belt around my hand, and pushed into her her lower back with free hand, “This pussy feels ridiculous!” she rocked her hips back and rode up and down my dick as I pushed as hard and deep as I could into her. I smacked her ass over and over again. She didn’t flinch. “This is what you like?” I demanded. “This is what you get paid for?” She just fucked me harder. “Say it!” I was having a hard time not laughing, she felt so good. “Say this is what you like you silly bitch.” For a second I thought that might have gone too far.

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She pulled her head off the bed, the belt still tight around her neck. Her ponytail had come mostly undone and her hair looked wild. “Yes, sir” she moaned. “this is what this stupid little bitch wanted.” That response. That fucking response! I pounded into her as hard as I could. pushing her body into he headboard. I let go of the belt so I could grab her waist with both hands. My fingers locking into her hips. Holding her body so I could use her pussy until I came. She collapsed under me and I stayed inside. Pounding her body into the bed as she lay completely prone under me. The bed was fucking bouncing up and down with her body as I moved in and out of her. Fuck she was loud. She was literally screaming into the mattress. Her hands at pulled so hard at the sheets they had come undone from the bed and still I put all my body weight into every thrust. She pulled her head up, “Keeping going” she muttered, “don’t fucking stop! I’m going to fucking cum. Her hand was under her rubbing her clit as I slid in and out of her. And then like that I could feel her body start to quiver. Her legs tense under me. She buried her face back into the bed and then slammed her fists over and over again into mattress. “Fuck!” she screamed loud enough that I worried her neighbors would stomp on the ceiling. And then she collapsed. Her body felt limp. I pushed into her several more times. I had held off as long as I could I wanted to explode. “Fuck,” I muttered, “I’m going to cum.” She reached back and grabbed her ass with both hands, her fingers digging into herself, pushing her hips up towards me. I buried myself as deep as I could and felt my cock spasm into the condom as she pushed her body against my hips. It felt like I fucking filled it and slowly pulled out of her. I rubbed my face and she rolled over, gingerly undoing the belt from around her neck. Both of us were wet with sweat and I was breathing heavy. She reached up and pulled the condom off, laying it on her nightstand. I was 2 am. She smiled at me. and slid both of a hand down her body, mindlessly, and slowly rubbed her pussy. “You can’t stay here,” she said, “Don’t you have a girlfriend back at the hotel?” I felt a sudden stab of guilt, my dick still slick with cum.

Source: reddit.com/r/gonewildstories/comments/caqrf5/mf_the_time_i_cheated_on_my_girlfriend_with_our