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First Time I Cheated

"Story of my first time cheating on my partner"

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2.7k words 2.7k words

Author's Notes

"The story about the first time I cheated on my boyfriend."

Some context to this story is I was assaulted and didn't want to have sex for a bit. I told my boyfriend and he was sympathetic and understanding. Soon I started wanting to have rougher sex and he was unable to really get into it. Our sex life was vanilla, and I was fine before, but it wasn't satisfying me anymore. He is great otherwise, supportive, funny, smart, great to talk to. I was pretty much only fantasizing and masturbating to the thought of rough or forced sex, and began to consider having something on the side.

I felt so guilty, but eventually, after thinking about it, I decided to download some dating apps. I set up my profile and was really feeling guilty as I knew it was wrong, but it also was exciting. My bf was the first and only person I'd been with at this point, and I've never used dating apps before. I got some matches and most didn't go anywhere. Mostly I was too nervous to do anything but talk about my fantasies.

Eventually, I started sexting with some guys just through text but later through some pictures. They were tame at first, just pictures in my underwear but it was so exciting. It escalated and I started sending some nudes. I knew my bf would be devastated and I felt guilty, but it didn't exactly feel like real cheating even though we both would consider it cheating.

I pretty much ghosted all the guys because I was too scared to go further. I went back and forth between deleting the apps and re-downloading them. I started to fantasize more and more about hooking up with a stranger until it was all I fantasized about. One day I was back on the app and usually, I'd do some sexting, masturbate, and cum and delete the app feeling satisfied and somewhat guilty. This time I stayed wanting more and I didn't delete the app after sexting. I matched with this random guy and we had an instant connection.

Our conversation was flowing and we were into a lot of the same stuff. We talked about spanking, choking, face fucking, and him being dominant and me being submissive in general. He asked me to come over and something inside me said that this was it and I was going to take the plunge and meet up with someone. I had been thinking about it for so long and I wasn't completely ready, but I didn't think I ever would feel ready and told myself it was time to go for it because it was on my mind all the time.

I got in the shower, put on some new clothes, and hopped into my car and headed to the address he sent me. My heart was beating out of my chest and I couldn't believe what I was going to do. I was nervous and excited. I was thinking, what if this guy is a serial killer, what if he isn't as respectful as he said he is, what if I hate it. But I just kept driving there until I parked outside his place. I picked up my phone and let him know I was there. He responded instantly saying to come to the door.

He was mid-twenties, tall, decent looking. Certainly not the best-looking guy, but I liked his energy and vibe. I don't know it just felt like I could trust this complete stranger I talked to for just under an hour. I got out and walked to the door asking myself what I was doing. I was so nervous, but also excited. I could feel myself getting turned on with each step I took. My heart was racing, my breath picked up, and I could feel myself getting a little wet down there. I knocked on the door and in what felt like forever he opened it and welcomed me inside. 

He guided me to his bedroom and I sat on the bed feeling awkward. He complimented me and then sat next to me and put his arm around me. He asked how I was feeling and I told him I was nervous. He said not to be as he rubbed his hand on my thigh.

My breathing became sharper as his hand ran up and down my thigh and I could feel my pussy tingle as he went up my thigh. He took his hand off my thigh and touched my cheek and turned my head to face his and he went in and kissed me.

I didn't kiss back, not right away. I was thinking oh my God I'm doing this. It's too late to back out. I started to kiss him back and he gently pushed me onto my back and got on top of me. He slid one leg between mine as he put his hands on my face. Soon he put his other leg between mine and started to grind on me. It felt nice and I forgot about my boyfriend as I started to be more present. I wrapped my arms around him and we started making out.

He started kissing my ear and neck before kissing down to my tits. He groped them and pulled my top down and felt them over my bra. He pulled that down too and felt my hard nipples. He sucked them and it felt really good. Eventually, he removed my top and took off my bra and continued to play with my tits. He kissed down my stomach until he got to my jeans. He kissed around my pussy over my jeans before unbuttoning them and pulling the zipper down. He stuck his hand inside my jeans and rubbed my pussy over my underwear. He kissed me as he rubbed me and told me it seemed like I was enjoying it. I giggled in response as he grabbed the sides of my jeans, lifted my hips, pulled my jeans off, and tossed them on the floor. My socks came with them and I was left just in my black panties with this stranger who was going to have his way with me.

The thought of that excited me and I became more turned on. He kissed me, down my neck, to my tits, down my stomach, down to my pussy, almost to my asshole, and then the insides of my thighs. I could feel myself getting wetter and more relaxed. He returned to my pussy as he kissed it and rubbed my clit. He told me I was soaked and I let out a little laugh. He continued to rub me up and down and right up to my asshole, before hooking his hands on the sides of my panties. I lifted my hips and he peeled my panties off of me and tossed them on the floor.

He let out a sexy moan as he saw my pussy and went in and licked my clit. He ate me out and stuck a finger in me as I moaned and ran my fingers through his hair. Soon I could feel an orgasm building and I squeezed his head with my thighs and gripped his sheets as I came with him licking my clit and fingering me. I moaned and let out an oh fuck as I came. He got up and licked his fingers and told me to get on my knees.

He pulled his shirt off and told me to unbuckle his belt and take his pants off. I slid them off and I could see his semi-hard cock in his boxers. He told me to take it out, so I pulled his boxers down and his dick sprang up. He kicked off his pants and boxers and told me to suck it. I took the base of it in my hand and took the tip in my mouth. I sucked and licked his tip which had some precum and took more and more of it in my mouth.

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He ran his finger through my hair, grabbed it and pulled it down. He commanded me to look at him and I did. He pushed his dick deeper into my mouth and throat as he pushed my head down until I had taken it all.

I gagged but he wouldn't let up. He called me a good girl and eventually pulled my head back to just the tip in my mouth only to push my head back and have me deep throat him again. Soon he was fucking my mouth as I gagged and had tears starting to stream down my cheeks. He pushed my head against the bed and proceeded to fully face fuck me harder and harder as his balls slapped against my chin. He pulled out and I gasped for air as he put his cock along my face and his balls on my lips and told me to suck them. I did as told and sucked them and then he went back to face fucking me.

After that he sat on the bed and told me to stand up. He grabbed my hips and pulled me to his side and bent me over on his lap. I told him I had a boyfriend so he knew about my situation and said that I was naughty coming here as he rubbed the back of my thighs up to my ass. He caressed my ass until he took his hand off and spanked me. I felt so vulnerable with my bare ass sticking up and my face, hands, and hair dangling. He continued to spank me and said I should be punished. He made me thank him for spanking me which made me feel so dirty.

He grabbed me under my arms and lifted me only to throw me back on the bed bent over and got behind me. I could feel his dick between my ass cheeks running along my pussy. I felt him position it and then I felt it slide in filling me up. He pressed down on my back as he fucked me hard and fast straight away. I was a bit in shock from how it started to how it was going, from him being tender when he ate me out to roughly fucking me. I couldn't help but moan from a bit of pain as he went hard and fast right away.

He continued to spank me as I was feeling a bit overwhelmed. I didn't even have time to process right away that this was it, I was officially having sex with another person. He grabbed my hair and pulled it back as he pushed down on my back.

He laid his body on top, reached around to grab my neck, and choked me. His hands were big and I'm tiny so his hand reached both sides of my neck as he choked me and pulled my hair back. I felt myself go a little lightheaded as I stared straight ahead. It was all so intense getting rammed by a stranger and now he's choking me. He let up on the sides of my neck and I could feel blood returning to my head but he choked the front of my neck and made it hard to breathe. My mouth was wide open as I was gasping for air. I thought to myself, Well this is what I wanted, what I asked for, but it was much more intense than when I choked myself while masturbating.

Eventually, he loosened his grip only to make it tighter all around my neck so I got lightheaded and struggled to breathe. 

I moved my hands from laying flat on his bed to his hand but I couldn't move it. His other hand went to my tits as he was groping them. Eventually, he let go, pushed me up on the bed, and lifted my hips. He reinserted himself as he pushed my face down into the bed with my ass straight up. He told me what a great view he had as he spanked me and gripped my ass cheek. He grabbed my hair, pulled it back, and grabbed my hip with his other hand. He continued to pound me hard until he started grunting and I could tell he was going to cum.

I had stopped taking birth control and I told him to wait and not cum in me, but just as I said that he thrusted deep and hard and let out a loud grunt as he came in me. I didn't think about this part, just got caught up with horny brain.

He pumped into me a few more times before pulling out and then collapsed next to me. I stayed still for a bit before lying down and rolling onto my side next to him to look at him. He was on his back looking up and panting and I felt awkward again not knowing what to do. I always cuddled with my bf after sex but I didn't know if you do that during a hookup, or if he would even want to.

I lay there awkwardly without saying anything and he got up and got dressed. I watched him dress and he thanked me for coming over, and I told him it was no problem, not knowing what to say.

There was awkward silence after and I realized he was trying to kick me out without saying it. I got up, picked up my clothes, and got dressed. He let me know where the bathroom was and I went in and fixed my hair and peed. He walked me to the door, thanked me again, and gave me a hug.

I walked back to my car and drove home in a bit of shock. When I got home I immediately changed and buried my panties in my hamper as they had his cum in them that leaked out and I got freaked out that my boyfriend would find out. I took another shower and still felt spaced out but also the guilt of what I did started to set in. I blocked the guy and deleted the app because I was paranoid about being caught.

My boyfriend got home later and he could immediately tell something was off about me. I told him I was fine and he told me I was quiet and I didn't know how to act. Honestly, all my thoughts were about what I did and how guilty I felt I didn't know what to say. I still felt spaced out too. The guilt increased as we went to bed together and he cuddled against me not knowing what I just did. 

The next day I took plan b just in case and started to process more of what happened. I started to get turned on thinking about what I did and replayed the sex in my head as I touched myself. I masturbated and came as I imagined it happening again and again over the next week or so. I started thinking about all the different things I wanted to try and I was excited to do them. The guilt from cheating subsided with each day and it started to excite me that what I did was so wrong but also so hot. I started wanting to do it again and accepted that it would happen again which excited me. Sometime after the hook-up, I got sick and was convinced I had an STD, but I got tested and was clean and so relieved.

I went on to have sex with more men behind my bf's back as not only was the sex better as it satisfied my new kinks, but I loved the rush and thrill of cheating and how bad it is. Before, I only had slept with my boyfriend, but now I've had sex with over thirty men and a few women.

Published 
Written by squirrelinhiding
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