“Cheating On My Longtime Boyfriend With A Redditor, Who Knew How To Fuck My Ass” [M/F] [Long] [Anal] [Cheating]

“Cheating On My Longtime Boyfriend With A Redditor, Who Knew How To Fuck My Ass”

My boyfriend and I have been together for close to eleven years. I love him. I love him so much. Something happened last week that has consumed my thoughts, since it happened. What I did was so out of character for me. Everything about it got me so hot, even thinking about it now. I think a lot had to do with the whole naughtiness of it, and the ‘not getting caught’, got me so turned on. I’m wet thinking about it. I would have never thought that I’d do something like this in my life.

I’ve always been the good girl. I always did what my parents wanted, or expected, of me. When it came to my boyfriend, I always went out of my way to make him feel special. Whether I wanted to or not, if he enjoyed something, sexually, I did it, for him.

I’m a tiny girl. Petite, if you will. I’m 5’2”, and weigh about 108 lbs. People tell me that regardless of my size, I still have the body of a woman. Good hip to waist ratio. Smaller tits, but, I’m not complaining.

My boyfriend, Mark, and I have been together since we were 14. We’re both 24 now. My bf was the only one I have ever been with. He slept around on me a couple times when we broke up, for a week or so, in those ten years, but, I always forgave him. It still made me jealous, though. Like, I didn’t know how to do anything to please him like those girls did. I’ve even caught him texted back and forth with one of those girls. Yet, I stay with him. Like I said, I love him. I’ve always been faithful, until recently…and I want to do it again..so bad.

Mark and I live together. We spend most of our evenings in our own little corners of the apartment. He likes to play video games. I usually go on social media. You know, Facebook, Instagram, Kik, etc. I recently joined Reddit, and that’s when things started to change for me.

I didn’t even know there was an “NSFW” section in it. I kinda stumbled on it, and once I did, I was hooked. So much content. I like to read, so naturally I started reading some of the naughty stories. I never knew I could get so turned on by a simple story. That first night I was reading some story about a farmer who was having sex with his daughter’s friend. Yes, she was over 18, but it was so hot. The way that this writer explained what the farmer was doing to this girl, got me so wet. It was like an eight minute read, and by the time I was done, I was rubbing my clit through my sweatpants. I re-read those last three paragraphs over and over. I found my hand inside my sweats rubbing and fingering. Faster and faster until I came. I have to admit, I don’t think I ever had an orgasm from reading a story… I was hooked. I wanted to read more.

A day or two went by, and I couldn’t wait for my bf to go out with his friends. Because when he left, I was going to give myself another orgasm. Mark could give me one by going down on me. But, he’s only gone down on me, like, five times, in the ten years that we were together. When he left for the night, I waited twenty minutes or so, in case he came back for something he may have forgotten. He didn’t come back.

I was so horny, and nothing was doing it for me, except for the stories that I came upon. Especially from this u/ThatDirtyStoryGuy writer. Yah, it was exactly that, I believe. His stories were fantastic. They got me so turned on. This particular night he just a had a short confession or something about this young girl that took it in the ass from everyone in her neighborhood. So lust filled, but I enjoyed it.

I ended up messaging him, to tell him how I liked it, and how his stories got me so wet. I felt sneaky contacting another man, that’s not my boyfriend, where sex was involved. Yet, being sneaky was turning me on. When he responded, he asked if it got me wet. I figured there was no harm in telling someone, whom I didn’t know, what it did to me. I wasn’t planning on going into great detail. At least, that was the plan.

We started messaging back and forth. Turning each other on. He then started to ask me some personal questions, that I really didn’t mind at this point, because he continued to tell me, what I wanted, or ‘needed’ to hear. I’d sit there and rub my clit and finger my pussy while I chatted with this guy. I found out his name was Roger, and he was 42 years old. That really turned me on because I always had a fantasy about being with an older man. Not that I had plans of having sex with this man, but one can fantasize. I just kept thinking an older man probably knew just what to do, to please a woman. He writes so good. I’m sure Roger knew just what to do. Night after night I talked with this man. I sent him photos of myself. I even sent him naked ones, which he loved. He seemed like a very good guy.

Mark never caught on. I got really good at hiding what I was doing. But, when I was talking to Roger, or reading one of his stories, I always had my hands down my panties. Sometimes even in the bathroom at work. In one of his stories there was even anal sex going on in a really hot way. I never, in my life, wanted to put something up my butt, yet I wanted to feel what this girl was going through in the story. It was really, really, good. By the time I got to the end, I had my shorts and panties on one ankle fingering my tight little asshole while rubbing my clit. I came thinking about this older gentleman, Roger.

There was such a strong part of me that wanted to meet him. I ended up asking him where he was from, and when he told me, my jaw hit the floor. He was only 30 miles north of me! That night I had to seriously think about what my next move was going to be. I mean, I did say, I love my boyfriend, but this lust for this older man was consuming me.

After a day or so, I thought of my decision. I was going to meet Roger, but, not for sex. I just wanted to meet him, and shake his hand on being such a good writer. Yes, that’s it. That’s exactly what I wanted to do. Just ‘meet’ him.
I mean, I would tell Mark, if I had to, because nothing was going to happen. I just wanted to fuck this man’s hand. Excuse me, “shake” this man’s hand.

After talking to Roger, we decided to meet at a public park. Sounded fair. People could be around, so nothing was going to happen. I couldn’t believe I was doing this, but, just something in me couldn’t stop. I could of turned the car around a few times, thinking of my boyfriend. Although I kept telling myself nothing was going to happen, the thought of that time Mark messed around with a girl, when we broke up, or his secret texting, just seemed to justify this meeting.

I made sure I covered all my steps before I even left. It might not of been the smartest thing, but, I didn’t tell anyone where I was going. In fact, not a single person even knew I was talking to Roger. Just him and I. That’s it. No one had a clue. I even shut off my location finder on my phone. I didn’t want to get caught. Even though, the whole “secret” thing turned me on. I loved being secretive. It felt so dirty, and naughty.

In the short 15-20 minute drive, it was mostly old country roads. I started to play with myself while driving. It was a warm day, and I had on tiny shorts. My ass cheeks were visible at the bottom of these shorts. I like to wear skimpy clothes. Some people may get the wrong idea about that, but, I just feel the most comfortable wearing stuff like that. My boyfriend always tries to make me wear less revealing things, and I usually do, to not cause a fight. I was just so excited or something, I couldn’t help but rub my clit through those shorts, causing a wet spot on them. I tried my best to point the air conditioning vents down toward my shorts to dry them up, in the last few miles of my trip.

When I arrived at the park, I had to drive all the way up this long road, going 15mph, looking for the particular pavilion he was going to be waiting. When I got there, there were only a couple cars in the parking lot. There was a walking trail, and also a biking trail. I guess those cars belonged to the people enjoying the trails.

Then, there he was. This man. Roger. He was walking towards me. He was so hot. I’d say he was about 6’1”, or 6’2”. He was fit. He took care of himself. I felt like a school girl. Roger eased my tension right off the bat by giving me a big hug….I needed that hug…

We sat at a picnic table and I was just getting closer and closer to this man that infiltrated my mind. I think he felt the same way. He asked if I wanted to go for a walk through the woods. I thought that was a great idea. My heart rate was rising. My plan was changing in my mind. I’d do whatever he wanted to do. Even though, I think I knew I would, all along.

While we were walking, he grabbed my hand and took me off the trail. He said there was a lookout view that was breathtaking of the valley and river below. As we were stomping thru the brush, I was following his lead, walking where he walked, because I had short shorts on, and I didn’t want to walk through something poisonous. Finally we came to a clearing. Roger was right. It was beautiful, and so was he.

I was pointing out a boat on the river, when I felt Roger behind me. His fingers went through my hair. I could feel his breath on the back of my neck. This wasn’t Mark, and it turned me on, that it wasn’t. I knew where this was going now, and I was going to do it all. Roger put his hand past the elastic band of the back of my shorts, and ran his middle finger down the center of my ass, parting my cheeks with his ring and index finger, until that middle finger found my sticky orifice.

He started biting and sucking on the back of my neck, while his free hand unbuckled his belt, unzipped his pants, and pulled out his cock. That same hand, that just unleashed his dick, went down the front of my shorts. Doing a similar thing with that hand, he separated my lips, going past my clit, and circled his middle finger on my opening, and slid his thick finger in my pussy. I gasped. His other hand moved its way underneath me, coating his finger with my pussy juice, and returned to my asshole and circled that hole like his finger was going down a drain.

Mmmmm. I was so turned on. I reached around and felt for his cock, and there it was. Mmm. So big. So hard. Roger kept fingering my pussy when he took his hand out of the back of my shorts and pulled them down, along with my panties, right under my ass cheeks. I rubbed his wet dick on my bare ass. Mmmm.

Roger pulled my shorts down a little more, took his sopping wet fingers out of the front of my shorts, pushed my back down so I was bending over. There was a stump from a fallen tree in front of me, that I put my hands on to brace myself for what was coming. I closed my eyes, and thought everything I fantasized about was coming true.

He lapped his cock on my pussy, mixing his natural lube with my own and entered me. Immediately I knew it wasn’t Mark behind me. Everything was different, and not at all predictable, as if it were Mark. He buried his dick in me, separating my petals. Oh, God, he felt so good in me. He was pumping me pretty fast. Bottoming out with each thrust. Roger took his hand and forcefully pulled down the front of my shorts and panties and started to rub my clit. I wasn’t very loud, but I said under my breath, “Fuck me…oh, I know you’re good, fuck me, make me feel like I’m cheating. Fuck me like I’m one of your girls..”

Roger pistoned his cock in and out of my pussy. Other than the lustful sound of wet fucking, it was silent in the forest. I think all of the animals were paying attention to what was going on. Mmmm. “Just like that, don’t stop, I’m cumming!” I let out as my body started to convulse. I had to move his hand off of my clit. “Jesus, damn, so good.” I said, breathing heavy.

Roger pulled out, leaned down, pulled me upright, kissed and sucked on my neck, and worked his way down and licked the side of my ass. He was nibbling and biting my peach, and used his wet, lubed tongue, licked straight up the crack of my ass, essentially wiping me. Mmm. That was a first. I never felt a tongue anywhere near my asshole. Mark thought it was dirty. I thought it was dirty also. But, dirty in a naughty way.

Roger licked up a few times, soaking my asshole. I could feel the tip of his tongue with his taste buds on the inside of my ass. So f’ing good. He spread my ass wide with his hands and sucked on my lubed, relaxed exit hole. That licking, sucking, and smacking were the sounds coming from our two bodies in the woods now. “Oh, Jesus, feels so good! Mmmm. Eat my dirty ass. Suck on it!” I let out, loving the reality of my fantasy coming true.

Having a tongue in your ass is something that is so hard to describe, but it feels so incredible. Roger was exploring my insides so deep with his tongue I could feel his prickly day old facial hair on my tender butt.

I could hear and feel him breathing thru his nose as he tongue darted in and out of my asshole, loosening me up. I had my eyes shut, enjoying this so much. The sensory nerves in my rim were sending pleasure throughout my entire body. With a couple more smacks with his lips and tongue, he exited my brown eye, breathing heavy on it, cooling the saliva that was on the inside, and all up and down of my crack.

Roger didn’t waste any time. He was in lust mode. Coming up from below, he turned my face and sucked on my tongue. I could taste the slight bitterness of my asshole in his saliva. I didn’t care. It turned me on. I was a cheating slut, and I loved it. I knew Mark was never going to find out about this, which turned me on more. Here I was, in the woods, 20 minutes from our house, about to get my ass fucked by a stranger, while my boyfriend thought I was at a Doctor’s appointment or something.

Roger put the very tip of his glistening wet cock on my willing anus. I instinctively leaned forward and moved my hands and spread my ass as far as I could. I was surprised how easily the head slipped past my rectal ring. I was just so relaxed and loose. I was being filled with his meat, and I could definitely feel it. The pressure was intense, but it hurt in a good way. I was such a slut. His cock slid in all the way. I gritted my teeth. My ass was getting fucked. God. Such a cheating slut. My shorts barely pulled down past my cheeks, with a 42 year old’s cock going deeper in my ass. I felt every millimeter going in.

I could feel my asshole stretching out as he guided it in slower, going in all the way.
The head of his dick made it to the uncharted depths of my colon. It hurt, but the pain, for some reason, actually felt so fucking good. My ass was being split in two, and I fucking loved it. I loved the pain. The more I thought about WHAT was in me, the more I wanted him to start banging the shit out of me.

Roger then began to back out. Shit. I liked backing out. So familiar and orgasmic. I was finding out, cock in the ass feels so good. Mmmm. Back in he went. I started to play with my swollen clit. It was such a strange feeling getting penetrated, but not feeling the familiar pleasure coming from where my hand was, but, instead, further back, in my ass. “Fuck me hard. I deserve to have my cheating ass fucked hard..” I begged, even if it hurt.

Roger took my words and really started to fuck me. He was letting go a lot of sexual lust that he had with our back and forth sexting we were doing in the past few weeks. He was going all the way in, and almost all the way out, before jamming his cock back in my tiny ass. I had tears in my eyes. I deserved having a stranger’s cock in my cheating asshole. It was so intense. He was pumping me so hard with his big dick, I whimpered and moaned. When he slipped out, it was orgasmic. Electricity shot through my body originating from those nerve endings in the ring of my asshole.

Roger’s balls were slapping off my upper, inner thighs. My hand, at this point, was going crazy on my pussy. For some reason I imagined I was being fucked in the ass by one of his characters from one of his stories. The man that wrote those stories, was the man pounding my ass. Pounding my ass, hard. The thought turned me on so much. I reached underneath myself just to feel the girth of his cock magically disappearing in my asshole. My gape sounded so loose. So bored out.

The rush was building. I could feel it. Shit. This was different. Completely different. I could actually feel that my ass was going to cum. “Fuck me Roger! Fuck my butt! You took my ass virginity. Shit! Make me cum!” I let out as Roger plowed me. I came just as I could feel Roger picking up speed. He was about to cum just as my body was shaking. I clinched my ass. With one solid fucking thrust, Roger exploded, what initially, felt like a gallon of his hot cum deep in my exit tunnel. Mmmm. You have no idea how good it feels to have hot cum bounce off your insides. Such a fucking turn on. It only feels this good when you cheat, I swear. It’s the pure lust.

Roger continued to thrust into me when he ejaculated, filling me up more. I could feel his hot lava coming out the sides of my lust hole and running down the inside of my thighs.

Roger was moaning. I could literally feel and see his cock moving, on the inside, under my belly button. He moaned one more time when he backed his throbbing cock out of my ass as it milked the last few drops from his drained balls, deep in my lower bowels.

When Roger exited me, I immediately wanted to feel how loose I was. I could easily stick my fingers in there and feel the soft walls of my anal cavity. Mmmm. Roger leaned over and kissed me again. I couldn’t get him in me enough. I just cheated on my boyfriend of eleven years with this man, just about old enough to be my dad. Here I was, in nature, with my girlie shorts barely pulled down past my naked butt, that just got her ass destroyed by a man that turned me on like no other, by convincing me that it was worth it all, to do it again and again..”
THE END (*This story was fiction)

Well, I hope this story turned you on. If it did, I would love to hear about it. Seriously. It turns me on, turning you on. Pm me. I don’t bite. I’ll talk to you the way ‘you want’ me to talk to you….I hope you enjoyed it. I wrote it for you, after all. Take care. Love you all!

Source: reddit.com/r/eroticliterature/comments/dnqmir/cheating_on_my_longtime_boyfriend_with_a_redditor