[MF][Cheating]Slept with high school sweetheart years after we split up.

This happened many, many years ago. AOL instant messenger was all the rage, to give you an idea. I’d say this was about 1998-1999, give or take. Keep in mind that I’m not justifying our actions here…I’m just explaining what happened. And 20 years later, I still have fond memories.

Jessica and I were high school sweethearts, and ended up breaking up for reasons largely related to me being a complete idiot. We were teenagers, we’d fight over stupid shit because that’s what teenagers do, and we’d blow stupid arguments out of proportion. But this isn’t about that.

A few years after graduation, I saw her for the first time working at a shop in a mall a few towns over. I was expecting the conversation to be awkward, but we ended up chatting it up like nothing ever happened. And I quickly realized that everything that attracted us to each other the first time was still there. We quickly started to click. After that first conversation, I made excuses to conveniently show up at the mall right when she was closing. I’m sure she realized my excuses were full of shit, but she didn’t seem to care.

She explained that shortly after graduation, she quickly met and married someone. A bit older than she was, owned his own business, etc. And she was miserable. He was a workaholic, they got married before they really got to know each other, and they weren’t really all that compatible with each other. And he really didn’t do it for her in bed, leaving her frustrated.

Since she always worked the closing shift, and nobody knew her husband anyway, we were pretty safe at the mall. The customers were gone because it was closed, and the employees didn’t know or care who either of us were. Walking led to holding hands, which led to making out, and this became our thing. And when we weren’t doing this, we would be on AOL. And this is where things would really get steamy. We’d typically jump on AOL right after we got home, and the conversation would quickly evolve into full-blown cybersex. And she was a lot more into it than I thought she would be, as I could sit there for hours going into great detail about what I would love to do to her pussy.

I’m sitting there in the middle of one of our usual sessions, where I mention that I was going to head over to her house and do all sorts of sexual things to her. For whatever reason, this is where she drew the line. Long story (OK, longer than this already is) short, she said that this wasn’t real. We’re just role-playing. We’re filling a void. But as fun as this is, she didn’t want to actually cheat on her husband. Our make-out sessions ended, and while the cyber-sex continued, there was to be no further mention of me actually going to her house. I thought of this as odd for several reasons — including the fact that I didn’t even have her address — but I didn’t want to make things worse, so I went along. She actually stuck to these rules for several weeks if not a couple of months. Eventually, she realized that she was being a bit irrational about things, and I was able to mention “stopping over” again without setting her off once she realized that this wasn’t even possible since I didn’t know where she lived. Normally, she’d reply to these comments with some kind of “you wish” reply.

So I was really surprised when one time, instead of making a snide comment, she actually replied with her address. To this day, I have no idea what changed her mind. At first, I thought she was joking. I said “Don’t tempt me. I *will* stop by.” She replied with “Why do you think I gave you my address?”. I said “You wouldn’t have the guts”. She replied with “Come over and find out”. Then she logged off. Hmm. What to do. Surely, this is a fake address. Or she’s going to log back in in a minute and laugh it off. Or she’s going to call me.

So I waited a few minutes. No call. She didn’t log back in. Fuck it. I hop in the car and head over, waiting for my cell phone to ring. No texting or data plans back then. I drove the entire way there expecting a call or expecting to find out the address was fake. Nope. I find her house and her car there. Her husband’s car was gone. I start walking to the house, still expecting this to be some kind of elaborate gag, or at least for her to call it off at the last second.

I knock at the door and she answers it. She’s standing there in a loose T-shirt and shorts. We both get this nervous look on our face. This is really happening. I think both of us were expecting the other to call each other’s bluff, and neither of us had really thought this through. She awkwardly invites me in. She starts showing me around the house as if I were just any other house guest, but the conversation is decidedly more awkward. We eventually make our way to the living room couch, where our conversation changes from short, awkward sentences to dead silence for about 30 seconds.

“Aw, screw it.” I will never forget those words. With those words, she immediately and passionately starts kissing me, eventually straddling my lap. Awkwardness went right out the window. She reached behind her and pulled her T-shirt over her head, exposing her tits. She had relatively small tits, I’d say about a B-cup, but she had areolas that easily covered half of them. I took one of her nipples into my mouth, and I found out that for all the talk I had given her about eating her pussy, nipple play seemed to get her going that much more. It didn’t take long before she started reaching between us to undo my jeans. I laid her on the couch and positioned myself on top of her, going back to sucking on her tits. By this point, my jeans were halfway off and she was playing with my cock. I start moving down from her tits and down her belly, fully intending to actually do all those things with my tongue that I had said in our chats so many times, but she stopped me. She wanted to fuck. Now. Apparently, all the nipple play had done a lot more for her than I had thought it did; about 30 seconds after I enter her, she grabs a hold of me, pulls me tightly to her body, and comes all over my cock. I almost instantly come with her. For a minute, I felt like a 2 pump chump, disappointed that the experience didn’t last nearly as long as I was hoping it would. But if she was disappointed, she did a damn good job of hiding it. After she caught her breath, we laid there for a couple of minutes playfully making out and still exploring each other’s bodies, with me still partially inside her. Eventually, we got up, cleaned ourselves off, and I left.

Our cybersex sessions continued for several more weeks, but this was the one and only time we got together, simply because our work schedules didn’t leave us with any more time. Ultimately, she and her husband would get divorced once he found out that she was also having an affair with one of his employees. He obviously did more for her (and for longer, lol) than I could and hey…more power to him. Not sure what happened to her after that.

Source: reddit.com/r/gonewildstories/comments/bdwga5/mfcheatingslept_with_high_school_sweetheart_years