An affair with my high school sweetheart [MF] (Long)

I’m going to start by saying that I’m not going to try to justify my thought process or my actions. I’m just telling the story as it happened. This was back in the early 90s.

Jess and I were high school sweethearts. We had dated during most of my senior year in high school. We broke up largely due to us being young and stupid because we were young and stupid teenagers. Shortly after we broke up, her family moved a few towns over. Now this was just before the internet really became a thing, before either of us had drivers licenses (I didn’t get mine until I was 20), and when calling even a couple of cities over meant huge long distance charges. Which basically meant she might as well have moved across the country since there was no practical way for me to get in contact with her. I had regretted our breakup, but there really wasn’t much I could do about it.

A few years pass, and we’re in our early 20s. I take a drive to a mall in her town, and happen to find her working in one of the stores. She had filled out nicely….she looked better than she did in high school. She was now sporting a set of D cups and had all the right curves in all the right places. And she had a wedding ring on her finger. Damn. I figured I should still go up to her and say hi even if just for old times’ sake.

When I did, the connection that attracted us to each other was instantly rekindled. It was pretty obvious the attraction was still there. We kept our conversation to the usual small talk that people have when they bump into people who they haven’t seen in a while, but we could both tell we wanted to say so much more. We ended our conversation with the usual “We’ll have to keep in touch”. And I intended to. I of course found an excuse to have to go back the next day. And the day after. And it became pretty obvious pretty quickly that she was looking forward to my not-so-random visits.

We exchanged AOL screen names. We started getting a little more personal in our conversations on AOL. When it came to her marriage, she had said that she quickly met and married someone a month later and almost instantly regretted it. Her marriage had barely hit the one year mark and they were already distant and on the brink of divorce. I don’t know (and at the time, didn’t really care) how true the story was. That was what she told me and I went with it.

When she was working, my not-so-random trips to her work continued. I started showing up later and later; that way, less people would see me which meant less people would start talking, and also it was because I got to walk her to her car after she closed up shop. One time, we almost got to her car when we realized we were holding hands, walking through an empty mall. We just looked down at our hands, smiled at each other, then just had that “fuck it” look on our faces and shared a passionate kiss. All the spark of our old relationship was back, and then some.

Our chats on AOL became a LOT dirtier, and essentially became cybersex. I would say things like wanting to glide my hand down her stomach and circling her clit with my fingers, and she’d respond with how wide she’d spread her legs for me. Our conversations had all the cheesiness of a dollar-store romance novel, but it was turning us both on. But one time, she had said something along the lines of how badly she wished she were fucking me, and i said all she needed to do was give me her address. I actually wasn’t serious, but apparently she thought I was. She said something along the lines of “Look, this is fun and all, but we’re just roleplaying here.” She wanted to make it abundantly clear that she had no intentions of actually cheating on her husband, and that our cybersex sessions were just a way to get something that she was missing in her life. The first thing I thought of was how many times we had spent making out at her car at the mall, but I figured bringing that up would only piss her off. So we agreed that I wouldn’t bring up the idea of going to her house any more. Since I didn’t know how she’d react if I showed up to her work again, I decided to cut out my trips to the mall for the time being as well.

But the cybersex continued and stayed as hot as ever. This went on for several weeks, maybe a couple of months. We probably chatted about 4-5 times a week. Once again, she had made a comment about wishing I was there actually doing to her what I was saying I was doing. And I had said “I can’t. I don’t have your address.”. I knew it was risky given what happened last time, but I figured I’d try it anyway. Her response? “123 Main st. Big yellow house.”

“Don’t tell me that unless you really want me to come by”. I fully expected her to back off, but to my surprise, she was actually quite blunt about it. “why did you think I gave you my address?”. So I tell her “OK, I’m on my way”. I was only semi bluffing, and expected her to call my bluff at any time. No response. A minute or so later, I said “So call me if you change your mind.” She said “OK”. Then she logged out.

Ok, so what do I do? Does she really want this? Is this address even valid, or am I going to drive to some empty lot or something? This has got to be a joke, right? I wait a couple of minutes. Nothing. So I grab my cell phone and start driving to her house. The entire time, I’m fully expecting to get a phone call calling it off, or to find out that it’s a fake address, or that this is some kind of goof. Sure enough, 123 main st. was a big yellow house, and her car was the only car in the driveway.

I sit in the car for a couple of minutes, gathering the courage to actually walk up to the door. I get to the door, heart racing about a billion beats per minute. I ring the doorbell and she answers it. We’re both standing in her doorway, with this dumbfounded look on our faces because neither one of us called the other to call it off. We’ve both got a very obivous “Ok, so what happens now?” look on our faces, and neither one of us knows what to say. She invites me in and starts awkwardly giving me a tour of the place. We’re both speaking in very short sentences with obvious awkward pauses between them. Neither of us are 100% sure what to say or do. Eventually, we make our way over to the couch where we proceed to sit in awkward silence.

“Aw, screw it.”

I will never, ever forget those words. Those are the words she said right before reaching for me and giving me the most passionate kiss I have ever had in my life. She straddles me and our hands are all over each other. Despite this, I’m still not 100% certain she wants to go through with it until she reaches back to pull her shirt over her head, leaving herself covered only by a lace bra that is barely containing her tits. Her shirt barely has time to hit the couch or the floor or wherever she flung it before I have her bra unclasped and fling that away too. I take one of her nipples in my mouth which was always a big turn on for her, and we both quickly lose the ability to have rational thought. She pulls my head in and presses it against her boob as hard as she can, signaling to me she wants me to suck harder. I oblige.

Eventually, we end up in missionary with me on top of her. At some point, she had unzipped my pants and pulled my rock hard cock out, and she was in nothing but her underwear, as we were slowly and passionately grinding each other. She nudges her underwear to one side, and my cock easily slides right in. At no point did we break our rhythm. A couple of times, we stop kissing to catch our breath, but this only causes us to lock eyes and pick up the pace. Eventually, she locks her arms and legs around me as much as she could. She doesn’t make a peep but it’s pretty obvious she’s in an intense orgasm as her hips were no longer moving but her pussy was repeatedly contracting and milking my cock for all it was worth. That was all it took; I came a few seconds later.

We collapse on each other. During our conversations, we always made fun of people who would say “was it good for you?” after sex, and she always believed that if it was good, you don’t have to ask. I guess I’m not that good at sarcasm, because after we caught our breath, I asked in what I thought was an obvious sarcastic tone “So was it good for you?”. She responds with “couldn’t you tell when I came that hard?”. I think it took her a second to get the joke because she paused then started laughing.

Her life took a bit of an odd roller-coaster ride after that. Our cyber-sex talks continued for about 3 weeks and we got together a couple more times after that. She would soon cut off contact with not only me but just about everybody else after announcing she was getting a divorce. I don’t know if our affair played any role in her divorce, but I would eventually find out that her husband would be the one filing for divorce after finding out that she had also had an affair with one of his employees. I don’t know if she was sleeping with him at the same time as me, if the affair was before we reconnected, or after we stopped sleeping together. But after this, we all quietly went our separate ways.

Source: reddit.com/r/gonewildstories/comments/cyqi50/an_affair_with_my_high_school_sweetheart_mf_long