I don’t know anything about virtual affairs.
Sure, I’ve fingered myself over FaceTime to let my affair partner watch me orgasm, but we’ve only done it a couple of times. I’m just not into it because I’d rather have the sex. I can’t imagine getting into it, so it’s an area I’ve stayed away from discussing because it’s not my thing.
Michael slipped into my DMs not long ago after I replied to a comment on a Tweet. I’m pretty much game for any discussion in the comments or DM because I never know where it will go. As usual, after the polite talk, he started hitting on me; I demurred, as I do, because, as it turns out, I’m not the horny sex fiend people imagine I am. Nevertheless, I kept chatting because Michael was interesting.
Michael was interesting because he’s never cheated in the flesh. So after realizing I wasn’t going to be his next virtual conquest, we settled into discussing his lifestyle. Intrigued by it, I had many questions, so I asked him to do this interview series so he could explain it to us himself. Here’s how it’s gone so far —
Teresa (TJC) — Michael, before we get into the nitty-gritty of online affairing, can you tell us something about yourself without going into too many details?
Michael (MS) — Hi Teresa, I’m in my (very) late thirties, and live with my wife in the UK, up North. I’m a teacher by day, and a struggling writer by night — although I hope one day that writing will become a full-time job! I’ve been lucky enough to have a very good education, which although required for my day job, hasn’t really informed my writing. I’ve never cheated in person, but it’s never been far from my thoughts; just when I started to think about turning fantasy and online shenanigans into reality, lockdown hit in the UK so I was restricted to online interactions.
TJC — What was going on that caused you to start looking for a virtual affair partner? Was it something in your home life or relationship with your partner, or was it something else?
MS — I don’t think I was actually looking for anything online, it just sort of started to happen. I suppose I could fall into a thousand cliches; I was under pressure at work, I had a small family, and we were just tired all the time so had less time for each other. I initially started messing around on a well known erotic chat site (Literotica), but even then I wasn’t looking for anything serious, just fun with words. I was bored, stressed, feeling undervalued and almost invisible at home — playing around online generated a bit of attention. I found that other users responded well to me, and I made a few ‘regular’ contacts who I’d talk to online quite frequently. Not always overtly sexual; sometimes it was roleplay, sometimes it was just idle chit chat, sometimes something a bit more intense. I found reassurance in the discovery that many people were in the same situation as me.
TJC — Tell us about the first time you sat down at your computer looking for an online sexual partner. How did you feel — what emotions did you experience? How did you search for one, and how did that go?
MS — I don’t know that there was a first time where it was a conscious decision that that was what I was looking for. I was looking for distraction, for entertainment, perhaps for validation. What I found was an online world of like-minded people, and whilst it was only chatting, it didn’t feel like I was doing anything wrong. So I suppose at the time, it felt good, I felt seen, and that was all positive. Initially, I didn’t feel any guilt at all. Literotica wasn’t a great place to look though as the male:female ratio wasn’t great, so it could be hard to get a chat started as females tend to get absolutely bombarded with messages, many of which were awful. So it was hard work to find someone to chat to.
TJC — Tell us about your first virtual affair partner. How quickly did it take you to find her? Where did you meet her? What was your first impression? What was her story?
MS — I remember my first virtual affair partner very clearly, although it was a few years ago now. She was also from the UK, also married, and was also feeling invisible in her relationship. We got chatting through a chat site and hit it off from the start. It really didn’t take long to progress — about 15 minutes. I was already playing with myself, which I had told her. I asked her if she wanted to watch, and she said yes. So I sent her a link and suddenly there I was, on her screen, and there she was on mine. No real names, no faces. We had our mics on but no one spoke. All I could hear was her breathing. I typed something in the chat, and heard her giggle.
That broke the ice, so I spoke, and the conversation started. Before long she pulled down her top and took off her bra; I pulled my shorts down and let her watch me masturbate. We both came really quickly — the whole thing lasted less than 5 minutes which in hindsight was a bit embarrassing but didn’t seem to matter too much at the time. Afterwards I was a mess (literally). It was so unbelievably hot, I LOVED being watched — but at the same time I was also hit with a wave of guilt, especially as I watched the screen go blank as my cum rolled off my stomach and onto the floor — something we got to calling a cumdown. But, I knew straight away that this was not going to be a one off.
Coming up in Part 2
A cumdown indeed! Michael will tell us about his other affair partners the connections he’s established with them offsite but still online in the next installment. Then, in the final installment, we’ll talk about how you can start an online affair!
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