The Unexpected Lesson I Learned After Having Cybersex For The First Time

Photographed by Rockie Nolan.
Sexting was never my thing, and I sure as hell never thought I would even consider cybersex. I knew myself — or at least, I thought I did. I’ll get too emotionally attached, I’d think. My self-esteem can’t handle the potential rejection — I’ll have no idea what I’m doing. It just seemed too scary. That was until I met Lucas*. We were at a bar, and he was semi-cute, but very charming and funny. By the end of the night, he had asked to take me out as soon as possible, and we had kissed and exchanged numbers. Before I even got home that night, he started texting me, and within a few days, he tried to switch our digital conversations from sweet to sexual: “When we go to the movies, can you wear a skirt? I want you to sit on my lap in the theater and see what happens.” I was a little shocked, but definitely curious. Still, I told him to slow things down — it was a bit too soon for sexting, in my mind. We continued texting, touching base almost every single day to get to know each other. After a few weeks, he once again steered our conversation toward the X-rated (dick pics included). He told me he’d break me of my nice-girl ways, and I’d do things with him that I’d never do with anyone else. I was excited and nervous at the same time — I kept thinking, How far is this guy going to push things? Am I going to end up having a threesome in a bar somewhere? Throughout all of this, while he was constantly pushing to talk to me over text, he never made the commitment to see me in person, and he blew me off regularly. Should I have ended it and gone running when he pushed it to that point after I told him to slow down? Yes. Didn’t he seem like a creep who was out to see how far he could push me? Yes. Trust me, I saw the red flags, but I loved hearing from Lucas. He made me feel sexy, turned on, and surprisingly comfortable. Then, one day, he suggested we FaceTime. I freaked out; it was the middle of the day, and we still hadn’t met face-to-face since that first night at the bar. Plus, I had never tried cybersex or even thought much about it before. But again, something about his X-rated requests intrigued me. He was so sexy, I was pretty sure it didn’t matter if we were in the same room or a thousand miles apart — this guy could make me orgasm.

He was so sexy, I was pretty sure it didn’t matter if we were in the same room or a thousand miles apart — this guy could make me orgasm.

The first time we got on camera, it was awkward, much like it is the first time you have sex with someone new. I stayed mostly clothed, but I still felt unsure of what I should say (if anything), and I was definitely uncomfortable with him seeing me in such an intimate moment in broad daylight before we had even fooled around IRL, so I followed his lead. I was shocked by the things he said, and yet, it was totally hot. He told me how to touch myself and what to imagine him doing to me as I got closer and closer to the edge. The crazy thing is, even though we weren’t physically together, I felt close to him after this encounter — like I was giving him something extremely special. I was honest and open about what I wanted in a way I had never been with anyone else. After the first time, we started having cybersex frequently, both of us getting more comfortable and pushing the limits of fantasy to things I had never fathomed. I was loving it and craving it. But at the same time, I was getting jealous and attached, and couldn’t help but feel used; we still weren’t hanging out offline. It felt confusing, like I was in a weird dating/non-dating limbo with someone I wasn’t even physically getting to see. Not one to wait for anyone, I still went on dates, but I wouldn’t do more than kiss other guys, because it felt dishonest. After two (agonizing) months, Lucas and I finally got together. I'll spare the details, but it was by far one of the most passionate, comfortable dates I’ve ever had. It felt like we were two people who’d been dating for months — beyond the physical stuff, we were comfortable just sitting and talking. It weirded him out how non-weird it felt. “We’ve only met the one night,” he said. “It shouldn’t feel like I’m out with my girlfriend.” I agreed, but at the same time, we’d been talking and “seeing” each other for months. Because of all of the cybersex we’d been having, I was already comfortable with him. I’d seen him at some of his most vulnerable moments and knew what he was going to like. And I’d taken what we were doing seriously from day one. Lucas, on the other hand, was able to distance himself emotionally from me until we actually met face-to-face — suddenly, I was very real to him, and he was confused about his feelings. It took us finally seeing each other in person for him to realize he really liked me, and that he might want to slow things down. Despite Lucas’ emotional distance, it was clear that those two months of hot cybersex gave us a level of openness and intimacy around sex that some of my friends have never had, even with their spouses. It was incredible how easy it was to turn our virtual connection into real-life sexual chemistry.

It was clear that those two months of hot cybersex gave us a level of openness and intimacy around sex that some of my friends have never had, even with their spouses.

However, with the fun, connectedness, and comfort that came with cybersex and beyond, there were a few situation-specific negative outcomes that caused more harm that those on-screen encounters were worth. We hadn’t discussed our feelings before jumping into cybersex — which is something I would have definitely done had we been having sex IRL — and I grew attached to something that wasn’t real. It soon became clear that Lucas wasn’t taking our relationship as seriously as I was, and I didn’t know how to protect myself emotionally in such new sexual territory. The moment I hit “answer” on my iPhone, I put myself in an extremely vulnerable position. I may have been safe from sexually transmitted infections and physical danger, but I wasn’t taking into account how this would affect me emotionally. I’m not the type of person who enjoys casual sex (not that there is anything wrong with casual sex — it’s just not for me), so I wasn’t being fully honest with myself about my desires, and I became increasingly insecure. I was loving getting to know Lucas beyond our cybersex connection — his politics, his family stories, his life goals — and I wasn’t prepared for how I’d feel if that interest wasn’t reciprocated after our intimate FaceTime sessions. I honestly just didn’t expect to feel so close to someone I hadn’t slept with in “real” life. Ultimately, the whole experience was confusing as hell and a waste of my time and emotions. After about five months, I realized he was still exploring his options, going out with other women, and just using me when he couldn’t find someone to take him home. Despite claiming he wanted to “date” me, Lucas never followed through with spending more time together and made it clear that he didn’t want anything more than an occasional hook up. And despite all of the red flags I noticed early on, that realization was tough after growing so close over FaceTime. Sure, there were benefits to the new kind of intimacy I discovered through cybersex — I was able to explore myself sexually in a way I had never even considered — but I’ve realized that I’d personally prefer to hold off on cybersex until I know I’m in a healthy, committed relationship. Of course, that’s just what works for me, and I know that plenty of people are able to enjoy how passionate, fun, and bonding cybersex can be without emotional commitment. It just took a little trial and error on my part to figure out where I fell on that spectrum. In the end, my first experience with cybersex wasn’t a complete waste of time — I’d definitely try it again in different circumstances. And at the very least, now I know never to say “never” when it comes to sex. *Lucas’ name has been changed to protect his identity.

The gap between what we learned in sex ed and what we're learning through sexual experience is big — way too big. So we're helping to connect those dots by talking about the realities of sex, from how it's done to how to make sure it's consensual, safe, healthy, and pleasurable all at once. Check out more here.

More from Sex & Relationships

R29 Original Series