Sex Diary: Cyber Sex Gets Real

Welcome to the Frisky “Sex Diary,” in which an anonymous person shares the details of her sex life over the course of a few days. Sometimes these entries are filled with revealing romps, while other times there is nary a naked moment in sight. Some of these diarists are frequent contributors. Want to share a page from your sex diary? Email [email protected] All entries will be anonymous.Diarist: A 22-year-old college grad, still working in retail because “I picked a Liberal Arts major.”

Sunday Night: I got dumped recently. He just stopped calling and refused to answer my calls, texts, or messages. So, fresh from a week of moaning to my BFFs and reciting “you deserve better than that cowardly piece of trash” to myself on an hourly basis, I hit up my favorite free online dating site. I’m not looking for anything serious, or even anything casual. I’m seeking the ego boost of a couple “Hey, you’re cute, want to chat?” emails.

I get it.

Emailing quickly progresses to IM.

The guy is hot. Like, out-of-my-league hot. If I saw him at a bar, I would never think I had a shot with someone that tall, blond, and well-built, but online he approaches me. We chat amiably for a while. Then he asks if I wanted to have a “discussion” about sex.

Discussion. Right. He asks for pictures, which I refuse because, hey, you never know where that stuff’s going to end up, right?

I’ve never had cyber sex before. I’ve had suggestive conversations about likes and dislikes, and I’ve done (more than) my share of flirting, but I’ve never really gone “all the way.” At first I’m kind of awkward, blushing while I type and thinking, “Oh my God, I can’t believe I just said that” every time I hit “send.” After about 10 minutes, though, I kind of get into it.

It’s completely anonymous. I say dirtier stuff to this Internet Hottie than I’ve ever said to any guy in person. And oh my God, does it get me hot and bothered.

He wants to hook up this week. I suggest Wednesday, because I’ve got Thursday off work, but we’ll see if I even hear from him again.

Monday Night:

Internet Hottie proves to be a fantastic distraction from my recent breakup. Of course, this also means I spend most of the day kind of turned on. I rush home from work and log onto IM practically the second I walk through the door, eager to see if he’s pulled the disappearing act yet.

The fact that I’m so anxious to talk to him again is probably a bad sign. I know this is purely a sex thing, and my mind’s OK with that … but I hope my emotional side can handle it. It would probably be smart to sever ties with this guy, never meet in person, but … I can’t help it. I’m horny, and he’s really hot.

We chat a bit. He asks if he can come over. I give him my usual line about how he could be a serial killer and I need to meet him in a public place first. He brushes it off, and then starts asking for pictures again.

Here’s the crazy thing: I do it. And it isn’t really a spur-of-the-moment thing, either … it requires getting up, taking off my shirt — I kept my bra on — taking photos, uploading them, cropping out my face and sending.

Oh. My. God.

I am from a small town in the Midwest. My first “real” relationship just ended. I’m not very sexually experienced, though I’m not a virgin by any means. And my body? Not the greatest. What I am is smart. I know better than this. But I do it anyway and … it’s kind of a rush.

I feel … powerful, knowing that looking at me and talking to me is getting him off. In exchange for the picture, he turns on his webcam. I guess I shouldn’t be surprised that a guy willing to masturbate in front of someone via the internet would be well-endowed, but I admit I am kind of impressed anyway. I’ve never considered male genitalia particularly attractive, and I’ve never looked at porn to get myself going, but I’m reconsidering now.

I get out my vibe. Things progress. It’s 12:30 when we finish, and he logs off immediately. I go to bed, snuggling into my newly-inflated self-confidence.

Tuesday Night:

I log on immediately after I get home from work at 9:30, but Internet Hottie isn’t online. Shrugging it off (or trying to), I go about my business. I even get out my vibrator and, err, go about that business too. While thinking about Internet Hottie. Mmm.

He pops up at about 11:20, just as I’m contemplating going to bed. We joke a bit about having fallen into a routine (Monday night he’d remarked that he gets horny at the same time every night, around 11), and about him being late. Then he requests that I help him get off since I’ve already taken care of things on my end. I oblige. He begs for pictures, again, but I refuse … especially since we’re set to meet Wednesday evening.

I’m kind of nervous about that. OK, who am I kidding; I’m WAY nervous about it. I’ve had one-night hookups before, but they’ve always just kind of happened organically at parties. It’s different when you plan it out and go into it with your eyes wide open. I tell him we can meet someplace close to my apartment for a drink, and if we hit it off he can come over … but if not, one or both of us could pull a “you know, I just remembered I have to get up really early tomorrow …” and have an out.


I’m sitting at work thinking about sex. This is not unusual for me, but it is unusual for me to be pursuing “just sex” so single-mindedly.

There are the usual worries, of course … he’ll see me and not find me attractive in person; I’ll see him and chicken out; he’ll have a weird and un-sexy voice; he’ll give me the clap; it’ll be really bad sex in person; I’ll somehow become emotionally attached to him and wind up heartbroken because an internet hook-up didn’t call me the next day.

Sad as it is, the last one seems most likely. I like to think that going into this with no illusions, I’ll be able to restrain my over-eager emotions, but you never know. Oxytocin’s powerful stuff.

Later That Night:

He doesn’t text me until nearly 10:00. I almost chicken out. I’m stupid and give him my address and he comes over. He’s been at a friend’s house since he got off work, goofing off, so he shows up in sweat pants and a T-shirt. Sloppy, yet hot — I’m a sucker for biceps. A tight T-shirt gets me every time if the guy’s remotely built.

He’s as cute in person as he is online. Tall, but not too tall, blond hair, blue eyes, glasses … the kind of guy who, had I seen him at a bar, I would have been too intimidated to flirt with beyond a long glance and maybe a smile. It’s surprisingly easy to talk to him. He seems intelligent, funny, and with a streak of dorkiness that puts me at ease fairly quickly. We sit on my couch for about an hour and a half just talking before anything happens.

He kisses me. I’ve never been kissed like that before: long and slow, like the intent isn’t so much to “kiss” as it is to just be touching me. Kissing leads to a back massage, which leads to the bedroom. I’ve only received oral once before, and I could tell the guy wasn’t very into it so it wasn’t really enjoyable for me. Internet Hottie, however, is very into it. But he isn’t offended or upset when I tell him I can’t orgasm without a vibrator—he simply asks if he could use it on me.

Um, yes.

The best part about that is that he seems to truly get off watching me get off … or at least, he’s really good at pretending. I can’t even remember all the compliments he tosses my way all night. Lines? Undoubtedly. But they’re still appreciated. My eyes, my hair, my skin—he’s obsessed with how soft my hands are—all receive praise numerous times.

Then it’s his turn. I really want to give him head, but I also want him inside me, and I decide I’d waited long enough. Condom on, girl on top—delightful. I really want him to pound into me, too, so I’m disappointed when it’s uncomfortable. He’s bigger than I’m used to, or maybe just more enthusiastic. Even holding back, though, it’s good.

The best part, though, is that it isn’t awkward afterward. We talk for a few minutes, he gets up to bring me a glass of water and turns my kitchen light off, then he falls asleep (and snores—only downside) for about two hours before he has to get up and leave for work. He kisses me before he leaves.

I know this is a blatant sex-only hookup. I’m trying so hard not to hope for a phone call or text tomorrow, or any kind of more-than-sex overture. But God, I want him again.