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Safe Sexting

Exploring the awkward world of doing it digitally


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It was a little after 1 a.m., and I had just arrived home and was combing the kitchen for a post-bar, pre-bedtime snack. As I foraged through my cabinets for something edible, I heard my text message alert go off.

Oh, it's him.

I figured he was somewhere in the city where he now lives, watching a band we both liked, or maybe some new band he thought I'd like. Music was all we really texted about anymore, and our exchanges these days were infrequent and casual, but always cordial. After more than 10 years of friendship — and sometimes more than friendship — that's what we usually talked about.

Well, that wasn't entirely true. The last time I'd seen him, about a year ago, we'd had a pretty passionate night — lots of sex, records on the turntable and long conversations. The kinds of conversations you have with a former flame when you both ponder why it didn't work, because in that moment, it just seems so right. But these are the kinds of conversations you can have when you know it's still not going to work, so your chatter is relaxed, honest, and ultimately, without consequence.

Why doesn't it ever work? Careers, geography, other significant others, life ... whatever the culprit, I'd reached a point in my head and my heart that was dangling dangerously between realism and cynicism. My philosophy on love was simple: If someone wanted to be with you, they'd make the effort to be with you. The rest is just bullshit.

I shoved some slightly stale Pirate's Booty in my mouth as I opened his text, which was flirty from the beginning. The tone got more and more heated. Intrigued, I followed suit.

"I want you," he wrote. "Like, all if you. Now. Did I just write that? So awkward."

I slowly put the Pirate's Booty down. Did he really just write that?

"... all *of* you. I suck at sexting," he corrected.

Wait, are we sexting now? Can people above age 30 sext? It seemed so juvenile.

Before I had a chance to think of a witty response, a photo came through. A photo of a penis.

I dropped my phone into the sink. I quickly fished it out of a (thankfully) empty coffee mug. Was that his penis? Surely not. That's something frat boys do, not mature, intelligent men in their early 40s, right? Maybe this was some kind of a joke. Yes, this had to be a stunt penis, like that photo of a penis in a high-heeled shoe that circulated among my friends last year. (Seriously, Google "shoe dick." You're welcome.)

I enlarged the photo and attempted to discern if this was actually his penis. It had been nearly a year since I'd seen it, and it was hard to tell. I felt like Hannah on Girls when she gets the bizarre fur-penis pic from Adam and pretends to be horrified but is actually flattered.

"Soooo. You mean business." I wrote.

"That was weird. Sorry." He fired back.

The awkward conversation that followed revealed that this particular penis selfie was the first he'd sent — lucky me! But since I try to be open-minded, I decided to go with it. I mean, we live in a #nofilter world nowadays, right?

"I have seen it, and I would like to see it again." I wrote. Was that sexting? Did that sound sexy? It sounded kind of matter-of-fact. I wasn't sure how far down the rabbit hole I wanted to travel.

For a few minutes, we filled in all the gaps of what-have-you-done-since-last-summer before the convo took another tawdry turn.

"I was going for reciprocal effort," He pleaded. "But all I got was giggles. I should have known!"

I started to feel a little bad. Not bad enough to send him a dirty selfie, but since he threw me a boner, I thought I'd throw him a bone and, simultaneously, pop my sexting cherry.

What followed is certainly unsuitable for print, and far too embarrassing, but I think it was enough to earn my Girl Scout badge in Sexting 101 — even if he did point out that I could have used more adjectives. Noted.

One thing sexting and sex have in common is the morning after. Instead of the walk of shame, you have the text of shame. Assuming that he might be feeling a little foolish about the previous night's exchange — the proof of the slightly sordid affair was recorded on both of our devices — I decided to defuse any potential awkwardness with humor.

"Is it weird that we're having a hot dog party at work today?" I wrote, surrounded by my colleagues in the company parking lot for a cookout the following afternoon. For added effect, I sent a picture of two giant hot dogs, doused in condiments.

"Those are some enormous wieners." He responded. Things were back to normal with us, post-cellular-coital.

I have to say, I don't get what all of this sexting is about. While it's certainly safe sex — I haven't heard of anyone catching chlamydia through his or her smartphone — it's kind of pointless, right? And, if you're like Hannah and you send a nudie pic back (which, I'd like to stress, I did not), some dude has a nudie pic of you on his phone. And he's definitely going to show that to his friends, whether he's 21 or 41.

So, ladies, if you're going to indulge, practice safe sext. Or send a photo of someone else's boobs. He probably won't know the difference, anyway.

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