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I’m not much of a sexter. I don’t trust most people with screen-grabbable pictures of my penis or evidence of me attempting to talk dirty. (And when I say I don’t trust most people, this includes most people I have already actually had sex with. I am a broken human being.)
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But I have done it. The last time I gave sexting a shot was when I was drunk one night, and Allison, the woman I was dating, was out of town for a few weeks. I missed her. And her vagina. So I started firing out some sexts, telling her what I wanted to do with/to her, etc. A lot of it was composed of graphic detail re: what oral sex methods I would use on her if she was in my bed at that moment.
I found it odd that I didn’t get any messages in return, and after 15 or so minutes, I checked my phone to find that I had not been sexting Allison, the woman I was dating.
I had been sexting my Aunt Allison. Luckily, we were able to have a good laugh over it later. But it did kind of put a damper on any enthusiasm I had for sexting.
Here at WomensHealthMag.com, we got to wondering what other peoples’ sexts look like. So we reached out to a bunch of people to get them to anonymously share some of their best, worst, and weirdest sexting stories.
1. The Surprise Grandpa
"I’ve only sent out a cock shot one time in my life, and that was after she promised to reciprocate. I sent the sexy, then realized there was a picture of my grandfather in the background. So I’m feeling weird about it. Here’s how she responded."
2. The Tinder Turn-Up
"I’ve had a few pretty crazy experiences with girls I’ve met on Tinder. Actually, girls I haven’t yet met who I’ve matched with on Tinder. It’s weird that you can get this, um, intimate with someone you haven’t even met. But maybe that’s why they’re willing to be so forward—they don’t actually know you! This one happened with a girl I’d been texting with for, like, 24 hours or so. We were having a normal conversation, and then she said, 'You know what I want?' This is what followed."
3. The Bait and Switch
"My current girlfriend was trying to get me to sext for a few months, but I was uncomfortable with it at first—so I sent her a picture of a dick that wasn’t mine. And I mean clearly wasn’t mine since it was an absurdly large black dick. Eventually, I got a new phone that could handle SnapChat, and we started really sexting. But it’s nothing too special."
4. The Least Sexy Word Ever
"I was home for the holidays and out with some of my high school friends when I suddenly received a text from a guy that I had hooked up with ages ago saying, 'Hey, was just thinking about you, and I miss your body.' Which was super awkward, but he was really good looking, so I was like, 'Okay, let's see where this goes.' So basically, he just goes right into the whole, 'What are you wearing? Imagine me taking that off of you, etc. etc.' Typical sexting stuff. I was really preoccupied with my friends, so all of my responses were literally, 'You want to do that to me? Okay.' Literally the most unsexy things I could say. I guess that was really getting him off, and it continued for about 30 minutes, when all of a sudden he says, 'I want to ask you to do something to me, but I'm scared you'll think it's weird.' That's when I got intrigued. I really turned on the charm to try and get what he wanted out of him. Eventually, after really not trying hard at all, he says it: 'I want you to tell me that you're going to lick my butthole.' I. lost. it. I think the word butthole is LITERALLY the least sexy word you could ever say. And then, to make matters worse, while my girlfriends and I were giggling about him saying butthole, he sent me an actual picture of his creepy, hairless, lit by flash, butthole. Needless to say, we have not spoken since.”
5. The Pizza Solution
"One night when I had been out of town for a while and was missing my girlfriend, I tried to get her to sext with me. She wasn’t in the mood or whatever and just kept telling me she wanted pizza. So I ordered her a pizza. I wonder what would’ve happened if I’d gotten her cheesy bread, too."
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6. The Busy Work
"I met a guy on a dating site, and we had gone out a couple of times. We had made out and done some feeling around, but nothing beyond that. One day, around lunch time, he texted me and asked how my day was going. I responded with, 'Oh, it’s fine, just a typical Wednesday,' or something like that. Then I asked him how his day was going. He responded that it would be going much better if I was there at work with him. He followed this with a video of himself masturbating in his office. I broke things off with him after that. It was too f--king weird."
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7. The Nope
"In my mid to late twenties, I dated a male coworker who was 13 years older and was recently divorced with two kids. The chemistry was palpable, and the sex was amazing. The between-sex communication, however, not so much. We saw each other once a week if we were lucky, due to the kids, so I figured a healthy spicy texting relationship would bridge the gap. He was, apparently, not ready for this. Finally, after all my attempts to get him out of his sexting comfort zone, I just started laying it on thick."
"And that, my friend, is as crazy as it ever got. I never tried again. It didn't matter, ultimately. In person, everything was perfect. But maybe you both have to be a little imaginative/freaky for a mutually satisfying digital sex life."
8. The Bad Morning Meme
"I worked with a guy who seemed nice but a little bit strange, though attractive. He was only in my office every once in a while, but when he was, he was very nice to me. One time, he asked me if I wanted to go to a happy hour with him. The next week, we did. It was pretty normal, and we kissed a little bit. A few days later, I woke up in the morning to a picture of a ball gag and a set of handcuffs, followed by one of those creepy cat meme pictures that said, 'Soon. Very soon.' I texted back that I hadn’t even had a cup of coffee yet, and we haven’t spoken since."
