Relationships

Men Confess The Dirtiest Sext They Ever Sent & How It Was Received

by Hannah Orenstein

I once had a friend show me X-rated sonnets a guy kept sending her. Instead of texting her photos of his junk or sending dirty sexts, he actually wrote 14-line poems in strict iambic pentameter that described his boner in Shakespearean terms. It was impressively nerdy and honestly the most creative sext I've ever seen.

If poetry isn't your thing, though, that's fine. Instead, take inspiration from real sexts that eight men have sent to their girlfriends, Tinder matches, and, in one cringeworthy case, his mom. (It was an accident!)

I'm going to let the men speak for themselves. Prepare yourself for what you're about to read — it's intense.

This man sent a nude and got a baker's dozen of sexts back... that his mom happened to see.

My mom was driving my Mercedes because I was too tired to drive. You know that software where your car plays incoming messages on your phone out loud? This girl who hit me up on Tinder texted, 'Are you going to come over and let me suck your d*ck?'
My mom heard this and went, 'What's that?'
I was like, 'Nothing!'
I was just cheesing in the passenger seat, and I sent the girl a picture of my d*ck. I received a dozen pictures of her *sshole, vagina, everything, even a video. The video played out in front of my mom on the car dash.
My mom saw the video, and I was like, 'OK.'
That's when I knew it was time to buy my mom a new minivan. I guess she wants grandkids, so why not give her the car?

— Casper, 23

This man got specific about what he wanted — and she responded with the same.

I said, 'I can't wait to breathe heavily and moistly right up against you as I kiss your inner thighs and grab your tits.' She said, 'I can't wait to play with you in my fingers, licking the very tip of you.'
To be honest, though, in my experience, I sometimes worry about initiating sexting if it's not a very serious relationship. I worry that I come off as creepy.

— Sean, 25

This man sent a video of himself finishing that the woman never forgot.

Was in a pretty intense back and forth sexting session with a gal, mostly a contest of who could escalate the other more. Ended up sending a video of me finishing and then licking my fingers and smiling for her on camera. Her response was something along the lines of 'holy h*ll that was hot.' Still gets brought up from time to time when I bump into her. So must've made an impression

— /u/jololothrowaway

This man texted his date about his boner, and she invited him over.

I met this girl from Tinder Social at a party I was hosting, and we kissed just briefly, and she left. We were texting afterward, and she explicitly said that we weren't going to have sex (I did not ask), and I sent her what I would consider a sext, but it was more like a last-ditch effort: 'My boner for you is infinity.' Surprisingly, she responded very well to it, because she invited me over in the next text.

— Honan, 25

This man sent a graphic GIF of himself, and the recipient wound up showing it to her friends.

I once sent a GIF of the 30 seconds when my d*ck came all over while i was f*cking myself with a really big dildo. We had a falling out the next week, and she ended up showing it to a bunch of friends in common to try and embarrass me. No regrets.

— James, 33

This man sends X-rated greetings on Tinder, but doesn't get responses.

Once, I sent this as my opening line on Tinder to some girls: 'I'm the kind of guy that will place my thumb in your *sshole as I f*ck you from behind... too soon?' They never responded.

— Ramon, 25

This man was inspired by Hollywood.

'Hey maybe before we go see the avengers, we could go to my place for a little 'Hulk Smash' of our own.'
Best part was her friend was looking at her phone at the time.

/u/chew_it_punchy

This man's sext was foiled when he accidentally sent it to his mom.

Here is the exact response I received from the dirtiest text I've ever composed and pushed 'send'.
'I always knew you were my worst son.'
Yep, accidentally sent to mom.

/u/Mysecretpassphrase

Lesson learned: Always check to see if you're texting the right person.

Quotes have been edited and condensed for clarity.

Check out the entire Gen Why series and other videos on Facebook and the Bustle app across Apple TV, Roku, and Amazon Fire TV.

Check out the “Best of Elite Daily” stream in the Bustle App for more stories just like this!