20 People on Sexting

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Photo: Dennis Galante/Corbis

Whether you’re single, dating, married, cheating, or masturbating, you’ve probably experienced the perils of sexting. It’s a tricky business: What’s too much too soon? What if someone sees your phone? And can emojis ever be sexy?

From an “all balls” snapshot to a virtual affair that ended a marriage, here are twenty sexting stories that will make you want to charge, lock, or lose your iPhone.

“He’s married and it’s wrong.”
I met this Dutch guy at a Mexican hostel six years ago, on my 24th birthday weekend. We got drunk and had sex on the roof as the sun was rising. It was a great holiday fling. I found him really impressive; he spoke lots of languages and had a really big dick. We never saw each other again, but we’ve been sexting for five years — even though he got married in 2010. He always initiates. We write sexy random things during the day, but also have hardcore IM sex (via Gchat) sometimes. I really like doing it when I’m in a hotel room — I travel a lot. I know he’s married and it’s wrong, but I’m single and this brings great pleasure into my life. Sometimes he goes too far. When he says he wants to shove his cock down my throat … I don’t like that one. For one, it’s too big and also it’s too aggressive. I should probably just end this entire thing.

“I take titty pictures.”
I work at a restaurant on most nights, so I see couples making out and being all sexy. Around 10 p.m., I get horny and start to miss my boyfriend. Then I go into the bathroom and take titty pictures to send to him. As the night progresses, sometimes the pictures get raunchier. Lately I’m into nudey pics with a female co-worker. Like, shots of me licking her nipple and stuff. Hey, the hospitality world is risqué.

“It revealed that I actually liked her.”
I recently texted a woman, who I had started having sex with, that I thought she was beautiful. Apparently that ruined the mood for her. It revealed that I actually liked her, which is not what she wanted from our "relationship." She ended it.

“A Jackson Pollock–esque cum shot.”
A well-known male socialite sends me dick pics all the time. I don’t mind it, because I show all my friends and we die laughing. It’s pure entertainment for me … but I really have no idea what he gets out of it. We barely know each other, and he’s definitely not looking to date, or even fuck. Last week he sent, like, a flip-book of his growing erection. It ended with a Jackson Pollock–esque cum shot. I wrote back, “Wow!” I never have anything good to say, because ultimately I couldn’t care less about this person.

“Epic sexting sessions.”
I met a girl a few years ago who had a serious boyfriend (now fiancé), but for whatever reason she gave me her number. I tried to hook up with her, but she felt too guilty about actually cheating on him. However, we would have epic sexting sessions ... usually during the day at work, since obviously her boyfriend wasn't around. A few times she said she would be so turned on that she'd have to go into the bathroom and take care of business before she could concentrate on work again. Every once in a while she'd hit me up when her boyfriend was out of town and tell me she wanted to get together, but it never got past sexting or phone sex.

“My hard rod … ”
After sleeping with an older man, he sexted, “I want to stick my hard rod into your wet pond!” That was the end of that.

“Accidentally sexting with my best friend.”
I had a long sexting relationship with the same guy for years. I met him in the city one night, nothing happened besides intense flirting. He lived in Houston, so we started Gchatting and texting. I had never sexted before, so when he started initiating, I was a bit put off, but we had such a strong connection that I kind of fell into it. He had an obsession with my legs, which are abnormally long, so I texted him that I wanted to wrap my legs around him. I was in a cab and not really paying attention. The next thing I know there is a pause ... and my best friend (a girl) BBM’s me, "Sounds good!" Apparently I had been accidentally sexting with my best friend because both their names start with M. She was actually at dinner with a bunch of my other friends and they were all reading it out loud. I still haven't lived that down. 

“I left my phone in a restaurant bathroom.”
I was sexting this guy from a restaurant. I went to the bathroom and apparently left my phone next to the sink. It was not locked … so the next thing I know, a woman comes over to my table, asked if this was my phone, and then winks at me and says, “Nice work."

“Selfies showcasing her developing pregnant shape.”
Throughout my wife’s first pregnancy, she endured my constant fawning over her new shape — every luscious curve. She wasn't sure what to make of it at first, but grew to appreciate my perpetual interest her changing body. While carrying the twins, next, she decided to completely go with it.

While I was at work one day, she sent me a text asking if I had a moment, if there were others around me, and if anyone else could see my phone. I wrote back saying that my co-workers were at their desks and that they couldn't. She then proceeded to send me a handful of selfies showcasing her developing pregnant shape, fully nude — three gorgeous pictures which made me smile, giggle, and made my heart skip a beat. I wasn't sure at first if I was seeing my phone correctly.

Over dinner, she explained she knew I loved how she looked when pregnant, and that she felt particularly sexy that day and wanted to share with me. She also added that there was a bonus in knowing what it was doing to me: totally killing my concentration.

“Online lesbian sex.”
I’m a straight female with a serious boyfriend, but I like meeting crazy, slutty women on Craigslist and then Gchatting or BBM’ing sexually until we both come. I’ve been having online lesbian sex since the first AOL chartrooms came out. I’m not gay. I just like it. I’ve never even kissed a woman.

“Sexting has fucked me up.”
I’m 37 and single and have been in an obsessive-compulsive sexting relationship with a married man for over four years. I am consumed by our BBMs, Gchats, and texts. Once a year, we meet in a hotel room in another city and fuck each other’s brains out. It’s never a letdown … it’s mind-blowingly hot. I mean, a year of build-up exploding at once? I can’t get him out of my mind … ever. I don’t date because I know I can come home and sext with him. He gives me all the attention I need. He is always there for me, even though … he is not. I am hooked and it’s sad. With him, I feel like an addict. Sexting has fucked me up.

“Eggplant + doughnut = splash.”
I was in an LDR: Boston to San Fran. The texts were the main source of our communication. He was the sexiest, most passionate guy, and our chemistry was off the charts. He had an amazing sense of humor and was very clever with words, so it all become very fun and enchanting. Also, since he's an artist, he was great at using the emojis to create dirty images. Emojis like: eggplant + doughnut = splash; bananas, cherries, and lots of finger signs into a doughnut.

“Too vulgar.”
This guy sent me a picture of his penis after the first time we had dinner. It was decent-looking, but it really turned me off, and it made me not want to see him again. It was too vulgar. I went silent and he got really insecure. That’s just not my style.

“I was so attracted to him that nothing offended me.”
I had a super-hot fling with the most gorgeous guy I’d ever met. The relationship was purely sexual. A few times a day he would text, “I want to see your tits. Photo, please?” I was so attracted to him that nothing offended me. His favorite was to send a photo of his five fingers and say, “Which one would you put in your ass?” Sometimes it was just one finger and he’d say, “Which hole wants it more?” I am very pro-sexting now!

“Dropped my iPhone in the water.”
I always take dirty pictures of myself in the bathtub to send to my boyfriend when he’s away on business. Last week I was masturbating in the tub, trying to make a video of it for him. Then I dropped my iPhone in the water! I was cracking up, but the phone was destroyed! I knew that would happen eventually … but it was definitely a risk worth taking.

“A picture of his BALLS.”
I started seeing this guy. We had kissed, but I only “pet” him on the outside of the jeans. No nudity. Then he straight up sent me a picture of his BALLS at like two in the afternoon. JUST BALLS. He didn't even send it in Snapchat. And guess what? I’m still dating him.

“Filthy interlaced with emotional.”
My ex-fiancé, who left me at the altar and broke my heart, sends me the filthiest sexts when he’s drunk, but they are interlaced with all this emotional, super-heavy shit, too. Like, “I remember how it felt to be deep in your mouth.” Then a second later, “I made so many mistakes ... can we start over?” One said, “I’ll never love anyone the way I loved you.” Five minutes later, “Must cum in your ass tonight or will die.” I e-mailed him recently and said, “It sounds like you have some stuff to say to me? Do you want to talk?” and he responded with something totally detached like, “Hmm … traveling all summer but maybe in the Fall?” It’s so confusing.

“Completely delusional!” 
I briefly dated a man with bad penis problems. We never addressed it. As soon as he’d go limp, which was every time, he’d just switch to hours of oral on me. I assume he was on Rogaine or antidepressants, maybe cocaine. Who knows. The thing was, he would sext me as if we had the most outrageous sex life! Like, “I’m at work, ROCK HARD, thinking of you.” Or, “let's go upstate and break some fucking beds.” It was completely delusional! Like — hellllo, our sex life sucks? Eventually I ended things with him because the disconnect between his broken dick and his filthy texts were making things really creepy. I kept thinking, What the fuck, dude? WHAT ARE YOU EVEN TALKING ABOUT?

“Sexting broke up my marriage.”
I’ve never cheated on anyone and I didn’t want to cheat on my husband, but I was desperate for some kind of jolt in my life. I met this guy from Argentina while waiting in line for an ATM. He was smoldering hot … the type of man put on this Earth to sexually please women. He asked me out for coffee; I told him no, because I was married. We exchanged numbers. The sexting started before I even reached the corner. “I need to kiss you,” he wrote. “No, sweetie, no ... ” I wrote. And so it went … for many months. I grew more and more detached from my husband. It became an emotional affair. And then — a classic story — husband found the texts on my iPhone. The discovery killed my husband and destroyed any strand of hope we had for our future. When we separated, I tried to see the Argentinian in person. It was awkward. We did end up sleeping together, but it wasn’t what either of us expected. Our romance belonged inside our imaginations, not in reality.

“It can be very sweet.”
I have amazing chemistry with my local bartender; we are both single. We text really adorable things to each other all the time. They’re not vulgar; they’re warm and flirty. I’m thinking about walking in and just kissing him one of these days. I think sexting is the modern-day flirting. It’s not always deviant. It can be very sweet.