How I Learned To Sext

A mutual friend introduced us over WhatsApp.
It was definitely love-at-first-text. He wrote…


His sense of humor, charm, and zest for life won me over immediately.

I live in New York. He lives in London. So most of our relationship had been cultivated via tiny words on tiny screens.

I think WhatsApp is critical to our story because you’ve got read receipts and the double check. You always know what’s been seen and read, which is both comforting and terrifying.

By the time we had met in person in December, hundreds of messages had been exchanged.

I flew to London to see him. It was a magical weekend. Our relationship was instantly passionate and safe. It was something I’d never experienced.

I’ve been in love before.

I’ve even been married and divorced. But in my old relationships, I did a lot to suppress my real feelings. I wasn’t ever really comfortable expressing my true self — not emotionally, and certainly not sexually. Self-expression was limited to what I thought was okay to maintain the status quo, and my partners did the same.

So there I was — 28 years old and I’d never sent a dirty text. Ever.

I always thought What if someone takes a screenshot of this, shares it, and ruins my life? What if they don’t want to play along and I just feel stupid?

Sexting — like all expressions of our sexuality — is best when one feels safe. And upon reflection, I’d never felt that.

My sextual revolution happened over the holidays.

He was in a location that didn’t get good cell reception. We were messaging more often than we were talking on the phone, or doing any kind of video chatting.

One morning, I woke up and felt totally turned on. I had a sexual fantasy about us the night before that was so vivid and wild, I remembered every moment of it.

I texted him.


He responded quickly.


I knew that I wanted to be in a relationship where everything was on the table, including my full spectrum of sexual thoughts. I remember thinking, only by showing up to this moment completely, will I get to that place in my relationship. I wanted to tell him about my fantasy.


Read receipt and double-check. Typing.


Deep breath.


Read receipt and double-check. 
I continued.


Read receipt and double-check. Typing.


Time to go for it I thought.


Read receipt and double-check. Pregnant pause. Just a few seconds felt like an eternity. What was he going to say? How was he going to respond? I waited. Anxiously. He started typing.


I laughed out loud. I loved that he was right there with me on an emotional level. He wasn’t pretending to be too cool or immediately going into anything too serious. It felt a lot like us and our relationship. Silly. Fun. Real.

And that’s when the floodgates opened for me.



I can’t express how empowering it felt to put myself out there like that. I waited a moment. He was typing.

And sure enough, he was ready to share fantasies of his own. 
He continued…



It was incredible how intensely turned on I was — stimulated entirely through fantasy. No one was touching me. I wasn’t touching myself — until afterward.

I felt so connected and loved by him in those moments, and it was definitely a turning point in our relationship.

Sharing a dream made it easier.

The fact that my messages were grounded in fantasy felt more accessible to share than just bluntly saying, “This is what I want to do with you right now.” I was just letting him in on a dream. No big deal.

Everything’s easier to talk about now.

Even though we were close and open, sexual expression wasn’t very verbal before. But since we gave each other permission to share our fantasies over text, it has made everything more accessible to talk about. Not just sex. Our thoughts, emotions, everything. It’s all just more explicit — in the best possible way.

I’m so lucky to have found a partner that I feel safe enough with to explore this side of my personality. And it’s serving as a gateway to discuss and consider actual sexual experiences that I never thought were possible for me.

I’ve yet to see him in his unicorn onesie, but I know when I do, I’ll be totally turned on. :)

Special thanks to Naomi Nessim for the original illustrations.

Jared Weiss