My Ashley Madison Life!

Navigating adultery for men is what I do now

Photo by Dave Hoefler on Unsplash

I’ve been on Ashley Madison for over four years — first as a meek gal searching the unknown married dating space. Then, the second time to reprise a lady’s first time on the app about two years ago, and I still maintain that account. And now, as I write this, I’m monitoring three client accounts in the background.

My clients are all men, so the shoe’s on the other foot, but who better to know what a lady wants to hear than another lady? I’m also better at keeping it clean, however, on one occasion, the lady, possibly a little drunk, began sexting within about five messages.

As a sex writer, I can sext with the best of them, but I generally leave the sexy stuff up to my clients. Why? I find writing sexy things boring if they aren’t for me. That might sound funny, but explicit sex stories, which is what sexting is, can be tedious to write if you’re not in the mood.

What was it like sexting a lady?

Well, it was ok. I’ve sexted with a woman before and then spent the weekend with her doing the things your imagination suggests we did. But the sexting, in that case, was what I wanted her to do to my girl thing and what I wanted to do with her girl thing.

The keener observer will notice that I don’t have a boy thing. While I know what they do and how they do it, I really wasn’t in the mood to pretend I had one, but I managed.

Overall, I wasn’t into it, and as I was doing it, I was furiously messaging my client, asking him to jump in. Oh well, I truly am a girl for all seasons; it’s just that I don’t like the wet one.

What do I do for my Ashley Madison clients?

For the ones who pay for it, I will message women and start conversations with all those who reply. I’ve had as good as 70% of my messages opened, and 40% of my messages result in a conversation.

And anything that results in a conversation is where I take over. Some men have difficulty getting it moving and holding her attention, so that’s where I come in.

Depending on how well I get to know my client, I can carry on a fairly long conversation with them. When I’m stumped with a question, I turn to google. That’s usually to figure out how far apart we are, or in one weird case of 20 questions — what my last meal would be.

What would my client’s last meal be? Well, he grew up in a Jewish home in Brooklin, so I wondered, what would he have eaten as a boy during the holidays?

I figured if I was ordering my last meal, I’d want it to remind me of childhood, my mother, my family, and the holidays. So I Googled traditional Jewish American holiday food, and in less than two minutes, I had my reply.

That was one of the toughest and most boring conversations I’ve ever had with someone. She insisted on asking me question after question to the point of absurdity. I did alright and asked some back, but I eventually steered her away from it.

My client ended up letting her off the hook, and that conversation had much to do with it. Why? There wasn’t any original thought there, and certainly no depth. The other reason was we had four ladies chatting by that point, and she was the last one in the door. My client cut her loose very gently.

When do my Ashley Madison clients take over?

I usually ask them to jump in when more intimate details are discussed or they switch to another chat app. When I mean intimate, I’m referring more to family details of where they grew up, schools they attended, and trips they took. Things like that, in addition to the sexy stuff.

I also don’t follow them to chat apps like Kik or the dozen others because it’s too hard to chat and report back. On Ashley Madison, both the client and I can be logged in simultaneously, so they can monitor the convo. That’s not possible on the chat apps, so I play telephone with the client, which takes a lot of energy.

I do coach them while they are solo chatting. I always tell them that if they think they are in touble, to stop! Let me know what’s going on, and 9/10 times, I can get them back on track.


When I’m chatting for a client, I am the client. I learn about them and their online habits so I can mimic them. That way, when they take over, she’s none the wiser. Is that wrong? No, because I don’t play tricks. I just help my guys through the difficult early stages of the chat.

What do I charge for that? $300 on top of the $500 they pay for my top-tier service. Does it work? Well, most of my clients have their first sex date within a month of me starting with them. But like anything else in life, there are no guarantees, but if anyone’s going to get you there, it’s me.

Have a question? Email me at —

Check out my products and services using this 3rd-party link to my website, — HERE!

Want more Ashley Madison tips and tricks? Follow me on at Teresa J. Conway!


Author of How to Cheat: Field Notes from an Adulteress, several short stories, I'm active on Medium @teresajconway where I sometimes share my blog posts.

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