What I Learned Using Ashley Madison to Cheat on My Wife

If you google around for articles about Ashley Madison, the online dating site for married people, you'll usually end up reading variations on one of two pieces. The first is an article by a male journalist who signs up to the site "purely for research purposes," meets some women as part of his research, doesn't have the decency to actually sleep with them, and then uses this research to draw shoddy conclusions about the kind of women who use the site. The second is written by a woman whose marriage has gone stale, ends up using the site, maybe has sex, and learns some valuable life lessons by doing so. This article is neither of these things.

Background: I'm 40ish, a college professor in the UK, an upstanding member of the local community, married with kids. I'm also a sex addict. Or, I'd admit to being a sex addict if I actually accepted that sex addiction was a real disease, as opposed to just a term used to pathologize people who like sex a lot, particularly the weird stuff. Call me overly subjective, but I assume that everyone is addicted to sex at heart—it's just that some people are too uptight to admit it. If I were trying to justify that last statement, I'd say that my wife belongs to the latter category, but that would be a lie. She's as addicted to sex as anyone, except that for some weird reason, she only wants to have sex with me.

I'd messed around on Tinder in the past with some success, but while I'm clearly a scumbag, I'm a scumbag who doesn't want to get caught. I've found that meeting someone on Tinder involves double the amount of lying—lying to my wife about what I'm up to, but also lying to my matches about my situation. As good a liar as I am, keeping up this level of deceit can be tiring. Ashley Madison seemed like a way of addressing both problems. Anyone on the site who recognized me was likely to be as morally compromised as I am and therefore unlikely to blow my cover. And if I managed to meet someone, I wouldn't have to make up some cock-and-bull story about having to be discreet because I'd recently separated from my wife, yada yada yada.

So I set up a profile on Ashley Madison, posted a discreet photo, and bought some credits in the hope that I might eventually meet some other married sex addicts. And this is what I learned…

What a surprise, eh? A website populated by men who want sex, but don't want to get found out, is the perfect place to rip someone off. However, most of these con artists have the sophistication of a Nigerian 419 scammer and are fairly easy to spot. One of their biggest flaws is that they use photos of porn stars for their profile pics, without realizing that most AM users probably spend more time watching porn than they do playing with their kids. Some of these profiles cut right to the promise of whatever sick shit turns you on. Others play the long game, spinning out a story over days, weeks even. The first kind are pretty easy to spot, the second, less so—a lot of effort goes into some scams, and I'm not too proud to say that I ended up getting strung along the first few times, stopping just before getting seriously burnt.

Whichever approach they take, it usually ends up in the same place: They either ask you to sign up to a "ticket site" or ask if you want to webcam. Ticket sites are, supposedly, a place where they can anonymously verify your identity, to protect themselves—the only problem being that you verify your identity by giving your credit card details to an Eastern European fraudster who installs spyware on your computer. And webcamming? Well, for some weird reason, they never want to use Skype, but happen to know of this great site where you can set up a profile. "Of course it isn't a scam, baby. Trust me." The first rule of Ashley Madison: If it seems too good to be true, it almost certainly is.

If you find a profile of an attractive woman under 25 and she doesn't turn out to be a scammer, then she probably is out to get paid. It's pretty reasonable, I suppose—why would she want to sleep with paunchy married men for free, when she could sleep with a muscular, tanned twentysomething who probably shaves his balls (see below)? Why would she pick you over him unless there were some other incentive? Some men think that if they offer to pick up the tab and book an Uber rather than make their lady friend take the bus home, these impressionable young things will fall into their arms. That's not the way it works. Sugar babies want an allowance, they want to go shopping, and after you book the Uber home, they want to take it alone.

Even though you know that the attractive under-25s are going to tap you up for money, you're probably still going to approach them. I mean, they're as close as you're going to get to the porno fantasy that made you sign up to the site in the first place. Every now and then you ignore your better judgment and send them a key to access your photos along with a message that tries to come across as sexually interested but not too weird. Most will ignore you, especially if you tell them that you're not interested in being a Sugar Daddy. But the ones who do respond will inevitably turn out to be weird.

These women will send you messages that are so tasteless you'll think the production crew of To Catch a Predator is targeting you. I've had one girl brag about her "young-looking" body before sending me photos of herself with a former lover—a former lover who made her dress in his daughter's swimsuit before fucking in said daughter's bed. Another wasn't interested in meeting for a traditional dinner-and-drink sort of date, but she did send me her address and leave a window open so that I could climb in at a prearranged time and play-rape her. Roleplaying incest isn't really my idea of fun, nor is explaining to the cops that I was fulfilling a woman's play-rape fantasy, should it come to that. I politely declined both overtures.

Even when things aren't that extreme, my impression is that sex has become a lot more… experimental in the decade since I got married. Now, this is far from being a scientific study, and it may just be that AM users are more likely to go for some kink, but it seems like spanking, hair pulling, bondage, and even choking are now prevalent, if not ubiquitous. And anal. When I was starting to have sex, back in the 1990s, anal was an urban myth. Blame internet porn if you like, but ass-fucking is almost always on the table now, whether that's to your taste or not.

On that note…

A secondary consequence of the ubiquity of porn is shaved balls. Again, my view of sex might be getting distorted by the type of person who uses AM, but I'm going to throw another less-than-scientific generalization in here: In the UK, it seems to be the norm for men to have some hair around their junk. You might have to trim it a little so you don't look like a tramp, but you're not expected to look like a toddler. In the US, shaving seems pretty much compulsory; I once spent weeks—literally, weeks of late-night texting, emails, phone calls—setting up a date with a woman who was way out of my league. She was the right side of freaky, didn't want to tap me up for cash, and sent me a barrage of explicit selfies. I was visiting LA, and she was going to join me for the weekend but then gave me an ultimatum. Either I turned up as hairless as a snake, or the deal was off.

Her argument was that I'd expect her to be waxed to perfection, so why should things be different for me? She was blind to the fact that if I came home from California with a bald sack my wife would probably cut it off with scissors. Shaved balls were a deal breaker, and we had to call the whole thing off. My tip: Ask about this up front, as it'll save you a lot of hassle.

After a few months, you start to gather humorous "worst AM experience" anecdotes, which make a useful icebreaker when you eventually meet someone semi-normal. They're usually fairly predictable—people who look different from their photos, people who ask for weird sex stuff right off the bat, and so on. Mine trumps the lot of them. I had been in contact with a young attractive American girl who was visiting the UK. We emailed, then we swapped messenger details. Texting took a sexual turn fairly quickly—we traded nudes and pretty swiftly moved on to phone sex. I arranged to meet her and spent the entire train journey into town exchanging a series of increasingly filthy texts. As I changed trains, my phone rang and her number came up.

Her: "Hi, Daddy. What are you doing?"

Me: "Just changing trains. How about you?"

Her: "Playing with my big cock"

Me: "Sorry?"

Her (voice dropping from soprano to bass): "You heard me, daddy. Playing with my big cock."

Personally, I'm willing to accept the argument that gender is a social rather than biological construction, and a pretty fluid one at that. Having a cock doesn't automatically make you "a man." But it soon became clear that this guy didn't see himself as existing on any kind of gender continuum. He was a dude who liked to catfish married men. In all fairness, even after the big reveal, he still offered to come to my hotel and suck me off. Again, I found myself having to politely decline.

Let's not turn this into an infomercial: I spent hours, days even, sending out messages to dozens of women. And it wasn't cheap. You have to buy credits that allow you to initiate contact, and having quickly done the sums on the back of an envelope, I found it costs about $2.50 for each woman you say hi to. So while I was sacrificing hours of quality family time to type out charming opening lines on my phone without my wife noticing, I was also paying through the nose for it. I'd guess more than 80 percent of messages get ignored, and most of the other 20 percent fall into one of the categories above. But if you're determined, capable of writing in full sentences, relatively attractive, and not a psychopath, you can meet real women through AM.

My first few meetings were more like job interviews than dates. We'd arrange to have coffee, choosing somewhere discreet enough for us not to get spotted together, but public enough that someone would notice if one of us tried to strangle the other. On one of those first few dates, I arrived early, she came in, and we both knew within seconds that it wasn't going further. She complained about her inattentive husband, I made something up about my wife being frigid, and we swapped stories about our depressing marriages for long enough for it to be polite. Then I left, got on the train, and tried to make sure that I sent the inevitable "thanks but no thanks" email before she did. "No spark" or "no chemistry" is the polite AM-ism for: "We're never going to fuck."

After a couple of these, I started to think that AM functions more as a therapy session than a way of getting laid. Some of the women I met begged me to go back home and take out my sexual frustration on my wife. "She'll love it," they would say, even after I had explained that my wife is as vanilla as they come, and what she wants and what I want are very different. Others ran a mile when faced with adultery in flesh-and-blood form, rather than just words on a screen. But if you persevere, it eventually may well work out.

Articles about AM inevitably end with a moral lesson. Usually, they're something along the lines of "cheating women are just craving attention from their overworked husbands," or some such patriarchal bullshit. My lessons are much simpler: Avoid the sugar babies, don't give out your real identity, and be ready to play the long game. It might cost more money and take more time than it used to when you were single, but stick with it and AM can help you ruin what's left of your marriage, eventually.

Check back tomorrow for this article's companion piece, an essay on the Ashley Madison experience from the perspective of an anonymous female user.