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Nina Collins
May 7, 2021

Illicit Online Dating

Tales of Extramarital Activities

I’ve used a number of hook-up sites for married people.

During a recent Monday night Sex Chat — subject: “Sex With Strangers” — conversation led more than once to members’ experiences on the Ashley Madison dating site, a site I knew of only vaguely as a place where married people go to have illicit affairs, and where there had been a famous data breach. Curiosity led to a solicitation of stories, and here below is a sampling of what women in our community were willing to share about their experiences.

The One Who Was In An Open Marriage

On the day my husband and I agreed to an open marriage, he told me that he had put his profile on Ashley Madison. I did the same —no outward facing picture and a fake name with a short description of what I was looking for.

Within 24 hours I had more than 200 messages – most of them from men who gave me access to their private galleries, full of dick pics, and wanted me to give them equitable access. Very few of the men actually sent messages with substance. While AM is free for women, for a man to send a message, it costs him money. But they can send “winks” (I still really don’t know what that is!) and request to access your pictures.  It was overwhelming.  I had to sift through a lot of garbage to find real prospects. Most guys have profile names like “pussylickr” and “eatuout” if that’s any indication. Not all of them are married – about 30% are single guys looking for a hookup from a horny and bored wife.

Within the first few days, I found a couple of cute, college-educated dads with kids about my age with whom I connected easily. I had a few brief affairs, but none lasted. Each one was plagued with guilt and incredibly paranoid. If we met and made out in the car, they had one eye out the window or in their mirrors at all times. And every single one of the married guys I spoke with, to a fault, said some version of “she’s a great partner and mother, but she doesn’t want to have sex with me.”

After a few months, I got off AM in favor of Tinder. Tinder and the other sites are simply less cumbersome, and there are plenty of men on those sites who are interested in casual sex.

And while the sense of doing something illicit and taboo and lead to great sex, I eventually gave up on married men as well. They are easy to bond with and relate to, but it simply isn’t worth the hassle of trying to find a safe spot to meet and the inherent drama that goes along with it.

Bottom line:  not worth the effort.

The One Who Found a Loving Steady On The First Try

I’m in a sexless marriage and by that I mean we have not had sex at all in over eleven years. We have probably only had sex five times since having our daughter, who is now eighteen. This is due primarily to my husband’s intimacy issues and his addiction to porn. I have had affairs throughout my marriage, usually with friends or colleagues, and each time I ended it, I vowed never to do it again and focus on the marriage. When we were most recently in marriage counseling, I read a book called Attached, the New Science of Adult Attachment and How it Can Help You Find--and Keep Love. I realized then that my husband has an Avoidant Attachment Style which was never going to change, so we quit going to therapy and I decided to resort back to affairs, although I had no prospects...

Enter Ashley Madison. I was only on the site for a few days, as it was very anxiety-provoking. most men posted gym pics and/or suit and tie pics, neither of which appealed. Some profiles were creepy  — too sexually explicit and/or bitching about their wives, both of which turn me off. Many profiles were of men claiming to be in sexless marriages, and looking for companionship and intimacy. A common phrase: "not looking to change my situation or yours.” I did not post any photos and learned that most women do not. I only searched for men in other towns, places where I travel for work. I went through and "liked" a few profiles and received messages back right away. As soon as contact was made via the site, we would switch to a private messaging app such as Kik or Telegram, which was fine with me, because I was so uncomfortable on the site itself. I later learned that men have to pay $3 for every message they send on AM (ugh).  Women do not pay at all. Once we made contact via the private messaging site I would send a picture. I only made contact with three men, and arranged to meet one in person.  When asked why men messaged women with no photo, the guy I met told me that because there are so few women on the site, men take their chances, hoping for a photo later. He also told me that men select women based on height to weight ratio.

When I met my date, I used a fake name and was not planning on revealing anything identifying about myself, assuming that this was just going to be sex. The first date was very transactional — I asked if he had had a vasectomy (no) and how he felt about condoms and abortion. I’m not yet in menopause and was not on the pill. We discussed STDs and availability; he was only available weekdays/nights which worked well with my heavy travel schedule. We discussed sexual likes and dislikes and briefly discussed our marriages,  agreeing that we did not want to disparage our partners. We both made clear that we were not planning on leaving our marriages (although I have since separated). We really discussed everything logistical, down to how we would pay for hotels (Visa gift cards), and it was actually kind of refreshing, knowing it was so clearly about sex and that everything was on the table. I think in normal dating, people often don't even discuss sex until they are doing it.

By the end of the first date, he knew my real name, what I did for a living and where I lived, and our relationship became more than sex pretty quickly. He's a great guy and we have a lot of fun together. We text throughout the day, every day, and talk on the phone when possible. COVID and working from home have thrown a real wrench into things, I must say. Pre-COVID we saw each other about twice a month, and now we may go 4-6 weeks without seeing each other,  and we rarely have an excuse for an overnight these days. I think we would likely be a very compatible couple if we were in a "real" relationship, except that I suspect he's a Republican. On our first date, I said "if you are a Trumper we must never discuss politics." He replied "I have no interest in discussing politics.” he asked why I “liked” him, I said "good grammar.” LOL.

The One Who Met Her Fiancé

I was a regular user of Ashley Madison starting summer of 2009 through spring of 2010. It was being marketed heavily at that time and I believe this was before Tinder existed. I wanted "hookups with no strings" and I was too skeeved out by Craig's List. Part of my thinking was that married men were less likely to be axe-murderers and that they wouldn't want anything more than sex. I have to confess that I didn't really think much about the wives. I had gotten divorced in 2007 and had also just ended a really bad relationship with a boyfriend who was awful,  so I was just up for some sexual adventure and did not want a relationship. I dove in!

If I remember correctly you could put up a profile photo and then add a folder of other pictures that were "locked" that you could then give permission for other members to see. I think that's where you could put nudes. I never did, but did have several up of me in sexy undies. Many guys didn't have pictures up and you could request an image if you decided you were into someone. There wasn't an app (or if there was I didn't use it);  I only used the desktop version. I don't believe there was a "swipe right" sort of deal, I think if people were into you they just inboxed you. The ratio of men to women was very much skewed towards men, so I got a lot of messages.

Quite a few guys were just there to have sexy chat and enjoy the "rush" of something clandestine and had no real intention of hooking up in person. I remember there were a staggering amount of cops, firefighters and airline pilots. I also remember there was a "panic button" where if someone was getting super sketchy with you you could report them. I never had to use it. I did have one guy who was constantly sending me sexual memes, and I finally said "enough is enough, just stop" and he apologized and knocked it off.

During that time period, I'd say I had sex with about 10-13 men. Many were literally just one "night" stands/one time only sort of deals. Looking back, I know I put myself in a lot of danger and it's pretty scary actually to reconsider that now. I was having these guys over to my apartment without telling anyone what I was doing! And usually I had a few drinks beforehand to ease my nerves. I guess I’m really lucky I wasn't robbed or attacked, but I never had a single problem. They came over for sex, and then they left.

I usually asked the guys I was talking to or saw in person why they were cheating and the reasons ran the gamut: several had wives who had just had babies and sex was off the menu, one man's wife was very sick with cancer and she had "blessed" the hookups, and several guys just felt like the sexual energy was gone in their marriages.

I did wind up having two "regular lovers,” interestingly enough both European, and their attitudes about our hookups were very different from the American men. One from France, the other from Spain. Neither of them gave off the "I feel guilty" vibe, and would regularly talk to me about their wives and kids, clearly still very much in love but just seeking sex elsewhere. Alejandro was a sweetheart; we would go out to lunch, go back to my apartment and have sex. Laugh, talk and then he would leave. He usually brought me flowers and boxes of condoms and reminded me all the time to have safe sex with my other partners. He was just such a sweet, wonderful guy.

Then I met Dave, my now-partner/fiance. He was very clear from the beginning that he was in the process of moving out of the marital home and starting the divorce process but still very much married. His wife was (and still is) an addict and an alcoholic who was never planning to seek treatment, so he really felt like there was real no marriage left to save. It became clear to both of us pretty early on that we were falling in love. Once we realized we weren't interested in other people and wanted to try and establish something real, we both closed our AM accounts and stopped seeing anyone else we were hooking up with. Our cover story is that we met "at yoga" lol although somtimes when I'm caught off guard and say online I always add "" I have one gay male friend who knows the truth and doesn't care, but that's it!

One funny story:  one guy who came over to hook up, but was clearly feeling awful about cheating, proceeded to whip out the biggest dick I have ever seen in my life. I had no idea how this thing was going to fit anywhere. I told him I would need some good and long foreplay because of his size, so halfway through the "warm up" he stood up and said "I'm so sorry I just cannot do this, I cannot cheat on my wife!!" he pulled up his pants and fled my apartment as fast as he could. Honestly I was relieved, I STILL think of that penis!

The One Who Did It To Test How Attractive She Still Is

I’ve just ended my experience with Ashley Madison. I was on for two years and met many men. I’m married and my husband has no idea that I’ve cheated. I did it in large part as an experiment to see if I was still attractive to other men. I had some pretty wild experiences. But also really got my feelings hurt. It all started when an old crush from high school sent me a message through Facebook...

The One Who Has Two Accounts

Six years ago I found a lover on Ashley Madison that I’ve been seeing ever since. Before COVID, we met every Friday afternoon at a hotel.  I also met a few other guys using the site, and I’ve heard a lot of them complain of too many fake accounts or women who want to be paid for sex. I personally find too many men that want only car blowjobs, they don’t want to follow through with actual sex. Or guys that haven’t thought through the mechanics of having an affair, for example, no plan on how or where to book a hotel.

I’m bisexual, so I also have an account looking for women, but most of them are lesbians not interested in a bisexual relationship. No, my husband has no idea, and no, I am not in an open marriage.

The One Who Wanted To Explore Sleeping With Women

I used Ashley Madison specifically to meet married women and I met one who seemed really promising. Our husbands both knew we were looking to hook up with women and were ok with it. She and I met her a few times at her summer house;  she was in her 50s (like me), fit and beautiful. But it turned out that she was also an unrepentant Trump supporter, and I just couldn’t go do it, which was a bummer because that lake house was great!

The One Who Found Phenomenal Sex

I’m currently involved with a man I met on Ashley Madison. We are both in sexless/loveless marriages. For  my part, I’ve asked for a divorce, an open marriage, a parenting-only marriage, all to no avail. Having this other relationship makes my life tolerable until I can somehow get to a different solution. I have no reason to think my lover  isn’t being honest with me because we have no expectations of each other; we’ve made it clear that our current priorities are our families (meaning our children), our careers, and then each other.

Aside from first names and general occupations, we know almost nothing about each other. To us, that is the safest way to protect ourselves and each other. If I were ever to be caught by my husband, I wouldn’t even be able to be coerced into revealing a last name, job, telephone number, house address, because I simply don’t know, and it’s the same for him. We chat and arrange dates using kik. We see each other 2-3 times a month, sometimes for dinner/drinks, and other times, just for sex. We both were tested for STDs before engaging in sexual activity.

The sex is phenomenal; the guy I found is an incredible lover and has woken me up sexually in ways I never knew possible. He says the same about me. Again, no reason to not trust him as we have no expectations or investment in each other. We can truly be ourselves and 100% uninhibited. I wouldn’t change any aspect of our relationship right now and I know I am a more fulfilled person because of this experience.

I referred a friend I made through The Woolfer to Ashley Madison and she said she has met several amazing, successful, well rounded men who are just profoundly lonely. She never even sends a photo before they meet. She says they are so desperate for companionship that they really don’t care what the woman looks like. I'm sure it helps that she is in fact beautiful. Last we spoke, she hadn’t had sex with any of the men she met, just talking, cuddling and kissing. Some even write her poetry!

The One Who Felt Reckless But Alive

I’ve used a number of hook-up sites for married people. Ashley Madison was more clunky and less useful than some of the others, but I did meet two different guys who were in town for work, both at their hotels,  sight unseen. One came back a few more times and I kept meeting  him. I also met a half dozen other men first for coffee and then for sex, including one who was single who I met first at his home. I Googled him and learned he had been convicted for soliciting minors years earlier. I mentioned this to him, he explained, and I decided to meet him anyway. The sex with all but one of them (ED) was fun and it was a rush to meet unknown guys who liked me and my body. They were corporate guys, sales men, contractors, engineers, one owned his own landscape companies. Most of them were at least ten years younger than me. None of them were weird and I never felt unsafe. They all wanted to remain married and said they didn’t get enough sex with their spouses. Which is my story exactly. I never gave them my real name or phone number and we communicated over an app called Kik. I did this a few years ago in my early-50’s while I was still married. It was reckless and I wouldn’t do it again, but it made me feel so alive.

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