Never Have I Ever: Hooked Up With a Cougar

Have you ever played “Never Have I Ever” before? Here are the rules: Everyone puts up ten fingers, and you go around in a circle and one by one share something sexy or scandalous that you’ve never done before. When someone else shares something you have done, you have to put one finger down — and of course, drink. The first person to put all 10 fingers down loses (or wins, depending on how you look at it). Well, AskMen is still playing Never Have I Ever, and the rules are simple: In each edition of this column, we speak to someone about doing something new in bed, whether it’s a long-time fantasy, something that just happened, or even something they regret. They tell us everything so you get an inside look at what some sexual experiences are actually like. In a world of Botox, Gen-Z Hollywood starlets, and Harvard researchers clamoring to figure out how to reverse aging, the tidy cultural synopsis is that youth is prioritized at all costs. Woman over 35? Better empty out your wallet for some nasolabial filler, stat. However, while that narrative benefits the dermatologists and plastic surgeons (and insert required note that, of course, people should be able to do whatever they want with their wallet and face), it isn't actually representative of how age factors into sexual attraction, especially for straight men. Enter scene: The allure of cougars, the older, confident women who drag the bodies of hot young men out of the grasps of Zoomers' teeth and into their (much nicer) beds. To learn more about why older women are hot, we spoke to Sally* (not his government name), a 32-year-old living in Los Angeles. Sally lost his virginity at 18 to his 45-year-old former substitute teacher. RELATED: What It’s Like to Explore Age Gaps in a DDLG Dynamic While he spills about that first time, it also wasn't his last. Since then, he's exclusively been with women over 55. Read on to explore his insights on the joys of the cougar: AskMen: What is your experience with cougars? Sally: That's a very broad, but easy question to answer… a lot. I've exclusively dated, fucked, and fell in love with women over the age of 55 for the last twenty-four years. What was your first experience? Believe it or not, I lost my virginity to a woman who was 45 at the time when I was 18. Not to mention, she had been a substitute teacher at my high school. To answer your immediate thoughts, no, nothing happened during my time in high school. RELATED: Everyone You Shouldn’t Sleep With, Ranked However, it only took four months to literally run into her when we were both out jogging. We talked, reconnected as former teacher-student acquaintances, and shared emails with one another. After three or four emails back and forth, she unloaded on me and exclaimed how she thought it was kismet that we crossed paths and asked to meet for lunch at a diner. The next morning, before I commuted to university in the city, I met her for the two egg, bacon, and potatoes combo and talked about memories from high school, then onto the important subject… when can we see each other again to fuck! A week passed, and I lied and told her that I'd already lost my virginity to a new college friend; she invited me over at 10:00 pm to her house, which was only 15 minutes away from where I grew up. The rest is history. What is your current relationship status? Happily in a long-term relationship! Why do you prefer older women? I know the real answer is that I have some sort of mommy complex or that there's some screw loose in my head, but my reality is that the unconventional way my mind works aligns with people of a different generation. I'm not interested in “building a life” or starting a family because, through my life experiences, I've found fulfillment and solace with myself, and I seek a partner that elevates my life and what I already have going for me. Besides all of that, I find “age” on a woman very attractive. Overdone makeup (or glam), up-dos with hair tinsel and juvaderm injections are a huge turn-off for me. What are myths and misconceptions about dating and sex with older women? It's difficult for me to answer this question regarding dating because in the past, most of my dates with older women came after sex — those dates were always good and easy! RELATED: Can Age-Gap Relationships Work? Now, let's talk about sex, baby… (I'm not even a dad) Do not underestimate the libido of a woman over the age of 60. Women know what they're doing, and more importantly, they know what they want. Listen to her, follow her movements, and relax. There may be a possibility that she's a little more nervous than you. Will you tell me a little bit about the romantic/relationship side? Sure! I've had four serious relationships with women over the age of 60 that lasted more than two years. Though the ones prior to my current relationship didn't work out, I was fortunate to walk away from them with worlds of knowledge, experiences, and the kind of love that one would be so lucky to have. Falling in love with mature women is bliss and, simultaneously, a dangerous game. In 2013, I met a woman on a trip to LA when I was living in NYC. We kept in touch and visited each other for a couple of years until I got a job on the West Coast and moved to the city of Angels for my career and to really be in the relationship. This, I think, was the deepest and most intimate that I was in a relationship. I trusted her so much that I confided details of my past that I never thought would leave the dark halls of my mind. I felt safe. Fortunately and unfortunately, I was with her to the end. In 2017, she was diagnosed with a fatal disease and fought strong and hard for a year and a half. Falling in love and losing them before it's over is a thing that I wouldn't wish on my worst, I mean, worst enemy. Well, is it ever over for anyone? It took me years to find myself out of the mounds of feelings of grief and misery, and to this day, I live with remnants of sadness and thoughts of what could have been. What advice do you have for other men dating cougars? The women that I've met at this particular time in their lives gave it everything that they had in these relationships. They worked through trials and errors and successfully navigated through prior relationships and "situationships" (as the zoomers call it) that there's no use in trying to change them; rather, you should learn more about her and where she is at in her own life and see if you are a missing piece to their jigsaw puzzle. Don't treat any woman as an object to fulfill your sexual kinks or fantasy — especially my cougar queens. Besides, technically, they could be your mother! You Might Also Dig: What a Man's Relationship With His Mother Tells YouThese Redditors Taught Us All How *Not* To Pick Up Older WomenWhat Does It Mean to Have a 'Type' in a Dating Context?