Older Women Younger Men Stories

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Older Women Younger Men Stories
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The relationship between an older woman and younger man is just fine with me
by Monique Ruffin | Monday, September 02, 2013
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He was thirteen years my junior, and I could never really relax with him. It seemed tawdry, and the distastefulness hit me front and center since I’d had a son of my own. It seemed wrong to do with another woman’s son what I didn’t want someone to ever do with mine. So I let him go, throwing him back into the river like a fish I’d caught for sport.
It’s taken me a while to admit to myself, but I guess you could say I’m a cougar. I was dating younger men exclusively, long before there was a label for women like me. When I was in my late twenties, I wouldn’t even look at a man if he was older than me, and the man I eventually married was seven years younger than I. When we met, I was twenty-nine and he was twenty-two, but he looked much older (at least, that’s what I told myself).
The truth is, I like beautiful men. I’m talking traditional, physical beauty. Think actor Nick Cannon (who, by the way, is married to Mariah Carey. He's 32, she's 43). Sometimes I hear my thoughts (“Look at those abs!”), and wonder if there’s a man in my head. I’m lustful in ways that are sort of embarrassing. My ex-husband would always catch me looking at men’s crotches. It was an involuntary reaction. I’m turned off by men who feel old, stuck in their ways, jaded by life. I know they say that youth is wasted on the young, so I’m out to help young men use their youth wisely.
After my first post-divorce fling was with a man sixteen years younger than I, one of my friends set what seemed like a reasonable boundary for me. I was not to date anyone younger than her oldest son. All I needed to do was gradually date men who were aging out of their twenties and into their thirties.
It seemed easy, at first. The thought of my young son coming home in his twenties with a fortysomething-year-old kept me true to my promise. There was Stallone, who’d come and visit me regularly at the shop where I worked part-time. His five-foot-eleven-inch frame, muscular build and dark chocolate complexion were tempting. He’d sit and talk metaphysics with me, asking questions and sharing ideas. It was fun.
But his nineteen years on the planet made me feel like a dirty old woman as I salivated at the sight of his shoulder span and lean waistline. His flirtatious smile didn’t help. Those gorgeous white teeth captivated me. Finally, one day after he’d rode the bus several miles to come spend the afternoon talking with me, I told him, “This is too much, I mean, I’m too old for you. Don’t you know any young women your age you can have these talks with?” Soon he stopped visiting.
I got good at asking men their ages within the first few minutes of connecting. That way I could put my fishing rod away before I even got out the bait. “Honey,” I’d say, “I’m twice your age.” I once even dated a man who was six years older than me. He was youthful, healthy, active and open. He also had those muscles I liked in all the places I liked them.
But my efforts were for naught when I met Jeremy. I’d been studying tantra, open marriage and sacred sex. I started talking to a man at an event who was alone and I immediately found myself attracted to him. After a long conversation, I knew I needed to ask his age. I also knew that it wouldn’t matter what he said, I just hoped he was at least thirty years old. When he answered “twenty-four,” I knew my promise would die a fast death, and I was about to allow myself to fall down the rabbit hole with someone twenty years younger.
For older men, a beautiful young woman is often considered a prize. Consider men like Donald Trump and Larry King, who sport their trophy wives on their arms, while the world looks on in admiration. In many cases, the younger woman/older man relationship offers a contract based on material exchange, youth and beauty for financial security.
But the relationship between an older woman and younger man will generally offer a very different kind of exchange — one based upon both people bringing who it is they are, rather than what they have. A wiser, self-realized woman can offer patience, pride and sexual instruction to a younger man, helping him become a dynamic lover and a fully realized man. A younger man can offer a wiser woman the youthful, vital energy it takes to satisfy her sexually and the playfulness that is difficult to experience with men her age or older. The experience goes beyond sex, as older women can offer younger men insights about life, love and the experience of the human journey.
If a woman’s looking for a man with a lot of money, chances are younger men won’t be of much interest to her. On the other hand, they won’t need a tiny blue pill to maintain their sex drive. I make it my practice to resist “parenting” a younger man, and try to allow him to truly practice his leadership and intellectual skills in the relationship. It’s more fun for me (I already have a son!), and I feel that I’m contributing to his development as a potential partner, making him more astute for the next woman he encounters. Plus, as a woman in her forties dating a younger man, I get to have the type of sex most people might only dream of.
I can honestly say, my most curious and willing lovers have been younger than me. Youth doesn’t get wasted on the young when I’m in the game. It gets perfected.

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“It was a whirlwind post-divorce experience."
If you're ready to accept that age is just a number, then your pool of eligible bachelors just got a hell of a lot bigger—and might include some much younger dudes. 
Plus, all the cool kids are dating younger these days. Kourtney Kardashian allegedly hooked up with Justin Bieber not long ago, while Carole Radziwill, the 50-something star of The Real Housewives of New York City , is currently dating Adam Kenworthy, who's more than 20 years younger than her. And, we all remember the OG cougar from Sex And The City, Samantha Jones.
Curious what it's like to get serious with someone lacking as much life experience as you? We asked real women to spill all the details of dating a more youthful dude.
"I once dated a guy who was 10 years younger than me. I was 36 and he was 26. We were at two different stages in our lives: He was still working at his first post-college job and I was the chief marketing officer of a tech start up. I was working long hours and making six figures. He was working eight hours a day and making $40,000 a year.
"What I loved about the relationship was that I felt empowered. I made all the decisions, like where we went on vacation or what spot we ate at. I would also pay for almost everything, like food, plane tickets, or a night out at a bar. I liked that, though, because I felt like I didn't need to rely on him for anything. I was able to have independence while also being with a person who made life fun. Whenever I was too caught up in work, he encouraged me to go out with him and party till 4 a.m. or ditch checking my email to hang with his friends. I liked that aspect of our relationship. However, we ended up breaking up after a year of dating because he cheated on me with someone two years older than him. At that point, I realized I didn't see much of a future with him anyway. He was, essentially, a kid." —Tamara K., 38 (This 20 Function Bullet Vibrator from the Women's Health Boutique is the only bullet you'll ever need.)
"When I was 41, I dated someone who was 33. I liked the thrill of it at first. He still enjoyed going to concerts, bars, and doing fun activities that weren't just dinner and a movie. We dated for three months. Honestly, he made me feel younger, and when we first started dating he thought I was his age. When he found out I was almost 10 years older them him, he was shocked, but said I seemed younger than my age. Ultimately, the age factor didn't matter much to him. We were both successful in our careers, we constantly talked about current events, and had similar political and social views. But, to be honest, it was exhausting to date him because he could never relax. When I suggested just spending a night at home eating dinner, he'd beg to go out and try a new restaurant or get a table at a club. Deep down I was more of a homebody, so it didn't work out." —Amy V., 43
"Back in 2012, I ended up dating someone I worked with who was 15 years younger than me. We found ourselves in a romantic relationship when we slept together after our company's holiday party. At the time, I had just gotten a divorce, so getting into a fast and fun relationship was a whirlwind post-divorce experience. It felt refreshing to date a good-looking younger guy. He said I was the oldest woman he had dated, but that he liked to date women older than him. We didn't have much in common, but that didn't matter. We had a great time together.
"Despite the fact that our relationship was going well, everyone in my life told me I was crazy for dating him. When my two kids found out (they were 8 and 11 at the time), they wouldn't even talk to me. They were mad that I had moved on from their dad so quickly and also found it weird that I was dating someone so young. My friends thought I was just trying to get revenge on my ex-husband, who had cheated on me. However, the only reason we were together was because our relationship made me feel good about myself. We only dated for five months, but that wasn't because of the age gap." —Wendy P., 47
"I was 43 and my now ex-boyfriend was 29, which actually isn't that much of an age gap. However, there were four or five times when we were out and people thought that I was his mother. It didn't help that he looked very young because of his baby face. It was embarrassing when I had to tell people that he was my boyfriend." —Olivia C., 44
See how real men and women feel about cheating.
"Everyone assumes that when you date someone younger they're more wild and immature, but it was the opposite when I dated a guy who was nine years younger than me. When we met online, I wasn't looking for anything serious but he was actually looking to settle down. He had just finished law school and was working crazy hours. On the other hand, I was working two part-time jobs, while auditioning as an actress. Despite me being older, I liked to joke around and party, while he liked to Netflix and chill . Ultimately, it didn't work out because he was looking for a wife and I had no marriage goals for my near future." —Alexia L., 37

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The first time someone sexually assaulted me, I was 14. I was on the commuter rail headed into Boston for an art class. I convinced myself he had just lost his balance when the train swayed and grabbed onto something. But it felt deliberate: He scooped my butt in his hands, squeezed it and his fingers went a little too far.
When he got off at the Fenway stop, he smirked at me. I was paralyzed.
I didn’t think much of that incident at the time. I barely knew what sexual assault was, and I had certain ideas about it. Namely it only happened to girls. When I read about Anthony Rapp’s allegations that Kevin Spacey had made sexual advances toward him when Rapp was 14, that encounter on the train resurfaced in my mind.
When you’re young and gay, these situations with older men are as unavoidable as they are for young women. Someone grabs at you because you’re in a public space, or you assume a guy is just being friendly so you’re friendly back … and then it takes an aggressive turn.
When I was 18, I went to an 18+ night at a gay bar with friends. Not long after getting there, an older man hit on me. When I said I was just here to hang with friends, he shoved me and said, “you twink sluts are all the same.” He was probably just upset over being rejected, but it left me feeling as though I had done something wrong.
Occasionally when older men would flirt with me online or in real life I would find myself flattered. Especially if they were handsome, or interesting. Though at 18 I didn’t understand why they were interested in me. I might have been legally an adult, but I still looked like a goofy teenager. These men weren’t five or so years older, but often twice my age or more.
I figured these men must have somehow been looking past my youth, past my braces and cartoon T-shirts. Often they’d describe me as “mature for my age,” which seemed like a good thing. Clearly if a guy in his 40s who has his life all set is interested in me, I must be something special. I didn’t mind talking with them and even felt flattered at times. Still, my kindness was often confused for flirtation. Simply being young is read as “leading someone on.” Once a guy asked me for oral sex while I was on a break from work, because I had smiled at him as I handed him his receipt. That was all it took.
When I rebuffed these advances, I was deemed the bad one. Like I was some sort of temptress just for being friendly and personable. Which is a double-edged sword women are often in the midst of. You’re rude if you flat-out ignore someone, but a tease if you’re nice before turning him down.
In real life these incidents were scattered, though on dating apps I could guarantee dozens of messages a night almost exclusively from men in their 40s and beyond, who will also send unsolicited nude photos or promise money. “I love young, fit, masculine guys” is a constant sentence you’ll find on older men’s dating profiles. It makes it clear the interest is not in you as a person, but in your body.
I didn’t have as many of these problems with guys my own age. It was always with much older men, often acting as if I owed my existence to them. Being a younger gay I often feel a bit guilty that I grew up in a generation less closeted, and at times it seemed like these older men were playing off that. They lived through Harvey Milk’s assassination , the AIDS crisis, and a time when you could be fired for being open about your sexuality. Here I was, being handed everything they worked for.
These older men never seemed to be interested in conversation or in getting to know me. We had nothing in common. All of my Pokémon and Harry Potter references seemed to go over their heads, and when I found their eyes trailing up and down my body as I spoke, I just wanted to leave. “Why are you interested in me?” I asked once. “I like younger guys,” he said, not even adding anything he liked about me in particular.
If I told a friend, often around my own age, I was uncomfortable with these men staring at me like dessert, they would say I was “age-shaming” or “not being sex positive.” I was stuck in this dilemma of wanting to socialize, but not wanting to put my body up for grabs.
As I reach my mid-20s, I can’t help but wonder why anyone that much older was interested in 18-year-old me in the first place. I look at pictures of me, and I see a kid.
For so long, I thought these older men saw me as grown-up and mature, that they were looking past my braces and Super Mario T-shirts. Now I realize they were looking right at them. They saw a kid, too. That was what they were looking for.

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