Bloggers Assemble: Greatest Age Gaps Between Lovers

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They say “love knows no age.” But is that really the case? We wanted to know. So rather than take to the streets and seek out real-life examples of May-December lust in action (always a risk, especially if a woman’s into ball-munching and your grandfather), we asked some of our favorite bloggers to tell us about the widest age gulf that’s ever existed between themselves and a lover. And what–if anything–they learned from the experience.

Alex from The Urban Dater: When I was 22 I dated (like for a month) a 38 year-old woman. It’s not that I was slick or particularly handsome. I was tall. That’s all I had going for me. And the first time she invited me over to her place was to watch a movie (Legends of the Fucking Fall of all things).

After about 30 minutes of sitting on her couch she kept staring at me. I was nervous and paralyzed. She said, “You know, I think it would be fun if I climbed you.” At the time, when I got nervous, my fucking eye brows twitched. And twitch they did. What I learned is that I sucked at sex. To that point, I’d only been with two girls and both were passive, so I didn’t learn to get creative with them and I certainly didn’t put any knowledge from all the porn I watched to good use. No, I was a dead fish in the sack. What Inez let me in on was that women like a little (in her case a lot) of pain with their pleasure.

“Pull my hair! No, fucking PULL MY HAIR, FUCK!”

I pulled her hair, tossed her on the bed, or wherever we were fucking, in a forceful manner. I spanked, smacked, choked and did a lot of shit I wasn’t quite comfortable with, with this older woman. I will say this, she had an amazing and taught body; she was a runner, played softball and had an unfairly gorgeous daughter who was 18/19 that I had no chance with. I remember her daughter saying once, while I was at Inez’s house, “Mom, who beat the shit out of you? What’s up with your arms?” I sat in silence. I’m rarely silent, mind you.

At the end of the day I learned that there’s a lot of women who like the rough sex. I mean really fucking like it. And I also learned to be a little less gentle. Even if you don’t do the rough lovin’ you still have to be assertive during coitus. If a woman isn’t the take charge sort then you better be, and that goes for most things in a relationship.

I’m 36 now and I’ve dated/done some early 20-somethings. And I have to say, older women are better every day ending in “y.”


HLBB from Her Little Black Book: A group of us had headed to an island resort, and of all the vacation options available this world, “all inclusive” my least favourite type to take.

Night 1

Restless from the moment we pulled up, I showered and joined my friends at the “nightclub”. Working behind the bar were two men. The first bartender was an Adonis-looking guy that had a line up of 10 women waiting for watered down drinks. As I shook my head at their metaphorical thirst, I sat down at the opposite end of the bar and observed the fuckery.

When HE came over, I forgot all about the fuckery. There was at least a 20 year age difference between us. I asked for a mojito, but they were out of simple syrup. For some reason, I pouted and said in response “oh, papi… you just broke my heart.”

“I’ll find a way to make it up to you.”

Night 3

Feeling trapped in paradise, I asked Him if he knew how I could escape into town. He said that he would love to take me on a tour, but staff were also confined to the resort 21 days at a time. I wondered how they got to unwind and He explained that there was a place just outside of the resort that staff sometimes escaped to. It was mostly husbands and wives who couldn’t stand long periods of separation.

He smiled. I smiled.

Night 4

“So…”

“So…”

“I don’t understand. I’m an old man.”

“I don’t see old. Besides, I’m just another tourist.”

He laughed. I was wrong. Because of Adonis, no one paid attention to him like that. He was able to just do his work with no distraction.

“But then I saw you… and you pouted… and called me ‘papi’. ”

I smiled. “Oh papi…”

“Papi” then picked me up and put me on top of the bar… we did just enough to get him fired…

Night 5

A driver was hired to take me off the resort and I was taken to the staff hang out.

Trust me. He was NOT. Old men don’t go four rounds and there were NO tricks to teach this old dog. We talked, shared stories, learned about our lives, and laughed. It felt like the perfect first date; or that we had been together forever.

All mixed with acrobatic sex sessions of course. Ex merchant marines for the fucking win.

What was amazing was that I learned that there was a way to be adult about it. There were no games, no confusion, and no bullshit. We were going to do something neither of us had done before, and we were going to enjoy it.

Night 6

I took up my post at the bar and watched my single girlfriends flirt with Americans. He was assigned to a VIP table for the whole night.

Adonis came over to my end and placed a fresh mojito in front of me with a smile and a wink.

“This is from your friend. He also said to say that he told you he’d make it up to you.”


Kendra Holliday of The Beautiful Kind: My biggest age gap between myself and a lover was 53 years — he was 91, I was 38. His wife died a couple years ago, but they hadn’t been intimate for decades. So the last time he had sex was in 1976, not long after I was born!

We had a date in his apartment. He made us drinks, we danced, we flirted, and then we went to the bedroom and undressed each other, a condom on the bedside table.

Unfortunately, we weren’t able to use the condom. His penis had shriveled up and disappeared from years of neglect. There was nothing even there to be flaccid, it was reduced to a peehole.

This didn’t bother me, but it bothered him a great deal. He asked if I thought Viagra would work. I didn’t think so, his genitals were atrophied. Note that this is NOT typical for older people who have remained sexually active. I’ve worked in nursing homes and have seen all levels of function and body types in people in their 80’s and beyond.

On the plus side, he did go down on me, and that was the first time he ever performed oral on a woman.

It wasn’t long after our date that his daughter stepped in and forbid us from seeing each other again. I think the experience agitated him, which was not my intent. I always want to leave people better than I found them.

Moral of the story: USE IT OR LOSE IT.


L.A. from Chicks in the Mitt: My friends give me shit all the time for “dating” younger men.

L.A.: I met someone.

ALL FRIENDS EVER: HOW OLD IS HE??

The biggest difference? I was 25 and dated a 20 year old? DON’T DO THAT. THE DRINKING THING MAKES SHIT AWKWARD.

What have I learned from this?

One. Never tell my friends the age of whoever I’m dating/seeing/seeing naked.

Two. Younger guys are hit and miss. ON ONE HAND. They have so much energy. They just go. If I’m tired. They still go. ON THE OTHER HAND. Experience, of course, comes into play. Younger guys wanna try everything because they haven’t before. I’ve been there, done that. I know what I like. Yes, I want to keep things interesting, but I’m no longer interested in buying the kama sutra just to see if my legs can bend that way. They can’t. I TRIED.


Author/blogger Marsha Cornelius: I was 21, he was probably 45, the sports writer at the newspaper where I worked. He was very “thorough,” and the next day when I came into work, somewhat chagrined at my drunkeness the night before, he was waiting for me at the front door with a smiling face and kind word. I realized I didn’t have to be ashamed, or embarrassed by my sexuality.


Ariel of KenandAriel.com: I’d say the largest gap was 22 years – that toddler was somethin’! I kid, I kid, obviously. He was 22 years older.

What did I learn? Conversation hits a wall after a certain point. Same with the younger dudes, especially the ones who aren’t old enough to rent a car. Now, I hear that conversation should be the last thing on your mind if you and your boy-toy are riding shotgun to Screw-like-ferret-Town, but there are times when you come up for air or Gatorade or a smoke and look over and think, holy Christ, I have nothing to say of remote interest to this person, who will not get it, not understand, or worse, knows more at his tender age than I ever will. He remembers high school and his prom because it happened 5 years ago, whereas I have trouble remembering the date and decade. Will his friends mistake me for his mother, even though it would have meant that I gave birth at 11 years old?

And with the older man, I feel my age — that is, I feel a sense of false superiority because of my relative youth, mixed with a healthy daddy complex. Yes, that is indeed me pouting in the corner because we’re not going to my fave dive bar when you want to go to someplace more “respectable”, as in, “takes credit cards.” I worry about having him come along with my friends because he’ll be bored, or worse, they’ll be bored. And the biggest fear (and misconception): the Viagra dosage will have to keep going up to get it up.

So, I don’t know if this answers your question, but I do know what I’ve learned: that I’m a vain, egotistical, superficial twat, and should probably stick to my own age. Alas, since I live in LA, I already aged out of their desirable demographic about 10 years ago.

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