I’m Sleeping With A Guy 20 Years Older Than Me And You Should Be Too


Of my 24 years on this fine planet, 23 of them were spent orgasm-less. I unceremoniously threw my v-card to wind at 18 and within those five years of average sex, had 6.5 partners. None of them were capable of getting me to that almighty finish line. But all that changed when I started sleeping with a guy twenty years my senior.

I get a few different reactions when I tell people this. The most common is a look of judgment/fear/shock/horror all mixed together with a packet of Sourpatch Kids. From this, it’s become obvious to me that a lot of girls equate sex with older men with wrinkly balls and wiry hair coming out of an array of orifices. And while I can’t speak to men over 45, to those girls: you really don’t know what you’re missing. Here’s why.

He’s a DILF.
Whether or not he actually has children, anyone over 35 with a full head of hair and in good physical shape is a graduate of DILF Academy. I’m talking strong arms, a good dress sense, and an actual willingness to spend cash on clothes, not just overpriced football tickets or Playstation games. Any girl in her early-mid 20’s that hasn’t fantasized at some point about shagging it up with a Josh Duhamel or James Marsden doppelgänger should question her mental sanity and/or be pushed in front of a bus, Regina George style.

He has a vested interest in getting to know your vagina.
… And not just in a “Hey, hi nice to meet you, let me just poke around down here—uh, hmm, err—is it time for sex yet?” kind of way. You see, it’s practically the 11th commandment that man shall be terrible at vaginas until quarter life and sometimes beyond. But being with an older guy means he’s had years to perfect, fail, attempt, and succeed in the boudoir. He understands that women aren’t water fountains and will take his time to figure out what works for you. And when he does, it’s like you’ve died and gone to some weird Oprah heaven where everyone is screaming “YOU GET AN ORGASM! YOU GET AN ORGASM! YOU GET AN ORGASM!”

Beyond this, having seen more than two kitties in his life, he realizes vajay’s don’t usually look like two unused Pink Pearl erasers and smell like Bath and Body Works vanilla bean body “crème.” This does two things.

A) It makes you less self-conscious, thinking “there’s got to be at least ONE girl he’s been with that has an uglier vagina than me.”

B) It makes him more grateful that you DO have the perfect-looking, peach-tasting vagina he’d never experienced prior.

Before him, I found oral sex to be down right disgusting. Going down on guys wasn’t a big deal, but when the train reached reciprocation station, I suddenly had my period… for 12 years straight. So a little note to the ladies that are still in this camp: it’s not gross, you just haven’t had it done right yet.

Normal sex feels like sex on ecstasy.
Regardless of how many gold medals he’s earned in the dick-swinging Olympics, younger dudes in their early-mid 20’s just aren’t confident in their own skin yet. Older men are so much more self-assured in their abilities and don’t feel the need to rush any part of sex, which is part of the reason why it’s so next level. He’s already gone through his “awkward, unsure, ‘what happens if I press this button?’” phase and he knows what he has to offer and isn’t out to desperately seek validation from anyone.

Which means all of his attention is focused on pleasing you — AKA, the way it should be.

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Drunk but not in love

(@DrunkNOTinLove) is a die-hard Splenda addict who requires a constant supply of caffeine and male attention to make it through the day. After graduating with her degree in Economics, she now focuses her energy on adding a "Home" to her degree title by perfecting the "intelligent drunk," and conning a banker into marrying her one day. Originally from New England, she is a hardcore Boston sports fan, but only when boys are around. Almost all of her calories consumed Thursday - Saturday (and the occasional Tuesday) are from $7 bottles of Yellowtail Moscato, and in no way, shape, or form is she fazed by this. All forms of hate mail and date party inquiries can be sent to

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