I date men that I could have babysitted.

Tonight I went on a date with a 25-year-old. Twenty.five.  ELEVEN years my junior.  I feel like a cradle-robber, an old fart, and a bad ass all at once.

I have NO idea what’s up with this slew of young men who want to bang me, talk to me and otherwise partake in my company, but I’m down.  There’s something innocent and charming about these boys who think they can hang with me.  I like their efforts.

And I don’t mean that in a condescending way, but come on.  A single, childless man in his mid- to late-twenties who’s never had a serious commitment, career, or care in the world is not and cannot be my peer.  I have lived several lives in the years that create our age separation.  Maybe even a thousand lives.  He can be sweet, sensitive, intelligent, fun, sexy, and passionate, but he cannot relate to life as a 36 year-old single mother with a graduate degree and a career.

My date tonight is by far the youngest person I’ve ever considered getting naked with.  He’s tall and lanky, all Euro-trash, but with a mid-west aesthetic.  He’s the oldest of four boys, in a band with his brother, and majored in English.  He reminds me of Georgia Jagger.

We drank cheap beer and shouted over the idiots at the table next to us (who would periodically scream at the football game overhead) and generally reacquainted ourselves after months of tenuous texting and recent sexting.  He’s spent weeks buttering me up and trying to convince me he wasn’t “that young” and when I caught him looking at me tonight there was something in his eyes that told me to believe him.

We huddled together, thigh to thigh at the outdoor table, exhaling smoke and hot breath.  I seized up with shyness and he felt emboldened.  “I’m usually the shy one at first, but eventually it wears off.  But you, Hyacinth, you, you’re going backwards.  You’re getting shyer.”

If he’d known my salacious thoughts, he’d have understood.

I leaned in for a kiss and he was surprisingly skilled.  I would have told him as much if I hadn’t thought it’d offend him.

I told him flat-out that I wasn’t monogamous and that I had three other lovers (one of whom I’d already promised to text once I got home so he could come over and fuck me senseless — though I refrained from sharing that little bit of info), and, most importantly I said, “And I don’t have feelings.”

His eyes widened at this.

“I mean, I do have feelings.  I care about all my lovers.  We’re friends, but I don’t love anyone.”

He quickly nodded his head to tell me he understood.

The thing is, I trust his judgment (I trust all men’s judgments to date me), but I’m still skeptical.  I really don’t know if he can handle fucking me without having feelings, but I’ve decided it’s not really my problem.  I’m curious to learn what he’s like in bed.

I kept leaning in for a kiss and smiling, my bashfulness thankfully gone.

My therapist is going to hate that I’m doing this, but I actually like the idea of adding another man to my bed whom I met offline and in a real life way.  Julian (I guess that’s what I’ll call him) and I met months ago at a trivia night.  His interest in me is real, from the ground up.  Not just because he likes some of my pics on OKCupid.

And then the clock struck 11 and I had to go home to fuck The Neighbor who laughed at the idea of someone even younger than him fucking me.  He took the time out of kissing me passionately to assure me I didn’t have to worry about him falling in love with me either.  And then he rammed his giant cock into my pussy and I whimpered I didn’t give a fuck.

I’m kinda liking these younger men.  I really, really am.

A 40-something single mother who writes honestly about sex, body image, D/s, relationships, her nervous tics, and how much she loves to fucking fuck. She also likes to show you her tits.

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9 thoughts on “I date men that I could have babysitted.
  1. Having been that 29yr old fucking a 38yr old woman I can’t tell you what the attraction is. Maybe it’s the confidence that comes with years, maybe the likelihood that “she” will know exactly what she wants in bed and has every intention of getting it. Maybe the myth that older women who will sleep with younger men are gloriously dirty. I don’t know. But I do know “she” was the best lover I’ve ever had. Hope you can make the most of his youth, energy and enthusiasm.

      1. not for everyone, had so much grief when my friends found out I was dating a 40 year old when I was 30, not many could understand me but didn’t care less anyway. Am off to Berlin this weekend for her 50’s so let’s see what can happen :D

  2. Funny, when I was in my early twenties, I started doing WAY older guys…I’m not sure why. They seemed so grateful. At that time, guys my age seemed like overeager puppies to me. Plus they had no cool furniture.

    Now I am somehow inadvertently married to a man who is 21 years older than me and I would love nothing more than a puppy. Anytime, all the time.

    Our furniture kicks ass though. Great.

    Bisous Hy,

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