A Much Younger Man Offered Me $300 To Have Sex With Him

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A Much Younger Man Offered Me $300 To Have Sex With Him

“I already want to marry you.”

The banter is going well, as well as dating app badinage goes. It’s 11 am, I’m sitting in Irving Farm, here as I am on most days, working on my Vampire Detective novel, and I’m Tinder texting with a 34-year-old mailman who is somewhere in Brooklyn.

You heard me. A hot mailman. That I met on a dating app.

I can count on zero fingers how many men I’ve dated who have worked in post offices. I have simply never met one socially, or in this case, digitally. He has health insurance. He owns his apartment. He owns a car. No kids. He doesn’t care about our age difference. He’s into me.

Did I mention his attractive level is high?​

“Let’s move to text,” one of us suggests. If you know anything about dating apps, moving from app-texting to old-school cellular phone texting is a big deal. It means you have actual access to one another.

With the dating apps, if you don’t feel like talking to someone anymore, you can delete their profile. I sometimes delete my Tinder/Bumble/Please Love Me accounts whenever I am juggling more-than-is-necessary conversations with people; I can’t just delete my phone number. It’s as permanent as my would-be tattoo.

And I like that we’re firing on all cylinders and I’m ready for this to move to the next level of banter.

We’ve established I’m substantially older than he is, which leads to a discussion about babies.

“So you done with babies?” He loves babies. He still eats dinner at his parents' house in Brooklyn. Babies, babies, babies. He’s feeling clucky, I suppose.

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I suggest there are other ways to have a family.

“So you’d be with me and let me get someone else pregnant?” He asks.

And I say, “Yes it’s called surrogacy. Also known as threesomes.

“I like you more and more with every text,” he says.

We’re silly-bantering. He hasn’t gotten annoyingly crass, which happens as well when you meet someone on these dating apps.

Sometimes, a man will come right out and say something charming like, “I like pussy.” When some version of that is unveiled within the first ten dating app texts, I usually “un-match” myself with my almost-boyfriend. We don’t graduate to an exchange of cell phone numbers. He’s proven himself to be someone that doesn’t want a relationship, which is fine, but if I’m not in the mood for it, I am not interested.

But right now? I’m in the mood for this guy. He’s curried my interest and then some.

So, me and the mailman, we’re cruising. We’re flirting. We’re being a little envelope-pushing. We’re having fun. I’m thinking, yeah, I may end up meeting this guy. I will most likely want to sex him up. He’s hot! This might work out. This could be…

So. Sex is on his brain. And not the making love kind. The kind where riding bareback is a goal. Frankly, I’m disappointed. The romantic in me shirks.

I’ve noticed a little bit of assumption on the part of men who want to have their Mrs. Robinson moment: they really believe we are grateful to be having sex with them, these younger men. That we can have unprotected sex because and simply because we can’t get pregnant. That we, who came of age and our sexual empowerment during the era of AIDS, have lost all semblance of our” safe sex” mantra just because we’re old and lonely. That we appreciate any and all semblance of a young hot cock.

And this one? He is aligned with these notions.

“Wait, what?” I text back. He can hear my disappointment through my fingertips.

He backtracks quickly, realizing he may be losing me. I want to work on my Vampire Detective novel, but I have writer’s block. 

This, this feels age-ist. This feels not fun. This makes me feel like not texting. And so, I’m cagey now. Less chatty in the texts.

He tells me it doesn’t feel as nice (what an original sentiment) and he hates them. I have yet to meet a man who enjoys wearing a condom. Says he hates them a few times. I get it, I get it, I get it. He tells me he wants to go out with me, take me to dinner, bring flowers. He tells me I’m sexy. He tells me he wants to have babies with me (this, by the way, is now turning into an inside joke, because of course, we’re not having babies, derrrr.). He’s currying my favor as it were.

“Are you rich?”


“I guess I’ll be the one giving you money then.”

I don’t answer. What is happening here? Has my hot mailman suddenly morphed into Joe Dirt? Did he vote for Trump? Ugh, I can’t bear to ask. I could be working on my Detective Vampire novel. Still. Maybe there’s a way to right this…

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“I really want to have sex with you.” He’s back into having sex with me. But now it’s playful. We return to joking about having sex before marriage. It’s not raunchy. It’s fine. I can do this level of banter. Completely flirty, slightly insincere, totally distracting from the task at hand (Detectives! Vampires!).

And then.

“I would totally give you money if you let me fuck you. You’re gorgeous.”

He backtracks quickly, realizing he may be losing me. I want to work on my Vampire Detective novel; talking to him was a fun distraction but his lack of happily-ever-after is reminding me I have better things to do, like imagine a dialogue where a woman is wooing.

I will give this to him, he knows the difference between “your” and “you’re.” It’s 12:19 in the afternoon. Time for me to eat food, I think. I need to wrap up this conversation.

I decide he’s joking. I reply. “I would totally take your money because I’m an asshole.”

He LOL’s. He gets me. We joke some more about nothing. I ask him a little more about his background, and then he types: “So….”

It’s 12:32 pm. I’m feeling peckish. I’m feeling irritable, but that could either be hunger or the hot mailman. I answer: “Yes?”

“Could I have you over and fuck you for $300?”​

Now I’m wondering if he’s serious. That I could be paid actual cash money for hand-to-hand combat. I mean, sex. It’s so easy to misconstrue inflection in text.

He suggests Facetiming, but alas, I’m in a coffee shop. I don’t feel like talking on the phone either. I don’t know that I want to text anymore as well. I can’t un-match him at this point, not on my cell phone. I can, however, start to work on my Vampire Detective novel. And so, I’m not typing right away. It gets him antsy.

“Just thought if I pay you I won't have to worry about whether or not you’re into me.”

Now. I wonder if the honeymoon is over. If he is in fact, just not right for me. Not even for sex. I wonder again if he voted for Trump. I would put money on it—even though he loves punk—that he’s never heard of Steve Malkmus and Spiral Stairs.

I would bet that 300 dollars he wants to give me to have sex with him that he thinks feminists are a bunch of man-haters.

We text some more, but now I’m slower to reply. I’m seeing him as he is, possibly. And what he is is this: not for me. After a molasses-like twenty minutes, he tells me he has to go do mailman things and there’s no contact for the rest of the afternoon.

Around 5, he pops up again. I’m on the subway, heading home. I decide to play along and reply to his sweet text of, “Hey.” We go back to fun banter. Okay. This is the guy I met at 10 am this morning. Fun and witty. Not crass. Not asking me over and over again if I will give him a blow job (So, what is this? Women he dates don’t do dick?) That I’m older is intoxicating to him.  

I find as I continue to date, that being with an older woman is ideal. To some men, it means no roommates to contend with at her place. To other men, it means a level of experience that’s unparalleled (Really? There are more than six ways to give a blowjob?)

To this man, it means he can live out a fantasy of sorts.

It’s crowded on this train and I’m standing. A few stops in, I finally look away from my iPhone. I look down at the person I am standing directly in front of.

A sleeping, middle-aged mailman. Still in his uniform, in his denim blue pants with the dark blue pinstripe on the side of his leg. Oversized coat. The United States Postal Service patch on his sleeve.

Is this one of those the-universe-is-talking-to me moments? Is it telling me, I’ve met my match and he is a mailman that lives in Brooklyn? Because of course, that’s where the romantic in me goes. Because of course, I’m living a rom-com moment. Because of course, after being single all these years, I might meet my Bashert on a dating app.

What. Is. Happening?​

I put my iPhone in my pocket when I get off the train. Climb the stairwell. Meander for a moment. Then feel the iPhone buzzing away. I pull it out, and there’s a new series of texts, all honing in and around the subject of anal sex. Which, for the record, I shut down hours ago, right before he upped the 300 dollar ante with an offer for 500 dollars if I threw in anal sex. (I explained that anal is boyfriend-material action, and he countered with, “but we’re going to get married.” Which, at the moment, seemed fun and harmless. In retrospect, I see, he was laying the groundwork for some backend material.)

It’s going to be a long night if I don’t shut this avenue down, right now. “Dude. I told you, your idea of a woman my age and what she wants and what she’ll do for a stiff cock is beyond reality. I am not a desperate older woman looking to be validated by a hot young thing.”

There. I said it. I told him to stop acting Trumpian. I feel relieved. I feel like, whoever this guy actually is, he’s just heard me tell him to step off. He’ll course correct or he won’t.

And he says, “I didn’t think you were. And don’t ‘dude’ me ever. I don’t like it. You get to one time. You get the warning. Second time. I’m gone.” He ends his little slap-you-back with a smiley that has a halo emoji.

Fun fact: when someone throws aggressive language around in text, it’s a reminder of what I avoid in real life, people with anger issues. And an ultimatum? Yeah. No. Doesn’t work for me. Ever.

And so this time, I don’t reply. I got my answer. And this guy, he’s not the one.

Not even for a hot mailman with 300 dollars to spare.

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This article was originally published at Barb Magazine. Reprinted with permission from the author.