Humerotica
He Wanted Anal Sex on our First Date
Jackpot!
I never thought I would meet a guy who wanted to get pegged on the first date.
Normally it takes months of assuring him of his manhood before he even lets you slide in a finger let alone a cucumber sized strap on.
Anyhow, we were making out in the bed and he announced, “I want anal!”
“Sure thing!” I said happily. “Be right back.”
So I went into my walk-in closet and got my stuff, my dom lingerie and strapped on my strap on. I wondered if he wanted to be tied up too. Wasn’t sure, so I grabbed the handcuffs, the ball-gag, and the cock ring.
I came out of the closet with my gear, and he said, “What the fuck?”
“I thought you said you wanted anal,” I explained. “Do you not want to be pegged?”
“Pegged?”
He didn’t even know what that meant. Awkward…
“Oh,” I said, turning red. “You meant you wanted to give me anal.”
“Of course,” he said. “I’m not gonna let you put that thing in me. No way.”
He was eyeing the big black strap-on dong dangling between my thighs. Methinks the man was protesting too much, to be quite honest. They always make a big noise about it beforehand. I’ve been there. But it’s nothing compared to the big noise they make during, with a dick up their ass for the first time. They universally love it, so I don’t know why they have these crazy ideas about it being less-than-manly to take eight inches of hard plastic up the bum. As far as I can see there is nothing more manly than that. You have to be brave, strong and heroic — all very macho traits. Most of all, you have to be very comfortable with your masculinity.
“What’s the matter?” I said. “Are you not comfortable enough with your masculinity to try something like this?”
That always gets ’em. Every man pretends that he’s comfortable with his masculinity, see. It’s part of being a man, even though no man really is comfortable with it. How could he be comfortable with his masculinity when he’s half the size of Duane Johnson, his dick is three inches shorter than the average porn guy’s, and he is starting to develop man boobs, thanks to his love of hot chicken and his iffy relationship with jogging? What, ladies, am I describing your man? Then yes, he’s going to need a little convincing if you want to try this trick with him. But trust me, he’ll thank you for it afterward.
How could a man be comfortable with something it’s impossible to be comfortable with?
It’s true. You think the standards of beauty and virtue are high for women, think about the standards that we have in our society for what makes a man a real man.
- A blue-collar job. A guy who works with his hands. Not some schmuck who sits in an office all day getting soft. Thing is, your guy probably has a white-collar job. But not enough of a white-collar job to feel manly. See the next item.
- A billion dollars. Yes, that’s what it takes nowadays and our great leader has proven that even that is not enough to make a man less insecure. Guys like Mark Cuban and the newly buff Jeff Bezos are real men. Your boyfriend is not one of them.
- An enormous schlong. Most men I’ve met don’t have an enormous schlong. And the ones that do are no fun to be around because — newsflash — an enormous schlong doesn’t fit in a pussy. It hurts like hell. So there again, there’s no way he feels like a man down there.
- Guns. Either strong biceps or actual guns. Most guys I meet in Los Angeles are big believers in gun control and don’t seem to do many pushups. So, it’s not likely that they feel too manly. They probably feel like the wimps that they really are.
And here is the secret to getting them to understand the beauty of pegging:
“Don’t be such a wimp!”
They’ve been hearing that lovely phrase all their lives, no doubt. First, it came from their dads, when they were crying on the first day of school. “Don’t be such a wimp.” Then it came from their middle school friends when they were hesitating before the twenty-foot cliff dive. “Don’t be such a wimp!” That’s what they heard right before they broke their necks.
“Don’t be such a wimp!”
They heard that before taking another shot of whiskey — the one that made them barf, blackout, and bare-ass nakedly run through the streets until finally, thank God, some red flashing lights came to the rescue and threw their naked ass in jail.
“Don’t be such a wimp!” their buddies said before they skied down that black diamond straight into a body cast.
“Don’t be such a wimp!” the dentist said when they begged for more Novocain.
See, they’ve been pretty well-trained for this moment. You just kind of need to step right into it, like a custom-made suit. Men don’t want to be wimps, they want to be men. And it means getting pegged in the ass to prove it, gosh darn it, they’ll bend over and smile.
“Don’t be such a wimp,” I said to my new friend. “I promise I’ll be gentle, you big baby.”
“You promise?” he asked. I nodded. And he gave his consent.
So he got on all fours and I lubed him up real good. Slowly I inched it in. Sure enough, he started making a helluva lot of noise, most of it sounding pretty pleasurable. Soon I was all the way in him, and pounding him into ecstasy.
And I was so happy because I like to make other people happy. That’s right, I’m a people pleaser. I reached around and gave him a little help. It didn’t take long, with that pressure on his prostate. In a second he was cumming like he’d probably never cum before in his life, making a total mess of my sheets. I mean there was a puddle of white stuff pooling there — if that’s not manly, I don’t know what is.
“Anal sex on the first date,” I said to myself as he screamed in ecstasy. “This guy might be a keeper!”
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