1. It’s a novelty. As George Mallory said when asked why he wanted to climb Everest: “because it’s there.” If you’re searching for deeper meaning into why a guy wants to put his penis between your breasts, you’re just wasting energy. He likes putting his penis in/on/between/neat things and he likes your breasts. There’s no “what is the sound of one hand clapping?” shit going on here. This is just a guy taking two of his favorite things in the world and quite literally mashing them together.
2. He’s a little bit worried about basically rubbing his bare butt against your sternum. There are two standard ways to perform the ol’ TF (my not-so-secret, less gross term for "titty-fucking"), and one of them comes with a host of logistical issues. If he’s seated and you’re between his legs, there’s not much for him to worry about. But if you’re lying on your back and he’s straddling you, he has to make a few decisions. Is he going to park his sweaty ass on your stomach while this all goes down? Is he going to awkwardly hover inches above you while his hamstrings cry out for mercy? He better hope his butt is clean.
3. He’s sorry for inadvertently jabbing you in the neck with his penis. He really doesn’t mean to, it’s just that he’s very enthusiastic about the whole thing.
4. This is the cilantro of sex acts. It’s cool that cilantro is there on the plate, but you probably wouldn’t miss it if you got a steak with no garnish. Cilantro is nice, but it isn’t filling. Also, some people hate cilantro!
5. You will not hurt his penis if you squeeze your boobs together. You really can’t go too tight here. Your breasts are soft pillows. You’re not going to hurt his dick. But we appreciate you caring!
6. There’s virtually no such thing as too small. Again, it’s likely all about the novelty to him, not the size-to-penis-engulfment ratio. Don’t sweat it.
7. If you’re using this as the finisher, it positions him to ejaculate on your breasts. It’s not a requirement and you’re not at all obligated. It’s like that "do you want to make a $1 donation?" message that comes up when you swipe your debit card at the register. So if that's not a fund you want to contribute to, let him know ASAP so he has ample time to figure out a plan B. It can be a difficult position to maneuver out of physically, so the more notice the better.
8. He is *terrified* of getting it on your face or in your eye. He will never be more fixated on "aim" in any other sexual act, ever.
9. He would really love to touch your boobs more. He'd really like to touch them while he slides his penis in and out like a hot dog sliding in and out of a bun over and over. Which isn’t something a hot dog typically does, so this metaphor falls apart quickly. Which is a shame, because I had an entire paragraph ready to go about how semen is kinda like mustard.
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