Disclaimer: I own none of these characters, or Marvel, or a Stark Tablet (which is probably really fancy and awesome). This is my first ever fanfic, so please be kind!
One of Tony Stark's greatest joys in life was taunting Captain Goody-Two-Shoes about his amazing lack of, shall we say, fondue. One particular morning-a morning where Tony possibly consumes more coffee than anything else, but hey, he was inventing things-Steve actually talks back.
"I'm pretty sure I'm not a virgin." Steve casually says, browsing the day's newspaper.
Tony raises an eyebrow. "You're pretty sure? You do know that Eskimo Kisses don't count, right?" Pepper, who is already tapping away at a Stark Tablet, rolls her eyes.
Steve doesn't look up. "Blowjobs count, yes?"
Tony Stark, billionaire playboy who thought he'd heard it all, chokes on his coffee. "You...what? How do you even-"
"I looked it up."
"You looked it up?"
"Jesus Christ." Pepper also seems surprised, though she hides it carefully behind a well-practiced poker face.
Carol strolls in just then, her hair already made perfect by her control of molecules. Today, her ever-changing 'do is short and spiked up in the back. It's a good look for her, Tony decides.
"What are we talking about?" she asks.
"Capsicle had a blowjob." Stark points an accusing finger at Steve and pouts. "This whole time he's been lying to me."
"I haven't been lying to you, I think I have the right to-"
"Doesn't really surprise me, to be honest. " Carol interjects, scarfing down a power bar. "I mean, the guy was in the Army. And then there's the whole amazing-abs-in-a-skin-tight-suit thing."
Tony gasps. "Holy shit, I totally didn't think of that. Was it a chorus girl? Was it? Did you get a blowjob from a CHORUS GIRL?"
Pepper glances up from her work, gives Steve a sympathetic look, then punches Tony in the arm.
"Ow! What was that for?"
"You know what."
Despite intense pleading from both Carol and Tony, Steve doesn't say another word about the mysterious woman who took his virginity. Clint, after he finds out, spends the next few weeks pointing at random women and asking "Is that what she looked like?" They find out nothing. Not a name, a distinguishing feature, nothing.
It isn't until Bucky comes back from the Russian dead, and moves in with Steve, that Tony finally understands.