Here’s one
[QUOTE=Steve Tyler (and then Run-DMC)]
High school loser, never made it with a lady…
Then my next door neighbor had a daughter with a favor
[/QUOTE]
At least twice as icky as it’s prequel Young Girl, which is saying a lot. But a nitpick- it isn’t about a guy getting “boned” for the first time, it’s a paternalistic creep telling us about having bestowed (or inflicted) his bone upon a possibly underage virgin.
It doesn’t explicitly say it’s his first time, but Confederate Railroad’s “Queen of Memphis” includes the line, A boy became a man that night in the arms of the Memphis Queen.
Any of GPUG’s songs are the ickiest songs ever. And I thought so at 16 when I was the archetypal horny teen boy.
Edit: What kunilou said.
Huh? 
Which also brings Night Ranger’s “When You Close Your Eyes” to mind.
“I remember we learned about love in the back of a Chevrolet…”
Starbuck’s Moonlight Feels Right seems to fit the bill; it might be his first time, hard to tell:
The wind blew some luck in my direction
I caught it in my hands today
I finally made a tricky french connection
You winked and gave me your o.k. …
Mystery Dance by Elvis Costello.
Night Moves, Bob Seger
Seems like a Chevy was the vehicle to have; no wonder I couldn’t get laid.
Another Harry Chapin song, “Taxi”, has the line, “We learned about love in the back of the Dodge”. So you had more than one option. You weren’t a – gasp! – Ford man, were you?
More from the woman’s POV:
He walked right up and told me that he liked my style,
I noticed something different in the way he smiled.
He said, “You’re quite a lady,
And I know a place that’s shady,
Would you care to come and lie with me a while?”
And deep in my soul, I could feel a quiver
When he went down and found that sweet old river,[sup]*[/sup]
And he showed me the way to find
Love in the afternoon.
– Evie Sands Love in the Afternoon
You know you used to drive me crazy
In the back of your Chevrolet.
And every Friday night, if you were feelin’ right,
You’d take a girl all the way.
You had a terrible reputation,
The one and only 4F kid.
They threw you out of school for breakin’ every rule,
But the one good thing you did:
You brought the woman out of me.
You taught me everything I’ll ever need to know.
You left a mark upon my life,
And I can never pay you back the debt I owe,
You brought the woman out of me.
– Evie Sands You brought the woman out of me
[sup]*[/sup]Yes, that means what you think it means. Thanks, Evie!
I drove a 1960 Rambler. 
Here’s another one about a guy’s first time. Lou Christie’s Rhapsody in the Rain.
You probably haven’t heard it because few radio stations would play it, thanks to lyrics like this
The guy got laid, then dumped.
We know all about those Ramblers!
Another possible woman’s view, sorta: Will You Still Love Me Tomorrow.
Mrs. Henry. Cheap Trick. - YouTube
Stop that thief. Cheap Trick. Cheap Trick - Stop That Thief (Previously unreleased in the U S ) - YouTube
Thanks for the suggestions. I thought of “Paradise By The Dashboard Light”, but most of these are new to me.
My first car was a 1967 Rambler! The four door American. Man, I loved that car.
Never got laid in it, though. Shoulda went for a Chevy I guess.
Wonder who’s first time it is here…
Benny or her?