i would help my naive little coworker out. first, there'd be none of this "but..but.. you're his girlfriend..." she'd get exactly what she asked for (and a lot more) and i'd get pictures (video if she lets me, and she probably will). then i'd show poor jerry and say "your girlfriend's a slut, so i did you a favor. now you can get the upper hand and dump her." and if he's a friend worth keeping, he'll get over it.
friends don't let friends get strung along for weeks or months by sluts. the author never learned this, but the manager, chuck, did.
oh, and pics or it didn't happen. it's sad when a code geek turns to harlequin fantasies to prop up his need to feel wanted.