Here are my favorite comedy and light hearted damsel scenes from movies and TV, at least the ones I could find on YT.
Hardware – British TV Series
Couple discuss spicing up their sex life. Wife says she wants to be tied up. Husband gets carried away choosing supplies at work.
https://www.youtube.com/watch?v=MkTNWrpZigw
Il Burbero - Debra Feuer (Italian movie, 1986)
Feuer has something a bad guy wants, but she has the wrong suitcase by mistake. When the guy with her suitcase shows up at her hotel room she is tied to a chair and cleave gagged in her underwear. (Great stocking feet close-ups) He inadvertently rescues her from the thug, but unsure of what’s going on is reluctant to release her.
https://www.youtube.com/watch?v=ctIyDWA0dSI
American Dad – The Missing Kink (TV, animated)
Francine discovers she likes being spanked and misbehaves a lot. When Stan finds out he has been duped into engaging in deviant behavior, he puts her on a mule, bound and blindfolded, and takes her to the woods to be banished like the bible told him to.
https://www.youtube.com/watch?v=I-UqdieAP-0
I Cover the Waterfront – Claudette Colbert (movie, 1933)
Made before government censorship allowed a woman to be tied up but can’t appear to enjoy it, because that’s immoral (see American Dad). Claudette is on a tour of a slave ship turned museum with a reporter. He locks her into a standing cross as a demonstration, then begins to steal kisses, and she begins to fall for him.
https://www.youtube.com/watch?v=Dt0AkUqMc70
Venture Bros. – Princess Tiny Feet (TV, animated)
Late night cartoon on Adult Swim. Bondage, ball gags, and a kinky Indian Princess.
https://www.youtube.com/watch?v=biu5cSmgDLg
Goin’ South – Mary Steenburgen (movie, 1978)
In this western set in the late 1800’s it’s a hate-hate relationship between Steenburgen and Jack Nicholson until he ties her spread-eagle to her bed. The sex is implied, (that pesky censorship again) but her complete change in attitude suggests she enjoyed it.
https://www.youtube.com/watch?v=b5k_eroOeJM
Labor Day – Kate Winslet (movie, 2013)
Winslet is tied to a chair by a fugitive Josh Brolin in a very erotic and caring way, (50 Shades could have taken a lesson from this) then he feeds her in the same way. There is no sex, real or implied, and by the end of the film she is totally in love with Josh.
https://www.youtube.com/watch?v=gyGv9-Iw_fs
Weeds – Kat Foster (Showtime series)
Kat is ball gagged and strapped to a spanking bench in leather underwear for some kinky fun with her partner. He pulls the gag out for some intimate conversation, but re-gags her to take a phone call from their business partner. She tries but fails to influence the conversation.
https://www.youtube.com/watch?v=-AfeHAeq9BQ
And some honorable mentions if you ever happen to see them:
Doctor’s Diary – German ER knock-off, at the beginning of the episode a male doctor enters the morgue and notices one pair of feet in the row of corpses with no toe tag. He pulls back the sheet to find a female doctor gagged and tied to the gurney, presumably the aftermath of some kinky fun. She has a penis drawn on her face pointed at her mouth which grosses him out so he removes the gag with a forceps.
Man from U. N. C. L. E. – The Pop Art Affair. When Illian finds a girl tied to a chair, he says “you weren’t gagged, why didn’t you call out.” She responds “I’ve never been tied up before, I think a girl should experience everything at least once.”