Take a look at some of the JM production movies. Anal was often a part of those movies and I'm sure there was the odd reluctance theme. Of course if you could find older Marc Dorcel made movies than you find plenty but they may be in French only and they will be hard to find.
I wish you luck with your quest because it will require a lot of research. Edited by - pat362 on 12/21/2016 8:10:40 PM
It falls into the "vintage" category, but the Caught From Behind series is full of scenarios where the woman is uncertain/reluctant/hesitant at first but turns out liking it.
Nice. I'll check it out. Any specific scenes/performers stand out as specifically depicting this scenario? Part of what's hot about anal is it being dirty/taboo and theoretically hard to "obtain." When it's portrayed as just the next logical/presumed step, it's nowhere near as hot as it could be.
^Check out Leah Luv with Jay Ashley in Anal Full Nelson 3. If you join Videobox than you can download that video as well as all of the other in that series. You will also get access to many other JM Production movies that feature anal and should also meet your anti-anal back and forth in the scenario.
^Hopefully my recollection is accurate but I believe they are fooling around and Jay wants to fuck her in the ass and she is quite adamant that this is not on the menu. He goes down on her and the she blows him. They start to have sex and at some point it's in reverse cowgirl and then jay gets her in a headlock and starts to fuck her ass while she keeps complaining that soon transforms into her enjoying it. If you want another one than take a look at Chelsie Rae and Otto Bauer's scene from Dr Probes Lab of Perversion. That one has a lot less anti-anal sentiment but the premise is that Chelsie needs an exam to get a promotion or something and the doctor has her lying down on an examining table and there is a screen so that she can't see what he is doing. There is a lot of anal play where she is not happy before he sticks in dick in her ass and than she is really not happy but as usual she starts to enjoy it,
^Only partially because unlike other videos where the women is adamant that she doesn't want to have anal sex and will play act that she isn't enjoying it. At some point in the scene she relents and starts to enjoy it(at least her character does). It's quite different with LTA because universally the women never seem to enjoy it and too often they look in terrible pain through the anal portion that it makes the scene unwatchable. At least I can't watch it. I'm not into painanal even the fake kind.