I know I am like a kid in a candy store and some stuff I post is probably a nothingburger to others, but just yesterday this young sugar babe I'd visited for the first time on Sunday spontaneously started sending me her nude pics. The funny part was how cautious she was leading up to going behind closed doors. She met me first outside her apartment building. We sat outside on a bench and talked for about 30 minutes. She wanted to make sure I wasn't some form of serial killer (of course nothing she did would have prevented that, but that's beside the point.) She wasn't a sex bomb by any means but a just a big boobed girl next door type -- sweet and innocent. Anyhow she eventually felt comfortable so we went inside for some vanilla sex. But we talked. And as some may have seen in my other posts, I'm into BDSM. So I always sort of mention some slight aspect of it and see how they respond. Well one thing led to another and between talking there and texting afterward, she's looking forward to my next visit where she gets tied up and flogged. I never asked for pics, but when I texted "trick or treat" on Halloween she sent me naked pics in reply. Then I asked if I could do a BDSM photo shoot next time. To which she enthusiastically said yes.
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Now it's not like I talked her into it. She'd revealed some of her past experiences. But my point is that unless I'd probed, I might never have gotten beyond vanilla. I was just patient, understanding, but willing to slowly bring up kinkier activities.
...but I, too, am occasionally surprised by this type of spontaneous behavior from my SB's. I think it's a sign of a few positive aspects of dating in the Sugar Bowl:
1. Treat your SB like your (part-time) girlfriend and she will behave like your (part-time) girlfriend - if - she's into that,
2. But treat her like a part-time pussy for rent and she will act like a part-time pussy for rent.
3. Take the time to have those non-sexual dialogs. My Latina student nurse SB came over to my place to hang during the Halloween candy handouts. We had a fairly intense discussion about the current Mid-east war and related topics. She wanted my help to understand the world geopolitical and related issues from someone with decades more life experience and a lot more international travel time than she has. I am sure she was happy that I treated her ideas and questions respectfully. Then after the last kiddies had come by for their hand full of Rssese's peanut butter cups she took me to the bedroom and we did our own version of "around the world" activities."* Three hours, two showers, and one fresh set of bedsheets later, she kissed me on the cheek and went home.
Her good night text to me when she got home: "Really enjoyed our talk tonight. you gave me somethings (sic) to think about and then you gave me the best dick I've had all year. Good night, Daddy.
Anyway, I never ask for nude pics and I never initiate sext chats. But I still get them and I always express my gratitude for them.
*Around the world: If needed, Google it for escort context of this term. 
Life is good
The Cat
I forgot to mention that while I promised her I'd be out after two hours we spent a third hour afterwards just talking about music and things. I'm 70 and she's 26 and we surprisingly had a lot of old song favorites in common.
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I agree that you can connect with SOME SBs and it's worth the time. But some of them are on the clock as much as any pro. Like the chick I ended up turning down last week who wanted to renegotiate dollars/hours at the last minute. Now she was very hot looking, I can't deny, but that was a cash and carry relationship.
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The chick this week is relatively new in town and from a small town, new to the big city. She might have other friends here but I'm guessing not too many. So maybe she was primed to be more open to a more personal less business like relationship.