I've been hobbying for 10 years and I am approaching my 70's.  
I find now that companionship or the time leading up to the sex has become more important to me. It's been a while since I've had msog in 1 session.
So, I try to indulge in the fantasy of a role play. For example, I like variations on the boss/employee theme.

Definitely boss/secretary or hottie co-worker

Most all of my appointments are roplay so I've done quite a few scenarios... I'm partial to dr/patient roleplay personally...  

I have only done it once.  My "boss" was mad that I had my eye on another women so she ordered me to have revenge sex with herself.  

Fairly recently the role play topic came up in conversation when I was with a provider I've seen for a long time. We'd never done a role play together but she brought up scenarios she's done with others, including step fantasies. She said she liked the taboo of that type of fantasy. We ended up trying a step scenario. Found it to be a lot of fun. Probably something I'll try again with her and others that are ok with it. Its definitely not for everybody though.

The doctor/patient is my favorite. It's the control, and the undue taking advantage of my "patient" as it were that is a real turn on for me. Taking time with the girls to slowly get into things seems to be an enjoyment for them as well. I would love to find a provider who shares my enthusiasm for this roleplay.

We have had a number of role play requests, and honestly all of them have been fun to some extent. The mother-daughter ones can be fun (consider it some intimacy mentoring), but I think our favorite is one where the client comes over and tells me (Tori) that Nick lost a lot of money in the neighborhood poker game. Unfortunately, we can't afford to pay it off so Nick has offered for me to work it off. I am very shy and haven't had much experience so this comes as a shock. Part of the settlement is that Nick has to watch and then perform. You can figure it out from there (I am angry at first but then really get into it). It is really fun to get into character and we have actually done this a couple of times--each better than the last.

What do you think about "wedding night" dress up / role play?  I have wanted to try this one for a long time, but not sure how to ask a provider or if they would think it is weird.   What I had in mind was asking the provider to wear a sexy set of all-white lingerie (white bra/corset, thong, garter), white thi-highs, white heels, and to top it off, perhaps a tiara or veil???  Someone else above mentioned costume jewelry, which I had not thought of, but I guess a fake ring would add to the role-play!   I would provide the outfit if she doesn't have all this in White.  

The guy asked a girl to lay in a tub full of ice-cold water as long as she could, then pretend she was dead while he did her.  

Good one.

I was looking for new ideas, inspiration so to speak.
But this idea is a buzz kill.  
To each his own.

... And, I just got some new role play outfits! AND, I found an awesome costume store right down the street. I just got a sexy stewardess, Rock a Billy girl, Alice in Wonderland, and for those really naughty, a nun.  

I'm a role-play virgin but I've been thinking about that with a threeway. I'm having "fun" with a women and suddenly my jealous girlfriend walks in on us. She's not sure who to be more pissed at so she challenges the girl to see whos better at various sexcapades with me. They get a little pushy with each other. Then they both suddenly realize they're really pissed at me so they become insistent on me taking orders and serving them. Interesting?

Would I refer to you as Sister Jamie or Sister Solo?

ok i am embarrassed to admit this but ....   one girl i was with .. maybe our 3rd or 4th time ..   while having sex she starts crying like a little girl ... saying no .. stop .. please no ..   (of course this was all for effect)  which only made me start fucking even harder without me even thinking about it ..    i have to admit it was a real turn on .. i was really surprised.     not something for all the time but as a change of pace.    

I love them.  One reason I like them is it helps make the date memorable.     Recently did one where I told a partner that she lost a bet to one of her girlfriends.   Losing the wager would mean she would have to fuck in front of a room full of her girlfriends.  With great enthusiasm I told her what her friends were saying while we were fucking.  It was Much hotter than I can describe in a post.  

I like it.  

I’ve done a few different scenarios with ladies I had seen a couple times before.  I think of them as a fun ice breaker - not something that lasts the entire date. Too much pressure  to stay in the role makes it too much work.

Reviving this roleplay thread, since Halloween is right around the corner!!  I noticed that luxury lingerie shop Honey Birdette has this exquisite Bridal lingerie set, complete with stockings and a veil.  Now this is exactly what I had in mind to ask a provider to wear for sexy roleplay.    Ladies , what do you think, would you wear this for roleplay or is it asking too much??  Or guys, have any you tried asking the ladies for something like this??

Maybe this is simple but I always want to be seduced/picked up anonymously.  Like I am sitting and working in a Starbucks and someone comes over and convinces me to leave with her.  It took forever to convince anyone to arrange it for me but it was great.  Now I want to do it with 2 girls like maybe lesbians but they are looking to throw a guy into the mix once in a while.  The best part is I have no idea what they look like or who to expect.  I gave up trying for this second scenario for a while but maybe again one day...

One I have had fun with a couple of my SW friends is one where we engage in passionate sex after tearing each other's clothes off. I buy the dress and ship it to them in advance of the meet. Just the excitement of waiting for the date adds more to the scene. Have had a couple of times where I needed to leave with the zip of my trousers broken 😉.