If by generous you mean tips or gifts, bear in mind that you can always refuse them. I think if your spidey senses are tingling you need to make sure appropriate boundaries are in place.

Generosity can be a sign however not always, I've plenty of clients who have tipped or given presents without ever pushing any boundaries whatsoever.

For a few years a bad experience with a couple of clients did lead me to believe presents were a sign of boundary pushing, as a result I used to get really uptight if anyone brought me presents - really got my back up if someone did. Over time however and with proper reflection I realised actual presents don't mean anyone is going to be difficult. It's their behaviour, the way they act which determines boundary pushing.

DEFIANTELY their behaviour and the way they act with you determines boundary pushing.
Sometimes little presents and tips are their generous nature, but the ones that overwhelm you in a negative way need to be dumped and blocked. I would also add that the ones that overwhelm you usually have problems in relationships with women - just my observation and experience

With clients and life in general I think it's good to be wary of overly generous people. Not that they are all wronguns, but there are definitely some who will tally up what they've given you and then throw it back in your face, or make out that you now owe them something because of it. A gift should always be given freely, but some people give gifts don't see it like that.

I agree. I have a long term regular who has bought me quite expensive xmas gifts in the past and has subsequently referred to them in bookings. I honestly have gone off him in a massive way. That’s another story.

My regular despite me being sick after xmas two years back ( he knew this) kept pursuing me (after gifting me) for a NSA dinner date!!!!

Personally I think sometimes certain clients think they ‘own’ you once giving an expensive gift

I find ones who give non money gifts are lovely.

I love chocolates and other things
One guy bought me fresh eggs laid that morning.
I made sure when returning to his area I have an apartment with a kitchen booked so I can have fresh boiled eggs mmmmmm

Others have given money tips and left on time.

Its the ones who give the hours fee and something extra for you dear (£20 £30 £50 ) so we can have a REALLY good time or say so I can maybe stay a little longer.

Pay the fee  dont pretend to be generous when what you are doing is trying to get cheap extra time.

All in I would say if your spidery senses are tinging trust them.

If it is not a location he can easily find you in or trace you maybe stay with him if he is not pushing too heavily?

You can take more small risks on tour then you can from a working apartment or your home.

Oh yes, the ones that pay for an hour, give you a gift and expect you to stay 2 hours!

Bit off topic, but does anyone else receive nice gifts that you know you will never use and give it to friends/family as "your" gift to them? I often save a fortune on Christmas shopping by doing this!!!
I like to call it being thrifty!

Gifts I like, and I've never had anything expensive enough to worry me. Chanel Perfume probably the most pricey thing I've received. But perhaps he is displaying other little signals on top of gift buying/ general generosity that you are picking up on?

The worst ones are the ones that say "Hay and if you give me a good time, maybe I'll give you a nice tip/maybe I'll be a good regular!'. How self important do you need to be...

I rarely get given anything at all.  I am lucky to get so much as a tenner tip.  This region where I live is exceedingly tight.

I was once given a home made candle it looked awful something you could pick up for 25 pence in a car boot.  I threw it in the bin!

If you aren't comfortable with the guy then just don't see him.  Or see him for shorter bookings you can always say you are fully booked etc.

I've only had one guy be manipulative with a tip.He had booked in for a sploshing session and arrived early.By early I mean like 10 minutes.I was almost ready but not quite so I told him I'd ring him back in five minutes.I duly did and he had taken it upon himself to go get a drink at a pub!So in the end he arrived late for his booking and then clearly expected his full time.He then paid me and had slipped in an extra twenty and said it was so we could have a little extra time and we didn't have to rush.
He had already got my back up and so I gave him the 20 back and said we would be finishing at the previously agreed time as I would have to clean up after him and then I would be going home as planned.He really was a prat and commented later in the booking that he thought I would be really into sploshing like him and that he was sure I would have had an orgasm from all the custard and cream being rubbed on me.Whilst I don't mind sploshing and will enthusiastically go along with it why the fuck would being smeared with food items actually make me cum?It's his fetish not mine!Deluded!
I think you need to see some proof of boundary pushing though before assuming,if they then start hinting at something or directly pushing boundaries then you need to refuse further gifts or decline to see them again.