I was already married, almost a middle age man when first time had sex with a squirting lady.
They were a married couple, interested in a man who would love to do oral for her and would do everything enthusiastically regardless of heavy squirting. Another caveat was that he would be right there, may be also nude and that this should not be a problem. They also wanted somebody nearby, in the same city.
A nude husband certainly would not be a problem to me, - if they'd like I would suck his cock... but I decided not to overdo things and contacted them very modestly - that yes, I live in the same city, and I also have to be discreet ("even more discreet than you - because you are in this together but my wife does not know"). And yes, squirting is totally fine, and husband being right there is absolutely fine.
Again, I had never had a sex with a squirting lady but I always loved feeling wet and naughty, smeared with woman or man cum and saliva, or with a food play - so I thought that squirting is a big plus rather than minus.
I did not have much hope of course because any couple can find many willing males. But they have responded, actually she has responded, and, strangely enough, she also warned me that she is on a 'plump side' - like if this would be a problem! For me this was again more like a big plus, but again I did not went into much wording in my messages. I just suggested that I can come to meet them, and they decide... if they decide 'no' then we just forget the whole thing.
A few more messages and soon I parked near their home, - turns out I could have even walked there - just three blocks away from my home! She opened the door, looked me over and said "wow, wow". This was Summer, hot day, I was dressed for the beach (official version: "tired from work, going to run and swim"). I have athletic body now, and I certainly had it not less athletic then. The lady was looking very good, and I was surprised when she rubbed her hips with her hands and said "well, I warned you I am on a plump side..." I absolutely sincerely told her that she looks great and that I love curves.
We entered. Her husband was a stocky solid man at the kitchen bar, with wine for us all. He got behind her then and opened her left breast (I remember this well) and asked if I want to touch it. She was much lower height then me (he was a little lower too), I bended a little and kissed... but again - like in all these messages - acted modestly and without my own initiative.
- Do you want to suck it a little? - She asked. I sucked, licked, sucked again, she moaned, he rubbed her back... Then she suggested to go upstairs.
She showed that under bed sheets there was a blanket, and under the blanket there was a plastic sheet - so that squirting would not spoil the bed. Then she mentioned again that the husband may want later to also get nude and hopefully this is not a problem (I smiled in my thoughts - and then very fast she just got on the bed on all fours and stuck her big round ass upward and said "so..."
She had now only lingerie and no any panties. I tenderly groped her ass cheeks, put for a few seconds my palm between them, - but then just got comfortably behind her and started to lick her pussy and all around, my nose is gliding between her cheeks and sometimes touching her ass hole. My face was soon completely wet... the butt moved back and force, and I do not see much out of the butt, only sometimes lady's back. Then I started trying to push my tongue to her pussy and far as possible... I moaned a little too.