Ill try to make this short, but i have so many thoughts.

A far cry from all the 18f posts in here, but its a true potential happening. Ive known this woman for about 30 years. She is like a 2nd mom, but its been some years since we connected. I’ve always had a thing for her and her shape, shes got a massive natural rack and this cute little beauty mark on her lip that always sparked my fancy.

Extra context, ive been friends with her son for the same period of time. He hooked up with a super fresh ex of mine behind my back for a couple of months, but we still remained friends even though it crushed me that he went behind my back. So this would be a double fulfillment of lust and revenge. I also kinda feel like she may be open to getting laid as well.

I live in a high tourist area and we just reconnected so she learned i live there. She gets comped hotels and resorts food and all this. So she planned a trip and said i could crash in the suite or in the adjoining room 👀 she wants to hang out have dinner and drinks 👀 and such.

Her husband passed about a decade ago and they divorced before that. She most likely found out he was cheating. Myself and friends had personally witnessed him drop off prostitutes a couple times. So that could have been the cause.

She has always been a kiss on the lips type of person, which i have big full ones. I used to give her massages when she was sitting in chairs, but also other friends or parents. She likes to drink and after all the offers of crashing over, food and drinks, its like a date weekend is being set 👀 shes kinda boisterous and fun, so im thinking theres a good chance of drunken massage and closeness.

In all sincerity i do want to hang out and have fun. But I can’t lie and say that if she tests the boundaries that i wont help make her trip EXTRA fulfilling. What do you guys think?