Happy Ending ;-)
I was in my late 20's and I found this woman online who offers massages out of her home. She was in her 50's. She was a legitimate therapist who worked out of her home office. She was nice, clean and her house was in a very nice neighborhood. I started going regularly for about a year.
Anyway, one scheduled visit I decided to test the waters. Prior to my appt I had shaven my balls, ass and the area in between. When she gave me the usual 10-15 mins to undress, lay on the table and relax, I positioned the towel high enough that it covered my butt but low enough where you saw the goods. I felt it was subtle enough to be a honest mistake so she wouldn't get offended.
When she walked into the room she asked in a flirtatious rhetorical tone "I see we got very comfortable today, anything bothering you in particular?" I replied no and the session started. When she started with my back she positioned the towel low enough where my butt was exposed. It was excited but nothing unusual. I noticed when she rubbed my lower back she was rubbing my butt cheeks though. When she got to my legs, she positioned the towel high on my back so that my butt was exposed. Now I'm excited and nervous! While she was massaging my legs she "accidentally" rubbed against my balls and she said "sorry about that" I then flirtatiously said "oh its completely fine" She kept rubbing legs and bumping into them. She then warmed up coconut oil and slowly put her finger in my ass. After a few minutes I was on my elbow and knees and she was fingering my ass while tugging on my cock. She was slowly whispering "Cum for mommy, its ok baby" . I couldn't believe it!
I flip over and Im now laying on my back with a raging erection. She proceeded to warm up more oil and take off her shirt and bra! For a woman in her 50's she had BEAUTIFUL tits. She started stroking my cock with one hand while fingering my ass with her other hand. I exploded all over the place. She then warmed up towels and rubbed me clean. She told me it was her first time she's ever done that. I don't know if thats true or not but it was extremely wild.
We spoke afterwards and said she was in a deadend marriage and this whole experience was her a huge turn on for her and fantasy fulfillment. I asked "you've never been asked to do this" and she said "when guys ask me for extra, I get mad and refuse" However she told me she had a fantasy of a younger man doing exactly what I did! She wanted a younger man who was clean shaven to slightly hint at wanted more without asking. She wanted the body language to do the talking and I provided that. It was surreal. Needless to say I still go regularly.