Getting off with an older woman [MF]

At the age of around 25, I’ve always been told I am good looking, and have had mixed results with girls over the years. At this time I had a serious long distance girlfriend, and sometimes satisfied my need to feel desired or for quirky sexual fulfilment on the quiet. Through fear of diseases like herpes or HPV I always largely kept these interactions to foreplay only. Luckily I have a ‘thing’ for lubed handjobs.

I had downloaded tinder, and maybe for the fear of rejection, tended to strike conversations either women that you could say were ‘below my league’ for want of a better phrase. I never met with any of them, apart from one. I’d chatted to a few older women, but one of them seemed lonely, not very confident and we chatted lightly sexual. She had dark hair, was slightly overweight and the last person anyone would expect me to be looking to hook up with. She explained she had a few young men bail on her at the last minute, it was all just words and they never carried through.

My secret [MM] erotic massage arrangement.

Firstly, I am a taken man and straight. I came across this situation looking on Craigslist. Put simply, like a lot of guys I love and well lubricated handjob and have twice before visited women who do it as a service. For some reason, maybe out of curiosity or maybe out of being cheap and wanting a freebie, I visited this guy who is a professional sports masseuse.

As I say in the title, I usually go round and have slightly awkward chat for a minute. I go and have a quick cleanup and come back in naked. It kind of feels nice to be desired in the same way I guess women feel by men? Obviously the guy is gay. He then proceeds to just enjoy my body whilst I lay on the table. I try and imagine what a great setup this would be if I mirrored the gender roles a bit. For this guy it’s kind of equivalent of being a straight 50 year old guy and having hot girls from 24-40 come round and let you play with them to your hearts desire.