Reddit masseur
I connected with this guy on Reddit in NorCal. We lost contact and I am bummed, but I have to share this experience.
He was offering free massages at his place and I reached out. I am more curious but really love the sensation of prostate massage. I (taller athletic build) went to his place. He was an older salt and pepper daddy type and really nice. After we greeted each other he led me downstairs to a den area with a couch and massage table in the middle of the room with some light music already playing. I was slightly nervous at first being led into a basement with a stranger, but when we got down there he eased my nerves with a big hug. I returned the embrace and I could feel him start to press his hips into mine and I could feel his hard cock through his shorts starting to swipe against my growing erection.
This was the first time I felt myself getting turned on while hugging another guy. He asked me to turn around and then started massaging my shoulders while keeping his hips pressed into my backside. He then made his way from my shoulders to my biceps, to my chest and then finally worked his way past my abs. He then gently grabbed my hard dick that was at full attention through my shorts.
"Are you ready for the massage?" he whispered in my ear while slowly stroking my dick through my shorts.
"Absolutely," I replied.
I took off all my clothes and laid down on the table face down. He then started giving me a great massage working on my upper body. He then would slowly work his way down and start to tease my hole. He would slide his forearm between my cheeks and graze my cock with his hand. He made a few more passes like that before he started to move down and work on my legs. As he rotated to start working on my lower body I heard a slight rustling but didn't think much of it. He started working on my right leg starting at my calf, moving up to my hamstring, and then getting to my glute.
When he got to my glute I could feel his exposed cock slide across my hand as he spread my cheeks apart to play with my hole. He lubed his hand up and slowly started circling my hole with his finger while I started to grip his cock in my hand. I don't play with my hole at all so it was really tight as he slowly started to work his finger inside me. He took his time easing in slowly working deeper. He then switched sides and proceeded to work on my left side. Once he got to my hole this time he was able to slide his finger in much easier and it felt so good. He slowly worked my hole deeper this time while I started to stroke his cock. he then switched from his finger to pressing his thumb inside me which felt so much thicker inside my tight hole.
It hurt a little bit and took some getting used to as he slowly stroked his thumb inside me deeper and deeper.
"does this feel good" he asked
"yes" I slightly whimpered.
He then asked me to turn over and I could see him rock hard with a cockring on. He then grabbed one of my legs and held it out to the side stretching my hamstring. As he started to give it a deeper stretch he started fondling my balls and then slid his finger back into my hole. the deeper he stretched my leg, the further he pressed his finger in my hole. I felt exposed and vulnerable but so turned on at the same time. After he stretched the other side he then asked me to hold both of my legs open and he slid his thumb back in my ass and started stroking my cock. This combination sent me over the edge and I came harder than I ever have. kept milking me until I was finished and then he started stroking his cock until he came.
He went and got a rag so I could clean up and get dressed again. I met up with him a couple more times but I never actually got his number only through Reddit. If you are in NorCal and provide massages hit me up haha I need to experience again.