I found myself in San Diego one weekend a few years ago on a discounted weekend getaway and was feeling up for some play.
A Grindr hookup the first night with a chubby young bottom was nice. But being a versatile guy, I never turn down an opportunity to bottom myself. After checking out the sites, I found something up my alley.
I noticed an ad in a gay directory I had from a guy in his late forties offering a massage/prostate massage. Prostate massage is nice when you find someone who is good at it and knows how to do it right and my first boyfriend was excellent at the prostate massage/blowjob combo. Some men I’ve been with have warmed me up with a brief prostate massage and there have been some when I’ve wanted to say, “Keep going!”
I called the guy up, who introduced himself to me as “Steve,” and he told me he did a forty-five-minute massage first, followed by the prostate massage. He said it would be a two-hour appointment and run me about $200. I said, “Well, it’s a little steep, but I haven’t had a massage in a while and this sounds interesting.” He promised me a “relaxed and intense session.” He told me he only did incall and gave me an address, told me to cleanse myself out first and he’d see me at the agreed time.
After my cleansing ritual and a shower, I hopped in an Uber that took me to the small house just outside of the city. I rang the doorbell and Steve greeted me, dressed in a pair of jeans and a tight black shirt showing a somewhat athletic figure. He gave me a bottle of water and told me to hydrate myself a little as we walked into a room with his massage table that was all prepared. He told me to undress, lay flat on the table and he’d be right with me.
A few minutes later, the door opened and shut behind me, my face looking down at the carpet through the hole on the table. Some new age music started, and I pulled my face out to look and noticed his completely naked muscular physique, a long cut cock dangling between his legs. I put my face back down and felt the oil drip on my naked body and his hands start rubbing me down.
I lost track of time and drifted away as he massaged my naked body with his heavenly hands, which massaged my calf muscles, my thighs, my ass cheeks, lower back, shoulders, arms, and hands. He told, “Go ahead and turn over,” and dripped oil all over my front side and started to rub me all over, his hands sometimes rubbing over my flaccid cock that I felt too relaxed to stand erect. After massaging my feet and ankles and upper chest muscles, he patted me and told me he’d be right back and to just relax for a couple of minutes and handed me the bottle of water.
He came back with a box of latex gloves and a bottle of Gun Oil lube asking me, “Did you clean out?” I told him I did and that I was “like a good scout, always prepared” when it came to bottoming, which made him chuckle. After gloving up his right hand and applying more than ample lube, he instructed me to relax as he took my right leg, put it over his shoulder, teased my hole and then slid his finger inside of me and applied some gentle pressure on my prostate, just holding it for a few minutes.