JeffThom

@JeffThom - With other things in life, do you jump into the deep end right away, or do you tend to take small steps?  I tend to be risk adverse.
When I decided to act on my attraction to men (at age 44), I started with an erotic massage as it felt that it would not be a big risk.  Back then advertisements on the massage sites were less restricted, and the guy I hired listed his services as 45 minutes of massage followed by 15 minutes of oral play.  I decided that was enough to dip my toe in the water.  For me, just having another naked man in the room who was touching me was wonderful.  And the oral play made it even better.
After that massage I was comfortable taking the next steps.

My first time with a man was with an escort. Similar story, kept my attraction to men hidden. That first experience was a life changer. Before I even knew about Rentmen, I found www.canadianmale.com. I was heading to Toronto for work and contacted an escort for a meeting. It was super easy and when I met him, I told him that it was my first time. He was super sweet, understanding, and made it a great experience. Happy to discuss more via PM. 

Bluefin, great point also.
Communication is the KEY.  When booking appt (phone text or email) be up front if this is ok and if an extra charge for it.
That way everyone is on the same page

Don’t be afraid to tell them your situation and what you’re looking for. The more he knows the better he’ll be able to make the experience a positive one for you. Look for phrases like “boyfriend experience” great with first timers” etc. In the ads. Good luck!

Sounds like you are looking for an escort and not a masseur. Skip the massage unless you want a bit of that as foreplay. Rentmen is the website with the most comprehensive list of escorts. There is a “position” menu where you can select that you want a “top” and it should narrow the field down to escorts that are into that.  Search this site for experience once you have a list. I usually recommend meeting in a public place (Starbucks etc) if it is the first time so you can get a feel for the guy before you spend time behind closed doors. Take it slow - find the right guy and then make sure you are prepared. Know your limits. Be safe out there young man! 🤓