If I was a virgin at that age, I could completely justify nailing a few hookers to get into the swing of things. You’re probably over-thinking things way too much. You’ve saved a substantial amount of money by not having long relationships over the years, so invest in some hot, sexy hookers. You’ll probably be horrible at first, but keep shelling out the bucks until you’re getting what you want out of it. Maybe after a few sessions get two at once, and have a dirty, awesome sex-fest. Definitely use condoms. Lots of them. After you’re feeling about 10 times cooler than you do right now, get tested for STDs to be safe, and if all clear, go to bars, have a few drinks and start talking to women from your new perspective.
In my single days, if I hit a drought, sometimes I’d have to take home an ugly woman just to get back in the swing of things. Then my sex life would start moving again. Nobody looks forward to doing that, but sometimes it just has to be done. Sounds dirty, and it is.
Go get it!