I consider myself to be 90 per cent straight. As far as the other 10 per cent goes, I given hand jobs to men occasionally. Sometimes they return the favour, but I'm fine if they don't because I enjoy giving hand jobs. I may give a blow job one day, If the guy wore a condom (peferebly flavoured). However I would really like to be on the receiving end of anal sex. I feel sure I would enjoy the experience. It would be great to see what an anal orgasm feels like. However I have anxieties about trying it though. I know you need to be toatally relaxed when it happens to get the best from it. I am a middle aged married man, my wife doesn't know about this and never will. There is a gay sauna in my town, which I have visited twice. On both times, I just gave hand jobs, when I really wanted a cock in my ass. My anxiety, is the risk of STI's particulaly HIV because recepive anal is one of the easiest ways to get infected. Without knowing for sure, there is only condoms to rely on, there's always a small chance of one breaking. I anally masturbate with sex toys and other objects, it's just not the same. Maybe I should just leave it as a fantasy. What do you think I should do?
You've been to a gay sauna where you enjoyed a few cocks. Attached to those cocks are potential owners who are clean that would be more than happy to form a friendship. A FWB type friendship. Such an arrangement could promote learning that your new found friend has been tested clean and can eventually lead to fulfilling your desire. Give it a try. A wife wouldn't be suspicious of a couple of guys enjoying time together over a couple of beers. Who knows where that may lead.
Find a doctor, clinic nearby or online that will prescribe PrEP for you to take before receptive anal sex, which is about 99% effective at preventing HIV if taken properly. There have only been a few handfuls of people taking it properly who caught a rare HIV strain resistant to it. Out of millions of users worldwide having many millions more sexual encounters. Truvada is an inexpensive generic. You will be required to get STI tested every 3 months. Also ask for DoxyPEP, which you take afterwards to prevent chlamydia, gonorhea, and syphilis.
There are only a few reasons comdoms break. Check the date on the package, go slow, use plenty of lube and start stretching with dildos. If you can avoid small tears in the rectal tissue by perparing youself before penetration you should not have any issues. If you are still super concerned have the guy pull out before he cums.
Start with HJ with someone you are comfortable being with. Eventually give a BJ. Swallow next. If you feel it, anal is next. If not...you already have two fun things to do!