I can't imagine having sex

Obviously condoms take care of the baby issue and the STDs. Yes not every single STD can be prevented by using a condom, but this is a fact of life and if you're (like anyone else) unwilling to give up on sex because of that, the discussion ends there. If you want to be extra safe, use spermicide on the condom (make sure that if you want to eat her out, you do so beforehand, the taste of pussy after condom/spermicide is not good) and make sure your pubes are at most trimmed. Shaved pubic hair ups the risk that you get infected.

People shit on condoms for being unrealiable, but with proper usage they are as effective as oral BC with normal use. Which means: check them under a light source for damage/holes beforehand, and cast a quick look to see if it's damaged afterwards.

The psychological part cannot be easily solved. It's a long term thing that will only change once you leave your comfort zone. It's hard to convince yourself that you're a sexual being attractive to women when you never allow yourself to experience that. There's a lot between no contact with women and sex, just flirting a little can already change your perspective somewhat. Baby steps.

>>18137742
I don't understand flirting because flirting seems innately creepy to me. I just don't like doing it because I feel it creeps women out. Last thing I want to be is a creep.

>>18137756
Flirting is like talking. It's only creepy if you ignore the signs of your conversational partner. The idea with flirting isn't that you say something openly sexual or provocative right away - yeah sure, you can, but it's a bold move only suited to someone who can shrug off a bolder rejection in turn. Most people do not fall in this category and flirt tentatively. Which means you can abort everything if the other person isn't enthusiastic before saying anything "bad".

Be yourself. Talk to all sexes and all walks of life as you. People will like that, it's rare. Some may even like it enough to want to date you.
You don't need to flirt at all, just don't be a social degenerate that can't pick up on conversational cues. If you don't do something and then do it, it will seem foreign. Weird.
But being yourself is opposite, right? Then just start from there.

>>18137771
I understand what you are saying but I have like no idea who I am. I feel like I have just been acting my whole life. When people say "just be yourself" I can't even figure it out.

I gotta find more places to meet women my age. Where do women in late 20s even go? Single women in their late 20s are super rare.

>>18137803
If you don't know who you are then work on that first and foremost. If you immediately jump to trying to please the opposite sex you'll do just as you have so far in your life: put on an act. Go out in public, do things with people, have social interaction and figure out how each situation effects you. Trust me, if you try to date now and it winds up a disaster your mental stability will be all but nil.