I was about that age when I first had sex, too. 20 is definitely old enough, hormones are high and it's an experience you won't forget.
Q1: Topping/Bottoming - All this should ideally be decided ahead of time with communication. It can be fun and flirty and not clinical. But male/male sex goes better when everyone's prepared. If you are truly brand new to everything and this is not just a one-off hookup, I would take it slow and not expect full sexual intercourse on the first meet-up. If he is as inexperienced as you, it should be slow and sweet. Do some good personal hygiene and clean up your place, get together, put on some tv or music you both like and snuggle up together. Just enjoy each other's company and bodies. Get some clothes off eventually, feel your dicks, then feel each other's. Talk as you're doing things. Tell him what you want to do and ask him what he wants to do. If you feel comfortable, you could try trading blowjobs. Don't be intimidated by the pros on film. They're literally pros. Just put your mouth near it, kiss it, lick it. He'll think whatever you're doing is incredibly hot. And you'll probably think the same when he's on yours. Ask him how he likes it best, tell him how you like it. Try to do things you would want done to yours. Don't try to put the whole damn thing in your mouth and gag on it right away lol, and don't force yours in him either unless he's ready. And do watch the teeth. Almost no one likes teeth. It should feel very soft and wet, ideally. Maybe with a little suction.
Q2: Expectations - Whether you are topping or bottoming, if he is more experienced than you, he should lead. Tell him you want to fuck him, but it's new to you and ask him to show you how he likes to get fucked. It probably is easier to have gay sex the first time as a top, since all you have to do is stay hard (easy at 20), not come instantly (difficult at 20), and not tear his hole up (easy if you're gentle). The hole is a muscle and it's pretty tough and can take a lot (see the internet), but it is very sensitive and it's easy for it to feel painful if it's not relaxed and well lubricated. If you are bottoming for him, I would not let his dick be the first thing that ever goes in your ass. Ideally, you should buy a small dildo (about 1-inch diameter) or a small butt plug (1.5-inch diameter at the max), or a set of anal dilators (that go up in size from very small to the size of a dick). You also have your fingers. Again, use lube. Since it's just you and your fingers and you don't have to worry about condoms, using vaseline or coconut oil here is a good start . Just grease your fingers and play around with your freshly showered clean hole. Insert one finger gently and try to find your prostate a few inches in. Try a couple fingers if you like it. About 3 fingers at once is about the girth of the average penis, which can give you some confidence that you'll be ready when you're with him. If you are going to fuck him, you should also start out with fingers. Either let him finger himself or you get him ready (lubricated, relaxed, horny and loosened up) with your own fingers. Also make sure your nails are trimmed short and smooth before doing this. And let him then guide himself onto your dick the first time. The other expectation: What does it feel like? Anal sex DOES hurt, don't let the women's magazines or dudes on the internet tell you otherwise. But "hurt" is an interesting word. A lot of times we like things that cause discomfort, like the gym or playfighting with friends. But there's a point at which "hurt" is not fun. Sex is the same way. It will feel strange and uncomfortable and may sting quite a bit for about the first minute, especially your first time. Your hole muscle will probably spasm trying to close up with a sensation it's not used to. After a first slow and somewhat painful minute, it should relax and it should stop hurting and it should feel amazing. If it doesn't you may want to stop and try another sex activity. Then go home and play with your dildo some more for practice. If you're good after he gets it in, this is where it really gets fun. It's a very vulnerable experience, letting someone else be in charge of your body in this way. But it's really hot, too.
Q3: What do I wish I'd known? Cheap water-based lube is trash. Good water-based lube requires mixing up and that's complicated. Just buy some good silicone lube at a sex shop or online. If you have sex without condoms, oil-based lube is absolutely the best. Always have lube on hand. Vaseline, coconut oil, etc. will work in a pinch (without condoms). Do not try to use stuff like hair conditioner as lube. Can sting and doesn't really work right. Cleaning out for bottoming is a skill that takes time to learn. Please do NOT follow that awful cartoon they keep posting on Reddit that tells people to sh*t in their showers. The shower plumbing is not made for that. There is no bathroom on earth that doesn't have a toilet 3 feet from a shower. The water can be put in in the shower and put out in the toilet. Much cleaner. There's a pretty good write-up on Fort Troff (
How To Douche Before Anal Sex, Fisting Or Just Everyday Ass Play - TOY). I would add that you can do multiple 5-7 second rinses (water goes in for that number of seconds) in short succession (maybe like 5 of them, just in and out) and that works for a quick play session. If you do 20-25 second rinses (about 10-20 minutes getting the water out for reach one), at least 3 times, maybe even 5 times, you can basically be a cumdump for hours. Another trick is that after you think you're clean, play with a toy for a few minutes as this can sometimes get any extra water out ahead of time. Then do another quick rinse or two if needed after that. Even so, lay a towel down on the bed or couch when you're fucking just in case. Sometimes there's a tiny bit of mess, even when you clean extremely well. Just have a towel available to clean up and don't worry about it. As long as you/him has made a good effort to clean otherwise, you can probably keep going. Towels can be washed and you both can take a shower after. Also, cleaning is something to practice ahead of time and not be trying to figure out right before he gets over or after he's at your place. Your anatomy will be different and respond differently to cleaning out than other people, so you have to practice alone and figure it out for yourself. Also, once you're out there hooking up with guys, please don't be one of those bottoms that makes a date with people and then tries to make them wait 2-4 hours while you figure out how to get clean. Get clean first then find a friend to play with. Also, even if you are naturally dominate and prefer topping overall, I think it's good to bottom a couple times so you know what that side of the experience is like for the other person. Condoms/safe sex: I think we have a really puritanical culture that has exaggerated a lot of the dangers of bare sex. However, there are lots of options for people to choose from now. Prep and Doxy Pep are available free online now in a lot of places. Condom sex is fine, however, it is a rougher experience for the bottom because it's rubber and not skin on skin contact. If you and your partner are both extremely sexually inexperienced, you're not going to give each other anything going without, as long as you're monogamous. But do make sure to clean up and visit the restroom after fucking a guy, as general bacteria can cause irritation if you don't use condoms (never had the problem but it can happen). Anyways, I hope it goes well for you. Don't stress about it too much and try to enjoy these new experiences, this new person you like that likes you, and have fun.
