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I'm a sexual health counselor, and I've actually answered this kind of question before here[1] . But here's the copy-paste.
Never stick anything in the butt you can't pull out easily. If something ends up stuck in the butt, don't try to get it out - you'll only push it in deeper. Prepare for a really weird poop.
Not saying yes means no. Make sure you have consent. No maybe.
Wash your goddamned sex toys. And consider using condoms on them. They'll last longer, and be more hygienic. But wash your goddamned sex toys.
If you think you need to use lube, use lube. Try to use a water-based lube. Never use an oil based lube. Never use a silicone lube on a sex toy.
If they say you don't need a condom for any reason, then you need a condom.
Learn how to use sex toys. Trust me.
There is no shortcut to finding your perfect sexual partner. You need to experiment to find out.
Don't try to inflate her vagina like a balloon by blowing into it.
Don't smack the balls unless you have consent.
A vibrator isn't a dick replacement. Don't be intimidated if her dildo is larger than you.
Each person has a different thing that turns them on. Never assume your current partner will be turned on by what worked on the last person.
Get tested. If you haven't been tested before, do it right now. Then get a subsequent test every six months - and don't assume you don't need protection just because both your and your partner's tests come up clean. Some STIs take a long time after transmission to register in tests.
The G Spot is real.
The best sex toys are either high-grade silicone, glass, or surgical steel. The latter two are also great for temperature play. Any of these three can be washed in the dishwasher.
NEVER FUCKING DOUBLE WRAP. You might as well not use a rubber - the friction will cause holes in both.
If you're girthy, don't just shove it in. For the love of fucking god, don't just shove it in.
If you haven't fucked before, your dick is probably going to be limp as a noodle due to stress. Shit happens. Get on your knees, and express yourself with oral. It'll win you big points, and probably a second chance.
Don't shit yourself. Unless that's what your partner is into.
Don't assume your partner is going to have the same kinks five years from now. People's tastes change.
If you're a sexy vanilla, don't be ashamed of it. Most people are, and you're potentially comparable with the majority of the people on this planet.
Men - there is an orgasm button in your butt which will give you an orgasm like you have never ever experienced in your life. You can hit it yourself, but it's easier with a partner. Good luck.
The nipple is amazing - but there's a whole tit you're not paying attention to.
If the sex act has a weird name, ask what's involved before you give consent.
Female condoms (receptive partner condoms) have improved significantly over the years. They're a lot more comfortable, they cost less, and they give you a lot of control.
As romantic as it sounds, never sleep inside you partner/have your partner sleep inside you, if you're using a condom. Between shifting and shrinking, all that semen will have a nice easy opportunity to work it's way up the sides of the rubber.
If you are sharing cocks or toys with someone, use condoms, and change them every time they're used on a new hole (anyone's hole).
Don't use flavoured condoms for penetrative sex. They're better than nothing in a pinch, but you're pretty much asking for a yeast infection.
Lastly - don't give a fuck what anyone says. If it's consensual, safe, and private, then the whole world can fuck off, except for the two of you. Do whatever feels good.

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