There are a lot of myths around sexual activity, one being that your first time having sex will hurt. Others may include oral stimulation, fingering or handjobs, or anal penetration in their definition. Your definition could also include stimulation or penetration with a sex toy. Regardless of the type of sexual activities you want to try, there are a few general tips or rules you can use to make your first sexual experience more comfortable. Masturbating can help you figure out what feels good during sex, and it can help you feel more familiar with your body. You might find that certain angles or positions are uncomfortable for you while others are pleasurable. You might feel the pressure to give your partner — or yourself — an orgasm. Many people do give and receive orgasms the first time they have sex, but not everyone does. Sex is a skill that you can get better with over time.

2. Don’t fake an orgasm.
ASK BROOK… A GUIDE TO SEXUAL HEALTH & WELLBEING
Having sex for the first time is an important moment for most of us - it can open you up to a whole new world, bring you closer to your partner and give you a deeper understanding of your own body. To make this experience better and pain-free for you and your partner, there are some things you might want to consider. Sure, you might feel certain of it in your head at the moment but discussing it out loud can help process the decision on a deeper level.
1. Communicate what you want.
When you decide to have sex for the first time, you may well be nervous. Good sex is more about feeling comfortable around someone, trusting them and being able to communicate with them than it is about having the perfect technique. Lots of people wish they had waited longer before having penetrative sex for the first time. Some people want to just get it out of the way with anyone and other people want to wait until they meet the right person. You have a choice who you have sex with, so choose the person that is right for you.
At one point or another, I promise you that everyone has felt the way you do—and your feelings are completely normal, valid, and fair. TL;DR: Everyone has pre-sex jitters no matter how much chill they seem to have, and honestly, you should totally embrace the awkwardness. But just so you can make your first time as pleasurable as possible, here are some tips from sex therapist Vanessa Marin and psychotherapist Nicole Tammelleo. Talking about sex with a new partner is a must. And don't worry, you don't have to bring up this convo the moment you match with someone on Tinder, but you should bring it up before you take that trip to pound town, says Engle. Tammelleo says this is especially important the first time you have sex with a new partner.