Hey Anony, this is a really tough situation and I want to, before I answer your question, make one thing really clear - if you are not ready to have sex, don't do it. If he's pressuring you and asking a lot and not listening then you need to leave. That's coercion and manipulation and it's unacceptable behavior.
Now, if he keeps asking and you want to and the only reason you're saying no is because you're worried you'll be bad? Then lets talk about how not to be so nervous! All of this is much easier said than done, so just because it sounds easy doesn't mean it is.
1. Relax. He loves you for you, just being you is going to make it more pleasurable for both of you. Don't try to be a porn star, don't try to do anything extra, just be relaxed and make sure you're comfortable every step of the way.
2. If you're having sex then you need to be comfortable talking about sex. If you're not, then you shouldn't be having sex. So talk to him. Tell him what feels good, ask him to tell you what feels good, and then do those things. Tell him when something doesn't feel good, or feels uncomfortable, ask him to tell you the same so you can stop immediately and try something different.
3. Sex with new people the first time is never perfect, because you don't know what they like, you don't know what makes them feel good or how to bring them to climax. Know that it isn't going to be perfect, but it shouldn't hurt, and it shouldn't make you feel bad. If it does, stop.
4. Don't think about 'entertaining' him, that's porn stuff, think about how to be together, how to make each other feel good and do those things, that's what matters. Especially since it's your first time.
5. Only go as far as you're comfortable. If you read no other point but this, then read this. ONLY GO AS FAR AS YOU ARE COMFORTABLE. If you start to feel like you don't want to do something or you're not sure, say no. If he doesn't listen, leave. You can always say no, you can always revoke consent.
6. If you do want to have vaginal sex, make sure he takes his time to turn you on and finger you. A little bit of blood is normal your first time, some discomfort is normal, but it shouldn't hurt. He needs to take time to make you wet and help you relax. There's a difference between hurt and uncomfortable. If it hurts, tell him to stop. If it's uncomfortable and you don't like it, tell him to stop.
7. Yes, go slow. Each thing one step at a time. Make sure you are constantly checking in with yourself, to ensure you're feeling good and want to continue.
8. Listen to his limits. If he says no or stop or that doesn't feel good, respect that, just as he should respect it for you.
Your first time can be stressful, but that can be negated with plenty of techniques, getting turned on before hand by reading or watching something, talking to each other, asking question, asking if things feel good, telling each other what does feel good, being able to laugh, stopping when needed and respecting boundaries. Just make sure you're ready, and that you're doing it for the right reasons. MAKE SURE HE WEARS A CONDOM. I don't care if it's his first time, too, I don't care if you're on the Pill or something - you should not be having sex without a condom unless you are with a long-term, committed partner and you both know you're both clean.
Most Helpful Opinions
Don't force yourself. If you're not ready, you're not ready.
I think just try to relax and act on your natural desires and try not to be a starfish (a girl who just lies there and shows very little enthusiasm). And definitely try to guide your guide in an extra gentle way and take time with each other so that it won't be a painful experience.
Yes talk to him... if you don't know anything.
Than just follow him on bed.
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Really girls can just lay there for starters. But yeah, tell him it's your first time.
If you aren't comfortable or ready for it dont do it
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