When are you originally suppose to orgasm during sex?

When it comes to sex, I have never orgasmed. The only way I can orgasm is whenever I watch videos.
I won't go into detail over that, and it doesn't involve toys. Well, I have had this friend with benefits.
Whenever we have sex, I never orgasm. He's a bit rough when it comes to sex where I'll hurt.
He'll obviously know because I will tell him that I am sore, and that I need a break.
Last night we had sex, and I tapped out within 10 minutes because he will go so fast. To the point,
I will dry up and we never roleplay during sex. I have never given a blowjob before due to my childhood past. As a kid, my step brother tried to do sexual acts with my sister and I. I was traumatized as a girl.
I grew up, and my family knows about it. I don't see my step brother anymore, and I feel awful not going down on my friend. He doesn't know anything about my past and my step brother. I've gave him a hand job. I'm also nervous about messing up. It's just never the right moment for me. My friend with benefits and I have been messing with each other for 3 years... which is crazy! We can't cuddle as long because he will make the move so fast by trying to finger me, and I just am never ready. I mentally prepare myself. I am comfortable in my body and myself when we are naked. Everything just happens so fast. We don't kiss. Just cuddle for like 10 seconds..

He'd ask me if I have finished. I'd lie and just say Yes. He would say something like..
"Oh.. I couldn't tell.." It's kind of cringy to me.
I don't know if it's because he is so rough. Don't get me wrong, I do like it. It's to the point that I am falling over, needing a drink of water, etc. He'll try and catch me from falling if we switch positions. Yeaaaaah.

My friend IS respectful towards me. We are close, but we aren't really close to our sexual thoughts.

My main question. How do you know if you're going to orgasm? Maybe I'm not with the right person..
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Most Helpful Guys

  • Fewer than 25% of women reach orgasm from intercourse alone. My SO doesn't either. Here are some strategies you can ask from a sympathetic lover. I use these at home.
    1. Have him either bring you to the brink of orgasm or into it with oral. If he's not good at it, send him this link so he can learn.
    www.slideshare.net/aee_fx/she-comes-first-15567847
    2. The Cowgirl position allows deep penetration and strong contact of your entire "vulva". No need to bounce. Just thrust and hula. It also allows easu access to your clitoris by you or him, to "supercharge" intercourse. My SO HAS cum this way.
    *This does not address whether he is the right guy for you but if you can work through this, you will know better.

  • You're not with the right person.
    You have communication issues; that's part of it. He's too rough and you don't tell him to stop. How could you possibly tell him what you do like and what to keep doing? You need to. Guys seldom know what to do on their own.
    Do you orgasm on your own or not? You were unclear in your first two sentences. If you haven't on your own, I'd suggest you start there. Figure out what you do like and what works. From there, you can better instruct another how to make it happen.

Most Helpful Girl

  • I think as you said you aren’t with the right person... not everyone is compatible when it comes to sex, everyone likes different things. Also it seems like he doesn’t give you much foreplay and if it hurts makes it hard for you to actually enjoy which would be why you aren’t able to orgasm. I’m surprised that you continue to have sex with him for three years without having an orgasm, do you think maybe you continue to because you want to feel close to someone rather then it actually being about the sex.

    • He's been a really good friend. Somebody I can look at in the eyes, knowing that we had sex multiple times. Nothing is awkward between us. The reason I continued to have sex with him was because I felt comfortable with him the most. Just sexual actions (blowjobs), I am not comfortable doing with him. It feels good to have him close, but sometimes we don't talk to each other for weeks. We both have busy lives.. I've known him since sophomore year of high school, and he's 22. While I am 21.

    • Some of his actions, I do question.. I know he's not serious for a relationship. Neither am I. He gets very protective if a guy is coming at me wrong, but I think that's normal. I'm assuming from himself.

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What Girls & Guys Said

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  • "Not with the right person" is not the answer remotely in my consideratio. You don't ask for what has worked for you alone, and then when it hasn't worked you tell him it's fine anyway. You're probably not getting any build up or help, and without any direction, he's just coming through to get himself off. It's kinda hard to orgasm when you aren't even getting wet enough for it to not hurt, let alone be pleasurable.

  • What the other guy said
    And I'll add that it seems you need love to open up sexually rn, not hook ups

  • AFTER her.

  • It doesn't sound that he all that respectful of your needs. If you are going to orgasm, you will know it. The involuntary muscular contractions every 0.80 seconds are kind of a giveaway that it's happening.

  • You are afraid and he doesn't understand. Try riding him so you control the tempo and he's free to use his hands elsewhere to stimulate you. It sounds like you get fearful when he takes the lead. With you in control the fear will go away.

  • Sounds like you need a different person who understands your vibe. Different angles and nuances

    I had one ex girlfriend that I only made orgasm once in 9 months. She took a very long time

  • You need a good guy who doesn't rush and will take his time and go slow with you

  • Sounds like he sucks at sex.. either tell him what you want differently or find someone else

  • When you're partner is also about to do it