teen couple kissing

I’m dating a girl in college who is virgin. She is interested in losing it to me. I wanted ask if you think it would be a good idea to deflower her during an orgasm brought on by oral sex. Would the pleasure mask the pain?  My past lovers liked oral, but I don’t know about virgins.


  • Michael Castleman says:

    It sounds like you’ve discussed this with her. Excellent! Your conversations should help her relax so she can enjoy losing her virginity.

    You provide oral to women. Excellent! Women are much more likely to have orgasms from oral than from intercourse. Women’s orgasm-trigger, the clitoris, sits outside the vagina, a couple inches above it, nestled beneath the top junction of the vaginal lips. Many women love the closeness and special connection of intercourse, but not many come that way. The fact that you provide oral is much more likely to help them have orgasms—and I bet they’ve appreciated you for it. Your new gal should, too.

    About deflowing and pain. Many women experience pain, but many do not. To minimize the likelihood of pain.
    • Talk about if before you do it so you’re both on the same page about what’s going to happen.
    • Make sure you use birth control and a condom if either of you has any concerns about sexual infections.
    • Finger her gently before attempting intercourse. Use a lubricant (saliva, vegetable oil, or a commercial sex lube).
    • Provide her with oral sex to orgasm before attempting intercourse. That way, she’s satisfied. Her vagina should be wet and juicy from coming. And her orgasm should help her relax so she can welcome your penis inside her.
    • When you proceed to intercourse, use the woman-on-top position—you on your back, she kneeling or squatting over your hips. You stay still. Invite her to lower herself onto your erection. That way she controls the speed and depth of insertion, which reduces or eliminates pain. Don’t you move until she’s comfortably seated on your penis.

    I wish you both great sex.

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