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How to make your losing your virginity less painful?

My boyfriend and I have been trying to have sex but have been unsuccessful. At first, he would become flaccid once the condom was on. Once he got used to the condoms, my vaginal muscles were so tight that upon contact of his penis, the pressure made him go flaccid and the whole ordeal was extremely painful for me. I’ve tried using a lot of lube and foreplay but it hasn’t helped so far. I have no idea what we’re doing or how to make it better. I’m trying to relax but it’s hard to not focus on the pain when we’re both inexperienced and I have to guide his penis in the right cavity lol what can I do?
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Most Helpful Guys

  • Likely psychology is playing a much bigger role that you think. You should approach sex together as playful, fun and that foreplay is most important, and stop focusing and/or having this expectation that you both need to have intercourse ultimately. If you both relax, almost find the situation to be comical and really communicate with each other, along the way, and take the attitude that it will happen when it happens, but it’s not the goal for now... then, likely it will slide right in before you know it

  • Just break your hymen if you haven't already. Perform your best downward dog position and have him thrust you. once he's in you can clench your walls around his dick and feel through the pain. When your ready to go after that bit of irritation he'll start massaging your vaginal walls with his shaft. You will appreciate the feeling. Sex will progressively become exciting for you. Enjoy yourself.

Most Helpful Girls

  • Try to "stretch" it with your fingers first during foreplay. I had a similar problem like you and it took me a very long time (and a lot of try and error) until I was able to relax enough to make it possible for the guy to enter me.
    Also do not expect the first time to be exciting. Yes, it will probably hurt even after he's inside. For me it took a few times until I wasn't in pain anymore and could actually enjoy intercourse. But its worth it, especially if you share it with someone you love.

  • Try using your fingers or his first kinda stretch it out with lube

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What Girls & Guys Said

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  • Did he finger you before he tried to penetrate you? Have him use 1 to start and then at least 2.

    Also you can play with yourself on your own time to help relax/stretch you out

    As for him going soft, it's an anxiety thing. Tell him to stop thinking about himself and just think about you. If focuses on himself and his dick, he'll have trouble getting it up. If all he thinks about is you, then his natural human instincts will take over and he'll be rock hard

  • You are on the right path with lube. I would add a vibrator or using your fingers to the mix. Use either of them for awhile to help loosen you up and to help you relax in general. Have him or you rub your clit at the same time and you should relax fairly quickly. Adding in lots of foreplay should help. Once you are wet and lossend up he should be able to slide into you easier. It may still take a couple tries but this should help.

  • First, DO NOT DO THIS WITHOUT A CONDOM.
    Second, see above.
    Third, you may both be putting too much pressure on each other and yourselves. Let it happen more naturally. Start with wandering hands, groping, kissing, fingering/handjob, oral, and then try to move to penetration.

    Do not rush it and do not worry. Lots of NON PETROLEUM based lubricant can help. KY makes an extremely discreet bottle that you can pickup at any grocery, pharmacy, or big box store (Walmart, Target, etc)

  • Perhaps you could use a dildo privately, and it would be less frightening because you would have full control?

  • Get him the blue soldier lol

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