Hi,

A few days ago I (kinda, almost) had sex for the first time. Me and the girl I was with both got naked and it seemed like I had trouble getting a hard enough erection for the penis to insert into the vagina.

To be more specific, since it was my first time, I had trouble finding the precise spot of her vagina where I’m supposed to insert my penis, and since I didn’t want to admit this is my first time I asked her to insert it (I’m quite old for someone who just had his first sexual experience). My penis got kinda hard, but not rock hard, and she said it wasn’t hard enough for her to put it in.

We kept trying to stimulate me in hope that I get harder and it kept not happening, always reaching this “kinda hard” state but not above it.

There was also a time where I finally got it “rock hard”, she managed to put it in, we did it for like a minute maybe, I didn’t feel much because of the condom I was using so I suggested to switch positions, pulled it out and saw it wasn’t “rock hard” anymore, and so we couldn’t insert it again. We stopped because it got late and she had to go, hopefully we’ll try again next week.

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My questions are the following:

1. Do you have to be “rock hard” to have vaginal sex? When I masturbate I don’t think I get that hard most of the time (unless I’m really turned on) and I manage to come every time.
2. Is there a guide (with pictures or video) that shows what’s the right way to insert your penis into the vagina? I always hoped it would be trivial but I’m not sure if it is to me.
3. Not really related but still – I tried masturbating with a condom (EDIT: a different and thinner one than I used for sex) on and noticed that when I came, the sperm reached all the way back, almost to the base of the penis. Is that normal? I thought it’s supposed to stay in the front.
4. If you have any other suggestion you could give me I’ll be happy to hear. My first experience wasn’t really fun for me and I’m hoping for the 2nd one to be better for both me and my partner.

4 comments
  1. You are loose and/or using the wrong sized condom. There has to be absolutely zero air in there.

    If the condom is the correct size then it’s “hugging” the erect penis, almost like a tight glove (which it is, basically) or a second skin.

    You need to find out ways to get your penis to stay hard for long. Maybe try some cardio or kegel exercises?

    >Is there a guide (with pictures or video) that shows what’s the right way to insert your penis into the vagina? I always hoped it would be trivial but I’m not sure if it is to me.

    It’s perfectly fine to ask her to guide it in there the first few times. Then after you’ve gotten used to it, you can do it for yourself. Else, just lie down and ask her to “sit on it”. Oh, and make sure to use adequate lube!

  2. 1. No. It helps, but you don’t have to be. Maybe she is too tight?
    2. You can help “navigate” with hand – insert finger and the you at least know where to go.
    3. When pulling condom, you should hold tip of condom, to create place for cum to go there. Also check size, there shouldn’t be way for cum to go around.
    4. Explore 🙂

  3. I think that maybe you would have a better next experience if you just tell her that you don’t have a lot of experience. She can show you stuff and the expectations wont be on your shoulders rather You will get a chance to relax and enjoy everything

    For the 2 point you can look up female anatomy or maybe going down on her would help you get a look at everything and touch her bits before you have to do it without seeing everything (Its also another thing that can make your experience more fun and pleasurable)

  4. Seems to be that there could be some anxiety on your end based on the self judgment that you are older and should know. That is not necessarily a good way to enjoy intimacy if you aren’t willing to be open to communicating.

    Having said that. If you masturbate watching porn, then you’ve seen there are 2 openings the vagina and the anus. If you are stimulating her, the orifice is below her clitoris and between the labia.

    There is no rule that you have to be completely hard to insert the penis, but it varies on the size, if you were blessed with a big one it might be okay, if you are wearing a condom it is better if you are hard not to avoid air bubbles to be formed. If you have difficulty staying hard, ever heard of a cock ring? If you don’t have one, buy one and thank me later.

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