First time, then second, then third...

Heya, get ready for a long read Here goes: somewhat recently this summer, my girlfriend, who I'm in a serious relationship with, and I decided to have sex. So, I went out and bought some condoms and one night in my room, we did a little foreplay, she got in the mood and we were both ready. Both of us were basically stripped down, she told me to grab the condom and put it on, so I did. For her first time, she wanted to do it sitting up, with her kind of straddling me. Now, don't get me wrong, I know the first time is supposed to hurt, and it did. Just barely putting it in hurt her really bad, and we went on for an hour or so, slowly moving deeper, stopping with she told me to, etc. Finally we got it so it didn't hurt near as much and I could get in a little deep and start to thrust kind of fast, but this didn't really give any pleasure for her, but she wanted it to feel good for me. To add, she didn't bleed from what I could tell her first time. We decided to try again for the second time maybe half a week later. This time I was expecting it to feel better for her, and not hurt like hell. But, to my dismay, it seemed like it hurt her almost as much. We still had to do the "go in slowly, stop, take a break, try again" until I could get it in and start to thrust. Again, it felt wonderful for me, but for her, nothing. We then tried again a week later, same thing, it hurt bad for her (this time she said the "high point" of the pain was higher than the first time, she cried this time), and the third and second times, i found patches of blood on the condom and my skin. Still pain for her, and but a tiny bit of pleasure when I started to thrust. The fourth time, we were hoping it wouldn't hurt, but it did, and this time she wanted to stop (which was fine with me.) Is this normal? I've heard of it taking maybe 3 times before it started feeling fine, but it's kind of worrying me. Let me add a few things. One, the condoms have all ended up dry after putting it in, so I'm wondering if the reason it is hurting is because she is not wet enough (to add and I say this without an ego, my penis IS kind of thick...and roughly 7 inches long). I know I turn her on before we go at it, but sometimes when we're trying to get it to work we'll laugh and joke and have fun, so maybe she loses her wetness and kind of gets out of the mood? She had a bad experience with fingering from an old boyfriend so she's kind of shy about that, but recently she has lightened up, so I might try fingering her a little to get her wet in future experiences. She also suggested buying lubricant to help it get in, which is no problem to me. Now, I know your first time having sex, you have to "break" the hymen(sp?), which is supposed to hurt. I thought the first time that I'd broken it, but then the second time when she bled, I thought i'd missed the first time and got it the second time, but she bled the third time too....how can I be sure? Please someone help me out with this, I really want to express my love for her and give her as much pleasure as I can but I'm not gonna be able to with it hurting her every time... and I'm hoping there's nothing wrong with her. Thanks for taking the time to read this big mess and PLEASE HELP!

 

If you want her to get used to it, she has to get over the pain
And yes, I would reccomend lube... or just make sure shes real wet or else it'll hurt. I wouldn't even attempt it if she weren't.

But as far as the pain goes... Fuck her everyday. That's the only way she'll get used to it. You can't wait weeks in between... cause she'll just tighten back up again, and that's of little use to you. And her for that matter. Feel her out first before you try it again. And go really slow, regain her trust a little. It's best to be compassionate with these types of things.

 

I suggest when you first stick it in her, lube her up and go slow, and then perhaps stay there still in her pussy for a little while so her muscles can relax anf get used to you being inside her. Then take it slower than usual and work your way up to a pace shes comfortable with.

Chances are at least 50% of the time shes hurting, shes keeping it a secret, I'm sure she just wants to make you happy. Try keep communication lines open

 

also, a girl isn't going to do what we do, get off and then want to fall asleep. It's not bad policy for a woman to have an orgasm before sex, ya know, give her a minute, but it'll relax her and get all those endorphins flowing to help her relax.

 

Exactly - try giving a nice gentle eat out before sex, it promotes the flowing of juices and lets her relax a bit. Also try spoiling her a bit - a nice massage, telling her how beautiful she is. Also, the position you chose for a first time was kinda hard - when you both know what you are doing it's nice but to begin with? Try letting her be on top, that way she controls how much cock goes in, and can do it at her own pace.

Lube is also a VERY good idea, just make sure it's safe with condoms as I doubt you want to be a father at 17.