[newhere808]

Forgive me for sounding crude, and anyone with great knowledge please correct me, but I do believe it is impossible to penetrate a woman completely for the first time without breaking her hymen. My first girlfriend was heavy into martial arts, so hers was already broken (her story anyway) but I do believe that's the way of it.

Your right to build up to it though, there is nothing worse than placing a feeling of urgency behind it. She may have to get to the point where she is willing to take the pain with the pleasure. Having only been with two women in my life i'm no expert, but my first girlfriend did complain about my size, and she was more comfortable "spooning", or "cowgirl", so that may help.

Best of luck.

[Na-Na]

Forgive me for sounding crude, and anyone with great knowledge please correct me, but I do believe it is impossible to penetrate a woman completely for the first time without breaking her hymen.

Actually not true. It can stretch, or, if it's a partial hymen, be pushed to the side. There is the possibility that you could keep your hymen in tact through more than one session. And it is very possible to break it outside of sex. Sports, horseback riding, dance, gymnastics, being active; all of those are likely to break a hymen. The actual breaking of the hymen only hurts for a few moments. A lot of girls break theirs and never feel it.

And when the others advised lube, they weren't suggesting she wasn't getting wet enough. When size is an issue, lube makes penetration easier for both parties. It will make the experience slightly less painful, and will reduce the possibility of her tearing. Make sure to using it on the outside, too, and putting a little on your shaft probably wouldn't hurt matters any.

Personally, I would advise completely stopping for a few moments after penetration. If she's up for it, have her do the initial movement. My SO is large enough (and we're infrequently enough) that it hurts. Letting me control the pace until I've accommodated him makes it hurt less.

[newhere808]

Actually not true. It can stretch, or, if it's a partial hymen, be pushed to the side. There is the possibility that you could keep your hymen in tact through more than one session. And it is very possible to break it outside of sex. Sports, horseback riding, dance, gymnastics, being active; all of those are likely to break a hymen. The actual breaking of the hymen only hurts for a few moments. A lot of girls break theirs and never feel it.

Ahh, thank you for the clarification.

[hchinaski]

thanks for all the feedback. my relationship is at the 2.5 month mark, and we still have not achieved penetration. i am trying to be patient, but i getting mildly discouraged. we are becoming more intimate and comfortable, so we are kinding of branching out with foreplay and incorporating things that are new experiences to her. we see each other about twice a week, and we generally "make out" for several hours each time during which, we try penetration a few times. i have waited until she is dripping wet, and have been letting her guide me in with her hand, but the opening is so small, even she has great difficulty guiding me to the correct spot. when i am at the right place i try thrusting slowly, but there is absolutely no give. it is like hitting a wall. when i start to push, she grimaces, so i pull out. i ask her if shes ok and she says "it didnt feel right". even when i use my finger, it is a very tight fit with little clearance below her pubic bone. i have never had sex with a virgin before, so i have no context, but it doesnt seem as though her hymen is very elastic. i am trying to be sensitive, maybe too sensitive, i dont know. but it doesnt seem like i can break the skin around the opening no matter what. i am not going to press the issue, i am going to wait for her. she has scheduled her first ever gynacological exam this month, so she is really just beginning to integrate her sexaulity into her life. but i really want to have sex, and when we engage in 3-4 hours of foreplay, it becomes tough to not be able to do what seems very natural. if anyone can speak to the physical issues mentioned, especially any ideas on why it is so difficult to get to the right spot and why there seems to be no give or elasticity to the hymen, if this is normal and i just need to push harder, anything. i will respect her physical timetable and give her whatever she needs, but i want to have a fulfilling sex life.

[kira]

Odds are low you are going to have sex without breaking the hymen. That's kind of suppose to break. It's probably quite rare for it to not break with sex and probably bordering on impossible for it to not break if you are larger than average or after multiple times of sex. It's going to happen so trying not to isn't going to help. Trying to avoid too much pain is good though. The more aroused she gets the more it helps not only for lubrication. Part of arousal and sex is that the brain starts to interpret some pain as pleasure instead. It happens to different degrees in different people but the more aroused someone is the less it will hurt. That doesn't just mean getting things wet though. From experience I can say pain down there will cause things to get wet and hours of stimulation will cause things to get wet. It doesn't mean mentally a woman is very aroused or that much is physically happening in the brain. Eventually if she gets aroused enough she should want things as much if not more than you do and probably end up breaking the hymen herself by moving against you. It's kind of impossible to stop that motion if you are aroused enough. Figuring out what to do to get someone that aroused really just requires experimentation. Especially when they don't know what feels good.

[newhere808]

Perhaps having her try penetrating herself with a smaller dildo or something to at least feel full penetration from something other than her finger? It may come down to it that if she wan'ts to accomodate you she will have to deal with a bit of pain for a bit until she get's used to it, unless there is some medical explanation. Not to sound insensitive, and I applaud you for your patience, but it certainly wouldn't be the first time that i've heard of pain during "deflowering".