A
female
age
30-35,
anonymous
writes:A guy that I've known since elementary school (we've long since graduated high school)and I started talking again and came to realize we both live in the same neighborhood. So long story short, we've gone out for quite a few months and we'll be having sex for the first time soon. I'm a virgin. He's not. He is also rather "big" I guess is the best way to put it. 8.5" to be precise. We will be using protection and I have masturbated a few times but never really stuck my fingers in myself and I have used tampons before even if about only the size of 1 1/2 of my fingers...any suggestions or advice? Also would taking painkillers ahead of time ease the pain?
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reader, anonymous, writes (7 April 2013): This is verified as being by the original poster of the questionThank you for the advice so far! I was curious about the painkillers because I hadn't seen it mentioned in any other threads on here so far and wanted an answer as to why. I am 100% sure that I want to do it and yes, he has been tested. We WILL be using protection, however I won't be using birth control since my doctor highly suggested not to due to a medical condition.
A
female
reader, chigirl  +, writes (7 April 2013):
 @IamHereToHelpYou, pain killers do not interfere with birth control pills. Antibiotics can interfere with birth control pills (make them less effective), but not pain killers.
I also recommend birth control pills, as long as you've been tested for STD's. Has he been tested? He should get tested, even if he's always used a condom before. If you go ahead with the two positions I mentioned you could pass STD's to one another, even if there's no penetration. So it is necessary to always get tested when you have a new sex partner.
I also recommend you use both condoms and go on birth control pills. At least for the first few times until you get the hang of things. If he's big, and your tight, then the condom might rip. It's happened to me before. If there's too much friction on the condom it can rip.
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A
female
reader, chigirl +, writes (7 April 2013):
Oh yeah, and buy a bottle of lubricant. In case you can't get wet enough by yourself. Not all women have enough natural lubricant, which will mean you need to add some store bought. That said, with the right touch I think you will be wet enough.
One of my exes was wide. He wasn't long, but he was wide! And the first time we had sex (I wasn't a virgin) it hurt so much we had to stop. The second time I gritted my teeth and just took the pain (I was young and stupid and didn't know you could buy lubricant..). I couldn't even WALK afterwards, it hurt so much. But then we went to see a nurse, and she told us to buy lubricant. We tried it, and suddenly sex was a lot easer. I also found that I couldn't have him enter me in any other position than in missionary.
Then again, my ex didn't have the skills in bed to make me extremely wet. Or, maybe I just wasn't attracted to him enough. Anyway: buy lubricant! And not the one with any "stingy" effect or "menthol" or anything extra, because they can sting and be painful... Just buy the normal no fancy, ordinary kind. Make sure it's one who can be used with condoms if you're using condoms.
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A
female
reader, chigirl +, writes (7 April 2013):
Don't take pain killes. Take some afterwards if you feel unwell, but I don't see the point in taking them in advance. You might not need them. However I have a friend who got belly aches after having had sex for the first time, and that is a normal reaction (however it's also normal to not feel any discomforts at all).
What I suggest is that instead of focusing on penetration you fool around instead. Naked, in bed. Rub up against each other, make each other feel good. Maybe he can try lightly pressing up against you, but don't go for full penetration right away. Sex is so much more than intercourse. Try to please each other in other ways first, and get comfortable about being naked together. Touch each other, learn what you like and dislike, what turns you on and what doesn't.
You'll be ready for sex when you're dripping, soaking wet down there. And then it probably wont hurt at all. It can feel a bit weird, but should also feel pleasurable. If you're ready for it. If it is painful you should stop.
I also suggest, if you're of age, to have a glass of wine together to ease the nerves. Makes you relax. Not so much that you are drunk, but enough to take the edge off. Just enjoy each other. Please each other in all the amazing ways possible before penetration.
A personal favourite of mine, that I think you should try, is this: Lay next to each other and face each other. He should have his arms around you, and you have one arm around him (the other close to your chest as it would be uncomfortable to have him lean on it). Place his penis between your legs and lay there and kiss each other, while you gently rub up against each other. It is very stimulating for your clitoris and for him as well. In addition it is a sure way to make you all lubed up.
Or another favourite of mine: he lays on top, and with one leg between your legs (meaning you also have one leg in between his legs. Place his penis up against your belly, or in between your legs (dependent on his size and curve, place it where it is most comfortable). Kiss and cuddle in this position, and just feel each others bodies pressed up against each other. Both these positions are capable of so much pleasure he can reach orgasm without penetrating you. It is also very pleasurable for you.
Try it. Only try to have him penetrate you if you're so excited and yearning for it that you can't wait any longer and are soaked between your legs. Your vagina prepares for intercourse this way, and will "open up" and be big enough for him to enter without pain.
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reader, anonymous, writes (7 April 2013): No OP, don't take pain killers that's the worst idea I've ever heard of in my life.
OP pain in your vagina is to tell you something is wrong or something is being damaged, you don't take pain killers to mask that or you won't get the signal that he's actually causing permanent damage that can ruin your sex life for good.
OP pain is important when it comes to being with a larger man, it's the best way of gauging how fast, how deep and what angles he should go.
OP a certain amount of pain is normal but upping your pain tolerance using pain killers is only going to mean you tolerate pain that is damage that your body actually can't tolerate and you may wake up the next day with a heavily damaged vagina needing medical treatment.
Before you think anything OP, experiment on yourself a bit. One finger to two and so. See what you can handle when really turned on.
On the day he has to give you plenty of foreplay, you have to be as aroused and lubricated as possible and he has to be gentle. OP be prepared for it not even get to intercourse. I've been with women their first time and it took a few sex sessions for me to be even able to get it it because my fingers alone caused pain.
OP this is most likely not going to be a Top Gun moment with Take my breath away playing in the background, it's going to be awkward, fumbling and may be too painful to continue with that session, but that's normal. Patience is a virtue when it comes to big penises OP.
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A
female
reader, anonymous, writes (7 April 2013): Hi Hun,Just make sure you use protection if you do have sex but don't be pressurised into having sex if you aren't totally 100% sure.I didn't bleed on my first time and I've never bled during or after sex, I do hear some girls bleed due to the hymen breaking but I'd take a tampon with you just incase you do. If it is painful, make sure he stops and you can always finish off in other ways.Maybe foreplay would help first before going straight into sex and take some lube to ensure there is no friction pain.Maybe even invest in sex toys beforehand to get used to the feeling of a penis inside you and explore your own body to get to know what you like.I hope this helps . And good luck and have fun ;-D
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