Thanks!

(she is ridiculously hot though)

Also, if I do take her up on her offer, and we start hanging out more, how do I talk to her brother about it, without making him want to hit me?

PS. Thinking about this doesn’t make me an asshat of a friend and a pervert right?

A: You are definitely not a pervert because you are attracted to your friend’s sister. Most boys your age are attracted to one or some of the girls in their lives, and this is completely normal.

First of all, just because your friend’s sister asked you to “hang out”, it does not necessarily mean that things need to get physical between you two. You might want to talk to her to see exactly what she wants (dating, relationship, something physical, etc) before you decide to do anything.

Secondly, 3 or 4 years can be a pretty big difference, especially next year when you turn 18, when there could be legal concerns depending on how her parents feel about your relationship. We have read that in your state, the legal age of consent is currently 14 with parental consent and 16 without it. We are not lawyers, however, and these laws do change. Things could turn out ok, however. It depends a lot on both you and this girl, how mature you both are, and how both of your families feel about things.

You mentioned that you are afraid of your friend, this girl’s brother. You may want to try talking to him about how you feel and about what his sister has said, and see how he reacts to that. From there, you can gauge whether or not it is worth pursuing things with the sister.

A: Difficulty achieving penetration is not unusual when you’re trying sex for the first time. It is possible that your vagina is too tight for him to get inside, but that’s not very likely. It’s far more likely that the two of you just haven’t yet found a position that works for you. Other possibilities are that you have an intact hymen that is getting in the way, or that his penis isn’t getting hard enough to penetrate you.

Have you tried exploring your vagina yourself? The better that you understand your own body, the better that you can guide your boyfriend. The first thing to do would be to penetrate yourself with your fingers and get an understanding of your vagina’s position and angle. Pick a time when you’re comfortable and relaxed, and have some lube handy. We recommend using a water-based lube. Then when you and your boyfriend are ready to try having sex again, use your hands to guide his penis into the right spot and angle.

As for being too small: if you can fit two fingers into your vagina, you are not too small. If two fingers won’t fit, start with one. As you get used to the feeling, you’ll likely be able to work your way up. Your vagina is a muscle, and a strong one. If it’s clamped down tightly it can be very difficult to penetrate, but as you increase your awareness of it you can learn to let that muscle relax.

Also, you mention that your boyfriend had a hard time having an orgasm. Does he get erect and stay erect? Penetration is hard to achieve when the penis is not fully erect. If that’s the case, feel free to write us again and we can give some suggestions for maintaining an erection. As you gain confidence with your experiences you can try things such as masturbating him to orgasm, or doing oral sex.

Finally, if when you explore your vagina you find a flap of skin that’s partially or completely obstructing the entrance, that’s your hymen. Women’s hymens are all different, with some being very thin or barely there at all and a few being thick and nearly covering the vagina. If you do find your hymen intact and in the way, then it is going to have to tear before you can have sex. Hymens sometimes hurt a little when they tear, but sometimes not. Probably the easiest way to tear your hymen would be to use your own fingers. Put one or two fingers into your vagina and gradually increase pressure on the hymen until it gives way.

Lastly, if none of this works for you we suggest you see a gynecologist. They will be able to diagnose any problems and suggest a treatment.

A: First times can be a lot of pressure and stress. For most men having one orgasm by masturbation or oral sex allows them to keep a second erection for a longer period of time. Most men need 10-15 minutes before getting a second erection. Remember, if you do cum once and would like to get another erection there are many activities you can do for and with your partner while you’re waiting to get hard – like oral sex for them or other stimulation.

We recommend that if you know you’re going to have sex in the evening, plan to have an orgasm in the afternoon. That way you’ll be less sensitive for your sexual date and you won’t have to depend on oral sex before intercourse. It will take some of the pressure off.

Question 1. I hear that when a girl has sex for the first time that it hurts for her. My questions is, is there any way to make our first time less painful for her?

Question 2. Another rumor I hear is that when a guy has sex for the first time he comes very quickly usually resulting in the woman not being satisfied. What would you recommend for me to last longer my first time and to last longer over all?

Question 3. This is my last question and it’s more of an overall question. What are some tips you have for making the first time as special as it can be. And how can I make seeing each other naked for the first time less awkward? Thank you for your time and I know your answers will help me extremely.

A: To answer your first question, yes, some women may find sex painful the first time. This can be caused by taking things too fast and not spending enough time leading up to sex — in this case we are assuming you mean intercourse, also called “penis/vagina” sex. Women’s vaginas create lubrication naturally, which makes sex more comfortable and pleasurable. Most women find they will not be lubricated — or “wet” — until they are excited or turned on. People are turned on by different things, but generally if you both take your time, enjoy touching or kissing or other mutually pleasurable activities — sometimes called foreplay — with each other, you are both likely to get more turned on and she is more likely to get wet.

For your second question, yes, many guys may come (ejaculate) quickly the first time since they are likely to be really excited. There’s no specific amount of time that is “too short” or “too long” for sex and you will figure out what works for you and our partner as you get more experience. Most guys feel excited and nervous about the first time they have sex. So do most girls. You can talk with your girlfriend about your concerns beforehand which is likely to lead to a conversation that can help you both feel more at ease.

And that leads into tips for making the experience more special. Talk to your girlfriend. Be open and honest with her and let her know she can do the same with you. Sex is not a race and it’s not a contest to see who can come first. It’s an experience of sharing intimacy and vulnerability. So have conversations with her and you can figure out what will make the experience meaningful for you both. Regarding the nakedness issue, we recommend going slow. You don’t have to take all your clothes off or even go all the way the first time. You can make out and touch each other, or practice oral sex to get to know each other.

PS- we’re eagerly awaiting an answer!

A: Using two different forms of birth control, i.e. the pill and condoms together can even further reduce your chance of pregnancy. Either one of these methods, used separately, can be over 95% effective, so combined they are quite effective indeed.

A condom may reduce your sensation a bit and prolong your ability to have intercourse without ejaculating. However keep in mind that as this is your first experience, what’s going on with your brain may be the most important variable. Also, you have not established a baseline to determine how sex works best for you. So it would be good to go easy on yourself and be open to trying a bunch of different approaches to figure out what works best for you and your partner.

There are lots of different condoms to choose from. It’s good to try a whole bunch of different ones to see what you like best. The size and shape of your penis might skew your decision in one way or another. Some of the world’s best-selling condoms are Durex Extra Sensitive and Crown Skinless Skin. Many condom companies give reviews of different condoms and user impressions of different styles so that you can better determine what might work for you. You could try condomdepot or condomwizard.

If your partner would like to help you pick out and put on the condom that could be fun! Just remember when putting on a condom to be careful not to scratch it with your nails, hold the reservoir tip to make sure there’s no air bubble, and make sure you put it on the right way, with the roll on the outside, so you can roll it down easily. If you put in on backwards, you’ll know because it won’t roll down easily, so just get a new condom and try again. She might even try putting it on with her mouth, that’s fun for some folks