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: There are several ways you can bring up the topic. For instance, it might be helpful to playfully bring up the subject during a neutral conversation moment so not to put pressure on him during your time being sexual. You could say something like, “Sweetie, let’s talk about sex and ways we can maybe spice things up.” Or, you could ask him if he has any sexual fantasies that he would be willing to share with you to get a sense of whether this might be something he is interested in and hasn’t known how to bring it up with you. Even if he doesn’t have that specific fantasy, it would be a good lead in for you to share about having a fantasy about spanking.

As another alternative, you could rent a movie containing the subject (”The Secretary” is a good Hollywood movie) and have a discussion about it afterwards, asking your partner what he thought, and if he might want to try something like that.

There are also plenty of rentable adult films that deal with spanking. You can look online at places like bluedoor.com (kind of like a Netflix for porn). And there are instructional type videos such as “Nina Hartley’s Guide to Spanking,” and other DVDs on Amazon.com (search for “spanking DVDs”).

In looking around on the web, here’s an interesting blog about spanking. Perhaps you can share some of this with him, or make it a topic of discussion.

There is another article about men spanking women written by Dr. Victoria Zdrok that you might show him if you are interested in him spanking you. If you are interested in spanking him, you might want to both check out Spank Your Man.

If he is interested in the spanking, you might want to take it slowly with the spanker spanking the spankee’s bottom and the spankee saying a number between 1 and 10 to communicate intensity. That way, the spanker can get a sense of connecting how s/he swats with the spankee’s experience.

Good luck!

A: It’s quite likely that the girls you’re having sex with do not know that your penis is unpleasantly sensitive right after you ejaculate. It’s possible that no one’s ever told them, and that they’ve had other partners who enjoyed being stroked post-orgasm–as some males do. My best advice for you is to tell them yourself. It might even be a good way to start a conversation about ways they do or don’t like to be touched that you might not know about.

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: Everybody is different, and it is hard to tell what this particular boy will think, if he even noticed it all. However, this should definitely not discourage you from talking to him or being his friend. Many boys are super impressed with girls who know what they like and are comfortable with seeking it out. It can make things a lot easier for both you and the guy you are with if you already have an idea of what you like. You are definitely entitled to your own sexual preferences, idea, and thoughts, and it is always a good thing to be open and assertive about them. If you find pressure from somebody about what you like, it does not at all mean that you are doing the wrong thing.

Even though this might feel quite embarrassing now, it should not have to impact how you interact with him.

He always was easy to turn on, and so never dealt with pleasing a woman when he wasn’t. Now he’s with me and I’m still, in my late 60s, substantially sexual. He’s thinking about whether he can get into pleasing me when he’s not aroused. I’m wondering what your advice is on this and I look forward to hearing from you. I am concerned that he will leave me hanging when I’ve got miles left to go my thinking is that each of us, whatever our capacity, should be filled up by the time we quit, but I don’t want to have to pull him to get what I need.

A: First we recommend you talk to him about your needs and your desire for him to participate in fulfilling your needs. People participate in partner sex for many reasons. Some people just want to get their own needs met and may not have previous partners request more. You may want to suggest he works on getting you off before you do anything to get him off. You may tell him all the things you will do to him right after you get off. Many men get excited by hearing dirty talk, but still need direct stimulation for orgasm. If you engaged in vaginal/penis sex you may experiment with different positions. Rear entry while on the side on a spooning position frees one of his hands to provide direct stimulation to your clit. You may also want to consider bringing a vibrator into your play together. Many women find that they can get off faster with a vibrator thus matching his need for shorter play. You may ask him to use the vibrator on you. If he is still reluctant, you two may want to considered couples counseling.

A: Many people enjoy watching porn that involves sex that they are not necessarily interested in, and porn definitely falls within the fantasy realm. Some straight men will even watch gay porn even though they do not want that type of sex for themselves. You do not have reason to worry, because since your boyfriend is with you, then you are the type of woman that he is attracted to and wants to have sex with.

We would suggest checking out porn selections for yourself and exploring the different kinds of porn available that glorify women that are similar to yourself. This could help you with any insecurities because you will see tall women/ women in their 30s in sexy situations, etc. If you bring home a porn selection that you want to watch with your boyfriend, he will probably be happy to join you.

Here are a couple links to give you some ideas:

Violet Blue’s Smart Porn

The Goodvibes video selection

A: The best (and really only) way to know if someone is satisfied in bed is to ask directly. There is no noise or facial expression that means the same thing for every person. Communication between partners is very important. Tell him how you’re feeling in words, and ask the same of him.