So here’s the problem: I’m fine experience-wise with my own pleasure because of, you know, owning a vagina that’s at my disposal to experiment with, but I’m not sure of how to go about really basic manual and oral sex on the male side. My boyfriend is comfortable with (and very skilled at) giving both manual and oral stimulation, and I feel badly not properly reciprocating. I’ve given a couple hand jobs, but I feel uneasy about it, and not sure if I’m “doing it right,” which is one of those awkward questions I’d rather not ask my boyfriend while I’m trying to give him an orgasm. I haven’t attempted oral yet, and the thought of it makes me pretty nervous. I know people’s experiences differ, and that I’m just going to have to live and learn at some point, but I’d like some advice on how to go about things, especially on the oral side, and hopefully come close to giving as much as I’m getting.

A: The best advice we could give you on how to please your boyfriend is to ask him. Seriously, even really experienced people need to ask their partners what they like because every person is different. So as you are doing things, ask him questions like, “is this good?” “should I go harder?” “do you want it faster?” etc. Also, it could be that your partner likes answering your questions. It can be really hot for some people to get to “show you the ropes” and teach you the way they like things. Think about it- would you mind answering questions about how you like to be pleasured? Probably not, if it means your boyfriend is better at pleasing you!

That being said, we do have some general information on what many guys like for oral sex. First, be careful with your teeth- try not to scrape or bite him. Second, the head, specifically the underside of the penis towards the top, is the most sensitive part. Many guys like to have this area licked, massaged, or played with. For some, however, this part will be too sensitive, and too much stimulation could irritate your partner- which is why you have to ask him.

Another tip for oral sex is to not try to put his entire penis into your mouth. It probably won’t fit, and you’ll probably just end up choking on it (not so sexy). So use your lips, tongue, mouth to lick and suck a little along the sides or around the top and use your hands to stroke his shaft where your mouth is not.

For hand jobs, the general idea is just to stroke his penis, much like he would if he were masturbating. The best way for you to learn how to do this is probably to have him masturbate in front of you (try asking him to touch himself for you), then try to duplicate what he does. In general, though, you want to stroke him up and down, slowly at first then faster as he gets more turned on. Lube can be really helpful with hand jobs because less friction = more pleasure. Ask him if he wants it harder or softer, faster or slower.

You can also try playing with his balls, either by licking them or gently rubbing them with your fingers, either as part of a blow job or a hand job.

You might also try looking at Very Koi, which has some tutorials for masturbation and oral sex. It might have some ideas or tricks you could try.

A: You will notice very little difference between a cut and uncut (circumcised and uncircumcised) male penis as far as you are concerned. The foreskin consists of the same skin that is on the head of the penis that folds over part or all of the head when the penis is flaccid (soft) or folds onto the side of the penis during erections. There are nerve endings in the foreskin that are also similar to the nerve endings elsewhere on the penis so this skin is sensitive and can be the source of added pleasure for the uncircumcised person.

The main difference has to do with hygiene as it relates to the uncircumcised penis needing more attention than the circumcised penis in cleaning and keeping the area clean. The area of skin around the head of the uncut penis can tend to have a stronger odor at times than the cut penis if the hygiene is lacking.

There are a few other things to know about the uncut penis such as some men prefer to have the foreskin pulled back prior to receiving oral sex and/or putting on a condom. Also, lube can be even more helpful on the uncircumcised penis, either with or without a condom, to reduce the amount of friction between the loose skin and the rest of the penis.

My problem: I can’t seem to have sex. There are both physical and psychological factors. Trying to have sex really hurts. Insertion is extremely painful. Before I started getting naked with my current boyfriend, I hadn’t inserted anything at all, ever. Over the course of my current relationship, I’ve been able to allow painless insertion of his finger (or mine), which is great… but I still have a pretty intense fear reaction if he reaches for my vaginal opening. Fingering is OK for me, as long as I know exactly when and where it’s going to happen, which is really annoying. Even when I do know, it’s still scary for me, even if I’m not experiencing any pain.

As for actual sex… I don’t know, the idea just scares me. And like I said, trying is really painful. I’ve tried SO hard to just “get over the pain” and go for it, but it’s seriously overwhelming and reinforces my fear response every single time I try. It’s the most frustrating thing in the entire world and it makes me feel totally sexually inferior and it just really, really sucks.

So you’re probably thinking that I’ve either experienced some sexual abuse, or I need to go to a doctor. Well, I haven’t been sexually abused, and I’m petrified of going to the doctor, because god knows what they’ll do. I can’t endure a pelvic exam, it simply hurts too much, and I realize that going to a doctor will likely involve a pelvic exam, and I simply can not do that right now. I’m looking for some alternative help.

And yes, I’ve looked into vaginismus. I’m not sure that it’s exactly what I’m dealing with here, but it well could be. If it is, I need a free and confidential way to deal with it because I’m an extremely broke college student, and while I have health insurance, it’s my parents’ plan, and they’re certainly not advocates of sex before marriage but I want to have sex, I’ve wanted to have sex for a while now, because I’m in love and in a healthy relationship and I really think I’m ready… I just can’t seem to do it!

Any advice or resources you can share?

Thanks so much in advance… and for reading all of this. I certainly don’t mean to sound so angry but this is a daily struggle that is really having an adverse affect on my life–and while my boyfriend is extremely supportive, and even encouraged me to write this e-mail, believe me… he’s not a fan of it either! HELP!

A: Thanks for writing with your question. It sounds like a frustrating experience!

The first thing we want to stress is that a visit to your doctor should not result in an automatic (and possibly painful) pelvic exam. Ideally, you would be able to see someone who will be able to deal with your issue appropriately, i.e. by listening to your concerns and proceeding in a way that will help you figure out the problem. As a patient, please do advocate for yourself! You have rights during a doctor’s visit: when something hurts, you can say “stop,” and you can also ask to see a different physician. This can be a hard thing for people to remember, but it’s important!

I doubt that information can get from your doctor’s office to your parents, unless you see a physician your parents know. Health insurance bills aren’t usually detailed. Plus, there are plenty of good and perfectly legitimate reasons for a young woman– sexually active or not– to be visiting a gynecologist. You mentioned that you’re a college student– is there a clinic at your college that you can visit? Can you bring a friend with you to keep you company and to help you remember to self-advocate?

It sounds like you’ve already contemplated quite a few of the possibilities, from the physical to the psychological. The fact that there’s been some “painless” insertion of fingers is a sign that vaginismus might not be what’s going on, although we cannot diagnose that from here!

There’s a long article on the excellent Scarleteen website called “From Ow to Wow! Demystifying Painful Intercourse“, and it mentions a few things that might be useful to you: first, especially, that “any kind of sex shouldn’t be about a lack of pain, but about the presence of pleasure.” Are you “warmed up” or aroused enough when you’re trying to have sex? I understand that the combination of fear of the pain can be a powerful counteracting factor. It’s possible, too, that his penis might be too large for you, or that you need more warm-up (with a finger or two) before trying the insertion of something larger. Points number 5 & 6 ask about sufficient lubrication and anatomy, and number 7 talks about the psychological factors, which I think might be especially important for you. You might want to consider their advice about seeking counseling (again, does your college have a counseling clinic? many of them do) in this case.

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