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Q&A: Problems with Penetration


Terribly sorry to bother you, I know you get a lot of emails and messages, but I really love your videos and they have helped me a lot, so I thought you might be able to help me with my situation and I couldn’t find the answer to my question in any of your videos.

To be blunt, my boyfriend has a rather large penis (7.5in, 2 in.wide), and I’m a very small female (120lbs), and we have been having problems in the bedroom. We are probably the most intimate couple I know, completely in love, and after a long wait we decided that we wanted to have sex. We’re both virgins. However, whenever we try, he cannot penetrate. I know that it is not a matter of our comfort level, both of us want it very much, and I get wet, but he can never penetrate more than an inch without me experiencing extreme pain. So I guess you could say we’re having problems with penetration. Inserting tampons larger than regular size is even uncomfortable for me. We have tried multiple times with various condoms, and I am aware of the fact that the first time will hurt, but I was wondering if you have any suggestions, like positions we could try, or products we could buy to make it less uncomfortable for me, or any other advice you might have.

Would it be easier if we “practiced,” as in, he tries to penetrate a little more every time? Or would that just make the pain worse? Should I use a toy, or would that just be silly?

Thanks for your help,

Worried First Timer



Dear Worried First Timer,

Thanks for watching and supporting what I do!!

What your are experiencing is very common and something I hear all the time. That being said, please be aware of the fact that it is normal, to be expected and nothing to be ashamed or embarrassed about.

As for suggestions, I think you should start small and then work up to an actual penis. There are many things that you can use that are smaller then him that will help your body to stretch (it won’t actually ‘stretch out’, so don’t worry about that), get accustomed to having something inside, as well as hopefully provide you with the stimulation you need to have an orgasm.


First I would suggest making foreplay a very regular and integral part of your experience. I say this because the more aroused you are the more your vaginal canal will expand to allow the insertion of a penis. Just to be clear, when the vaginal canal at its largest (fully expanded) it’s “usually” between 6″ – 7″ inches deep, whereas it’s normally only 3″ – 4″ inches deep. Crazy, I know. Unfortunately, more foreplay doesn’t equal a deeper expansion.

Foreplay doesn’t have to be anything specific, just whatever it is that turns you on in the moment. For some people it’s cuddling, others like talking dirty, some like watching porn, others prefer something more external like light caresses, massages, or spankings. Feel what’s right for you in the moment, it’s all about turning yourself on.

Also by making foreplay a regular part of your experience you allow your body to go through the natural response cycle of arousal, allowing you to lubricate and ready yourself for intercourse.

Start Small and Go Slow

Next, I would suggest either using a finger or a small silicone dildo to get yourself used to the feeling of having something inside. This can be done by him or by you. I’d personally suggest a dilator set, they often have everything you need, starting with smaller sized dildos and graduating to much larger. Or if you’re looking for something more specific I’d say go with a Small Silk, Little Flirt, or a Tantus Meteorite (my review) the last one is meant for anal use, but can just as easily be used vaginally. They’re all relatively small, made of body safe materials, have a base so you can get them out easily, and will last you a lifetime.

As for using them, I don’t suggest you just try and cram them in or go for an instant thrusting motion as it’ll likely be painful. Instead, lube both yourself and the toy up, then when you’re ready slowly insert the toy until it starts to hurt and when it does… just stop. Don’t remove it or shift it, just leave it exactly where it is. I know this may seem a little silly, but as time passes your body will relax and you’ll find the pain will subside. When you’re ready insert a bit more until it hurts, again, just stop. Keep going like this until the toy is completely inside you. For some people this takes one session, for others a few days of practice, some are able to do it on the first go. There is no barometer for what’s right or wrong. Just take your time and go slow. Eventually it will far less painful and something you can learn to enjoy.

Once you’re comfortable with the toys, try having him use his finger to penetrate you. I realize that it still might hurt, but using lots of lubricant and relaxing can make a world of difference. Again, I don’t suggest that he use his fingers in an “in and out” motion as the friction can sometimes hurt, but instead place that he slowly insert one in you for as long as your comfortable.  Follow the same steps outlined above until you’re comfortable and ready to explore something larger like two fingers. From there you could attempt a larger sized dildo or have him try and penetrate you. Again, it may still be painful but usually if you’ve taken the necessary time to allow your body to get used to the feeling, it can make a world of difference.


The final suggestion I have is to take some time relaxing before you have sex. The more relaxed you allow your body to become the more you will enjoy the experience because you are not tense, and therefor not “tightening” up.

Please remember that it isn’t something that is going to happen over night and instead is going to take some time for you to get used to. That being said, once you are comfortable and ready it can make the experience a much more pleasurable one then a painful one.

I do understand how frustrating this can be and hope that some of my suggestions helped.


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Sex Ed 102 Q&A: Help! I Can’t Orgasm


Hi Kara Sutra,

I just wanted to ask if maybe you could tell me what’s wrong with me; every time I have sex with my boyfriend I can’t climax.  I can have them on my own… just not with him. Help! I can’t orgasm, and I’m really starting to wonder what’s wrong with me?


What you’re facing is unfortunately very common.  So let me first just put it out there that there’s nothing wrong with you and it’s not any ones fault. Most women have had at least one (if not a handful) of occasions where they aren’t able to climax with their partner, men too. It’s normal, natural, and nothing to be embarrassed by. It’s just part of being sexually active.

Before I offer any suggestions, I’m going to throw out a few scenarios as I find it can be helpful to think outside the box when addressing issues like this.

Solo Sex vs Coupled Sex

You said you can come on your own, but not with him, maybe it’s a case of nerves, maybe you don’t feel totally relaxed, maybe you’re scared you’re going to look stupid, either way what you’re going through is pretty common. Let me explain…

When a person climaxes during intercourse it requires being in a position where they’re comfortable, feel safe, and trust the environment, and/or person they’re with, not to mention being comfortable in their own skin and/or the way their body will behave.

Although this isn’t always the case, sometimes our bodies do things we can’t control when we orgasm – convulse, make faces, twitch, say embarrassing stuff, flail, shudder, squirt, scream, shake, tense up, go limp (to name a few) – and no matter how hard we try, we just can’t stop that from happening. Allowing someone to see us ‘out of control’, for lack of a better term, requires vulnerability and courage. Two things that can be very hard to muster up when we already feel exposed.

When we masturbate, things are usually quite different; most people ensure they’re in a place where no interruptions can happen, that they’re secure, and the worries they have are limited; they aren’t scared someone else will get soaked if the squirt, that they’ll be laughed at for the look on their face/something they do or say in the heat of the moment, or that they’ll be judged for they way their naked body looks. Basically, there’s limited to no risk of embarrassment when masturbating, allowing us to let go completely, which definitely helps with achieving an orgasm.

Throw another person into the mix all sorts of embarrassing situations present themselves.  Often times we’re not even conscious of this and enter into sexual relations unaware, only to end up disappointed.  This isn’t to say that we’re not comfortable with our partner(s) or that we don’t love him/her.  It has more to do with the conscious/unconscious state of being and the willingness to share a very intimate and personal experience.

One thing I’ve come to learn from most women is that once they have had a self induced orgasm in front of their partner where nothing “bad” happened, they are better able to achieve an orgasms with them next time around.

With that in mind, I suggest you take a night where you both masturbate for each other. I’m serious. Relax and allow yourself to have an orgasm in front of him. Try not to be embarrassed or afraid to let go. Don’t rush, take as long as you need.  Do it for you and you alone. Use whatever toy you feel works best and that you love to personally play with. If it helps, just pretend that he isn’t even there. Sit him in a corner by himself in the shadows and do all of the things you would normally do for yourself. Whether it’s lighting candles, playing music, fantasizing about a male/female you are attracted to or putting on your pajamas. What ever you do when you are by yourself, do that.

I know it’s probably a scary, overwhelming, intimidating, and bizarre idea to throw out there, but if you trust your partner, self, and want to get past any issues you might be having it’s worth trying. What’s the worst that can happen? …you’ll have an orgasm, might do something embarrassing, he’ll make you feel better about it, and the next time you’ll both know what to expect. No biggie. Trust me, if he loves you and wants to see you happy, he’ll do whatever it takes to make you feel comfortable in your own skin.

Other Suggestions

For as hard or uncomfortable as it might be, talk to your partner about your insecurities and the things that make you feel vulnerable in the moment. If they understand where you’re coming from they may be willing to help you explore and feel confident in your skin.

Try using toys during sex. It is VERY common that most women can’t achieve an orgasm without the clitoral stimulation that a penis can not provide. By introducing toys during sex you create the much needed stimulation of the clitoris.

You also might want to look for a more powerful vibrator like the Hitachi Magic Wand as it may be “harder” for you to reach the level of arousal you need from clitoral stimulation to achieve an orgasm. Keep in mind that not everyone is built the same, so what might take one woman 1 minute of stimulation to reach an orgasm might take another 10 minutes, a half an hour, or even longer.

When it comes to sex there are certain “levels” within the a persons Sexual Response Cycle that need to be reached in order to achieve an orgasm. You may want to watch my video on the subject in order to learn more about your body and the way it’s reacting, so that you can understand what’s happening and hopefully figure out what you specifically need to do.

Finally, stop trying. One of the main problems that people face when achieving an orgasm is that they forget to relax and enjoy it. They stress themselves out about and end up not being able to allow it to happen naturally. Remember, sex is supposed to be fun not stressful.

It may take more then one go at it, but with time if you are able to relax enough to let go and surrender to that primal part of yourself, you should be able to reach an orgasm.  Enjoy it!

hope that helped


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