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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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Can you get pregnant if…

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Sex Ed 102 Q&A: Can You Get Pregnant From Anal Sex?

For all of my viewers who have sent questions regarding this subject I thought I would finally answer it in video format so that there is no confusion.

Can you get pregnant from Anal Sex? – For the most part no, you cannot. However nothing is impossible.

Yes, but it is rare. If semen or pre-ejaculate (pre-cum) comes into contact with the opening of the vagina or the vulva, the sperm may survive and travel up the vaginal canal, through the cervix, uterus and fallopian tubes. If a girl or woman is ovulating, or about to ovulate, there is a possibility that the sperm can fertilize an egg in the fallopian tubes, resulting in pregnancy. The best way to keep sperm from fertilizing an egg cell is to make sure that no semen gets below the belly button or above the thighs.

Quick Anatomy Lesson

The anus is part of the digestive system which begins in a person’s mouth, and ends with the anus. Since the reproductive system and the digestive system are not connected, sperm that enters anally cannot swim through the body to reach an egg in the reproductive system. Pretty straight forward, right?

That said, you CAN get pregnant from the after effects; if  semen or pre-ejaculate seeps, leaks, or drips from the anus and manages to make contact with the vulva/vaginal opening, there’s a chance the sperm can survive and make its way up the vaginal canal, through the cervix, uterus, and finally end up in the fallopian tubes, and if the person is ovulating/about to ovulate, it could theoretically fertilize an egg.  Again, the likely chance it would happen is minimal.

To minimize any chance of this happening, I’d suggest you engage in safer sex practices like using a condom during anal intercourse.

With so many b.s. myths floating around I’m stressing that you please take this opportunity to learn about your bodies, how they work, the reproductive systems of the female and safe sex so that you can answer these questions with common sense based on the information that you already have.


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Sex Ed 102 Q&A: Can you get pregnant from oral sex?

can you get pregnant from oral sex?I’m not sure exactly where this one started, but one of the questions I’m asked far to often is, can you get pregnant from oral sex?

The short answer, no.

Brief Anatomy Lesson

In order for a pregnancy to occur, sperm must make its way into the vagina, travel through the cervix into the uterus, and make contact with an egg in the Fallopian tubes. Because the digestive system (starting at your mouth and ending with your anus) and the reproductive system don’t meet in the body, there is no way for sperm to swim through one system to the other and make contact with an egg.

Having said that, although getting pregnant isn’t possible with oral sex, contracting a sexually transmitted disease like gonorrhea, chlamydia, syphilis, warts, herpes, or HIV is.  To keep yourself safe from an unplanned pregnancy or STD, I suggest using a condom no matter what type of play you’re getting into, including oral, vaginal, or anal. If you choose to go the route of cunnilingus, I’d suggest using a dental dam to protect against STD’s.

If the taste of latex isn’t your thing, there are flavored condoms and dental dams made specifically for oral sex.

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Sex Ed 102 Q & A: Threesomes


Hi Kara_Sutra,

I have a question to ask, my boyfriend and I have been talking about having a threesome for his bday and I’m still not sure because in a way I think it might ruin our relationship. What are your thoughts on this?


First off thank you for watching and supporting what I do!!

In regard to the threesome question, personally I think that is a conversation you need to have with your partner. It is very common for couples to want to experiment or toy with this idea, however though it can be fun in the moment, if not handled properly the after effects can be very damaging.
There are a few things I suggest;
1.) Make sure that there are rules…and that you STICK TO THEM.
Threesomes are something that in order to happen safely, and with out repercussion, there needs to be a level of trust and honesty between the couple. By clearly defining what the rules are and sticking to them allows you to decide for yourself, and as a couple, what you are personally ready for and willing to experience. If you agree to have rules and you DO stick to them, the couple usually doesn’t have such a hard time with what happened because the level of trust was respected by not being broken or ignored during the act.
2.) Talk about your fears with each other.
Again, there needs to be a level of trust present before the couple brings a third party into the mix. By talking about your fears you are able to clearly express why you may not want to experience a threesome and allow your partner to understand where you are coming from. It also offers them the opportunity to reassure you and you to reassure them of the strength of your bond. In some cases when a person openly expresses their fears with another they are presented with the opportunity to face them in a safe environment that is free of judgement.

3.) Make sure you use protection at all times.

By this I mean that any time a bodily fluid is transferred between any partners you have a barrier. Whether it be dental dams (and or) condoms (and or ) female condoms, ALWAYS practice safe sex. You never know who has what, and sometimes it takes a while for a positive result to be shown on a test. Just because a person was deemed a clean bill of health this week, it doesnt mean they will be next week. Another thing that I want for you to make sure of is that everytime you change partners, the barrier also changes…what I mean by this is if you are having intercourse with your partner and he switches to having intercourse with the other party, that the protection also changes, otherwise you he may transfer something from you to the other person and vise versa.

4.) Make sure that the other party is someone you both trust and feel safe with. Also make sure that the other person is someone that will NOT be a threat to either of you or your relationship after.

5.)Decide 100% for yourself that you are willing to go through with it.

Its funny the level of pressure we can feel from a partner when they want something. Its also funny how often we comply, even when it is something we dont want to experience ourselves. Most often our thoughts are consumed with wanting to make the other person happy, sometimes its due to our fears of loss, sometimes its due to our own insecurities, and other times its because we are selfless individuals. Whatever reason you may think of that is propelling you into this experience, make sure, 100% sure that it is something YOU want to explore and experience. Otherwise you may be very upset with the after effects and the damage it can cause to not only your relationship, but YOU. Please also keep in mind that if at the last minute you dont want to go through with it, that it is OK. Don’t do it!

6.) Talk about it after.

One thing that most couples do after they have an experience like this is shut down. They don’t talk about it or offer any information to how they feel. They instead bottle it up and keep hidden away from themselves and their partner. This is not healthy and can be very dangerous to your relationship. My suggestion is to make an agreement before hand to talk about it after, no matter how hard or overwhelming. Just talk about it. This gives you both the opportunity to reaffirm your bond and deal with any issues you may be facing both as a couple and with yourself.

That’s pretty much all I can offer in regard to my suggestions or thoughts on the matter. I hope that it helped in some way and maybe gave you some insight to the way things may either get better or fall out after.

Hope it helped



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