SIB will be posting musings, advice, and her thoughts here on a weekly basis. Be warned, this IS a sex column and although there won’t be any steamy visuals (it’s not porn, ya know?) the text WILL be NSFW.

Happy New Year my lovelies! I know it is a month late, but better late than never, right? Have you missed me? My inbox certainly thinks so! Let’s get right to the nitty gritty and answer some of your more burning questions, shall we?

So, my partner has never masturbated. She seems to have a lot of yucky feelings associated with it. For better or worse, we both came to our first sexual experiences in a too young and wrong way. I’m not sure if this has had some affect on her feelings about self love, but it wouldn’t surprise me. I think we have a pretty good sex life; we both get off pretty much 75% of the time. We’ve never used toys, but recently purchased one. I’m looking for tips to make this first experience wow, not whoah.  

– Anonymous From Tumblr

I think it is great that you are willing to help her over this obstacle. Although it is a strong possibility that her mental block against masturbation is from what you described, I have learned that many women have issues and hang-up’s when it comes to this topic. In our society, at a young age, men are almost expected to start masturbating and exploring. It is the right of passage and the topic of many a teen movie. There is the wet dream, the masturbating to Victoria’s Secret catalogs, the quest to lose his virginity, and he is expected to be a strong, sexual being. However, women are raised to almost the opposite. They are taught to appear chaste and many are told that any self-pleasure is not only wrong, but completely evil. They are to be pursued, not to pursue. They are to stay a virgin and maintain their innocence and purity. This is something that can really mess with a girl’s mind. She comes to experience the sexual thoughts and urges just like the young boys coming of age, but she is instructed to repress, not to express them. That repression can instill shame and so many women as they get older carry this into their sexual relationships.

To start to assist your lover to be more comfortable with her own body, you need to make sure she is relaxed and establish trust. Since you are already dating and seem to have a healthy sex life, this shouldn’t be too hard. Begin to slowly finger her and tell her how she feels to you. Ask her to direct your touch to what feels best for her. Then, once she is getting more aroused, take her finger and along with yours, both of you keep fingering her vagina. Because your hand is still there, this might make it less mentally awkward for her. Tell her that her fingers can do just what yours can and that you want her to learn how to please herself. Let her know how happy it makes you to see her excited and satisfied. After a few times of “assisting” her in masturbating, she should feel a little less self-conscious.

As for introducing a toy, the most important thing when experimenting with anything new is to start slowly. Let her know that you want to share this with her, that it isn’t just about your pleasure and that hers is as equally important. Women like to know that you just aren’t out to get off or put your own kinky spin on something. We need to know that we are involved in your thoughts and your desires. As I have also stressed many times before, communication is critical. Talk with her, ask her what she likes or doesn’t like. Let her know how you are feeling as you watch her come closer to orgasm. Let her feel her own sexuality and power. Almost any woman needs that reassurance, no matter how confident we are in our daily lives. To overcome any mental block of sexuality, a woman, more than anything wants to be desired. If you can show her that you want her more than anyone else, and can reassure her that her comfort and pleasure are your main concern, I think your satisfaction rating will increase and you both will be able to enjoy sex that much more. Good luck! And, if you are comfortable with it, please let me know how things work out.

I really like this guy that I know who works with my best friend. We all go out to happy hours, dinners, and parties and the two of us always wind up hanging out most of the time and having great talks. We have a lot in common and get along great. We can also tend to flirt sometimes, but I then I things change and I wonder if he is really flirting or just being nice. He starts to really take an interest, complimenting me, joking about times we’ve spent together, etc. Just when I think that we may be moving to another level, he always brings up some girl he went on a date with, talks about how hot another woman who he sees at the bar is, or starts to flirt with someone else. Am I reading into this? Is he really interested in me?

-Confused in Canton, 30

Oh wow I wish I could tell you that I could read the mind of a man! They always say women are so hard to figure out, but men – you are no roadmap yourselves. Some guys are just natural flirts, and other times their flirting really does mean something. It could be as simple as he sees you as a good friend and likes to hang out with you and trusts you to confide in about his dating life and likes. If this is the case, you have fallen into the “friends” zone. Trust me, I am almost always falling into this one and it is next to impossible to climb out of. Once he sees you as the “buddy” or the “pal”, he more than likely is not going to want to move past that into dating.  Lots of us enter into relationships with the fear in the back of our heads, that if things don’t work out, we lose a friend. People don’t like to take risks like that most of the time. He could really be interested and just as nervous as you. Not their smartest move, but some guys brag about other women and their “options” to entice you more. They think it makes them look “studly” or desirable. They hope that we think that if so many other women want him, we will move in and want him that much more. For some women, I do think that may work. But for a majority of us, it makes us just as unconfident and confused as you are right now. As I wrote in the earlier answer, we want you to want us – not have a wandering eye or give us the insecurity that you could just walk away at any time and be fine with it.

I know it is forward, and not always in our nature as women, but if you really want to know where things might lead, sounds like you need to take some action. You can ask him out on a date. I know that can be hard for many of us and against our “dating programming”, but as the saying goes “You never know unless you try.” He may say no. He may be intimidated. It may make things awkward for a while. But you know what? You will definitely know and can stop wondering. And, honestly, do you really want someone who isn’t really into you or is intimidated by who you are? If that is something you just cannot do, a more subtle approach may be to step up your flirting. I’m not the best at flirting myself, so my tips are limited. But I do know that guys take active cues much better than smaller, non-verbal ones. Flipping the hair and batting the eyes may be great, but they can also be open to interpretation. Try when you are talking to touch his arm. Or find an opportunity to put your hand on his chest and look him in the eye. Give him the opportunity to know that you are interested and that if he makes a move, he won’t be shot down. After all, the flirting dance is mainly just a routine to avoid possible rejection, isn’t it? Remember, a stand-off has to happen by someone “backing” down first. Whether it is you or him that makes the move, it is much easier to do so when you feel like reciprocation is possible. Hopefully, the answer will be what you are looking for.


I’ll be back again soon, but feel free to ask away – I love answering questions and hearing your suggestions: and follow me on my blog, Tumblr, and Twitter.