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How (and why) to Root for Team Awkward

JanFirst2011 asks:

I am 15 years old and I have only made out once. I do not know the person I made out with, and I don't exactly remember what it was like. I want to make out with more people, but I am afraid I will not be good at it, I also don't want to embarrass myself with the person I do make out with. Another thing is, what if the person I do make out with tries to do more with me than I am ready? What should I do and how do you recommend getting over these fears of mine? Thank you!

Letting Go of the Wrong Stuff to Get a Hold on the Right Stuff

Kyra asks:

I am 22 years old and have been with my one and only boyfriend for over 2 1/2 years now. I love him very much and we get along well, but our sexual life has always had problems. These are the main issues: 1) I cannot orgasm except through the use of a vibrator, 2) I'm often not interested in sex/don't really feel anything enjoyable from sex, and 3) I never initiate anything, which makes my boyfriend very frustrated. We've been having sex for about 2 years now, and these issues are as much of a problem as they were when we first started. Regarding the problem #1 (no orgasm except with vibrator), my boyfriend has tried everything. He will pleasure me for long periods of time, try to make me feel sexy, but NOTHING happens--I don't even come close to orgasming (in fact, I usually just get sore from the contact). I've tried to pleasure myself, but this is even worse--I hate the feeling of masturbating and don't derive any pleasure from it. When we discovered that I CAN orgasm via a vibrator, we were both thrilled; however, it usually takes me a good 15-25 minutes to orgasm from the vibrator (on the highest setting), and the orgasm usually lasts only a few seconds--it just feels like a lot of work for barely any result to me. Because I'm not interested in sex very often and I cannot orgasm via penetration or manual stimulation, my boyfriend believes I'm not sexually attracted to him and is quite upset. I don't know what to do and it is ruining our relationship. I am religious and come from a home schooled background where sex was not talked about much, and so I often feel awkward when my boyfriend tries to discuss it with me (and going to a sex therapist is out of the question).

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