I Can Only Orgasm Squeezing My Legs Together

Profile picture for user Betty Dodson

Betty Dodson

Hi, Betty.

I would first like to say that I LOVE your website. I'm 16 and have always had a lot of sexual curiosity and I love when people, like yourself can speak freely about a topic that has, unfortunately been so down played and criticized by our society. Thank you and Carlin for all you do.

Now, I have been masturbating since a very young age. I started at about 5 or 6 when I discovered how good the sensation of squeezing my legs together felt. I have been masturbating for about 10 years now, but always with that same technique. It wasn't until I was about 14 that I started playing with my hands, but even though it does feel good, it can only get me to the point right before orgasm and then the sensation sort of plateaus and I won't reach orgasm, which prompts me to switch to my original form of self pleasuring until I orgasm. I love my orgasms, don't get me wrong but I've always known that the amount of pressure it exerts would be difficult to recreate with a partner.

I was right. I recently started having sex for the first time with my boyfriend. Though sex is really great and we're both very comfortable around each other, so we play around with things, I can't orgasm. Not through fingering, oral play or vaginal penetration.

I don't like girl on top positions as they do nothing for me (not enough pressure) and I'll get close to orgasm (like when I pleasure myself with my fingers) but I won't climax during other positions (missionary is greatly underrated, I love it). Sometimes it's not so bad when we're done and I can deal with not having orgasmed, but sometimes I am very frustrated and annoyed and get really irritated afterward.

It affects him too since he hates that he can't make me climax. It's starting to be a problem, and I know that stressing over it won't do anyone any good so how can I wean myself from my regular technique and start to have orgasms through manual masturbation and of course, through sex? I've read your "How to Masturbate" blog and have tried it out, but it doesn't seem to work. I can get close, but won't orgasm.

I also own a vibrator. Also really good, but won't "finish the job", for lack of a better expression. Please help. I love my boyfriend and I love orgasms. I would ADORE to reconcile the two. Thank you! :)

Sincerely, D

Dear D,

Ah the impatience of youth. My Darling Girl it takes time to change an ingrained habit of any kind, especially your long term masturbation technique of ten years! Next read Upgrading Your Masturbation Skills. It can be found in the left hand column. Also check out my other essays under Sex Features on the Navigation Bar. You are doing great. You just need to keep practicing and you will get it all together at some point.

Thanks for all your love and appreciation.

Dr. Betty