A Big O – From First Orgasms to Multiple Orgasms

I was seventeen or eighteen when I discovered how to bring myself to orgasm. I remember I was so excited about it that I called my boyfriend and told him every detail. Then, when I got off the phone, I did it two or three more times before falling to sleep.

I was hooked. Orgasms were great! I looked forward to every night when I'd get to lie in bed, on my stomach, with my fingers doing their thing between my legs. It took forever for me to figure it out. I read about it, I read about sex and masturbation and orgasms. I'd felt arousal and I'd given my boyfriend handjobs. But my body, my own ecstasy, was a mystery to me. I remember laying in bed and getting o frustrated with my body that sometimes it would bring me to tears. I wanted release, I needed it, and once I discovered it, I treated myself at every opportunity.

What had I been doing wrong all those years? I'll tell you: I thought sex, and therefore orgasms, were all about penetration. I tried candlesticks, hairbrush handles, even eyed the cucumber longingly (but never tried the vegetables, too many chemicals). Then I read online about this magical little nub called the clitoris. Mostly what I read was about how men had so much trouble finding it. I had absolutely no trouble finding mine, and when I did find it, I quickly discovered that it was way too sensitive to touch directly. It wasn't long before I was working around it, trying to find the rhythm and pressure needed to get me over the edge.

Imagine my surprise when I discovered that an orgasm was something I'd been giving myself when I was a little girl! I recall laying in bed at night and tightening my kegel muscles because I liked the way it felt… and the more I did it, the better it felt, until it was like they were tightening on their own—tight, quick, hard, making me shudder and quiver in bed, biting my pillow. When I experienced my first orgasm through masturbation in my late teens, I remembered the feeling as soon as I had it. Why didn't I realize–!

Ah, well, here I am today. My masturbation technique has not varied too much over the years. My preferred method is still laying on my belly. I can use either hand, or both. Sometimes I slide my fingers inside, but it isn't what gets me off, and I usually don't do it at all. I begin slow, just thinking sexy thoughts as I rub my clit from the side. Slow and steady in the beginning as whatever scenario I'm imagining builds up. As I get wetter, I increase the tempo and pressure, but always from the side, never directly. When I come, if there's no one home, I'm loud. I ride the waves of my climax as long as I can keep it up, milking it for all it's worth. Then, once I'm done, either I go right to sleep, do it again, or clean up and go about my business.

I am still the only person to give myself a clitoral orgasm, though in recent attempts, Kitten has come very, very close. She's learning to read my body language and respond to it, and I find myself clinging to her and gasping as her touch sends electrical currents down my spine, tightening my whole body, but only climbing and not yet toppling over the edge. My inability to achieve orgasm has been a sore point for her, because she doesn't like that I can give her climax after climax, but she can't repay the favor. It makes her feel inadequate, and in turn makes me feel like I'm failing somehow.

We are not so ready to give up, though. We have been talking for some time about buying a dildo and harness, discussing options and sharing ideas about it. Though I know for sure I can come via other methods besides vaginal intercourse (with a real or fake dick), it's one way that is almost certain, so she has been wanting to try it. I have a vibrator at home that is insertable, and I asked her if she wanted me to bring it over so we could experiment with it.

Yesterday, we did just that. We started off with me on my back, and she leaned over me, kind of holding the dildo in the general area where it might be if she were wearing a harness. I like the closeness and I prefer her to be within kissing/licking/biting range during sex, and I thought it was hot anyway (that my girlfriend was going to be fucking me with a cock). Once I was wet enough, she slowly started to work it inside of me. This toy is bigger than what I'm used to, and it took some time for my body to adjust around it.

I realized that I am not able to orgasm on my back during intercourse, so we switched positions, me straddling her hips and she held the dildo as I lowered myself down on it. I have to say again, that thing was big! And it was still an effort to slide down onto it. But, in this position, I am more in control and I am more “at home.” I felt the familiar waves of pleasure washing over me. I got so excited, realizing I was going to come for her! My toes curled up and finally the orgasm came, vibrating through my body, making me shake, making me cry out.

This is not the best nor the most detailed description I can give of this event, but I'm still a little high from it (and, well, it's a personal account!). I am still just so happy I could give this to her. And I'm so happy that I can kind of let go, let my body relax and just feel her and feel the pleasure she can give me. This is just another step closer, another step into my relationship with her, and I can't wait to see where we'll go next.