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My First Orgasm

I was twenty-seven the first time I was able to achieve orgasm with another person.

‘Achieve orgasm’ — a funny way to phrase it, but that’s honestly what it felt like at the time: a real thank-you-god finally achievement. It was a damn good one too, the kind where you curl into yourself and can’t help making those small staccato whines as your pussy throbs once, twice, thrice — clenching tight in a rhythm you can’t control, your clit so sensitive you squirt a little and it feels like your whole body is lit up bright enough to see from space.

I remember I cried a bit afterwards. A little because the feeling had been that intense, but mostly out of sheer, overwhelming relief.

Relief that I was actually capable of coming during sex and not just through masturbation.

Relief that there wasn’t anything wrong with me.

Ten years after the first time I had sex — not to mention two long term relationships and four Tinder hookups later — I was finally, finally able to climax because someone else brought me there, and not because of my own hand.

Incidentally, it was also the first time I ever had sex with a girl.

I met Diana on a Saturday night at a friend of a friend of a friend’s party. Honestly, I can’t remember much about it—not who invited me and not whose party it actually was. There were a lot of people though, I remember that much, and the whole bar was full of twenty-somethings getting drunk and flirty with each other.

I was letting a guy chat me up near the bar as I waited for my next drink, smiling and laughing at—whatever it was he was saying to me, because that’s what you’re supposed to do, when you’re a single girl at a party, right? I was trying to decide if he was cute enough to go home with or if I should cut him loose after I got my drink, when someone squeezed in beside me to grab the bartender’s attention.

“Sorry,” the woman said, raising her voice to be heard over the music and general bar noise, tilting her head a little to meet my eyes with a smile. “Hi.”

My first thought when I saw Diana was: wow, okay.

I’m not sure how long it took for us to end up in Diana’s apartment, from that moment we met in the bar. It was a gradual thing: we started talking, I got my drink, she got her drink, not-cute-enough guy got left out of the conversation and eventually shuffled awkwardly away, and somehow we ended up stumbling out into the street and walking the two blocks Diana said it would take us to get to her place, laughing and having a very spirited conversation about how we both really wanted to like the new Star Wars movies but just can’t.

Except for Rogue One, we agreed that one was excellent.

I think it was a little bit past midnight when I fell face first onto her couch, giddy and giggly from more than just the three cocktails I had in the bar. Later, I would realize that it was because I had found a kindred spirit, someone who would take my jagged edges, smooth them out, and fit beside me.

But I didn’t know any of that at the time, all I knew was that I liked Diana: her pretty, heart shaped face, her ink black hair, curling and wild around her shoulders, and her dark, laughing eyes. She looked—beautiful, and genuinely happy with her life.

Not like me.

Yes, I do have a really unattractive habit of suddenly turning maudlin and weepy when drunk, why do you ask?

“Hey,” I heard her say, and a moment later felt gentle fingers combing through my hair. “It’s okay.”

Not ‘are you okay?’ or ‘what’s wrong?’ — It’s okay. No room to question it. It was a simple and straightforward statement and I know she had no idea why I was crying all over her nice comfortable couch, but it still made me feel a lot better.

So I sat up, accepted the tissue she handed me, and told her about how my boyfriend dumped me because I couldn’t climax with him during sex.

Then she raised an eyebrow, smiled, and kissed me.

And my first thought was: wow, okay.

“I think,” I remember her saying, her lips curving and shiny from our kisses, “that sometimes people forget that there are no rules in sex. That there’s no ‘right way’ or ‘wrong way’ to have sex. That it doesn’t really matter what you do together, as long as you feel good.”

So she showed me. She showed me how to touch her in the way she liked, the way that got her to shiver under my fingertips. How she couldn’t help but arch her back when someone rubs circles around her areola, then gently scritches a fingernail on her nipple. She showed me how she likes to touch herself, how the lips of her pussy would get slick and wet when her clit is teased a certain way.

She showed me how to make her come with my mouth sucking on her breast and two fingers rubbing inside her.

Afterwards I sat back on her bed and watched as she laughed and stretched, sinuous and naked on her sheets — and realized I still had all my clothes on.

Feeling embarrassed for some reason, I started to take off my dress but then she raised a foot and put it against my shoulder and told me I don’t have to take anything off if I didn’t feel like it, that we had all night, and asked me:

“What do you want to do next?”

It felt like she was telling me to take the lead — an order that wasn’t an order — and it flipped a switch in my head and suddenly I wanted.

I wanted to make her come again, I wanted to see her shiver and shudder and cry out, I wanted to take her apart — to make her feel so good she goes crazy from it.

So I told her, and she kissed me, rubbing her body against mine, and showed me her toy box.

It turns out that taking the lead gets me out of my own head so that I stop obsessing about if I’m doing something wrong, and wondering why I’m not getting into it, why I’m not more turned on even though I really want to be. Focusing on making someone else feel good somehow makes it much easier for me to feel good.

I lost track of time as I played with Diana’s body, but kept count of how many times I made her come.

Once from a vibe on her clit while I fingered her.

Another on her hands and knees with her ass up in the air, working a dildo in and out of her pussy while rubbed her hole with my lubed up thumb. She whined high in her throat when she came that time, her thighs trembling with it, her hands fisted into her sheets.

Then I put her on my lap, her legs spread on either side of mine, and kissed and kissed her and kissed her while I told her — in a sultry voice that I didn’t know I could make — to keep that vibe on her clit, to make herself come with it — doesn’t it feel good, Diana? You’re such a good girl.

She choked on a sob when she came, her arms and legs wrapping tight around me as her whole body tensed for a long, suspended moment. And it was only after she collapsed against me and I fell back onto the bed, my head almost hanging off the edge, that I checked in with my own body and realized —

I was so fucking turned on.

I could feel how wet I was, how soaked my own panties were under my rucked up dress. I could feel — god — how much I wanted something inside my pussy, how much I was ready to be fucked.

So I told her to take that dildo I saw in her box of toys and fuck me with it.

I took off my panties and spread my legs, fingering myself, showing off for her while she put the condom on the dildo and smiled at me with bright, heavy lidded eyes. I told her exactly how I wanted it, how I wanted her to put it in me slow — no, slower — I wanted to feel every inch my pussy opened up for her.

I told her how to fuck me, and she obeyed beautifully.

And it had been that look on her face as she followed my instructions exactly, along with the satisfyingly full feeling of that dildo going in and out of my pussy that finally, finally pushed me over the edge, white starbursts going off behind my eyes as my my body arched from toe-curling pleasure of it.

So I was twenty-seven the first time I had sex with a girl, the first time I was able to come with another person, and also when I discovered that hey, I’m kind of a natural at this ‘telling people what to do during sex’ thing.