Lesbionic escapades: A successful disaster

I’m more lesbian than bisexual, so I certainly was not looking for a serious relationship right away. And the “benefits” part only would happen once a month. Our escapades had their own little calendar, actually — each month, one time between the 24th and 27th. I don’t know what it is about these dates, but whether it was the lunar cycle, Emily’s menstrual cycle, or her hetero-to-homo ratio, something kicked in between those dates. Something kicked in, and she wanted me. For one night.

In between those magical dates, we’d fall back into being just good friends. In fact, she’d become one of my best friends. And there was no weirdness or awkwardness during those non-benefits times. Occasionally some confusion, but generally we both understood and appreciated our arrangement. And life was good, living one adventure to another.

As far as the rest of the world was concerned, we could have been sleeping together every week — or every night, for that matter. Hell — one of her friends thought we had moved in together. (It’s amazing what a million Facebook pictures of the two of us together gets people thinking. But in reality, we’re both just “narcissistic photo whores,” as we lovingly call ourselves.) The reality was quite different. We were not exclusive — I knew this going in. There was no “relationship.” We were occasional lovers. And in fact, even when we did sleep together, we didn’t do all that much. It can be hard for even Emily to give herself an orgasm, and she is surprisingly shy with women. Add to that my strict sexual safety rules, and even after four or five months, our “benefits” were surprisingly tame.

My body is much kinder to me than Emily’s is to her, so in some of our prior escapades, I had gone home fully satisfied. Except that I wanted to do the same for her. And then some. She still hadn’t let me go all the way — lesbian style — with her yet. Partly, that was due to her shyness with women. Partly, she was trying to protect me. After all, she wasn’t exclusive, and she respects my concern for safety. However. Being the paranoid, responsible lesbian that I am, I always carry protection with me. Just in case.

I didn’t even expect anything to happen that particular month. Sure, the plan was to sleep over one night on the last day of that magical window, but we often slept together when only sleep ever transpired. But as dawn seeped through her bedroom blinds on the 27th, she welcomed my trailing fingertips. Silky, feminine skin beneath my hand. Curves and edges of clothing. Slowly, with every ounce of bravery, (it’s so hard to tell sometimes when she wants me and when she wants to be just friends,) my fingertips inched slowly to her most exciting curves and shapes. My lips tasted her neck. Her shoulders. Finally, her lips.

She paused.

“So, two things,” she said. “One, I’m waiting for my roommate to leave. And two, then I’m going to take a shower.”

My turn to pause.

“Aaaaand then?” I asked.

“And then you can blindfold me and do whatever you want,” she said. “So I guess that’s three things.”

Anything, anything?” I asked, surprised and excited.

Finally the door shut. She hopped in the shower while I dug in my purse for one of the infamous dental dams that I’d been carrying around with me in my purse for months. The first one I pulled out is purple. Of course it is, I thought. My gay color.

If you’ve never used a dental dam, it’s an interesting adventure in and of itself. It’s a decent size of thin latex that you can use like a condom for female oral sex. It’s a great tool, but I think there’s probably a learning curve. They are a bit awkward to use, as you have to hold them in place, and of course it’s a lot harder to figure out your road map without any visual and with hindered physical sensation. I think these devices probably work best for mutants with a third hand. Furthermore, if you suck at all, it’s like blowing an inverted bubble inside your mouth. A sexy choking hazard. And I’m pretty sure it made me drool a bit. And not in a metaphorical way. Furthermore, being a newbie still to female sex has got to help the skill level exponentially. Er, or not. But it was nonetheless thoroughly exciting and satisfying to finally — for the first time in over a year — be actually doing this most coveted sexual act on a female lover.

Somehow, between that and a vibrator and kissing and patience, it fi- fi- fi- fi- finally…

[image-1]“Put your hand right here and don’t move,” she said as she pressed my hand onto the lower left part of her abdomen. I was still grinning from my accomplishment. I figured she was hyper sensitive post orgasm like I can be sometimes. We lay there in silence for a good while.

“Oh my god, I thought I was going to have to get up and run out of the room screaming,” Emily said. I giggle. “So, sometimes after an orgasm, my body hates me and goes into excruciating pain and I want to die.


“It happens to me sometimes, too, and there’s no particular reason for why it happens, so it’s no one’s fault. But damn.”

Needless to say, I did not get my turn that month. But I was okay with that, for many reasons.

Later that afternoon, her wet dog was sitting in my lap in her car as we drove back from the dog beach. Suddenly, I burst out laughing. I turned to Emily with a lopsided grin.

“So there’s this hot girl,” I began. “We’ve flirted for almost a year now. And then we became friends with benefits about four or five months ago, depending on when you start counting. And now she’s like my best friend. Finally lets me go down on her, after all of that, and she finally has her first orgasm with me. Which immediately causes her excruciating pain. Yeah. That was pretty awesome.”

“Well, at least this would make a great blog post,” Emily said when she finished laughing.

“Um, yeah,” I said. “We’re going to have to try that again sometime. …Wait, really? You’re okay if I write about this?”

We tried to figure out how in the world I could illustrate the post with images. Soon we were lying mostly naked on her bed, objects pressed up against her door so her roommate didn’t accidentally walk in on us. I held my hand strategically over her abdomen like I had earlier to help the pain, only this time I was also trying to ensure I covered up important bits to keep the image appropriate. She held her camera above our bodies and tried to snap the perfect blind self portrait through our laughter. My iPhone rang near our heads. It was the woman I soon would  try to avoid, asking me to go out on a date later that afternoon.

Well, at least this will make a funny story.

It’s probably not a good thing when after sleeping with a woman, she says, “You know, this would make a great blog post.” Such is my life with women. But at least we were laughing by that point.

“Emily” and I had been flirting for almost a year. We’d been friends with benefits for four or five months, depending on when you started counting. But I have this awesome tendency of choosing the unavailable, screwed up, bisexual-but-male-leaning women.

But they’re so pretty.

And smart and funny and geeky and awesome. But never the easy ones. This time, that didn’t seem to matter. In fact, it worked out quite well most of the time. I hadn’t even filed for divorce yet after deciding that

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