An Incredible, Amazing Really True story

Isabelle Gray

It's a great story, really, the one about the first time I had sex with a woman. It's the kind of story that's almost too good to be true, and over the years it has acquired its own mythology among my friends and me. It could also be called the story of how I accidentally became a lesbian. I was nineteen, going on thirty, in my own mind at any rate. I was on sabbatical from college after two years spent doing most anything but attending classes and acting collegial. I was in the midst of a Western adventure from San Francisco to Phoenix, the likes of which I blush to recall. Eleven years removeo; from My First Time, I realize that my personal history is quaint and charming only to myself, but I still hold the memories fondly.

The story begins with a party—the kind where a bunch of kinky people get together with their favorite toys and use them on one another into the wee hours of the night. I had recently been introduced to the group, and it was made quite clear that I was the Flavor of the Month and a good decade younger than most of the other partygoers. I had no problem with that. It was nice to be the center of attention. I acted as worldly as possible, while biting my tongue and hoping that no one discovered that I had no idea what I was doing there. Don't get me wrong—I knew how to use my toys, but I had no clue how to get physically intimate with another woman. In fact, up until that point, I had never even considered being with a woman. It wasn't something I opposed. It was simply an option that had not theretofore been available to me until now. In the early hours of the party, I did my stroll through the three rooms where the party was taking place. I flogged an acquaintance I had met at a potluck a few weeks earlier. I let a boi shine my boots with his tongue. I was seeing and being seen.

The peacocking was an act. I was painfully shy and found it far easier to get to know people with the kiss of a whip or the tease of a paddle than to attempt a conversation. If any of the women at the party had known me well, they would have realized that there was a fraud in their midst. Throughout the night I had my eye on one woman, Billy, a round, gorgeous lesbian in her forties with long black hair and green eyes. She wore jeans and a corset that barely covered her breasts, and her fingers were covered with intricate silver jewelry. We made eye contact several times throughout the evening. I would catch her, now and again, staring at me, and I pretended that I didn't notice. Slowly but surely, I drifted closer and closer to her, until I was sitting behind her, chatting with her as I dragged my fingers back and forth across the exposed expanse of her upper back. The light scratching evolved into massage, and soon Billy was moaning and leaning further and further into my body.

I can admit that I had no idea what I was doing. I wasn't quite sure how to proceed. While I'd had plenty of experience with men, making love to a woman was uncharted territory. The fact that we were surrounded by other women who were taking an increasing interest in what we were doing didn't help matters. Exhibition had never been my forte. After twenty minutes or so of manually manipulating Billy's upper back, she turned, grabbed my chin between her fingers, and pressed her lips against mine, her tongue darting between my lips as I gasped, then kissed her back. My lips were tingling. My fingertips were tingling. My cunt was throbbing. I placed one hand at the base of Billy's neck, and slowly slid it until my fingers were tucked between her breasts.

Carefully, I began to unfasten the corset until it fell back revealing the most beautiful pair of breasts I had ever seen—full, heavy in my hands, with erect, dark brown nipples surrounded by a few freckles. I brushed my lips across the upper curves of Billy's breasts and she smiled down at me, sliding her hand around to clasp the back of my neck. One by one I pulled her nipples into my mouth, enjoying the way they felt against my tongue and how they swelled as I began flicking the tip of my tongue over them. The room had gotten quiet as the people around us began to close in, forming a tighter circle around us.

"Do y'all have any preferences for music?" one of the women asked. Billy and I shook our heads, and soon the twang of Willie Nelson filled the air.

I could have lavished my attention on Billy's breasts for an indefinite amount of time, but her body was insistent, and her hand on the back of my neck urged me lower. I kissed my way down her belly, around her navel, to her waist. Slipping my hands beneath the waistband of her jeans, I quickly had them unbuttoned and Billy did her part by wriggling away from them. She wasn't wearing any underwear, and the first thing I saw was the dark, silky hair covering her mound. My lips moved lower, over the soft, sweet hair and down to her pussy lips. Billy sighed and lay back, pulling her knees up and apart. In the dim light of the room, I could see that she was already wet, though beyond that I was somewhat unclear about what I was looking at. Praying that no one would discover that this was all foreign territory, I pulled her pussy lips apart with my fingers and dragged my tongue along the length of her moist slit. The taste was tangy at first, and then, as I slid my tongue inside her cunt, I found the unexpected flavor of strawberries.

A Johnny Cash album started playing. Billy's thigh muscles tensed and she placed both of her hands atop my head, curling my hair between her fingers, tugging slightly as I slid my tongue lower still, then back toward her clit. When my tongue finally reached her clit and I began to lick in slow, steady circles, Billy hissed and whispered, "Yes, that's it, right there." I smiled into her pussy, determined to do whatever it took to keep Billy, and her pussy, as happy as I could. I slid one hand up Billy's body, enjoying the sensation of our skin coming together until I reached her breasts. As I teased her clit with my tongue, I rolled her nipples between my fingers until Billy gasped and sat up. "You're driving me crazy," she said. My heart fell but I wasn't going to let my disappointment in myself show.

"Is that a good thing?" I asked.

"Without a doubt," Billy answered.

My confidence renewed, I slid my tongue back to her cunt and began thrusting it in and out, slowly at first, but then faster and then slower again enjoying how Billy's body responded. Past the crowd watching us, I could hear the stereo switching to a new album—Tina Turner. I propped myself up on my elbows, trying to push myself deeper into Billy, rocking my hips against the floor. I couldn't believe how turned on I was. Billy's pussy became wetter. Her fingers gripped my hair tighter. I was getting the hang of this, I told myself. I shifted slightly so I'd have a bit more room and began teasing the edges of Billy's cunt with two fingers while my tongue flicked around the edges of Billy's clit, darting away each time Billy tried to adjust her hips to put her clit on my tongue. I was being a tease and I knew it. I slid two fingers inside Billy's cunt and shivered as I felt the warm, slick tight flesh gripping me. The deeper I slid my fingers, the wider Billy's legs spread. Once I was as deep as I could go, I flipped my wrist and began pressing my fingers upward against something soft and spongy. "Fuck me, hard," Billy muttered through clenched teeth. I wrapped my lips around her clit, sucking insistently, while I thrust my fingers in and out of her pussy to the rhythm of "Private Dancer."

Then, Billy decided it was time to take charge. She pushed me away and said, "I want you on your back." I quickly complied and Billy straddled me, facing my feet. She inched backward until her pussy was pressed against my mouth. My jaw was beginning to ache, but I opened my mouth wider, and resumed with licking and sucking and sliding my tongue over every inch of her pussy. Billy began to rock, her body pressing into mine. The tender wail of Miles Davis filtered through the other sounds around us. Then she began to thrust, and her thighs started to shake. I grabbed hold of her ass, slapping the firm cheeks. A gush of wetness hit the back of my throat. "I'm going to come," Billy shouted. I stopped. She grabbed hold of my ankle. "Don't fucking stop, kid." I resumed my efforts, struggling for air. Billy began to grunt in loud, guttural tones as if she was releasing something deep and dark. I was certain of the moment she came—the very crescendo of her climax, when her cunt juice was thick and smeared across my face and her body shuddered above and around me.

Afterward, Billy rolled off and we lay there, side by side, facing opposite directions. I reached for her hand and entwined my fingers with hers. As sweat began to slide down my face and my neck I realized that I was exhausted. And suddenly I heard a smattering of applause that got louder and louder. When I opened my eyes and looked up, the entire party was standing over us with a range of expressions on their faces.

The woman who had started the music shook her head and said, "You guys went through four albums—that's more than three hours of pussy eating." I didn't quite understand the relevance, having no point of reference. Billy sat up, wrapping her arm around my shoulders. She kissed my forehead and said, "Either you're a sadist or you really enjoy eating pussy."

I smiled with what I hoped was a coy expression on my face. "Both," I answered.