Enjoying Jess's First Time

I was 21 when I introduced my sister's best friend Jess to girl-girl sex. She and my sister Rachel were friends since first grade and they shared the same birthday. It was hard to believe they had just turned 18 and were finishing high school in two months. I still thought of them as dorky little kids who always bothered me growing up.

I was home from college for Spring Break, and I planned to hit a few clubs and stay at a girlfriend's place. But my friend began to run a fever, so I headed home a little after midnight. When I got to my bedroom, Jess was sleeping in my bed, because I was supposed to be out. I figured I would change and sleep on the downstairs couch, so I tiptoed in to the dimly-lit room, undressed, and opened a drawer to get a sleeping tee.

I was distracted by the thought that I needed to masturbate before I would ever be able to sleep. So, I crept toward the bed to get my vibrator out of the nightstand. Having had a few drinks, I wasn't as quiet as I thought, so Jess stirred and then opened her eyes. I stepped back from the bed and, for a few seconds, I stood there naked as Jess looked at me.

"'Whose been sleeping in my bed?' said the Mama Bear," I joked.

Jess raised up on her elbow and said, "Hi, Lindsey. Rachel said you weren't coming home. I'm so sorry. I'll go sleep on the couch." She was more cute than beautiful, but she had a nice, athletic body and pretty eyes.

"No need Jess, you were here first," I said. "I'll go downstairs."

"No, please, you don't have to," Jess said, still staring at me standing naked in front of her. The alcohol had loosened me up just enough that I felt excited, and not at all uncomfortable, as Jess gazed at my naked body.

"Well, it is a double bed, so I guess there's room for both of us if that's okay," I said, obviously buoyed by liquid courage.

"Oh...geez...yes, that's perfectly fine," Jess responded, more than a little nervously.

I pulled on an oversized tee and climbed into the bed over Jess and laid closest to the wall, with Jess's back to me. "You're sweet Jess. That couch is awful place to sleep," I said as I caressed her back affectionately. She giggled and wiggled her body a little closer to me, and I sensed she was more awake than asleep.

I was feeling frisky, so I continued to rub her back through her tee and asked if she and my sister had boyfriends. She said my sister had a few, but that Jess never did. In fact, she said had only really kissed two boys, which fit in with my thinking she and my sister were a little dorky. Jess was curious about my sexual experience and said she had always looked up to me, so the conversation got a little more intimate. After I shared a few stories, Jess snuggled closer so that I was spooning her.

Although I knew the answer, I asked Jess if she had ever kissed a girl. She said she hadn't, but she shared an experience when a girlfriend masturbated in bed next to her during a sleepover. I was turned on by that thought and I could hear Jess' excitement as she remembered the scene. When she asked if I had kissed any girls, I paused a few seconds before saying I had and that I actually found girls more interesting sexually than boys.

Jess was hanging on my every word as my hands moved over her ribs, waist, and hips as well as her back. I asked if she and my sister ever talked about being with each other. She paused before saying they hadn't, but she admitted that she found Rachel attractive. "Not as attractive as you, of course" Jess said as she nestled her back and rear even closer.

I reached my arm around Jess and whispered, "Such a sweet Baby Bear." I leaned in and kissed the back of her head and she adjusted her body so that my hand was resting on her flat tummy. Right then, I decided that I was going to make love to Jess.

I draped a leg over her and my hand moved up to feel her breasts. Jess gasped, but she offered no resistance. In fact, she turned her body a little toward me, allowing me to kiss her. Our tongues pressed into each other's mouths and my hand explored Jess's athletic young body. I sensed that she was nervous, but also excited.

My hand slid under Jess's tee to play with her boobs and nipples as we kissed. I wanted her body, so I quickly lifted her shirt up and off, and quickly slid down to kiss and suck her tits and to suck on her perky stiff nipples. Jess moaned softly as I slowly kissed my way down her tummy toward my prize, and I could feel that she was anxious about what was going to happen. I slid further down and began to kiss Jess through her panties. She immediately reacted, lifting her ass off the bed, pressing into my face.

I pushed her legs apart and licked her inner thighs. Jess was not shaved, and she had a nice blonde bush, which was exciting. My hand felt her through her panties, playing with her muff. I shoved my tongue hard between her lips pushing her panties inside her over my tongue. The combination of the thin material, her silky hair, and the musky scent were intoxicating. I pulled her panty to the side so my tongue could slide between her young pussy lips, and I tasted Jess for the first time. I heard her whimper and felt her hands on my head. I let the panties slide back and my mouth opened to take in her entire panty-covered vagina, which I sucked and gnawed on for a few minutes, until I needed more.

I grabbed Jess's panties and pulled them down and off. Before going back down on her, I looked up and saw her adoring look in the dim light. Her face told me she wanted this more than anything in the world. I did too. I maintained eye contact with her as I gently pushed her legs further apart.

My mouth clamped on Jess again and my tongue lashed at her bare pink folds, probing her virginal pussy. The familiar mix of sweet and tart raced across my tongue, and Jess instinctively spread her legs a little wider. When I turned my attention to her clit, Jess shrieked, before she muffled the noise with a pillow. Her hips began to rock, thrusting into my face as my finger teased her young pussy and my tongue sucked on her clit. It was only two or maybe three minutes before Jess started to moan and her breathing got heavy. I pressed just a fingertip inside her and she exploded, again using the pillow to muffle her screams.

I left my face pressed into Jess's pulsing pussy as she came down from her sexual high. I gently kissed her lips, my tongue feeling her soft pubes that also tickled by face. I had a thought to start licking her again, but the buzzing between my legs made me urgent to see if Jess was willing to reciprocate. So, I slid back up, wrapped Jess in my arms, and began kissing my sweet, new lover. Jess eagerly tasted herself on my lips and face, and I knew she was more than ready to taste her first girl. But that is another story...