I had always been shy and nervous around her, but I knew I had to confess my feelings. She was, after all, the hottest person I had ever seen, and I was desperate to be with her. When I finally worked up the courage to tell her, she invited me to her house for a "study session." I knew what she was doing; she was teasing me, and I was nervous as hell.

As soon as I walked through the door, she could sense my nervousness. She smiled wickedly and said, "Come here and give me a hug." I hesitantly approached her and gave her a light, awkward hug. She pushed me away gently and said, "That's not good enough. You have to wrap your arms around me and press up against me really hard for at least a minute." I caved in and did as she commanded, my heart pounding in my chest. As I hugged her tightly, I could feel her body against mine, her ribs pressing into my chest, her nipples hard against me. I became uncontrollably horny, my penis starting to get erect. She noticed immediately and said, "You're not allowed to let go of me." I could feel her breathing heavily, her heart pounding against my chest. She asked me when the last time I had masturbated was, and I stammered out an answer. She then asked me how many times I had jerked off to her in my lifetime. My heart was pounding like crazy from the nervousness, but I eventually admitted that it was probably around ten times.

She let go of me and said, "I have a challenge for you." She went into her drawers and pulled out a vibrator. "If you can orgasm ten times within the next two hours, I’ll fuck you whenever you want for the rest of the year. I know as a male it would be hard to do it, so for the next two hours, I’ll let you do whatever you want with me. You can make out, touch me, hug me, hump me, kiss me, while you vibrate yourself." I told her I’d try my best.

I asked her to hug me tightly and tongue kiss me. She complied, and we started making out passionately. Her lips were soft and inviting, her tongue dancing with mine. I could feel her body pressing against me, her breasts crushed against my chest. I wrapped my arms around her tightly, pulling her into me as we kissed deeply. I started to grind against her, feeling her body respond to mine. I was so turned on that I knew I wouldn't last long.

I reached down and turned on the vibrator, placing it against my shaft. The sensations were intense, and I knew I was close. She whispered in my ear, "Come for me," and that was all it took. I exploded in ecstasy, my body shaking with the force of my orgasm, our hug never breaking.

But she wasn't done with me yet. She pushed me back onto the bed and straddled me, grinding her hips against mine. "Again," she commanded, and I complied, my body already craving more. I turned the vibrator back on and started to stroke myself, the sensations even more intense this time. She leaned down and kissed me deeply, her tongue exploring my mouth as I came again, my body convulsing with pleasure, our tongues still dancing together.

We continued like this, her teasing and commanding me, pushing me to the brink and back. Each time, she would hug me tightly, our bodies pressed together so firmly that I could feel her heart pounding against my chest. I could feel her ribs, her tummy, her hips, all pressing into me as we hugged and kissed and ground against each other. I lost count of how many times I came, but I knew I was getting tired. My body was exhausted, and I could feel myself slowing down. She noticed and said, "You're running out of time. You need to keep going."

I tried to focus, to push through the fatigue, but it was no use. I was spent, my body unable to respond anymore. I looked up at her, my eyes pleading. "I can't," I admitted, my voice hoarse from exertion. "I'm sorry, I can't do it anymore."

She smiled softly and kissed me gently, wrapping her arms around me tightly. She started to grind her entire torso against mine, our bodies pressed tightly together, our arms wrapped around each other. She kissed me deeply, our tongues dancing together as she moved against me. I could feel her nipples hard against my chest, her hips grinding into mine. I was so turned on that I could feel myself getting hard again. She whispered in my ear, "Come for me one more time," and I complied, my body responding to hers as I came one last time, our hug never breaking, our tongues still exploring each other's mouths.

She let me rest for a moment, then said, "But our time isn't up yet. Let's see how many more you can get before the two hours are over."

I nodded, determined to make the most of the remaining time. I pulled her close, kissing her deeply as I turned the vibrator back on. But it was no use; my body was too exhausted to respond. I kissed her neck, her shoulders, her breasts, trying to stir myself back to life. She moaned and arched against me, but I could feel myself fading.

I looked up at her, my eyes filled with desperation. "I can't do it," I said again, my voice barely a whisper. "I'm sorry, I can't orgasm anymore."

She smiled and stroked my hair gently, pulling me into a tight hug. "It's okay," she said. "You did your best. I'm still going to let you come over and fuck me once in a while. You deserve it."

And so, even though I had lost the challenge, I still felt like a winner. I had experienced something incredible, something I would never forget. And I knew that, despite the challenge, she still wanted me.

I still think about her to this day, and the memory of that afternoon will forever be etched in my mind, our hugs and kisses and the intense physical contact that left me craving more.