Pining for Madison

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I kissed them, I licked them. My tongue circled her nipples, which had now become erect. I flicked at them with my tongue. Madison, groaned in delight.

Things were certainly getting hot and heavy. Madison pulled my head back from her chest.

"Are you ready?" She said nodding her head towards the middle of the bed.

"Yes, are you?" I asked, making sure she was comfortable with what we were about to do.

She nodded her head and when she climbed off my lap, she paused for a moment.

"Oh, did you finish already?" She said looking down at the large wet spot on the front of my underwear.

I looked down.

"Oh!" I said, pulling the waistband from my body and looking to see what happened. I was still rock hard, much to my relief.

"No, that's just precum I think. I'm still good."

"Phew! Have you got the um..." Madison asked.

A look of panic covered my face.

"What? What is it? Did you remember to bring it?"

"I... I don't know."

I quickly bolted up and grabbed my bag. I open the zip as far as I could and frantically emptied the contents on to the floor.

"Please be in here, please be in here," I cried out, dropping to my knees.

I started fanning out the books in a mad rush. Praying that my erection would hold. That's when I saw it, lodged between two pages in one of my notebooks. The small foil packet handed out by Mrs Wrentmore in Biology.

"Oh thank god!"

I got up from the floor, leaving the mess I had made and hastily pulled down my underwear, almost falling over in the process and joined Madison on the bed. The jostling made my dick wag side to side like an excited dog.

She tilted her hips upwards and began taking her thong off. She got them down as far as her knees, before I took over and removed them completely, casting them behind me.

I knelt there on the bed. Before me was the now fully naked Madison, the first girl I had ever seen naked. Her whole body was sublime.

She parted her legs, inviting me closer. I shuffled closer to her. My dick painfully hard, straining from my body as if desperately trying to reach her. I tore open the condom packet with my teeth, then removing it.

The condom felt greasy in my hands as I carefully rolled it down the length of my shaft, pinching the tip afterwards.

We looked at each other one more time and I slowly lowered my body on top of hers. I kissed her, then tilted my hips forward to enter her.

"Um, that's my butt Ad," she said softly.

"Oops, sorry," I said apologising.

"I'm not quite ready for that just yet," she said jokingly pumping her eyebrows.

"Here, let me help."

I felt Madison's hand around my dick, as she lined it up against her entrance. She nodded her head, giving me the green light to try again.

My heart began pounding in my chest, this was it. I was going to lose my virginity to this amazing woman.

I pushed forward, our bodies making contact as my dick pushed inside her, parting her soft lips.

Madison gasped as she took me inside her. I felt some resistance and pushed harder to try and over come it. Madison's face winced.

"Are you okay? Should I stop?" I asked with concern.

"No, it's okay, just go slow if that's okay."

I kissed her forehead, and pushed again. I was about half way in, then the resistance gave way. Madison let out a cry. I continued to slide in and out of her slowly, while she grabbed my hips and controlled the rhythm of my thrusts.

I pushed again, this time making it all the way inside her. I could feel her hands tighten around me. The feeling, although slightly diminished by the condom, of being inside her was out of this world. Her body radiated a warmth and a softness that I craved.

Madison wrapped her legs around my lower body and pulled me in closer, pushing me deeper inside her. She moaned softly as I gently rocked my body against her. Her breathing, our breathing rate increased.

I could feel her sex tighten around me, her face looked like it was about to scream, but not a sound left her mouth. Her whole body tensed up, gripping me tighter and pushing me deeper. I couldn't hold it anymore, I let out an insuppressible groan as I came, my face frozen in a moment of pure bliss.

I held myself inside her, my body continuing to pulse, as if it were giving her everything I had, my body and soul.

When there was nothing left to give, I carefully pulled out, holding the condom in place. There was a reddish residue on the condom.

"I think you've been bleeding, are you okay?" I asked, carefully shuffling backwards.

Madison put a hand between her legs, then brought it back up to her face. There was a trace amount of blood on her fingertips.

"It's okay, I think this is meant to happen on the first time."

"Ah okay, for a moment there I thought I might have hurt you."

I grabbed a handful of tissues from her desk and passed them to her, then took another handful for myself. I carefully removed the condom and wrapped it in the tissues.

We took a moment to clean ourselves up, and returned to the bed, laying next to one another.

"Was it okay? Was... I okay?" Madison asked.

After everything Madison and I had done to get to this point, it seemed strange to hear her sound so vulnerable.

"It was amazing, you were amazing," I said gripping her hand and kissing the back of it. "Was it okay for you?" I then asked.

"Yeah, it hurt a bit at first, but after that it was intense, you know. The feeling of you inside of me... and when you came, I felt everything. It was so good."

The sex itself may have only lasted two minutes, but it was easily the best two minutes I had ever experienced. PERIOD.

We cuddled for a while, and could easily have gone a second time, had we had more condoms, but neither of us were willing to take the risk. So we just laid there, talking, joking, laughing, and discovering so much about each other.

After all these years, hoping for the day I get to be with her. It finally happened and in the most unexpected way. I can't wait to see what happens next.

As for the biology assignment, Madison opted against the inclusion of her pencil drawings. In hindsight it was pretty obvious who her muse was. She folded the paper and kept it in her diary as a reminder of our first experience together. When we handed in the completed assignment, we managed to get an A, no doubt thanks to our hands-on approach to this assignment.

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Secretauthor2021Secretauthor20212 months agoAuthor

The second story in the Pining for Madison series is out now. It’s called ‘Pining for Madison: The Favour’. Hope you enjoy it and thanks for reading.

AnonymousAnonymous2 months ago

Gym/health class helped me to find a regular sex partner when I was in highschool. I had sex before then but a girl who I had been friends with for ten years or so hadn't. She mentioned during sex ed part of class that it was a shame she hadn't been laid yet and I said well I can take care of that. I did for the next two years before I moved away. I'm not sure that anyone other than her little sister suspected anything. She did give me hell for not getting with her earlier since we were neighbors and had hung out a lot before then. Thanks for the story and the reminder of good times

Secretauthor2021Secretauthor20212 months agoAuthor

Fear not, Part 2 is nearly done and I’m also creating the plot outline for Part 3.

BottomdanBottomdan2 months ago

Really enjoyed reading that!! Wish there was a part 2

BufoAmericanusBufoAmericanus2 months ago

Excellent story that is well written and great character development. It also presented itself as very realistic.

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