In high school I was nothing special, I was a pretty average guy all around. I was 5'9”, average build, I had a 78 average, and I wasn't really great at sports. I wasn't bad looking, I just had a bit of trouble talking to girls, but that wasn't really a problem, as I generally tried to focus on my studies, not dream about hot girls.
However, there was one girl I could not stop thinking about. Her name was Jenny, and she wasn't only great looking, she was one of the friendliest girls in school, and wasn't against talking to anyone. She was around 5'4”, had red hair which reached her shoulder blades, and her emerald eyes would stand out on any occasion. Her breasts were around a C-cup, and she had a nice round ass.
I had spoken to her on a few different occasions, mostly because I sit near her in Math class, and we usually wind up being the odd ones out of our groups when we have partner projects. One day, however, the situation was a bit different. It was nearing Christmas, and our math teacher was looking for volunteers to help out with Caring for Christmas. It was a fundraiser in which we would collect toys, and bring them to less fortunate families and orphanages on Christmas Eve. Jenny raised her hand, so of course, I raised mine as well.
Every day leading up to Christmas, the few of us that volunteered would set up tables in grocery stores or at the mall, collecting toys and donations, and we would encourage other students to help out. By the end we had around twenty garbage bags full of toys. On Christmas Eve, Jenny and our math teacher were chosen as the drivers, as Jenny had a panel van her father let her borrow, and our teacher had a Ford Ranger. We had groups of three, our teacher, my friend Nick, and some random freshman were in one group, and Jenny, her friend Crystal, and I were in the other.
Throughout the night we drove from place to place, delivering toys, with Jenny and Crystal talking in the front, and me organizing the toys in the back. They were mainly talking to each other, but they would often turn around to ask me some normal questions like how much we had left, and where we were going next. One thing I noticed was how often Crystal would look back and giggle, it made me very uneasy and paranoid.
Finally, we made our last delivery just before midnight, and we dropped the signed delivery sheet through the mailbox of the school. Crystal lived closest to the school, so, naturally, we dropped her off first, and as she stepped out of the car, she said, “You two have fun now,” and let out a loud giggle.
As I hopped in the front seat I looked at Jenny and asked, “What was that about?”
“ I'm not sure,” she said, as a big smirk spread across her face.
We made small talk on the way to my house, and nothing really seemed off. That is until, a block before my house, she hauled into the parking lot of a shut down video store and turned off the van. Then she looked at me and started talking a mile a minute.
“I've really liked you since we first talked to each other at the beginning of September. I've been trying to find the right moment to admit it, but I keep backing out because I'm afraid you won't feel the same way. I don't know why I'm doing this right now, but I really hope I'm not making a giant idiot of myself. If you don't feel the same way I'm cool with that, and I won't bring this up again, and we can pretend this never happened. I'm sorry.”
As I looked into her eyes I could not believe what was happening, but somewhere deep within me I found the courage to say just the right thing.
“ Don't be sorry, I feel the exact same way, and I've had the exact same problem. But it's all out in the open now and-”
Before I could say another word, she had her lips locked around mine, and her tongue was dancing around inside my mouth. She then reached down and began to haul my t-shirt off,and we had to separate in order for her to haul it over my head. But when my shirt hit the dashboard she stopped.
“I'm so sorry. I didn't mean to-”
It was my turn to cut in. Our lips were back together and she did not resist. We kept kissing for another few moments, our tongues wrestling back and forth, and then she started undoing her blouse.
The first time I had ever kissed a girl, and it was already going this far. I knew I should take the chance, but I couldn't without knowing she was completely sure. I pulled myself away from her as she undid the last button. Underneath her blouse she had a green bra on, the same colour as her eyes. They accentuated each other perfectly, and contrasted her red hair in just the right way. I wanted to keep going but I had to ask.
“Are you sure you want to do this so quickly?”
“Of course, but I'm still a virgin, so take it easy on me.”
She seemed to think I was more experienced than her. “ This is way farther than I've ever been before so don't worry. It's comforting to know we're both on the same playing field.”
She smiled and let out a sigh of relief before saying, “speaking of comfort, sitting up in these chairs isn't.” She then reached under the seat and hauled out a thick blanket, spreading it across the empty space in the back of the van. Dropping her blouse on the floor, she lay down on the blanket, waiting for me to join her.
As I started to move, she instructed me to take off my jeans. I obeyed, and lay down next to her in nothing but my boxers. I rolled over on top of her and we started making out, but I quickly moved from her mouth, and down her neck, fumbling with the back of her bra.
As soon as I got the clamp undone, I quickly moved out to get the bra off. I stopped for a moment to take in the sight. Her breasts were a perfect C-cup,perky, and she had small areolas, and her nipples were rock hard, waiting to be sucked and fondled.
I moved in. Taking her left tit into my mouth, and gently twisting her right one between my fingers, she let out her first loud moan. As she was clearly enjoying it, I began lightly biting her tit. For the next few moment I kept it up, stopping only to switch sides.
Soon I felt her bend her legs, so I stopped for a moment, to realize she was taking off her own jeans. When she had them flicked off to the side, and she had on panties matching her bra. I tried to continue, but she caught me off guard, rolling over on top of me and, starting from my lips, she started to kiss her way towards my throbbing dick.
As she got closer to my cock, she started hauling down my boxers. Hauling away for a quick second, she threw them away and quickly started sucking my cock. Even though it was my first time, I could tell it was hers too, as she had some trouble at first. But soon, all I could think of was her lips and tongue massaging my cock, as she looked up at me with her beautiful green eyes.
I did not last long, and I soon came harder than I ever had before. She managed to keep it all in and swallowed, giving me one last lick to make sure she didn't miss anything.
I was over the moon, but I still needed time to recover. I jumped up and pushed her down, I was in control again. I didn't waste anytime hauling off her panties, the only clothing she had left on. She had a short, red bush, over thick, juicy pussy lips. She was neatly shaved, she had obviously been planning beforehand.
I began kissing her thighs, teasing her pussy to buy that little bit of extra time. But I couldn't wait any longer. Between the sweet, musky scent of her dripping wet pussy, to my own excitement and eagerness to keep going I had to dive in.
The moment my tongue entered her, she let out a loud sigh. I started making my tongue dance around inside her pussy, wanting to lap up every last bit of her juices, as they tasted every bit as good as they smelled, and then some. I kept it up for another few minutes, with her doing nothing but moaning and shivering with ecstasy.
Eventually she couldn't take it anymore and screamed at the top of her lungs, “I need you to fuck my pussy now!”
At this I jumped up and swung her left leg over my right shoulder, so I could easily access her pussy. I started slow at first, as her pussy was very tight, I pumped in and out gently, entering further each time, until I hit something solid. I looked at her, and she just nodded her head. I pull back, and thrust forward as hard as I could, busting right through her hymen, and burying myself balls deep in her pussy.
“Fuuuuuuuuuuck!” She let out a loud scream. I nearly pulled out, but she started pivoting on my dick, so I started pumping as fast and as hard as I could. I could feel myself getting close, I knew it wouldn't last long.
As though on queue, she screamed, “I'm about to come!”
I pumped harder and harder, and watched as she arched her back. She started spasming as her pussy contracted around my dick. I couldn't take it anymore and I buried my dick to the hilt, as I came straight into her womb.
We both collapsed together and stayed that way for what seemed like hours. When we finally brought ourselves to get dressed, we saw that was 1:30. She quickly rushed me down the block to my house and raced home herself. I had no trouble getting to sleep that Christmas Eve.