Nigel:
I walked through the doors of McClintock High School, just coming back from summer break.
Oh, how I miss summer break. I had the most wonderful time with her back in the old tree house. Rachel's body is so elegant. The fullness of her breasts excited me, and the first time I penetrated her with my cock, it was so tight I could hardly contain myself with excitement.
As I was stuck in my memories, I tripped up the stairs and dropped all my books.
"Need a hand?" a voice asked, oh so ever sweetly.
"Oh, sure Rachel. Thanks." I was blushing from embarrassment, since I had an erection from the thought of our summer fun.
As we picked up my things, I couldn't help but stare at her breasts. She was wearing a turquoise v-neck shirt, exposing her cleavage. I started to get nervous and I couldn't focus.
"Nigel, are you listening?"
"What? Oh, I'm sorry. What did you say?"
"I was wondering if you wanted to hang out after school, at The Café?"
I was staring into her beautiful brown eyes. It seemed as though they were looking right through me, reading my thoughts.
"Of course I want to. I'll meet you at your locker after 7th hour, alright?"
"Okay, see you then!"
She gave me a kiss on the cheek and walked away. Her ass was so perfect: not too big; not too small. I would've smacked it right then and there if we weren't in the middle of the hallway.
As I walked to my first hour, I ran into Lizzie, my ex girlfriend. I can't believe I had dated her. I guess back then I was into the big ones, since Lizzie was so large. Despite the fact that she had lost the weight, she hadn't changed a bit. She was still as annoying as ever, except now she had acne and braces. She had bangs and wore her hair in pigtails, and had big, nerdy glasses. She wore an oversized yellow hoodie and blue skinny jeans with black and white Converse.
Although she was the one to break up with me, and at the time I was devastated, I couldn't help but be so happy that the relationship had ended.
"Hey, Nigie! I didn't expect to see you here!"
Trying to avoid her, I responded, "I don't see how it's such a surprise, it is school, you know."
"Oh yeah!" she snorted. "What class do you have now?"
"Biology."
"With Mr. Hogan? Me too! We can be science buddies, and sit next to each other, and walk to class together, and –"
I had walked away without her noticing and slipped into the men's room. I set my things down on the sink and stared into the mirror. I still had no hair, and still wore my black sunglasses. I wore a red short sleeve shirt, with black shorts. I guess my style hadn't changed much.
I took off my glasses and my eyes were heavy due to lack of sleep. I slashed some water onto my face and put my glasses back on, and walked out.
As the day went on, I ran into old friends I haven't talked to in a while. I said my hellos and kept going on with my day excited for it to be over. All I could think about was Rachel. I had wanted to ask her out for the longest time, but I didn't have the guts. I don't know why I couldn't ask; it was obvious she had wanted me.
After a long day of waiting, the last bell rang and I started my way to Rachel's locker. She was there waiting, with her beautiful figure, her shoulder-length blonde hair, and her outstanding looks. I walked up to her with a huge smile on my face.
"Hey, Rachel. Long time no see, haha. You ready for our date"
"Who said this was a date?" she said, which made me all choked up and embarrassed.
"I'm just messing with ya. Don't get all embarrassed," she said with a wink.
We walked to The Café, since my car was in the shop and she didn't have a car of her own. We both ordered strawberry lemonades, and took turns talking about our day.
"So," I had started to say. "do you want to come back to my place?"
"Sure, sounds like fun," she answered, with a smile that melted my heart.
"Alright, lets go."
We paid for our drinks and headed off. As we're walking to my house, which is only a couple blocks away, I started to contemplate asking her out in my mind. I wanted to so badly, but yet I was so afraid to. I had eventually decided I was going to ask her.
I unlocked the front door and opened it. All the lights were out and no one was home, so I turned on the light. Rachel shut the door behind her, and looked into my eyes. I walked up to her and put my hands on her waist, and she threw her arms around my neck. I gently kissed her, slowly slipping my tongue between her lips. I picked her up and she had her legs wrapped around me. Our making out had gotten intense, and things were staring to get hot and heavy. I put her down, grabbed her by the hand, and led her upstairs into my room.
"Sit down on the bed, beautiful. I have something to tell you."
I was nervous. I felt a bead of sweat trickle down my forehead.
"What is it, Nigel?" she said, with her sweet, tempting voice.
"You know I have strong feelings for you, and you for me. My feelings are really strong, though. I care about you a lot, and I want you to be my girlfriend, so will you?"
She smiled her ever so sweet smile and kissed me.
"I can't tell you how long I've been waiting for you to ask that. Of course I will."
"Good," I said. "now let's get back to where we left off."
She giggled, and I kissed her, hard. She took off my shirt, and my hands had found their way up her bra, and soon enough I had unsnapped it and it was off. I lifted her shirt over her head, still kissing her. My kisses gently started making their way to her neck, then her chest. She was enjoying this a lot, and I loved making her happy, so I started unbuttoning her shorts.
"Nigel," she said, "we can't. I don't think we have a condom."
"SHIT!" I had yelled in frustration. "We can still do other things though, can't we?"
"Of course," she said
I then continued to kiss her breasts. I slipped off her shorts and started kissing her moist pussy through her bright blue panties. She had then started breathing heavily, so I took off her panties and slipped my index finger into her pussy, moving it in and out. She had started biting her lower lip, and I knew she was enjoying it. I had put another finger in, and started licking her clit, too. She had started moaning, getting louder with every lick. I put in a third finger and started fingering her faster and harder, while my licking and sucking got faster, too. She couldn't contain herself. She was practically screaming with moans, involuntarily lifting herself due to pleasure. She had a tight grip on my pillow with her right hand, and her left hand on my head. In no time, she had her orgasm. She leaned forward, grabbed my face and kissed me.
"Do you think it would be fun to try anal? I mean, we don't need a condom for that, do we?"
Her question caught me off guard, but I'll try anything once.
"Yeah, I think it'd be fun. Let's do it."
I grab a jar of Vaseline, and gently rub it around her asshole and on my dick. I slowly put the head of my dick in her ass, which makes her yell.
"I'm sorry babe, am I hurting you?"
"No, I'll be okay, just get it in there."
I did as she said to, and soon enough my entire dick was in. It was so tight, and so amazing. I started thrusting harder and faster. We were both moaning, and I was about ready to cum. I told her I was going to cum, but she didn't listen. Before I knew it, I came without pulling out. I did pull out, though, and my cum trickled out her ass. We were both exhausted, so I held her and we fell asleep.
