I leaned against the fence and watched the cheerleaders practice their routines. The sun was warm on my back and a drop of sweat ran down the side of my face. I wiped it off, not sure if it was because of the heat or me being horny. Vanessa did a few cartwheels and came to a halt only a few yards from me. When she saw me she waved.
"Hi, Ben!"
I waived back but didn't have time to answer her because she ran back to her friends. She was so hot in her uniform and long tanned legs. When she jumped or ran her boobs bounced and I wondered what they felt like to hold in my hands. I sighed, that would never happen, I knew that. Vanessa, even though I had known her all my life was out of my league. This was the year we graduated. We had both turned eighteen during the winter and in the fall we could go to different universities. She was the girl all the boys wanted to date. Even though she was popular she never dissed me or acted like she didn't know the nerd in the glasses and suspenders. When we were younger we would play together but as teenagers her group and my group of friends didn't hang out. Actually, they usually sat on opposite sides of the cafeteria.
They finished their practice and Vanessa made her way over to me and I again took in her body and especially those tits of hers. They were a fixed item in my spank bank and I used them frequently to get off. I know, I was a sad case of a young man.
"What's up, Ben?"
A thin film of sweat covered her skin and a drop had formed right above her cleavage.
"I'm on my way home and thought we could walk together."
"Cool, let me get my stuff."
I waited by the little gate and when she came up to me she put her arm under mine and we began the fifteen minute walk to our houses.
"So, any girls in your life, stud?" she teased.
"I wish, but you know how it is for us nerds, it's all about dreaming and fantasizing."
She bumped her shoulder into mine. "You can fantasize about me all you want, I don't mind."
I blushed and she must have seen it. "Oh my god, you do, don't you. I was just joking about it, Ben."
"Sorry."
We walked in silence and then she said, "Really, do you actually, you know...?"
I thought about lying but then I remembered how she had never lied to me and she had always been there for me especially when my parents got divorced.
"Yeah, I do."
"Oh my god, Ben, I can't believe it."
"Why not? You are very pretty and have a hot body."
"Thanks, but being your jerk off fantasy doesn't really make me feel better."
"Again, I'm sorry."
"What about Becky and Amanda?"
They were her friends, also cheerleaders and hot.
"Sure, I like Amanda, her hair is just amazing."
"Mm, so you like redheads. I'll tell you a secret. She shaves her you know what."
"Oh fuck! Vanessa, why did you have to tell me that?"
She looked down at my pants. "Did that make you get a hard on, thinking about Amanda's shaved pussy? I'll tell you something else, she has amazing boobs. Not as big as mine, but so fucking firm she doesn't even need a bra and her nipples, they look like little raspberries."
"Fuck you, let it go, okay."
She laughed the rest of the way home and when she stopped at her front door she said, "Look, I don't mind you doing what you do, but please, take the other girls into consideration and spread your seeds among us all."
"Bitch!"
She laughed again, and when she closed the front door I trudged home with my hard on and thoughts of Vanessa going down on Amanda. That would be so hot.
On Friday evening that same week I was in my room playing on my computer when I saw a sleek sports car come to a halt outside Vanessa's house. I put down the joystick and got up. A guy a few years older than I got out, and then walked up to the front door where he rang the bell. A few minutes later Vanessa opened and gave him a hug. It was one of those movie hugs where the girl bent her leg at the knee. She gave him a kiss on the cheek and then they both walked to his car. A date. My heart sank and I sat down at my computer again, frustrated and sad. Not only wasn't I going to get a date with her, she would have another guy's dick in her. Fuck, life was unfair.
A few hours later they came back and the dude walked her to the door where they kissed goodbye. It wasn't a French kiss, more of a peck on the lips. When she walked inside the guy turned and if I wasn't mistaken, his shoulders slumped and he looked frustrated. Hope peaked inside me, maybe the date was a failure and there wouldn't be any more?
"Hey, Vanessa." I called out the following morning. I was walking our dog and Vanessa came jogging towards me. She had black spandex pants and a sports bra which couldn't control her boobs.
"Hey." She patted the dog and ran in place. "What's up?"
"Sorry to be nosey, but were you on a date last night?"
"Why? Are you spying on me or something?"
"No, I just happen to see you get into a car."
"If you have to know, yes, I was on a date. His name is Marcus and he is in college."
"So he is older? What do your parents think?"
"Nothing, it was our first date."
"Okay, well, I was just curious."
She jogged away from me and I watched her ass, hoping to god Marcus wouldn't be tapping that in a while, or never.
A month passed and every Friday and Saturday Marcus would pick her up. The goodbye kiss had gone from a peck to hard core making out. His hands were on her ass and once I saw him squeeze her boob. That made my stomach turn and I had to look away. Another time he slid his hand down her thigh and when he moved it up the hem of her skirt followed and by the time he let go, I had seen a part of her panties where they curved into that holy spot, also called a pussy. After that, I went to my bed, lay down, and jerked off until I shot a huge load of cum which in my fantasy landed on Vanessa's firm tits but in reality landed on my thighs and ran down onto the sheets making the bed wet. I was miserable.
The following morning, which was a Sunday, I was having a late breakfast alone at home. My mom had gone to visit a friend and I would be able to watch TV all day without her bothering me.
The doorbell rang and I swore under my breath since I thought it was my mother who had canceled with her friend. I was still in my boxer shorts when I opened the door.
"Hi, Ben, can I come in?" Vanessa stood outside wearing cut of shorts and a halter top, squeezing her hands together, obviously nervous about something.
"Yeah, sure, do you want a drink?"
"Juice?"
I lead the way to the kitchen where she sat at the table and I poured her a glass of apple juice.
"Are you okay?" I asked while she drank.
"Something has happened, and I'm not sure how to deal with it."
I sat down. "Do tell."
"Marcus wants to get sexual."
"And?"
"Well, the truth is, I don't have much experience." She said looking down at the glass she was twirling in her hands.
"C'mon, Vanessa, don't give me that crap. I know you have dated a few guys over the last year or so. So don't tell me you don't know what to do."
She looked up at me. "It's the truth. Why do you think they never lasted?"
She was right, I had noticed that too. She would go on a few dates but then the guy would be gone and a couple of weeks later a new guy would pick her up and the same thing happened.
"What you are telling me is that they dump you because you won't let them have sex with you? What about a blowjob or a hand job?"
She shook her head. "Sometimes they call me a cock tease."
I laughed. "Well, my friend, you earned it, didn't you. You dress sexy, act all hot and flirty but then they don't even get a hand job. What did you expect?"
"Oh, fuck off, Ben. It's not like you are the big lover with loads of experience."
"True, but I'm a guy and as such I know what I would expect, or at least hope for after a few dates if we liked each other."
