I leaned against the fence watching 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 would feel 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. 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 at school.

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 min 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 top 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 in 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 it 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 noted 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.”

“I think men are dickheads expecting sex just because they pay for dinner and a movie.”

“It’s not that we expect it, Vanessa. But if we get along, and like each other, that would be the next logical step. In your case, did you actually like or feel attracted to these guys?”

“Sure, I did. Apart from Marcus, I really liked Mike and Greg, but both of them dumped me after four or five dates.”

I leaned back in the chair putting my hands behind my head and studied my friend. Maybe I was wrong in assuming a girl like her, looking like she did would be a beast in bed with vast experiences. She might be as shy and nervous I would be around a woman.

“Why don’t you want to do it?”

She sighed. “I think it’s because I’m afraid he might not like it.”

“Oh c’mon, Vanessa. That’s the lamest excuse I have ever heard. It’s not that hard, grab the guy’s dick and jerk it up and down. Watch a porno if you want more education.”

She laughed and blushed. “I guess you are right, but still. What would happen if he didn’t like it, I would be devastated?”

“Trust me, any guy would love you giving them head or a hand job. Just look at your lips, they are made for sucking cock.”

“Ben!”

“Shit, sorry, that came out wrong. More juice?”

She handed me her glass and I filled it for her while thinking about a nice come back after what she had said.

“When is your next date”?

“This Friday.”

“Which means you have a week to study up.”

“I guess.”

“Watch some porn, talk to one of your girlfriends.”

“Hell no, they think I have the experience. I kind of lied to them and told them I was with a few guys last summer when we were on vacation in Florida.”

She finished her juice and got up. Walking her to the door I said, “I don’t have any experience being jerked off or sucked, but if you have a question, maybe I can help out.”

“Cool, thanks, Ben,” she kissed my cheek and she smelt so nice my cock came awake. I had it out and jerking it in the bathroom before she had reached her front door.

*****

On Wednesday my phone rang and it was Vanessa.

“Yeah?”

“Ben, can I come over, are your parents at home?”

“Yes and no. Mom should be back in a couple of hours.”

She just hung up and then a saw her run across the street so I went down to open the door.

She grabbed my hand and went up to my bedroom with me in tow. “What’s going on,” I asked when she had sat down on my desk.

“I did what you said, watched some porn but as I have never seen or touched a dick I was wondering if you could show me yours?”

My head began to spin. Here was the most beautiful girl in the world, the love of my life asking me to show her my cock.

“Why?”

She stared at me. “I just told you.”

“Sure, but the day after tomorrow you can do it with Marcus.”

“That’s the whole point. I am asking you so I know what to expect when I see his.”

“No, no, you can’t do that. It would be cheating, plus I’d feel like some kind of guinea pig.”

“Ben, we have been friends for a long time, and if I don’t remember wrong, we used to skinny dip in my pool back in the day.”

“Sure, we were in kindergarten then, and it’s not the same thing.”

“Please, I beg you. What does it matter to you?”

“It just feels weird showing my dong to you.”

She giggled. “That’s a funny word for it.”

“Glad you liked it, but the answer is still no.”

She began to pull up her T-shirt exposing some of her flat tanned tummy and I looked away.

“I know you want to look, Ben. Didn’t you tell me I was part of your masturbation fantasies?”

Still looking away I mumbled. “Yeah, but that’s just fantasy.”

“What if it became reality? What if I let you see me naked and you could masturbate at the same time? It’s a win, win situation; we both get what we want.”

I turned back to her, the idea wasn’t too bad. “Are you sure?”

She pulled her T shirt over her head and unclasped her bra which fell to the floor. And there they were in all their glory. I didn’t know much about boob size and bra cups. But by my estimate, they were bigger than my hand with tiny nipples.

“You get to see the rest once you have your dong out,” she said with a grin.

I slowly lowered my shorts together with my underwear until I could push them down with a foot and then step out of them. I already had a hard on, in fact I had had one since she entered my bedroom.

She stared at my dick without saying a word then in a whisper, “Can I touch it before, you know, you do your thing?”

I was shaking with excitement. “Okay.”

She slowly moved her hands towards me and then wrapped her fingers around the shaft. “Fuck, it’s so warm and hard. Does it hurt?”

“Nah, not at all, it just feels right.”

Her eyebrows knotted. “What about your cockhead?”

“I got a long foreskin, just pull it back.”

“Oh, oh, shit, look at that. It’s like a red mushroom.”

And that’s when I shot my load onto her hand and wrist.

“What the fuck, Ben!” she let go and jumped back to avoid the following two squirts.

I felt like a real idiot, such a dumbass and my face blushed with shame. I turned around and said, “I’m so, so, sorry, Vanessa.”

“Do you have a tissue?”

“On the desk.”

I heard her wipe off the cum and throw the tissue in the bin. I was still with my back towards her when I heard her laugh.

“What’s so fucking funny? I already feel bad, don’t make it worse.”

“Sorry, but it was a bit of a shock, it came so fast.”

“I guess it did.”

“Is it always like that?”

“No.”

“Oh, so you can hold out longer?”

“Usually, a lot longer. I guess it was so fast since it was the first time a girl touched me.”

There was a silence where the tension in the room was almost unbearable. I had no idea what to say or do so I just stood there with my now flaccid dick. A strand of cum hanging from the tip.

“Vanessa, pass me the tissues, please.”

“I have a better idea, turn around and I will help you clean it.”

I did and she went down on her knees before me. She held the shaft with two fingers and then used two more to pull back my foreskin. Dabbing and wiping she cleaned off the cum and then let go of the dick. She watched it for a moment without speaking and then took it in her palm.

“It’s quite long, you know, even flaccid.”

That brought a smile on my face and I grew hard again.

“My god!” she said and let go of my dick that was now standing straight up.

I became brave and said, “You owe me a peek at your thing.”

“Yes, I do.” She wiggled out of her shorts and then pulled down her white cotton panties. They had small red bears on them, not what I had expected. I thought she would wear something sexy like a thong or string.

“What do you think?” she asked pointing at her vagina.

There was a tuft of brown hair just above the slit and under it a pink button peeked out. I knew that was her clit. I noted something else too, her slit glistered a little, like if it was wet.

“Can I touch?” my voice barely audible.

She nodded and closed her eyes. I reached out and with my index finger and drew a line from her clit down the slit and it came away wet. I did it again, and this time I let the tip of my finger linger on her clit and she gasped quietly.

“What?”

She giggled. “It feels good.”

“Yeah, what about this?” I began to move the tip of my finger in a circular way.

“Oh, oh, even better. Hang on, let me sit down.” She did on the end of my bed.

I knelt before her and she spread her legs a little. Her pussy was beautiful, with small thin lips and as I watched her clit actually swell in size. I reach out and this time I pushed my finger inside her a little. It was so warm and wet it sunk into the second knuckle.

“Oh shit, fuck, that feels good,” she moaned and lay back.

It dawned on me that I was doing what I had dreamt of since I became sexually aware. As I moved my finger in and out Vanessa responded by curling her fingers into the sheets and moving her hips, pushing against my finger, trying to get it further inside her.

My dick was leaking pre-cum by now and I thought about jerking off while finger fucking her but I lost that thought as her pussy cramped and she moaned loudly.

“Ben, Ben, I think I’m having an orgasm, oh.”

Think? This was getting weirder and weirder. Shit, I would have guessed Vanessa played with herself at least a few times a month, but apparently that wasn’t the case.

When she gave off one last long gasp I pulled my finger out and sat next to her on the bed. Her chest was heaving and her nipples hard. I flicked one and that made her open her eyes.

I pointed at my dick. “Help me out?”

She sat up and then pushed me down. Moving across my legs so she was between them she lay down and then looked up at me.

“Do I just suck it, or what do you like?”

“I have no idea, it’s my first time too, remember.”

She bent my cock forward which wasn’t very comfortable but I didn’t want to complain. Sticking out her tongue she licked the head and smacked her lips.

“It’s kind of sweet.”

Then she sucked on the head and I stared at her like if she was from another planet. Her lips stretched a little as she moved down my shaft and by the time her nose hit my tummy, they were tight around my shaft. She looked so sexy; I thought I would come fast.

Slowly bobbing her head she realized that the angle was all wrong and scooted up a bit, still with my dick in her mouth.

“Oh, Vanessa, that’s amazing.”

She winked at me and began to move faster and faster. This wasn’t good. I didn’t want to squirt in her mouth, at least not her first time.

“Hey, hey, slow down, or I will come too fast and in your mouth. I will let you know when I’m ready."

She did what I asked, licking the shaft, my nuts and the head. Then down to the base and up again.

“Vanessa, any second now, almost there.”

From my moans she knew it was time to pull back which she did, just in time as I shot three times straight up in the air.

She giggled and then spread the cum out on my skin with a finger, still holding my dick.

“It’s so warm,” she said and tasted her finger, “doesn’t taste that bad either, you know.”

From the floor came the sound of her mobile and when she reached for it, she quickly got up. “Fuck, my mom is back. I got to go.”

She left me on the bed with a grin on my face and thoughts about how it would be to fuck her.

******

The evening Marcus picked her up I stood in my window looking down at them. It hurt that it was him and not me taking her out and I wondered if Vanessa understood it. We hadn’t met up since that day in my bedroom, only chatted a few times and neither of us mention what had happened.

I went down and hung out with my parents, watching TV and eating pizza. I wondered how Vanessa’s date was going. By the time it was nine in the evening I presumed she was sucking his cock in the front seat or at least giving him a handjob. I went to bed and felt miserable.

My phone rang and woke me up. It was way too early and the sun had just begun to rise over the treetops outside my window.

“What?”

“Ben, come over.”

“Fuck, it’s too early, Vanessa.”

“Please, with sugar and a nipple on top.”

“Fine.”

She opened the door in her nighty which was a long pink T-shirt with a red elephant on the front. I could make out her nipples pointing at me and my morning wood rose to the occasion again.

“What is so important?” I asked when she had let me in.

“Listen.”

“To what?”

“Exactly, Mom and Dad left early to see Aunt Karla. We have the house for ourselves.”

She took my hand and led me to the living room. Sitting down in one of the leather chairs she crossed her legs which showed off her long smooth legs.

“I was with Marcus last night.”

I sighed. “I know, I saw you leave.”

“Don’t you want to know what happened?”

“Not really, no.”

“Don’t be such a dick, Ben. Anyway, after dinner we went to the lake and began to kiss. A few other cars were there so we stayed in his. He used his hand to move mine to his pants so I knew what he wanted.”

“Uh”

“His dick is smaller than yours, by a good inch if not more,” she giggled and grinned at me.

It did make me feel better to be honest. If Marcus had had a major size dong I would have been worse off.

“I jerked him off and licked it a few times but never took it in my mouth.”

“Why not?”

She shrugged her shoulders. “Not sure, I guess it didn’t feel right. He did come fast though and messed up his trousers and shirt. After that he took me home.”

“Okay, thanks for that. Can I go back to my bed now?”

She uncrossed her legs and pulled up her top, she had no panties on. She slid a hand down past the tuft of hair while putting one foot on the armrest. Her lips parted and I saw that pink wet hole I so much craved to stick my cock in.

“What are you doing, Vanessa?”

“What does it look like? I made a decision last night. I want you to be the guy who takes my virginity.”

There was a long silence while I let that sink in while watching her caressing her by now swollen pussy lips.

“That’s sweet of you and I would love to but don’t you think it would be better with someone more experienced?”

She shook her head. “No, it has to be you. I know you will be gentle and nice with me.”

Who was I to say no? This was what I had wanted all along but at the same time it now felt weird and not so okay. She wasn’t in love with me and she didn’t want to be my girlfriend. All she actually wanted was to get rid of something, her virginity.

“I don’t feel right about this.”

She tilted her head. “Okay, I can understand that. Why don’t we just go to my room and lie on the bed and talk.”

“Sure.”

Her bedroom had changed since I had seen it last. Gone were the pink fluffy animals and the posters of boy bands. Now it looked more like a grown woman’s room. A computer, desk, pens and pencils in a holder. Walls were off white, no posters, just a clipboard with notes and photos of her friends doing silly things.

She went over to the bed and beckoned me to follow.

“This is nice,” she said when I lay on my back next to her. My arm touched the soft skin of hers and she held my hand.

“I guess I’m afraid of losing my virginity and that’s why I asked you. It’s a big ask, I know. Maybe, at least, could you think about it, there is no rush.”

Her top had ridden up and more than half of her thighs were visible. I tried not to think were they lead but there was no escape, my dick came awake and pushed against the front of my shorts.

“Oh, is that what I think it is?” she asked and pushed herself up on an elbow so she was kind of leaning over me.

“Mm.”

She put her hand on it and gently pressed down flattening my cock against my tummy. “It’s harder than Marcus’s.”

“Could you please stop mentioning him while touching me?”

She giggled. “Sorry. You know what? I think someone needs to be freed.”

She opened the button and pulled down the zipper and squealed when she saw I didn’t wear any underwear. “Oh, you are going commando, Ben. That’s so sexy.”

By now my dick was hard and the cockhead showed a little. She used her index finger and tickled me just under it and my cock jerked from the attention.

“Someone is anxious to be played with.”

“I guess.”

She turned to me, coming closer and closer until I felt her breath on my lips. Then she kissed me at the same time as she grabbed my cock and began to stroke it.

She tasted of toothpaste and something else, maybe Chap Stick or lipstick, strawberry, I wasn’t sure since all I really cared about was making out with her. I snuck an arm under her and pulled her closer, feeling her breast push against my side. My hand landed on her ass and slowly I pulled up her T-shirt, waiting for her to tell me to stop, but she didn’t. Instead she kissed me harder and deeper. Letting go of my cock she rolled over me and my hands were on her warm and soft ass-cheeks. Her hands were on my cheeks and neck, and she was kissing and sucking on my tongue.

“Ben, oh, Ben, I want you so much.”

Her whisper was in my ear and then she began to take off my T-shirt and I hers. We fumbled and laughed as we became naked together.

“Are you sure?” I asked when I felt her pussy slide over my dick.

She looked me in the eye and slowly nodded. “Yes, you might not believe this but you have always been special to me and I want us to have this experience together.”

She grabbed my dick and lowered herself until the head slid in a little and then let go. She put her palms on my chest and began to push down but nothing happened. I felt and noted her frustration.

“Slowly, take it easy, there is no rush.”

“But I want it now, I’m so fucking horny,” she said before pushing down a lot harder and this time I entered her.

“Oh fuck, fuck! That hurts,” she whimpered with her eyes closed.

She was still, not moving a muscle. I gently put my hands on her hips, her skin soft and warm against mine. She leaned forward and I licked her nipples in turn which made her moan.

Slowly and almost tenderly she began to move, not up and down but in a circular motion, grinding into me.

“Vanessa, you are so warm and wet.”

“Do you like it, baby?”

“I love it and you, you know that right?”

She kissed my forehead and then my mouth. “I do.”

Her circular motions stopped and she began to ride my shaft, slowly and gently at first. Her nails cut into my skin and I gasped a little before her lips touched mine. My hands came around her and grabbed her ass cheeks and I began to meet her with my own thrusts.

“Ben, Ben, you are fucking me, fucking my pussy!”

She moved faster and faster, and straightened up, taking her perfect boobs away from my reach. Almost sitting on me she cupped them and pulled at the nipples. Her body had a film of sweat and her eyes were half closed as she threw back her head.

“I’m coming, Ben, I’m coming, coming, ah!”

Her pussy tightened around my shaft, sucking it further inside as I held her tight. I pulled her down so she lay on my chest and the last of the cramps from her pussy ebbed away. She giggled. “You didn’t come.”

She was right, I hadn’t and I felt very proud. “I guess I could hold back.”

With a dirty look she turned herself around so her pussy was over my face and she took my cock in her mouth. Pulling her down I began to lick her lips and suck on her clit while she deep throated me. Within minutes my load erupted but she didn’t stop but kept on sucking until I was empty and by then she had come too.

“Ben, that was amazing.”

“Didn’t it hurt?”

She was on her back and stretched out like a cat. “It did, and it still does, but it’s a nice pain, a pain that makes me a woman now.”

I kissed her cheek and was about to roll over her again when she reached for her phone.

“Who are you calling?”

She smiled at me. “I’m dumping Marcus.”

“Really?”

“Yeah, I want you to be my boyfriend.”

I got tears in my eyes and wiped them away while she dumped him by text message. When she was done and had put the phone away she turned to me.

“Were you about to fuck me again, in a missionary position?”

I nodded.

“Well, why don’t you just do that, stud!”

When I entered that warm place and she put her arms around me and held me tight, I was the luckiest teenaged nerd in the world.