Teen Sex Story. High School Nerd – Wednesday



It is a lovely day to walk home from high school. Normally I catch a ride with Robert, my neighbor. But cheer practice kept me at school late and Robert had already left. He and I had been intimate a couple of times, but I needed to keep him wanting more so I could extract favors from him. Walking home today is not a problem. The sun is shining, the birds are singing, and everything is right with the world. I need to get in some more cardio, anyway. Arms swinging at my side, I walk at a brisk pace.

Suddenly, up ahead I spot a girl in a cheerleader uniform, just like my own. Who on earth could it be? The girl is walking beside a tall fella, with light brown hair. Already walking at a brisk pace, I pick it up some more to see who this is. Closing the distance, I can’t believe my eyes. It is Sandra, laughing and talking with Henry, the uber nerd from school! Sandra was missing from cheer practice today. Putting two and two together, it is not hard to figure out what happened. Sandra played hooky with Henry! But that’s crazy! Just Monday she dissed him, listing him as one of the last guys that she would want to make out with.

As they walk, Henry pulls something out of his back pocket. It is a light blue cloth. He opens it up and holds it up, examining it. They are laughing at it, whatever it is. It’s hard to tell from here, but it kinda looks like a girl’s panties? But that can’t be! Maybe it’s a hanky? I wonder! He shoves it back into his pocket and they continue down the sidewalk.

The way that they are interacting, they seem very companionable, like they have an intimate connection. What could they have been up to this afternoon? Could they…? No way! They couldn’t have been making out, could they? Not with the way she talked about him. But that would fit with the way they are acting. Now that I have verified who it is that I saw, I drop back and let them get ahead before they see me. You know, Henry doesn’t look too bad.

Walking slowly the rest of the way home, I think about what it might be like to be with Henry. He is not as buff as some of the guys, but he is tall and slender. He normally doesn’t talk very much, but he sure seemed to be having a good time with Sandra. I wonder if I could get him to open up with me? He has striking blue eyes. That has got to be his best feature. Of course, Jazz mentioned that he seems to have a huge bulge in his pants. Maybe his eyes are his second best feature? Who knows? I wonder if he knows how to use what he has in his pants? The girls say that he does not know how to kiss, but watching him with Sandra, I’m not so sure that is true. Maybe I should find out for myself? Maybe it would even be fun to teach him?

The rest of the afternoon and evening, I could not stop fantasizing about being with Henry. I must admit that it is becoming an obsession with me. Thinking of him is making me all hot and tingly, and I have got to do something about it. I am already scheming about how I might seduce him tomorrow at school, but I can’t wait that long for some relief from the tension that I feel. I turn in for bed early, securely locking my bedroom door.

Crawling into bed, I turn the lights down low and open the bottom drawer of my nightstand. Reaching in, I pull out my magic wand. No, I’m not a witch. It’s not that kind of magic wand. You girls will know what I’m talking about. I spent the extra money and got the good, cordless one. It has variable speed and all the settings. Placing the head of the vibrator against my pubic bone. I have it set to deliver slow, soft vibes. The low frequency penetrates through my bones and makes my entire pelvic region thrum. I have been building Henry up so much in my mind, that now he just oozes sexuality. I still wonder if it was really panties that he was showing off? Could it have been Sandra’s?

I imagine him begging to be with me. I imagine him taking my panties off. In my head, I see Henry eating me out, splitting my little peach of a pussy with his tongue, lapping up all of my peach juice. Flicking my clit with his tongue.

Now that my engine is started, it’s time to bump up both the speed and intensity of the vibrator, a couple notches. Guiding the Vibrator down lower, I apply pressure around my opening. Now I imagine Henry inserting a finger, no, two fingers. He is doing a come hither movement that hits my G-Spot. After a couple minutes of that it’s time to turn the speed up a couple more notches. I reach back into my bottom nightstand drawer and find my soft, anatomically correct rubber dildo. Inserting it adds a feeling of fullness. The head of the vibrator migrates back up, teasing my clit, then runs back down, connecting with the dildo. Then back to my clit again. The vibrator causes the entire dildo to vibrate, deep inside of me. The tingling is felt all the way to my foundation, and it makes my toes curl. With my left hand, I play with my nipples, rolling them between thumb and forefinger and tugging on them. The sensation reaches a fever pitch and I feel myself fall over the edge of the precipice. My body bucks and spasms three times, involuntarily. Now I can’t stand for the vibrator to touch me, and hit the button to power it down. I imagine French kissing Henry in post coital bliss.

Putting my magic wand back in the drawer, I make a run to the bathroom. I look in the mirror at my face. I love the way my face looks, right after cumming. My face and chest are flushed and engorged. My lips are full and swollen, making them look pouty. Observing myself in the mirror, I purse my lips and imagine kissing Henry with my soft, full lips. Looking down from the mirror, I close my eyes, take a slow deep breath and splash cold water on my face. I got to quit this and get some sleep. Cheerleaders need their beauty rest, after all. The cold water is bracing and refreshing. I feel sassy and satisfied. I clean up and wash my face. Crawling back in bed, I spoon with my imaginary Henry, a full body pillow, and soon fall asleep.

I feel great as I wake up in the morning. It is amazing how much a good orgasm helps a girl to sleep. I am anxious to tackle the job of seducing Henry! I wonder if he will be half as good as I have been dreaming of? It’s unlikely. He is shy and inexperienced. Also, I have to figure out how to seduce him. That may not be so easy. Not if Sandra already has her claws in him.

Thinking about it, I am sure that Henry and Sandra were not aware that I saw them on the way home from school yesterday. I think I will just keep that little tidbit to myself. I am almost beside myself with curiosity around what all they did. Cheer practice lasted for 45 minutes, so they were probably together for about that long. Where would they have gone to be alone at school? I cannot think of anywhere that would be safe from someone walking in on them. Maybe all they did was go to the library and talk? Hah! I don’t believe that! I’ll have to see if I can get anything out of Sandra.

There she is down the hall. I hurry to catch up with her. “Hey, Sandra,” I say to her. “Missed you at cheer practice, yesterday afternoon.”

“Oh, yeah. I wasn’t feeling up to it.” She said, not making eye contact with me.

“Sorry to hear that.” I say. “We practiced our tumbles. It was a lot of fun.”

“I hated to miss out.” Sandra remarks. “Maybe next time.”

Changing the subject, I say, “By the way, someone said that Henry stayed late yesterday. I wonder what he was up to?” I asked.

Sandra looked up at me, then looked away. “You know Henry. He was probably studying late. Not sure why you think I would know where he was?”

“Just thought you might have seen him, since you weren’t at practice.”

Sandra didn’t offer anything else, but eyed me suspiciously. Now I pretty much know that they were not just talking or studying together, or she would have said so. I am so curious where they could have gone off to together, and what they did. I have to think of a way to get it out of her.

Keeping an eye on Henry and Sandra throughout the day, I notice that they keep making eye contact and smiling. There is definitely something going on between them. I will need to pull out all the stops if my seduction is to be successful.

At lunch I sit with the other girls on the cheer squad. Jasmine asked Sandra about missing practice yesterday, and Sandra gave her the same excuse about not feeling well. We talked about other things and I noticed that Sandra sat where she could keep an eye on Henry, where he sat eating alone.

At study hall I decide to make my move. I walk over to the table where Henry sits alone, put my backpack down and ask to sit with him and study together. He looks at me quizzically, then offers me a seat. When he smiles, he has the cutest dimples. I have never noticed them before. He does not try to act tough or aloof like the cool guys do. He acts self confident and real.

“Let’s see. You are…”

“Linda. My name is Linda. You are Henry, right?” I say.

“Guilty as charged. Well, Linda. Is there anything in particular that you need help with?” Henry asked.

My thoughts went back to the fantasy that I indulged in as I was masterbating last night. That’s what I really need help with, but it might be best not to go there, just yet. “Well, I am pretty clueless about the American literature assignment. That, and I would love to get to know you better. You seem kind of shy.” At this, Henry blushed and reached for his Lit book.

“Well, I guess we are supposed to have read Thomas Jefferson, Notes on the State of Virginia. Have you had a chance to read it yet?”

“Most of it. But I am not sure that I understand what the real significance is,” I say.

“I think what they are looking for is the places where it alludes to the politics of Virginia, as a British territory. Let’s review the notes on that.” Henry pulls up something on his phone and reads it to me.

“I see. That makes sense. Thanks. Now tell me about yourself. Do you have any hobbies? What is your family like? What are you really passionate about,” I suggest.

“Wow. Where did this come from?” He asks.

“I don’t know. You are kind of cute, and I want to get to know you better. Has anyone told you what beautiful eyes you have?”

“My mom has mentioned it. But thank you,” He says

“I have an idea. Would you walk me home, after school? I think I just live a couple blocks down the road from you.” I suggest.

“Sure. I don’t see why not. Yeah. I would love to walk you home today.

“Wonderful!” I say.

“Now tell me about yourself,” He asks

“What can I tell you about me?… ” I try to share a few things about myself.

At the end of school, I find Henry at his locker, putting away most of his books. Sandra is talking with him, and she is all smiles. They stop talking when they see me approaching.

“Hey, Linda. You ready to go?” Then he turns to Sandra and says, “Sandra, you know Linda? I promised to walk her home from school this afternoon.”

Sandra’s face falls, “Oh,” she says. She pauses and seems to be considering something. “May I go along?” Henry is facing Sandra, so I shake my head vigorously where only Sandra can see. “Oh, snap.” She says. “I need to drop by the store on the way home. Maybe some other time?”

“OK. Sure, some other time.” He says. He looks really confused, like he knows that he is missing something.

On the way home, Henry and I talk pleasantly about our families, our aspirations, our frustrations and plans for the future. I don’t tell him this, but my plan for the afternoon is to invite him into my house. I already know that no one will be home. When I get him where I want him, I must work to seduce him. I will have to figure out what turns him on. Guys are not that complicated. They are visual. I have something I want to try. The anticipation is killing me. If I fail, it will mean another date with the magic wand, tonight.

“Thanks for walking me home,” I say as we approach my house. Can you come in for a bit?” I ask.

“Oh, I don’t know. I should probably be getting home. It has been nice talking with you,” he says.

I mustn’t let him slip away. “No, please. Can’t you stay? You can help me study. No one else is home, and I hate to stay by myself.” I am pleading, now.

“Well, just for a little while.” He concedes.

I take him into my house. In the kitchen, we gather some snacks and soft drinks. I try to work close to Henry, squeezing into his personal space. We talk about our favorite movies, the music that we like, and even about sports. It is surprising how much we have in common. He helps me carry the snacks and drinks to my bedroom. We sit on the edge of my bed, hip to hip. Turning to face him, I ask, “Do you have a girlfriend?”

Henry looks taken aback by the question. When he recovers, he answers, “Well, no. I guess not.”

“Do you like girls?” I ask.

“Well, yes. I do.” He stammers, wondering where this is going. He looks uncomfortable, embarrassed.

I get up and turn on my Bluetooth speaker, and start some music from my phone. The lights are not on in my bedroom, but golden afternoon light streams in through the windows. “What kind of girls do you like?” I ask. Removing my hair tie, I shake out my ponytail. Henry watches me with interest. He seems to be relaxing with a little more distance between us.

He thinks about the question for a minute before answering. Then he says, “I like girls who are kind and interested in other people. Girls who are smart and are trying to get somewhere in life.”

Since starting the music, I have not sit back down. Instead, I slowly move about the room. I move left to right, closer then further away. I try to move in time with the music, not quite dancing. The goal is to get Henry to follow me with his eyes. To really look at me. I continue, “Do you like pretty girls? Girls that are sexy?”

This question makes Henry blush a little, and he looks away for a moment. Then he looks back at me and says “Sure. That’s always nice.” He grins as he says this and his dimples appear, making him adorable.

“Please be honest with me,” I say. “Do you think that I am pretty?” I pause in my movement, and strike a demure pose.

“Yes. You are stunning!” He says without hesitation.

I continue my movement across the room, coming closer then further away. “Do you think that I am sexy?” I press on.

“Absolutely. Who can resist your charms,” He adds.

I continued to move about the room in time with the music, but now I start to slowly unfasten buttons on the front of my pink cotton blouse. “Tell me what you like best about me?” I continue with my questioning.

Henry has noticed that I am opening buttons, and he is getting distracted and takes longer to respond to my questions. “Well, I like the way you move. You are so lithe and graceful. I also like your smile, and the way that you laugh. And of course I love your physical features.”

“My physical features, huh?” I reply. “Specifically what physical features are you thinking about right now? Don’t be shy.” I now have all the buttons open. I hold my blouse open, exposing my boobs in a pink lace bra. I catch a glimpse in the mirror on my dresser behind where Henry is sitting. My erect nipples and areola are visible through the sheer lace. Henry is looking at me like a very thirsty man. I hold my blouse open and give him a chance to appreciate what he sees. Is he undressing me with his eyes, I wonder? I pirouette in a double spin, losing the distance between us.

Pausing my movement right close in front of him, my blouse is wide open. “OK, if we are freely speaking our mind. I love your breasts,” he confesses, looking at them near his eye level. “I would love to be able to touch them,” he says eagerly. His hand rises toward me.

“All in good time,” I explain to him, and move away from him again. I want to escalate the level of his arousal some more. Continuing with my Informal dance routine, we exchange questions and answers in an attempt to learn more about each other. “Did you know that a man is not really complete without a woman?” I ask.

“Uh, how so?” He asks. I continue to move about the room, finally flinging my blouse off and away from me. Now I am dressed in my bra, a short red skirt showing plenty of leg, and panties.

“Ladies are the yin to a man’s yang. Men are unyielding and forward, ladies are gentle and reserved. Men have hard, strong bodies and ladies are soft and supple. Men are cold and logical and ladies are warm and emotional.” I say. “Together we are balanced and complete.” Now I have moved away to the corner of my room and stop, facing away from Henry. With my legs apart I bend at the waist, running both my hands together down one leg. Moving slowly, sensuously I stretch all the way with my fingers reaching beyond my toes. This should cause my pink panties to peek out from under my short skirt in the rear. Hopefully he can see my tight buns. I hold this position for a moment before slowly straightening and continue to move about the room.

Henry replies, “I can see that.” His voice sounds more distant, like he is not concentrating as much on what he is saying.

“And not only that, but men and women are made to give each other pleasure. Did you know that, Henry?” Now I am standing near him again, and I stretch and reach with my hands together, up towards the ceiling, then bend backward. My hope is that this position gives him a peek at the front of my pink panties, under my skirt. Of course it also gives him a birds eye view of my flat belly, my narrow waist and my tits in my lace bra. I wonder which one holds the most fascination for him? I hold the position for a beat, then move on, making him want more.

“Don’t people just focus on what they can get out of a relationship? It seems to me that people are selfish and self-serving in relationships like that,” He says.

Moving slowly away, I say, “Please take your shirt off for me, Henry. Too many relationships are selfish and self-serving, that is true. But for us to have a strong, fulfilling relationship, I should try to bring you pleasure, and you, in turn, try to fill my needs. We should not focus on our own fulfillment, but that of our partner.”

Henry looks thoughtful at what I have said. I am afraid that he has forgotten about my request to take his shirt off. Either that or this might be where my seduction breaks down if he refuses to take clothing off. Then he seems to remember, and pulls his T-shirt over his head. As he does so, I unfasten my bra, while he is distracted.

After he has his shirt off, he says, “That’s an interesting point of view. It seems like it should work.” Then he notices that I have removed my bra. He is shocked and slack jawed. I twirl my bra around on a finger, dramatically, before flinging it to a corner near where my blouse has landed.

Now as I dance around the room with my breasts free, they jiggle and sway with my movement. I notice Henry’s chest and arm muscles. He is pretty well put together. I can also see that Henry’s pants are getting tighter in the crotch. I say, “When a man and a woman are focused on meeting the needs of their partner, it creates perfect fulfillment. We can never satisfy ourselves as well as our partners can satisfy us. But people are naturally selfish and move towards thinking only of themselves. That is why a good relationship takes work.”

Henry is definitely fascinated with my breasts and is watching intently. I’m not sure now if he is even thinking about what we are talking about. He is totally distracted by my boobs. It’s a wonder he can think at all, with all the blood his body is sending into his cock.

Moving again to the far side of the room, I do a slow twirl and am able to unfasten my skirt. It pools on the floor at my feet. Lifting it with a toe, I fling it to the little pile where the rest of my clothes have landed. Now I am in only my pink panties. I fear that the little padded area in the crotch is dark with my wetness. With my legs at a wide stance, I hike my panties up as high as I can, pulling at the waistband in the front. I tilt my hips back, forming a nice camel toe. The narrow strip of fabric is not enough to cover everything, and I know that my outer labia is bulging outside the cloth. It leaves very little to the imagination. I continue to move about, feeling inspired to swing my hips about in time with the music. Henry has a crooked little smile, which lets me know that he is still following along for the ride.

I say in a husky voice, “Henry, could you remove your jeans for me? Please?” This is a crucial moment. Asking for him to remove his pants plainly says where this seduction is going. At this point, he might lose his cool, clam up and refuse. If he follows through with my request, then I pretty much have him in the bag. To my relief, Henry does not hesitate. He unfastens his belt, then his jeans. Then he stands from the bed for a moment to slide them off. He folds them and lays them on the floor beside the bed. He is only wearing mint green boxers that say ‘The Luck of the Irish,’ on them. I like his sense of humor. If I get my way, it will indeed be his lucky day.

Two slow, sensual songs have played. Now something with a faster dance beat cues up. I slip my panties off and dramatically twirl them about on a finger before flinging them onto my clothes pile. The music invites me to become more energetic. I begin doing some of our cheer routines. This involves splits, squats, clasps, jumps, and even a tumble. I do all this completely nude.

When the song ends, I am out of breath. Looking at Henry through my disheveled hair, I am anxious to gauge his reaction. I am pleased to see a huge grin on his face and he begins to applaud. He stands to his feet, I spread my arms and bow deeply. When I straighten, I comb my hair back out of my face with my fingers. I am pleased to see that Henry has removed his boxers, all on his own, and is as naked as I am.

He has sit back down on the edge of my bed. I walk over to him and settle my bare ass on his knees, facing him. I look deeply into his true-blue eyes. We hold each other’s gaze, then embrace and he smothers me with his kisses. My breasts are crushed into his chest. It is difficult to sustain this kind of a kiss, since I am still breathless from my routine. I am surprised what an accomplished kisser he is. I remember it was Sandra that thought that he would piss himself if he had to kiss a girl. What would the girls think if they could see him now! I can’t believe that he is here in my bedroom, kissing me, and both of us naked.

When we end our kiss, we gaze into each other’s eyes again, not speaking. His gaze travels down to my boobs, still heaving since I am a little out of breath. His hand rises and he gently hefts one of my boobs, then bends forward to plant a kiss on my nipple. His eyes move still further down, and he checks out my little dark brown landing strip, just above my open pussy. It is open because my legs are spread wide to sit on his knees. My eyes have also dropped down, and I am staring at his monster cock. He is long and slender, with prominent veins, snaking down his length. It is certainly the longest dick I have seen, outside of porn. The head is just peeking out from its foreskin. I wonder what it would be like to take it in my mouth.

Instead, I stand and take his hands in mine. He then stands close, facing me, still holding my small hands in his large ones. Looking up into his face I say quietly, “Henry, I want you. Will you make love to me?”

He just stands, looking into my eyes for an uncomfortable length of time. Enough time passes that I begin to wonder if there is some kind of problem. Then he says, “I would love to love you, Linda. I’m just not sure if I know how to. Would you teach me?”

Relief washes over me. Does that mean he is still a virgin? Wrapping my arms around him, we embrace and I say into his ear, “Oh silly. We will learn together. I think we mostly just do what comes natural.” He kisses my neck, below my ear, and I feel goose bumps forming, all over my skin. Closing my eyes, I bask in the feeling of his closeness, his unique, pleasant scent. Even his mouth tastes of peppermint.

Pulling back a little, I run my hand up and down and around his chest. I feel his hard muscles, his nipples, the fine hair growing there. I can even feel his heart, pounding hard in lust for me. Gently, I nibble at one of his tiny nipples, and he runs his hands through my hair.

Henry bends down and kisses my upper chest, working his way down to my breasts. The creamy white skin, and the silky soft texture are fascinating to him. He runs his finger lightly around my areola, and they contract and pucker. He takes one of my nipples in his warm mouth, just to feel it there. I feel the tingle down in my groin and deep in my belly. I push my boobs out toward him, wanting more.

Trailing my hands down his abdomen, I get hold of his penis. I have to use both my hands, holding it like a golf club, to cover his length. Squeezing it in my hands, I feel him twitch and he moans.

Opening my legs, I raise one foot onto the edge of my bed. With his cock in my hand, I run it up and down my slit, parting my labia and feeling my slick juices coating him. His dick is rock hard, but the soft tip feels delicious, running up and down my slit and making circles around my clit.

Letting go of him, I say, “I’m ready for you, Henry.” With that I move to my bed, lay down with my legs open and invite him inside.

Bending over me, I am anticipating his entrance. I am ready. Then he asks, “Can I take a look? I would like to understand how you are made.”

“Sure,” I say. I really need him inside me. I hope this doesn’t take long. He traces his finger down the valley between my breasts, to my navel. He stops and plants a lingering kiss, just below my navel. With the back of his fingers, he brushes the hair of my landing strip, up and down. Back and forth. He gently presses down on my pubic bone, testing. His fingers trace the crease, between my outer labia and my thighs, making my pussy tingle. He lightly runs his finger along my inner labia, testing the flesh. I jump as his finger brushes over my engorged clit. He notes my reaction, bends and with his tongue, traces a circle around my clit, without touching it directly. I gasp involuntarily.

“Is that OK?”, He asks.

My voice trembles as I say “Oh yes. That feels fantastic.” He smiles proudly. My labia have opened wide, of their own accord, and I feel him tracing the opening of my vagina with his tongue. The look on his face is pure joy and wonder.

Finally, he completes his inspection planting a kiss on my inner thigh, then asks, “Are you ready?”

I say simply, “Yes.” He moves up my body, laying on me and covering my mouth with kisses. I can taste my pussy on his mouth, which I find erotic. I feel his dick between my legs, so close to the entrance to my vagina. I reach down between us and take him in my hand, guiding him home. He pushes gently, probing. I feel pressure, then stretching as he enters me. I note the involuntary intake of air that I do, whenever a penis penetrates me.

As he enters, he groans and his arms tighten around me. “You are so tight, so smooth, so warm, so exquisite!” He just lays still upon me, holding me tight. I have my arms around him, listening to him breathe, his mouth near my ear.

“Try thrusting,” I coach him. He responds by pumping his hips, sliding his cock in and out. I gasp and whisper in his ear, “Oh Henry. I love you so much!”

He responds in a hoarse whisper, “I love you too, Linda.” The thrusting is so natural, so primal, and Henry begins to increase the pace.

As a cheerleader, I have had my share of sexual partners. When I think about it, I have probably slept with a third of the football team. I am ashamed now, as I think about some of those experiences. I meant nothing to those randy pricks. Just another notch in their bedpost, I suppose. This is far different. This is the way sex was meant to be. No, this is not just sex. This is making love!

Henry begins to moan. It almost sounds more like a growl, and I know he is about to cum. He pulls back just short of pulling out of me, then slams back in all the way. I didn’t think that I could handle all of him, but here it is. I tilt my hips and drive upward to meet his thrust. I feel him twitching inside of me and the hot wetness that I know is his cum. The sensation pushes me over the edge, and a flashing light show explodes in my vision as I plunge down over an endless chasm. I cry out and gasp desperately for air. Awareness dawns that I am digging my nails into Henry’s back, so now I relax my grip and ease up.

It gives me a Thrill, knowing that I have succeeded in seducing Henry, and that I could bring him so much pleasure.

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