The Story of My Life
Chapter 6: Fall 1995 (9th Grade)

Copyright© 2009 by VeX_1138

True Story Sex Story: Chapter 6: Fall 1995 (9th Grade) - This story is a slow starter, but it continues into a regular romp as my teenage years were filled with plenty of sex and many partners. I do mention rape, though as an event in my past and it’s not detailed. This story is true. I have fictionalized some, but much of the story is fact from my point of view. The sex scenes are embellished, but all physical attributes are as real as I remember. If you’re looking for horse dicks and wonder jugs, this isn’t the story, these were real people.

Caution: This True Story Sex Story contains strong sexual content, including mt/ft   mt/Fa   ft/ft   Fa/ft   Mult   Consensual   Romantic   Reluctant   Drunk/Drugged   Lesbian   BiSexual   Heterosexual   True Story   Cheating   Incest   Brother   Sister   Rough   Light Bond   First   Safe Sex   Oral Sex   Anal Sex   Masturbation   Petting   Pregnancy   Cream Pie   Slow  

As I left the darkroom and headed back to class, I'd like to be able to say that I felt like I was walking on air, post-orgasmic and feeling great. But really, all I felt was overwhelming guilt. I'd just cheated on the girl I loved, and I knew it. Even though just two nights ago my girlfriend had brought Michelle into our bed so we could both enjoy having sex with her, fucking Michelle without Rachel's permission today, was cheating.

I wish I could say that was the last time it happened. I wish I could say that I admitted what I'd done and Rachel had been understanding and forgiven me. I wish...

But instead, I kept lying to myself. I met Rachel before Health class and she gave me a loving kiss to greet me. I didn't say a word. I couldn't face the guilt I felt. It was as if speaking about it would only make it true. If I didn't speak of it, maybe it didn't really happen. Maybe I'd only dreamed it. Maybe if I ignored it, everything would go back to the way it was. At least, that's what I kept telling myself.

Instead, only two days later, Michelle slipped me a note as I was coming out of the locker room after Weight Training. She smiled slyly, but scurried away before I could say anything. I opened the note and read:

Nathan,
Find a reason to slip away during lunch. Meet me in the darkroom. I can't wait any longer.
Michelle

After reading the note, I told myself, I wasn't going to go. I didn't need to meet this girl. But the longer my thoughts dwelt on the note and its implications, the more I started to fear what would happen if I didn't go. Would Michelle tell Rachel about what had happened between us? What if not going was what doomed my relationship with Rachel?

In the end, I ended up telling Rachel the first real lie I'd ever told her. I quickly ate lunch and when there was still forty minutes left before I needed to be in Computer Science, I told Rachel I needed to go to the computer lab early. She just nodded and told me she'd see me later. Her trust just made my guilt worse.

When I knocked on the door to the darkroom, the door opened and a hand just pulled me inside. When she flicked on the light, I could see Michelle was completely naked and bathed in the red light from the bulb above us. I couldn't help but grow hard. Though I didn't want to cheat on Rachel, there was no doubt that Michelle was hot.

By now, I'd seen enough of Rachel's bras to know that she had a 34C breast size. Based on that, I'd have to guess that Michelle's breasts were about a 32B. She was smaller and skinnier than Rachel, though not by much, and her breasts were smaller, but just as firm. But the way they were shaped and seemed to just stick out from her chest with no sag to them at all—it made her look so much more youthful than Rachel. Since she was my age and nearly three years younger than Rachel, I guess that makes sense though.

With the door closed and locked behind us, Michelle climbed up onto the counter and pulled her legs up so her whole pussy was exposed to me. She licked her finger and then rubbed it all around her pussy. When she reached the bottom, she continued lower and suddenly I saw she was rubbing a slick circle of her own juices and saliva around her asshole.

"Didn't you promise me you'd take my ass if I got you alone again?" she husked.

My cock was drooling into my shorts, I could feel it. And as much as I wanted to just tell Michelle to fuck off and leave me alone, a part of me really wanted to fuck her. I wanted to punish her for how she was making me feel. I wanted to use her, abuse her, and leave her, just like I had before. And somehow, deep inside, I knew it would make me feel better.

I unzipped my jeans and pushed them down. I stepped out of my jeans and boxer shorts, and stepped up to her, holding my cock out in front of me.

I hadn't really noticed before, but when I glanced at my cock in my hand, I started to think that maybe it had grown a bit in the last few months. It seemed larger, maybe a bit thicker and a bit longer. Not much, but it made me happy to think that this would hurt her just a bit more than it might have a few months ago.

I growled at her, "You fucking cunt. Unless you want to be caught screaming by a teacher with my cock up your ass, you better get down here and lube up my cock with your fucking worthless mouth."

Michelle eagerly dropped down onto the floor and opened her mouth wide. Rather than let her perform, I simply gripped her head, one thumb in each corner of her mouth, fingers curled around the bottom of her jaw. I began to fuck Michelle's face, hard. She didn't struggle, and when my cock hit the back of her throat, she somehow relaxed even more and soon the head of my dick was sliding into the tight confines of her throat with each deep thrust.

Michelle's tongue worked over the underside of my dick, and somehow she managed to use her lips as well, despite the fact that my thumbs were holding open her jaw. She had to be hurting and uncomfortable, but she didn't complain. I grinned when I thought about how her jaw might have bruises tomorrow. I liked the idea that I was leaving marks on her.

I no longer wanted to cum in her mouth, I wanted to make her look and feel like a whore. I pulled out of her face and slapped her across the face, "Get your fucking ass back up on that counter."

Michelle climbed to her feet, working her jaw open and closed. She started climbing back up onto the counter like she was before, pulling her legs up and exposing her pussy and ass to me fully. Her asshole was already red and open more than it had been before. She must have been using her fingers to get ready for my cock. But that didn't make me glad, I wanted her to hurt.

"You fucking bitch! I never said you could use your fingers to get ready for me! I was going to go easy on you. But you've lost that now!" I growled.

I slapped her pussy with my open hand and Michelle gasped. But then she grinned, like I'd just done her a favor. I snarled and put my cock at her asshole. Though I wanted to hurt this girl and take out my emotional turmoil on her, I hadn't wanted to truly hurt her. I wasn't one who normally enjoyed rough sex or sadism, but suddenly I was beginning to realize that I might not be a sadist, but Michelle was definitely a masochist.

With a powerful thrust and persistent pressure, I buried myself in Michelle's super-tight butthole in seconds. Michelle was rocking slightly which both helped me work my way inside her, and seemed to help her with the pain. She exhaled jerkily at the same time, and stared into my eyes. A single tear escaped from her blue orbs and I knew I'd finally pushed her to her limit.

I leaned forward and kissed her tear before it slid from her face. When I pulled back, she leaned forward and captured my mouth with her own. Her tongue pulsed in my mouth and I felt the need in her kiss. When we broke and I opened my eyes, I saw her looking into mine, and I saw it—love. This girl actually loved me ... and I have no idea why.

Confused, engorged, and filled with lust, I couldn't figure out why I saw that look in her eyes, but I'd seen it twice before. Both Natalie and Rachel had looked at me that way. But I've only looked back at Rachel that way.

My cock was buried in her ass, and I wanted to fuck. After a few seconds, I just decided to deal with her feelings later. I started a steady thrusting motion and enjoyed the hot dry friction of her anal tube. Tighter than even her pussy had been, I knew I wasn't going to last much longer. I also knew that this had to be painful for Michelle, but she was gasping in pleasure and smiling at me.

With a few more thrusts, I felt my cock expand inside her and Michelle gasped loudly with a huge grin. And then when her rectum squeezed, my dick exploded—shooting fiery spurts of cum inside her ass. With each hot rope of semen, Michelle twitched and when I looked down at our joining, I could see her pussy was nearly gushing fluids out onto our groins. I was amazed. She was cumming from being fucked in the ass without any stimulation to her pussy and from sex that couldn't have been anything but painful.

When my cock softened a bit, I pulled out of her and without prompting, Michelle eagerly slid down to the floor and lovingly slurped my dirty cock into her mouth. After a few seconds of cleaning, she released me and my cock fell limply in front of me. Michelle looked up at me, her eyes gleaming with delight. I pulled my pants and boxers up and put myself back in order.

Instead of leaving her behind like I had last time, I leaned against the door and stood watching as she got dressed. She bent over, facing away from me, and stepped into her panties. When she was fully bent over, a long line of my cum was starkly glowing in the red light. It had leaked from her gaping asshole and was running down her leg. I couldn't help but grin. Michelle pulled up her panties and somehow the line of cum remained untouched.

Then she pulled on her bra, then her skirt, and finally a bright-red t-shirt that had a white heart on it, naturally drawing the eye to her breasts. The t-shirt was tight and her bra-encased breasts looked even better once the t-shirt was wrapped around them. When she bent over to tie her shoes again, I saw the line of cum was still there. I grinned, but I knew that I couldn't let her leave like that.

"Uh. You might want to get a paper towel. I'm running down your leg," I warned her with a teasing grin.

Without standing back up, Michelle's eyes met mine and they twinkled, "I know. I kind of like it there. I just know the rest of your load is going to be leaking out into my panties for the rest of the day. I'll be soaked."

When she stood back up, she leaned towards me like she was going to kiss me, but then she turned at the last second and pecked me on the cheek. Her voice husked into my ear, "Sorry, I can't give you a proper thank you kiss right now—I've got whore breath. If you want a ride home from school after practice tonight, just slip a note in my locker and tell your sisters and girlfriend you're riding home with a friend from the team. I'd love to have you fuck me again and fill me up with your cum later so it's leaking out of me when I eat dinner with my parents tonight."

I was stunned, shocked, and my cock was painfully hard again. I didn't know what to say. Instead, Michelle just flicked off the light, opened the door, and skipped out like I hadn't just taken her cherry ass for its first ride. Who the fuck is this girl!?


I didn't leave her a note that afternoon, but I can't honestly say that was the last time I fucked the blonde nymphomaniac. Two days later, she passed me another note and I met her in the darkroom again. Sex between us was passionate, fairly rough, and athletic. Michelle seemed to wear the bruises, smeared cum, and make-up smudges like they were badges of honor.

That weekend, after another football win, I found myself at yet another party, making love to Rachel and then ordering Michelle to suck my cum out of her. Rachel had brought her into our little celebration ritual again. This time, Michelle had kept her cheerleading uniform on and I'd enjoyed making her keep it on while I fucked her, spanking her while I pounded away in her asshole.

For the most part, things continued like this for months. I dated the girl I loved; I fucked the blonde cheerleader on the side; regular threesomes were arranged by my girlfriend at weekend parties, always involving Michelle as our 'third'; and I continually felt like my guts were being slowly eaten by tiny creatures inside me.

About the only sexual relationship I had during this time that didn't fill me with guilt was the irregularly occurring masturbation and porn-watching sessions I had with my lesbian stepsister, Alice. Luckily, we'd also talked a bit about these 'late-night encounters.' Alice told me she wasn't completely sold on being a lesbian, but that she'd never been past second base with a guy. "Girls are sexier, easier to understand, and much safer," she said.

I had to agree with her. Guys are assholes, just like me.

In the grand scheme of things, I should have just been enjoying the fact that I was getting laid on a regular basis by two beautiful girls, but I was torn up inside.

Things continued like this, all through the fall. I was so messed up by October that I nearly forgot Rachel's birthday and had to hustle to plan something for her. Honestly, it really wasn't a memorable event. I took her out for dinner and told her I'd paid and arranged for a photographer in Boise to start a modeling portfolio for her. She was ecstatic about the gift.

By Christmas, Rachel had a portfolio full of absolutely gorgeous pictures and had already started feeling out the local and regional modeling agencies to see what they had to offer. Once they saw her portfolio, all of them made an offer to sign her. Rachel was excited, but was still weighing her options.

My 'affair' with Michelle had even grown more serious. I'd actually agreed to go out with her a few times after school on days when Rachel couldn't give me a ride home. I refused to actually go out in public with her, afraid someone would see us, but we did find places to have sex. The sex was great, amazing even, but it also came with a price—every time I fucked Michelle, a piece of my soul felt like it was disintegrating.

Oddly enough, it wasn't until Christmas that the person I shared my soul with began to notice the missing pieces and the pain I was in. But as glad as I was that Natalie seemed to notice something was wrong, I knew it would kill her to lose Rachel. She would hate me if I told her the truth.

In the past few months, Rachel and Natalie had become closer and closer friends. If I told her about Michelle, I'd not only explain my current pain, but I'd end up transferring a lot of that pain into her. See, she'd stick with me and stay the supporting best friend, but I'd hurt her deeply in the process. She'd probably find a way to give me the strength to break up with Rachel and Michelle before I hurt them both, but it would also rip out my heart and send me down a dark path that went to a place I couldn't predict.

So, when Natalie asked me what was bothering me a few days before Christmas, my exhale alone spoke volumes.

"Listen, I know you fucked up. You did something bad and it's eating you up. I can tell, so why don't you just tell me so I can help you," Natalie said.

We were alone, watching a movie that both of us had seen a few hundred times before. And though I had a thousand reasons not to tell Natalie, I suddenly didn't care—I wanted to tell her—everything. I knew that it was only self-serving to emotionally unload on her, but she was offering, and I suddenly didn't have the will to care about the consequences any more. I just wanted the pain to end.

With another large sigh, I said, "You're going to hate me." It was a final warning. She may have offered, but I at least owed her this warning.

"I might be disappointed in you, I might get angry, but I could never hate you," Natalie assured me.

"Alright. It all started before the season opener against Caldwell. I came out of the locker room and there was Rachel, waiting for me, but she was talking to Tommy Fitzgerald." Over the course of the season, Tommy and I had kept our distance, but we'd actually made our peace with each other.

"Oh," Natalie nodded.

"Yeah, and then after the game we went to a party. When I came back to her after getting a new drink, there they were together again, laughing this time. I just snapped. I was so angry with her."

"But not him?" Natalie asked.

"No. I ... I didn't blame him. Rachel is amazing and I can't blame anyone for being attracted to her. But I was so angry with her. So I ended up alone and getting drunk.

"Rachel eventually apologized, and she has stayed away from Tommy ever since because she knows it makes me jealous. Just another reason to feel guilty really. But that night, she wanted to have some fun, to celebrate my performance in the game, so she invited another girl to join us for another threesome."

"Who?" Natalie asked.

"Michelle Edwards."

"Fuck!"

"What?" I asked.

"I don't know how you've managed to have sex with both the hottest senior and the hottest freshman, all in the same year," Natalie joked.

I didn't really feel like joking though. This was serious. I just decided to ignore her, "During the sex with Michelle, I suddenly started to feel better, like I was taking out my anger on her. And oddly enough, she seemed to enjoy it.

"This probably would have been fine, but then Michelle got me into a room alone at school a few days later. We ended up fucking again, alone. So then I was filled with guilt for cheating on Rachel, and then I even started to resent her because if she hadn't been talking to Tommy in the first place ... I wouldn't have felt jealous and the sex with Michelle would have just been emotionless sex, or maybe Rachel wouldn't have even brought her upstairs to sleep with us.

"And since then, I've been fucking Michelle just to get a moment in my day when I don't feel like the sky is falling down on me. I've thought about telling her I want to stop, but I keep thinking that she'll screw things up with Rachel if I do. And it doesn't help that Rachel is oblivious and keeps arranging threesomes with her. I just don't know what to do. I know the right thing to do would be to break up with both of them, and just wallow in my own misery. There are two things holding me back from doing just that. One, I'd be miserable. Two, I know I'd hurt Rachel.

 
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