This is a work of fiction. None of the characters are real. No baby animals were clubbed in the making of this story. It was written out in one day and proof read that same day, so please excuse any mistakes or inconsistencies. I realize it’s a bit longer than most of the stories I see on here, so I apologize if it gets a bit boring, you can always skip ahead to the good bits. I hope you enjoy it. Be gentle, it's my first time posting here.
I’m writing this as a confession. Kind of. My name is Katie. When I was sixteen I broke up with my first oh-so-serious boyfriend Tom. It was dramatic, though at that age I think all breakups are. Tom and I had been dating for a year. (I know, a whole year.) Things had been going pretty well up until we hit a brick wall called prom. I’ll get to what happened there later, but I should point out that I’m not confessing about a breakup.
After the break up I had a fling. You know, the night of passion you have to get back on your feet and remind yourself that, yes, you can actually go on living without the boy you’ve been mooning over. So I had a fling, big whoop, right? Most people have at least one of them. But this is where things get strange. My fling was my little brother Shawn. There, I said it. You can hate me if you want, but at least hear me out so you can hate me for the right reasons.
Let’s get one thing straight: I didn’t set out after my brother. It wasn’t like that. I really didn’t look at him that way. There were a lot of things that made what happened… happen. But looking back on it now I think there was one moment that set things in motion. It’d happened one night a month or two into my relationship with Tom.
Shawn and I had a tradition of sorts. Every Friday night we’d watch a movie. If we didn’t have other plans, that is. In theory either of us could choose a movie, but being the oldest, I usually pulled rank and made him watch whatever I chose. This particular night I’d chosen Jurassic Park. What can I say? I like raptors. Anyone will tell you that Jurassic Park is a classic, and if they don’t then they’re full of it. My brother Shawn was full of it.
“The raptors are so lame! I mean how can a dinosaur open a door? Mittens can’t even open a door and you expect me believe they can? Pft, like I said, lame. Lazy writers,” Shawn said with unbearable smugness.
“You take that back!” I shrieked. “Scientists think they were pack hunters. That takes some degree of intelligence. And our cat is an idiot. Case closed.”
“Fine, even if the raptors were legit, what about the awful robots? I mean, come on, I think I’ve seen better stuff on Sesame Street in the last few years,” He said, and crossed his arms.
“You…” I could only scowl at him. I could have explained that the set and props on the movie were cutting edge for their time, but that would have legitimized his arguments. As if! The only appropriate response I had to this was to tickle his unsophisticated critique into oblivion. At thirteen Shawn was still a bit smaller than I was.
I stood about 5’6” on a good day, and Shawn was an inch or so below me the last time I’d checked, though he’d been going through some serious growth spurts in the last year, I wasn’t likely to continue my reign as tallest sibling for long. I was also stronger than he was. I dove at him from across the couch and aimed my hands straight for his sides.
It was his kryptonite. He was the most ticklish person I’d ever met. He squirmed and gasped and giggled. With flailing legs he tried to lever himself out from under me, but I held on. We both tumbled over the edge of the couch. I landed on top of him. That’s when it happened.
As was typical for a movie night, I was wearing sweatpants and a t-shirt. When I’d landed on top of him I’d ended up vaguely straddling his hips, not in an intentional way, but our hips were aligned nonetheless. He was wearing some loose plaid shorts. My sweat pants and those shorts were the only things separating his throbbing, yes I felt it throbbing, erection and my own naughty bits. What the hell? I mean I was his sister. That was pretty messed up, right?
This all happened in the span of maybe a second or two. In the same instant that I felt his erection pressing against me, he tucked his hips and pulled it away. I looked up to see that his face was beet red. My outrage dwindled at that. Ok, maybe I was being too judgmental. I mean he was a thirteen year old boy, which meant he was three parts penis and one part brain. And I was, to toot my own horn, a fairly attractive and sophisticated young lady. Maybe I should let it go and just take it as a compliment.
“Sorry, buddy, the boner maneuver isn’t going to save you,” I said, and finished tickling him into oblivion, my hips a safe distance away this time. Afterward we finished watching the movie and didn’t speak about it anymore. He was a little awkward immediately afterward, and rightfully so. But by the end he’d gotten back to his smart ass self and expounded on his dislike of rubber baby dinosaurs in the hatchery scene.
Obviously nothing untoward happened that night, that’s not why I brought it up. I was still seeing my boyfriend Tom. The point is that the night made me aware that underneath the label of brother, Shawn was sexual creature, even if I found the notion mildly nauseating at the time. More specifically, he was a sexual creature that evidently found me attractive, if the erection was anything to go by.
Tom and I never really had a chance, when I think back on it. But hindsight really is 20/20, isn’t it? We all lie to ourselves at the time. We’d met at school, of course. First period was a study hall. At my school we had four classes a day, each about ninety minutes long, but they only lasted for half a school year. So that meant that I had the first hour and half of every day to do as I pleased.
Study hall was a bit of a misnomer. So long as you had at least a B average studying wasn’t mandatory. You could go to the library, the cafeteria, or, if you were clever, you could sneak into the auditorium. I was all sorts of clever. One day I was hanging out in the auditorium with my friend Jane. Later on in the day you’d have to worry about dodging the theater groups, but in the morning it was open.
There really wasn’t anything good about hanging out there over the cafeteria or library, except that you weren’t supposed to be there. The seats were pretty comfortable though. That day Jane and I were sitting in the back row, listening to music, and generally enjoying having nothing to do.
We weren’t the only clever students, though. A group of boys were milling about the first two rows of seats. The boys were being just loud enough that I was starting to worry that they’d get us all kicked out. Getting caught by a teacher and punished was the last thing I wanted to start the school day with, but I tried to ignore them, they couldn’t be that stupid right? Boys. They only got worse.
Eventually I’d had it, I wasn’t going to get caught because of them and I was not going to leave. We’d gotten there first, after all. I took off my headphones and stood up.
“Hey! Where are you going?” Jane asked.
“To shut those idiots up,” I replied.
“Maybe we should just go,” she suggested. She didn’t like conflict, but that was okay, she didn’t have to get involved.
“Don’t worry about it, I’ll handle this, you just sit there, I’ll be right back.” I started climbing down the steps before she could try and talk me out of it. The boys didn’t look up at me until I was almost down to the front row. They quieted down and just looked at me. I glared back.
“What do you want?” Asked one of the boys in the middle of the group. This was, unbeknownst to me at the time, Tom.
“I want you jerks to shut up, you’re going to get us all caught,” I said, maintaining my glare.
“Yeah, okay, mom,” one of the boys said, I didn’t catch who.
“Hey, shut it,” Tom said, punching, presumably, the heckler in the arm. He turned back to me. “Alright, we’ll quiet down, on one condition, though.”
“You give me your number.” And I did. I was sorely tempted to just make a number up, Tom had some nerve. But despite myself I was intrigued by him. He had light blue eyes and dark hair. He also had a wispy, teen mustache, but I could forgive him that. That very night he called me for the first time and we set up a date for the weekend.
The date consisted of dinner and a movie. Totally cliché, right? But what else can you do? Between curfew and money high school dates were what they were. The dinner portion took place at Portillos. It’s a regional Italian beef and burger joint. We were sitting in a booth underneath a neon sign and all sorts of old movie memorabilia. Yeah, it’s that kind of place.
“Oooh, so you’re a big bad junior,” I said.
“Watch it, sophie, I might pull rank and get you shoved in a locker,” Tom said with a wink.
“Yeah right, that only happens to freshman, and you’re not that big of deal, talk to me next year when you’re a senior. Or maybe the year after that when you’re a super senior,” I haughtily turned my face away from him.
“Ouch, you got a band-aid? I think that one left a mark.” As we talked I learned a lot about him. He’d moved into the area a couple years ago, so he was still kind of new, he didn’t have the life-long childhood alliances that natives like me had. Jane? I’d known her since first grade. I didn’t feel too badly for him though, Tom had clearly demonstrated that he could put himself out there.
He glanced down at his phone, “Woah, hey, we’ve got to get going if we’re going to catch the movie.” We tossed our garbage on the way out and got into Tom’s car. I still couldn’t help being impressed by the car, as a fifteen year old I could only stare in jealously. There were advantages to dating a junior, I had to say.
The movie was terrible. It was a spoof movie that was supposed to riff on how terrible all the other movies in the genre were, but it mostly managed to just be terrible in its own right. When I felt Tom lean over and lightly kiss my neck I was almost relieved, it was a welcome distraction. That light kiss was followed by a firm kiss. I turned to face him and our lips met. His tongue met mine and before I knew it we were deeply involved in a make out session. Luckily we’d sat near the back of the theater where it was dark and somewhat secluded.
Had he planned this? I wondered, but I wasn’t going to complain. He nipped my bottom lip lightly and ran his fingers along my forearm. I got goose bumps.
“Your lips are so soft,” He murmured quietly.
“Your mustache is a little itchy,” I said in a mock-sweet tone, instantly regretting it even as the words left my mouth. Foot, meet mouth. Mood killer in the house.
“You really are a smartass,” he said, and kissed me before I could make any attempt at a lame apology. I felt his hand run further up my arm and then cup my breast over my shirt. Wow, he really was forward. I’d already lifted a hand to push his arm away, but decided against it. What was the harm in a little shirt boob?
I gasped as I felt him lightly tweak my nipple through my shirt and bra. Wow again, he knew what he was doing. I put a hand on the back of his neck and pulled him closer, my kisses grew more urgent. He gripped my breast more firmly and wrapped his free arm around me. He took my hand, but I didn’t pay much attention, being deeply involved as I was in kissing. That is until I felt him rest it on something warm and soft. I broke off the kiss and looked down.
When I said he put himself out there… I hadn’t meant it quite that way. What I saw was his cock sticking out of his unzipped jeans. My hand still rested on it, the fingers curving, though not actually gripping the shaft. It was a good size cock too. My thumb and index finger might have reached around it, but just barely. And he was uncircumcised, that was new for me. I could feel a bit of sticky pre cum on my palm that had streamed down from the head.
Dammit. I was fine with a little over the clothes heavy petting. Maybe it was a bit much for a first date, but he was cute and I was horny. But a hand job? Really? Who did he think he was? For that matter who did he think I was? I had messed around with boys before, and I’d definitely given a hand job before, even a blow job, but not on the first date. I pulled my hand off his cock and watched as a string of precum stretched and broke off.
“What’s wrong?” He whispered to me.
“What do you think is wrong?” I hissed. “Pulling out your cock on the first date? Do you really think I’m that easy?”
“What? No! I’m not thinking that at all. We just really seemed to be getting into it and… well… sorry,” He finished lamely.
I reached down and gripped his cock, maybe a little too tightly. More precum bubbled up. “Listen, I’m not a prude, but what we do and when we do it, are my call.” I pushed his cock back into his jeans. I zipped him up too, just for good measure.
He groaned slightly at my touch. “Yeah, sure, I get it,” he said. But I don’t think he did.
“You mean he pulled it out?” Jane asked me in an overly-hushed voice.
“Yes, it. His cock, grow up, Jane,” I said, rolling my eyes.
“Shhhh, don’t say that in here, someone could hear!” We were sitting by ourselves at a table in the cafeteria. I really don’t think anyone was going to hear us, but whatever.
“Fine, fine. But can you believe it? I mean I’m not a prude, but god, he wanted a hand job on the first date! I usually make the guy wait at least three dates.” Jane bit her lip and didn’t say anything. “What’s wrong with you?” I asked.
“I’ve… never, well, you know,” she said, looking at the ground.
“Seriously? What about Peter? You guys went out for like four months!” I exclaimed. I mean everyone is welcome to their own pace and comfort level, far be it from me to judge. But boys these days, well they have the internet, they can compare notes. It’s kind of hard to be prude and go steady. Maybe if you met at a church group it'd work, I guess.
“Yeah, so? I mean we kissed, and I… uh… felt it a little…” She added suddenly, “Over his pants, I mean!” She clapped her hands over her mouth as she’d said the last a little more loudly than she’d meant to. I looked around, but I didn’t see anyone staring. She’d rubbed a steady boyfriend’s cock through his jeans, big whoop. I didn’t say this, of course, she was my friend, and who was I to say anything? I was complaining about Tom being too forward, I couldn’t very well tell Jane she was holding back too much.
“So… uh, are you going to see him again?” Jane asked.
“Well, yeah, I mean it was just a hand job – no offense! – we’re supposed to go out again tomorrow night.”
“Are you going to… you know?” She moved her hand suggestively and then stopped and looked around in case someone was staring.
“I… um… I guess we’ll see,” I said.
“Really? But I thought you said you make them wait for three dates, this would only be two.”
“I said we’ll see, okay?”
It didn’t take long for me to reach that crossroads. We’d gone out to another movie, and it seemed Tom was working off of the same script because once again I found myself being pawed at in the back seat of the movie theater. He hadn’t even waiting for the movie to start this time. As soon as the lights went down he was all over me.
Ten minutes of kissing, nibbling, and fondling later I found myself with my hand on his thick, uncircumcised cock once again. I bit my lip. My rule had been three dates, but I guess two wasn’t that bad, right? And it definitely was not the first date. I closed my fingers around his cock. He kissed me harder. I jerked his cock up and down once, slowly. I watched as his foreskin slid down, exposing the glistening head of his cock.
I leaned my head to the side and kissed his neck. I felt his cock pulse hard as I nibbled on his earlobe. Each stroke of his cock made a faint sucking sound as the precum made his foreskin sticky and slippery. I stroked harder and faster as I felt him writhe a little. His breathing was growing ragged.
I thought I saw someone a few rows ahead look back at us. Had they heard me jerking him off? Woops. Time to cool it down for a minute. I reached down and pulled his balls out of his pants as well. I felt his scrotum tighten at my touch. I fondled his balls and kissed his neck while I worked up the nerve to start again. I still had a thing or two to learn about foreskin, I guessed. I didn’t want to get caught jerking a guy off at the movies, that’d be one hell of an uncomfortable conversation to have with my parents.
I felt a thick stream of precum drip over my hand as I fondled his balls. Wow, he was really turned on. I finally wrapped my hand around his cock again and starting stroking it. My precum-slick hand glided over the shaft. I gripped it lightly and ran a thumb along the slippery foreskin under the head of his cock. This must have sent him over the edge because he shifted and his cock tensed. Before I knew it a spurt of hot cum covered my hand. I went back to jerking his cock instead and the next spurt of cum shot out hard enough to hit the back of the seat in front of us. I kept jerking until the cum finally stopped flowing, though it took two more spurts. These landed on the floor.
He lay back in the chair and breathed deeply. “Man,” he said, “You’re good.”
That second date had set the tone for most of our relationship. He was the older, more experienced boyfriend. I was the young girlfriend who was constantly giving in and trying to catch up. I’m not telling you this so you’ll feel sorry for me or forgive me. I’m just trying to explain my state of mind. Trust me, things didn’t slow down over the year that we dated.
Tom knew what he wanted and he was relentless in his pursuit of it. Whenever he got it, that became the new minimum. I don’t think I’d ever given a guy so many handjobs before. Every date included him getting off at least once, he made sure of it. I think he must have been telling the truth when he said I was good, because he was content with handjobs for a long time. But he was ambitious…
Tom, Jane and I were sitting in the auditorium one day during study hall. Tom and I had been dating for just over four months at this point. I’d given him so many hand jobs I was afraid I was going to get carpal tunnel syndrome.
“I still can’t believe Mr. Smith wants ten pages for our history report! I know it’s double-spaced, but what a hard ass,” Tom said. Mr. Smith was our world history teacher. We didn’t actually have the class together, but it was the same regardless of what period you took the class. Even though he was a year ahead of Jane and me, he was taking the same class. You didn’t have to take it any specific year, just some time before you graduated.
“Ye—Yeah, that’s a lot,” Jane said quietly. She was usually this way around Tom. Quiet, awkward, and short with answers. I blamed myself. She and I had discussed Tom’s… assets in detail. She knew roughly how big he was – I’d had her put her fingers around my wrist to give her a general idea, granted I petite wrists. And I’d described what it was like to see and touch an uncircumcised cock. She hadn’t been able to look Tom straight in the face after that. Luckily Tom didn’t seem to notice or care.
“I’ll say! It’s going to take me all weekend to finish this paper, speaking of which,” He turned to me. “Sorry, Katie, I think I’m going to have to cancel our date for Saturday.” This was news to me.
“What? Tom, you had three weeks to write this paper! What have you been doing this whole time?”
“Well s-o-r-r-r-y, someone, who shall remain nameless, has kept me too busy and tired to concentrate on much else,” Tom said and winked at Jane who blushed deeply.
“You pig!” I smacked his arm.
“Before I forget, come with me for a minute,” he stood up and grabbed my arm.
“What?” I asked.
“Just come on, I found something cool backstage,” He said.
I looked at Jane who shrugged and buried her face in her math book. I gave up. “Fine,” I said. “Show me whatever stupid thing it is you’ve found.”
He led me down the stairs and onto the stage. We ducked behind the curtain and were surrounded by background scenery, costumes, props, etc. Tom raced ahead and stood in front of a box of props with his back to me.
I stood a few feet away and crossed my arms. “Well, what is it?” I asked. He turned around and I gawped. His fully erect cock was hanging out and he’d tied a little bow around it.
“I told you you’d want to see it,” he said with a grin.
“Tom! Put it away, we can’t do that at school!” I said, scandalized.
He took a step toward me. “Hey, relax, babe. We come in here every day, when’s the last time we saw a teacher come in?” he asked. “Never,” he answered before I could open my mouth. “And I wasn’t joking back there, I really do have to finish my paper this weekend. So I can’t see you like we’d planned. I figured maybe we could fool around a little here instead. He closed in on me, his cock pressing against my stomach through my shirt. “What do you say?”
Then he had his arms around me and my mouth was too full of his tongue to protest. I was wearing a tight’ish t-shirt and the shirt had a tendency to ride up a bit, exposing some midriff. His cock rubbed against the exposed section of my stomach, smearing it slightly with precum. He pressed harder against me. His cock slid down as he pushed forward and it managed to get under the waist of my jeans. The head of his cock was resting against my panties, just above my clit. Despite myself I could feel my pussy grow wet.
He leaned in and said with a grin, “Hey, I got in your pants.”
I reached down and pulled his cock back out. “Not today, buddy.”
He held up his hands. “Hey, only kidding, boss lady.” His joking always had a serious edge to it. There was no way I was letting him jump from hand jobs to sex. I had some experience sure… but I was still a virgin. Sex wasn’t a huge deal for me in theory. I wasn’t waiting for marriage or anything crazy like that. But I wasn’t sure I wanted him to be my first. We got along fine when we weren’t messing around… but a lot of our time together was messing around.
He sat down on a closed prop box, his cock still jutting out. “Come here, babe.” I gave in and stepped forward. I felt his grip on my shoulders and he pulled me forward for a deep kiss. He subtly angled me down so that at the end of the kiss I was kneeling in front of him. Another hand job it was. And in school this time. I’d gotten so used to the routine that I just went with it. I leaned down and wrapped a hand around his cock, after discarding the ridiculous little bow.
He leaned forward and ran a hand through my hair. I stroked his shaft and ran a hand over his flat stomach. I’d figured out he liked this over the last few months of practice. He ran his hand down my back and grabbed my ass firmly. I jumped a little -- that was new. He kissed me and slipped his hand under my jeans and panties to grip my bare ass instead. I kissed back and let him grope me. He leaned forward more and pulled back on my ass, forcing me toward him. I finally realized what he was trying for. The head of his cock was no more than six inches from my face.
And then he surprised me more. He ran his hand along to the front of my panties and rubbed my clit between his middle and index fingers. I gasped. He used his free hand to grip his cock and rub the head of it against my lips. I licked his cock. He groaned and redoubled his efforts, working my clit back and forth. I ran my tongue around the head of his cock inside his foreskin. I’d never done this with an uncircumcised cock before, but he seemed to like that.
I locked my lips with his foreskin and slid the head of his cock in my mouth, teasing it with the tip of my tongue. He slipped a finger into my wet pussy. I stopped licking for a moment as I shuddered. He began stroking his exposed shaft. I tasted the salty tang of precum as it oozed from his cock. Tom moved back on the box slightly, pulling his cock out of my mouth. He pulled his pants down more so his balls were exposed and then started jerking his cock in front of me.
I leaned forward and ran my tongue down his shaft and over his balls. It was odd. I could feel them move as my tongue pushed against them. I’d given blowjobs before, but I’d never done this. He worked another finger into my pussy and began sliding them in and out of me. My pussy quivered slightly. I sucked one of his balls into my mouth.
“Oh yeah, Katie, just like that,” he moaned. I caressed it with my tongue and sucked a little harder. He’d started jerking his cock a little erratically. My pussy chose that moment to tighten around his fingers. I moaned and let his ball fall out of my mouth as I shuddered through an orgasm with my eyes tightly closed. He’d already pulled his fingers out of me and I felt him push me back slightly as he stood up. I opened my eyes and he was standing in front of me, stroking his cock.
He pressed his cock against my lips hard, I opened my mouth and he pushed his cock inside as deep as it would go. I fought against gagging for a moment before he finally let up and slid his cock back out. He jerked his cock very quickly now, I saw it glisten with my spit.
“Oh, Katie, here it comes,” he moaned. That was all the warning I had. He let it rip. The first spurt hit my cheek and dribbled down my face and onto my shirt. I leaned forward and opened my mouth, I almost caught the second spurt. It hit my lips and rebounded slightly, some of it splashing into my mouth, the rest running down my chin. I wrapped my lips around the head and swallowed the next two or three spurts as he jerked them into my mouth.
He sat back down and sighed. “Good hands and an even better mouth, I bet your pussy is fucking amazing.”
I wiped some of the cum off my face with my hand. He’d just done things to me that I’d never done before and now he was talking about fucking me? I wasn’t sure how I felt… part of me was a little pissed off.
The cancelled date meant I had time to do something that I hadn’t done for a while, and that was watching a movie with Shawn. It’d been a couple months since what I’d come to think of as “the boner incident”. Neither of us talked about it and that seemed to suit us just fine. It’d just embarrass Shawn, after all. As much as I liked to tease him, I figured I’d let it slide.
We were watching the Matrix today. I’d let Shawn choose. After giving Tom a blowjob at school and hearing him pronounce how excellent he anticipated my pussy being, I was understandably a little preoccupied. So I hadn’t chosen the movie. It was okay, even though I thought Keanu Reeves had all the acting talent of an angry two-by-four, it was still a pretty good movie.
“So how’s T-o-o-m-m-m doing?” Shawn asked while making a kissy face and hugging himself.
“Oh shut up, dweeb. He’s fine.”
“Katie and Tom sitting in a tree, K - I - S - S–” I whacked him in the face with a pillow to shut him up. “Alright, alright. But let me know when I’m going to be an uncle, I’d like time to get ready.”
“Ah, I understand now. Mom and dad probably should have had this talk with you, but here it goes. You see when a man and a woman—”
“Hey! I know about sex”, Shawn protested.
“Really? Then you should know you actually have to have sex to get pregnant, dork,” I said.
“Eww, okay, way more information than I needed to know,” Shawn said, putting his hands up between us.
“You’d like it better if I were having sex then?” I asked, arching an eyebrow.
“God no, never mind, you win,” he said.
We sat watching the Matrix for a while. Keanu took the red pill. I wondered if it tasted like cinnamon.
“Hey, Katie?” Shawn asked, jarring me from my thoughts.
“Are you okay? You’ve been… quiet.”
“Well, normally you’d have been busy making fun of Keanu, and me, and you haven’t done any of that. You’ve just been sitting there scowling,” he said.
“Yeah… it’s just… Tom,” I said, not sure exactly how I could explain things to my brother.
“What about him?”
“Nothing… really, things have just been… hectic. I’m fine, I promise.”
“Alright, if you say so, but remember, I am your brother, I’m here if you need me.” I felt myself tear up a little bit. The last thing I’d expected was for him to be protective or worried about me.
“That’s very sweet, I’ll remember that, thank you.” I wrapped me arms around him and hugged him tightly.
“Yeah, just let me know if you need me to kick Tom’s ass,” Shawn said and flexed dramatically.
“Like you could, dork.” I pushed him back on the couch.
We finished watching the movie. I made a mental note that I needed to make sure that our movie nights didn’t keep taking a back seat to my dates. Shawn really was a sweet kid and Tom shouldn’t always be more important. Boyfriends are for a while, but brothers are forever.
Over the next few months I made sure to have plenty of movie nights with Shawn and I felt like we were back to being as close as we’d ever been. I also had plenty more dates with Tom. That night we were in his car. He’d driven us over to a secluded hill. It was a great place to watch the sun set. It was also a great place for him to start pawing at me.
He pulled my shirt over my head and kissed at my neck. I reached down and fondled his cock through his jeans. I felt him undo the catches on my bra strap. Even I couldn’t unhook the damned thing that fast. He pulled away from me just long enough to remove my bra and then pulled me back toward him, one hand fondling my right breast. I took off his shirt and sucked on his neck. I grinned as I felt his cock spasm through his pants.
Tom fumbled at his pants and kicked them off. He was now stark naked sitting beside me in the backseat of his car. I leaned over his lap, taking extra time to let my breasts rub against his cock. I’d picked up some new tricks. Really I was concerned about keeping him happy and delaying the inevitable question of whether I actually wanted to sleep with him.
As if on cue Tom started fumbling at the button on my jeans. I pulled away. “Tom…” I started.
“Hey, don’t worry, it’s not what you think,” he said. I reluctantly leaned back in and let him unbutton my pants. While he was busy with that I wrapped my lips around his cock. For a few minutes he forgot all about my pants. I ran my tongue under his foreskin and fondled his balls. My hand moved up from his balls to his cock and jerked him hard and fast while flicking my tongue beneath the head of his cock.
He moaned and writhed, but eventually got back to working my pants off. Finally I was sitting as naked as he was. He lay down on the back seat and I eyed him warily.
“Calm down, babe. Lay down with me,” he said.
“Tom…” I started again
“Not like that,” he said. He gentle pushed me in the opposite direction and pulled me on top of him so that his cock was right in my face. I opened my mouth and sucked him in from this new and unfamiliar angle.
I shuddered when I felt his warm tongue suddenly caress my pussy lips. I grabbed his cock and stroked it while sucking on the head. His tongue probed my pussy. I moved my hips a little bit, encouraging his tongue further inside. He pushed his tongue as deep as it would go. I moaned and shuddered. He worked my clit with his fingers while tongue-fucking me. I shuddered and bucked my hips as his tongue brought me to a full blown orgasm.
I held on tightly to his cock as I writhed in pleasure, it ended up nestled between my breasts. They were only C cups, but that was good enough to mostly conceal his cock between them. He started thrusting his hips. I realized he was actually fucking my breasts. I let go of his cock and used my hand to squeeze my breasts together. He moaned and thrust harder. I felt his cock grow stiff and then the first spurt of cum shot out and landed on my shoulder. I held my breasts together as best I could while he fucked them. The second spurt reached my shoulder blade. I let my breasts go and wrapped my lips around his cock, milking every last drop of cum.
“Holy shit,” he breathed afterward. “That was amazing.”
“Yeah, it was,” I agreed. Satisfied and relieved, I turned around and snuggled up next to him. We sat that way just enjoying each other’s company for another five minutes or so until I felt his cock start to stiffen again against my ass. I reached down to the floor of the car and found my jeans. I pulled my phone out and checked the time. Saved by the clock. “Hey, I’ve got to get home, we’d better get dressed.”
Months passed. My birthday came and went, Shawn's did too. They were only two months apart. Prom was now only a month away. Yeah, that prom. The brick wall. Though I didn’t know it at the time. It was Friday night. Shawn was staying over at a friend’s house and I was sitting at home reading my history book. We’d been assigned a whole chapter that had to be read and ready for discussion by Monday. I felt my leg vibrate. I pulled my phone out of my pocket. It was Tom.
“Hey,” I said in the perky girlfriend voice.
“Hey, baby,” he said. “I’ve got a quick question…”
“Are you on the pill?” he asked.
“Wow… uhm, no… why?” I asked, somewhat shocked by his frankness.
“Well, just trying to figure out if I should pick up some condoms, for, you know.”
“No, I don’t know, for what?” I asked, a little angry.
“For prom, duh.”
“Woah, who said we were having sex after prom?” I asked.
“The entire history of prom? It’s what you do. Come on, we’ve been dating for almost a whole year now! Don’t you like me?”
“Yeah… I like you, but I’m not… You remember when I said I get to decide what we do and when? Well we’ve done a lot… but just not this, not yet.”
“Seriously, Katie, grow up.” Click. He fucking hung up on me? That asshole! He could go to the prom by himself as far as I was concerned.
He called me again the next day.
“What do you want?” I said by way of greeting.
“Woah, calm down. Listen, I’m sorry about last night…” he said.
“Sorry isn’t good enough. You were an asshole, that was not okay,” I said.
“I know, look there’s no excuse. I’m just frustrated. I really like you and I want to be with you. All my friends that haven’t already gone all the way are doing it after prom. It’s kind of a tradition. I just thought, you know, we’d be able to do the same. And when you said you didn’t want to… I don’t know, I got upset.”
At least he was being honest about it… Part of me wanted to just hang up on him right there and then. But we’d been together for a while, and I did like him and we were supposed to go to prom. I’d already bought the dress and It’d be hard to find another senior that wanted to take me on short notice, and he had apologized. I decided to give him a second chance.
“So you’re okay with us not having sex on prom night?” I asked.
“Absolutely. I’ll wait as long as it takes. And in the mean time we can still have fun, and dance during prom,” he said.
“Okay…” I said. “But you better never hang up on me again, jerk.” And just like that, prom was back on. Man I wish I’d hung up instead.
Our prom took place in our school auditorium. This isn’t as corny as it sounds. The school had shelled out a lot of money over the years to turn our auditorium into something state of the art. And it was big. It was actually its own building on our campus. The school would sometimes rent it out for private events to bring in more money.
Prom night, it’s so much different than you think it’s going to be. I’d watched plenty of movies. You think it’s going to be a bunch of teenagers dressed up in fancy clothes, dancing sophisticated dances and sharing a magical evening to beautiful music. In truth you’re likely to get one out of three of those. People did show up in fancy clothes. Tom was decked out in a tux and he made it look good. I had a sparkly black dressed on.
The neck line was perhaps cut a little too low, but dammit I had the boobs, I might as well show them off. As for the sophisticated dances and beautiful music, not so much. Most of the night consisted of everybody doing their best to turn the dance floor into a solid mass of dry humping, and grinding hips. And all the while house music blared through the speakers, the bass so loud you could feel each thump in your chest. It got better later on when they switched to slow dancing, though. Tom and I did a simple two step. I laid my head on his shoulder.
“You look beautiful,” he said. I smiled at him.
“You’re not too bad yourself.”
After the second slow dance, Tom ducked out. He said he had to catch up with some friends and that he’d be back shortly. I sat at our table for a little bit watching other couples dance. Minutes passed. The friends were apparently taking a little while longer to catch up with than expected. Unfortunately none of my junior or sophomore friends had been invited. Definitely not Jane. So there was no one for me to talk to. I remembered I had a novel in my locker. It was just a short walk across campus to my home building. I could go and get the book. Worst case I’d make Tom wait for a few minutes. I had my phone in case he freaked out.
I pushed through the exit and walked out into the parking lot. My building was just across the lot so it wouldn't take long. A few of the cars were rocking gentle as I passed. Wow, I guess Tom had been telling the truth when he said it was a tradition. They hadn't even waited until the night was over. And then I realized that one of the rocking cars was Tom’s.
He must have lent it to a friend, right? It sounded like a good story… but I somehow knew that it wasn't true. I walked up to the car and opened the back door. Luckily I’d picked the right end and saw Tom and Jane's faces staring up at me in surprise instead of their behinds. Jane's skirt was hiked up around her stomach and by the floodlights in the parking lot I could actually see his cock buried half way in her pussy.
“What the hell?!” I yelled, but I turned around and stalked back towards the auditorium before either of them could say a word.
“Katie, wait!” I heard Jane yell after me, but I didn't stop. I didn't want to hear anything either of them had to say. I was shaking with anger but I kept my voice from cracking as I called my mom for a ride home.
I sat on the couch crying at home. I hadn't told my mom what happened. I just made some stupid excuse that Tom had a family emergency and couldn't give me a ride back. I don’t know if she bought it, but I really didn't care so long as she didn't try and have a ‘talk’ with me. The last thing I wanted to do was talk to my parents.
They had gone up to bed. Why wouldn't they? After all, it was late and both the kids were accounted for. And so I sat alone crying on the couch on what was supposed to be my prom night. I’d changed out of that damned prom dress and into my standard t-shirt and sweatpants pajamas. If I was going to be stuck crying, I was going to at least be comfortable. I don’t know what hurt more, the fact that Tom decided fucking anyone was good enough so long as he did it on prom night, or the fact that Jane agreed to do it.
And what the hell was Jane playing at anyway? She’d told me she’d never even given a hand job, she’d certainly worked her way up since last year! Screw both of them. Neither was worth the trouble. But I couldn't make myself stop crying no matter how many times I told myself this.
“Katie?” I looked up, it was Shawn. He stood in the doorway in his pajamas, which for a teenage boy consisted of a t-shirt and boxers. I turned away and tried to wipe the tears off my face.
“H-Hey, what’s up?” I asked, my voice shaky. I sniffled despite my best efforts to sound normal.
“What’s wrong? Why are you crying?” he asked.
“I don’t want to talk about it,” I said. I felt the couch shift as he sat down next to me. He hugged me and I gave up. I wrapped my arms around his neck and buried my face in his shoulder. “Tom… I walked on him… with Jane…” I sobbed.
“Oh my god, seriously? That asshole!” he exclaimed. Amen to that. He stroked my hair and just held me for a while as I cried. Eventually I cried myself out and looked up.
“Sorry about your shirt,” I said. There was a damp spot where I’d been crying.
“Hey, don’t worry about it, giving you a shirt to cry on is the least I could do,” he said. “Hey, I know, let’s watch a movie, we can take your mind off this.” He gently disentangled himself and picked a movie from the shelf. He picked Happy Gilmore, something absolutely brainless. It sounded perfect.
We sat watching the movie in silence for a while. We got to the scene where Adam Sandler beat up on the crocodile.
“Totally fake!” Shawn said
“What?” I asked, startled.
“That crocodile, I’ve seen more realistic ones floating in our neighbor’s pool,” he said.
“Oh shut up,” I said weakly.
“No, really. And the animatronics are awful too, I hear.”
“The dancing gofer, it’s in this movie, right?”
“Okay, now you’re just asking for it,” I said. And jumped at him, tickling hands extended. I pulled up his shirt and mercilessly tickled his sides.
“Katie, Katie! Stop! I surrender!” he gasped.
“No mercy!” I cried and went for his armpits. He giggled and writhed beneath me. With a massive heave he managed to work himself backward over the arm of the couch but I grabbed him by the hips at the last second and trapped him.
Déjà vu. In front of me was an erection poking up inside his boxers. I could actually see half the head of his cock peeking through the loosely buttoned opening. Wow, he had done some… growing in the last year, and not just his height. I could have let go of his hips and let him fall off the couch and pretend I hadn’t seen a thing. But something made me decide not to…
I pulled him back onto the couch. He was blushing fiercely and had started to turn his hips away from me, but I reached out and pushed down on the flap of his boxes. The head of his cock stuck out completely exposed now. I looked up at him. “I told you last time, the boner maneuver won’t save you,” I said.
I leaned down and kissed his cock. It pulsed gratifyingly at my touch.
“Katie… We really shouldn’t--” I put a finger to his lips. I unbuttoned his boxers and let the full length of his cock out. He was at least eight inches. I wrapped a hand around his shaft and jerked it a little. He gasped and lay back. That’s what I thought.
I pulled his boxers completely off. I licked his balls and then ran my tongue up along the length of his cock to the very tip and lapped up the precum that oozed out. I wrapped one hand around the base of his cock and then the other hand above that and jerked him hard and fast. He moaned and writhed on the couch, this time in pure pleasure. I leaned in and flicked my tongue under the head of his cock.
He arched his back and gripped the couch cushions. I gripped him harder and kept jerking. I saw his balls tighten and felt his cock tense just before he came. I wrapped my lips around the head of his cock and jerked it with one hand as he shot his load. I swallowed every drop. I felt his cock start to soften in my mouth.
“Not yet,” I said. I leaned down and sucked on his balls while rubbing under the head of his cock. After a couple minutes his cock had grown nice and stiff again. I stood up and untied the waist on my sweatpants, I let them fall the floor. Now I was only wearing my shirt and a pair of pink panties. I climbed on top of Shawn and let my panties rub again his cock. I leaned forward and kissed him.
He was hesitant at first, unsure, but I ran my tongue along his lips and he got the hang of it real quick. Soon he was kissing me with as much force as Tom ever had and I felt him lightly grinding his hips against mine. I lifted my shirt off and leaned in, pressed my breasts towards his face. His mouth found my left nipple and sucked on it. I gripped the back of his neck and pulled him tighter against me. As he sucked my nipple I reached back with my free hand and fondled his balls.
I could feel the warm precum soaking my panties as he dry humped me. When he came up for air and let my nipple go I stood up. He looked at me pleadingly, his cock almost painfully hard. I turned around and slowly worked my panties off, giving him a nice view of my ass. As Tom had said, it was a tradition to go all the way on prom night. But this was my prom night and if I was going to sleep with someone, why not the most important teenage boy in my life? Much better than the asshole that’d fucked my friend and constantly pushed me to do things I wasn't ready to do.
I turned back toward him and straddled him once more. I leaned in and nibbled his earlobe. “Thanks for being here for me,” I whispered. I reached down between us and put my hand around his cock. I maneuvered it against my wet pussy and slowly lowered myself on him. His cock slid inside me until finally the full eight inches were in.
He started to move his hips in motion with mine and after a few minutes of this we were fucking at full speed. It felt amazing. His cock would pull half way out and then our combined motion would slam it back inside me. Each thrust made his balls slap against my ass. I sat up and gripped the back of the couch, using it for leverage as I rode Shawn’s cock. I wiggled my ass back and forth, feeling the head of his cock touch near the back of my pussy.
His thrusting became urgent and he pulled down on my hips to give each thrust more power. I leaned back down and kissed him deeply. I felt my pussy start to tighten around his cock. Here it comes, I thought. I moaned and bucked as hard and fast as I could as I rode out my orgasm.
“Oh, god, Katie, oh god, I’m cumming!” Shawn called moments before I felt his cock begin throbbing wildly inside of me. It was very different feeling it from the inside versus in my hand or mouth. His cum felt like a wave of warmth. I kept bucking my hips at full speed. I could feel the cum leaking out over his shaft. I finally slowed as my own orgasm subsided.
Finally I lay with my head against his chest, listening to his heartbeat. His cock was still semi-hard inside of me. I could feel his cum oozing out of my pleasantly sore pussy. Shawn stroked my hair as I laid there. Fuck Tom I thought. Shawn was twice the man, even if he was fourteen and my brother.
And that’s how it happened. In the end, I made the choice. The circumstances were extenuating, but I take full responsibility. That was the only time we slept together. I think Shawn understood. It was just what I needed that night. But we’re still close, and we’ll always be there for each other.