Gangbang Your Way to His Heart

The summer after I finished college, I moved back into my parents' house and tried to find a job. The only openings were at places like Dairy Queen or Wal-Mart, and I don't know - I guess I had too much pride to accept those after I'd gotten my degree in something as esoteric as Latin Classics.

But my pride flew out the window when my older brother's friend, Derek, showed up at the door one day.

"Derek!" I said when I saw him, immediately breathless. "Are you - I mean, Tim isn't here. They finally switched his shift at the gas station."

My brother was three years older than me, but he'd lived with my parents since graduating high school. He never went to college, never got a job that paid more than minimum wage. He mostly locked himself up in his childhood bedroom and got high. It was pathetic.

It was the future I worried I'd have, if I didn't get a fucking job.

But all thoughts of my career flew out of my head when I saw Derek. He and my brother had been friends since grade school, and I'd always had a crush on him. He was tall and broad-shouldered, with interesting green eyes and a way of smiling at you that made you feel like you were the only person in the world. Not that I was on the receiving end of most of those smiles. He treated me like I was barely beneath his notice most of the time, except for the few times when he and my brother had ganged up to make fun of me for the music I listened to or the way I'd started dressing or the stupid thing I'd just said. Derek made me feel about two inches tall sometimes.

And yet I was half in love with him, had been for years. How sick was that?

Derek leaned against the door frame, his gaze running from the top of my head down to my feet. Had I imagined the way he'd checked me out? The way his eyes lingered at my breasts, braless underneath my baggy t-shirt as I'd been lounging around the house?

"Will Tim be home by eight?" he asked. "There's a party tonight at the place of some of our high school buddies. It'll be like old times."

I knew the kinds of parties Derek was referring to, but I'd never been invited to one myself. Everyone would meet up at one of the rich kids' houses, or anywhere where someone's parents were out of town. They'd drink and smoke and do harder drugs that I didn't even know by name. They'd hook up in bedrooms and closets. They'd come back to school on Monday still glassy-eyed, secretive grins on their faces when they caught the eye of a classmate who'd been at the party, too.

"He's not supposed to get off until midnight," I said.

Derek looked at me again, and this time there was no denying that he was checking me out. Underneath my shirt, I felt my nipples tighten in response.

"And when do you get off?" he asked.

I giggled, like a stupid little girl. "I don't have a job," I said. That's not what he meant and I knew it. I thought briefly back to the time when he'd . . . but that was still an embarrassing memory, even if the thought of it made me hot all over.

"Then you're free," he said. "Pick you up at eight?"

"Sure," I said. I hoped my voice was breezy, as though I hadn't been dreaming about this exact moment for over a decade. He smiled at me, that special curving of the lips that made me feel like the only woman who existed on the entire planet, and somehow I knew that he saw right past my false nonchalance.

***

Derek was right on time, and he seemed to appreciate the outfit I'd changed into for the party - a kicky skirt and a tight t-shirt that read Virginia is for Lovers across my breasts. I wasn't wearing a bra, since I was an average C but perky enough not to need one, and under my skirt was my sluttiest thong underwear. I hoped Derek would like it, in the event that we found a bedroom to hook up in at the party. I'd already decided to myself that I'd go wherever the night took me, and if that meant a brief, meaningless fling with the object of my childhood crush, well, bring it on.

Derek told me that I'd probably recognize a lot of people from high school, and I did - a few from my own class, and a few from the classes above me. There was Pete, the guy who'd been crowned homecoming prince the year before I graduated. Dave, the guy who'd taken pictures for the school yearbook. Jackson, the burly football player who'd been in the class before mine and my class after he failed his senior year.

I was a little discomfited to see even Paul, who had snapped my bra sometimes when we stood in line at the cafeteria, and who once told me I had DSL, which I really thought meant a kind of internet until someone explained it to me years later. Dick-sucking lips.

I averted my face, hoping he wouldn't see me.

There were a few other guys who I didn't know, but I was surprised that there were no other females at the party. Had they just not arrived yet?

Derek got me a beer, opening the top for me with his bare hands, and I smiled gratefully. I tipped the liquid down my throat, feeling it warm my belly. This was nice.

Derek and I sat on a couch, and I noticed that he sat much closer to me than he needed to. I thrilled when he placed a hand on my thigh, squeezing slightly. He smiled at me.

"So you work at the bank now?" I called over the noise, hoping to start conversation. Tim told me that Derek had recently been promoted to some position just under vice president at the local bank where he worked. I had no idea what exactly he did, but it sounded terribly important, especially for someone who was only in his mid-twenties.

"I like your tits in that top," he yelled back, and I flushed. But hadn't I hoped he would notice? I gave him a shy smile as I took another swig of my beer.

It wasn't long before the weed came out, and people started passing around a joint. I took a couple of hits off of it, even though pot made me lightheaded and always had. I felt the room shift slightly even from the little bit I'd inhaled, and I could feel my limbs loosening.

"I think about you all the time," Derek said into my ear. "Tim's little sister, spread eagle, touching herself. Do you think about that?"

I felt my face heating up even more than it had before. Somehow, I hadn't expected Derek to actually bring it up, even though of course I knew immediately what he was referring to. I had just started high school, and he'd walked in on me masturbating. I'd been so embarrassed, but he'd just stood in the doorway, his arms crossed, and watched.

I should've stopped, covered myself up. But something had made me continue. To this day, no other orgasm could compare to the one I'd had that day.

"Sometimes," I said.

"Does it make you wet to think about it?"

Things were escalating much faster than I'd expected, but I was okay with it. I gave myself into the sensation, squeezing my thighs together, relishing the hot wet burn I felt deep in my loins as I remembered the scene. Maybe Derek would ask me upstairs soon, and I'd give him my hand and follow him to a bedroom, where we'd have sex. Maybe it would be all he'd ever give me, and that would be okay, but maybe . . . just maybe . . . he'd see how good it was between us, and how worthy I was of his love. I could make him happy. I knew I could.

I still hadn't answered his question, though. It felt strange to be talking dirty in the middle of a party. There was a guy I didn't know sitting on the other end of the couch, talking to a guy sitting in an armchair only a few feet away. Across the room, several of the guys I knew from high school were drinking beers and talking to each other.

"Touch yourself," Derek said, so quietly I almost didn't know if I'd heard correctly.

"Sorry?"

"Touch your soaking wet pussy," he said.

I glanced again at the guy next to us, who wasn't seeming to pay us any attention. Still!

"Here?"

He took my hand in his, and guided it under my skirt. His grip was strong, but I could've pulled away. I didn't.

"What kind of underwear are you wearing?"

"A thong," I whispered.

"What color?"

"Hot pink."

"Hot pink, just like your pussy." He'd moved the scrap of fabric covering my mound aside with his fingers, and was pushing one of my fingers inside my secret core. I glanced up to see if anyone was watching, but no one seemed to register what was happening.

"What do you think about when you touch yourself?" he asked. "Do you ever think about me?"

All the time. I nodded.

"Well, I'm right here, baby. Watch my eyes as you get yourself off."

I wasn't going to masturbate in the middle of a party! I started to withdraw my hand, but something in his eyes made me put it back, sliding two fingers into my pussy. It really was wetter than it had ever been before.

"Do you like that?" he asked.

I nodded, moving my fingers inside myself, feeling every small brush against my vaginal walls. This time, when my gaze flickered around the room, I saw that the guys I'd known from high school were no longer talking. Their eyes were on me - Pete, Dave, and Jackson - and they were all just watching. Pete was rubbing his crotch with one hand.

"Watch me," Derek said, and I dragged my gaze back to his. "Come on, dirty girl, I know you like it."

It wasn't like anyone could see anything, I reasoned. My skirt was lying over my hand, and if it weren't for the motion of my arm, you might not be able to tell what I was doing at all. I let myself moan just a little, rubbing my clit between my fingers.

"That's it, baby," Derek urged with a little groan of his own. "Don't hold back."

The guy on the couch and his friend on the armchair were watching me too, now. In another corner, Paul was standing with his beer bottle to his mouth, his gaze fixated on my crotch as I worked my fingers inside myself. The need for release was building in me, higher and higher, until it broke in a flood of my own juices over my fingers, as I panted out my orgasm.

Across the room, Pete had pulled out his dick and was jerking it. I withdrew my hand, and Derek put my two fingers in his mouth, sucking off the taste of me. I heard a smattering of applause in the room, but I didn't look away from Derek, too embarrassed to acknowledge our audience.

"I can't believe I did that," I whispered.

"You're a goddess," he said, smiling, and my heart lifted. I'd hoped that he'd find me hot tonight, that he'd look at my body and realized that his friend's kid sister had grown up, but I hadn't thought he'd look at me with such reverence. He thought I was a goddess!

"There's only one problem," he said, frowning slightly, and I was thrown by his sudden change in mood. My body still felt heavy and sated, but my mind was racing with desperation. A problem?

"What's that?" I asked, licking my lips. He held my face in his hands and kissed me soundly, his tongue invading my mouth, licking my teeth, running along the seam of my bottom lip. Then he had me by the hair and was dragging me up off the couch until I kneeled in front of him, trapped between his legs and the coffee table.

"You got off," he said, "but I didn't."

He was unzipping his pants, and I glanced over at the guy on the couch, who had moved closer and was leaning in for a better view, a leer on his face. The guy on the armchair had stood up, and announced, "Holy shit!" to no one in particular as Derek guided my head towards his dick.

"Derek -" I started to protest, or suggest perhaps that we find a private room, but his cock was already filling my mouth, pushing past my teeth and deep into the back of my throat. His hand was still tangled in my hair, and he roughly shoved my head against his crotch until I almost gagged from the length of him, dragging me back before doing it again. He sat still, letting me do all the work, and when his hand finally left my head, I found myself still bobbing up and down on his long, hard cock, feeling it pulsing in my mouth.

"Oh, yeah," I heard a voice from beside me say, and then someone was shoving the coffee table away, kneeling behind me to grab my tits through my shirt as I sucked dick. My cry of protest was muffled, lost in the wiry thatch of Derek's pubic hair as my mouth moved up and down, up and down the length of cock. My unknown assailant was pinching my nipples, dragging the hem of my shirt up impatiently for better access, pushing his erection against my ass.

The guy on the couch leaned over, wanting a piece, too, and he grabbed onto one of my tits and started sucking my nipple, stretching me painfully in his direction while from the other side, my unknown assailant was trying the same thing in the opposite direction. And in the middle was Derek and his cock, and I could tell from the way that it jerked in my mouth that he was close.

"That's right, baby, make me cum," he shouted, slamming my head against him. From behind me, someone's finger was probing at my still-wet slit, and I tried to move to avoid the contact. The hand got more aggressive, pinching my ass, pulling at my pubic hair, shoving the tiny scrap of fabric standing in its way aside.

I tried to say No, no, no, but my mouth was so full with cock it came out more like Nnng, nnnng, nnnng, and then Derek's cum was pumping into my mouth as if from a hose, loads and loads of it swishing around and sliding down my throat.

Someone was grabbing my hair, yanking my head in another direction, and I was spun painfully on my knees until my open mouth was shoved onto another waiting cock. I looked up to see Paul, and he smiled down at me.

"I always knew you had dick-sucking lips," he said.

It wasn't supposed to be like this. I had planned to hook up with Derek, the object of all my teenage fantasies. I hadn't intended to give a blowjob to Paul, the guy who'd tormented me in high school, while my t-shirt rode up under my armpits to leave me totally exposed. My mouth still tasted salty from Derek's cum, and now I was tasting Paul, too, taking every inch of him as I felt the head of his dick prod at the bag of my throat. I gagged.

"That's right, bitch," he said. "Choke on it."

This wasn't what I wanted . . . and yet my pussy was wetter than it had ever been, and I was brought back to that amazing orgasm I'd had almost a decade ago. I wanted that again. And right now, I didn't care who gave it to me.

I sucked Paul until he blew his load right into my mouth, and I drank it down eagerly, laving his dick for every last drop with my tongue. When he was done, another guy took his place, and then another, and another. I lost count of how much cock I fucked with my mouth, or how many times I tasted hot, sticky cum on my tongue. The whole time, I would glance over at Derek, and he would be smiling.

When it was Jackson's turn, he lifted me from under the armpits onto the coffee table, where he forced me down onto all fours. He slapped my face with his huge cock - easily the biggest of any of the ones I'd had so far - before shoving it into my mouth. From behind me, I felt someone ripping at the thin strings that held my underwear on, and then I was naked under my skirt, hot and wet for the dick that slid into my pussy. I'd wanted it so badly that I moaned when I felt it go in, and I ground my pelvis against my unknown savior, loving the sweet suckling sounds of him thrusting into me.

Jackson pulled out, squirting all over my face. There were two different sets of hands grabbing on my tits, another set slapping my ass, and it was impossible to tell how many different people were touching me at that moment. Derek came down to kneel in front of me.

"You like this, don't you, you dirty slut?" he asked.

My lips were parted, my breaths coming in shallow pants while from behind me, I felt a load of cum squirt into my pussy, and felt only a moment of air against my exposed clit before another dick filled me up again. A new man was fucking me now, harder and faster than the first, and my tits were swinging from the exertion. Of course I liked it. Wasn't it obvious?

But no, he wanted me to shout it. "I love it," I said, half-growling the words. "I need it. Fuck me harder. Harder!"

"This bitch is in serious heat!" one of the guys said, and the guy violating my pussy listened to my command, slamming his balls against my ass as he gave me every last centimeter of his hard cock.

Derek reached to the hem of my shirt, still tucked under my armpits, and drew my shirt over my head. Instead of pulling it all the way down my arms, he stopped when it covered my face, only the bottom ends of my hair poking out, swishing the table with every movement. I could see a sliver of the light pinewood of the coffee table, and that was it. Angry, greedy hands pulled at my tits, stretching out my nipples, pinching them, but I had no idea who they belonged to, or how many there were.

The guy behind me shuddered as he spent himself inside me, and then I felt another cock nudging at my entrance as a third man fucked me doggy-style. Was it Derek? Had Derek even had me yet, or was he waiting for something, letting everyone else have his turn first? I wanted to give him a good show, to let him know how in love with him I was, and I cried out from under the shirt as my third assailant drove into me.

Someone spanked my ass - the same guy who was fucking me, or someone else? - and the harder he did it, the more I panted and moaned, until I was almost sobbing from wanting to orgasm. I could feel it building, but I really wanted to let it go with Derek inside of me. How would I know when it was him?

I heard a sound that at first I couldn't place - click click click. I didn't really care what it was. But then I saw a flash of light briefly reflect on the coffee table, and more clicks, and I realized. Someone was taking pictures - probably Dave, the yearbook photographer from high school. I didn't want there to be any evidence of this, of the way I must look - my tits hanging down, a stranger's cock ramming into my pussy, my ass up in the air as it bowed and waved with the movements.

But the idea of how I must look also just made me hotter, and by the time I felt my third assailant fill me up with cum, I was ready for anything.

Or so I thought. But then I felt another set of hands grab me by the waist, and the head of someone's cock started pushing against my asshole.

"No," I said, thrashing in place, swaying my ass from side to side to try to avoid this final indignity. The t-shirt was still muffling the sound of my voice, but I cried out. "No, please - it'll hurt. I know it'll hurt."

I heard a voice next to my ear, talking to me through the thin fabric of the shirt. "Don't you want it, you nasty little bitch?"

It was Derek's voice, and I moaned. Of course I wanted it - I wanted whatever he could give me. I would do anything for him. Hadn't I proven that by now?

I thrust my ass higher in the air, as if presenting it to him. Here, take it. It's yours.

And he did, pushing his dick into my small, tight anus. It felt like I was being ripped apart, and I felt hot tears spring to my eyes, but by the time he was all the way in and had started to move, the pain turned to pleasure as he fucked my ass. I grunted with every movement, every time he buried himself in me deeper, like the bitch in heat that I was. Uh uh uh uh.

My tits were hanging down while he fucked me, and someone was slapping them, flicking my nipples. I could feel the pressure building inside me, and I gave into it. It's okay, it's Derek, it's okay.

I shouted out my orgasm as he pounded my asshole, and he lost it then, too, spilling his seed deep inside my spread ass cheeks, into the previously unviolated hole.

"You have a dick-taking ass, too," a voice said next to my ear. I struggled to move my head out from under the shirt, just to look. When I lifted my neck, I saw that Derek was standing on the other side of the room, a smile on his lips. I craned my neck to the side to see Paul, whose semi-erect cock was still inside me as he squeezed my tits together with one hand.