Connor's Senior Year

"My friends think I'm exaggerating about how big your cock is," Megan said as she stroked the vein-ridged surface of my hard cock.

Leo had fallen asleep almost half an hour ago, and he snored lightly on the other side of Megan's naked body from me, his cock limp for the first time since he and I had arrived at Megan's to spend the evening "watching movies." Megan's parents were out for the night, and we didn't expect them home until at least midnight.

"You talk about my cock to your friends?"

"Well, you know Madison," Megan said. "She always has to one-up a story, and she thinks she can out-slut the rest of us. And for some reason she thinks Cory Mackie has the biggest cock in school."

"I'm not on the football team," I said. "So I wouldn't know."

"I made her a bet," Megan said, looking up at me for the first time since we'd finished fucking after Leo fell asleep. "I bet her that yours is bigger than anyone she brings."

"Brings?" I sat up in Megan's bed and she rolled toward me, giving me a much better view of her big luscious tits. They still had some bits of cum dried to them. "What exactly was this bet?"

"I told Madison to come over after school one night next week and she can bring Cory or whoever, and we'll all just fuck, and then I win the bet, because there's no way he's bigger than you."

"We'll all just fuck?" I said, raising my eyebrows.

"Well, you know," she said. "You and I can fuck, and Madison and Cory can fuck. But we'll all obviously be naked and she can see that I'm not exaggerating about how big your cock is." She grabbed my prick again and began to gently stroke it.

"And Leo?"

"Well, yeah," Megan said. "Of course Leo. Besides, Madison won't be the only one there."

"This keeps getting more interesting. Let me guess. Brianna and Lisa?"

Madison, Brianna, and Lisa were Megan's friends, or at least sometimes they were. I always got the impression that Madison looked down on Megan, but I suppose she pretty much looked down on everyone. But they were Megan's teammates last spring for softball, so they got along well enough most of the time.

Megan nodded to confirm my suspicion.

"And who are they going to fuck?"

"You," she said. "I bet them that not only was your cock bigger than Cory's, but Leo's was too. If I win, which I obviously will, you and Leo get to fuck all three of them. If they win, Cory gets to fuck me."

"What makes you so sure I'm bigger than Cory?"

"Are you serious?" she giggled. "Look at this fucking thing. You have a goddamn monster cock."

"So you're pretty confident you won't have to fuck Cory?"

"Would it bother you if I did?"

"Do you want to?" I looked at her seriously. "I mean, I love watching Leo fuck you, but that's Leo. But yeah, if you wanted to, I think it might be fun to switch things up on those guys. Because it sounds to me like your little bet is just an elaborate excuse to get us all naked in the same room, and I have to tell you, the idea of seeing Madison, Brianna, and Lisa naked does not suck."

"Would you want to fuck them?"

I paused and looked Megan intently in the eye. "Yes. Yes, I would love to fuck them. All at once or one at a time, either way."

"Cool," she said and smiled. "And I want to fuck Cory."

"Do you plan on running any of this by Leo?" I tilted my head toward our sleeping friend.

"Already did," she said. "Before you got here."

"I assume he was pleased with the idea."

"Very."

I kissed my best friend on the mouth and our tongues joined together. Megan's hand still moved up and down on my cock. I held one of her breasts in my left hand and weaved the fingers of my right through her hair, then pulled her head back and started to move my body on top of hers.

"Wait," she said. "I need to tell you something."

I sat back on my heels and my hard cock pointed straight up in the air.

"Let's go downstairs," she said. "Let Leo sleep."

* * *

"I know you noticed that I was clearly not a virgin last week when we first had sex," Megan said, seated next to me on the sofa in her parents' living room, still gloriously naked, but for the time being keeping her hands to herself.

"Sure," I said. "I mean, it just didn't seem likely that someone with no experience could suck my cock as good as you do."

Megan took my hand and took a deep breath. "A few weeks after I turned eighteen, I came home from movie night with you and Leo and walked in on my parents and my brother having sex right here in the living room. Ben was fucking my mom from behind while she sucked my dad's cock."

"Wow," I said, and immediately my mind flashed to my own home life since the first day of school, details of which I had still not shared with either of my best friends. Or Kaylee for that matter. "That must have been a bit of a shocker."

"To say the least," she said, rolling her eyes at my understatement. "I ran right past them while they tried to tell me everything was okay, and locked myself in my room. I thought I was mad at first, but a minute or so after I sat down I realized how wet my pussy was."

She was searching my face for a reaction, so I gave her my honest one. I was turned on by the idea of her wet pussy.

"I eventually let my mom in to talk, and she had a robe on, but it was this super skimpy thing that I could basically see through and I was about to tell her to fuck off when I realized how much I liked looking at her body. She told me that everything I saw was totally consensual between all three of them, and that Ben had been joining them and their friends since he turned eighteen."

"Their friends?" I raised my eyebrows.

"Yeah," she said. "My parents are swingers, or at least they're really into orgies and stuff."

That sure sounded familiar.

"Anyway, once my mom was sure that I wasn't going to run away from home, she left me to go to sleep, but I couldn't sleep. I just lay there thinking about my dad's cock and my brother's cock and my mom's tits and pussy and I just started masturbating. I came three times before I finally fell asleep. The next morning, and I swear he did this on purpose, I walked in on Ben in the bathroom, just standing there in front of the mirror naked with his cock all big and hard and I just..."

I squeezed her hand.

"I started sucking his cock."

She looked at me and waited for me to withdraw in disgust or shout or do something to confirm how fucked up she was.

"Megan," I said, holding her hand tight. "This morning, I had sex with my Mom and my sister."

* * *

Fourteen hours earlier

Martha marched into the house with bags over both of her shoulders and stopped dead in her tracks. My big sister was sweating from the exertion of carrying her bags in the heat of the mid-morning sun, and I could see the beads slowly descending into the valley of her cleavage. Her tits were as big as Mom's, on display in a tight halter-top under which there was clearly no bra. She was more slender than Mom everywhere else and a little taller. "Holy shit!" she gasped. "Mom! Connor!"

I stumbled back from the sofa, dislodging my raging erection from Mom's pussy, and inadvertently exposing its full size and orientation to Martha's wide-eyed stare. "Oh my god it's fucking huge!" Martha practically whispered, her eyes locked on my cock.

Martha dropped her bags and took off her clothes.

Or rather, she peeled off her top in a graceful motion that left her two big beautiful tits bouncing on her chest. She was more tanned than Mom, having had most of the summer off to hang around in the back yard or at the beach, but I hadn't realized how much topless tanning she'd been doing and I was suddenly sorry I'd missed it. Martha's tits were absolutely incredible. They were close enough to the same size as Mom's that I couldn't tell the difference, except that Mom's had just a touch more response to gravity, while Martha's stood up like they'd been sculpted there.

"I thought I told you not to stop fucking me," Mom said, finally pulling my attention away from my beautiful topless sister and back to herself, still leaning over the arm of the couch with her legs apart, still waiting for me to stuff my cock into her pussy again.

"You'd better do as she says," Martha said, now pushing down her shorts and panties together, bending forward as she did so, and showing me a splendid view of her hanging, swaying tits. "She gets a little testy if she has to wait too long for cock."

"Oh like you don't," Mom said to Martha, the older of her two children at just over nineteen and a half. Martha and our mother were often mistaken for sisters. While it was clear that Mom was the older of the pair, they matched in so many features and Mom was still quite young at only forty herself, that the mistake was understandable. Especially now that I could see both of them naked. Mom had slightly wider hips and a bigger ass, a little more meat on her thighs. Martha was a little taller, and her dark brown hair cut in a much shorter style than Mom's shoulder-length locks. But otherwise their bodies and even their faces were eerily similar. Same golden brown eyes. Same smile. Same tits. Same neatly trimmed pubic strip above their pussies.

My cock felt hard enough to burst when I finally made myself move back to Mom, holding it around the base and aiming it back to Mom's entrance, from where I'd just pulled it upon Martha's arrival. Mom backed into me and forced my cock deep inside her on the first thrust.

"Fuck yes, Connor, give it to me!" Mom cried. "Martha, come over here so I can taste that sweet pussy."

I slowed my thrusting and watched in awe as my sister lay on the couch in front of our mother and opened her legs, placing her pussy within reach of mom's searching tongue and sucking mouth.

"Oh my god, Mom, lick it!" Martha cooed. "Lick my pussy!"

I looked down at my cock disappearing into my mother's pussy and beyond her to my sister's magnificent tits. Unable to grab them, I opted to get my hands on Mom's. Her hard nipples dug into my palms as I squeezed hard on the twin globes and worked my cock in and out of her sucking pussy. Mom bucked against me and screamed into Martha's pussy and my big sister cupped and squeezed her own tits and writhed in the pleasure Mom was giving her.

"Oh fuck your pussy feels so fucking good, Mom!" I bellowed.

Martha caught me watching the heaving of her tits and smiled up at me. "You like my big tits, don't you little brother?"

"Fuck yes," I gasped as Mom's pussy started to clench and spasm and she lifted her face from Martha's pussy and howled that she was cumming.

"Yes!" Martha cooed. "Cum all over that huge fucking dick, Mom! I want to taste your pussy on Connor's monster cock!"

"Fucking CUMMING!" Mom screamed as she drenched my cock and balls with her pussy juices and I held her upright by the tits. Martha got off the couch and came over to kneel right next to where Mom and I stood, and she grabbed my cock around the base and helped pull my buried rod from Mom's cumming pussy. It emerged big and hard and glistening with our mother's cum, and Martha launched her face at it, sucking the head and several inches of shaft into her mouth and groaning as she took me in. The little vibrations of her voice traveled down the rest of my cum-covered cock and resonated in my dangling balls.

Mom tumbled forward onto the sofa, her orgasm having left her shaky-legged and breathless, and she rolled over to watch Martha suck my cock. Martha worked my pole between her lips and atop her swirling tongue while she lifted and squeezed her tits.

I reached down to get my hands on Martha's tits and Martha pulled back and popped my cock out of her mouth. "I'm so happy we're finally doing this," she said. "You have no idea how hard it was for me to stay out of your bedroom this summer when I could hear you fucking Kaylee in there. Do you want to fuck my tits and cum in my mouth?"

She didn't really wait for me to answer, instead just getting up off the floor and sitting down on the arm of the sofa. I didn't have to stoop over much start rubbing my cock on my big sister's big tits. Martha lifted her boobs and pressed them together around my shaft and spit into her cleavage to add to the lubricating mix of the saliva she'd left on my cock from sucking it, and Mom's cum.

"Oh fuck yes," Martha cooed. "Fuck my tits, little brother! Stroke this big fucking cock and give me your cum!"

"Oh my god, Martha," I groaned. "It feels so fucking good!"

Martha tilted her head forward and caught my cock head between her lips and sucked it until I pulled back for the return stroke of my cycle. Now every time I thrust forward, she sucked the bulging head of my cock for just a second and it came free of her lips with a loud pop every time.

"You two look so fucking sexy," Mom said on the sofa nearby. I tore my gaze away from Martha's incredible tits and sucking mouth to see Mom with her legs spread wide and three fingers of her left hand stuffed into her pussy while she worked her clit with her right. Her tits were pressed together by her upper arms and they jiggled constantly with the motion she created fucking herself. "Cum for Martha, baby! Give her your big hot load!"

My balls bounced off of Martha's upper stomach every time I thrust forward. The slippery constriction of her tits started their roiling and churning after just a few minutes of my thrusting and her repeated sucking.

"Oh holy fuck, Martha!" I bellowed. "I'm gonna fucking cum!"

"Give it to me, Connor!" she squealed happily. "Cum in my mouth! I want to taste it and swallow it!"

I boiled over and roared as the first thick spurt of spunk surged up through my cock and splattered across Martha's open mouth and over her nose and forehead. I pumped my shaft hard when she closed her lips around my cock head again to catch the continuing volleys of cock cream, working to swallow as fast as she could.

"Swallow my fucking cum!" I roared. The flow however quickly overwhelmed Martha's ability to keep up, and she had to pull me out of her mouth before I was done, and the last few spurts streaked across her face, joining the first and dripping down her cheeks and over her lips and chin, a few gobs managing to fall down onto her tits.

Mom practically shoved me out of the way and started licking up gobs of cum off of Martha's face, and I watched in awe as she held it on her tongue and fed it back into Martha's mouth. Mom's tits hung down and rubbed over the tops of Martha's and I climbed down onto the floor with them and wormed my head under Martha's butt. She rose up onto her knees to make room for me, then settled back down, setting her pussy right on my waiting mouth.

I licked my sister's pussy from bottom to top, dragging my tongue through her juicy opening and flicking it over her clit before starting over. Presumably done cleaning off Martha's face, Mom stood up and moved around to the other side of her daughter and got down on the floor with us to start sucking my cock. Martha quickly stood up, but only long enough to change directions and squat back down, putting her pussy back in my mouth, but now she could lean over and take turns with Mom sucking my cock.

I reached forward and grabbed Martha's tits while I worked my tongue in her pussy, and she writhed on top of my sucking mouth. I could feel her and Mom switching my cock back and forth between their mouths, one licking the shaft while the other sucked. Mom would occasionally stop to suck my balls, leaving Martha free to try to stuff more and more of my cock down her throat. I started to concentrate on licking and sucking Martha's clit, and she responded my moaning onto my cock.

Her moans became louder and she started to push her pussy harder against my face, and suddenly she was cumming. She lifted her head, leaving my cock to sway in the air until Mom caught it in her mouth, and howled out her orgasm toward the ceiling.

"AAAAAAGH! FUUUUUUCK!" Martha screamed. "I'M CUMMING, CONNOR! I'M CUMMING!"

She finally pulled away from my face and rolled off of me onto the floor, so I propped myself up on my elbows to watch Mom suck my cock while Martha recovered from her orgasm.

"Kaylee really taught you well," Martha groaned as she rolled on the floor nearby. "I'm almost glad you spent all that time with her learning how to fuck this summer."

"Almost glad?" I raised an eyebrow at my big sister. Mom continued to suck my cock without comment.

"Well yeah," Martha said. "I wouldn't have minded a chance to teach you all of this stuff myself."

"I'm sure there is more I can learn," I said, grinning at her.

"I don't think you need any special skill for what I want," she said.

"What's that?"

"I want to ride that fucking monster cock until you fill me up with your cum," she said.

"Maybe we should take turns," Mom said, finally deciding that she needed to add to the conversation.

"Fine," Martha said. "But I get his cum in my pussy."

Mom laughed. "My greedy little cum-slut is home. When we're done, you're going to have to explain that to me, by the way."

Mom got out of the way so that Martha could straddle me and lower herself down until my cock head was pressed in between her pussy lips at her hot opening. I gazed in awe at her huge swinging tits as she bit her lip and started to slowly impale herself on my cock.

"Oh fuck, it's fucking big!" Martha growled when my cock head entered her channel. "So fucking big!"

Martha's pussy squeezed and clenched my cock as she slowly lowered herself more and more until we finally had it as far inside her as it would go. Mom muttered words of encouragement and played with Martha's tits and pussy while my sister got used to the sensation of being completely filled with her little brother's cock.

"That cock feels good, doesn't it, baby?" Mom moaned. "Connor's massive cock is going to make you cum so good, Martha!"

"Oh god I'm cumming already!" Martha wailed, and the clenching of her pussy intensified for several long pulses before she relaxed, having now soaked me with her cum.

"Ride that cock, sweetie," Mom said. "Keep riding it and keep cumming."

Martha slumped forward on top of me, pressing her fantastic tits into my chest and resting her forehead against mine. Her hips continued to buck, working my cock in and out of her pussy while I simply lay still.

"Your pussy feels so fucking good, Martha," I whispered to my beautiful big sister. "Cum all over my cock! Ride it! Fuck it!"

"YES!" Martha screamed. "I'm cumming again! FUCK FUCK FUUUUUUUCK!"

This orgasm caused her to tumble to the side and roll off of me again, and she bucked and thrashed on the floor beside me while Mom climbed up and dropped herself down on my cock in Martha's place.

"You did so good making Martha cum, baby," Mom said. "Now make me cum too. Fuck me back while I ride you!"

"Oh fuck, yes that feels good!" I said as I grabbed Mom's hips and began to push and pull, forcing my cock deeper into her pussy and then back again, all the while staring in mesmerized awe at her big bouncing tits. I'd already blown my load three times this morning, once in Mom's mouth, once in her pussy, and once in Martha's mouth and all over her face, but my cock was still an iron bar as Mom and I fucked each other hard.

Soon Mom was screaming and her pussy pulsing as she started to cum again. Martha sat beside us rubbing her own pussy and watching as our mother completely covered my cock with girl-cum again. Once Mom's orgasm had passed, Martha helped her to her feet, and I followed my mom and sister back to the sofa where Mom sat down to catch her breath, and Martha sat beside her and spread her legs open and looked up at me.

"Fuck me, Connor," she said. "Put your cock in me right now."

My cock was covered in a mixture of Mom's and Martha's cum, waving shiny and rock-hard in the air as I dropped to my knees between Martha's legs and nudged my cock head between her pouting juicy pussy lips.