Romping on Winter Break - Day 06

Here is the sixth part of Romping on Winter Break. I thrive off feedback, so make sure to send me a message if you've enjoyed the story so far. Comments make me write faster. Just a few days left in the story. Enjoy.

MaiaEmpire

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Day 6

I regained consciousness the next morning, rolling on my side stretching my back and arms. I expected to feel pain from the extreme overuse of my pussy and ass from last night, but to my surprise it wasn't that bad. I reached behind to my butt crack to probe and inspect my asshole, which was a little tender but not on fire like it had been previously. I think Rylan was right; the more I took cock in my ass, the more accustomed to it I became. Not to mention the more I wanted it filled, and I started rubbing it faster just thinking about it. I quickly stuck my finger in my mouth, and reached back to slip my spit-covered finger inside.

As I sighed and softly probed my anus, I opened my eyes to see Rylan lying on his stomach and softly snoring. Brooke and Mark were nowhere to be seen, but I could hear water running and I assumed they were showering. As I fingered my ass, I could see Rylan's smooth bottom rising and falling as he breathed. His waist was fairly slim for a guy, and he had a nice curve to his cheeks, which gave it a feminine look.

I kept watching his cute ass as I began to rub the inside of my own ass faster. Rylan was so beautiful, I could hardly stand it. I was about to add a second finger inside of my ass, when my foot knocked into the strap-on and dildo lying at the edge of the bed. I leaned up to see it properly, and then back at Rylan's ass. A little mischief entered my head. I grinned wickedly and removed my finger.

Slowly, as to not disturb Rylan, I slid off the side of the bed. I tip-toed to the harness and carefully lifted it. I felt the firm head of the dildo as I slipped my feet into the straps and pulled the white belt to my groin. I loved the feel of the base pressed against my pussy and the two harnesses reaching down and around my buttcheeks, leaving my ass bare. Once the strap-on was in place, I snuck over to the bottle of lube on the nightstand with my fake dick swaying in front of me. Rylan continued to snooze on the other side of the bed.

I smeared the lube around the shaft and head of my fake cock, making sure it was ready to fuck my oblivious boyfriend. I moved to the foot of the bed, and crawled up to Rylan's exposed ass. It was right in front of my face, so I spread the cheeks with my hands and lowered my lips to his asshole. I darted my tongue around and inside his anus, and I could feel Rylan start to stir a little bit.

After a few minutes of rimming my half-conscious boy, I lifted myself up and positioned my dick against his butt crack. I still didn't think he knew what was going on. Aiming it with my left hand, I poked the head against his sphincter until it accepted it with a little pop. Rylan let out a sleepy gasp, his mouth open but eyes still closed. I gave his ass a moment to get used to opening up, and then I pushed it in deeper, eliciting another moan from Rylan. Instinctively, Rylan's ass raised a bit, giving me easier access as I pushed the rest of the fake cock inside of him.

My hips were pressed against his butt, and my thighs were pressed against his hamstrings. I started to rotate my cock inside of his rectum, as Rylan intuitively worked his ass against it. His eyes remained closed. I slowly slid my cock back and pushed it into him for a few strokes, and then started to pump into him. Rylan reflexively matched my strokes and raised his hips against me.

"Fu-u-uck, Mark..." he managed to whisper.

I grabbed his hips and pulled him up on his hands and knees as I continued to fuck him. He started moaning like a bitch in heat, his head raised and his mouth agape. He finally glanced back at the unexpected ass-fucking he was recieving.

"Holy shit, Beth! Are you fucking me!?"

"That's right babe," I growled, "do you like taking my cock on your hands and knees?"

"Oh, god yes," he moaned.

"Say it again," I commanded, as I slammed into him harder.

"I love taking your cock in my ass, Beth!"

I slapped his ass. "Again!" I yelled at him.

"I love taking your cock like a bitch! Fuck me harder, Beth!"

It was thrilling dominating Rylan like this. As I continued to pound him, I saw Brooke come in from the bathroom. She was naked and freshly showered, but upon seeing Rylan on all fours getting fucked, her hand immediately went to her pussy.

"I thought I heard someone getting fucked in here," she cooed as she got in closer, "do you like getting fucked by your girlfriend, bitch boy?"

Before he could respond, I spoke up. "Crawl under him and let him fuck you while I fuck him."

"Pussy, or ass?" Brooke inquired, as she lay on the bed smiling. She wasn't asking Rylan.

"Ass," I ordered. For some reason, I was obsessed with anal this morning. Brooke reached over to the lube bottle and hiking her legs up she smeared it on her asshole and pushed some inside with two fingers. She also reached under Rylan to slick up his bouncing cock. I lifted Rylan up a bit, as Brooke got on her stomach and slithered underneath Rylan. I held Rylan's hips against me as he lowered himself down and aimed his cock into Brooke's ass.

I could feel Rylan collapse his hips into Brooke, as I heard her gasp as he invaded her with his cock. Rylan held himself up by his elbows, but his hips were firmly pressed against Brooke. My dildo remained buried in his ass. Rylan started to move his hips into Brooke, who was supporting both of our weights, and as he did so he was fucking himself against the strap-on. He was both fucker, and fuckee. From on top of them, I could hear both Brooke and Rylan moaning against their respective anal attacks, and though it was fun fucking into Rylan with my fake cock, I have to admit I was anxious to get an ass-fucking of my own.

That was when I felt a pair of hands on my hips from behind. I'm not sure how, but Mark had quietly snuck up behind me. His own cock was already greased up, and his fingers started smearing lube onto my crack. When they reached my hole, I hungrily pushed back and his fingers disappeared inside of my rectum.

I groaned as his fingers lubed me up. Mark chuckled as I worked my hips back onto him. "It looks like Beth is ready to go!"

I slammed my fake cock into Rylan, who in turn slammed his cock into Brooke. "Shut the hell up and fuck my ass! NOW!" I screamed at Mark. He aimed his cockhead at my anal entrance, and tentatively pushed the head in. He was being gentle, but I was not having it. I needed my ass full of cock right then and there.

"I said FUCK ME, goddamnit!" I yelled at him, as I pushed my ass back on his cock, taking it all in one motion.

My fake dick popped out of Rylan, who gasped as it exited his ass. Mark gripped my hips and held himself against me, and I reached down and reinserted the fake cock into Rylan, all the way to the hilt. As soon as it hit home, Mark's cock started pumping in and out of my ass. His fucking rhythm took control as it synchronized to the fucking I was giving Rylan, and the fucking he was giving Brooke.

We must have looked like quite a scene with Brooke on her stomach, legs splayed and supporting Rylan, who himself had his legs spread as he got fucked by myself, who was in turn being slammed from behind by Mark. The three of us took our respective dickings in stride, and somehow me and the boys managed to continue to fuck the asses before us.

I have no idea who came first, but I soon felt Mark shooting his load deep inside of me, as I felt Rylan spudder into Brooke's ass. Brooke continued panting though her own orgasm, face down into the mattress as she held her butt cheeks apart accepting Rylan's pulsing dick. I myself came as Mark finished cumming and thrusting into me. We lay there for a few minutes as we ran out of steam and peeled off of each other satisfied.

Brooke was still on her stomach after graciously supporting all of our weight, with her gaping asshole sticking up and leaking Rylan's cum. I slid the strap-on off of me, and laid down on my belly next to Brooke, my own ass full of Mark's cum.

"Clean us up, boys," I casually ordered as I folded my arms under my head. Immediately, Mark lowered his face into Brooke's bum, while I felt Rylan begin to rim my own. The boys expertly licked up the cum leaking from our asses, and stuck their tongues as deep into us as possible to get whatever they could. It felt so good to have a tongue back there.

Once us girls were cleaned out, Rylan sat on his heels appraising us. "Damn babe, one day you get massively triple-fucked, and the next you suddenly become a big-dick swinging boss!" he commented. Mark and Brooke laughed.

I rolled on my side and held my head with my hand looking at him. "Are you complaining, my love?" I teased.

"Absolutely not! Look out, Mark!" Rylan said, slapping his ass. "Beth might give you a little run for your money when it comes to fucking my ass!" We all laughed at that one.

Brooke spoke up from her pillow. "Well, it looks like I have to take yet another shower this morning. Thanks a lot, Beth!"

"Don't blame me! Rylan is the one who came in your ass!"

"Oh, please," said Rylan, "I am not taking any responsibility for this Beast With Four Backs. That was all your initiative, Beth."

"Seconded," nodded Mark.

I smirked at all of them. "I refuse to apologize for being an ass freak. Especially with asses as hot as you three."

Brooke raised her eyebrows. "Are you saying our asses are hot, or we are asses who happen to be hot?" Rylan and Mark snickered.

"Take your pick! Now stop joking around and let's hose off!" I commanded.

The boys helped Brooke and I to our feet as we headed into the bathroom to shower. I picked up the discarded strap-on and removed the dildo from the harness to toss into the sink. I wasn't sure about how to do maintenance on Rylan's sister's poor dildo, but I figured since it had been in all of our asses, and in Brooke's and mine's pussies, it probably needed to get cleaned a bit.

Rylan turned on the dual shower heads, with Brooke and Mark piling in after him. After I dumped the dildo in some hot water and soap, I joined the three of them who had already begun stroking and feeling each other up in a tangle of steam and suds. As I stepped in, I felt Mark's lips on my neck, Brooke's hand on my bottom, and Rylan's on my pussy.

We spent quite a while under the shower heads, alternating partners. First Mark started making out with me, gripping my butt cheeks like he had earlier and dominating my mouth. Next it was Brooke, who's soft lips and even softer breasts pressed against mine, her fingers delicately tracing my back. After her it was Rylan, who kissed me passionately and held me tight against his smooth body. Then it was back to Mark pinning me against the tiles. We must have rotated like this half a dozen times before we finally exited the shower.

It was well after noon by the time we dried off. Brooke and I put up each other's hair, and we scampered downstairs. Since we skipped breakfast, Rylan decided he wanted to grill up some burgers while we all relaxed next to the pool. While he worked on the burgers in the kitchen, Brooke, Mark, and I laid ourselves on the pool beds to soak up some sun on our naked skin. A lot of the snow had melted off the glass roof, so it was a good opportunity to tan up. We laid out and chatted while Rylan worked in the kitchen.

In time we could smell the meat cooking and Rylan brought it all out on a tray to one of the tables next to the pool. We stood up, stretched, and made our way to the table to feast. Rylan had even cooked up some french fries, and brought out some bottles of beer. We clinked our bottles to cheer, and went to town. I don't know what herb or spice Rylan added to the patties, but they were phenomenal.

It was Rylan who spoke up first while we ate. "This has been such an awesome week."

"I know what you mean, man," said Mark, "this week has been fucking amazing!"

"Emphasis on fucking," quipped Brooke.

"I'm gonna be sad when Charles comes to pick us up on Saturday. It'll really fucking suck," lamented Rylan.

"Ug, it's two days to Saturday. The week has passed by so quickly. It feels like we just got here!" I said.

"I can't believe we haven't worn clothes this whole time," added Brooke.

"I can't believe I've cum so much this whole week," added Mark.

"I can't believe I've had lesbian sex and anal sex. And loved it," I added.

"Well, I for one believe this has been the best week of my life," said Rylan, as he thoughtfully took another bite of his burger. "I don't want it to end."

There was a very full pause as we all quietly chewed our food. It felt like we were all exposed, and not just because we were all naked. Like we were all facing the same kind of dread about what was coming up. This Winter Break was a blast, but half of our senior year was over, and then it would be summer vacation, and then...well, I guess college or whatever. We would be able to hook up with each other occasionally, but it wouldn't be close to what we had this week. Just running around, totally naked, and screwing each other in every way imaginable.

I know for my part, I felt freer than I ever had. That old cliché about exploring your sexuality; well, it was absolutely true. I was a completely different person. I had only been with two guys sexually before, but this week I had multiplied everything by a hundred. I had been eaten out, been fucked, been ass-fucked. I had been double-fucked and even triple-fucked. I kissed a girl, and had tasted another girl's pussy. I even wore a strap-on and fucked a boy and girl, and had it done to me! This was all unimaginable as recently as last week, and I wasn't ready to have it end.

We all sat sullen as we stared at our empty plates, clearly thinking the same grim thoughts about the future. Brooke was the one who broke the silence.

"Guys, we shouldn't be so down. Look at us, we're fucking hardcore sex maniacs. We're fucking professionals. And this week's not over yet. Rylan, what time is your driver coming to pick us up on Saturday?"

"About noon. The cleaning staff's coming afterwards to clean up the place and shut it all down again for the rest of the winter," said Rylan.

"Fuck, we'll probably have to get rid of all of the evidence," said Mark.

"See," said Brooke, "we still have plenty of time. And plenty of fucking to do." She stood up and looked at me. "C'mon, Beth. Let's stop being gloomy and put on a little show for the boys."

She took me by the hand as I stood up. Rylan and Mark both smirked as Brooke led me to one of the pool mats. She laid me down on my back, and eased herself between my legs. She started kissing my belly, and slowly worked her way up. Rylan and Mark each grabbed a beer and sat close by to watch as Brooke's lips went to my breasts.

My hands caressed her back as she began nibbling on my neck. Her boobs pressed against mine, with both of our nipples firm and hard. She lifted her right leg over my thigh, and I felt her pussy push against my hip bone. Her own thigh pressed against my wet pussy. She lifted her face to look down at me as she smiled. I stroked her hair, and pulled her lips to mine. As we kissed, we grinded our pussies against our thighs.

It wasn't long until both of us were moaning into each other's mouths. Brooke's hips started moving furiously against my raised leg, and I soon felt her cum all over it. Almost immediately, I gripped her thigh to pound my pussy against her, and in no time, I orgasmed as well. As I came down off my high, Brooke kissed her way down my body and began to lick all over my hips, my thighs, and inner legs.

I held her head with my hands, guiding her to my sex, as I glanced at Rylan and Mark. Both of them were on their second and third bottles of beer, which made me wonder how long I had been making love to Brooke, and were stroking their semi-hard dongs. They were definitely enjoying the view.

"You like licking Beth's twat, babe?" asked Mark.

Brooke pulled up for a moment. "Fuck yeah," she said, before burying her head in my mound once again.

How 'bout you, Beth," asked Rylan, "you love having a girl lick your pussy?"

"Oh my god, it feels so good. I'm so gay for you, Brooke," I babbled.

"Let's see some 69 action, ladies!" demanded Mark, who popped open another beer.

Eagerly, Brooke lifted off of me and swung her legs past my head, and lowered her pussy lips to my mouth. Our torsos smashed together, and I lifted my head to eat out Brooke's pussy. I heard the boys holler and high five each other, but I was focused on Brooke's fiery pink pussy in my face. We ate each other out for god-knows how long, and we climaxed several times. Eventually we were spent, and we lay on our sides opposite each other catching our breath.

My eyes were closed as I felt one of the boys grab my hands and the other grabbed my feet. Before I knew what was happening, they had lifted me up, and tossed me into the pool. I screamed in shock as my body hit the water. My head popped out of the water as I swore at those fuckers! I then saw Brooke try to fight off Rylan and Mark as they promptly grabbed her and tossed her right in next to me, screaming and splashing me in the face!

Brooke was also pissed as she yelled at the boys, and they suddenly cannon-balled into the water laughing. Brooke and I immediately began punching them, but they merely embraced us and eventually kissed us so much we forgot we were pissed off. We swam around for a while, and once the boys got hard again Brooke and I demanded a show from the boys.

This time it was Brooke and I with a beer in each hand as we watched Rylan and Mark make out. Rylan was underneath Mark, raking his fingertips across his back, as their hard cocks were pressed between them. Mark went down on Rylan the same way Brooke went down on me, kissing his way down until he devoured Rylan's cock. He bobbed up and down on his cock for several minutes.

"Let's see you two studs 69!" I shouted.

Happy to please, Mark swung around on his side and presented his cock to Rylan's waiting mouth. Rylan turned his body to allow Mark access to his own. On their sides, each of the boys bobbed their heads on the other as they grew to full hardness. By then the sun was going down, so the boys finished their show before they could climax.

"Alright ladies. Time to fuck," said Rylan, standing. "Get your pretty asses upstairs."

I stood a little too fast, and the beers went right to my head. Mark led an eager Brooke to the door, while Rylan slapped my ass and gave it a pinch. I hit him lightly on his arm, but unquestioningly let his fully hard cock lead the way. The four of us practically ran up the stairs to fuck the rest of the evening away.

"Alright," informed Rylan, "I think it's only fair Brooke get the attention Beth got last night. You up for a little more strap-on action, Beth?"

"Fuck yeah! Let's fuck the shit out of her!" I grinned.

"Don't let her fool you," Rylan warned, "fucking Brooke is harder than it looks. Uh, no pun intended."

"I'll be gentle," said Brooke, who was lying on the bed having her nipples sucked by Mark.

I ducked into the bathroom to retrieve the dildo in the sink. I wiped it off and dried it, and brought it into the bedroom. Brooke was on her back, with Mark on his knees eating her out. Rylan was standing next to the bed stroking his dick and watching down on them. I found the harness, and deftly pulled it on. I moved over to Rylan and stood next to him as I inserted the flared dildo into the loops and adjusted it. He continued to stroke his dick watching Brooke purr under Mark.

"You ready to fuck, dude?" Rylan asked me with his cock in his hand.