Romping on Winter Break – Day 08

tagGroup SexRomping on Winter Break – Day 08

This is the final day of Romping on Winter Break. I hope you have enjoyed the series so far. I have been considering writing stand-alone stories featuring these characters after the week has concluded, but I haven't decided yet. If you're interested in seeing more escapades with these characters, or if you have enjoyed these stories, the best way to motivate me is to comment or send me a message. I have a few ideas, but we shall see. Enjoy.
MaiaEmpire
Day 8
The phone buzzed angrily as the four of us grumbled. Rylan had set an alarm for 8 this morning, unlike the rest of the week when we woke up whenever we damn well felt like it. We had stayed wrapped up in each other's arms all night, still sticky from sweat and dried cum. Rylan reached over to slap the alarm with a groan, and rolled back to rejoin the pile of us naked corpses. None of us had gotten more than a few hours of sleep, and we lay there grumpy and unmoving, refusing to let go of each other.
Still unhappy to be disturbed from my slumber, I held my eyes shut and hugged them closer. I didn't want to move, and I felt my eyes begin watering up again. I didn't want to leave. As I mentally rejected the world around me, I could feel Rylan's cock slowly start to get stiff as it pressed against my thigh. I sighed very quietly, as Rylan slowly grinded his now hard penis against me.
I dislodged from Brooke and Mark, and slowly rolled on to my stomach. I was grumpy, depressed, and angry at everything but Rylan's cock. At that moment, it was the only thing that could possibly get me to move. I was on the verge of crying in sadness and frustration. I wanted to feel pain, to match my mood. I reached back with my hands and spread my butt cheeks.
"Fuck my ass, Rylan," I whispered into the pillow. "Fuck me raw. Make it hurt."
Rylan hesitantly spit on his hand and slicked up his cock. I buried my face into the pillow to hide my tears as he positioned his cock at the entrance of my ass. He thrust against me as my sphincter slowly loosened, and I continued sniffling into the pillow. His cockhead pushed past my ring, and despite the stretching from last night's ass fuckings, it hurt using only Rylan's spit. But I didn't care, I wanted the pain.
"Push it all the way in," I said, still sobbing into the pillow, "I don't want to feel this way, I don't want to go home. Fuck me forgetful, Rylan."
Rylan inhaled, and in one motion jammed the rest of his cock inside of me. I was in agony, and I cried out in pain. Rylan collapsed on top of me, stroking and kissing my back with his cock buried inside of my ass. It burned and ached, and I hissed and whimpered into the pillow, gripping the sheets hard with my hands.
"God, I love your cock inside of me, Rylan," I babbled, the pain still ripping through me.
Without a word, Rylan lifted himself up and began thrusting at my ass. The pain came in waves, and soon my crying stopped as the aching began to ebb. I started moaning in pleasure. I began pushing my ass against him, and in response he lifted me up to my hands and knees. I kept backing my ass up to match his thrusts, as he sped up. The sound of his thighs smacking against my hamstrings filled the room.
I rubbed my pussy as Rylan gasped and spasmed inside of my ass. His load was not large, as he had spent himself liberally the night before, but his seed dribbled somewhere deep inside my ass. He kept his spasming dick impaled inside of me, and I furiously rubbed my clit. My ass muscles clenched on his dick and I climaxed. My head fell forward onto the pillow.
Slowly, Rylan removed his cock from my ass, which stayed prone in the air. He lowered his head and began to eat out my ass as I moaned into the pillow. When he finished, he slapped my ass. I squealed in pleasure.
"Do it again, Rylan. Slap my ass."
Rylan complied, and gave an even harder slap to my butt cheek. It stung, and my entire body shuddered. I kept my ass up for more.
"Don't stop. Spank me! Please spank me!"
Once again, he wound up and let loose on my poor butt cheek. He didn't wait for me to ask for more; he landed a few more blows to my behind until it became too much and I collapsed. My ass was burning, and I was shaking uncontrollably. Rylan laid himself next to me and put his arm around me, and I laid on my stomach.
Next to us, Brooke and Mark had been making love to each other, making a lot less noise than us. Mark was on top of Brooke getting ready to finish inside of her as she kept her legs high in the air. He grunted, Brooke gasped, and he collapsed on top of her. As Brooke held him, she gave me a sympathetic smile.
Mark rolled off of Brooke, and she reached over to stroke my red and sore bottom. "It's okay, hun. Get it out of your system."
I looked at her, Rylan still stroking my back, and nodded. The rough fuck he had given me had loosened up the knots in my brain, and I was ready to get up. Well, mentally ready. My ass still burned, and I needed a few minutes before I was able to walk. Mark stood up and headed into the bathroom, and Rylan got up to follow him.
"Take a sec, girls. Mark and I will wash up first, and head downstairs to start removing some of our…evidence. Don't worry too much about cleaning, the staff's coming this afternoon to prepare the house for when my parents return. Just…try and make it look as if we haven't been fucking for the past week?" Rylan shrugged.
Brooke and I laughed a little, and Rylan pinched my nose with a smile. He joined Mark, who had started showering, and closed the door behind him. Brooke pulled me onto my side, and wrapped her arms around me. While Brooke spooned me, her entire body pressed against mine. I felt her breasts pressed against my back as she hugged me close. She left light kisses on the back of my neck and shoulder as I recovered from my anal assault.
"Just relax, Beth," she whispered between kisses, "just lay still, my sweet baby."
"Oh, Brooke," I responded, "please don't stop holding me."
"Never, Beth. Never. Remember, this isn't the end; this is just the beginning. After this week, we'll be able to make love all the time."
"I know," I whispered distantly. I rolled over so that I was facing her, her leg draping over mine and our nipples touching. We stared into each others' eyes as I stroked her hair behind her ear.
I brought my voice low. "I love you, Brooke."
Brooke smiled at me. "I love you too, sweetie."
I shook my head. "No, Brooke," I whispered, "I…think I'm in love with you. Like, in love with you." My heart pounded in my chest.
Brooke looked at me, her eyes tearing up ever so slightly. She bit her bottom lip. "Beth. My sweet Beth. I'm in love with you, too. I think I've always been in love with you."
I stroked her cheek, and gave a small frown. "But I'm in love with Rylan, too. I love being his girlfriend and I love how focused and assured he is. I mean, I guess I've only really been with him this week…"
"Sweetie, sweetie, I know how you feel. I have the same issue. I'm in love with you, but I'm also in love with Mark, the big goof-ball." She chuckled. "But you're right, we've been with the boys for a few months, but I've known you since forever. It feels different, somehow."
"It's like, not better or worse," I said, finishing her thought. "Just different. Deeper, maybe, because we've known each other so long."
"Exactly," said Brooke. There was a pause as we continued to stroke each other. "That said, I still want to be Mark's girlfriend when we get back to school. But, and I know this is weird, I want to be your girlfriend, too. Even if it's not something we don't tell anyone."
"Really? We should be…girlfriends?"
"We'd still be dating the boys. And they're totally okay with us being together. No one else needs to know; this would be between us. We can still hang out like we always have, except now we'll have sex afterwards!"
I giggled at that. "Is it weird to be in love with two people at the same time, and for them to be completely okay with it? And not only that, to actively fuck the hell out of each other?"
"Yes," replied Brooke. "Yes, it is. It is incredibly strange to be in this situation." Her hands explored my thigh. "But it feels so good."
I grinned at her. "So I guess I've got myself a boyfriend and a girlfriend." I shook my head. "Geezus, I have a girlfriend. I can't believe it!"
"Yes. Yes you do!" She peppered my face with kisses. "I'm your girlfriend now!" We giggled uncontrollably. "And as your super-cool girlfriend," she continued, "I will allow you to get as much side dick as you'd like!"
"And side pussy, too?" I blurted out.
Brooke blinked, and stared at me. "You would want to fuck another girl?"
I dumbly sputtered, "I'm sorry, I don't know why I said that…"
"…I mean, that would actually be really hot."
My heart stopped. "Wait, what?"
"I said that would be really hot," she replied. "You're only the second girl I've had sex with, and after this week I just want to fuck as many girls as possible."
"Oh my god, are you serious?"
"Of course I'm serious! And I'd love to watch you fuck another girl. Would you want to?"
I suddenly had a case of butterflies. I hadn't considered having sex with a girl besides Brooke, just like I hadn't considered ever having sex with any girl before this week! But now, my beautiful, sexy, girlfriend (god, it was thrilling to say that) suggested it like it was the most natural thing in the world.
"Yeah," I said with some difficulty, "yeah, I think I would. Oh my god, yes, I totally want to!"
"Maybe we could scope out one of the girls on the squad? We could talk them into a threesome thing," suggested Brooke.
"I think Sophia might be interested. She's so pretty. Or maybe Alex, she's kind of a flirt. And I love her butt!"
"God, Beth, a foursome with them! Could you imagine that?"
"Geez, what are we doing?!" I exclaimed. "We're laying here naked, as girlfriends, and talking about fucking even more girls! I can't believe this is me!"
"Does this mean," Brooke pried, "that you'll be checking the box labelled 'bisexual'?"
I rolled my eyes and shrugged. "You know what, screw it. If this means that I'm bisexual, then I'm bisexual. I'm totally fucking bi! Now get over and kiss me, my beautiful girlfriend."
Our lips met as Brooke, my girlfriend Brooke, gave me the most passionate kiss she had given me this week. We melted into each other, our tits crushed against each other and our legs entangled. I vaguely heard the boys pile out of the bathroom and heard them chuckle and high-five each other as they watched their girlfriends make out. We continued to kiss as they headed to the door.
"Not too long, ladies," called Rylan. "We gotta be ready to go in less than two hours!" He stepped into the hallway and closed the door behind him.
We didn't spend too long kissing each other, but we eventually broke our kiss and nodded to each other. Time to behave, we wordlessly decided together. My bum had recovered a little; the red slap-marks were fading and my asshole only burned a little. I was getting better at taking cock up my ass. Practice makes perfect, I suppose. And I had had plenty of practice this week.
Brooke went into the bathroom first, but I thought it was only fair that I took care of Rylan's sister's strap-on. I stepped off the bed and immediately winced. A sharp pain shot through my ass. "Easy does it," I thought to myself as I hobbled to the foot of the bed holding my bum. I found the dildo and harness on the floor at the foot of the bed, smelling like pussy and ass. I bent over and picked it up, feeling a strain and a little moisture inside of my ass. I waddled into the bathroom.
Brooke was casually sitting on the toilet with her legs together, completely at ease with peeing in front of me. When she saw me stumble to the sink to toss in the strap-on, gripping my still-tender bottom, she interrupted me.
"Oh, honey, no no no." She quickly grabbed toilet paper, wiped her pussy, and stood to take the dildo from me as I leaned against the counter with my hand on my hip and my legs bowed. "Beth, sit down on the toilet and let me wash that thing."
"No, I'm okay, I'm fine…"
"Beth, listen to your girlfriend!" I knew immediately that I would be hearing that line for a while. "You're probably got a gallon of cum in your pussy," she continued lecturing, "and I know you got a little too rough with the assplay just now. Now get on that toilet, and I don't want to hear you complain about peeing in front of me!"
"Yes, dear," I scoffed as I stumbled to the toilet and plopped down. I involuntarily started tinkling, and I rested my elbows on my lap and lowered my head. Brooke started rinsing and scrubbing the dildo, and I grunted and pushed out the cum in my pussy and ass as best I could. Thankfully, only a few lady farts exited my colon. They did take off a little bit of the pressure inside of me. Brooke set the dildo on its base pointed up to dry, and stepped into the shower and turned the dial.
I went for a piece of toilet paper. "Hold on, I'll get in there with you."
Brooke wagged her finger at me. "Oh no, you don't, missie. No more sex today! The car's going to be here soon. I'm hosing off and then you're doing the same!
"Great," I moaned, "the second I get a girlfriend, she immediately stops having sex with me."
"Sucks to be you, babe. I know you're not finished on that seat, make sure you push out as much air out of your ass as possible!"
I threw an empty toilet roll at her. "Geezus, take your shower already!" I didn't care if she was my girlfriend, I still wasn't fond of peeing in front of her. She stuck out her tongue and stepped in, and I continued grunting and pushing out my ass. Brooke was eventually proven right, as I had one fart left in me, and when it let loose, Brooke applauded from the shower stall. I covered my face with my palm in embarrassment, but my ass did feel a lot better. Brooke finished her shower, and dried herself off. She gave me a smooch on my cheek.
"I'll see you downstairs, girlfriend." She flashed her playful smile, and walked out the door.
I loved her so much. My girlfriend. My best friend since middle school was my girlfriend. It felt crazy, but it felt right. I took a shower of my own without much excitement, and after toweling off I appraised the dildo, poking up at the ceiling.
I took the pink dildo and white belt into my hands and inspected it. It was as clean as it was when I stole it from Rylan's sister's room a few days ago. I wiped it off one last time, and carried it into the hallway and into her room. The bottom drawer full of panties where I originally discovered it was still open. I crouched in front of it as I appraised the strap-on and smiled. I promised myself I would get one of my own, to fuck Brooke or Rylan. Hell, maybe even Mark or some random girl someday. I kissed the cock head and solemnly stuffed it in her drawer and closed it.
I joined everyone downstairs, where Rylan had made a pot of coffee and some toast. Brooke and Mark were whispering to each other and laughing, so I went to my naked boy who was leaning against the counter smiling at me. He embraced me and held me tight against him. He smelled so clean and I felt safe with his arms around me, and he pulled me into a kiss. He held me against him as he pulled off my lips to look me in the eyes.
"Are you okay, Beth? You took it a little rough back there."
He was such a sweetheart as he stared at me with worried eyes. "I'm fine, babe. You felt so good and fucked me just the way I needed."
"Beth, I love you. I know it's only been a week, but I've never felt this way about a girl before. Whatever you're into, I'm into." He kept staring at me with his beautiful blue eyes.
I smirked at him. "You know, you're going to have to share me with Beth. We decided to be girlfriends, even if it's a secret. I'm not sure how I ended up getting a boyfriend and a girlfriend this week, but here we are!"
"I know how close you two are. It makes sense. I want you two to mess around with each other, it's fucking hot!"
"Are you just saying that so you can keep fucking Mark?" I teased.
"Well," Rylan said, "that's not the main reason…but yeah, I'd like to keep fucking Mark! And you can keep fooling around with Brooke."
"And maybe some other girls."
He paused. "Uh, come again?"
"Well, I might have discussed playing with a few other girls with Brooke. You know, if they were interested."
"Damn," said Rylan, his eyes wide open. "So you're…"
"Bisexual, I guess. I mean, call a spade a spade. I want to have sex with guys, and I want to have sex with girls. I never thought about fucking a girl before, but this week has really opened up some possibilities. It's worth exploring, you know?"
"Well, welcome to the Bi-Club," smiled Rylan. "And if you're going to chase girls, maybe I should chase some guys…"
"You know, babe, you totally should. You shouldn't be afraid to just experiment. You need to explore your bi-side, too. Plus, I wouldn't mind watching!" I laughed.
"I think I just got the perfect girlfriend," said Rylan.
"I think I just got the perfect boyfriend," I replied, kissing Rylan. I gave him a smirk. "And the perfect girlfriend!"
Rylan chuckled and gave me a big, long hug. I think he was trying to squeeze the life out of me. Brooke was leaning against Mark with his shoulder around her, and they both grinned at us. Rylan and I grabbed a cup of coffee and smeared some toast, as we all sat around the breakfast table. We chatted and laughed, until Rylan's phone went off once again. He answered it.
"Hello, Charles. Yes Charles. No, that's fine. About 30 minutes away? Uh…excellent. Please wait outside until we come out.
Rylan glumly turned off his phone, and the four of us collectively sighed. We were all reminded that we were sitting around completely nude and that it was time to face the real world. None of us were looking forward to putting clothes on. It was way too much fun romping around naked. We broke four ways around the house to find our stray belongings and clothes and bring them to our bags, which we hauled down to the foyer.
We dug into our bags on the marble entryway floor, tossing our stuff into the bags and pulling out our respective clothes. Rylan did a last-minute run around to make sure it wasn't totally obvious that we had been screwing all over the place. I slipped on a pair of panties and matching bra, and pulled on a pair of jeans and a sweater. It felt way too itchy. I immediately missed being a nudist.
Mark was pulling on his pants, and Brooke was buttoning her pink blouse. Neither looked very pleased. I gathered my hair into a quick ponytail with a hair tie. Not very cute, but I figured it would do for now. Rylan, satisfied he found every shred of evidence of our fornication, waltzed in naked and went for his own bag. I took one last glance at Rylan's amazing ass as he pulled his Tommy Hilfiger boxer briefs over it.
"Bye bye, beautiful bum," I thought to myself.
The second Rylan tossed on his coat, his phone buzzed as Charles announced he had arrived outside. Rylan opened the door as his chauffeur Charles entered in his uniform. The rest of us shifted uncomfortably in our clothes.
"Good afternoon, Master Rylan. Did you have an enjoyable week?"
Rylan nodded. "Very much so, Charles. Please load our bags into the car, and let the staff know that the house is ready for them."
"Very good, sir." Charles started to carry the bags into the limo, as Rylan put his hand around my waist and gave me a little hug. I smiled up at him, wishing I could rip our clothes off, drag him upstairs, and fuck his brains out. But it was not to be. For one thing, Rylan had already removed the sheets. We stepped outside into the cold and made our way to the black sedan, with Charles opening the door for us.

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