Romping on Winter Break - Day 02

Writer's Note:

Here is the revised Chapter 2 of Romping on Winter Break. I have changed almost all of the actions from the original story that inspired this, and I'm very happy with how it came out. If you like it, please leave a comment or send a message. Any constructive criticism is welcome.

MaiaEmpire

***

I awoke the next morning on my side feeling the warm sheets underneath me. Brooke's naked body lay sprawled next to my own. She had rolled on her back, her legs splayed out and her breasts lifting softly as she breathed. I could feel Rylan curled up against my back; apparently he had crawled over in the night to spoon me.

Last night's activities flashed in my head, and images of the boys having sex with each other and me having sex with Brooke hit me one by one. I couldn't believe it had happened, yet here I was, naked and laying next to Brooke, with Rylan holding me. It felt wonderful, and in a weird way liberating. I had only had sex with a couple of guys before, and in one night I had doubled my sex partners. And one was a girl!

Although Rylan felt amazing with his soft dick between my butt cheeks and his chest was pressed against my back, I kept staring at Brooke's sleeping frame. She had such nice curves; just like me, but a little smaller. Slightly athletic, but slim like a dancer. I thought about how she went down on me last night, and started thinking that she perhaps deserved the same attention she gave me.

I gently lifted Rylan's arm off of me, and quietly slid down Brooke's body. I got on my knees between Brooke's legs, and stared at her pussy only a foot away from my face. I licked my lips. Was I really doing this?! I had no idea how to go down on a girl, but I was determined to make her cum like she had for me.

I inched forward, the scent of her womanhood hitting my nostrils. She was musky, and a little sweaty. I tried to do what I thought felt good. I began by simply kissing her pussy lips a few times. Then, I stuck out my tongue and traced her pussy lips, going up and down slowly. She stirred ever so slightly. I found the crest of her labia, and flicked it with the tip of my tongue. I heard Brooke sigh. Bingo.

I kissed her clit, and slowly began to suck it with my lips. I could feel it begin to harden as I worked it. Brooke's breathing became heavier, and I felt her hand go to the top of my head. I looked up at her face, past her mound, and our eyes met. I never stopped sucking her clit. She smiled at me, and I felt her grip my hair in her hand as I refocused on eating her out.

I licked downwards, my tongue entering her flared pussy, and I tasted her cum as it flowed out of her. It was yummy. I began to lap it up, alternating from her clit, and back to her vagina. Her hips gyrated against me as she held my head against her pussy.

I took my finger and in one movement inserted it into her leaking pussy. She let out a loud groan, and she began to hump back faster against me. I attacked her pussy, the wet sounds of my fingers slapping against her, and I felt her contract against me. She moaned, and I felt her burst into orgasm.

I didn't relent, and the combination of sucking her clit and finger-fucking her pussy had her release two more times into my wanting mouth. I licked every drop. Soon she couldn't take it anymore, and quickly gripped my hair and dragged me up to her mouth. She kissed me hard, her tongue jamming into my mouth and I knew she could taste herself.

We kissed for an eternity, our breasts pressed against each other and her legs wrapped around me. It was so weird to feel a pussy instead of a dick against my groin, but the smoothness and softness of her body was heavenly. Kissing a girl like this, with my naked body on hers, was exhilarating.

I lifted off of her face to look her in the eyes, and together we turned to see the boys watching us. Mark was behind Rylan on his side, and they were both actively stroking their dicks to the sight of us girls making love to each other. My cheek pressed against Brooke's as we smiled at them.

"Well, boys?" I asked them teasingly, "enjoy watching your girlfriends do each other?"

"Brooke," stammered Mark, "I need to see you in the bathroom. Now."

Mark practically jumped off the bed and Brooke shoved me off of her. She leapt on her feet, and dashed into the bathroom after Mark, slamming it behind her. I heard something crash, and then various muffled noises from the two of them. I was left alone with Rylan, and we shared a collective chuckle as I curled up against him. He continued to stroke his cock.

"So Beth, what did you think of eating out a girl?"

"It was...highly interesting!" I managed to get out. "I'm definitely going to have to do it a few more times his week!"

"Same here," replied Rylan, pulling me up for a kiss.

I returned to the crook of his arm. "I have to say, it's not nearly as intense as watching Mark fuck you in the ass. Doesn't that hurt?!"

Rylan shrugged. "Yeah, it does at first. Takes a second to get used to it. But once it starts, it's freaking incredible. And the more often you do it, the easier it gets."

"Really? I always thought it was just painful."

"It is, but that's why it's so hot. It's like, an athletic soreness. It feels good because it hurts." Rylan lifted up onto his elbows and looked down at me. "Have you ever wanted to try it?"

I felt a nervous twitch in my stomach. "I've never thought about it," I whispered.

"Do you...want to try it?"

I looked at him cross-eyed, bemused. "So a day after getting into my pussy, you're already trying to get into my ass?"

He smirked back at me. "Is that a no?"

I laid back down, staring at the ceiling in thought. My pussy twitched a little as I considered it. Considering how much I had done for the first time in the last 24 hours or so, why not add another thing to the list? After all, Rylan seems to really enjoy getting fucked in the ass, and I had to admit I was definitely curious.

"Would you be gentle?" I asked, softy.

Rylan took my face into his hands and kissed me, making my apprehension melt. "Of course, Beth. I've done this loads of times. I'll take it really slow. Get onto your knees."

I did as Rylan told me, as he reached over to the nightstand and grabbed the bottle of lube. He spread it all over his thick cock, which by now was standing at full attention. I stared at it as I knelt on all fours, my prone ass sticking out. I gulped as I thought about his dick being inside of my ass. Was it my imagination, or did it look even thicker than it did the day before?

Ryland got behind me, and began to smear some lube on my asshole. I shivered as his finger grazed my anus. I was beginning to get incredibly anxious, and I think Rylan sensed it.

"Relax, Beth," Rylan reassured me. "I'm going to take it really slow. If it hurts, tell me and I can slow down. I'm going to start with my fingers, alright?"

I nodded, as Rylan's calm voice took the edge off. I took a deep breath through my nose, and I felt a finger slide into my asshole for the first time. It smarted for a moment, but my ass relaxed and accepted it. I felt a warm sensation spread inside of me. He slid it in and out several times, as I continued to hold my breath.

He then pulled all the way out, and pushed in again, this time with two fingers. I squealed through my nose, but kept focusing on accepting his fingers. Rylan started pumping his fingers faster as I pushed through the pain.

"Are you okay, Beth?"

"Mmm-hmmm," was all I could get out as I nodded vigorously.

"Alright. Here's finger number three."

Not waiting for a response, he pulled out his fingers and jammed in a third digit. I let out a moan of pain, and gripped the sheets with my hands. I couldn't stop gasping for air. Rylan kept his three fingers unmoving inside of me, all the way to the knuckle. Slowly, I felt the pain ebb as my asshole stretched to accommodate his fingers.

He slowly began to fuck me with his fingers, and my eyes were shut as tightly as they could. I gasped and sputtered, but Rylan expertly kept the same pace and soon I felt like I was ready for the next step. As painful as it was, Rylan was right; the pain somehow made it feel good.

"(Huff)...(pant)...Rylan...I think...(oof)...I'm ready..."

Rylan got to his knees behind me, his fingers never leaving my ass. I felt his cockhead poke against my butt crack. I was light-headed as I considered what I was about to happen. I was going to get fucked in the ass! What was I doing?!

Rylan's fingers slid out, and I felt his cock push against my anus. It felt so much thicker than his fingers. He thrust against me a few times, and it didn't feel like it could possibly fit. I was about to call it right there, when suddenly his head entered my ass with a pop. A sharp pain shot through my ass, and I yelped.

"Uuggghhh..."

Rylan held his cock still for a moment as the pain subsided, and I felt him slowly push forward, millimeter by millimeter. I was hyperventilating at this point, but I didn't dare tell him to stop. I was determined to get him all the way inside me, despite the pain. Rylan steadily and inexorably kept pushing forward, as my ass stretched to take him.

Soon, I felt his pubes scratch my butt cheeks and his thighs against my hamstrings. He had done it; I had Rylan's cock all the way inside of my ass. I was squealing and panting, and Rylan held still against me.

"I'm gonna hold it right here, Beth. Just get used to the fullness inside of your ass. I'm not going to start fucking until you're ready."

I nodded, biting my lower lip in pain as I struggled to get used to his cock. Rylan didn't move, and I stayed still on my knees. My eyes started to water and I focused on breathing. As I tried to relax, Mark and Brooke exited the bathroom. They were flushed and smiling from whatever they were up to, and gasped when they saw me in my...compromised position.

My mouth was agape as I looked at Brooke. I was still shuddering in spurts of pain. She gave me a sympathetic smile, a knowing nod, and took Mark's hand to drag him out of the bedroom. He was locked onto my cock-filled ass as Brooke dragged him out into the hallway, giving us some privacy.

Minutes passed with Rylan keeping absolutely still, and the pain had almost completely gone away. Though there was still some pain, it felt good; wonderful even. The warmness had spread throughout my entire pelvis, and my pussy was completely wet. I finally felt like I was ready.

"Alright, Rylan. I'm...oof...ready for the fucking to begin," I said as sexily as I possibly could.

"Okay, here we go." With that, Rylan pulled out and pushed in, taking my breath away. He slowly thrust a few more times, each one making me gasp loudly. I felt tears stream to my cheeks and I began to whimper, but I didn't tell him to stop. It felt so different than getting fucked in the pussy. It hurt, but for some reason the idea that I was getting fucked in the ass was so thrilling, and handling the pain made me feel somewhat tough.

Rylan began to pump faster, and as the friction increased in my ass, my whimpers started to become moans. I felt his thighs slam against my hamstrings, and the slap of skin against my butt cheeks. I reached down to my leaking pussy and began to rub it as Rylan pounded my ass. I jammed my fingers into my pussy and began to fuck myself, wishing somehow that Rylan could also fuck my pussy as he fucked my ass. His cock in my ass seemed to amplify the sensation on my clit, and soon I was cumming.

Rylan was banging me hard now. "I'm almost there, babe. Fuck...your ass is so tight..."

"Oh god, Rylan, cum in my ass!" I yelled incoherantly, "Don't stop fucking me! Oh my god, keep fucking my ass!"

With a shout, Rylan shuddered and jammed his cock all the way inside of me, and I could feel it pulse. I could feel his load shoot somewhere deep inside of my ass. Rylan held my hips fast and continued to shoot inside of me. My arms gave out, and I collapsed on the bed in front of me, dragging Rylan on top of me. His cock stayed still in my ass as he rested on my back, as the final shots of cum leaked inside of me.

He lay on top of me while I recovered. I wanted to keep his cock inside of me as long as I could, even though I couldn't move at all. Soon, it began to soften and it slipped out of my ass. I gasped as it exited, and I could feel Rylan's cum leak out of my abused ass. Without a word, Rylan slithered down my legs and he began to lick my asshole. My head shot up in a silent scream as I felt his tongue clean me out. I wasn't expecting him to do this, but it felt amazing.

Once he finished, he took me into his arms and held me. He kissed me several times, and I could taste the cum on his tongue.

"So, what did you think?" he asked me.

"Oh my god, Rylan, you were right. It hurt so much...but it felt so fucking good." I wiped away sweat from my forehead. "I can't believe I just had anal sex!"

"I know, right? You're a fucking trooper. Come on, let's jump in the shower and get you cleaned up."

I smirked at him. "Didn't you just finish cleaning me up?"

He chuckled. "True, but you still smell like sweat and cum. Not that I'm complaining!"

I smiled at him. "Look at you, you've relaxed a lot since yesterday!"

"Who knew," joked Rylan, "that all it would take to loosen up is to get your ass fucked in front of your girlfriend?"

I smiled. "Girlfriend, huh? I like the sound of that."

Rylan kissed me one more time, and helped me to my feet. I was still very wobbly, and once I was on my feet my ass immediately shot in pain. I winced, but Rylan helped me to the bathroom. He turned on the shower, and the two of us piled in. We took turns washing each other, taking special care of both of our freshly fucked assholes. Even after we had soaped ourselves up and washed our hair, we stayed in the shower just holding each other and kissing. I loved feeling Rylan's smooth, wet body against my own.

After a good long while we climbed out of the shower and dried each other off. We couldn't help giving quick pecks to each other as we rubbed each other down with the towel. Once I was dry, I automatically wrapped the towel around my torso. But Rylan, standing completely nude with his hands on his hips, raised his eyebrow with a quizzical smirk. I snorted a laugh, and tossed the towel aside.

"Right, we're going nude for the week!" I announced.

"Hey, I'm still getting used to it myself," replied Rylan. "Let's head down and see what we can do for breakfast."

"Probably more like lunch at this point."

"Well, we had important ass-fucking to attend to! C'mon, I'll make you an omelet or something."

Rylan took my hand in his, and we stepped through the bedroom and into the hallway. Both of us completely naked, we went down the marble stairs and made our way towards the kitchen. We could hear slapping sounds from the hall, and the first thing we saw as we entered was Brooke leaning against the kitchen island and Mark fucking into her from behind. Brooke stood up tall with her arms straight on the counter and her boobs sticking forward as Mark couched down to hammer into her.

Brooke sucked in her lip. "Don't...oof...mind us," she said between breaths, "I think...uph...we're almost finished here."

Rylan and I laughed as I sat on one of the island stools to watch and Rylan dug into the fridge to take out the eggs and cheese. Mark kept banging into Brooke, who by now had her eyes closed to focus on her fucking, until finally Mark slammed into Brooke, feeding her all of his cock, and I knew that he was cumming inside of her. Brooke licked her lips and rotated her hips against him, taking his load. I rubbed my pussy a little as I watched, while Rylan turned on the burners and cracked eggs into a bowl.

Mark pulled out of Brooke, who turned around and leaned against the counter on her elbows. She spread her legs as Mark got down on his knees to suck her pussy. I guess both of the boys enjoyed the taste of their own cum. I vaguely wished that I could clean out Brooke's pussy of Mark's cum, but I was happy to watch him go to town.

Once he was finished, Mark stood in front of Brooke and jammed his tongue into her mouth. I saw his hand reach down to grip her ass. Brooke just as hungrily frenched him back, and she obviously could taste both herself and Mark's cum. They separated, and smiled at each other. Brooke dislodged from Mark to sit next to me, while Mark started chatting up Rylan on the other side of the kitchen as he poured egg batter into the pan.

"So Beth," whispered Brooke, "how is your ass feeling?"

I smirked at her. "It's a little tender, but good!"

"How did it feel? The butt sex, I mean. Did it hurt you?"

"Well, yes," I said, "but once I relaxed it felt amazing. And I guess since you've already out-sexed me by announcing you had had lesbian sex, I guess by doing anal first I'm one up on you now!"

"Actually," said Brooke nonchalantly, "Mark's been fucking my ass for about a month now."

"Wha-a-at?!"

"Well yeah," said Brooke. "Back in November we got hot and heavy one night, but I was on my period. But I still wanted to fuck, and Mark talked me into anal. That's how I found out about him and Rylan. He told me how good sex with Rylan felt, and picturing the two of them screwing was all it took to convince me!"

"Well, I stand amazed. And you've still been doing it?"

"Only a couple of times since then. It turns out, I'm kind of an ass slut!" laughed Brooke.

"Well, we might have that in common now," I said laughing with her. "It wasn't better than getting fucked in the pussy. Just way, way different. More intense, I guess." I placed my hand on her naked thigh. "I guess I'll have to find some other way to out-sex you!"

"Bring it on!" Brooke challenged, as she leaned in to kiss me. I felt her tongue go into my mouth, and I returned the affection.

"So ladies," called Rylan, "as much as I love seeing you two kiss, I would like to know what kind of omelet you'd like!"

Rylan took our orders and prepared omelets for the four of us, while we sat around the island talking and joking. It was so sexy standing around naked with each other. I have to admit while at first it was awkward and embarrassing for me, it was far more comfortable walking around with no clothes on. And I think we were all quickly getting used to it to the point we were starting to not notice our nudity. Of course, I still enjoyed sneaking peeks at the boys' penises. Not to mention Brooke's boobs and bum.

We ate our eggs at the breakfast table, and as usual Rylan did an amazing job. He must have some secret technique or something. Or maybe it was the cheese he used. When we finished, Brooke and I offered to clean up, since Rylan cooked.

"Thanks girls," said Rylan, standing. "I'm gonna go into the den and play a little PS4 and chill a bit."

"I'll come with!" interjected Mark, standing up with Rylan.

"Hold on," I shot at him, "you didn't help cook!" But by the time I finished the sentence Mark had bounded out the door after Rylan.

"Pfft, boys," Brooke muttered.

"Agreed," I replied. "Well, let's clean up. I'll start with the pans if you can clear the table."

"Sounds good to me," nodded Brooke. "And since the boys abandoned us for video games, how about you and I work on our fake Florida tans by the pool?"

"That's a good idea. Hopefully there's not too much snow on the atrium glass and we can get some good sunlight."

"You know," said Brooke slyly, "I've never sunbathed nude before!"

"Same here," I replied, as I began soaping up the pan in the sink. "No tan lines for us! Can't wait!"

Brooke cleared the table and we finished doing the dishes side by side. I washed, and she dried. We laughed and hip-checked each other as we worked, and Brooke managed to pinch my butt a few times! When we finished, Brooke needed to use the bathroom and get some things from her bag, and while she ran upstairs I decided to peek in on the boys. I heard the TV on in one of the side rooms, and peeked in from the hall.