Romping on Winter Break - Day 01

"Oh god, Rylan, keep doing that. Right there. Yes. Yes! Oh god!"

I climaxed right there, and I felt Rylan taste and lap up my cum. Once he had finished, he stood up to remove his pants. I licked my lips as he pulled them off, and I saw his cock released. It wasn't super long, but it did look rather thick. I knew it was going to feel good inside of me.

"Lay on top of me Rylan. I want you inside me so bad."

Rylan simply nodded, and mounted me. I raised my knees and spread my legs as I felt Rylan's thick cock press against my mound. His smooth chest pressed against my boobs, and we attacked each others' mouths once again. Rylan's hips began to thrust against me, and I adjusted so that his head was pushed against my pussy lips.

"Enter me, baby. I want you inside of me," I begged him.

Rylan held his breath as his dick began to spread my pussy lips, and he started to fill me. I squealed in delight. God, it had been so long since I was fucked by someone. My eyes closed and my mouth was open wide as Rylan sank all the way inside of me, his light pubes pressed against my own. He held still as I got used to him.

I opened my eyes to see him looking down at me. I grabbed him by the hair and pulled him down to kiss me as Rylan began to fuck me. He tried to get a rhythm, testing how far he could go, and to his credit he only flopped out twice. But I loved when he pushed back into me with one thrust. Now comfortable, he started to fuck me faster as I felt my orgasm building again. I groaned and moaned as Rylan took control of the fucking motion. He was a fast learner. Rylan's thrusts finally ignited my second climax, and I spasmed underneath him with a wail.

"Fuck, Beth, I'm getting close," said Rylan between breaths.

"Do it, babe. Keep fucking me. I want you to cum inside of me. Don't stop!"

With a grunt and a gasp, I felt Rylan explode inside of me. His cock spasmed and pumped me full of his load. It felt so warm and thick, and I clutched him tightly with my arms and knees as he finished cumming. He stopped moving on top of me, catching his breath, as I continued to hold him.

Eventually, his cock grew soft and slipped out of me with a pop. Rylan rolled on his side next to me, and I felt his cum leak out of me. It was so incredible to take Rylan's load. I had never done that before, but I wanted to feel Ryan inside of me and to feel him inside of me again. Rylan looked at me as he lay on his side, stroking his now limp dick.

"How was that, Beth?" he asked. He was a little apprehensive.

I turned on my side to face him. "Rylan, you were amazing. You felt so good." I smirked at him. "How did you like fucking a girl?"

"It was definitely different." I raised my eyebrow at his comment, and hIs eyes shot wide "I mean, it felt awesome! You are so beautiful, Beth. I can't believe we just had sex!" He laughed.

I giggled with him, still wondering about his earlier comment. "Yes, yes we did. Do you feel less awkward now?"

"You know, I actually do. I've wanted to get closer to you for a while now, but I'm just so bad at talking to girls. I mean, you're so smart and funny, I didn't want to screw it up."

"Rylan, if you can fuck me like that, I will forgive any screw-ups you throw at me." We laughed together, and kissed again. "Maybe it's best that we just get the sex out of the way first so we can just relax and have fun this week!"

"I couldn't agree more, Beth." I curled up next to him as he lay on his back, running my finger over his chest and abs. We spent several minutes simply holding each other and catching our breath. Eventually, Rylan stretched and sat up. I joined him, and gathered my knees to my chest.

"We should probably get dressed and find Mark and Brooke," suggested Rylan.

"Aw, you don't want to stay naked? Boo."

"Probably not the best idea to flash those guys. We can just put on our swimsuits. It's almost naked."

"I suppose. I do have a cute two-piece, but it's probably tame considering I'm sitting here naked," I joked.

"And freshly fucked!" Rylan chuckled and dismounted the bed. His butt stuck out adorably as he reached down to pick up his discarded clothes. He most definitely had a nice ass. I popped open my bag to dig out my pink bikini, and ducked into the bathroom to slip it on. No sense in ruining the magic by having him watch me haphazardly tuck my boobs into the cups. Plus, I had to pee something fierce.

I returned to the bedroom, to see Rylan in his blue swim trunks and a towel over his shoulder. I posed in my bikini and tossed him a sexy look.

"You like?"

"Very much so. Though I have to admit I'm looking forward to taking it off later."

"Definitely," I cooed as he scooped me up for a kiss. We headed into the hallway and down the stairs to search for Brooke and Mark. They probably were already in the pool horsing around, so we went straight through the kitchen and into the patio area. We found them immediately, and gasped. They were definitely horsing around, and then some.

The first thing I saw was Brooke, completely naked, riding Mark as he lay on his back and gripped her hips, fucking into her. Mark had an incredible body, with a little more hair on his chest and more muscles than Rylan, but my eyes locked on Brooke as she pounded up and down on Mark's cock, with her eyes shut tight.

I had seen Brooke naked plenty of times, but seeing her actively fucking and building toward orgasm made it utterly different. She was a bit petite, save that she had a more than modest pair of boobs that flailed wildly as she rode Mark. She was also toned from being a cheerleader, and her skin was blissfully light all the way down to her toes. I couldn't stop staring at her; she was stunningly beautiful. Rylan was also staring at the two of them wide-eyed.

Brooke moaned loudly, as her orgasm escaped her. Mark too groaned, and suddenly shot his hips up into her and I knew he was cumming inside of her. She whimpered and wailed, until she finally stopped moving and steadied her hands on Mark's chest, catching her breath. She opened her eyes, her thick long hair tousled, and saw Rylan and I gaping. With Mark's cock still buried inside of her, she gave us that sweet, innocent smile.

"Mark, babe, we have an audience."

Mark lifted off the chair and turned his head to see us. "Hey guys, I hope you don't mind, but me and Brooke got a little too eager. I know you don't mind, dude!" He grinned at Rylan.

"Actually," started Rylan, "you could say that Beth and I were...similarly engaged upstairs!"

Brooke clapped her hands together. "Oh my god, you guys, it's about time!" She continued to sit on Mark's cock.

"Hell yeah, buddy. See, I told you Beth was in to you!"

Rylan shifted embarrassedly, but put his hand around my waist. "Alright, I'll give you props. You were right. Just had to...get the sex out of the way and out of my head!"

I was still staring at Brooke, happily splayed on top of Mark. "Oh, right, out of my head," was all I got out.

"So guys, what to do - ohh, oooohh," sputtered Brooke, as she pulled out and off of Mark's cock. Her pussy glistened with cum. "Mmm...sorry about that. So what do you want to do now?"

"Well," I said, still trying to look away from Brooke's naked body. "We were thinking of doing a little swimming."

"Sounds good to me! Here I go!" said Brooke, who stood up and dashed into the pool completely naked.

"You guys can put on -" I started, but Mark jumped in after Brooke with a shout of his own.

"- your suits on," I finished lamely.

Brooke and Mark laughed at us and splashed around. "C'mon guys," said Mark, "we've got this place to ourselves! You've already seen us naked, now it's your turn!"

Rylan and I looked at each other and shrugged. "Why the hell not?" we said wordlessly to each other, as Rylan slipped his trunks to his ankles. I was slightly disappointed my new swimsuit wouldn't get to be shown off, but I suppose I would get to show off everything else. It was also exciting because I had never been skinny-dipping before. I took a breath, and undid the hook in the back of my top to release the girls, and slid the bikini bottom all the way down. Brooke and Mark clapped and cheered as Rylan and I stood naked and feeling a bit silly. Rylan grabbed my hand and together we leaped into the pool.

We frolicked around the pool for some time, and I have to admit it was really fun! I poked and pinched Rylan, and even received a pinch on the bottom from Brooke! I wrestled her a little bit while the boys watched, and felt my boobs rub against hers. I released her, slightly embarrassed, but she didn't seem to notice.

"Oh, shit, I gotta check my phone for a sec," said Mark suddenly.

He got to the edge of the pool and lifted himself out, water streaming down his back. His cock hung as he stepped out of the pool, and I noticed Rylan transfixed on it. He stopped swimming and openly stared as Mark went into the kitchen to grab his phone.

"Uh, Rylan?" I asked, who was still staring.

Brooke swam up to us, also noticing Rylan. "Rylan? Hello?"

Rylan snapped out of it, facing the two of us. "Hm? What?"

"Are you okay?" I asked him.

"Uh, yeah! I'm fine," he scratched the back of his head uncomfortably. "Uh...I think I'm going to fix up some sandwiches and bring them out here. Yeah, sandwiches."

"Uh...sure Rylan."

"Right, okay, I'll be back in a bit." He practically jumped out of the water, and booked into the kitchen grabbing a towel on the way.

"What was that all about?" I asked Brooke, who had an odd smile on her face.

"Rylan didn't say anything?" Brooke inquired.

"What are you talking about?"

"Oh my god, you don't know! Here, swim over to the edge with me." Brooke paddled over to the side and I followed.

"What is going on?!" I demanded.

"Okay. This is actually really wild. So apparently, when Mark and Rylan were in their junior year, the two of them started messing around with each other!"

"What?! Who told you that?"

"Mark did! It just came up once when we were talking. He just casually mentioned that he and Rylan used to fool around before we started dating. Actually, they stopped as soon as Mark and I got serious."

"No way! Are you for real?" I was shocked. "I just had sex with Ryan, and he was shaking and nervous! He said it was his first time!"

"First time...with a girl!"

"Unbelievable!" I slapped my forehead in disbelief.

"Yeah, but it's kind of hot too, right?" Brooke murmured.

"Well," I paused, dumbfounded, "I mean, yeah, I guess it is. I have to admit, I've always wanted to see two guys go at it with each other."

"Do you think we could convince them to do each other?"

"Brooke!"

"Well, why not? I mean, we are all naked right now. We're here for a whole week with these two hotties! God only knows what we could get up to!"

"Alright, we can casually bring it up. If they're interested. I'm still in shock that Rylan and Mark were hooking up."

Brooke winked. "We can get them to spill the beans about what exactly they like to do to each other. Just follow my lead when they get back. Bet you can't catch me!" She turned and started to swim away as I laughed and chased her.

Mark came back into the pool area, casually tapping on his phone with his cock out like it was no big deal. Setting it aside, he cannon balled into us and Brooke latched on to him. Mark picked her up and she started kissing him again. My eyes again locked on to her wet, naked body as she played with Mark.

Rylan stepped out from the kitchen with a tray of sandwiches a few minutes later, and placed it on a nearby table. The three of us climbed out of the pool and grabbed towels to dry off, but Brooke tossed it aside when she was finished, content to stay nude while she ate. I always thought of Brooke as rather shy, but now it seemed like I was the one being bashful! I followed her lead and decided to stay naked as well. The boys were more than happy to enjoy the view, and to give us a view in return.

The four of us made quick work of the sandwiches, and Rylan suggested turning on the stone hot tub. He also pulled out a bottle of vodka and some shot glasses, and in no time the four of us were happily naked and clinking glasses in the tub. We knocked back our shot glasses, and Brooke flashed me a look and a nod. I nodded in response.

"So Rylan, is it true about you and Mark?"

"What do you mean?" asked Rylan, who was preparing another shot.

"About you and Mark," I intoned, "fooling around with each other."

Rylan coughed and dropped his glass into the bubbling water. "Where did you hear that?!"

"From Brooke, obviously!" interjected Mark. "And she heard it from me. It's not a big deal. C'mon man, you used to love it!"

"Mark, don't talk about that in front of Beth!" Rylan exclaimed.

"Even though I'm a little peeved that you kinda sorta fibbed to me," I stated, as Rylan wore a guilty face, "it sounds kind of hot"

"Well, it's not exactly something you can just talk about," defended Rylan. "I mean, have you ever had sex with a chick?

"What?!" I blubbered. "I, ah, well, no, I haven't..."

"And Brooke, have you ever done a chick?" Rylan added for emphasis.

"Well, one time..." Brooke replied quietly.

The boys and I simeotaneously had our jaws hit the floor. A dozen questions flew out of our mouths speaking over each other. Brooke gave only a shy look.

"Stop. Stop stop stop, guys," I commanded. "Brooke. I have been your best friend since forever. And you never told me this?!"

"It was just one time," defended Brooke. "And like Mark said, it's not a big deal!"

"Brooke. Sweetie. Spill it. Who. When. How!"

"I gotta hear this," added Mark.

"It was last summer, okay? At cheerleading camp. Do you remember Counselor Megan?"

"Yeah, the really pretty one. Oh my god, with her?!"

"Yeah, we hooked up once. And honestly, it was really fun. I didn't say anything because I didn't think you'd be interested."

"Yeah," interjected Rylan, "and also because bi-sex is a little embarrassing to talk about!"

"Beth," asked Mark carefully, "would you be interested? In doing a chick, I mean."

All eyes fell on me. Words got caught in my throat, and I couldn't speak. The boys looked at me with wide eyes, but Brooke, she looked at me with...cautious anticipation? Remembering Brooke fucking Mark earlier and now seeing her lovely, naked body peek through the bubbles in the jet stream, a small voice escaped my lips.

"Yeah, I would try it." It was barely a whisper.

Brookes' eyes widened with relief and a certain amount of excitement, and Mark grabbed Rylan's shoulder and shook him.

"See, Rylan?" Said Mark. "I told you this would be a fucking awesome week! You can't be such a prude all the time!"

Brooke raised a finger. "Whoa, whoa, slow down. Beth and I haven't agreed to anything yet! I mean, maybe she wants to -" her eyes flashed at me as if to gauge my reaction. "- but she hasn't done it before. You two, according to Mark, were having sex all the time last year!"

"You told her about that?!" Rylan gawked.

"And before Beth and I agree to anything with each other," Brooke continued, "We want to see you two together. You've been teasing me with this gay sex reveal for weeks, my darling boyfriend, and I've been dying to see it."

"Yeah," I added, "and it would be really hot. Plus, Rylan, you kind of owe me a little for omitting this little detail of your sex life."

Rylan threw his hands into the air. "Alright, fine. Fine! I'm game. We haven't messed around since Mark and you started dating, so I'm probably way out of practice."

"Well, I wasn't going to cheat on my girlfriend, dude," said Mark.

"If it is as hot as it sounds," announced Brooke, "then you have my full permission to cheat on me a little!"

"And you definitely have my permission!" added Mark, who sidled up to Brooke and kissed her hard.

"I don't think Brooke requires your permission, Marky-boy," I commented.

They broke their kiss, and we grinned at each other. We relaxed a little longer, feeling the buzz from the vodka and not really talking too much. Mark's arm was around Brooke's shoulders and Rylan's was around mine. I loved being held by Rylan and feeling his wet body against me. Brooke and I would glance at each other sporadically, and we couldn't help but blush and look away when our eyes met. Soon Rylan pulled his hand off me and stood up.

"I'm gonna go clean up a bit," said Rylan, stepping out of the tub. "Mark, why don't you come help me while we have a word." It wasn't a suggestion.

Mark shrugged, and followed Rylan to pick up the trays and leftover sandwiches. The boys disappeared into the kitchen, leaving Brooke and I alone in the hot tub.

"Brooke," I scooted right next to her, "why didn't you tell me you had been with a girl? I thought we told each other everything!"

"I've honestly never told anyone about that night. I didn't want to be labeled a lesbian or something at school."

"But you never said anything to me. Were you embarrassed or think I would make fun of you?"

"What? No, absolutely not! I really liked being with a girl! It was...oh my god, it was incredible. But the reason I didn't say anything to you is that I didn't want it to seem like I was coming onto you or something."

"I've honestly never even considered being with a girl, until today. It never even crossed my mind. But when I saw you on top of Mark...I'll be honest, you were really sexy. I can't get that image out of my brain."

"If I were to do it again with any other girl, it would totally be you, Beth." Her hand went to my leg, under the water. I shivered, despite the heat of the tub.

"This is so crazy!" I leaned in and placed my own hand on her thigh. "I can't believe we're even talking about this! Let alone sitting naked in a hot tub together!"

"I know, I feel the same way," reassured Brooke. "Let's just play it by ear, and in the meantime think about what the boys agreed to!"

"My god, the boys! I can't believe that slipped my mind. I can't believe we're actually going to watch two guys have sex!"

"Just play it cool. Once Rylan loosens up, he'll really enjoy himself."

I squeezed Brooke's thigh, and we climbed out of the hot tub, switching it off. We grabbed our towels and started drying ourselves off. I couldn't help but run my eyes over Brooke's body, and she was doing the same to me. "Would we really have sex together?" I thought to myself. "What would sex be like with a girl? Is this really me who is thinking about Brooke this way? Is she thinking the same thing?"

These thoughts were wracking my brain when Mark and Rylan swaggered back in from the kitchen. They shared a grin on their face, and I noticed that both of their dicks seemed to be a little hard. Rylan spoke up first.

"So, Mark and I had a little chat, and we're willing to put on a little show for you."

"However," interjected Mark, "a couple of things. First, we're staying naked and so are you this week. We got a house to ourselves, so we might as well not wear any clothes!" Brooke and I nodded in agreement. Honestly, I liked the idea of running around naked. And if it meant being able to peek at the boys (and while I'm at it, Brooke) I was more than okay with it.

"Second," continued Rylan, "if you guys like watching us, Mark and I would like to see you two fool around. It seems like you two are interested." Brooke and I glanced at each other, and our cheeks went pink. "So, are you girls ready to go upstairs?"

Brooke and I squeaked out the affirmative, and the boys led the way out of the pool area. The sun was going down, and the sunlight started to fade from the glass above us. Brooke hooked on to my arm and we walked together behind the boys. Mark bounded through the hall and up the stairs first, while Rylan kept a measured pace. I loved staring at his cute bottom as he walked ahead of us.