Romping on Winter Break - Day 04

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The gang recovers, and tell stories about their first times.
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Part 11 of the 20 part series

Updated 06/12/2023
Created 08/17/2020
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Writer's Note:

Here is Day 4 of Romping on Winter Break. I thrive off of feedback, so if you are enjoying the series please leave me a comment. It'll encourage me to write faster. Or if you have a critique that is constructive, I'll take that too. Enjoy.

MaiaEmpire

***

Day 4

I lay on my side barely conscious with Rylan scrunched against my back. My eyes were still closed, and I was only vaguely aware of everything around me. My body refused to respond as Rylan held me, but I could feel my exhaustion and completely worn-out ass. It throbbed in pain, as if scolding me for going a little overboard the night before. I was too exhausted to care, and I hovered between sleeping and waking for quite some time.

At some point, I could feel Rylan's soft cock begin to thrust ever so slowly against my butt crack. I barely reacted as his dick gradually became hard and his grinding increased in speed. He even reached around to lightly grip my breast and play with my nipple. I continued to lay there dead to the world. He adjusted his hips, as I felt his cock poke between my legs.

My leg reflexively raised in response to the cockhead probing me. My brain may not have been working, but my pussy was eager to be filled and to accept anything that moved without a thought. It felt more natural to be filled than not. I was such a slut, and it felt right.

Rylan moved in and out of me gently as my hips rolled automatically in response. His rhythmic fucking began to energize me. The haze began to lift, and I reached behind me to rub his side as he kissed the back of my neck. As Rylan nibbled my neck, I noticed Brooke underneath Mark in their own entanglement. Brooke looked at me briefly, smiled weakly, and wordlessly turned her focus to Mark as he quietly thrust into her on their side of the bed.

Reasonably conscious, I popped out Rylan's cock and turned to face him. Our lips met each other and we kissed deeply. He ran his fingers through my hair and I stroked his hip. I lightly pushed him unto his back, and without breaking our kiss I mounted him. I slowly eased my pussy onto his cock, and sensuously fucked my boy.

For the next hour or so both of us girls made tender love to our boys. I don't think any of us had the energy for any sort of furious activity, so we each took it slow. We drank in our partner's presence and merely enjoyed touching and caressing. Eventually I couldn't keep moving, and I ended up with Rylan's still erect cock nestled inside of my pussy as I relaxed on top of him, trying to ignore the incessant pain in my ass. Mark lay on Brooke with his own hard rod within Brooke unmoving. She looked content just holding him.

"This is so nice," she whispered. "But I think I'm a little too sore to move at all."

"Mmmm," I agreed, my head resting on Rylan's shoulder.

"If you girls need a breather," said Rylan, "then I think it's time I claimed my prize from last night."

He shot a look at Mark, who had his eyes half closed. Mark gave a wicked grin in response.

"Heh, what's fair is fair," Mark said. "I think the girls deserve a little break and a show."

With that, I rolled off Rylan and Mark climbed off of Brooke. I achingly scooted over next to Brooke, who propped herself on her side and put her arm over me. I felt her breasts against my back and her leg intertwined with mine. It felt good being hugged and spooned by her. I was still wobbly and really just wanted to be touched and held.

Rylan had gotten up and was sitting on the edge of the bed slicking up his cock. Mark stayed on the bed, apparently deciding he wanted to be fucked on his back. He took the lube from Rylan, hiked up his legs, and stuck his fingers into his shapely ass to lube the inside. His dick was completely hard the entire time. Rylan got into position over Mark, aiming his very hard dick at Mark's very eager ass.

Mark held his knees against his chest as Rylan entered him. His eyes were closed as Rylan bottomed out in Mark's muscular butt. Rylan rolled his hips inside of Mark opening him up. Mark began to moan, pushing back against him still holding his knees with his arms. Soon Rylan's cock began to pump in and out of Mark, so Mark released his legs from his grasp and wrapped them around Rylan's back. He pulled Rylan down to kiss him as they fucked.

God, I loved seeing these two studs make out with each other. There was something about gay sex that I found fascinating. I had never thought I would actually see it in person. Then again, I never thought that I myself would actually have lesbian sex. Yet here I was, with a naked girl pressed against me, slowly tracing her fingers around my boobs and my stomach, her pussy against my throbbing ass. I nuzzled against Brooke, staring at Rylan's cock pump into Mark.

Mark pulled off of Rylan's mouth to speak. "Uhhnnn...fuck man, let me sit on your cock." He loosened his legs from Rylan's back as Rylan pulled out. Stroking his dick, Rylan lay on his back as Mark straddled him. Mark aimed his firm ass at Rylan's member, and slowly pushed his way down the shaft. Once he hit bottom, he stood straight up with his cock pointed in the air. He grinded his hips against Rylan as he moaned. He then reached back to balance himself on Rylan's thighs, and started to ride on his cock. Rylan closed his eyes and focused on the fucking motion.

Mark gritted his teeth, and moved faster and faster. His breathing became ragged as he fucked himself harder. Finally, without touching his cock, he erupted all over Rylan's stomach and chest. He didn't stop bouncing on Rylan's lap, until Rylan moaned loudly, and with a loud groan bucked against Mark. He climaxed as Mark rotated his ass. Their breathing relaxed, and Mark knelt down to kiss Rylan hard. Rylan held Mark close as he accepted his tongue.

Satisfied, Mark dislodged from Rylan's softening dick and landed face down between Rylan and us girls. His gaping asshole stuck up in the air. Brooke and I simultaneously decided to help clean up the boys, with Brooke going down and devouring Mark's asshole and myself kneeling over Mark's back and licking his cum from Rylan's chest. Rylan raked his fingers through my hair as I cleaned him up. He naturally brought me up for a kiss to collect any remaining cum from my mouth. Once I finished, I collapsed face down next to Mark as Brooke lay on Mark's legs unmoving.

At this point, I thought that the four of us were completely spent. It was hard to believe, but we had fucked for practically three days straight. If Brooke's or Mark's ass was half as tender as my own, we would definitely need to take it easy today. Rylan, however, suffered from no pain in his backside. He sat up on the edge of the bed looking down at the three of us sprawled pathetically across the bed.

"Are you guys okay?" Rylan asked. We grumbled in response, not even bothering to look up.

"Well," he continued, "I have some kitchen stuff I want to do downstairs today. Why don't you guys take a bath? There's a pretty big jacuzzi in the bathroom, and the jets will feel good if you guys' asses are a bit sore..."

"Babe, we would greatly appreciate it if you could get the water started for us," I said with my face buried in a pillow.

"I think we need a few minutes to remember how to walk properly," mumbled Brooke from Mark's hamstrings.

Rylan moseyed into the bathroom, and a few minutes later he stepped back into the bedroom. We hadn't moved an inch.

"Alright guys," he announced, "the tub is filled, the jets are on, and snacks will be on their way shortly!" He ducked into the hallway to go do his thing downstairs.

Mark, Brooke, and I stood up wincing. My ass throbbed even more as I stood, and Brooke gripped her butt cheek with a look of pain in her face. Yeah, we definitely overdid it last night. Would totally do it again, though. Just, well, not right at this moment. We gingerly stepped into the bathroom cupping our sore asses. Even Mark seemed to be having a rough time as he staggered into the bathroom with his legs spread out like a cowboy.

"Mark, I thought you said Rylan had been fucking you since last year," said Brooke, who gently lowered herself into the bathtub first. "I thought you were a pro!"

"Yeah, but not for three days straight!" Mark responded. "And not while fucking two hot chicks at the same time! A man has his limits!"

"Oh, quit your complaining," I said as I delicately stepped over the edge of the tub and dipped my pulsing ass into the water. "You get to take a bath with two naked girls!"

Mark laughed, but immediately winced and clutched his ass. He stepped in, and each of us adjusted to find a water jet to aim at our sore assholes. We each hung there, letting them work their magic on our weary bottoms. After about 20 minutes of this, Rylan came from downstairs carrying a few plates of goodies. He brought some toast, some fruit, some sausages, and even the bottle of champagne that was chilling in the fridge. After delivering, Rylan headed back downstairs to take care of some kitchen business. It was nice to have someone who loved to cook and pamper as much as Rylan.

The bathtub was working wonders on my lower body, and my aching muscles began to rejuvenate. The three of us laid our heads back, making sure that at least some of the jets were massaging our asses and muscles. For ages we lay there, munching on the snacks and recovering. Eventually, we started chatting.

"Brooke mentioned that you and Rylan had been fucking since junior year. Is that true?" I asked Mark.

"Well, not exactly. He was sleeping over at my place one night two summers ago. Rylan had found some porno video online, and we decided to watch it. It started with some dude fucking a chick, but then another dude entered the video and the guy started sucking him off as he banged the chick. I had never seen any gay sex before that night. I had to admit, it was pretty hot."

"What happened next?" asked Brooke.

"Well, since we were both hard, Rylan suggested that we try it on each other. I was a little apprehensive, but Rylan offered to suck me off first so I figured why the hell not. And he was pretty damn good at it."

"Did you blow him too?" I asked.

"Oh yeah. It's only fair, right? It felt a bit strange having his cock in my mouth, but it felt really good and he tasted even better!"

"Man, that is so hot." I said. "I wish I had a dick. I'd love to know what it feels like to get sucked off like that, or to fuck someone."

"Did you fuck his ass that night?" asked Brooke.

"Nah, not that night. It was the first time either of us had gotten a blowjob, so we were still pretty green. Rylan admitted later that the video was a setup. He wanted to mess around with me, and he figured the video would be a good way to approach it. Every weekend afterwards we would always suck each other off, and it wasn't until months had passed that we fucked.

"One night, I was sleeping over at his house. As usual, we were getting naked and ready to suck. Rylan was stripping off his underwear next to the bed, and when he bent over something came over me. I guess I never noticed how hot his ass looked, and just looking at it got me going. I came up from behind him, turned him around, and kissed him. We never kissed before that, and soon we were laying in bed making out. It got us both really hard when we pressed our dicks against each other.

"At one point, Rylan started lifting his knees under me and positioned his ass against my dick. He kept thrusting against my cock. 'Do it, man, stick your dick in me,' he kept saying. It was really hot, but we had no idea what we were doing and we were dry. My dick wouldn't fit. Rylan practically ran to the bathroom and got some lube. We slicked up, and adjusted again. Eventually I got it in him, and Rylan went crazy. He was tight and I was turned on, so I came pretty quickly. Afterwards, Rylan wanted to fuck me."

"And did he?"

"Hell yeah, and it felt awesome. I think we fucked each other like three times that night. We just kept getting hard. After that night, we fucked each other practically every weekend."

"If he suggested it to you first, Rylan must be bisexual," I stated. "Are you?"

"I dunno. I don't want to date a guy or anything. I just like dick. Rylan's the only dude I've ever played around with. Of course, once Brooke and I started going out, we stopped." He glanced at Brooke. "How about you, babe? Are you bisexual?"

Brooke thought for a moment. "Maybe. Like I said, the first time I ever had sex with anyone was at cheerleader camp last June. And it was with another girl."

"I still can't believe you fucked Counselor Megan!" I said. "How did that happen?"

"Well, remember that night we had that huge rainstorm?" I nodded. "Well," she continued, "I was helping her haul some outdoor gear into storage before the dinner bell rang. It started pouring, and we got caught outside. Her private cabin was close, so that's where we ran. We were drenched by the time we got there, so she took off her clothes to let them dry and told me to do the same while we waited for the storm to pass.

"We hung up our soaked clothes and toweled off, but she didn't bother to change into something else. She just tossed her towel aside and plopped down on her bed to send out a text. Since she was naked I decided to stay naked too, even though I was kind of embarrassed. Megan was really sweet and told me to hang out with her until the rain stopped. I sat on the bed with her and she just started chatting. I couldn't help but stare at her boobs and perfect skin as she talked, but she didn't even seem to notice. She talked to me about her university and her sorority and life in general while we were waiting for the rain to let up. But it never did.

"Eventually it got dark, and it was torture sitting there trying not to stare at her body and pretend I wasn't. I started squirming a little. Megan peeked out the window at the rain still pouring outside. 'It's still coming down,' she said leaning against the window. 'Why don't you sleep with me tonight?'

When she asked me that I totally freaked out. I blushed and blurted out, 'I don't know how to have sex with a girl!' She giggled when I said that, and my heart was beating out of my chest.

"'Well, silly,' she said, 'I meant just stay here in my cabin and fall asleep!' But then, she crawled close to me and whispered, 'but we could, if you want. Have sex, I mean. I was kind of hoping we would, but I didn't want to pressure you or anything. You're so pretty.' I think I squealed a little when she said that.

She stroked my cheek softly. 'Plus, we are already naked, after all,' she continued. She looked me dead in the eye. 'So, do you want to have sex with me?' I got really bashful, and turned my head. I couldn't even look at her. I nodded, quickly. She gently lifted me by the chin, and looked straight into my eyes. I could have died right there. 'Don't be nervous,' she whispered, 'I've done this before. I'll show you how girls make love to each other. You'll love it.' Then she kissed me. Oh my god, it felt incredible."

I was flabbergasted as I listened to Brooke talk. "I can't believe that's where you were during that storm!" I said. "I was stuck in the mess hall doing some stupid team building exercise! What happened next?"

"Well, we kept kissing and got under the covers. She laid on top of me, and we grinded our pussies on each others' thighs while we made out. After a while she sucked my boobs and went down on me. I think I orgasmed a dozen times. Then she showed me how to lick her. I guess she had a lot of experience with other girls in her sorority, because she was a good teacher! We did it until we were exhausted, and I ended up cuddling with her all night. I snuck back to my cabin when the sun came up. We never hooked up after that, and the two of us acted like nothing had happened. She probably could have gotten fired or something."

Mark had been listening with his jaw slack, quietly stroking his dick under the water. "Damn, that is hot," was all he managed to get out.

Brooke continued. "So like I said, I'm probably bisexual. I love the idea of being with a girl. I was really excited when you let me go down on you, because I really wanted to try it with another girl again. Especially you, Beth." She flashed her adorable smile at me.

"I'm glad," I responded. I leaned over and kissed her softly. I adored this sweet girl so much.

Mark cleared his throat as we broke our kiss. "So does this mean you're bisexual too, Beth?"

I laughed as I hugged Brooke. "I don't know. Seeing as I've only ever been with Brooke, maybe I'm just Brooke-sexual." They chuckled along with me.

By now we were all feeling a lot better. The bath really worked its magic on our soreness. For hours we just sat in the bath pawing each other and finishing off the champagne. Rylan eventually came in to check on us, taking off his apron and getting nude as he walked in. He sat on the edge of the tub and touched my shoulder. He leaned down to peck me on the lips.

"So, are you guys feeling better? You've been in here most of the afternoon! Having a good soak?"

"Much better," I replied, "Mark was telling us about how you and him started having sex."

"Heh, yeah. I had wanted to fuck a guy for the longest time, and who better to try it with than your best friend? Remembering all of the action I was getting from him was one of the reasons he was able to convince me to ask you to come this week."

"Seriously?"

He shrugged. "I've never been that great at talking to girls, especially if I had a crush on them. Talking to guys was always easier, but it's not like you can date them at our school. When I talked Mark into letting me blow him, I was terrified. But then we did it, and it was great. And then we fucked, and that was even better. But we stopped once Brooke was in the picture, and I haven't had any kind of sex since then."

"Now I feel guilty about stealing Mark's cock away from you, Rylan," apologised Brooke.

"That's actually why we set this whole week up," added Mark. "Rylan was able to get this place while his parents were out of the country, and I figured if I brought along Brooke she'd be able to convince you to come. And Rylan could stop being a pussy and just seal the deal with you already!"

I clapped my hands. "So you guys were plotting to fuck me this whole time! I'm...flattered?"

"I'm just sorry it took me this long to get up the nerve," said Rylan. "Now, well, I can't believe I was so hesitant. This week has been fucking awesome so far! He waved his hand dismissively. "Anyway, I've been busy downstairs cooking while you guys have been bathing. Are you guys hungry?"

Rylan offered his hand to help me out of the tub as Mark helped Brooke. Rylan embraced my wet body, and kissed me. He helped dry me off as the others drained the tub and grabbed towels for themselves. I noticed we were all moving normally now, and not cringing with every step.

Rylan bowed very dramatically to me. "Would you allow us fine men to escort you lovely ladies downstairs for your dinner this evening?" He offered his arm like a gentleman. A very nude, silly gentleman. I loved seeing this playful side of Rylan. Smiling, I took his elbow as we exited the bathroom. Mark bowed to Brooke as well, and offered his arm to her.

We walked down the hallway like this, with Brooke and I hanging off their arms and giggling like mad. The boys led us to the landings of the twin marble staircases, Rylan and I at one and Mark and Brooke at the other. We stood stiff, tall, and proper at the top of the stairs for a moment, and step by step our naked princes escorted us naked princesses down the stairs. I squeezed Rylan's arm tight as I pretended to be dignified. Well, as dignified and you could possibly be without a stitch of clothing.

With me on his arm, Rylan led us into the dining room. It had a large double door entry with solid wood frames. Rylan took one handle and Mark took the other as they dramatically threw them open. The dining room was classically designed and very fancy with artwork hanging on the blue wallpaper. The table in the center was solid pine, and on it was a candlelit dinner that Rylan had prepared.

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