Romping on Winter Break - Day 05

Writer's Note:

Here is Day 5 of my story. It is an edited version of the chapter I wrote before, but revised to match minor plot elements. Please leave a comment or send a message if you are enjoying the series. I thrive off comments, and it'll encourage me to work faster. Constructive criticism is also greatly welcomed. Enjoy.

MaiaEmpire

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Day 5

My brain was swimming in clouds as I regained consciousness the next morning. I lay on my back with my eyes closed and in extreme comfort. I hummed as I relaxed with the soft bed sheets against my skin, flexing my back and stretching. I was suddenly aware of movement on the bed, and I opened my eyes and turned my head.

Rylan was on his back, with Brooke sitting on top of him. Her pussy was skewered on his dick, and she was balancing herself on him. Past them, I saw Mark sitting on the edge of the bed slicking up his cock. Brooke made a few movements against Rylan as Mark mounted the bed and positioned himself behind Brooke's ass to enter her. I smiled as I rolled on my side. I reached down to my pussy and started to rub myself. I suppose they had started fooling around while I slept. Early bird gets the worm, or in this case, the cock. Two of them. At least I was in for a show.

Brooke's eyes were closed and her mouth opened as Mark slid his hard-on into her ass. Rylan laid still while Mark pushed into Brooke inch by inch. After minutes of this, Mark finally bottomed out in her, his pelvis against her butt cheeks. The boys stood still as Brooke gritted her teeth to adjust to the cock in her ass and the cock in her pussy. She groaned several times as she got used to the invasion, and began to push back against them.

I started to finger my pussy as Brooke shoved harder and harder onto the boys' cocks. Mark leaned forward and started sucking on the back of her neck. She gasped as Mark's lips met her skin. She opened her eyes and shot me with a naughty grin. I smiled back at her as I fucked myself with my fingers.

Brooke closed her eyes again, and tilted her head down to concentrate. She really started pumping her hips back on the boys, hissing through her teeth. She was really getting into it. Mark leaned back to fuck into her harder, and I could see Rylan on the bottom moving his hips against Brooke. My hand was moving faster in my pussy as Brooke drove towards orgasm. She squealed and cried out as her first climax shook through her. I started to cum through my fingers along with her.

The boys were definitely not finished, and they hammered into Brooke. Deep moans erupted from Brooke as the boys screwed her, and she shuddered with every thrust. Her teeth were bared and she snarled as they continued to fuck her. Mark gripped her hips and started to swear as he pounded her ass.

"Uhhhnn, fuck yeah baby! Take my cum up your ass!" he grunted.

Rylan began to groan as well. "God, your pussy feels so tight. I'm gonna cum inside of you!"

The boys released into Brooke, and Brooke flailed into a final orgasm of her own as her cum leaked out of her. Mark pulled out of Brooke and fell back onto the bed. Brooke dislodged from Rylan, and plopped down on her back between Rylan and myself. Immediately, I got to my knees and hiked her legs over my shoulders, and licked every drop of cum from her pussy and asshole. Once she was cleaned out, I sat back and appraised her.

"I should probably be upset you got all the attention, but that was one hell of a show!" I said.

Brooke leaned up on her elbows looking at me still between her legs. Her dark brown hair was tousled, and she grinned at me. "I am more than happy to take care of you in the shower, if you'd like," she suggested.

I nodded at her, and we stood up from the bed. The boys were still laying down and breathing heavily. Brooke seemed to have worn them out. I was beginning to notice that this was Brooke's fucking style; sweet in personality but rough and rowdy with boys. I figured that they would be out of commission for the next few minutes. Brooke took my hand in hers and we headed into the bathroom.

We turned on the showerheads, and climbed in. We took a few moments under the warm water, and almost immediately we embraced each other. I felt Brooke's breasts pressed against mine, and every inch of her wet, smooth skin down to her toes. Our pussies were pressed against our thighs. As we hugged each other tightly, we gently stroked each other. She might be aggressive with guys, but she was tender and soft with me.

Someone knocked on the glass, and both Brooke and I looked to see Rylan standing outside the shower. We stayed tangled against each other as Rylan spoke. "Hey ladies. Mark and I are going to clean up the kitchen from last night. We'll see you down there. You two have fun!" And with that he left me alone with my beautiful Brooke.

Brooke and I turned to each other, and with a short giggle we devoured each others' mouths. Our hands rapidly moved from our backs to our butts as we kissed. My tongue jammed inside of Brooke's mouth, and hers wrestled with mine.

For an eternity we held each other close under the water kissing. I slipped my hand down to her crotch, and she did the same. Our mouths never left each other. We furiously began to frig each other's clit as our hips moved in response. I climaxed first, and breaking from Brooke's mouth I let out a loud moan of pleasure. Brooke came shortly after with a tiny squeal. We caught our breath, and our eyes met.

"God, you're so amazing, Brooke."

"So are you, Beth. I just want to kiss you and touch you and never stop," she said as she embraced me. Our arms went around each other and we held fast.

"I wish we had done this sooner. Have sex, I mean," I said with my head on her shoulder.

"Me too," she replied, stroking my back.

"I had never even thought about having sex with another girl," I said mournfully, "and I had no idea it felt so nice. We could have been fucking this whole time."

"I know. I think I've always wanted to do it with you, even before I experimented with Megan in the summer, but I never thought you would be interested. This week has really been liberating; I feel like a totally new person."

"So do I. At least when this week is over we can still make love to each other. It'll be tricky to hook up with Rylan for a full night, but we'll be able to have a sleepover whenever we want."

Brooke giggled. "Exactly! No one will know that we'll be cheating on our boyfriends with each other every weekend!"

I shared her giggle, then I sighed happily. "It's a bit strange. I've never really had a serious boyfriend before, and now I do. And we've been fucking like crazy!"

"I know what you mean. Mark was the first boy I ever had sex with. It feels so amazing being fucked by Mark and having him hold me. I love having sex with him as much as I love having sex with you." She hugged me closer.

"That's exactly how I feel about Rylan. I love him so much. I'm not sure how the four of us ended up in this situation, but I never want it to end." We kissed each other one last time.

Brooke grimaced a little. "I'm going to need a little time to...take care of a little personal maintenance," Brooke said, pulling away from me, "Can you give me a few minutes alone?"

"No problem, hun. I'll be in the other room." I pecked her cheek and stepped out of the shower. I grabbed a towel, and began drying myself off. I exited the bathroom and closed the door behind me, giving Brooke some privacy. After I padded myself dry, I set the towel on the dresser, and looked around the bedroom.

I realized that I hadn't really explored the house that much. I had mostly stuck to the master bedroom! I decided to snoop around the house a bit while Brooke took care of herself. I walked into the hall and opened the first door on the left. It was a small study, which I assumed belonged to Rylan's father. There were loads of books on the shelves, and a desk full of papers. I poked around the shelves curiously, and the desk as well, but there wasn't that much of interest. The room was a bit too chilly, which wasn't exactly comfortable when you were walking around nude. I left the room and closed the door behind me.

I walked into the next room, which seemed to be Rylan's. There was a lot of boy-junk on the shelves, as well as a few posters and a flatscreen tv perched on the dresser. I peeped into his drawers, but there wasn't much in there except for clothes. Pretty much unnecessary for this week. I went to his bed and peeked under his mattress. Sure enough, there was a handful of nudie magazines and a bottle of lotion.

There were a few with all women, and a couple with all guys. Yep, Rylan was definitely bi. Seeing as I'd been hardcore screwing with actual naked boys and girls for days, porn magazines seemed dull and tame, so I put them back. Finding nothing else of note, I left Rylan's room and went into the next. It turned out to be Rylan's sister's room. I had forgotten that he had an older sister, and from her decor it was obvious she was a student at university. The room was typical girl-fare, with school paraphernalia on her desk and wall, with a fluffy pink bed perfectly made and unused. I guess she hadn't visited this house in a while.

I snooped under her bed, but there was no hidden treasure. Nothing really in the desk drawers as well, just some books and a bunch of pictures of her and one of her sorority sisters. They were posing together in most of the photos. They were very pretty. I went to her white dresser, and began to peek inside the drawers. Shirts in the top, then socks, then pants; nothing particularly interesting. The bottom drawer was her panty drawer, and when I felt around I touched something underneath them. I pulled out a box that was stowed under the knickers and opened it up.

Inside, there was a long pink dildo. It was almost twice as long as my hand, and was smooth and firm. I had never seen a dildo before, let alone touched one, so I pulled it out. It had a very flared and flat base for some reason, and it felt sturdy in my hand. I eyed it carefully, and peeked into the box seeing a pile of straps. Curious, I pulled it out and saw a white belt with a sort of harness and two straps going from the harness to the back. Dumbly, I couldn't figure out what the hell this was, when it hit me.

It was a strap-on dildo. I had heard about them, of course, but never seen one. I guessed that Rylan's sister was a lesbian, and her friend from her photos was actually her girlfriend. Holding the fake prick in my hand, I started to get hot. I had to try it on. I hoped Rylan's sister wouldn't mind. I set the dildo on the bed, and studied the harness. It looked like one of those athletic supporters with no coverage on the butt cheeks. I stepped into it, and pulled it up to my hips. The straps reached under my groin and to the backs of my hips, each with a small adjuster, which I pulled to tighten them.

The front part covered my groin, pressing against my pussy and leaving my butt exposed. There was a ring and some clips in the front, which I was confused by. I picked up the pink dildo by the flared base, and studied the harness. Eventually I figured out that I needed to slide the dildo through the ring and clip it in place. The base was there to keep it from falling off. I attached it, tightened the straps one more time, and walked to the full-length mirror next to the bed.

"Oh my god," I thought to myself, "I have a dick! A big, pink dick!"

The fake cock stuck straight out from my body, and I was entranced by it. I looked at it from the front, and from the side, and even peeked at my butt sticking out the back. The strap-on was very feminine, with the pink color of the shaft and some little frills in front, yet it was clearly a man-sized schlong. It looked amazing as I gripped it with my hands and pretended to jerk it a little. As I was admiring my new appendage, Brooke poked her head in from the hall.

"What are you doing in - oh my GOD!" stammered Brooke. "What are you wearing?"

I turned to Brooke, holding the dick in my hand and stuck my tongue out through my teeth. "I couldn't resist snooping a little, and I found this in a drawer. I guess Rylan's sister is into girls. What do you think?" I grinned as I whacked off the rubber cock with my hand.

"It's so...oh my god, that is so neat! Let me touch it!"

Brooke reached down and stroked the dildo. She was as fascinated with it as I was, and held it while she stared for over a minute. She looked up at me and said, "we have to try this out!"

"I was thinking the same thing!" I replied.

Brooke darted into the hallway and into the master bedroom as I followed her. The dildo swayed to the sides as I walked. It was so strange having a dick, but it was so erotic. When I got into the bedroom, Brooke was already on the bed rubbing her pussy. Even though she was double fucked that morning, she seemed to need even more dicking. And I was going to give it to her!

"Do you want to be on your back, or on your knees?" I asked.

"On my knees. Oh my god, this is going to be so fun!"

She was on all fours in an instant, with her pussy lips towards me. She ran her hand over her crotch to get herself ready. I got on my knees behind her, and aimed the dick at the entrance of her pussy. I awkwardly thrust forward, poking her with the head. I missed.

"Ooo, ah, nope, that's my tailbone," said Brooke.

"My bad. Sorry, this is pretty new to me!" I laughed.

"I know," she giggled. "Stick it in my pussy."

I grabbed the dick and lowered it to her pussy lips. I thrust against her, but it didn't want to go in. I pushed a little harder, and Brooke yelped a bit. She turned around, still on her knees.

"I think it's too dry," she said. "Let me try something."

Brooke gripped the shaft and kissed the head of the dildo. Still on her knees, she took the dildo into her mouth. She started to slobber all over it, and swirled her tongue all over it. As she pumped her mouth, I laughed at the notion that Brooke was giving me a blowjob! I reached out and grabbed her hair as she kept sucking on the cock. She looked up at me as it slid in and out, and finally she released the dick from her mouth.

"That should do it," she said. "Let's try this again!"

She turned facing away from me once again, rubbing her pussy again as she got herself a little wetter. I grabbed her hips, this time finding her pussy right away. I pushed against her lips, and this time the dildo began to slide inside of her. Brooke moaned as I entered her inch by inch. I took it carefully, and soon the harness bumped against her butt cheeks. It was all the way inside of her.

"Oh my god, that feels neat. It's bigger than Mark or Rylan! I can't believe you're fucking me, Beth!"

I got so aroused when I realized that. Here I was, wearing a strap-on and fucking a girl on her hands and knees. It was unbelievable how far I had gone this week. The harness pressed against my clit, and I held her hips to keep the dildo buried inside of her. Soon Brooke began to thrust against me, and I fucked into her in response. It was incredibly hot, but it was still a little awkward. I knew what it was like to receive a fucking, but I definitely didn't know how to give one properly.

For one thing, it was a lot of work! When Rylan or Mark fucked me, I mostly laid back and let them control the motion. Or I rode them, using my knees and gravity to slam my pussy down on them. With the strap-on I needed to use all of my thigh muscles and lower back to keep up the rhythm, and it was tiring. Also, I had no way of knowing how Brooke's pussy was reacting to it. With a penis inside of me, I could sort of feel when it needed to adjust and slow down to avoid hurting itself. With the dildo, I just kept thrusting and Brooke kept taking it.

Brooke was loving it, and she kept pounding back. Looking down and seeing her cute ass slam back against me was amazing, and everytime she did it pressed against my clit making me shiver. She soon burst and gasped, and her head collapsed on the bed. She kept her pussy on the dildo, until it eventually flopped out when she crashed on the bed. I fell back on my heels, totally exhausted. I didn't climax, but it was satisfying knowing that I had successfully fucked Brooke.

I reached back and unhooked the strap-on, and slid it down my legs. Brooke rolled over and giggled. "That was definitely interesting. Shall I fuck you now?"

"Actually, I think I will take a raincheck. I just realized that we've been fooling around up here for a couple of hours, and I am starving!" I said.

Brooke blinked and felt her tummy. "Oh my god, I completely didn't notice I was hungry!"

"It's probably because you've been filled all day!" I retorted. We howled with laughter.

Leaving the harness on the nightstand, we got out of bed and I took my hand in hers. I pecked her on the cheek, and hand in hand we walked into the hall and down the staircase. We stepped into the kitchen, and walked in on the boys. Naturally, they were up to no good. Rylan was leaning against the kitchen island with Mark behind him and fucking into him. Brooke and I smiled and walked in as if it was the most normal thing in the world.

"Uhhnn, hey ladies." said Rylan as he moved his hips back. "Feel free to, ugh, grab something to eat. I'll...fuck...I'll be with you momentarily," he said as Mark's hips slapped against him.

"Oh, you boys," I said, as Brooke and I each grabbed a bowl and some cereal. We sat next to each other pouring out the milk and cereal as Mark sodomized Rylan four feet away from us. It was a very enjoyable sight to go with our food. Mark soon grunted, and thrust hard into Rylan shooting his load inside of him. Rylan simply sighed, with his hands still on the counter and his eyes shut tight. Mark kneeled down to felch out his cum from Rylan's ass, as Brooke and I poured another bowl of cereal.

Mark stood up, and quickly jammed his tongue down Rylan's throat. Rylan gripped Mark's broad back, clawing at him like mad. They swapped whatever cum they could, and swallowed it down. I chewed my cereal in idle amusement as they turned to us.

"Sorry about that, ladies," said Rylan, wiping his mouth. "Any way, what do you feel like doing today?"

"Well, I've been lezzing out all day, I think I'd like to spend some time with my boyfriend." I replied. "Maybe we can chill by the pool?"

"I was thinking the same thing, babe. How about you two?"

Mark had moved behind Brooke, kissing the back of her neck and hugging her close. "I wouldn't mind hanging out in the media room and watching a movie. With my own girlfriend, of course."

Brooke turned and kissed Mark. "That sounds very nice, babe. Shall we?"

Brooke stood up and Mark put his arm around her. "Catch ya later, you two." he said as they walked out the door.

I took our bowls to the sink and turned to face Rylan, who stood looking at me and grinning. I leaned against the sink looking back at him.

"Hey, naked boy."

"Hey, naked girl." he replied.

"It's been a while since I had you all to myself," I said. "Not that I'm complaining. It's incredible that I've had this much sex in such a short time. I went from respectable girl to total slut in less than a day!"

"Yeah, it's been crazy." Rylan sidled up to me and pressed his body against mine. He pulled me close. "I never had sex with a girl before this week, so I was practically a virgin."

I raised my eyebrow at him. "Excuse me, Mark had been fucking your brains out for months! If anything, you were the least virginal!"

Rylan laughed. "Yeah, I suppose so. I am totally a whore when it comes to getting fucked in the ass!"

I giggled. "We might have that in common, now!"

"Though to be fair, you were the first girl I ever penetrated. So in a way, you were my first time."

I reached up and stroked his hair. "I've never felt this way about a boy before. I love you so much, Rylan. You make me feel so wonderful." I raised my head and kissed him deep.