1223

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SCOTT

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Have fun

The words shuffled around in my brain as Robert passed the hat to Eric. That and the taste of Mandy's strawberry lip balm. They were the last words Mandy said to me before she and the rest of the women walked out the door to the rooms they had drawn. I sat there with a card in my hand as Eric grabbed one from the hat, then Manny and, finally, Glenn. I took a breath and lifted the card up in my palm, shading it like a poker hand as I peaked underneath my fingers.

1223

It was Manny and Dora's room - the room right next to ours- but Dora wouldn't be there. Well, she might be there, I guess but the odds weren't as high as they would have been if Eric didn't decide to get extra creative.

"One more shot before we depart?" Robert asked. Nobody was turning that down, although some of us were less than thrilled with his choice of fireball. "Ariel loves cinnamon. And one of you lucky men will get to surprise her with that taste on your lips."

What a gentleman

We each filed, one after the other, giving the person in front of us a minute or two head start. Manny and I were the last ones, watching Robert and Eric nervously fidgeting and shifting in their seats until it was their turns.

"Well this was a pleasant surprise tonight," Manny said. I couldn't help but chuckle.

"This is the last situation I would have expected us to be in based on just about everything that's happened so far this trip."

"Well, let's make the best of it, shall we?" He gestured for me to be the next to go. I grabbed my phone and stood up, gazing around at the empty restaurant, then headed out the door.

By the time I made it out to the pool area, I couldn't see any of the other guys. They must have all made it inside already. Maybe even, well, inside.

Room 1223 was close to the restaurant and a familiar walk. I couldn't help but notice a couple enjoying the pool together as I entered the open outdoor space. The woman smiled and waved at me. I tried my best to do the same but I felt as if I was almost floating. Everything was a bit of blur. The lights seemed to have an extra glare. The soft guitar music playing from the speakers seemed to echo. I tried to control my breathing as I walked up the stairs, then down the length of the second floor walkway.

Mindlessly, I walked to my own room, pulled my card out and nearly pressed it to the keypad before I caught myself.

I wonder who's in there?

I shook the thought from my head then took a few steps, stopping in front of 1223. I looked at the door, down to the keypad, then took a deep breath. Slowly, I pressed the card to the pad.

The red light turned green.

The lock "clicked" open.

I pressed the handle down, took another quick deep breath, and pushed the door in.

"And they say dreams really don't come true."

It was Madeline.

Jesus

She looked stunning. She sat at the edge of the bed wearing the same sequenced red dress that she wore to dinner. It clung to her endless curves, accentuating every exquisite detail of her body - her firm legs, her wide hips, her narrow waist, her perfectly round breasts, and her rigid shoulders. The neckline plunged, barely covering her nipples.

Goddammit, she was sexy

I wouldn't have minded drawing any of the girls at the table. Each one was unquestionably attractive, all with their own unique features. But I'd be lying if I said I wasn't hoping Madeline would be waiting for me in the room. I felt guilty having a preference among the gluttony of beauty. But only for a moment.

"You were dreaming of me?" I asked, letting the door close behind me.

"Well, hoping really."

"Really?" I questioned. "You were hoping for me?"

"Is that so hard to believe?" she asked.

"Every guy at that table was hot and attractive and you wished that I was the one who walked through that door?"

"My husband is hot," Madeline replied quickly. "I can fuck a hot guy any time I want. But you... you're... different."

"Different from hot?"

"No," Madeline said. "I meant that you're just sexy but in a different way. Can you just get in here, this is already awkward enough."

"You've been hanging around all over this place with your tits out the past few days and now _I'm _the one making _you _feel awkward?"

"My tits make you feel awkward?"

I took a deep breath, enjoying the banter but also wishing we could just jump to the main event. She was clearly a bit nervous, but also definitely wanted to go through with it. I had to think on my feet.

"Well, I could tell you how they make me feel. Or... I could show you."

I stepped forward.

"I'm not going to lie, that was pretty smooth," Madeline said with a slight chuckle. "So is this how it works? You just walk in and we start fucking?"

I laughed. "You act like I've done this before."

"You have, haven't you?"

"Not like this." Madeline seemed to come to the realization that there were certain parts of this that were new to both of us.

"Well, how did the other ones go?" she asked.

I took a deep breath and sat down beside her. "The first time - we had met a couple at a resort and found out they lived close by us. We became friends and invited them over for drinks and dessert one day and they told us they had started to... swing with other couples. One question led to the next and, next thing I knew, the guy was escorting Mandy up to our room and I was plowing his wife on our living room couch."

"Holy shit."

"Yea," I agreed. "It was all very unexpected. Something we had never thought of and I would have never thought in a million years that Mandy would be OK with. The next time, we invited them out for ice cream and we both left with the other's partners. That was just this past Friday night. So, yea... I'm still a bit new to it all."

"And with that other couple here? What were their names again? You guys watched them have sex or something?"

"Dora and Manny," I replied. "We got here late Saturday night and, as we were exploring the resort, we passed by their room. t's right next to ours and I noticed the curtain was drawn and the light was on and I couldn't help but peak inside. And when I did I saw them in bed going to town. I didn't mean to stare. I just froze. Dora saw us and then the next night Mandy and I were having sex and she noticed our curtains were a bit open but, when she went to close them, she noticed Dora and Manny looking in so, instead, she pulled the curtains wide open and we put on a show for them."

"Wow."

"Yea. These are all things I didn't ever expect I'd be doing until about two weeks ago. Then last night we ran into them at the bar. Or maybe they saw us and followed us and came in. They initiated it. This is actually their room."

"So you were in here last night fucking Dora's brains out. Or-" Madeline caught herself, unsure whether she should continue her train of thought out loud.

"Yes," I jumped in. "Although I don't think I'd use that terminology."

"What would you say? You made sweet, passionate love to Dora in this very room last night?"

"I think I'd probably just say that I had sex with Dora in this room last night."

"Oh wow," Madeline said. "I think that just turned me on a little."

She took a deep breath then her expression became a bit more serious.

"My husband wanted to do this," she said. "I should rephrase that. We both wanted to do this. He was just the one to suggest it out loud. I think he could tell I wanted to..." She trailed off, staring forward at the window which was securely covered completely by the red curtains. "I don't mean this as in... this." she gestured around. "Like, this 'key party'. I mean... this." She waved her hands between me and her, indicating that she wanted to hook up with me.

"Oh my god," she suddenly said, a lightbulb exploding above her head. "I just realized why I'm so drawn to you."

"Why's that?"

"You remind me of a boyfriend I had in college. He was very handsome. Very charming. But he always had another girlfriend. Finally, he broke up with his girlfriend and was single and I made my move. I had a crush on this guy for years. I had dreamed about what it'd be like to end up with him, touched myself countless times thinking of the things I'd do to him. Then we finally fucked and it was... underwhelming. He was great. We dated for a while but ended up breaking up before the end of my Junior year. It wasn't because of the sex. We just didn't work out. We wanted different things. But, yea, I can't believe it took me this long to realize it, it's been driving me crazy since the first time I saw you there on the beach."

"Well, hopefully I don't let you down in that department too," I said with a chuckle.

Madeline looked at me, staring a hole through my eyes and into my soul. Then she attacked me, crashing her lips to mine. I'm not sure I'd ever been a part of a kiss like that before. It was as if passion, desperation, and unmitigated desire were poured into a cauldron and stirred around until its contents boiled and bubbled over. Our tongues were a mess, slithering around across each other's lips, accidentally slipping to our chin or cheeks.

Suddenly Madeline was on my lap, straddling me as she pulled my shirt off. Her hands cradled my face, holding it in place as her lips mauled mine. She settled down, resting her full weight on my lap, making me suddenly aware of how quickly my cock had grown to life.

I broke our kiss, attacking her neck, licking and sucking up behind her ear.

"Oh, god," she moaned softly as my lips sucked in her lobe. My hands tickled the decorative sequence of her dress as they roamed all over her back. I made my way down to her shoulder, my lips kissing and sucking across her soft skin.

"Oh, Scott," she moaned.

"Mmmm... Madeline," I whispered as I trailed my lips down her chest. My eyes widened as the lengthy crease of her cleavage came into view and the skin began squishing under the pressure of my lips.

"Oh, Scott," she moaned again as I buried my face into her tits. I licked hungrily across the full shape of her breasts. I grabbed them and squeezed them together, mushing them to my face as I groaned in pleasure. She wrapped her arms around my head, pulling me in even deeper. If I had suffocated to **** I would have died a very happy, very horny man.

I felt the weight of the shoulder straps fall into my hands and the shiny material begin to peel away from her skin. Inch by inch, it lowered, hanging onto her nipples for a brief second before falling completely, gathering around her waist. My hands and face never left her tits. I groped and sucked all over the newly exposed flesh.

"Oh, fuck," Madeline groaned as I sucked a mouthful of nipple between my lips. They were so large, erect, and perfectly pink. I swirled my tongue around her areola, causing her to shiver.

"Oh, God," I groaned. Madeline had started grinding her ass across my bulging lap. "You are so fucking sexy."

My hands dropped to her ass, slipping underneath her dress and grabbing a handful of her flesh. I had a feeling she wasn't wearing panties and my feeling was confirmed as I ran my fingers across the smooth, uncovered skin of her hips and ass.

Madeline pressed my chest, pushing me onto me onto my back. She leaned forward, dropping her incredible tits to my chest as she kissed me. Her hands shot between us, rubbing aggressively at my crotch.

"Oh, Madeline," I groaned. She somehow worked my button and zipper open and shoved her hand inside my shorts.

"Call me Maddie."

"Oh, Maddie." Her hand gripped my shaft through my boxers. Precum oozed from the tip, dampening the cotton. Her other hand dipped between her legs, helping out to undo my buckle. I lifted off the bed, allowing her to pull my pants down. She yanked and tugged until they slipped down to my knees then grabbed the waistband of my boxers. She hesitated, looking up at me, a smirk forming on her lips. Then she pulled my boxers down, joining my shorts, bunched up at my knees.

My cock sprang free. Maddie's grin grew wider. She settled back onto my lap, sliding forward, trapping my cock underneath her. It pulsed, pressing up into the folds of her pussy. She leaked honey all over my lap.

I couldn't speak. I could barely make a sound. My brain was going into overdrive as Madeline leaned forward, kissing me again. I happily gave in, slipping my tongue back into her mouth. My hands instinctively went back to her breasts, massaging them eagerly. She began sliding her hips back and forth, grinding her soaking pussy lips across the underside of my shaft.

"Jesus, Maddie," I grunted, biting her lip lightly.

In what seemed like slow motion, she reached back down between her legs, grabbed a hold of my erection, placed the tip right against her hole, then-

MADELINE - https://www.deviantart.com/sweetjamai/art/April-ONeil-1187253946

"Ahhhhh." We both moaned simultaneously as she lowered herself down my shaft, inch by inch, burying my me to the hilt inside her warm, wet vagina. She stayed there for a moment, reveling in the feeling of me filling her up.

"Jesus, you're so fucking tight," I groaned. My hands moved to her ass, trying to pull her deeper into me.

"I have some bad news," she said, suddenly.

Fuck. What could it be?

"You can't cum inside me."

I've heard much worse news in my life

"Ok," I said, nodding vigorously to show her I understood. Slowly, she pulled forward, sliding my cock from her until just the tip remained then she thrust backward, impaling herself once again.

"You feel so nice," she moaned. I gripped her ass hard, guiding her rhythm as she slowly built up a pace. Her breasts bounced lightly into my chest with each forward motion. I grabbed them, squeezed, then stuffed them into my face.

"Ahhhhh..." Madeline moaned as my lips clamped down on her hardened nipple. I licked and sucked desperately, sending her body into shivers. Her arms trembled, struggling to keep her up. She arched her back, shoving her tits aggressively into my face. The new angle sent her clit grinding across my pelvis.

"Oh, Scott!" Madeline's movements became frantic. I planted the balls of my feet on the floor and used the leverage to thrust up into her, rising my hips off the bed.

"Holy shit!" she cried out in surprise. She raised up into a seated position, riding me like a bucking bronco. Her tits - God, those perfect tits - bounced about on her chest as she started to ride me with reckless abandon.

"Fuck, Maddie!" I growled, grabbing ahold of her breasts. My legs trembled as I pounded up into her.

"Oh God, oh God, oh God," Maddie repeated over and over as her body began to tense up. "OH GOD OHHHHHH AHHHHHH!!!!"

She exploded, her hole body writhing on top of me as I held on for dear life. I thought she'd never stop cumming. Finally, she began coming down from her high, her body jolting a last few times before she collapsed onto my chest. I wrapped my arms around her, hugging her tight to my body. Her lips found mine in a tender kiss. My cock pulsed.

"Holy shit," she gasped. "You didn't?"

"You told me not to," I said. She seemed to feel bad about it. "Don't worry. That was so fucking sexy. You are so fucking sexy."

"You are such a perfect little gentleman."

"Is this something a perfect little gentlemen would do?" I asked.

Madeline didn't answer. She moved up the bed so she was lying on her back, her head resting on the pillow. Quickly, I climbed on top of her and kissed her. A jolt flashed through my body as her hands grabbed my cock, pumping aggressively. She broke our kiss and stared me directly in the eyes.

MADELINE 0

"I want you to cum all over my tits."

In an instant I was back inside her, pounding away once again. Her legs wrapped around me, pulling me in deeper.

"Cum for me, baby," Maddie moaned into my ear. I arched my back, finding the perfect angle. My vision dropped to her breasts, bouncing wildly on her chest with every thrust.

MADELINE - https://www.deviantart.com/sweetjamai/art/April-ONeil-1187254754

"Cum for me, baby." An energy began surging, starting in my toes, flowing up through my legs to my groin.

"Cum all over my tits." That did it. I pulled out, growling like a rabid bear as I aimed my cock directly at those perfect, round globes. She placed her hands on the sides of her tits, pressing them together as I erupted. The first rope erupted from my cock and splashed a thick line up her stomach. The next two blasted further, splashing across her waiting breasts. Two more reached under her chin.

"FUCK!" I grunted as a few more spurts flew from my tip, raining down on her chest. I couple more pulses dribbled cum onto her stomach.

"Jesus," I gasped, collapsing forward, my weight resting on my left hand which barely held me upright.

"Holy shit," Madeline gasped. A slight chuckle escaped her lips as she looked down at the mess I had made all over her body. Her skin shone, covered from chin to navel in my thick, sticky seed.

"Sorry," I said, trying desperately to catch my breath.

"Oh, don't mind me."

"Hey. You told me to do that."

"Yea," Maddie replied. "But I didn't expect... this."

"I'll grab you a towel."

"Don't bother," she said. "I have to jump in the shower. And you're coming with me. You need to clean up this mess you made."

"Deal," I said eagerly. "I'll get it started." I rolled off the bed and stumbled to my feet, my legs still trembling as I headed into the bathroom and turned the shower on. About a minute later the room started to fill with steam and Maddie joined me under the warm stream.

"Really?" Madeline said. I had just spent the last minute scrubbing her right breast clean then moved onto the left.

"What?" I asked, playing dumb.

"Are you just going to spend the whole time washing my tits?"

"I mean, I made quite the mess. I need to make sure you're nice and clean." She rolled her eyes as I moved back to her right breast. "OK, I think that's enough."

I quickly ran the loofa over the rest of her body in about five seconds and said, "OK, all done!"

Madeline grabbed the loofa from me and scrubbed herself down properly. My eyes dropped to her ass as she turned away from me, rinsing off her chest and stomach under the water. It was perfect, wet and shiny in the steamy shower. I stepped forward, cupping her cheeks in my hand.

"You're ass is incredible." She wiggled her hips against my hands as I squeezed her perfect globes. I leaned in, kissing her neck as my hands roamed over her curves.

"Mmmm..." she moaned as my lips made their way down to her shoulders. Suddenly she spun around, her breasts swinging along with the motion. I jumped as I felt her hand grab my crotch, rolling my dick and balls in her hand. I was still soft, still recovering from the wild time we had less than ten minutes ago.

"I'm sorry," I said. "I don't know if I can get it back up this quick."

"It's OK," Madeline said. "You already did your job for the night." She wrapped her arms around my neck, pulling me in for a deep, lingering kiss. "You were... incredible."

"I have a confession to make," I said. "I was hoping I'd draw you too."

"Bullshit," she said. "You're going to tell me you didn't want to plow Mia and her big juicy tits?"

"I mean, I certainly wouldn't have minded," I admitted. "But you have some pretty incredible tits yourself." My hand slid up her body, taking a perfectly squishy breast in each palm.

"Or Ariel?" Madeline asked. "That perfect little princess with her pretty little freckled face and her long, luscious legs."

"You noticed her legs too?" I asked. "Damn, they are nice legs, huh?"

"How could I not? Their perfect."

"You've got some great legs as well."

"Or Dora? With her... everything." I laughed. "Those big, heavy tits. Those wide hips. That fat ass."

"We've already discussed how incredible your ass is," I said. "You know, I'm beginning to think it might be you who is underestimating themselves."

Madeline, for the first time that night, was speechless. She seemed too look through me, her hazel eyes sparkling among the steamy shower.

"Let's get out of the shower," she finally said.