Waking up in Paradise

Sometimes, when you lose what you thought you wanted, you realize you had what you really wanted all the time. Standard caveats, over 18, etc. Enjoy and please leave me a comment when you're done.

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Moaning softly, as the man nestled behind me gently slipped his cock back into my ass isn't exactly how I thought I'd wake up on my first morning in Paradise, but I wasn't complaining. Rick had spent most of last night teaching me what a wonderful thing being with another man could be. That was something else I never thought would happen.

Paradise was an adult-only, all-inclusive resort in the Caribbean. The cabana was on the beach, and I was supposed to be here for two weeks with my new bride, April. She ran off with her maid of honor the night before the wedding and my deposits were nonrefundable, so I got on the plane with my best man and best friend Rick and headed for the islands.

The bartender was fully aware of the situation and made sure our drinks were never empty, an easy thing to do in an all-inclusive resort. Rick and I had gone long past what a bitch April was for dumping me like she did and were into the gritty details.

"You mean she never even gave you a decent blow job?"

"Nah, man, she'd barely put the tip in her mouth and then jerk me off. And shit, if I ever got even a little in her mouth, she'd spend a fucking hour in the bathroom, brushing her teeth and using mouthwash and then act like I'd fucking raped her or something."

"What about, like, other stuff? I mean like back there. She ever let you play with her butt?"

"Are you fucking kidding? I asked her once, and she didn't talk to me for three days. Even when I tried to go down on her, she'd push me away and finish with her hand. And then she runs off with a girl. Go figure. I guess a boy's tongue wasn't good enough to munch her carpet."

"Shit man. You guys were together like forever. Did she even let you fuck her?"

"Yeah, but that usually ended with her making fun of my cock."

"What, your cock? What's wrong with your cock?"

"She would call me a pencil dick loser; said I didn't even qualify as a real man."

"That's just bullshit. I've seen your dick, and it's actually kind of nice."

"Dude, you've been checking me out. What the hell."

"Come on. We're both too drunk to have this conversation." Rick threw a twenty on the bar for the bartender and helped me up. When I tried to stand on my own, I knew he was right. We helped each other across the resort to our cabana, got undressed, and climbed into bed.

It was hard to tell if it was the interruption of the amazing dream I was having or the fact that it was Rick shoving a finger in my ass that did it, but I jerked awake to find my cock buried in Rick's mouth and his finger in my ass. It was dark, only the ambient light in the room let me see what was happening. The feelings, though, where I should have raged, I could only moan.

This wasn't Rick's first blowjob, and I knew it immediately. He was sucking and licking and teasing my cock, his head bobbing up and down, his tongue twirling around my glans before he took me all the way into his mouth again. He was doing all of this while a finger from his right hand slowly probed my ass for my prostate, gently fucking me at the same time.

"I'm sorry, Christy, I couldn't help myself." Rick paused long enough to apologize, but didn't even pretend to stop.

"Oh, fuck." I laid my head back and lost myself in the wonderful feelings. What he called me didn't even register.

He brought me right to the edge, only to slip me from his mouth and slather my shaft with kisses as he moved down to suck my balls into his mouth. This was torture; exquisite, delicious, mind breaking torture, and Rick knew exactly what he was doing. When his finger left my anus only to be replaced by his tongue, I couldn't help myself. My cock erupted all over my stomach as my body shook and trembled. Rick didn't flinch. He just licked and tongue fucked my ass with more intensity.

Kissing his way back to my cock, up across my spunk covered stomach, Rick cleaned up the mess I'd made on the way to my lips, kissing me hard. I could taste my seed on his lips and a tinge of my ass on his tongue.

"I'm going to take you now. Just relax and it will be ok. Just relax." I was so lost in the intensity of what was happening, so awash in the afterglow of the incredible orgasm he had given me, I didn't even think to protest. Even as I watched him spread lube over his cock, even when I felt the pressure of his head at my gate, I just wanted more.

I lost myself in his eyes as he pushed into me, letting the mix of feelings carry me to a new world. It hurt, but felt good at the same time. The intense sensation of being spread open and then filled by his cock, and when that special spot inside me felt the pressure of his shaft sliding across it, I knew this was what I needed. To hell with April. I wanted Rick to fuck me senseless. He paused. I smiled and nodded. He knew I was his and drove his dick into me as far as it would go. I screamed in agony and pleasure.

The pain subsided, the pleasure growing to take the space it left in its wake. My body trembled as spasms of euphoria tore through me. I laughed, thinking about the meager excuse for sex I'd shared with April. This is what it was supposed to feel like. This is how it was supposed to be. Rick was showing me what it felt like to be wanted.

I reached up and pulled his lips to mine as he pounded me harder and faster; the feelings coursing through my body growing more and more intense.

Rick thrust into me and froze. I could feel his body shake as his cock pulsed inside me. Trembling, he tried to pull out, but I locked my feet behind him. "Not yet. Just a little longer, please." I kissed him sweetly.

"My girl likes this." He smiled at me and kissed me back.

"Uh, huh?" I wiggled my butt and clamped my ass, milking the last bit of pleasure from his cock. "A lot." Once more, it didn't register exactly what he'd said.

"We can do it again, if you'll help me get ready." Rick collapsed next to me and pulled me close.

"And just how would I do that?" I nestled close in his arms.

"My little friend is tired. He might need some inspiration to want to play again." He took one of my hands and placed it on his cock. His little friend wasn't so little.

"Oh, like maybe a massage." I squeezed and stroked.

"Or maybe a kiss or two." Rick smirked at me.

"Oh." I smiled and sat up next to him and looked at him in the dim light as he laid back, giving me full access to his body, or the parts of it he wanted me to give attention. One more thing I'd never done before.

"Strawberry lube, you nasty boy." I laughed. Mixed with the fruity flavor was a tinge of bitter saltiness and a musky taste. I was sure were remnants of what we'd just done. The result wasn't unpleasant. In fact, the longer I licked and kissed Rick's cock, the more I grew to like it. My only points of reference were porn I had watched and what I had woken up to Rick doing to me. With lots of lips and tongue and enthusiasm, I attacked his soft soldier, trying to bring it back to life.

"Ooh, yeah, just like that. Now lick my balls a little. Oh yeah, now suck. Oh baby, that's so good. You're such a good girl." Rick lavished encouragement and praise on me as I worked. Slowly, his cock hardened and challenge my burgeoning skills. Maybe it was because it was only partially hard, maybe I was just gifted, but I relaxed my throat, and he slipped all the way into my mouth.

"Oh, fuck." Rick moaned.

"Isn't that next?" I pulled him free, giggled, and did it again.

Rick grabbed my hips, repositioning me over his chest, leaned forward and once again buried his tongue in my ass. Damn, it was hard to focus on what I was doing. It became a battle to see who could distract the other. I'd deep throat Rick, and he'd let out a gasp. He replaced his tongue with one or two of his fingers and I'd choke on his cock.

"Ok, baby, it's time." He swatted my thigh. I stopped my onslaught on his cock and laid down next to him, pulling my knees up to my chest, moaning loudly as he slowly and gently pushed all the way inside me. This time, there was no pain, only pleasure. I came twice before he filled me with his seed the second time. We collapsed into each other's arms, and, covered in cum and sweat, passed out.

"Mmm, Rick, you're going to either ruin me or spoil me. God, that feels so good." I lifted my leg to give him better access as he slipped inside me. It was the second time I'd woken up to him taking advantage of me, and the second time I hadn't complained. The fact was, I loved the feeling of him inside me.

He rolled me onto my stomach and kept thrusting with gentle, easy strokes, driving me mad as his cock massaged my prostate. He was using me to conquer his morning wood and helping me with the same issue at the same time. With each thrust, he moved me forward. As a result, I rutted into the bed beneath me. With him massaging my prostate from the inside, I wouldn't last long.

"Mmm, Christy, your ass feels so good. I could do this all day." Rick got slightly more aggressive with his thrusts, and I came in buckets beneath me. This time I noticed, vaguely remembering him calling me that last night and the girl a few times.

"Is that what you want, Rick, for me to be your girl? Is that how you see me?" I moaned softly and rolled my hips, moving with his thrusts. He didn't answer. Maybe he wasn't even aware of what he had done.

"Yes!" Rick screamed as he came. I wasn't sure if it was an answer to my question or not and didn't really care, because his orgasm drove mine over the top, and I exploded into the sheets as he erupted deep in my bowels.

We had covered the sheets in yellow stains. They stuck to me where I had soiled them this morning while Rick used me. I laughed at the mess, wondering if housekeeping was just used to it. I was supposed to be on my honeymoon, after all. This certainly wasn't how I had seen that playing out, though.

Rick and I showered together, taking our time washing our lust from each other. We were doing all the things I had envisioned doing with April, yet she was the furthest thing from my mind. All I could think about was how it felt when Rick took my virginity, how I had craved him inside me this morning when I woke up to his cock pressing into me. None of this had ever crossed my mind before last night, and here I was, in the shower with him, running my hands over his taut muscular body, admiring how masculine it was when compared to my own, wondering how long we would last before he threw me onto the bed and took me again.

I stood at the mirror brushing my teeth, trying to see if I could spot what Rick saw when he called me Christy or a girl. Sure, I had long hair. It was the one thing April encouraged me about. She loved my hair and refused to let me get more than the slightest trim. We had been together for over six years, so my red, full locks hung down past my shoulders. Most times, I had it pulled back in a loose ponytail.

The rest of me, though. My face wasn't blatantly feminine, but it wasn't masculine either. Androgenous was probably the best word. I could see how it could go either way. And my body, I was smaller than most men and thin. Not skinny, but thin, and not muscular at all, but not fat. I had nice legs and a cute butt. Most of my friends teased me about that, so sure, maybe, I could see what Rick saw.

"You, ok?" Rick came up behind me, putting his hands on my shoulders. The difference between us was even more dramatic in the mirror.

"Just thinking about last night, this morning, you, me, the things we've been doing, maybe even April a little." I was still mulling over what we had done and how it made me feel, and Rick's girl comments. I absolutely didn't want to go there. "How is it we've been best friends for what, fifteen years, and I'm just finding out you like guys?"

"When did you find out you like guys?" He smiled at me in our reflection.

"Good point." We both knew the answer to that and could measure the time in mere hours. "But seriously?"

"Let's go find something to eat and I'll tell you everything. It's almost noon and I'm starving." He swatted my butt and left me standing there.

We were at a resort in the Caribbean, so swimsuits and tank tops were the order of the day. We were planning on spending the day at the beach or at the pool just chilling and recovering from our flight for the rest of the day, anyway. I stood there staring into my suitcase for a few minutes, a kind of sadness coming over me. April and I had opted to share one medium suitcase instead of using two small ones, so all her clothes for the trip were in with mine. The skimpy white bikini she had planned to wear today, right on top of everything else. I'd never get to see her wear it.

"Wear the bikini if you want to. I don't care." Rick laughed, bringing me back to my senses. I pushed it out of the way and dug out my trunks. In the furthest recesses of my mind, I wondered if, just maybe, Rick would like to see me in that little bikini.

Lunch was at a grill by the pools. Burgers and beer after a night of passionate sex sounded good to me.

"So, me and guys. You remember Amber, that redhead I dated for a while back in college?"

"She'd be hard to forget, tall, red hair, killer bod, yeah."

"Well, she's trans. She introduced me to all kinds of stuff. Even got me to dress in lingerie once. Damn, the sex was off the charts for that one."

"Wait a minute, you, Mr. second-string All-American quarterback, in lingerie?" I had to laugh. "Like stockings and garters and shit?"

"Yup. It was hot, too. She was wearing the same stuff, and when we rubbed together, it was amazing. So, anyway, she was my first. I just really liked it. Even giving her a blow job. You understand. I mean, you enjoyed what we did, right?"

"Yeah. It was amazing. So, she fucked you like you did me?"

"A few times, but I really like to be on top. That's probably the main reason we broke up. She probably has some guy wrapped around her finger somewhere, dressing in sexy lingerie or more, and letting her fuck him. And he's probably loving it."

"To be honest, I like you being on top, too." I blushed. "I don't think I've ever cum that hard before, and don't take this the wrong way, but I'm not really that interested in fucking you."

We both laughed, turning our attention back to our lunch.

We spent the afternoon doing exactly nothing. We hung out by the pool and drank mojitos, walked on the beach a little, admiring the girls in their skimpy bikinis. Rick looked at me funny, like he was trying to figure something out.

"What?" I finally called him on it.

"I was just thinking that your ass is better than most of those girls and nobody but me knows it. Those trunks cover it. I mean, if I'm going to be admiring cute butts all day, it would be nice to admire one I can actually fuck." He laughed, but it felt like there was some truth to his joke.

Too much sun or too many mojitos, whatever the reason, we finally headed back to the room. The light on the phone was flashing, so I checked the message.

"Hey, I need to run down to the office. They want to know what I want to do about the itinerary. I guess they picked up on April not being here and there are some things planned just for her. Plus, I need to add you to the golf."

"Sounds good. I'll hit the shower and get us unpacked. We can grab dinner when you get back."

The itinerary wasn't that big of a deal. Mostly I just substituted Rick for April. I mean, everybody likes a good massage and if he'd never had a manicure or a pedicure, he'd get addicted to them just like I had, so the spa day stayed. I replaced the horseback riding on the beach with a zip line trip, and the yoga and Pilates that April had insisted on with another golf day. Snorkeling and shopping, sure, why not? They stayed. Romantic dinner on the beach, nope.

When I got back to the room, Rick was out on the balcony looking out over the ocean. I jumped in the shower and washed the day from my body. He unpacked everything, even April's clothes. All three of us had our own two drawers in the dresser. Rick on the right, April in the middle and me on the left, though most of my and April's stuff was interchangeable, depending on who was wearing it. It had been an ongoing point of contention that she would always seem to 'borrow' my favorite pair of jeans.

I must have stood in front of the dresser for thirty minutes just staring down at the two open drawers, one full of my boxers and swimsuits and stuff, the other April's panties and bras, and that skimpy white bikini. I looked at Rick and thought about his subtle comments while we made love, because that's what it felt like. We weren't just fucking or having sex. Especially this morning, we were making love.

There was the joke about admiring my butt, and there was Amber and the way he talked about her. She was all girl, with a little extra, and he'd dated her for months. I remembered the way he talked about her. She could have been the one, I had been sure of it. And I had the one thing she didn't. I liked him inside me.

Trembling, I watched as my hand reached for the soft, lacy fabrics in the middle drawer. I shuddered as the soft cotton nestled against my crotch, letting out a soft moan at the way the lace trim tickled my skin when I wriggled my butt. I even chose a bra, a padded one that gave me the semblance of modest breasts. Simple shorts, a lot shorter than any I owned, that certainly showed off my butt. Last was a cute top, a kind of Henley cropped shirt that let my bra peek out and was short enough to expose my tummy. I had always loved the way it looked when April wore it. Maybe Rick would like the way it looked when I did.

I let my hair down and brushed it out, admiring myself in the mirror. Androgynous had become a sort of tomboyish cute. I had some things to work on, but I could address those at the spa tomorrow.

"Hey, you ready?" I slipped my hand into Rick's as I moved next to him on the balcony.

His smile when he looked at me spoke volumes. I had never felt like this when I was with April.

"New look. I like it." Rick smiled across our table at dinner.

"I'm glad. It's just that you called me Christy and girl when we made love, and that comment about admiring my butt, well, I just thought." I shrugged. "Maybe girls like Amber are your thing, and I can give you a little of that in exchange for what you're giving me."

"And what exactly is it am I giving you that warrants being repaid?"

"Aside from absolutely mind-blowing orgasms, maybe unconditional support and acceptance, maybe you make me feel wanted, even needed a little, and I need that right now."

We ate in silence for a while. I didn't know what was running through Rick's head, but mine was spinning with the realization of what I'd just said. That simple explanation of what Rick was doing for me described the things you did for someone you loved. We had known each other for fifteen years and knew things no one else on the planet knew. Yet we still put up with each other. We were just friends, though. Sure, now we were friends with some amazing benefits, but what if it was more?

I thought about April for a moment. I didn't even really miss her, and that was sad. We had been together for six years; we were supposed to be on our honeymoon right now. I was supposed to be sitting across from my wife and I didn't even miss her. The fact was, I didn't even want her here at all. I was with who I wanted to be with.

I just needed to figure out what that really meant.

Rick took a bite of his cheesecake, dribbling some whipped cream down his chin. I reached over and wiped it off with my finger and fed it to him. "I got the itinerary all figured out. Tomorrows a big day. Why don't you take me back to the room and fuck me senseless so we can get some sleep?"