Paradiso

Day 5 Continued

As we sat and ate I recounted the story of golfing that morning. It was an ordinary, mundane dinner conversation and aside from the fact that we were naked it was no different from a thousand other times we had spoken about our day over dinner. I wanted to draw out the moment so I filled in lots of details about the game; slicing on the third hole, getting stuck in the sand on the fifth, making a long putt on the sixth.

The meal was almost over by the time I described sucking my partner's cock in the locker room. I delighted in how Sara's expression went from surprised to amused to wicked then shocked and finally flabbergasted when I described how I had fallen into an all-male orgy in that locker room. I thought she might faint by the time I got to the grand finale where Greg and Vance double fucked my ass while Darren sucked my cock and I sucked Pedro's all at the same time.

Sara gave me a crooked smile.

"I knew I would get you to try gay sex when we came here but I didn't know you'd develop such a taste for it." She said breathlessly.

"Jealous?" I teased.

"Are you jealous when you watch me fuck other women?"

"I'm actually horny as hell when I watch you fuck other women, babe." I replied honestly.

"To be honest I am a little jealous that I didn't get to watch."

To that I shot her a wicked grin of my own.

"What's that smile supposed to mean?" Sara asked with a raised eyebrow.

"I thought you might feel that way so I made two calls when I ordered dinner. A few of the guys from the golf course are coming over and I thought I might give an encore."

Sara sucked in her breath and her eyes went wide. I announced that I was going to brush my teeth and she followed me silently. The two of us stood at the bathroom sink and proceeded to freshen up, but I couldn't help but notice how she kept looking at me.

I have never been a prude. I have always considered myself sexually adventurous and willing to push boundaries. My motto is "Don't knock it until you try it twice" because you should always be willing to try something once, and even if you don't really like it you should try it again because anyone can have one bad experience.

But this was a look I had never seen on Sara's face before. Sara had always been at least as wild as me, if not more so. I was always the one who was surprised at how kinky she could get. This may have been the first time since we'd met that I had surprised her. For a while I had known she wanted to include other men in our sex life with the eventual goal of getting me to explore my bisexual side. Now that I was to that point I was taking to it with a fervor that surprised her. Frankly it surprised me, too. I'd had no idea that sex with men could be such a turn-on and now that I knew I decided to embrace it.

Shortly after we had finished brushing and flossing the doorbell rang. I heard Sara suck in another breath. I looked down at her chest and her nipples were like two little pencil erasers. She was so aroused in anticipation of what she was about to see. I could feel my own cock stirring with the knowledge of what was about to happen.

We strode to the door together and opened it to find Vance, Pedro and Greg; the latter two smiling brightly, but Vance looked right into my eyes with his usual intensity and I could feel myself melt a little in the heat of his gaze. I invited them inside and made with the introductions. I explained to the three striking gentlemen that I was hoping to put on a repeat performance of what had happened earlier that day for my girlfriend, who had long wanted to see me indulge in some man to man sex.

"That sounds great." Greg agreed. "How about we have some drinks first?"

For the next half hour we sipped rum and cokes and talked about, what else, sex. Vance, it turned out, was a mid-level executive of the holding company which owned the resort, so he got to live here for a month out of every year as a fringe benefit. Pedro and Greg were both first time visitors and were here with their significant others', a girlfriend, Andrea, for Pedro and a boyfriend, Lucas, for Greg.

"You should have invited him." Sara said to Greg.

"No, he's actually occupied right now." he replied. "He met up with this amazing transsexual woman earlier; this tall, blonde bombshell with a big tattoo on her back and a giant tool between her legs."

"Jessie!" Sara and I shouted at once.

"You know her." Greg said with a smile.

"Yes." I said. "She's the one who actually broke me in, if you take my meaning."

Smiles broke out all over the room.

"Your boyfriend is in for a ride. She fucked my ass for an hour, easy. She would just cum, then put me in another position without taking out her cock than fuck me until she came again, then do it all again. She came in me three times without ever stopping to rest or even pulling her cock out of my ass."

"Shit." Pedro spat out. "After they're done, I think Lucas is going to have to introduce me."

We all had a good laugh but when it died down the whole atmosphere of the room shifted. The sexual tension had been slowly, almost imperceptibly rising, but now it was peaking and all of us knew we were ready to take it to the next step.

Vance stood up and was already sporting an impressive erection. I remembered how much pleasure I had gotten from that beautiful tool pumping in and out of my mouth and ass. He silently strode toward the bedroom, stopping only to look over his shoulder and say a word.

"Coming?"

Sara and I exchanged looks. I had told her how dominant Vance was. She and I followed behind him and Greg and Pedro followed us. When we arrived in the bedroom Vance turned around and looked me square in the eye with that predator's gaze of his. I seemed to know what he wanted without having to hear it so I walked up to him until I was within reach.

He took me by the back of the head and pulled me in for a kiss. He was firm, dominant, but not rough. His tongue massaged mine and I returned the gesture eagerly. I felt his hands stroking my body and I did the same to him, enjoying the feel of his smooth skin under my fingers. When we broke the kiss I looked to the others. Pedro and Greg were sitting side by side on the bed tugging each other's hard-ons and Sara stood in the middle of the room watching all the hot gay action going on in front of her, her legs spread while she fingered her clit.

When Vance pulled back he looked in my eyes and smiled wickedly.

"Wanna make a bet?"

"What kind of bet?"

"We sixty-nine each other." Well, I thought, at least we aren't beating around the bush. "The first man to cum is bottom."

From our activities earlier today I knew that Vance had amazing orgasm control, outlasting me and all the other guys who participated in our locker room orgy. He also knew that I leaned toward being a bottom when with other men, so the prospect of 'losing' that bet wasn't likely to deter me. I returned his lusty smile and nodded.

I looked back to see Greg on his knees stroking Pedro's cock while licking and sucking his balls. Sara, meanwhile, was fucking her pussy with two fingers while pinching her nipple with the other hand. Her eyes were wide at the sight of all this male flesh.

Vance and I laid down on the bed and we positioned ourselves on our sides rather than with one of us on top, so we could give Sara a better view of the goings on. Instead of just jumping on my cock and starting to blow me, Vance began slowly, stroking my length with his hand while licking around my groin and scrotum. He took one sensitive ball into his mouth and swirled around it with his tongue.

I followed his lead and massaged his balls with my hand while letting my tongue glide around the base of his shaft. The skin was smooth as a baby's and felt great under my tongue. When I judged him to be ready, I took Vance's seven sexy inches of hard meat into my mouth and began lavishing it with my lips and tongue. He soon did the same to me.

For a while I just closed my eyes and lost myself in the sensations of a warm mouth engulfing my cock while my own mouth pleasured Vance's sexy erection. When I heard faint smacking noises from the other side of the bed I took a momentary break from sucking off Vance to see what the others were up to.

Sara was reclining against the headboard with Greg enthusiastically eating her pussy while Pedro sawed his column of meat in and out of Greg's ass. The sight excited me and I returned to blowing Vance with even greater vigor. I let my hands wander over his flanks and thighs, every inch of him smooth.

I soon felt fingers at my anus. They circled around the wrinkled orifice and then one pressed inward, followed by another a minute later and a third soon after that. The fingers twisted inside me and curled until the fingertips made contact with my prostate. All the day's activities hadn't done anything to deaden my senses there and just a few more minutes of simultaneous oral and anal stimulation had me pumping my sperm into Vance's hot mouth.

He swallowed the load without missing a beat and as I began to pull my face off of his cock to congratulate him for winning the bet, he pushed it back down.

"Don't stop now." He commanded. "I want to cum once so that I can fuck you for a good, long time."

A chill ran up and down my spine at that and if my mouth hadn't been stuffed full of cock I probably would have responded; "Is that a promise?"

I picked up the pace of my blowjob and Vance's hands roamed over my body, stopping at my nipples to give them a pinch. A few minutes later I felt the spongy head of his dick swell up and he thrust deep into my mouth as a load of cum surged out of him. I sputtered a little at the salty liquid hitting the back of my throat, but I managed to swallow it all without spilling any.

After that Vance spun around so that we were face to face and he pulled my by the back of the head into a deep, savage kiss; our tongues still tasting of one another's semen. When he broke the kiss we lay back on the bed and continued to watch the show. Sara came first and then Pedro, groaning as he left a load deep in Greg's bowels.

For the next few minutes we all just lay there, catching our breaths. The first one to stir was Pedro who announced he was going for a shower. As he climbed off of the bed he stopped to tweak Sara's nipple. My girlfriend saw the gesture for the invitation that it was and soon followed the Latino stud. A minute later Greg followed them and then Vance and I looked at each other and without a word we headed that way ourselves.

Soon the five of us stood under the hot spray, letting it rinse us clean of the residue of sweat and sex. I knew that what had already happened was just the prelude. Vance had every intention of fucking me in the ass and I not only wanted it just for Sara's pleasure, but for my own. A whole new avenue of sexual expression and pleasure had been opened up to me in gay sex, and I was hungry for more.

As we washed each other off, feeling up our bodies and becoming aroused once more, I felt Vance's fingers at my anus; stroking and rubbing and finally pressing two fingers up inside and stroking them in and out. I felt my cock stiffen at the moment his fingertips made contact with my prostate. Suddenly Vance pulled out gave me this look that said "My cock is going in there next."

When we all dried off we exited the bathroom but before turning to the bedroom Vance stopped.

"How about we take this outside?"

I looked out the window and the sun was just beginning to set. I had enjoyed the added thrill of sex in public, so I looked to Sara and nodded. When she nodded back I returned my gaze to Vance.

"Let's do it."

Vance led the way with Sara and I, hand in hand behind him and Pedro and Greg behind us. We passed several other couples and small groups sucking and fucking along the way, but kept going until we reached a spot that Vance seemed to like. It was a busy intersection with dozens of people passing by every couple of minutes. I understood what Vance wanted. He chose a busy spot because he wanted a large audience to show off his conquest. He wanted as many people as possible to see me give my ass up to him.

He laid his hands on my shoulders and, without a word, gently but firmly pushed me to my knees. His cock was already semi-hard and I wasted no time in taking the warm flesh into my mouth. Since the first time I had taken Jessie's hard cock in my mouth that day on the beach I had grown to like it more and more.

I made full use of both my lips and tongue to tease and coax Vance's throbbing member, but not long after he was back to full hardness he pushed my head away and looked down into my eyes. Without pulling away his gaze he reached out with his left hand and Pedro handed him a bottle of lube that he must have brought along from our place without my noticing.

Vance handed the bottle to me and stood motionless, silent, staring into my eyes. I was hypnotized by his sexual power, his raw, animal intensity. I squeezed some lube into my palm and spread it over his erect penis. I massaged it in slowly, making sure to coat every inch. Then I reached behind and worked some into my asshole, preparing myself for the fucking that was to come.

The cool, soft grass was like a cushion under my back as I lay down and Vance's hands pushed my knees back until they came close to touching my chest. He took his eyes away from mine just long enough to line up his blunt cockhead with my waiting anus. Vance looked back into my eyes and a heartbeat later I felt him push inside of me.

I sighed in pleasure as the thick, sexy organ penetrated my asshole and filled me up, one inch after another. When Vance's hips finally pressed up against my ass cheeks he released my knees and put his hands down on the ground to either side of my head, bringing his face just inches from my own. I reached up and wrapped my arms around his neck and at the same time I wrapped my legs around his waist, pulling him in for a passionate kiss.

I don't know how long we remained like that. The world just shrank down to the two of us; his tongue in my mouth and mine in his, his cock stroking my tender anal walls, my own hard cock pressed between our stomachs, leaking pre-cum, the heat of his flesh pressed tight to mine and the sexy thrill of taking every inch of him in my ass.

I suddenly thought back to my college days and wondered what my fraternity brothers and friends from back then would say if they saw me like this, lying on my back, naked in public, with a man pumping his cock in and out of my rectum. What would they have called me? Faggot? Queer? Cocksucker? Sissy slut? Gay boy? I simultaneously felt shame and wonder at that; shame that my own viewpoint was once that narrow, and wonder that I could have my own horizons broadened so much in so short a time.

Now all that seemed to matter were the feelings of pleasure and passion that were overwhelming me. All other sensations, the footsteps of the passers-by, Sara's moans as she watched us and was being pleasured by herself or someone else, I didn't know, the smacking sound of flesh on flesh as Greg and Pedro were doubtlessly fucking again, it all faded to background noise as Vance fucked... no, made love to me.

After a while of this Vance's muscles tightened and he moaned into my mouth as I felt his cock swell deep in my bowels and a warmth began to fill me as his cum flowed into my ass. It was a beautiful, sexy feeling every bit as gratifying as having made a woman cum. When the orgasmic ecstasy finally passed, Vance pulled away and I finally saw the scene around me.

Over a dozen people had gathered around us and several more had joined in. Sara had watched the whole scene between Vance and me from her hands and knees while she was being fucked doggy-style by a tanned, blonde, surfer-dude looking guy. Her eyes were glassy with lust as she smiled at me.

Greg and Pedro had been joined by two other men and a woman, with the woman, a buxom brunette, in front sucking off one of the new guys, a slim, lithe, youthful blonde with a blue anklet, while Pedro fucked his ass. Greg, in turn fucked Pedro while the other new guy, a fit black man with no anklet, plowed Pedro's asshole.

I turned back to Vance and the two of us made out for a minute with his cock still buried inside me, before finally pulling apart. By the time we did Sara and her new partner had finished, so the four of us watched the others suck and fuck for a time. When they finally pulled apart it was clear that not all of them had cum. Greg, for instance, was still rock hard and looked at me lustily. When I looked once again to Vance I saw his cock rising and I knew that meant that I was about to repeat the grand finale from the day before.

I stood up as Vance laid down on his back, right where I had been lying, and straddled his hips. Back in the locker room at the golf course I had ridden Greg reverse cowgirl style to begin. This time, I wanted to look Vance in the eyes while he fucked me. So when our eyes met again I slowly knelt down until I felt his cock press between my ass cheeks. Then I reached behind and guided his cock back into my asshole. His thick, warm rod slid in as though that's exactly where it belonged.

Vance got in a few slow, pleasurable thrusts before Greg stepped up behind me and once again Vance pulled me in for a kiss. As our bodies pressed together and Vance's tongue caressed and massaged my own, I felt Greg's cock poke and prod at my rear entrance. It took a minute of this until finally, with one last push, Greg's swollen head pushed past the tight ring of muscle and once again I had two men's cocks buried in my asshole. I became just the slightest bit red when a smattering of applause broke out amongst the spectators.

I moaned out in a combination of pleasure and pain. It wasn't sharp, searing pain, but the dull ache of a muscle being stretched beyond what it is used to. Greg went slowly, only sliding more of his hard meat up inside of me when he judged I was ready for it. I looked over to Sara and she watched intently. She reached behind herself and was sliding one finger in her pussy and another into her ass.

When both men had as much of their cocks as they could manage stuffed up inside my asshole, they began a slow, easy in and out motion. Once again I was amazed by the intensity of sensation as my anal muscle, stretched tight as a rubber band, held these two large, lubed up cocks together as they penetrated and stimulated all my most sensitive places. My cock drooled pre-cum and I thought, as had been the case with Jessie, that I might cum just from the sensation of being fucked up the ass.

All of a sudden I got that feeling that someone was nearby and when I looked up I could see the young guy that Greg had been fucking earlier. He stood before me with a straining six inch hard-on in his hand. I reached out and replaced his hand with my own, giving it a few stroked before pulling him in closer. Just before taking it in my mouth I saw traces of lipstick on it where the curvy brunette had been sucking it.

Then there were three dicks inside me; two up my asshole and one in my mouth. I felt so exposed out there in the open, where anyone walking by could see, like a little gay cockslut. I had never been one of those macho-men, obsessed with flaunting my masculinity, but this was something I had never envisioned myself doing, letting myself be made into a fuck-toy for three horny men at the same time.

The taste of salty pre-cum filled my mouth and the horny sensation of my rear passage stuffed full, hard cock-flesh stroking my sensitive anal walls and my prostate getting this incredible, vigorous massage made every nerve ending in my body feel like it was on fire.

Suddenly I could feel one of the cocks filling my asshole begin to pulse and swell and another load of semen surged into me. That was all I could take. Without having been touched my own cock began to leap and shoot cum between my stomach and Vance's. The pleasure washing over me made me suck and lick the penis in my mouth all the harder and soon he came as well. I gulped down his cum as fast as his cock shot it, and soon he pulled out his satisfied dick and I was able to see my surroundings again.