A Quick Pounding at the Resort [Gay][Bi][Mm][Exhibition][Voyeur][anal][sissy]

Although Jackson had comped the room, he had made his instructions very clear;

Check in. Get naked. Take in the attractions, talk to other guests, couples. Just explore the resort, don’t look for me. I’ll come when it’s time.

I had intentions to do just that.

*Paraíso* was a nude and couples resort/retreat along Brazils more southern coast. Away from the riff raff or Sao Paulo and Rio, it offered groups of typically wealthy tourists the chance to take in the warm waters and exotic views of Brazil while also enjoying a getaway among like minded people who agreed on ones freedom to express their bodies anyway they wanted. Staff, always clothed, milled about the grounds here and there and housekeepers made their calls down the hall – used to simply opening a door as do-no-disturb signs weren’t really considered here.

I had ended up here completely free, and completely by luck. The story isn’t too totally important. I sext and cam for some horny guys and they pay to see me slide toys into my ass, jerk off onto my face, eat my cum, etc. I charged gift-cards and gave a decent show, flirting with clients the whole time. Honestly, it’s something I do enjoy. There’s something about exhibition I just love.

One of my clients, under the simple name *Jackson1985,* always tipped well and always wanted to private. We hit it off well, flirted constantly, he started sending me gift cards and actual gifts even when we weren’t camming. I’d found myself, we joked, a sugardaddy. Thing is, I *really* enjoyed him. When we got to private cam sessions, Jackson, it was revealed, was a 6’5″ stud, built well and muscular, hairy, olive-tan skin, dark and thick brown hair, godly jawline and a cock that’d make any size-queen numb. We traded pictures and video for weeks, and I relished in the fact knowing I was getting such a *man* off. He’d talk about rimming me, fucking my mouth, making me a subservient sissy whore, I would talk about milking and edging him, getting fucked hard face-down by him, eating his sweet cum as I made him explode, the feeling of my boy-pussy being filled by him.

We lusted after one another so much that he even sent me an 8-inch dildo, the kind with no silicon balls at the bottom, just plain old girthy length. He said, ‘this is just a *taste*’ when I had said I’d gotten the gift. When I pressed him on it, he proposed this trip – and what he wanted to do with me – and I graciously accepted before giving him the show of a life time with the new toy. I came without even touching my cock.

Speaking of my cock. It’s not bad by anymeans. 6.5″ erect (dwarfed by Jacksons hulking 9.5 inches), but part of the sissy lifestyle usually tends to mean I lean towards men that are even bigger than me. More powerful, stronger, alpha. I’ve lost interest in clients solely because they didn’t have the dominant look and cock I was aching for. In return, I femme’d myself out for such men. I shaved everything, I wore panties, I showed off my long legs and the bubble-butt ass I was working on. My flat belly and chest, signs that I was simply just a cross dresser but it was my lower body and overall submissive act that got the men going and made me gush, knowing I was craved so much. Men begging to eat my ass, fuck my boy-pussy, fuck my mouth. I loved the attention and clutched to a big cock when I could find it.

Which is all how I ended up in Brazil, landing in a small coastal town on a charter flight and being taxi’d to the resort. It was pretty quiet. Besides staff, regular people milled about. The resort had an open attitude to both nudity and sexuality so long as more vulgar acts didn’t disturb the guests. I could see some couples (clothed or not) drifting between the pools and bars, lounging, laughing, caressing and complimenting one another. The crowd was mostly mid-30’s to late 50’s, some older bodies but a fair amount of fit people. Older women with classic MILF bodies, large waisted and titted. Older men with flaccid or cock-ringed dicks smiling at one another. The occasional hard-bodied 20-something women came by and drew glances from all present, brief admiration for perky petite tits and a bouncing ass with each step, but besides that the atmosphere was one of just plain, average to pleasantly attractive people taking in their surroundings.

I stood a bit nervous near when the main lobby of the resort met the open air lounging areas where many men and women lay openly naked along lawn beds and the grass. I was still in the shade of an outbuilding admiring how the high noon sun beat down on naked bodies, some tan and others fresh from a late spring. Peoples seemed to enjoy themselves and the company, occasionally a giggling couple with rise and follow one another back to their bungalows, soft ass-slaps resonating along the way.

I stood with my hip cocked outwards and my weight on one leg. The femme frame I had worked on over the years lent itself to giving my a pleasantly girlish gait that worked well with my 5’8″ height. Maybe a bit ‘taller’ for a convincing cross dresser, but thick where it counted, something I loved. I stared at my flaccid cock, sitting in its covered foreskin, wondering if I would pop a boner the second I got out there. I scanned the foliage for a glimpse of Jackson and got none, then decided to drift into the courtyard and walk among the couples.

I could already see men and some women in my periphery watch my ass bob and hips shift so woman-like. One of the 20-somethings even made eye contact with me and smiled. Everyone enjoys a scultped bubble-butt and I think the added image of my cute flaccid dick and smooth, hairless body caught some attention. Two older woman, both about my height, came up to talk to me. One was blonde, and the other a brunette, and they introduced themselves as Sam and Sarah respectively. Both had black thongs hugging their waist lines and disappearing somewhere into their hip-cleavage and voluptuous asses, but had opted out of keeping their bikini tops on in favor of sunning breasts that you could hold in your hands.

“Are you here alone then?” Sam asked, “or with a date?”

“With a date,” I replied, “I’m just waiting to meet him around the resort later.”

“Oh well of course!” Sarah laughed, “a cute some-body like yourself wouldn’t be here all alone, I don’t imagine you’d have a hard time making some company pretty fast” she motioned to two men in their late 20’s stroking one anothers inner thighs, watching my backside. “You don’t know when you’re meeting your date?”

“He’s kind of, uh, *particular*?” I mentioned, “He just wants me to enjoy myself around the place and then show up to treat me further” I laughed nervously.

“OH, I think I know what you mean” laughed Sarah, brushing my arm. Although I worked with men only, I still considered myself bi and having these two women, thick where it counted, laughing and casually questioning my on my sex life was eliciting a response.

“Oh, Sarah look what you’ve done to him!”

I gave an embarrassed laugh as my cock rose slowly to half mast, foreskin sliding off over the head.

“Oh, now look at that,” Sarah laughed as I apologized, “You have nothing to apologize about, young man, that’s a handsome unit you’ve got there!”

Sam whispered and eye’d something to Sarah before grinning my way again, saying, “so?”

Which Sarah then carried on, “Sam and I are going over to the shallow pool to catch some sun and lay in the water – it’s shallow, only a few inches, and you get these floaty beds and just splash around, it’s real nice.”

“And we’re goona lose these,” added Sam with a wink, motioning to her thong, “you’d be welcome to join us and get some sun on those cheeks if you’d like?”

I gazed over my shoulder at my round, pink bottom. Yup. “You have lotion?” I asked, trying to ignore my slowly-reseeding hard-on.

“Of course!” Sarah said, “We can even rub it onto one another if you’d like?”

These two women were here to play, alright. They also seemed into my overall femme thing I had going on, so I agreed to accompany them. Towards mid-afternoon we drifted into an area of the courtyard on built-up banks that oversaw the ocean and its short cascading waves making their journey towards landfall. There was a wading pool in the center of the banks with no couples around, most having drifted towards the beach to lay or fuck in the sand.

Sam and Sarah both stepped towards the edge of the pool and bent over in front of me, each wiggling out of their thong and leaving it on the ground before giggling and stepping into the pool. I couldn’t keep track of which ass I watched bob back and forth more as they walked, layed down on the chests in a very shallow area of the pool, and presented their cheeks skywards. Both had maintained pubic hair and pussies with thick lips – the kind you just slurp and bury your tongue into for days sucking the clit until they climax on your face. I took a seat at the pools edge, legs spread and thighs baking under the sun. Both Sarah and Sam gave a giggle over their shoulders at my half hard dick aching at the site of them. They wiggled their asses at me playfully and talked quietly among themselves, gazing over at me again from time to time to see how tormented I was. The last time Sam gazed, she nodded at something past me, raising her eyebrows as she did.

I turned to find myself sitting crotch-level to an endowed member I recognized all to well.

“We finally meet.” Jackson said in a deep, silky voice, looking down at me, shifting to block my view of the sun.

I was taken aback by his sudden appearance, but mostly because I was met with nervous energy at his presence. I had sort of imagined in my head that he was skulking the perimeter of the land, half-hard, waiting to pounce on me and open up my boy pussy for the onlookers to gaze at and enjoy. Or meet me as I was walking back to my room, pin my naked body chest-first to the wall in the hallway and fuck my ass right there. I hadn’t expected him to make an appearance so soon, least of all while I was ogling Sam and Sarah, playfully caressing my shaft.

Both of them were admiring Jacksons body and cock, wagging their asses into the air a bit more as if to say, ‘if *he* doesn’t cut it, we’re available.’ Jackson just laughed and shifted his weight from one leg to the next as if to show off, “you keeping my date company?”

“Only warming him up!” Sam laughed, “He’s a damn-cute find!”

“Oh, I know” Jackson smiled. By now I was standing beside him – shorter than him and facing his chin. His overall frame dwarfed mine and I could feel his eyes slipping from my feet, up my legs, thighs, cock, belly, nipples, face, and landing on my pixie-cut short hair. My eyes were doing the opposite, moving from his chin, down his pecs and abs, over his v-shaped groin, his hulking meat, his trunk-like legs, and his feet. Every inch of it all covered in his thick hair as well. He smelled as though he had just showered.

“So hows my date liking *Paraíso* so far?” he smirked, knowing the answer.

I gave a giggling shutter, feeling my ass pulsate. “I’m enjoying it fine so far, *daddy.*” I leaned into him, giving a girly lift to my one leg as our bodies and lips met. I felt *scooped up* in his arms as my softer body and his harder met, my hands drifting up his abs and cupping his pecs. I soon found his tongue burrowing deep into my mouth and saliva pooling down my chin. My legs felt weak as if all the blood pumped only to my cock and stopped there. I could feel him getting hard as well, a growing snake sandwiched into my upper thigh.

“Get a room you two!” Sam laughed.

“Or fuck the girly-boy like he needs right now!” added Sarah.

Jackson pulled himself from me and laughed, “care for a show, then?” he asked.

“*Yaass*” the two gave a hearty reply, adjusting themselves to now face us.

“No fucking in the pool though” Sam quipped, “That’s no joke, they don’t like it!”

“Won’t stop us from being wet as water in here” Sarah backed her up again. They lounged laying on their chests, propped up on their arms, watching me, watching Jackson, and watching our cocks bob back and forth as he took position behind me. I gasped as I felt his cock, fully erect, softly flop inbetween my ass cheeks. His hands were running over my ass and up my body, then dipping to the groin and softly running over my cock and he kissed the length of my neck up and down. My hands drifted around my back, one caressing his leg and the other running up his neck and into his hair, gripping thick tufts of it while our bodies bobbed into one another.

Finally Jackson got on his knees behind me, and I could feel his hands jiggling my cheeks and a sudden warm sensation on my boy-pussy. My man was eating me out, his hot tongue running over the surface of my tight, aching hole. The girls both watched me and could see by my widening eyes and smile that I was enjoying my treat. I couldn’t help my press my thighs together when Jacksons tongue finally slipped into me, licking long, wide circles before dipping out and repeating the process on the outside. Jackson gave grunts of enjoyment while a long stream of precum began to ooze out of my head, hard as a rock and swollen as if it was ready to pop. My hands gripped his hair and I found myself grinding into his tongue, Sam and Sarah smiling and giving reassuring nods as they watched my gyrate on his face.

“God damn, this boy can fuck!” Sarah screamed, her legs rubbing together behind her.

“And this man can *fuck*” Added Sam, one of her hands disappearing below her.

Jackson grunted and gave my ass a few slaps, slurping on. Occasionally he reached around and touched the head of my cock, gripping it softly, rubbing the precum onto his fingers and then slipping those same fingers into the hole he’d been warming up. Thick fingers, first one a knuckle deep, and tickling inwards towards my prostate. Then another, then two knuckles deep, rimming me as his fingers slip in and out, in and out, my legs feeling as though to give way which each gentle thrust.

“Fuck him already!” Sarah begged, “The boy’s ready to pop!”

“You want me to fuck my slut for you?” He laughed, looking up at me, myself peaking over my shoulder at him. I could feel my cheeks were warm and rosy and my eyes begging him to fill me. “What do you say, sissy?” he asked?

I took the queue, and without missing a beat, got down onto my knees, and lay flat on my chest. My cock was shoved between my groin and the smooth, warm sun-beat tile, and my ass wiggled, presented to the air. I felt Jacksons legs, his meaty thighs on the outside of mind while two large hands gripped my cheeks. Spit-covered hands and fingers nudged into my boy pussy and I gasped with delight, my cock jolting.

Then I felt it. The thick mushroom-head of Jacksons member pressing softly on my hole. He was gyrating his hips, softly pushing into me and I responded by doing the same. I could feel myself opening up, first to the extreme girth of his cock as it slid over the barrier, and then the warm, satisfying release as the head was fully enveloped in my ass, almost *sucked in* to my welcoming, hot boy pussy. The women both saw in my eyes when he’d softly entered me, and I felt both my hands reaching out for something to grab onto. Instead, Jackson pulled both my arms back and pinned them against me ass. He was only up his glands and already I felt full, my cock pulsing with every heart beat and precum cooling against my stomach as it drizzled out.

Jackson began to inch slowly into me, dipping back, spitting, rubbing me, spitting some more, sliding in a bit more, over and over again. It was slow, but intentional. He would retreat tenderly before coming back a bit rougher and harder than before, each time his cock hitting all new nerves I didn’t even know I had, and going further and further into me.

“All that anal training did my sissy good!” declared Jackson, leaning in to kiss my neck and whisper in my ear, “My little sissy has been waiting for her hole to be filled, hasn’t she?”

“Yes!” I squealed, “Yes *daddy.*”

“I wanna hear my slut beg me to fuck her” Jackson ordered, “beg me to fuck you and make your sissy-clitty come from my big alpha cock”

“I need you cock!” I squealed again, his pace now increasing as he delved into me deeper, “Fuck me hard!” I cried

Jackson drove his cock deeper into me yet, and again, and again, he was now grunting. With one hand my arms were pinned beneath his strength, while with the other she gave my ass slaps as the sound of my cheeks meeting his body rose and rose. I was aching and moaning and opened my eyes briefly to see both Sam and Sarah had come to the edge of the pool to be closer to the action and watch me get fucked. They traded comments back and forth and were giving one another slow kisses and caressing one another nipples and lay side by side, eyes on fire watching Jackson work me into the stratosphere.

Jackson scooped up my short hair and made my arch my back, my ass thrusting into his weight more readily while I reeled in ecstasy. He was in me by his entirety now, slamming me with long, fast thrusts, grunting without saying a thing while I lay before him in helpless rapture, gyrating with his motions as if to somehow unlock even more length from his cock that both of us didn’t know about. Sweat was pooling on the small of my back and I could feel it falling from Jackson as he consumed all I was. I found I had noticed my hands were now free, but rather than looking for bed-sheets to clutch, they were spreading my ass open for each thrust of Jacksons. I moaned as I felt my own orgasm welling inside of me, and felt an explosion of heat against my belly, declaring to Jackson a triumphant “*yessss*” while he kept thrusting, making my arch my back even more.

Jackson so followed suite. He kept position, just leaned back and shifted his weight from his knees to his hands as he arched his pelvis up and continued fucking, grunting, huffing while his pace seemed to quicken. He was close too.

I felt myself already hard again, legs numb to sensation while my ass burned from a mixture of plain good fucking, and slaps. Laying prone like this, I would have thought I wouldn’t even be tired from the fucking, but I found I didn’t think I could even shift my position without Jackson guiding me through the apparent full-body-orgasm that was rending me immobile. My legs quivered against his, and I felt more cum blasting into my belly and coating my stomach. As this was happening, Jackson gave a satisfying grunt while his own legs and cock began to quiver, and I felt a load pooling into my tight boy pussy. Jackson had cream-pied me, and after coming to a full stop, slipped out of me in one cool motion. I could feel cum ooze from my anus, down my taint, and dribble over my balls.

The ladies congratulated me and Jackson.

“Boy, I need a cigarette after that!” laughed Sam, “I think our little friend he does too!”

“What he needs it some water” said Sarah, looking at me pant while I raised my head briefly before dropping it again, wiggling my ass skywards.

“What I need is more of *that!*” I managed to laugh out.

“Well,” Jackson said, “Luckily we’re here for the week!” He leaned into me and scooped my cheeks up in his hand, pressing a kiss to each one before giving them a slap, “my little slut will get plenty more before the day is out.”

Source: reddit.com/r/sexystories/comments/8fmlur/a_quick_pounding_at_the_resort