CHAPTER TWO
(Matthew)
“Oh yes, oh fuck!”
I smiled to myself as Charlotte curled up from the lounge chair, one hand buried in the hair of the naked blonde woman between her thighs. The anonymous blonde had been going down tirelessly on my girlfriend for at least half an hour, but Charlotte showed no sign of losing interest. She panted and whimpered, ran a hand over her sweat-damp hair, and reached for the mimosa on the table between us.
Breakfast poolside was far better than breakfast in the pool, at least with the kind of entertainment we had. Because while I couldn’t take my eyes from Charlotte’s body straining in the bright morning sun, she couldn’t stop watching the man being tortured only feet from her.
My princess certainly had an imagination. Once let loose, she’d come up with a scenario hotter than anything I’d ever seen in a porno.
It had been shockingly easy to find resort guests willing to play with us this early; the man strapped to the deck chair before us, bathed in his own cum, was a paying customer. As were two of the women currently rubbing their breasts across his face, running their hands over his sweating chest.
They alternated sucking his painfully swollen, red cock and jerking it hard and fast while he screamed and twisted and begged them to stop, without ever issuing the command that would stop them.
He had more stamina than I did for the kind of torture they put him through. The third woman in their group was a resort domme supervising the scene, occasionally supplying lube, and operating the vibrating plug in the man’s ass.
“No more!” He hung his head, a thin stream of drool dribbling from his lips. “I can’t take it.”
“You can take it.” The domme held up the remote that controlled the plug and clicked a button several times. “I know you’re not empty yet.”
The man’s face contorted. He threw his head back. “Don’t make me come again!”
“Get on his dick,” she snapped to the pretty, dark-haired woman currently bobbing her head up and down on him.
I turned my attention back to Charlotte, who motioned to one of the servers standing by with our mimosas and half-finished breakfast plates. The man brought over a glass, and Charlotte tipped her head back so he could pour the drink into her open mouth. Some spilled down her chest, and the blonde between her legs eagerly moved to lap up the sticky juice and champagne mixture.
The man in the chair let out a sound that was a mix of agony and pure, animalistic desire. The woman riding his cock undulated her hips while the domme reached between them to stroke her.
“You’re going to stay on this cock until he comes again,” the domme warned. “You’re going to keep coming until he does.”
I made a mental note to get this woman a raise. She provided exceptional customer service.
It had been a long time since I’d been able to keep up with someone like Charlotte. Maybe I was kidding myself and there had never been a time I could have kept up with her. At the moment, the spirit was willing, but the flesh was tired, despite the inspiring scene. I was more than content to watch and not participate.
It gave me plenty of time to consider Charlotte in what appeared to be her natural habitat: getting fucked. I’d never met anyone as emotionally guarded and eager to be sexually vulnerable as she was. I had no doubt that she genuinely enjoyed her sexual freedom; it wouldn’t be so much fun to be with her in this environment if she didn’t.
Up until the night before, it had seemed like Charlotte was her most authentic self when she was fucking. It was only when her feelings had spilled out that I’d caught a glimpse of the deeply insecure side of her that I’d been warned about.
The gulf between “deeply insecure” and what she was doing on the lounge beside me was wide enough to swallow the seas.
The brunette on the man’s lap shouted, a high-pitched “ah!” of release that faded into giggles as the domme’s hand never let up. Soon, the giggles faded to hisses and squirms while the man openly sobbed.
“I’m… gonna…” the brunette panted. And she did, her legs trembling on either side of the chair. The domme didn’t give any reprieve from the stimulation, cooing, “Oh, is that starting to hurt, slut? I can stop as soon as you milk his cock dry.”
The blonde’s hand disappeared between Charlotte’s thighs. While the sight of Charlotte’s gorgeous face tilted up, eyelids fluttering closed in ecstasy, was erotic enough to haunt my daydreams until the end of time, my view of her pussy was obstructed. I reached for my cane and got to my feet, moving past the show in the chair to stand over my girlfriend.
My girlfriend. I would never get tired of that.
She didn’t notice me there at first, but the blonde did, smiling up at me and adding a third finger to the two she was already sawing in and out of Charlotte’s cunt.
The domme had brought plenty of lube. I silently gestured to another server to bring me a bottle. Charlotte blinked up at me through a fog of sexual bliss. Before she could say a word, I dropped the canister onto the lounge chair beside the blonde.
The next time we were here, if Charlotte wanted to participate in the lube orgy, I’d go and watch. Hearing her stories about getting fucked and fisted had been nice, but I’d been experiencing a lot of retroactive FOMO since then.
“Princess,” I began, taking a firm tone.
“Yes, my Dragon?” she giggled, then gasped and arched her thighs in time to the blonde’s rhythm.
“I think you need the whole hand to satisfy you.” I looked to the blonde for permission. Biting her bottom lip, she reached for the lube.
“Oh, please.” The already pronounced rise and fall of Charlotte’s chest became erratic. “Yes, I fucking want it.”
“I’ll give it to you,” the blonde said, already smearing lube over her hand, past her wrist.
I glanced over at the man in the chair, who was staring slack-jawed at Charlotte and her partner.
“Wait,” I suggested. “Move a bit that way…a little…there. Make sure he can see.”
Even though the man had already been forced to endure four orgasms, seeing Charlotte get fisted should help him through another two. It was certainly working for me. I’d been convinced I was happy to watch without participating, but it was too much to endure, seeing Charlotte this way and not touching myself.
I untied my robe and stroked myself slowly. I knew I needed to hold back, to keep at least some sexual energy in reserve for later, but she was so fucking hot, lying there with her legs spread, showing these total strangers her pussy and all the things her little blonde friend wanted to do to it.
“You want it slow or fast, honey?” the blonde purred.
“Fast,” I answered for Charlotte. The blonde looked to her, and Charlotte nodded.
The copious amount of lube and Charlotte’s dripping juices delivered on that promise of “fast.” Charlotte tensed up, eyes flying open wide as a flicker of disbelief and pain crossed her face. She made a stuttering, choking noise, her hands gripping the sides of the padded lounge chair.
“Keep it up,” I instructed the blonde. “She’ll tell you if it’s too much.”
Charlotte groaned as the woman almost completely withdrew her hand, then pushed back in with a corkscrew motion.
“Do you like that, Princess?” I asked. My cock throbbed in my hand.
“Yes,” she moaned.
I motioned to the staff member standing by. “Ice, please.”
Charlotte’s eyes narrowed in suspicion.
In seconds, a glass was in my hand. I sat beside her on the double-wide lounge and fished an ice cube out. “Tell me how it feels,” I instructed, bringing the ice to one of her hard nipples.
“Cold!” she gasped.
My mouth quirked into a smile. “I meant her hand stretching your pretty little cunt.” I rubbed the ice in slow circles. “Tell me how it feels.”
“Full,” she managed as the widest part of the blonde’s hand penetrated her again. “Full and… ah!”
The blonde’s steady pace was mesmerizing. I couldn’t take my eyes off her slender hand disappearing into Charlotte’s cunt all the way to the wrist.
“Stop right there,” I instructed the woman. “Keep it still. Tell me how she feels.”
“Tight,” was the blonde’s immediate answer. “She’s crushing my hand.”
I moved the rapidly melting ice to Charlotte’s other nipple, leaving a trail of freezing moisture on her skin. “But she can take it. Do you think she can take mine?”
“I think she could,” the blonde said. The tendons in her wrist flexed, and Charlotte curled up from the lounger with a choking moan.
“What do you think, Charlotte? Do you think you can take this?” I held up my fist, then spread my fingers wide so she could see the size difference.
And in her horny state, it clearly did not matter. She wetted her lips and nodded frantically.
“I’m sorry,” I said to the blonde, “but I didn’t catch your name.”
“Dahlia,” she said, withdrawing her hand from Charlotte’s body to shake mine.
I laughed, both at the hilarious introduction and the way Charlotte whined in protest. “I’d like to take over now, Dahlia,” I said, and she was already moving out of the way. “Would you be interested in staying involved? Take care of me while I take care of her?”
“I’m strictly sapphic,” Dahlia said with a laugh. “Let me check with her.”
The second woman who’d been tormenting the man in the chair looked up with interest. Dahlia made her way over and whispered something in her ear.
I turned my attention back to Charlotte and started lubing up my hand. “You’re sure you can take this?”
“Maybe not,” she admitted. “But I’m willing to try.”
I pumped more lube into my cupped palm then inserted the tips of my fingers into her pussy, letting the liquid spill onto and into her. She was already stretched out, but I still had doubts. What a limit to push, though, even if it did turn out to be a limit.
The second brunette sauntered over to us. “I heard you were in need of some assistance?”
“I want to make my princess happy.” I kept my gaze focused on Charlotte’s gaping cunt. “And while I’m doing that, maybe you could make me happy.”
The brunette considered with a crooked smile. She gestured over her shoulder. “Does milking make you happy?”
Blood surged to my already hard dick. What person with a prostate didn’t like it? “I think that would make me very, very happy.”
The thought of my cum jetting out onto Charlotte’s cunt, spread wide around my hand, was enough to make me shudder with anticipated pleasure.
“What’s your name?” Charlotte asked her. With a glance to me, Charlotte added, “I thought it would be nice to know before she penetrates you.”
“Evie,” the woman said with a laugh. She gestured to me and said, “Get on your knees and bend over.”
Charlotte’s eyes widened in delight. “She’s going to give you orders?”
“That’s fine with me.” I handed Evie the lube.
She held up her fingers. “How many?”
How many? Would getting fisted while I fisted Charlotte freak her out?
Who was I kidding? This was Charlotte.
“Start with two,” I suggested. “But if you’re cool with involving the whole gang…”
“Oh my god!” Charlotte gasped. “You’re not really going to—”
“Seems like what’s good for the goose is good for the gander,” Evie said with a shrug. “Resort standard safe words, yes?”
“Yes, thank you.” I kneeled between Charlotte’s thighs and braced myself on one elbow, leaving my right hand free to do its work. A cold splash of lube ran between my ass cheeks. I focused on Charlotte, confident that Evie could handle me fine on her own.
“Don’t be rough,” Charlotte told me as three of my fingers pressed against her opening.
“Never.” I revised my statement. “At least, never on this first time.”
I heard the lube bottle splutter, then Evie grasped my cock firmly. “Here we go, baby.” Her fingers pushed against my hole without any hesitation and slid deep. This absolutely was not her first…goose rodeo? I couldn’t make her metaphor work in my brain when she hooked her fingers down and found my prostate like she had a map to it.
My head lolled on my shoulders; it was more difficult to concentrate on Charlotte than I’d first anticipated. Breathing heavily through my nose, I managed to tell her, “We’re going to start with three.” My cupped palm and three fingers were about the equivalent of Dahlia’s entire hand.
Charlotte moaned loudly, rolling her hips.
Evie’s slick hold on my cock drifted lazily up and down, but the burn of her third finger stretching me somewhat dulled the pleasure.
“Relax,” she reminded me. It was a good reminder for Charlotte too; when I moved my pinkie between her labia, ready to join my other digits at her opening, she let out a long, slow breath.
“Doing okay?” I asked her, gritting my teeth as Evie slowly rotated her hand inside me, rocking her knuckles back and forth against my ridiculously sensitive gland.
“Ooh, this is much easier than I thought it would be,” Evie said with a giggle, bumping my hole with her pinkie.
“Yeah, not my first goose rodeo either,” I groaned.
“Your what?” Charlotte giggled.
“Oh fuck, never mind.” My cock leapt in Evie’s hand, but she didn’t increase her rhythm. “You should be doing this to—” I had no way to point at the man openly sobbing in the chair.
“I have to stop…coming!” the dark-haired woman in his lap screamed. I heard the domme’s laugh and could imagine the look on her face. Until the guest said the safe word, she was going to keep on coming and I was goddamned delighted to listen to her.
Four of my fingers filled Charlotte’s cunt up to the knuckles. Beads of sweat stood out on her forehead and in the valley between her breasts, where the ice had long since melted away.
“If you want the whole thing, you’ll have to make yourself come before I can take it out,” I told her, pausing as shivers racked my body. I was going to come, and soon. The relentless twisting of Evie’s hand was too much, especially coupled with her expert stroking of my cock. Over my shoulder, I snapped, “Do you work on a fucking farm or something?”
“Or something,” she teased.
“Well, you’re efficient.” I let out a juddering groan.
“You still want the whole thing?” she clarified.
“I’ve had bigger,” I goaded her. There was an intense, deeply uncomfortable pressure that made me swear under my breath.
“Oh fuck, is she doing it?” Charlotte panted. “Right now?”
I gritted my teeth, only managing a tight, “Yes.”
“Relax,” Evie ordered sternly. “Or I’ll take my hand off your cock and let you come without touching it.”
I relaxed. Because the idea of losing the contact of her hand, of ejaculating without having my cock stimulated, was the most awful punishment I could think of at the moment.
Charlotte writhed and whimpered. “I want it, too. Give me all of it.”
I hesitated with my thumb against her. The widest part of Evie’s hand passed through the burning ring of my hole. This time, when she started that twisting motion, it was all over.
“Fuck, I’m coming,” I groaned, and sank my entire hand into Charlotte’s pussy. Her eyes bulged, then squeezed shut, and her mouth dropped open in shock. I wanted to stop, to make sure I hadn’t hurt her too badly, but I couldn’t say anything. The pressure of Evie’s twisting hand felt like she was manipulating my cock from the inside while she pumped me firmly outside. Ropes of cum splattered over my wrist and Charlotte’s stretched cunt.
Evie didn’t let up. She leaned over my back, teasing my ear with her breath as she whispered, “We’re going to keep this up until your girl comes. It’s only fair.”
I grunted an affirmative reply, cum still leaking out of my dick as Evie fucked my ass with her hand.
“Charlotte,” I rasped. “Are you—”
Her hand fell to her clit and she rubbed herself furiously. “Don’t stop! Keep…moving…”
I rocked my hand back and forth in short movements, never pulling out of her all the way. It was a little hard to watch her for the signs, considering I was trapped in my own seemingly endless climax. Evie was dangerously skilled; the sensation didn’t fade into oversensitivity. When I came again, I could barely discern one surge of pleasure from the others until my body seized and more cum dribbled from my tip.
“I’m…I’m…” Charlotte sobbed, then her cunt squeezed down on me so hard, I wasn’t sure the surgeons would be able to save my fingers. As the strong grip began to loosen, I slid my hand out, releasing a tide of her juices onto the upholstery.
“Red,” I barked, bucking my hips against Evie’s hand. She deftly withdrew from my ass and released my cock. By the time my head rush finished and I sat back, she was toweling off her hand with a smirk.
“Thanks,” she said, making a little kiss in the air. “I love having a man fall apart for me like that.”
“I usually like to stay in one piece, but I would do that again,” I admitted with a laugh.
Turning to Charlotte, I asked, “Are you okay?”
“Mmm. Better than okay.” She reached down to her gaping cunt. “I bet I could take two cocks in there. What do you think? I’ve never been so open.”
“I think you’re fucking filthy.” I leaned down and kissed her.
When I lifted my head, she pointed to Evie. “It’s only fair if I eat her pussy in repayment.”
“That’s an excellent idea.” I rose on shaky knees and reached for my own towel to gingerly dab the cum off my stomach and thighs. I needed my cane and my robe, in that order. The staff member standing by intuited my need and hurried to help me. I watched for a moment as Evie happily reclined beside Charlotte and spread her legs, then I turned toward the house.
I would let Charlotte—and the rest of them—have their fun while I took a much-needed and well-earned breather.