CHAPTER EIGHT
(Charlotte)
I wasn’t sure how Matt planned to top what we’d already done at Ascend Red, but I couldn’t wait to find out. I woke on the morning of my big surprise to find that it was something of an all-day affair. An all-day affair during which I was not allowed to come.
“Why do you love tormenting me like that? I think we’ve already proved I’m capable of more than one orgasm,” I joked as I headed from the bathroom into the bedroom.
“Good girls earn them through obedience,” he said, gesturing me over to the bed. “I want you edging nonstop today.”
I looked down at the “clothing” he’d selected for me to wear until my surprise that evening. A pair of delicate, pink lace panties with two strings of pearls where a cloth crotch should be.
“Let me help you put these on correctly,” he said as I stepped into them.
I gave him a wry look and pulled them up to my thighs before moving to stand in front of him. He slid the stretchy lace over my hips and parted me with one finger, drawing the pearls up tight against me. He tucked the strands between my inner and outer labia on both sides, so the pearls were trapped around my clit.
“Why don’t you walk over to the mirror and tell me what you think?” he suggested.
A single step told me how deliciously miserable my day would be. The cool beads warmed rapidly against my flesh, and the slightest movement slid the teasing bumps back and forth. I examined myself in the mirror. The pearls pushed my inner lips together and forced them to protrude more than they usually did, while my clit was prominently displayed like a ruby in an ostentatious piece of jewelry.
“I assume we’re going to take a long, long walk today?” I asked, already knowing the answer.
“I thought that would be nice. Except for the walking part.” He sat and leaned forward, hands casually braced on the silver dragon head that topped his cane. He thumped the end on the floor with purpose. “I’m going to leave the walking to someone else.”
“You’re not coming with me?”
He shook his head. “I need an hour, hour and a half to make sure everything is ready for tonight. I’ve selected someone who’s eager to spend time with you. A friend of mine, actually.” Something naughty and pleased twinkled in Matt’s eyes.
“So, I’m going to go somewhere with a gentleman who wants to ‘spend time’ with me.” I made air quotes and ignored the glide of the pearls against my intimate flesh as I walked back to him.
“Yes. I’ve given you to him. You’ll do whatever he tells you. Do you understand that, princess?” Matt asked, reaching up to grab my chin roughly and hold it.
“Everything but come, my dragon,” I replied, moaning when he swiped his thumb across my lower lip.
“Good girl. He should be here any—”
The doorbell rang.
“I will go and get him,” Matt said with a chuckle, pushing himself up. “You stay here.”
I stepped back, and he gave me a kiss on the top of my head as he passed me. Technically, I was “staying here” by not leaving the bedroom, so I let myself go as far as the door. My toes touched, but didn’t cross, the line in the tile in the doorway.
“Hey!” a deep voice enthused over the sound of the door opening. This was someone Matt knew well.
Not that I thought he would place me in the unsupervised hands of an actual stranger and give them carte blanche access to my body. Everything we’d done so far, at least in the realm of him sharing me, had been with him present. He must have trusted this person a lot.
Matt was equally enthusiastic in greeting the stranger. “Dante! Good to see you again. It’s been a while since you’ve been down here. What’s keeping you away?”
“Touring. And touring. And touring.” The guy laughed. There was something familiar about his voice, and now that he mentioned touring, my brain tried to place him.
“I was worried I’d lost a valuable guest. Hence my offer to…take advantage of my personal amenity,” Matt joked. He’d better have been joking. Or we would have words.
Then again, there was no doubt that he would have anticipated I would eavesdrop. He knew me too well, and frankly, I knew myself well enough to know he was right not to trust me.
“It was an offer I could not refuse. You said she’s fucking gorgeous, and she’s staying in the house with you.”
“Oh yes, she is,” Matt agreed wholeheartedly. “Want to meet her now?”
My heart leapt.
“Yeah, bring her out,” the stranger said enthusiastically.
“Princess?” Matt called.
I glanced toward the mirror to make sure I looked…well, not presentable. No one could call naked in a pair of kinky panties “presentable.” But I did look hot, and I was plenty fine with that.
The walk down the hall made me giggle, not just with nerves about being handed over like a piece of property, but from the tickly, naughty feeling of the pearls. It would take a tremendous amount of willpower and a lot of careful gauging of my body’s responses to obey Matt’s “no coming” edict.
Matt and the stranger waited in the living room. The moment I saw the man’s face, the voice clicked into place. I knew exactly who he was, and his name was not Dante. I couldn’t acknowledge that because of the resort rules. But he’d been a radio staple for months, with his own singles and features on pop hits.
He wore his hair in thick dreads held back in a headband, and his tight white T-shirt displayed his famously shredded physique to perfection. Numerous tattoos turned nearly every visible expanse of his brown skin into a patchwork art gallery, and his dark eyes drank me in hungrily.
“Excellent customer service. Ten out of ten,” he said, licking his full bottom lip as he studied me from the toes up.
“Nothing but the best for our VIPs,” Matt said with a laugh.
“So, princess. Is that your name or your title?” Dante asked me. It felt weird to hear someone other than Matt call me princess.
“I’m his princess. You can call me Charlotte,” I explained. I wasn’t important enough to need to hide my identity.
“Charlotte,” he repeated, and somehow it sounded like the filthiest dirty talk when he said it. He extended his hand to shake mine, scrutinizing my expression as he said, “You can call me Dante.”
He was, I realized, trying to gauge whether I recognized him as a famous rapper, and if I did, would I break club rules and let on?
I had a great poker face. “Dante. I like it. It reminds me of sin.”
He laughed, a deep, throaty sound that melted my knees out from under me.
“You can have a look at her,” Matt offered, and my face flamed with indignation while my libido surged. “Try her out if you want.”
“But I can’t make her come,” Dante said, clucking his tongue. “If she were mine, I wouldn’t deny her that. I would keep her underneath me all day. She’d come as much as she wanted.”
I squeezed my thighs together, but that only made the pearls pinch my clit.
Dante towered over me. Matt was tall, but this guy probably had a full inch on him. He gazed down and lifted his hand. It seemed to take forever for him to touch me, and when he did, it was with the backs of his fingers, lightly, down my cheek. He bent to my ear and whispered, “Spread your legs, baby girl. I want to see that pussy.”
I let out a shaking breath and shifted my feet apart. He let his hand fall, brushing along my chest and down my breast to cup it. He followed that hand with his mouth, sucking one of my nipples into the hot, soft warmth between his lips. I kept my hands obediently at my sides, but I wanted to hold him there. His tongue was amazing.
Oh no. Oh no. His tongue was amazing.
I was so going to fail my assignment.
He didn’t linger on my tits, palming the other roughly and pinching the nipple before he dropped to his knees. With his big hands on either of my thighs, he parted me with his thumbs, further exposing my clit. One of those thumbs skimmed down, finding my opening. He pushed in a centimeter and hissed.
“Damn, she’s little down here.”
“It’s a tight fit,” Matt confirmed. “But she likes to be filled up. Don’t you, princess?”
“Y-yes,” I stammered.
“And not just there,” he went on. “She’ll take it everywhere.”
Dante looked up at me. His brown eyes were flecked with hypnotic amber. “That true, baby girl? Do you like getting your ass fucked by a big dick?”
“I like getting fucked anywhere by a big dick,” I told him, my voice barely a whisper. I swallowed thickly; any hydration I may have recovered after bondage night was currently exiting my body via my pussy juices. “I’ll like doing whatever you ask me to.”
Dante turned his attention back to my cunt, moving his hand to corkscrew one long finger into me. I squeezed down on it and he groaned a laugh.
“I need to test this pussy out,” he said, getting to his feet again. He unzipped the dark indigo jeans slung low on his hips and pulled out his rapidly hardening cock. He was long and thick and uncut, with a bulging head that would hit all the right places. He turned to Matt. “You mind?”
“Not at all. If you don’t mind me watching,” Matt replied. “I love to see her get fucked.”
“It’s your house,” Dante said, and took my hand. He led me to the couch. I thought he would sit down and ask me to ride him. Instead, he patted the cushion and said, “Get on your knees up here.”
I did, pillowing my head on my arms on the back and pushing my ass out.
“Exactly. You read my mind.” To Matt, he asked, “Condom? No condom?”
“No condom,” Matt answered for me. “Like I said, she likes to be filled up.”
“Good, because I have a lot of tension that needs to be released.” Dante’s statement sounded like it could be a warning to me, or a joke with Matt. I felt the hot touch of Dante’s cock against my slick opening and held my breath. The head popped in, and he stilled. I felt his pulse directly against my G-spot and rocked my hips a little.
“Damn, that’s good,” he whispered, pressing his forehead against my back, between my shoulder blades. “Do you like that, baby girl?”
“I want more.” I pushed back on him, but he pulled out entirely.
“I said I just wanted to test it out,” he reminded me. “We’re going to make this last all day.”
“I think that’s a great idea,” Matt said cheerfully. “In fact, Dante, why don’t you refrain from coming today too?”
Dante laughed. “Edge her all day, while I’m edging?”
“You can come tonight. At her surprise.” Matt paused. “You did get that invitation, didn’t you?”
“I did.” He considered, while I remained bent over the back of the couch, fully on display. Finally, he said, “All right. No orgasms for her, no orgasms for me. What do you think about that, Charlotte? We watch each other get tormented all day?”
“Oh, yes,” I moaned.
He smacked me lightly on the ass. “Then get up. Let’s go make ourselves miserable.”
* * * *
Though Matt didn’t come with us, I still followed his instructions and walked around the resort rather than grabbing a golf cart. It had the intended effect; Dante and I made it all the way down the long path and through the gate with the “Private Residence Staff Only” sign on it before I needed to stop.
“Those are some evil panties.” Dante laughed at me as I leaned against a stone retaining wall and remained cautiously still, breathing slow to get myself under control.
“You’re telling me.” I wasn’t sure how Matt expected me to hold off all day under direct clitoral assault. “At least, you have it easier. All you have to do is not…” I gestured to his obvious erection.
“You think it’s easy for me to watch a naked woman who looks like you walking around in a pair of panties that are going to make her come?” He shook his head. “But in the spirit of fairness, we can go somewhere even more stimulating for me.”
“It’ll be more stimulating for me too,” I pointed out.
“How about one of the pools?” he suggested. “We can watch from the sidelines while people get off and hate them for it.”
When I could safely move again, I asked him, “How are you Dante, if you’re the one leading? Shouldn’t you be Virgil and I’m Dante?”
“You know the reference!” He laughed with an almost childlike delight that was utterly adorable. “Want to know why I picked that name?”
“Sure. Anything to take my mind off these damn pearls.” They rolled and squeezed with every step.
“I studied the literature of the Italian middle ages in Florence when I was doing my master’s. I would have gone with Boccaccio, but people only know Dante.” He shrugged. “And it works at clubs back in the States, since Dante isn’t an unusual name there.”
“I never thought about it, but you’re right.” I scanned my memory. “I graduated with like, four Dantes.”
“Four?” He laughed.
“My high school was huge. We had our graduation in a college football stadium.” I stopped myself. “Wait, we’re not supposed to talk about personal stuff, are we?”
“I never saw that in the rules. But you might know better than me, since you’re a special guest of the owner,” he pointed out.
“If I’m a special guest of the owner, and you’re clearly someone he knows outside of the resort, maybe it’s okay to break this one rule.” At least, one that seemed this relatively minor. “So, tell me about Italy.”
“You’ve never been?” His eyebrows raised.
“Why is that a natural assumption? Is there something about me that seems particularly Italian or Italy-adjacent?” I teased him.
“I figured because you’re with Matt. Rich people always seem to go to Europe.”
“Oh.” I got it. He thought I was Matt’s girlfriend.
Wait. I am Matt’s girlfriend.
“No Italy yet, I’m afraid.” I nudged Dante with my elbow. “But keep talking. It’s helping to take my mind off everything happening between my legs right now.”
“Italy was a lot of fun. Good food, good music. I went to the opera like every week. My master’s is in classical music,” he explained.
Our conversation had brought us down to a main public area, one of the many fountains that served as a zone for public sex. We heard the passionate vocalizations of participants over the sound of the splashing water even before we ducked through the arch in the faux ruins that surrounded it. If voyeurism was a person’s kink, they would get their fill and more at Ascend Red.
That should have been in the brochures. If there was such a thing as brochures for this place. In fact…
“How does one get an invitation to Ascend Red? I mean, without knowing Matt ahead of time?” I asked Dante, unable to take my eyes off a woman who looked like a supermodel getting spit-roasted over the lip of the fountain. The wet slap of her partner’s hips against her ass brought my heart to my throat. I wanted a cock in me, badly. I wanted to get pounded and scream like she was screaming around the cock in her mouth.
“I don’t know,” Dante confessed, and when I glanced over, his gaze was fixated on the same sight. “I got invited because I know Matt.”
Awkward.
“Wait, does that mean I’m going to end up seeing you socially at some point in the future and we’ll have to pretend this never happened?”
“I’m sure we’ll see each other socially back in the real world. But we don’t have to pretend this never happened. Unless you want to.” He reached down and I thought he would spank my ass, but instead he gripped the back of the panties and gave them a tug, tightening the beads against me. I let out a strangled moan of surprise.
There was an empty lounge chair between two occupied ones. Dante gestured to it. “How about we head over there and take turns getting each other way too close while we watch all of this?”
The people in the other chairs seemed to be doing the same thing. Well, sort of. Two hard-bodied white guys who looked like stereotypical gym bros lay together fully naked, one reclining between the spread legs of the other while the partner behind stroked his companion’s cock. On the other side of our chair, another person in a bikini lay as if sunbathing, but the telltale cord of a bullet vibe extended from their swimsuit bottoms.
“You go first,” I suggested, because the sound of so many people enjoying themselves was torture. “Can I suck your dick?”
Dante pushed down his jeans and stepped out of them, stroking himself. “Don’t be too good at it.”
“Denial?” the man jerking off his partner beside us asked with a wry grin.
“Unfortunately,” I responded, sinking onto the cushion between Dante’s legs. I made myself comfortable on my stomach, feet up behind me, before I realized that the rhythmic swing of them in the air was making the pearls do their job even better. I switched to my knees and scooted closer.
The moment my hand closed around Dante’s length, he let out a low curse. “Fuck, I’d love to come in your mouth.”
“Later,” I promised, extending my tongue and running it in a long, slow lick up his shaft from the top of his sack to the very tip of him. “At the surprise party. Which I don’t know anything about.”
“You’re not going to get the information out of me,” Dante warned.
I rubbed my closed, wet lips over the head of his cock peeking out from his foreskin.
“Maybe if you keep doing that,” he revised.
“I don’t want to know anything about tonight.” I let some drool run out on him and slicked it down his shaft with my hand. “I enjoy surprises. I don’t like when they’re spoiled. And it sounds like you’re going to give me a big surprise.”
He grinned down at me. “I’ll give you a big one right now. You just can’t come while you’re riding.”
“And neither can you.” I made a moue of feigned sadness. “Can you imagine how good it’s going to feel when we finally…”
The bikinied guest next to us gripped the edge of their lounge chair’s mattress, hips lifting, toned belly trembling. Obviously, they were coming, but with very little outward show of it.
Dante dove his hand into my hair and tightened his fingers slightly, but he didn’t push my head down. He let out a deep breath and asked, almost timidly, “Suck me?”
I opened my mouth and took him all the way to the back of my throat, watching with pride as his eyes rolled back in his head. I sucked in as I lifted up, and he let out a deep groan. On my way back down, I swirled my tongue, drawing it up the underside of his shaft. Once I’d hit my limit and then some, I choked a little and flexed my throat against his tip. When I came back up, I tasted the satiny, salty wet of his precum. His hand tightened on the back of my head.
“That’s it,” he murmured, eyes closed in deep concentration.
I added my hand to the mix, pumping him between stacked fists while I lavished attention on the head. His hips bucked and another long, stuttering groan pulled from him. I kept going slow and steady, until I noticed his rhythm picking up. Then, I twisted my hands while I stroked and ran my tongue around in steady circles.
“Whoa, whoa,” he said, scooting back while tugging my hair to lift me off him. His cock twitched once, twice, a pearly bead of cum falling from his tip and onto his stomach.
“Too close,” he muttered, scrubbing his hands over his face. “Didn’t come, though. Not all the way.”
“I bet you wish you had,” I teased him.
He peeked at me through his fingers. “If I were you, I wouldn’t be so cocky.”
“Oh yeah?” I challenged him.
“Yeah.” He ran his tongue over his bottom lip. “Because it’s your turn now, baby girl.”