So he sat up, out of her grasp, and pulled his pants together in front while making small talk. “You should go get some more sleep,” he said, “since you’ll need to stay well rested for your upcoming fantasies.”
She sat up beside him. “Do I have any homework this time?”
He held in his smile. It didn’t surprise him to learn Jenna really was a good student—apparently, once she committed to something, even “sex school,” she intended to do a good job. And she was doing a very good job already. “Homework,” he said, pondering it. “Let’s keep this simple. I just want you to think about the various pleasures you experienced last night, and I want you to quit being aghast about it. You did admirably well—you were fucking amazing, actually—but we still have a long way to go and you need to be ready for it.”
Meeting her gaze, he could see his last words clearly concerned her a little. And maybe that was good, given the next fantasy he had slated for her.
“The next one won’t be so soft, sunshine. You should prepare yourself for that.”
Jenna lay stretched out on a wicker chaise on her balcony that afternoon, doing her homework, even if it was all in the mind. But what she kept coming back to was his warning. Not so soft? He’d thought the harem fantasy had been soft?
Well, she understood that in a way—all the female curves, the lulling music, the soft fabrics and equally soft touches—but it had been a lot to handle at once. So it hadn’t felt soft. Utterly seductive, maybe, but not soft. So what was coming tonight?
Although maybe she shouldn’t worry so much about what was coming as what had already been. Concentrate on your homework.
She still couldn’t quite believe she’d fooled around with other girls. Or let them fool around with her anyway—she hadn’t exactly taken an active role. Still, even Shannon had never done that—other than one drunken bump-and-grind fest with a stripper in New Orleans at Kevin’s prodding. Shannon had been red-faced telling her about it afterward, but had finally summed it up with, “What can I say? Something about it was really hot.”
Jenna had concluded that a drunk Shannon was not a great judge of what was hot—but now she got it, sort of. Probably far more than Shannon did, actually. There was a world of pleasures to be experienced out there, and many of them simply weren’t . . . traditional, not what anyone in her suburban neighborhood growing up had been raised to think was normal, by a long shot. But that didn’t mean it didn’t feel good. It had. And she supposed that here, at the Hotel Erotique, it was normal. Maybe Brent really did know exactly what she needed.
So as she peered out over the vast Caribbean waters in the distance, sparkling in the sunlight, she made herself a vow. Whatever was coming, she would take it. She wouldn’t use her safeword. Whatever sex Brent thrust upon her, she would endure it. For him. And even for herself. If she could do what she’d done last night and come out feeling better, stronger, for it—instead of just freaked out and ashamed like she probably would have a few days ago—she could do anything he wanted her to. She would show him just how sexual she could be.
Not that she was sure when this had become about Brent. From the beginning, she supposed, at that first dinner. But if getting a little caught up in him was necessary to make her break out of her sexual shell, so be it. In fact, that was probably the only way this could happen. And when she left here, maybe she’d surprise herself and discover she could have casual sex more easily now; maybe she’d find she could appreciate it solely for the physical pleasure it brought, not the emotional part. Maybe.
Just then, a knock came on her door. She barely heard it from the balcony, but rose on bare feet to go answer. She opened it to find only a small black gift bag, which she picked up and took inside. Reaching into black tissue paper, she found a velvet jewelry box with a white envelope—and being a girl, she couldn’t resist opening the box first.
But, lifting the lid, she didn’t know what she was seeing. The little pieces of silver jewelry came in a pair, like earrings—but they weren’t earrings. Although they were circular, open-ended, and unadorned. She sighed. God, she should have known a box from Brent wouldn’t contain anything simple.
Which left her no choice but to rip into the white envelope, seeking answers.
Jenna,
These are nipple rings, which I picked out especially for you. Presuming you’ve never worn such jewelry before:
1. First, make your nipples hard if they’re not already—although I’ve noticed with pleasure that yours are usually erect.
2. Slide on the nipple ring and overlap the ends, squeezing with your fingers until they’re tight. They shouldn’t be painful, but tight enough to feel them.
3. Wear them until the next time I see you.
Brent
P.S. I hope you weren’t expecting earrings or a bracelet. ☺
Oh boy. Just when you thought things couldn’t get any weirder around here. Nipple rings? Was he serious? Oh, what are you thinking—of course he is.
And, of course, he’d never know if she didn’t put them on yet—she could keep them in the box right up until the next fantasy and he’d never know.
But . . . maybe she was curious.
And maybe she was truly starting to trust him more—at least about what brought her pleasure.
Hell, when else in her life would she have a good reason to put on nipple rings, for heaven’s sake?
So, taking a deep breath, she carried the box into the bathroom to stand before the large mirror atop the sink. Then she reached up, drawing down the straps of the cami she wore and the bra underneath.
It struck her then how everyone had seemed so taken by her boobs last night. They weren’t the perkiest pieces of her anatomy, which had always bothered her, but . . . they were ample and round, with large pink nipples that, as Brent had noticed, often stayed erect whether or not she was consciously aroused. So maybe they were . . . more striking than she’d ever realized.
In fact, now that she thought about it, some of the harem girls’ breasts hadn’t been as firm and porn-perfect as she might have expected, either, so . . . hmm. Maybe it meant breasts didn’t have to be perfect to be appealing.
But she hadn’t come in here just to analyze her tits.
Tits, she thought then, a little surprised at herself. She really had adapted to Brent’s way of talking—shockingly fast. She could only blame it on the aura of lust and debauchery in the air here.
Finally, she reached into the small velvet box and drew out one of the nipple rings—a simple silver circle with tiny round balls on each end. Playing with it a bit, she discovered it was flexible, as he’d implied, and could be adjusted. As usual, her nipples were already pointing prominently, so she slipped the ring on her right nipple, then squeezed it enough to make it cling there.
After which she looked in the mirror, then bit her lip.
I look kinky.
Amused by the thought, she put on the other ring and looked again, unable to deny that feeling kinky was kind of hot.
Although she didn’t think feeling kinky was the sole goal of the jewelry—the idea, he’d let her know, was to be physically aware of it. So she reached up, squeezing each ring a little tighter, until she suffered a soft pinching sensation that echoed through her pussy. That’s when she realized the constant pressure of the rings probably kept a woman’s nipples hard for as long as she wore them. Which likely kept her just slightly aroused for the duration. And that was probably the real purpose behind them.
Hmm. Well, she would see about that.
Jenna waited all afternoon to get a fantasy invitation—but it never came. And the whole while, her nipples stayed beaded tightly in the rings, keeping her very aware of them, making her wish she had Brent here to play with them or suck them like last night.
Finally, she put on a sundress, deciding to venture to one of the resort’s restaurants for dinner. Given that she was at the Hotel Erotique, she wore one of her thinner, prettier bras underneath—and felt unduly sexy to
leave the room with her nipples jutting through the pale blue fabric of her dress, knowing she still wore the nipple rings. Her pussy tingled within her lacy thong—not her usual undies, but another of the items bought specifically for her trip. Her only disappointment was knowing Brent wouldn’t see them.
She chose a casual restaurant located on a deck overlooking the ocean, complete with tiki torches. The sun was just beginning to set as she arrived at the Paradise Grill, and a calypso band played on a small stage in the corner.
It was strange to sit down and look around at the other people—couples, friends, again knowing they were all here for extreme forms of sex. But she felt less embarrassed by it now than she had before.
She drank an erotic rum punch while she awaited her food, having chosen a simple barbeque sandwich with coleslaw and fries. If she had the night off, she was going to be low-key about everything, just relaxing and enjoying the downtime. Even if she continued to remain more aware of her body than usual. She wasn’t sure whether to blame it on the nipple rings or on three successive nights of hot sex. But she tried to take pleasure from the awareness more than push it aside—because that’s why she was here, right? To learn to enjoy her body. And besides, she knew more sex was coming, even if it wasn’t tonight.
The food was good without being too filling, so she indulged in a piece of key lime pie for dessert, enjoying the Caribbean music and the vibrant colors left behind in the sky when the sun sank past the horizon.
When the band played a particularly upbeat instrumental tune, heavy on the steel drums, the lead singer—a tall, handsome black man with a light Jamaican accent—encouraged the crowd to dance. “Up on ya feet—everybody.”
One couple took the floor, then another, soon joined by a group of three girls who looked a little tipsy on their heels but appeared to be having a good time. Probably because Jenna happened to be the only person dining alone, the singer—who bore a striking resemblance to Blair Underwood—wove through the tables to offer a smile as he held out his hand. “Dance with me, pretty lady.”
She instinctively waved him away.
But then he cast a teasing look, an enticing look, and said with that soft island lilt, “Come now, lady—don’t break my heart.” He laid a dark hand across his chest. “Share a dance with me tonight.”
And suddenly it hit Jenna: She wanted to dance with this man. Because it was a beautiful night and a warm tropical breeze wafted over the deck. And because the music was intoxicating and fun. And because she had on a pretty dress and there was simply no reason not to.
So this time she put her hand in his and pushed back her chair. He led her to the dance floor, where she found the beat easy to move to and realized she was truly enjoying herself. A few days ago? She never would’ve done something like this, simple as it was. Maybe with Shannon, but never by herself. She would have feared looking silly, tripping over her feet or dancing badly, people staring. But somehow, now, none of that mattered.
She danced with the handsome man for the remainder of the song, occasionally daring to smile up into his eyes—which were always on her when she checked, it seemed—and when the music ended, he gallantly kissed her hand and said, “Thank you for the dance, my dear.”
A bit flushed but energized from the exertion, she headed back to her table—only to see Brent sitting there grinning at her.
“How long have you been here?” she asked, sinking back into her chair.
“Long enough to see a side of you I didn’t know was there.”
She lowered her chin thoughtfully. “Maybe I didn’t, either.”
“I like it.”
She smiled, feeling a bit self-indulgent. “I think I do, too.”
“I was afraid last night might have sent you swimming for the mainland, but it looks like you survived quite nicely.”
“Oh ye of little faith,” she shot back at him coolly, as if she hadn’t indulged in ultra-kinky, near-orgy type sex last night.
“I have all the faith in the world in you, Jenna. And I’ll have even more if you assure me you’re no longer aghast.”
She tilted her head, weighing how she felt—for some reason, Brent always made her want to be as honest as possible. “Yes, less aghast. Although . . . it seems surreal. Like something I could have dreamed—even though I’ve never had a dream like that before. I guess I’ve begun to learn that . . . I can find pleasure in things I never would have thought possible.”
He gave a solemn but satisfied nod. “Very good, sunshine. And speaking of that, are you wearing what I sent you?”
The mere question made her pussy quiver. “Yes.”
“Good,” he replied simply.
“So . . .” she ventured, “do I have . . . plans tonight?”
He gave his head a short shake, and despite having already feared as much, she suffered a twinge of disappointment. “You get the night off to rest. I just happened to see this vision in blue dancing as I headed home, so I thought I’d stop and say hi.”
She smiled. “I’m glad you did. But where’s home? You live here, on the island, right?”
He nodded. “I have a private bungalow up the beach.”
“Wow—sounds nice. I hadn’t thought about what staff accommodations might be like.”
“Only the other owners and I have houses,” he explained. “Everyone else lives in apartments or dorms, depending on tenure.”
She nodded, then let herself smile in amusement. “Tenure. Who knew the Hotel Erotique thought in such lofty terms?”
He chuckled warmly, but changed the subject. “You will have some more light homework, though. You’ll find your assignment when you return to your room.”
For some reason, that thought actually pleased her, but she didn’t examine why.
Just then, Brent pushed back his chair, clearly preparing to go. “By the way, just because I saw you accidentally tonight, that doesn’t mean you can take off the special jewelry I sent.”
Hmm. “So you’re saying you want me to wear it until . . .”
“Until I see you again. Tomorrow evening.”
He looked arrogantly content with his answer. But her dance with her new Jamaican friend had her feeling a bit bolder than she sometimes did with Brent. “I could just take it off, then put it back on before I see you.”
“You won’t,” he said, completely certain.
She tilted her head. “What makes you so sure?”
“You’re an obedient little student, Jenna,” he said, his voice still all confidence as he met her gaze, “and you do what I say.”
She still wanted to fight back. “Maybe I’ll surprise you.”
“You already have. Every day since we’ve met. But you’ll still do as I tell you.” Then he leaned in and spoke lower. “Because you’ve begun to figure out that I know what I’m doing and that it all brings you more pleasure than you’ve ever known. Plus—you like pleasing your master,” he added with a wink, then stood and walked away.
Dear Jenna,
Tonight and tomorrow, I want you to think about cock. Every cock you’ve ever had, or ever even seen. I want you to think about what a hard cock feels like inside you—in your hand, in your pussy, in your pretty mouth. I want you to think about the way it fills you and satisfies you in a way nothing else can. I want you to let yourself crave it.
And if anything about that is difficult, consider this: A woman’s body was made to take a man’s cock, to want a man’s cock. It’s far more natural to crave it than not to.
Tomorrow, the day is yours. Go to the beach or the pool—whatever you like. But keep thinking about cock. ☺
And be back in your room tomorrow by five.
Brent
P.S. I’d remind you to keep the nipple rings on, but I know I don’t have to, my obedient slave girl.
Jenna followed Brent’s instructions, and such bold, naughty thoughts came more easily than they would have before her arrival here. She thought through the sex partners she’d known in her life—a ha
ndful of guys, all of whom she’d felt deeply about. And she’d loved the way their cocks had felt inside her, yet . . . she’d often felt timid around the appendage, too. It was so . . . foreign compared to anything on a woman’s body. And she’d been utterly shocked the first time she’d seen one—in a movie actually, as a young teenager, with Shannon, who’d insisted on watching R-rated films on cable when her parents were away one winter day.
Of course, she’d long since learned to appreciate the merits of a penis. But the truth was, she’d honestly felt more enamored of Brent’s cock in the few short days she’d known him than in any she’d had before. It was so big, downright majestic looking, like one more ultra-strong, sure part of him. And he used it so damn well, too.
When he’d demanded she suck it in the middle of the night, the command had excited her and she’d instantly embraced her task. Which, now, struck her as odd since going down on a guy had never been her favorite activity. It was something she’d done to please her lovers, and she’d taken satisfaction from their pleasure, but she’d never taken personal , physical pleasure from the act—until last night. She’d wanted to get up close and personal with Brent’s magnificent shaft.
In addition to thinking about cocks, though, Jenna also found herself thinking about breasts, nipples. Her own. She’d felt ridiculously erotic showering in the nipple rings—which seemed content to hug the pink peaks pleasantly tight without ever growing uncomfortable.
And sleeping in them—in a cami and boy-short panties—kept her in a slight but constant state of arousal all night. She had vague dreams—of Brent, and harem girls, and hard cocks—and she woke more often than usual, repeatedly finding herself reaching up to touch, to see if the tips of her breasts were still hard, still encircled, and they always were.
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