Chapter 9

Luke looked so masculinely pretty laid out naked on her plush beige carpet, fingers wreathed behind his head looking like he was lounging there. Only the tension in his muscles gave away that he wasn’t just relaxing, cock up in the air like a thick, long flagstaff rising from the nest of dark curls. Well-trimmed curls, she noted. Olivia did appreciate a nice cock with good grooming and Luke had both going for him. Somehow she wasn’t surprised.

He was watching her with a hot, excited gaze that made her even more aroused, seeing how focused he was, watching him holding himself still as he waited on her. Olivia was rather enjoying making him wait too, not just to draw out the tension (although that was very nice) but because she appreciated a good, buff, naked male on her rug. The time Luke spent being hands on with his contracting business showed, not just in the callouses on his palms but in the broadness of his shoulders, the definition of his biceps as they flexed on either side of his head, the definition of his pecs, and the ridges down his stomach.

“Bend your knees,” she murmured, nudging his legs into place. 

It only took a few moments for her to arrange him exactly how she wanted him. Hands behind his head, knees in the air, feet planted on the floor… impossible if she was going to ride him, and the sadist in her enjoyed the disappointment in his expression. What the position did do was give her a bit of access to his fantastic ass.

From his survey, Olivia knew his ass was entirely virgin, but like most Dommes she loved ass play. The three Ps: Plugs, Probes, and Pegging. That was how she thought of them. Most men didn’t even know how much they were missing out on when they refused to let their ass be part of the sexual equation, but anyone Olivia played with found out real fast. With her fingers if nothing else. 

“Good,” she said approvingly once he was in position, bending at the waist to give his straining cock another stroke as a reward and also—not incidentally—a peek at her lacy black bra as the front of her shirt gaped. Luke groaned, pushing up off his feet so his hips and ass lifted. Chuckling, Olivia let go of his cock. “Now stay right there, I just have a couple things I want to grab.”

Giving him a wicked smile to meet his incredulous look, she quickly turned and made for the kitchen. Behind her, Luke groaned and there was a soft, muffled thump as he dropped his head back down on the carpet to wait on her.

Like any good dominant, Olivia could easily come up with quite a few pervertibles—everyday items which could be made kinky. However, she didn’t want to keep Luke waiting for too long, and she didn’t want to dive right into anything too hardcore, so she just plucked a couple ice cubes from the freezer and dropped them in a bowl to carry, a rubber band from the drawer, and then swung around to the desk where she kept a small tube of lube—it wasn’t just Boy Scouts who could be prepared—on her way back to Luke’s supine form. His cock was still fully erect, and Olivia let out a small sigh of appreciation for hot, obedient men.

******

While Olivia had been gathering whatever it was she was gathering, Luke had rested his head in his hands again, the way she’d wanted him to. He felt oddly vulnerable, just lying there in wait for whatever she was doing, his legs spread and knees pointed to the ceiling.

He was starting to feel like a broken record, as Olivia kept putting him in positions he’d never been in before. At least he wasn’t required to admit his inexperience to her.

Waiting wasn’t exactly easy, mentally, but he sure as hell wasn’t going to disappoint her on something so simple. When she came back into the room and he turned his head to look at her, the satisfied smile on her face made the wait worth it, even if he did feel a little twitchy. In some ways, it would have been easier if she’d tied him down—then he wouldn’t have had any choice but to wait. Now he understood what Liam and Hilary had meant when they’d told him about honor bondage and why Liam felt it was more powerful than actual ropes or cuffs. It took a lot more effort on the part of the submissive to not move.

“Very good, cupcake,” she said, kneeling down gracefully between his spread legs and setting down the bowl she was carrying. “I bet it was hard not to move.”

“A bit,” he admitted, and then groaned as she took his cock in her hand again, pumping the straining organ. His hips pushed up, seeking more of the stimulation, only to be pulled back down when her other hand grasped his balls and tugged—not entirely gently. Pained pleasure shot up his spine as his ass thudded back down on the carpet. Olivia rolled his balls in her hand, squeezing just hard enough to make little beads of sweat pop out on his forehead, his fingers gripping each other beneath his head to keep from reaching down and trying to protect his jewels—and yet his cock was harder than ever. “Fuck!”

Olivia chuckled as he started to pant, one hand still working his cock, the other squeezing and rolling the tender balls in his sack. It felt almost too painful to feel good… almost. But because her careful movements never quite crossed the line to actually hurting, it felt fucking phenomenal.

When she released both hands at once, Luke cried out. His balls were aching pleasantly from the rough play, his cock throbbing with the need to cum.

She was definitely a sadist.

Something wrapped around his balls, right where they met his body, and held. Not tightly. Just enough that he could feel it. Very gently. A sharp contrast to the way she’d just been manipulating his poor sack.

“What’s that?” he asked. 

“Just a rubber band,” Olivia said, stroking his sack with careful fingers. “It’s only doubled over so it won’t restrict your blood flow much—just enough to make your balls a little more sensitive.”

Luke regretted asking. Her tone implied she was saying something reassuring, but putting ‘rubber band’ and ‘your balls’ together in the same sentence just sounded fucking terrifying. Letting out a small laugh at his expression, she flipped open the cap on a little tube she’d brought over, which Luke quickly realized was lube as she spread it on her fingers. 

Wrapping her hand around his cock again, she began to stroke with her now slippery palm. 

“If you don’t like it, all you have to do is say ‘red,’” she practically purred at him, working her hand up and down his dick. Luke whimpered.

That felt… incredible. The band around his balls didn’t hurt, but it did seem to amplify the sensation of her slick hand pumping on his dick, the brush of her fingers from her other hand over the already sensitive skin. And when her slick fingers from the hand not around his cock began to rub lube on the crinkled star of his ass, his hips bucked and his balls bounced, sending little starbursts of sensation through him. Pleasure? Pain? He wasn’t even sure anymore.

Her finger slid inside of him, her other hand giving his cock long, slow strokes through her slick grip, making him tighten in both discomfort and erotic bliss. Fuck… that felt better than he’d imagined.

Full.

Invasive.

A slight burning as the ring of muscle at his entrance was stretched.

Intimate.

Hot pleasure.

Her finger slid deeper and his cock strained upwards again, his eyes closing and expression tightening as he tried to assimilate all these new sensations. He was squirming both mentally and physically, but he didn’t want her to stop either. It felt too good. When her finger pumped, he moaned. It probed and he shuddered. She found a spot inside of him and he let out a strangled cry at the intense ecstasy that followed as her finger stroked. Her thumb pressed down on a spot on the base of his cock, stopping the orgasm that had almost materialized.

“Fuck… fuck… fuck…” he panted.

“Bad boy,” she purred, her hand screwing on his cock in a twisting motion that had his body bowing. “I didn’t say you could cum yet.”

The full feeling in his ass receded as she removed her fingers, leaving him feeling empty, disappointed, and maybe a little relieved at the short reprieve. 

There was a small clinking sound and then suddenly something freezing touched the tiny bundle of nerves and Luke cried out, jerking as it pushed inside of him. If it wasn’t for her hand still stroking his cock, he probably would have popped right up like a jack rabbit but… 

Cold liquid dripped from the entrance of his ass, her finger pushing the cube in deeper as he twisted and clenched. It was so fucking cold… so why did it feel so fucking hot? 

******

The tight grip of Luke’s virgin ass around her finger trembled. His cock was rock hard, practically pulsing in her palm, and she could see the struggle on his face as she played with his ass.

The desire. The reluctance. The pain and pleasure. The fight to remain submissive and let her do as she pleased with his body.

When he slumped, another moan sliding past his lips, Olivia felt the rush of adrenaline and erotic power that came from dominating another person. Because that person was Luke, the rush felt even more powerful, more intimate. Something she didn’t want to dwell too much on right now.

“Good, Luke,” she said, pumping her finger. The ice made his tight channel cold, which would both enhance and numb some of the sensations. At least until it melted completely and the inside of his body began to heat back up. His cock jerked in her hand, heavy and hot, and Olivia had to resist her own impulse to climb on and ride her way to glory.

Damn but she wanted him inside of her… 

Not yet though. Not tonight. Even though his Stronghold survey had indicated he was open to sex during the class, if the two of them were really going to do this, Olivia wanted to take her time. Sex might indicate a willingness on her part to jump right into a relationship, making unspoken promises she wasn’t ready to commit to yet. 

But that didn’t meant they couldn’t do other things. 

Giving Luke’s cock and ass one last pump, Olivia stood, her hands and fingers sliding away from him and leaving him panting for breath. 

A small smile on her face, she rose above him and started to strip.

Laid out in front of her, Luke’s cock had turned a dark pink as it strained for release, his balls a little darker as the rubber band around the base of his sack constricted blood flow just enough to make it extra sensitive. She could tell he was struggling to keep his hands in place behind his head—which was why she had put them there. The placement actually made it a little easier for him to hold position than if he hadn’t had something to hold on to.

Seeing the desire flaring in his eyes as she stripped down, taking her time to shuck off her shirt and pants, then her matching lace bra and panties, was more than a little satisfying. His cock bobbed as his lower muscles clenched in response, a visceral reaction she luxuriated in.

“Lower your arms to your sides,” she ordered. As soon as he did so, she planted one foot on either side of his head, enjoying the way his expression lit up, his eyes most definitely not fixed on her face. From his position, he’d mostly be able to see her pink pussy, fringed with neatly trimmed dark red curls and the triangle of hair she preferred on her mound.

Olivia knelt down, one knee on either side of his head, her pussy hovering inches above his lips. She could feel his hot breath panting on her sensitive folds, his blue eyes almost incredulous and wild with excitement. 

“Okay, cupcake,” she said, smiling down at him. Her hands gripped his hair firmly, pulling his head up to meet her lowering cunt. “Show me what you can do.”

She didn’t object when his hands came up, arms curling under her legs and then over to hold her thighs. The hold gave him a little more leverage to reach her—and she liked the way he felt, clinging to her legs to please her. She sighed with blissful enjoyment as she felt his tongue sliding through her folds, tasting her… learning her… flicking against her swollen clit so that she pressed down more firmly against him. 

From the way he’d been looking at her, Olivia doubted he’d ever had a woman riding his face quite like this… His own cock unsatisfied and straining while the cold remnants of an ice cube trickled from his clenched ass, a rubber band wrapped around the base of his balls to keep them sensitive. All of which she ignored entirely, making him wait for his orgasm while he tongued her to hers.

“Oh yes…” she moaned, arching her back, her breasts thrusting out as his mouth worked. 

He definitely did know what he was doing, already adjusting to the subservient position she had him in—and when she moaned her appreciation, his efforts redoubled, his hands tightening down on her thighs, helping her to hold in place over his lips. Luke was a pleaser, and the more she wriggled and verbally encouraged him, the more excited he became. He licked and sucked, alternating between the two, paying attention to her sensitive lips and clit, finding all the ways she best liked to be orally pleasured.

“Yes… oh yes… just like that…” Olivia had already been pent up from watching him with Lisa earlier that evening, then further aroused by playing with him herself, knowing she was the first to breach the virgin territory of his ass, watching him submit to her. She hadn’t been far from orgasm to begin with.

One hand still in his hair, gripping and tugging as she worked her pussy over his mouth, she brought the other up to pinch and roll her own nipple, giving her just that little bit of extra physical stimulation she needed. Luke sucked her clit into his mouth. Hard. 

“Fuck! Yes!” She threw her head back, grinding her pussy down on his face, shuddering, thighs quivering from the effort of holding herself up as she came. Hot bliss spread through her body, radiating out from her core where Luke’s tongue was lapping up her cream. She rode out her orgasm, through the large waves of rapture down to the smaller quakes as her body expended the sexual tension that had been building.

Her hand gentled on Luke’s hair, stroking and smoothing as she lifted her pussy away from his mouth, feeling his hot breath again as he panted for air. 

“Good boy,” she murmured, running her fingers through his hair in a caress. “You deserve a reward.”

******

Oh yes, please, for fuck’s sake.

He couldn’t quite form the words though.

It felt like his entire body was quivering, overwhelmed by sensations and experiences he’d never anticipated. Never prepared for. The ice in his ass had fully melted while he’d been eating her out, cold liquid trickling down his crack and onto the carpet beneath him. That might have made him feel odd and uncomfortable, but he’d been far too distracted by the aching need in his cock and balls, Olivia’s gloriously naked form, and the sweet scent and taste of her pussy.

The image of her rocking above him, breasts jiggling, pale pink nipples bobbing, arched in ecstasy, was going to be burned on his brain. Since he’d met her, it felt like he was constantly garnering new material for his fantasies.

When Olivia knelt down in her previous position again, his entire lower body throbbed in need.

“Hands behind your head,” she reminded him in a murmur, running her own hand appreciatively down his stomach, her arm brushing against his cock. Fuck it felt like his balls were going to explode.

Gentle fingers stroked… pulled… and then the rubber band was off of his sack. 

Luke hadn’t thought it had made that big a difference. He’d felt the hold but it had been so gentle. Now his balls started tingling, flickering with little sparks of painful sensation that made it feel like his skin was crawling and he did his best not to writhe as it hit him, gritting his teeth against the agonizing pleasure of it.

Then she poured what must have been melted ice in the bowl on his sack and he screamed.

Freezing burn. His balls tightened, tried to shrink… but her hot mouth was sliding down his cock and he twisted, completely confused about what he was supposed to be feeling. It hurt, he knew it had hurt, but right now it felt like the pain was good and up was down, and the silken glide of her tongue over his swollen shaft was so pleasurable it was almost too intense and he thought he might be in agony.

He didn’t even recognize the animal sounds coming from his throat.

And when her fingers slid back into his ass, stretching, seeking, probing, and finally pressing against the sensitive spot she’d found earlier, he actually howled.

Her hot mouth slid away but her hand wrapped around his slick shaft, expertly pumping, her fingers thrusting inside of him, curling and rubbing. Then she sucked his cold balls into her hot mouth and the juxtaposition of temperature had him writhing.

His hands were no longer behind his head, they were digging into the carpet on either side of his hips as he gasped for air. Liquid spewed from his cock, spattering on his stomach, and he didn’t give a fuck because he was so lost in the ecstasy, the agony, the thunderous sensations overwhelming his body and blanking out his mind.

After that, things became a little muzzy. Later he would dimly remember her wiping him down with a warm cloth, cleaning off his stomach from the sticky cum he’d blasted all over himself. He’d remember her gentle hands on his cock and balls, running the cloth between the cheeks of his ass. But in the moment, it was almost like he blinked and then they were both on the floor, with her leaning against her couch and his upper body curled around her like she was his favorite teddy bear, his head resting on her bare breasts.

Which was not a bad way to come to, but he was a little shaken at how he’d completely lost control of himself. 

Somehow, she seemed to realize when he was regaining his full sensibilities again.

“How are you feeling?” she asked, her voice carefully neutral, her fingers stroking through his hair. 

“A little weird,” he answered honestly. He felt… overwhelmed. Like so much had happened that he had to take in that he couldn’t quite handle all of it. Too much information to assimilate in too short a period of time.

But it had felt so good while it was happening.

He felt the rumble of her chuckle through her chest.

“Here, drink some water,” she said, picking up a glass from the coffee table and making him wonder when exactly she’d gotten that. But he did as she said, sitting up just a little bit but not relinquishing the arm he had wrapped around her body or his position leaning against her. He wasn’t going to give that up until he had to, no matter how confused—and maybe a little conflicted—he felt right now. Once he’d gulped some of the cold, clear liquid, which tasted strangely delicious, Olivia handed him a piece of chocolate. “Eat too. That’ll help. Things got a little more intense than I anticipated.”

Well at least he wasn’t the only one thrown off, then. That was reassuring. It made him feel a little better. Olivia didn’t sound off balance, exactly, but maybe just a little unsure of herself. Which made him feel just a little bit more sure of himself. 

“That was…” His voice trailed off as he groped for the right word. The right phrase. Either option eluded him completely. 

“Enjoyable, hopefully, at least,” she said, joking a little. 

Luke snorted, but sounded distant. His brain was fuzzy, but he knew the truth. “That’s an understatement.”

“Good.”

“It was also not what I expected.” Despite himself, Luke found the hand not wrapped around behind her back drifting towards his own back, towards his ass. Trepidation, uncertainty welled.

He felt Olivia’s reaction, more than saw it.

“Mmm. Something you should know if you’re serious about wanting to get involved with me, if you want to go beyond this—I’m absolutely going to want to play with your ass, and eventually use my strap-on.” She sounded so gleeful when she said it, Luke’s cock twitched a little.

But he still couldn’t shake his apprehension either.

Yes, he’d put he was open to anal play, etc. on his survey. But for some reason he hadn’t expected to actually like it. Definitely not to the point he had. He knew it didn’t make him gay or less of a man, but for some reason he still felt like he wasn’t supposed to have enjoyed having her fingers in his ass so much. Wasn’t supposed to feel his cock twitch at the thought of her pegging him. He didn’t even know why he felt like it was okay to tolerate or participate in the activity, bearing it because it was what she wanted, but it was somehow wrong for him to actually find pleasure in the act.

His head was all sorts of fucked up right now though. Was this the subdrop she’d talked about in class? 

Luke tightened his arms around her. The confliction he was feeling confused him. He wanted Olivia, and he’d loved what they’d just done, but…

He wasn’t even sure he could explain it. For some reason he felt very vulnerable and exposed, not just to her but to everyone.

After all, Olivia was a Domme. Luke hadn’t fully appreciated until just this moment what that meant. Not just that she would boss him around in the bedroom, but the full scale of what she wanted to do to him… everyone would not only know what she was doing, they’d be able to guess at most of it and they’d know how much he liked it.

And it was fucking with his head.