Soon, Rylie was spending every night at Sullivan’s place. She was still expected to strip naked every evening after work when she came to his house, but on these hot, humid nights her nudity frequently led to more joint skinny dipping in the pool, followed by wild bouts of dripping wet sex.
As summer went on, she was happier than she’d been in years. They had fallen into the habit of cooking dinner together before settling down to work, with Rylie often wearing nothing but an apron he gave her that left her breasts peeking out at the sides and her bottom completely exposed. The narrow ties hanging down from the waist in back seemed to be there only to encourage his fingers to roam down the cleft between her butt cheeks.
One hot night they went for a dip in the pool as soon as they got home from work. Both of them were still naked when she headed into the kitchen afterwards and put the apron on. Sullivan smacked her bare ass as soon as she turned her back on him. Laughing, she chased him into the living room brandishing a wooden spoon. She caught up with him, putting him on the floor with a sweeping roundhouse kick that knocked his legs out from under him. With a muffled oath, he pulled her down beside him. They wrestled on the floor until he grabbed the spoon from her, pulling her across his strong thighs and spanking her with it playfully until she promised never to use her martial arts skills on him again.
Then, while she lay giggling across his lap, he worked the ties of the apron down, pulling them tight between the cheeks of her ass. She gasped and he immediately followed with his fingers, sliding them down to tease her tight bottom hole. Rylie froze. He hadn’t played with her ass since the night he made her wear the butt plug while he spanked her. She’d been so embarrassed by her shamefully indecent behavior that night that she was almost grateful that he hadn’t repeated it. But sometimes, when he took her to that place where she was screaming with pleasure, she secretly wished he would play with her like that again.
* * *
Sullivan knew her so well that when her body stiffened, he realized immediately that she was torn with shame by her hidden craving for what he might do next. He remembered her wild, frantic response the last time he’d engaged in ass play with her.
“What’s the matter, Rylie?” he asked, his finger probing insistently.
“Please, stop.”
“Stop what?”
She shuddered as he slid his finger deeper.
“Stop doing… that.”
“Do you like it?” He shifted her body, spreading her legs apart to allow him easier access.
“No.”
He pulled his finger out and swatted her ass twice, hard. “Don’t ever lie to me, Rylie. You can say you’re ashamed, or uncomfortable, or nervous. But don’t try to tell me you don’t like it when I play with your ass. Your body is telling me you do, in spite of your embarrassment. Now, I’ll ask you again—do you like it?”
She buried her face in her arms, muffling her response.
He slid his finger in again. “I didn’t hear you.”
“Yes, I like it but… it hurts a little,” she murmured.
He stopped and got to his feet, pulling her with him. “I can fix that,” he announced, taking her hand to lead her upstairs to the bed. “Lie down on your stomach,” he said, rummaging around in the drawer of the nightstand.
She stood there, acting nervous, and Sullivan realized she needed him to take over, to be her dom and make her do all the things she secretly longed to do. He looked at her, naked and beautiful, waiting breathlessly for him to take charge, and felt the switch trip inside, the one that triggered his own wild desires.
“Come here and get on your knees first. Stroke my cock.”
Rylie knelt in front of him, hands trembling a little. He was already rock hard and her touch made him hungry for more. “Take it in your mouth. Lick it and suck it while I tell you what I’m going to do to you tonight.”
He saw her shiver, felt her lips, wet and hot on his cock. “That’s right. Just the head. Take it in your mouth… and imagine how it will feel when I slide it in your ass.”
She moaned and sucked harder.
“You’re going to put two pillows in the center of the bed and lie down on your stomach on top of them. Then I’m going to spank you good and hard for not obeying me right away. After that, I’m going to tie your hands together and spread your legs apart. I’m going to play with your ass tonight, any way I want, until you’re begging me to put my cock in you there. If you don’t, I’ll have to start all over, spanking you again even harder.”
She moaned again and opened her mouth wide, flicking her tongue over the head, licking down the shaft before taking him in.
“That’s it, baby,” he crooned, grabbing her head to shove himself deeper inside her mouth. “Now—get up on the bed.” His voice was low and rough.
Rylie moved quickly this time, piling two big pillows together, then arranging her body over them to lift her bottom high in the air. He stood for a moment, stroking his hard-on, enjoying the sight of her virgin ass willingly getting into position for him to thrust himself inside it for the first time. He’d make it good for her. His pleasure would come from her pleasure, the passionate cries she’d make as he drove her to orgasm in a whole new way.
He waited a few extra seconds, knowing the delay would only increase the heady mix of anxiety and anticipation she was feeling. Then he climbed up on the bed.
* * *
Rylie was shaking all over, barely able to stay in position. She was terrified of what was to come, yet more aroused than she’d ever been. It really was going to happen. He was going to fuck her in the ass whether she liked it or not… and she knew there was nothing she could do to stop him.
She heard the smack of his hand on her ass first, felt the fiery sting a millisecond later. Then the two became impossible to separate—the sharp crack, the lick of flame fusing together as he spanked her over and over with the flat palm of his hand. But with this spanking, the promise of what was to follow made her pussy wetter with every firm whack. When he stopped and pulled her wrists together to tie them in front of her with a narrow scarf, she was so overcome with dread and desire that she almost wished the spanking would continue.
He knelt behind her and pushed her legs apart. She resisted a little, only to have him smack the tender insides of her thighs. “Spread your legs for me,” he demanded.
She complied and the next instant his tongue was roaming over the hot flesh of her well-spanked bottom. Rylie jerked and was rewarded with another sharp smack. “Do I have to tie your legs up too?” he growled. “You know the rules. Now don’t you dare move.”
She shivered uncontrollably, forcing herself to stay in place as his mouth resumed its journey, tracing the stinging marks his hands had made with licks and hot kisses. When he dipped his head and she felt his tongue rimming her ass, she clenched her fists together, stiffening her whole body.
He stopped. Rylie heard sounds behind her but didn’t know what he was doing. Then she felt his hands, rubbing some sort of lube all around her tight hole. One finger dipped inside, teasing. His other hand reached down to fondle her clit, stroking it until she cried out.
“Open up for me, Rylie. Relax and let your body respond the way it wants to.” All the time, he was working his finger deeper inside her ass, probing arrogantly, relentlessly, while he rubbed her clit, bringing her to the edge of orgasm.
She couldn’t help it. She started bucking against his hand, moving her hips back to take him deeper inside. He worked a second finger into her tight hole. “That’s it. You know you want it. Now ask me. Ask me to put my cock in you.”
Rylie stopped thinking, stopped worrying about how shameless she was acting. She thrust herself back against him. “Yes. Yes, I want to feel it. I’ve never had it before and I want it. I want you to fuck me in the ass.”
She moaned when he withdrew the probing fingers. A second later, she felt his hand guiding his thick cock to her tight opening. He stroked her up and down, dipping into her pussy, t
hen back to her ass, rubbing himself all around her while coating his stiff length with more lube. She felt him, impossibly large and hard, pressing against her, and froze again.
“Let go, Rylie. I’m going to fuck your ass now, just like you asked me to, and there’s nothing you can do to stop me. Let go—and I’ll make sure you enjoy it.” All the while his cock kept up its powerful assault, slowly, relentlessly, forcing her open. He reached down with one hand to massage her clit again and when she moved instinctively, he rammed the head of his cock through her tight opening.
Rylie screamed, more in shock than pain. Sullivan kept still, fingering her clit until she felt her tight passage beginning to relax around him, so hard and thick inside her. He moved then, just a tiny move, sliding his cock further in, withdrawing a little, only to go a fraction deeper. Rylie moaned, and rocked against him. He picked up the pace, thrusting harder each time, while keeping up his assault on her throbbing clit.
She squirmed around, got her hands under her for leverage and ground her ass back against him. Sullivan made a noise deep in his throat, grabbed her hips with both hands and rammed into her. When she screamed again, this time a cry of savage pleasure, he exploded. She felt his cock pulsing in her as she collapsed.
Later, much later, as she lay in his arms, he whispered the question. “So—do you like it?”
She was sure he already knew the answer, but she gave it to him, bold and uninhibited for once. “Yes. I love it when you play with my ass, when you fuck me in the ass,” she announced. “Will you do it again sometime?”
He laughed and nuzzled her neck. “Only if you beg me.”
* * *
Occasionally they managed to get some work done at home, but Sullivan seemed to find plenty of reasons to bend her over his lap and paddle her on a regular basis. Those sessions usually ended with Rylie crying out in pleasure rather than in pain. Although it took a great deal of soul-searching, along with the ability to be brutally honest with herself, she had come to accept her dark desires, her newly discovered submissive side.
Rylie still dreaded the pain of the spankings, but she had stopped denying the fact that positioning herself across his lap or being commanded to get the hairbrush sent a shiver of indecent lust through her. She loved his domination. She loved it when he took control. And once the spanking began and the endorphins were flowing, the licks searing her ass awoke savage desires inside her, desires she’d never felt before. Sullivan fed on her hunger, driving her even more frantic with need, then taking her to new heights.
Rylie did her best to squelch sentimental daydreams. She tried to take things one day at a time with Sullivan, with no expectations of where this relationship was going. But it was hard not to imagine a future with Sullivan. Along with the raw passion, he brought out a carefree, playful side in her that she’d buried long ago. When they were at home, he was warm and caring, honest and giving. At work, he’d fallen into the habit of seeking her opinion on nearly every matter that came up. It reminded Rylie of the way her parents had been—business partners, lovers, best friends. For the first time in her life, she began to hope that she’d finally found the right man.
Incidents like the one that happened at work a few weeks ago only cemented those feelings. One afternoon when Sullivan was out of the office on appointments, she walked past the door of the conference room. Ashlaigh was in a meeting with one of the firm’s long-standing clients, a member of what Rylie thought of as the ‘good ole boy’ network. He’d come to Sullivan and Sons after attending a cocktail party at one of the high-rise apartments where Ashlaigh had done the interior design work. Currently in the middle of a bitter divorce, he wanted to hire her to decorate his new bachelor pad.
The snippet of conversation she heard stopped her dead in her tracks.
“Whatta ya say, Ash, honey? Can ya meet me there after work tonight? If things go well, I’ve got plenty of friends who’d just love to have someone decorate a little getaway in the city for them too. Your boss would be mighty pleased if you brought in all those new accounts.”
Rylie knocked briskly on the door and popped her head in without waiting for a response. “Hello, Mr. Clayton. I hope Ashlaigh is taking good care of you.”
“Rylie, it’s nice to see you again. Darlin’, I swear I don’t know how that ole dog Neill gets any work around this place, bein’ surrounded by such beautiful women all day long. Why, Ashlaigh here is so distractin’, I’m thinkin’ I need to forget all about furniture and such and just have her and a big ole bed installed in my new condo.”
Rylie shot a quick glance at Ashlaigh and saw her wince. “Now, Mr. Clayton, you’re making Ashlaigh uncomfortable with remarks like that. Ash, why don’t you fill me in a bit on what you two have come up with so far?”
Ashlaigh was in her usual garb. Today it consisted of a bright pink thigh-length tank top over a short black and white print skirt, worn with pink cowboy boots. Obviously frustrated, she ran her fingers through her hair, where new purple highlights matched the purple polish on her nails.
“We’ve been talking about the overall theme for Mr. Clayton’s new place,” she began, only to be interrupted.
“Ashlaigh’s been givin’ me plenty of wild ideas.” Clayton leered at her suggestively. “But I was just tellin’ her I think we need to have our next meetin’ on site—so I can really get a feel of things, if ya know what I mean.”
“Mr. Clayton, Ashlaigh is a valued member of this firm and I expect you to treat her with respect.”
Clayton’s leer turned to an angry scowl. “Oh, come on, darlin’. I’m not suggestin’ anything y’all haven’t done before. Everybody knows what goes on in this company. I mean, why else would Sullivan hire a girl who looks like this…” He waved an arm at Ashlaigh, then at Rylie. “Then you come to work here, after what happened at Judson’s place.”
Rylie’s voice dripped ice. “After what happened at Judson’s place? What exactly are you referring to?”
“Well, that whole mess with you and the board members. It’s all over town, darlin’. You can’t expect to screw two different men on the same board of directors and not get fired.”
“Mr. Clayton, it’s time for you to leave. This firm will not be working with you—or any of your cronies, for that matter.”
Clayton stood up, his face red. “Who the hell do you think you are, missy? My company has done millions of dollars’ worth of business with Sullivan and Sons, ever since Neill’s daddy started the place. And if I want a personal favor or two from one of his little office girls in return, well, he owes me that much.”
Rylie reached for the house phone. “Leave now, before I call security and have you escorted from the building.”
“You can’t dump me,” Clayton raged. “When Neill finds out what you’ve done, you’ll be out on your ass.”
“I’ll take that chance,” Rylie shot back. “Now I suggest you leave, before I decide to put you on your ass.”
“You’re gonna be damn sorry. You haven’t heard the last of this.” Clayton stormed out of the office, slamming the door as he went.
“Thanks, Rylie.” Ashlaigh sighed. “I’ve never had anyone treat me like that before. He made me feel like I was some kind of whore kept on Neill’s payroll just to make the clients happy. But I know he’s been a client of Sullivan and Sons forever. I was trying to fend him off without insulting him. I wish I’d been able to handle it better.”
“He’s scum, Ash. There is no ‘handling it’ with men like him.”
“I hope Neill doesn’t get angry with you over all of this.”
“If he does, he’s not the man I thought he was,” she replied.
Later that afternoon, Rylie nabbed Sullivan as he walked in the door. “Can I have a few minutes of your time?”
“Sure, no problem. What’s up?”
“If you don’t mind, I’d like Ashlaigh to join us. We had an unpleasant incident earlier today with Mr. Clayton. I know he’s already called twice and I want you to he
ar about it from us before he blindsides you.”
Sullivan called Ashlaigh to his office and Rylie was in the middle of recounting her story when the intercom buzzed. “Mr. Sullivan, Thomas Clayton is here and he insists on seeing you,” Jean said.
He glanced at Rylie and she nodded her head. “Fine, Jean, send him in.” Before he hung up the phone, his door burst open.
“Sullivan, I don’t know what kind of operation you’ve got here.” Clayton glared at the two women seated in front of Sullivan’s desk. “…but these gals seem to think they’re runnin’ the place. This one—” He gestured to Ashlaigh. “Well, she came on to me, actin’ like she’d sleep with me if I gave her the job. And this other one…” His voice dripped with scorn as he deliberately turned his back on Rylie. “She had the nerve to tell me my business wasn’t wanted any more. She threw me out!”
“Tom, Rylie tells me you made sexist remarks to Ashlaigh and then insulted both of them. Is that accurate?”
“Now, Neill, I didn’t say anythin’ they haven’t heard plenty of times before. They’re askin’ ta be treated like that. I mean, look at both of ‘em. Dressin’ like sluts, runnin’ around in those short skirts and fuck-me high-heel shoes. Besides, I heard all about your new lawyer from a couple of Judson’s board members.”
Sullivan’s voice was dangerously calm. “Oh, really? What did you hear?”
“She got down on her knees plenty after hours in the boardroom. I heard it firsthand from a couple of ‘em. Too bad it couldn’t save her job. I figured you’ve been takin’ advantage of her talents since you hired her right after. Hell, who could blame you?”
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