Filthy Cowboy

by Amy Brent

  “Try telling that to my parents,” she said. “They still think I’m a stupid fourteen-year-old who has her mind in the clouds thinking that she can model. What do they have against you, anyway?”

  He darkened a bit, a combination of embarrassment and anger. “My ex-wife. She says that I beat her.”

  “Did you?”

  “Not exactly.”

  She blinked at him, wondering what on earth he could possibly be talking about. He tilted his glass down his throat and gulped it down. “What the hell,” he said, finally, his voice harsh from the wine. “It’s not like we’re going to fuck tonight, anyway, right? I mean, you’re probably still a virgin, right?”

  She blushed. Now it was her turn to be embarrassed and angry. “What’s it to you if I am?” she demanded. “Just because I have standards for the men that I will go to bed with doesn’t mean that I’ll never sleep with anyone.”

  He leaned back and studied her for a minute, debating whether to tell her. Then he said, “I know what the stories are about me, but I didn’t beat my ex-wife. But my sexual tastes run into the realms of the—shall we say, perverse.”

  “Oh my God, you’re not into children are you?” she asked—a bit too loudly, it seemed, because all of a sudden he seemed to panic and tried to shush her. Fortunately if anybody noticed they at least had the decency to ignore her remark.

  “No, no—nothing like that. I mean things like—well, blindfolds, whips, handcuffs—that sort of thing.”

  She had to stifle a giggle when she heard that. For some reason she always associated “handcuffs” with “pink fuzzy things that never really locked” and it just seemed absurd imagining him with them, his arms above his head—probably getting tickled with a feather duster. “Sorry,” she said. “It’s just—not something I’d expected to hear from you.” He was her father’s age, after all—granted, he was far better-preserved than her father had ever been—and for some reason she never thought of older men as being into anything kinkier than maybe having the woman on top.

  He shrugged, relieved that she wasn’t going to blurt out any more incriminating insinuations about him. “I am what I am,” he said, stopping one of the waiters and pointing to the bottle on her cart. She poured, and when she walked away he continued, “My ex-wife thought she would be into it, but when push came to shove, no pun intended, I hurt her—that part is true. But it was always part of the game, you see—for people like me, pain and pleasure go together. Our pleasure is heightened when there is an edge to it. It transcends the act of sex and turns it into an—well, an experience, to put it mildly.” He was getting excited as he spoke and she could feel herself getting drawn into his words, her curiosity making her wonder if maybe she could have done it, after all. When she’d been looking into doing pornos the guys who directed those kinds of videos had surprised her when they said they didn’t pay—they didn’t have to, they explained. Women actually paid them, and that had never made any sense to her—they were getting penetrated, shocked, chained, bound, and gagged—why suffer all the extra humiliation if they weren’t paid? But now that he’d explained it to her she began to wonder if there wasn’t something else to it, after all. “You have to know what you’re doing and know your limits and trust your partner completely,” he said, now, looking into her eyes. “There’s an element of faith involved—there’s no middle ground, no ‘I’ll trust him if’. You’re either all in or all out.”

  “You must really need to know someone before you try that,” she murmured. Strangely, she found herself thinking, I could trust you. But why was that? She’d only just met him—objectively there was no reason for her to trust him, other than that he seemed to be, well, trustworthy. But unlike her parents, he didn’t make her feel like an idiot, he didn’t twist her words to mean what she clearly didn’t—he respected her enough to take her opinions seriously, even if they didn’t always agree. As a case in point: another bottle of wine and another plate of tapas floated by—crispy eggplant, covered in aioli sauce.

  What the hell, she was thinking. It wasn’t as if she would ever model again—at nineteen, she was officially “middle-aged” as a model, and if she reached twenty-one without obtaining supermodel status the most modeling she’d ever do would be as one of the nudes for the art department at Montco. And what the hell, too: her parents would be furious with her anyway for going on a date like this—she might as well give them a reason to be infuriated. It was a shitty reason to have sex for the first time—but at least he would know what he was doing, which was more than she could say for any of her other dates.

  He sighed and continued, “And then there are people who aren’t wired that way—for them, pain is just pain. There’s no pleasure in it, and no matter how much they want it they just can’t feel it, you know? My ex was one of those. We tried for six months—and then she filed for divorce, and the rumors began. I spent a small fortune settling that—and, well, my reputation has never recovered.”

  “That’s hardly fair,” she said, sympathetically.

  “It is what it is,” he said, popping a crumb-covered fried mushroom into his mouth. “But that’s why your parents don’t like me, and truth be told, I wouldn’t approve of you dating me, either. I’m quite the disreputable charmer, according to those who know.”

  “So charm me,” she said, “if you can.”

  “Are you sure?” he asked. “The kinds of role-play I like aren’t for virgins who have yet to discover what turns them on.”

  “I haven’t had sex yet,” she said, evenly. “That doesn’t mean I don’t know what turns me on.” It was a lie—she didn’t know what she wanted just yet—but she did know that his description of pain and pleasure had excited her curiosity like nothing else.

  He frowned at her, studying her. “You have to want it because it’s what makes you happy,” he said. “I can’t give you that.”

  “Then teach me,” she said.

  “All right.” He reached under the table and rested his hand on her thigh, tracing his thumb back and forth across the tender skin on the inside of her thighs. A shiver ran through her, and from it, came a tiny little spark of anticipation.

  His hand moved slightly higher up her thighs, but his thumb was still making that slow sweep back and forth, back and forth, setting off tremors of anticipation all over her skin—but just when she was getting turned on by it—just when she could feel herself getting wet and hot—he stopped.

  “What—” she began, her voice hardly more than a whisper.

  “Rule number one,” he said, softly. “You can always say ‘stop’. It won’t always be that word, exactly—but when we get to my house we can pick a safe word. Until then, though—if it ever gets to be too much, you can always say ‘stop’, and I will stop, and I’ll bring you home, and we’ll never speak of it again.”

  “Got it,” she said, wishing he would resume.

  “Rule number two,” he continued, “total honesty. I will always tell you what I’m going to do to you—but it is up to you to tell me what you think is all right.”

  “I can live with that,” she said, and then she felt his hand work her skirt up all the way. She gasped—not at the embarrassment of being exposed like that—there was nobody to see, not where they were sitting—but at the suddenness of it, the audacity the man had. And what she felt was glee.

  “Rule number three,” he said. “Complete submission. As long as I tell you what I’m going to do and as long as you say it’s all right, you must obey me. Even if it means getting down on your hands and knees, right here and now, and blowing me in front of the entire restaurant.”

  “Do you really want that?” she asked.

  “No, but I do want to cut those spaghetti straps, so that the only thing between you and a public indecency charge is that bolero that doesn’t quite close all the way.”

  She looked at him, feeling as though it was some kind of test. She had no compunctions about showing off her breasts—she’d modeled half-naked before, an
d between the lighting guys and the cameras and the makeup crew modesty was one of the first things to go on set. But here—this was a restaurant. He was right that the bolero would keep her breasts covered, but neither did she want to spend the entire night worrying about a nipple accidentally popping out.

  “Not here,” she said, finally. “The company’s too nice.”

  “But elsewhere?”

  She nodded. He raised his hand for the check—and then she wondered what she’d gotten herself into.

  He took her to a movie theater. It was pretty crowded, being Friday night, and the movie wasn’t anything remarkable, something about a boy and his dog. But no sooner had they taken their seats when he leaned over and whispered, “Now, I want to cut the straps of your top.”

  She nodded, feeling a tightness coiling in the pit of her stomach. He pulled out his pocketknife and sliced through the straps, and reached through her bolero and pulled the sequined top down to her waist. Nobody seemed to notice—the seat backs were relatively high and when she threw a discreet glance sideways the young couples on either side were too busy kissing and making out to notice. As soon as the cold air kissed her breasts, she shuddered—and realized that she was completely at his mercy. All it would take was a single flick and she would be exposed.

  “Put your head on my chest,” he whispered, as the movie started.

  She did as he told her. It felt nice, to have his heartbeat in her ear while the movie began—and then his hands began toying with her breasts, his fingers gently squeezing her nipples, nearly making her cry out with an odd sensation of pain and curiously intense anticipation. She felt her hips begin to grind into the seat, almost of their own accord, and then he whispered, “I want to touch you. I want to feel that moment you become wet, when you become a woman under my hands.”

  “Okay,” she whispered.

  She could feel his arm snaking around her body, and his hand snaked its way down her skirt and cupped her pussy. “So smooth,” he breathed, “so soft.”

  And then his fingers resumed squeezing her nipples, extracting little bolts of lust from her and all of a sudden one of them went straight into her crotch and it took everything she had not to cry out as she felt wetness soak his hand, her panties, her skirt. “Taste yourself,” he said, now, moving his fingers to her mouth. “One at a time, don’t get greedy, now—yes, just like that—”

  Salty-sour-sweet—and the skin on his hands were so soft, she’d give anything to be touched with those hands again. “Silent,” he whispered, as a whimper rose in her throat. “If I hear a sound out of you I strip you naked right here.”

  She clenched her teeth as he touched her pussy again, this time reaching between the folds until he found the little swollen bud of her clit. Her entire body clenched and coiled as the need built up, like water building up behind a close hose. If he didn’t let her go it would explode out of her—

  “Yes,” he whispered. “You want to cry out, don’t you?”

  She could only nod, the tears in her eyes blurring the image on the screen—she thought she could hear people snickering at her but in the darkness of the theater she could see nothing. Then he whispered, “Do you want to come?”

  She had only a vague idea of what was meant by “coming”—something with a lot of screaming—but it was exactly what she wanted to do. She nodded.

  “Then come with me, let’s go home.”

  ***

  She’d thought he meant back to her home, but at some point in the dark she realized that he’d taken a turn into the rural countryside; that part of the East Coast had some houses dating back to the colonial days, and she soon found herself outside an old-fashioned colonial house, three stories, with a wraparound porch. It looked like a smaller version of a plantation house, and before she could say anything he said, “I wish I could say it dates from the Civil War. As it is, I just paid a very good designer very much money to make a very good mock-up.”

  She stepped out, aware that her tits were flopping about all over the place, wondering if he’d meant for her to cover herself up. The fabric brushing against her nipples would not allow her to forget that she was nearly half-naked. And you’ve only just met Jack and you know he’s into BDSM and you’re going into his house. How does this end well, again?

  The living room was nice enough, the space clean and modern, but the furnishings curvy in a nod to the faux-antiquated design of the house. “You have a nice house,” she said, as he went to the drinks cabinet. He looked at her questioningly. She nodded—a little liquid courage never hurt.

  “Thanks,” he said, as he poured out her drink and handed it to her. “Any second thoughts?” he asked, pushing aside her bolero and taking a look at her tits. “It’s now or never.”

  “If I back out now my parents will never let me hear the end of it,” she said, looking at him over the rim of her glass. “So never it is.”

  “That’s not a good enough reason to want this,” he said.

  “You promised me I could come,” she said.

  “So I did,” he said. “But you’ll live without it—and with any amount of luck, you’ll soon have a twenty-something who’s hotter than fuck at your beck and call—so why me?”

  “You said you knew what you were doing,” she said, starting to feel a little uncertain about this, now. Of course he had to make sure she really wanted it—but it just seemed cruel, now—dangling the promise of a sexual experience like none she’d ever had before, and then taking it away just because he chose to be careful. She was the one being reckless—shouldn’t her opinion count for something? “And I want to feel like I did in the movie theater—I want to feel like—you’re taking care of me,” she added, haltingly. “Like you know who I am on the inside and you don’t care that it’s not perfect.”

  He nodded, and took a sip of his whiskey. “Then we’ll start you off with something light,” he said. “You will strip naked in front of me, and I will put you in this dog collar, and we will go down to the basement, where I have my little, ah, playroom.”

  She gulped. But he’d already seen and touched her—any pretense at modesty now would be hypocritical. “And then?” she prompted, mostly to buy herself a little time to work up the nerve to strip in front of him.

  “And then I will chain you, and whip you with a riding crop. We’ll stick with something simple—if it ever gets to be too much you can just say Coca Cola and we’ll end it, okay?”

  She found herself nodding helplessly—part of her realized that this was incredibly stupid, trusting a guy she’d only known for three hours to whip her until she came. But that was exactly what she found herself wanting, and as she faced him and took off her bolero top the quivering excitement in the air was palpable, now.

  “Fuck,” he murmured, as she peeled off the sequined top, and then worked her skirt over her hips. “I knew you were hot—but this—”

  “I take it you’re happy?” she murmured, smiling.

  “No speaking,” he snapped. “You’re mine, now, mine to do with as I please, do you understand? You don’t do anything unless I permit it, and you don’t speak except to answer my questions. Keep your eyes on the floor.”

  She licked her lips but did what he said, feeling the first pangs of humiliation running through her—the first twinges of doubt. “Now,” he said, as she took off her shoes and worked her panties off her hips, “I know it’s rather disconcerting being a submissive for the first time. You still want to have some control, but that’s the whole point of submission—surrendering everything, trusting entirely—”

  “How can I get past it?” she asked.

  “Embrace it,” he said. “Suffer. And live.”

  It seemed a little odd to her, but as he pushed her down to her knees and put a dog collar on her she began to feel a little better about it all, strangely enough. She was already naked, what more could being on her knees do?

  He led her down the stairs, through a gap in the shelves. The room he’d prepared was small
but it was clean and brightly lit—and there was an apothecary dresser, with its dozens of little drawers, standing in one corner. He pulled her over and took out a pair of handcuffs from one drawer, and a pair of leg irons from another—and two long steel chains from a third. Did all of the drawers have something kinky in them, she wondered, as he cuffed her hands together and raised them above her head, hooking the cuffs to one of the eyelets in the ceiling, and then spreading her legs apart and shackling them to the floor.

  “Comfortable?” he asked.

  She nodded.

  He hit her.

  Not very hard—her cry was more from surprise than from pain, because it was where the smack was that was so shocking, a long, sharp stroke up the inside of her leg. She hadn’t noticed the thin, flexible rod while he was chaining her, so the touch came as a pure surprise, not the least because it left behind a tingling sensation that somehow worked its way deep inside her--

  Again—this time closer to her pussy. This time the tingling went deeper, and this time she found herself craving the next stroke even as she writhed from the initial sting. He was an artist with the rod, knowing just how hard to hit and where to hit and how long to wait—

  Again—and she let out a groan as it smacked her right between her legs, kissing her clit with a sharp sting and then leaving her own body to work itself into a frenzy of pleasure—but this time he didn’t wait: he hit her again, and again, and again—almost letting the pain dissipate between each smack but not quite, so that even as the pleasure became more and more intense so too, did the pain, and as she cried and moaned and screamed he stepped into her and kissed her with a fierceness that matched her own. She felt his hands stroking her breasts again, and as he squeezed her nipples she felt herself clenching around his tongue, which only seemed to excite him more.

  “Make me hard,” he said, letting her arms down and pushing her gently to her knees.

  She gulped and whispered, “I don’t know—”