Filthy Coach: An Older Man Younger Woman Romance

by Amy Brent

  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, and 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—”

  “Just like in the movie theater,” he said, stepping out of his pants. His cock was before her, shining and gleaming and impertinent in its erection. “What you did with my fingers—taste—”

  She got the idea, even though his fingers were smaller. She licked it tentatively at first, wanting to please him, and she felt his hands clench her hair with glee. I can make you do things, too she thought, and she sucked on him just a bit, watching his body twitch. A little harder, and he began to swell inside her mouth, tasting strangely sweet as his cock pulsed inside her. A little more, and there came an animal groan from his throat and she was not the least bit surprised when he pushed her to the floor and thrust himself inside her—

  It hurt, like no other pain she’d ever experienced—a searing, tearing kind of pain, and yet when he pulled himself out she wanted nothing more than it for to continue, because with the pain came a brilliant, scintillating ecstasy that made her cry out and whimper. It changed as he thrust inside her, each thrust bringing another wave of pleasure mixed with pain, and each time the pleasure became greater and greater, each wave higher and higher—and when she let herself go and rode it, it felt like nothing she’d ever had before. “Thank you,” she heard herself whispering, as every nerve in her body quivered and sighed with relief. Relief that it was over, relief that it felt so good.

  She’d once thought that keeping the things Jack did to her at night a secret would be hard, and sometimes it was: sometimes her nipples were so sore from the night before that she could hardly stand the feel of a t-shirt over them—which wasn’t a problem on the weekends (Jack didn’t demand that she be naked but he did like it, and she liked to please him) but during class it was all she could do not to squirm, and she knew that some of the younger men snickered at her for not wearing a bra sometimes. But for the most part what took place in the basement, as they worked their way through the various clamps, vibrators, blindfolds, straps, chains, and ropes that were in that chest of drawers, was easy to keep secret, because it was something that she didn’t want to share with anybody.

  It was an odd arrangement when she thought about it, which wasn’t very often, nowadays. Six months after that first date, she had her own room in his house, and her own car to take to and from classes. He paid for her classes at MontCo. She even managed to find a modeling agency that was not too far from Jack’s house, and even resumed modeling. It wasn’t glamorous work, to be sure—mostly catalog work—but it paid enough for her to pay for her own gas and go shopping and get her hair done—all the little things that she felt weird asking Jack to pay for, even though he probably would.

  But what was their relationship? The question of whether she was a whore used to bother her immensely—there was no question that he was willing to keep her because she was willing to let him fuck her thirty-six ways from Sunday. But at the same time, she liked it—she liked pleasing him, she liked what he did to her, and she even liked him. They’d once spent a morning at the National Smithsonian discussing the virtues that got Michael Jackson’s glove into the exhibits but not David Bowie’s Ziggy Stardust outfit. He’d discuss business with her over dinner; she’d talk about her classes and how eerily similar programming and coding was to languages. And no matter how long the day was, how tedious their lives were, she would wait in the basement on her hands and knees for him every night, the collar around her throat, hoping that she could please him.

  Was this love? It certainly felt like love, but she couldn’t deny that her parents—when she spoke to them, which wasn’t very often—had a point: what would happen to her once the sex stopped? What would happen if he truly hurt her? What would happen if she did refuse him? “It’s only love until you say, ‘No’,” her mother had said over the phone, haughtily. But that was
the thing—he’d never, not once, asked her to do something that she would refuse. There was no real way to talk about how safe he made her feel, even as he nearly exposed her in public, even as he made her writhe on the floor in a strange combination of agony and ecstasy, and so she never tried to defend him—not that she had to. Her smiling, beatific presence by his side at corporate gatherings, next to all those hawkish forty-something wives who’d spent years stifling their own desires and snuffing out those of their husbands, was enough. She was young and pretty and they were happy together. “They just can’t stand to see people happy,” Jack would murmur after those nights.

  “My father was there,” she said after one such gathering. “He didn’t seem to approve.”

  “So fuck him,” said Jack. “The people who want to tear us apart are the ones who can’t get what we have.”

  But how do you know? She lay next to him, wondering if her parents had really been unhappy, and how they’d masqueraded such an appearance of bliss—and why they went to such lengths. “Truth be told, I feel bad for them,” he said, now. “They think that if they play by the rules, ‘work’ on their relationship, that makes happiness—but happiness is really just dumb luck, just like success—”

  “Hey,” she said, turning to face him. “That’s funny, coming from a self-made guy like you.”

  “If we’d been having this talk fifteen years ago, I’d have agreed,” he said, rolling onto his back, and she followed him, running her teeth over his nipple making him draw in a sharp breath and arch his back. “Ooh, you naughty little vixen,” he murmured, sliding his hand between her legs now, pressing on her until she quieted, becoming still. “Fifteen years ago, I’d have said that I did everything to get myself into the top law firm in the area, and that I was the one working my ass off to make partner. And that’s still true. But now I realize just how lucky I was: I got into and out of law school when it was still possible for lawyers to find a job, when going to a mediocre law school wasn’t a demerit on your resume but something that could be overcome with a shit-ton of hard work. I was lucky to be born into a race and gender which is universally favored by law firms. And above all, I was lucky enough to have had a summer job caddying for Jordan Wexler, the owner of the firm. We all get lucky,” he said, moving down to suck on her nipple. “Some of us just get luckier than others.”