The Story of Owen: One Man's Submissive Journey

by Claire Thompson

  Owen laughed, shaking his head. “No, no way. I’m not into that humiliation shit.”

  “You’re into whatever Mistress tells you you’re into,” Jerry rejoined with a sly wink. When Owen didn’t reply, Jerry prodded, “Okay, so what goes on? You’ve been to see her, what, twice now?”

  “Yeah, and I have a session scheduled for this Friday. I can’t wait.” Owen took another swig of his beer, smiling at the thought of soon seeing the gorgeous and sexy Mistress Sylvie. After their last session, he’d barely been able to contain himself during the cab ride from the Village to his apartment on the Upper East Side. Moving in a daze past the doorman, he’d used his briefcase to hide the erection that refused to subside.

  Once in his apartment, he hadn’t even bothered to take off his pants, instead just opening his fly and pulling out his hard, aching cock as he flopped onto the sofa.

  Staring out at the Hudson but seeing only Mistress Sylvie, he’d stroked himself, too turned on to worry about the tender, abraded skin of his freshly-whipped cock and tortured balls. He’d come fast, jerking and shuddering as his jism shot onto the glass coffee table in front of the sofa.

  “Jeeze, Owen, are you going to make me wheedle every sentence out of you?” Jerry’s impatient voice pulled Owen from his reverie. “Come on, spill the beans. I want to hear it all.”

  Owen looked at Jerry, wondering at his own hesitation. Since college they’d always shared details about their love lives or lack thereof. Jerry had been his best friend and confidant during Owen’s protracted divorce to a woman he never should have married in the first place. Why was he hesitating now? This wasn’t even a relationship. It was just a business transaction, as Jerry had reminded him.

  Shaking away his reticence, Owen leaned forward, talking softly though it was unlikely anyone would overhear them in the noisy, crowded sports bar. “It was fucking amazing. The first session she cuffed me to a St. Andrew’s Cross and worked me over pretty good with a single tail.” Owen left out the small detail of his premature ejaculation, nor did he disclose the anal probing. “The second time she used a wicked little cat o’ nine tails on my cock, after locking my balls in a steel ball stretcher.”

  “I knew it!” Jerry crowed. “I knew you’d fucking love it. I can’t believe you waited this long to finally find out, Owen. Now admit it, is there anything more powerful or sensual than kneeling naked at your Mistress’s feet, your skin just aching with the need to feel her whip, her cane, her open hand?”

  Owen sucked in his breath. “That’s it exactly, Jerry. The aching need.” He hugged himself, digging his fingers into his triceps, trying to control the physical longing Jerry’s words had engendered. “The sting of the leather woke something in me that I can’t stop thinking about,” he admitted. “The way she flicks her wrist, her eyes glittering as she whips me, her nipples like points under her sheer blouse, her hair flying—it’s like—it’s like, I don’t know. Like what I always dreamed heaven would be, I guess,” Owen finished, embarrassed to realize he was gushing.

  Jerry gave Owen a long, appraising look. “It sounds to me like you’re not only smitten with the experience, but with the woman herself.”

  Owen started reflexively to deny it but bit his lip instead. Jerry knew him too well. He shrugged unhappily. “I know that’s stupid. Someone that gorgeous is sure to be in a relationship. And anyway, she’s a pro. She’ll give me exactly what I pay for, and not a thing more.”

  “Hey,” Jerry said, offering an encouraging smile. “That’s not necessarily a bad thing, especially at this point. You’re still exploring your kink and figuring out what works for you. There’s plenty of time for a romantic relationship down the road. Trust me on this.”

  Owen nodded, though he wasn’t altogether sure he could separate his heart and mind so easily.

  Jerry signaled the waitress for two more beers and returned his focus to Owen. “So what’s on the agenda for the next session? Do you get to, like, fill out an order form, checking off what you want?” Jerry held an imaginary pen in his hand, making check marks in the air. “Twenty licks with the riding crop—check. An over the knee bare-ass spanking—check. Nipple clamps—check. Pony whip stuck up the ass while permitted to worship Mistress’s pussy for hours—check.”

  Owen laughed, pushing away the sudden, hot image of Mistress Sylvie naked and lying back on a bed, her legs spread, her luscious cunt exposed for Owen to lick and worship. He cleared his throat. “Uh, no. No checklist. Mistress Sylvie calls the shots. There was an interview process, and I did complete a detailed checklist about my likes, dislikes, hard limits and stuff like that, but no, during the actual sessions, she tells me what to do, and I do it.”

  “Or else.” Jerry grinned.

  “Yeah.” Owen snorted but then sobered. “No sex. You know the deal. She’s not a prostitute, she’s a pro Domme. She’s introducing me to submission. She’s testing my measure as a masochist. But like you pointed out up front. It all comes for a price.”

  “Comes for a price. Good one, bro.” Jerry guffawed and Owen forced the grimace on his face to become a smile.

  Chapter 5

  Owen was surprised but pleased when the door was opened, not by Isabel, but by Mistress Sylvie herself. “Good afternoon, Owen,” she said in her pretty accent. “Isabel has the day off.” Mistress Sylvie was wearing form-fitting pants and a vest of smooth black leather. The leather looked so soft and inviting it was all Owen could do to keep from reaching out to stroke it. The tops of her creamy breasts were pressed together, creating a deep cleavage. Her feet were housed in the same black stilettos he’d been allowed to kiss at the end of their last session.

  She turned away while Owen dropped his envelope onto the silver tray. “Follow me,” she said. But instead of leading him up the stairs, Mistress Sylvie led him past the sitting room and into the office where he’d first met her. Beside the desk stood a slender rod of black steel soldered to a flat platform base. It had what looked like ankle cuffs attached near the bottom of the rod, and at the top was a kind of vise apparatus with wing nuts on either side.

  Mistress Sylvie leaned against a corner of the desk, her cool green eyes fixed on Owen. “You’re forgetting yourself. It doesn’t matter what room you are in. When you are in my presence, you are to be naked.”

  Owen glanced anxiously at the open door. What if someone else were to come in? He looked back at Mistress Sylvie, who was tapping her foot and frowning. He would have to trust her. Owen reached for his tie, pulling it free. He stripped quickly, and knelt on the carpet in front of her, his cock already rising.

  “Do you know what that is?” Mistress Sylvie pointed to the steel apparatus.

  “No, Mistress.”

  “It’s a cock and ball pillory,” she said. “It’s adjustable for the height of the user. The vise at the top is called a ball crusher, and with good reason.” Owen stared at the equipment with wide eyes. He began to sweat just looking at the damn thing. Was he really up for this? Could he handle it? Mistress Sylvie let her words sink in a moment before adding, “I think of it more as a little jail for your cock and balls. As long as you stay in position, it won’t hurt you. But if you move…” She let the sentence trail away.

  Lifting herself from her position against the desk, Mistress Sylvie walked toward the device. Looking down at Owen, she asked, “Are you familiar with the term predicament bondage?”

  “Yes, Mistress,” Owen replied, his heart lurching into gear.

  “I find it’s an excellent training device. Teaches discipline and endurance. Puts you, what is the expression in English, between a rock and a hard place, yes?” She laughed a small, musical laugh, but her eyes were flashing. “However you move, or don’t move, has consequences. Get up. I’ll show you.”

  Owen stood, his now fully erect cock leading the way as he approached the pillory. “Stand on the platform,” Mistress Sylvie directed. She crouched on the other side of the device. Adjusting the height of the cuffs by means of a small le
ver on the side of the rod, Mistress Sylvie closed the metal cuffs around Owen’s ankles and then adjusted the height of the pole, positioning the vise at the top so it was directly aligned with Owen’s cock and balls.

  Gripping his shaft with one hand, his balls with the other, she pulled his genitals forward into the vise. “Don’t move,” she ordered.

  Owen watched with nervous anticipation as Mistress Sylvie turned the wing nuts on either side, which slowly closed the metal vise until he was trapped, the metal bars pressing snuggly against the base of his cock on the top and beneath his balls on the bottom. It didn’t hurt as long as he stayed on the balls of his feet. Owen was strong, his legs toned from years of swimming and running, but he knew he couldn’t stay indefinitely in this position.

  “Hands behind your back,” Mistress Sylvie ordered. She moved toward the desk and retrieved what Owen recognized as his leather cuffs from her dungeon. Moving to stand behind him, she cuffed his wrists at the small of his back, which forced his chest to thrust out so he was standing at military attention.

  Mistress Sylvie sat at her desk, her eyes sweeping Owen’s naked body, lingering on his captured cock and balls in their ‘little jail’. Owen felt extremely vulnerable, at once ridiculous and deeply aroused in his precarious position.

  “I have a few things I need to attend to,” Mistress Sylvie said, pulling a folder on the desk toward her. She reached for the pen that lay beside it and opened the folder. With a casual glance his way, she continued, “You will stand at attention until I’m ready for you. I won’t be too long.”

  Though the room was cool, Owen felt a prickle of sweat at his armpits. He pulled lightly against his wrist cuffs and flexed his calves, though he remained on the balls of his feet. The vise was tight around his cock and balls, which pulsed and throbbed. He wondered how long he could stay in this position.

  A passage from The Story of O came into his mind—when Sir Stephen is sitting at his desk, reading or on the phone, Owen couldn’t precisely recall, and he casually whips the naked O, who is bent naked across his desk, mostly ignored by him. Owen understood now, on a personal level, just what the author had described O as going through, at once humiliated and thrilled by the objectifying situation.

  Though it had been years since Owen had thought about that defining book, he had read it several times as a teenager, keeping it hidden beneath his mattress and pulling it out late at night, imagining himself as a male O and Sir Stephen as a woman. Though he’d been dismayed by how cold and uncaring Sir Stephen behaved throughout the novel, the story had still given him plenty of fuel for masturbation, not that it took much for a perennially horny seventeen-year-old.

  While Mistress Sylvie stared down at her papers, occasionally marking something on the page, Owen seized the chance to look at her. He guessed she was in her late twenties or early thirties, though he was never very good at guessing ages. Her skin looked dewy soft and he flexed his fingers behind his back, wishing he could stroke her cheek, imagining the feel of her soft lips against his, knowing this would never happen.

  His calf muscles were starting to ache, and Owen experimentally lowered his heels to the platform. “Ah.” The word was pulled from his lips without his meaning to make a sound as the vise tugged painfully on his balls with just that slight movement. He rose again onto the balls of his feet, the sweat now breaking on his upper lip.

  Mistress Sylvie looked up. “Stand tall, if you know what’s good for you.” She smiled cruelly and returned to her work.

  Several more minutes passed. Owen’s right calf suddenly cramped and he shifted reflexively to ease it. “Ah!” he cried, louder this time, as the vise tugged hard against his cock and balls. He looked down. His genitals were purple. How long could he safely stay in this thing? He looked to Mistress Sylvie, who was watching him with those green eyes, her expression inscrutable.

  “Does it hurt?” she asked a low, silky voice.

  “Yes, Mistress,” he replied.

  “Good. Pain is good for the soul. Go flat on your feet.”

  “What?” Owen’s heart was beating too fast. He licked his lips and tried to swallow but his mouth was too dry.

  “I said,” Mistress Sylvie repeated in a hard voice as she stood, “Go flat on your feet. Do it. Now.”

  Owen took a deep breath and forced himself to obey her. As he lowered himself, the vise tugged painfully at his cock and balls and he groaned. Mistress Sylvie was now standing directly in front of him in the narrow space between the desk and pillory. He could smell her perfume and his own sweat. Her hand went to his tortured genitals and he could feel her fingers stroking his cock and balls, compressed and throbbing between the bars of steel. He groaned again, though this time with lust.

  “Are you prepared to suffer for me?” Mistress Sylvie whispered close to his ear.

  He was suffering already, but her words sent a jolt of sexual heat through his blood, making his tortured cock throb even harder, if that was possible. “Yes, Mistress,” he breathed.

  She stepped away. “You need to be punished for failing to strip immediately when you entered the room. Back on your toes.”

  Owen rose on the balls of his feet, sighing with relief as the intense pressure on his cock and balls eased. His hair had fallen into his eyes and he tried to shake it away but it was wet with sweat and didn’t cooperate. He watched as Mistress Sylvie opened a drawer of her desk and withdrew some items.

  She held up a black chain with clamps on either end. He recognized what it was from sex videos he’d watched online. Clover clamps, the kind that tighten when pulled. He bit his lip as she approached him with them.

  “You belong to me,” she said softly, as she ran her hand over his chest, pressing her open palm against his left nipple. “Your heart is beating so hard for me. You are my slave, my possession.”

  The words reverberated through his head, filling him with a longing that was almost painful in its intensity. He wanted that. Oh, Jesus God, how he wanted that. And for this session, for this purchased time, he was just that—her slave, her possession.

  If only it didn’t have to end…

  He was completely distracted from his hopeless musings when she compressed one of the clamps and then let it close over his left nipple. It took a second for the pain to register, and then it flooded his nerve endings, making him gasp. She did the same with his right nipple and then lifted the chain to his lips.

  “Bite the chain. Don’t let it go, no matter what I do to you. Do you understand?”

  “Oh, god,” Owen murmured, barely able to hear her over the pounding of his heart in his ears.

  “That is not an answer!” Mistress Sylvie said, her eyes sparking. She slapped his cheek, though her touch was light, more to reprimand than to hurt.

  “Yes, Mistress,” Owen hurriedly replied between labored breaths. His nipples were on fire, the pain for the moment distracting him from the clench of metal against his cock and balls. Mistress Sylvie pressed the chain to his lips and Owen let them part and then bit down. The resulting pull of the clamps at his nipples made him groan through clenched teeth.

  Returning to the desk, Mistress Sylvie picked up a riding crop, the leather dyed blood red. “Remember,” she admonished as she returned to him. “No matter what I do, you keep that chain in your mouth, and stay on your toes.”

  She reached for his face and for a split second Owen thought she was going to slap him again, but instead she smoothed the matted hair from his eyes. Her touch was surprisingly gentle, her fingers cool against his heated forehead.

  “And now,” Mistress Sylvie dragged the folded rectangle of leather at the end of the crop handle down Owen’s chest, “it’s time for your punishment.”

  ~*~

  Sylvie felt the gentle throb between her legs. It had been a long time since a client had excited her as Owen did. He was so responsive! The way his eyes widened, the way he trembled, the way his cock surged toward her, the way his heart pounded against her palm.


  Something about him reminded her of Jacques, though they looked nothing alike. Maybe it was his yearning, the achingly sweet longing to submit that radiated from him like a force field that reminded her of her old lover. She liked Owen’s smell, too, a strong, earthy male scent. Was he married, she found herself wondering, and then shook the thought away. What did it matter? She never pried into her clients’ private lives.

  Focusing, she stepped back, examining Owen’s cock and balls with a critical eye. She was always careful not to keep them shackled in the vise for too long, not wanting to cause any permanent damage. But she hadn't screwed the vise too tight for Owen, aware from his interview that he was a virgin in the area of cock and ball torture. He should be fine for at least another thirty minutes in the pillory, though she probably wouldn’t keep him there that long anyway, just to be safe.

  By his powerful reaction, he was clearly deeply excited by the scenario she’d laid out for this session, and she didn’t want to make the mistake she’d made sometimes early on in her career as a pro Domme, of ending a scene too early. His cock was as hard as the steel pillory rod he was shackled to, and for a brief, absurd moment, Sylvie imagined straddling that hard cock and riding herself to orgasm.

  “Ready for your punishment?” she said softly as she stepped behind him.

  “Yes, Mistress.”

  Oui, Maîtresse.

  He even sounded a little like Jacques, with his rich baritone, made breathless by his predicament. Unable to resist, Sylvie placed her fist lightly into the hollow just below Owen’s right hip, which was emphasized by his firm, rounded ass. He had the body of a Greek Adonis, muscular and lean. If she owned him for real, she found herself thinking, she would keep him naked while at home, save for a collar around his neck.

  Sylvie saw that Owen’s hands were clenched into fists. “Relax your hands,” she said, waiting until he complied. She started lightly, tapping his ass with the crop, enjoying the sound of the leather smacking against his skin. His body was glistening with sweat, and the setting sun outside the window made it seem as if he were glowing.