Caging An Associate

Austin arrived at his parents' Westchester home for Sunday lunch to hear his uncle angry at his mother. "What do you mean she didn't give you a key?!" They stopped discussing whatever that was about when they saw him come in and greeted him warmly.

His mother asked how work was going and Austin's response was uncharacteristically timid. "Pfft! You've had a great start at Braddon," Warner reassured him. "Just great!" Austin had been bred to have confidence but impostor syndrome could affect anyone. Had he just got the job because his uncle was the head of the company? Some of his fellow new associates, not to mention the more senior lawyers, seemed much sharper than he felt, especially Claire, his French contemporary whom he had started dating a few weeks prior and who had enchanted him. It wasn't just her intelligence and quick wit, but her steely determination that set her apart in Austin's view.

"Ohhh Claire," Warren mused. "Yes we're very lucky to have her. And so are you! But you're both so focused on your careers at the moment, don't expect anything too serious. It's a cliche, but don't put all your eggs in one basket. She's going to Denver this week, right? You should go out on a date, spread your wings, build your network. I know a few eligible bachelorettes if you want me to hook you up, daughters of friends at the country club, some real well-bred and good-looking young ladies.

"As for your work, you may not have my last name but never forget that You. Are. A. Braddon. It's in your blood. You know the ins and outs of this company better than many partners, and we'll have you locked up in their ranks before you know it."

Austin assured his uncle he could manage his own dating, and to placate him Austin called a friend from high school whom he knew had moved to New York recently to try to get into publishing. They met for drinks Wednesday evening, but Austin didn't feel a spark and he cut the evening short at 10pm, hoping he could meet up with Claire, who was due back at around midnight. She got his message when she landed but replied that she was too tired, and that she'd make it up to him later in the week.

The next day at work, Claire had a glow and walked with an extra strut, reporting that the Denver trip had been a great success, and Austin's frustration grew as Claire had scheduled a catch-up call with her old college roommate Shelly for that evening. On Friday, exhausted from a long week's work, they fell asleep at his place cuddling while watching The Devil Wears Prada, too tired to do anything else.

So it was that Austin woke Saturday morning to a raging hard-on and, as he came to his senses, felt and then saw Claire's hair on his abdomen and then her tongue gently flicking around his exposed foreskin.

Austin grunted, at which Claire looked up, brushed her hair from her face, and smiled at him. She ducked back down and engulfed his whole penis in her mouth, then climbed on top of him and rode him until he finished.

Afterwards, Claire laid her head on his chest, facing down and away from him, and toyed with his deflated member between her thumb and forefinger. Austin's thoughts turned to brunch and the shopping excursion they had planned after getting their second ever real paycheck the previous day (the first for each of them having all gone on moving expenses). Claire's thoughts, though, were evidently elsewhere.

She abruptly rose and turned to him. "How long have you known you were small?"

Austin was stunned. "Uh," was all he could manage while he gathered his composure. Truth was he had known since his late teens, when he abandoned hope he would grow any more. Flaccid, in the state Claire was now inspecting, he was closer to five inches than four typically and a respectable girth, so he could "hang with the boys" at the gym and in fraternity shenanigans. He was, alas, definitely not a grower. Sometimes in the bathroom mirror he would joke wryly to himself that his was the WYSIWYG of penises.

This shortcoming had not affected Austin's college or sex life. If sorority girls gossiped, they had the good sense to keep it from him, and he was never short of willing partners. Not once had a girlfriend or partner even hinted at concern or that he had a problem, and he had over time forgotten to be concerned, forgotten that he was, in fact, quite small. But now, a few weeks into dating, this little French minx had just blurted it out like it was obvious and everyone must have known. Had they?

Austin felt the confidence bleed from his face while Claire studied him sweetly.

"Since high school, I guess, but it's not something I think about much. Is it... does it bother you?"

"Oh no," Claire reassured. "It's not like it's the smallest I've ever seen." She gave his penis a peck, then leaned up to kiss him too before jumping in the shower.

Over eggs Benedict, Claire caught Austin up on her week, in particular the Denver trip. The contract was completed, after which Peter had been in a much better mood than they had ever seen him in the office, taking Claire and Anna to sushi to celebrate on expenses, then treating them to a few drinks at the hotel bar.

"Oh!" she exclaimed, remembering something. "Sorry I couldn't see you Thursday, but Shelly, my old roommate, she's from Jersey and in a few weeks is going to be watching her parents' house while they're in Europe; she's planning a party for the 22nd, Saturday. You'll come? She's dying to meet you!"

"Uh, sure!" Austin couldn't imagine why anyone would be dying to meet him, but this was just how girlfriends spoke to each other sometimes.

"Great! If the weather holds up, they have a pool." Excitedly, she added, lowering her tone and elongating the vowels with clear implication, "Also a hot tub!"

Austin's hopes that the earlier topic had been forgotten were in vain, when Claire out of nowhere said "Sorry I called you small earlier. You seemed quite surprised."

Austin looked awkwardly around the busy cafe with tightly packed tables but everyone was engrossed in their own conversations or phones.

"You do know it's not normal to slip out in the missionary position, right?" Austin heard a snicker and his head jerked in that direction, but no-one seemed to be paying attention to them.

Then Claire twisted the knife. "My first boyfriend was quite small too. Not as small as you," she hastily added, "but he took his insecurities and turned them into a fetish. It was quite admirable, really. Small penis humiliation, SPH, have you tried it?"

Austin's eyes darted around the room again then shook his head. He had not.

"Really?!" Claire sounded surprised. "Ugh. He got off on me sleeping with bigger guys, even watching a few times. He gave me space to explore my sexuality and he, he just intellectualized it. He's probably still the smartest person I know." Claire sighed. Austin, concerned, asked how things had ended between them. "We broke up junior year. He's the academic type, he's still in grad school even now. Rutgers, I think. I haven't actually spoken to him in a couple of years. We were just moving at different speeds through life. You don't need to worry about him!" She paused.

"Well," she changed tack. "What about other fetishes?"

Greek life had not offered many opportunities for such exploration, with it all being hook-ups and short relationships and with any deviation from the norm subject to scrutiny. But, Austin allowed, his girlfriend for two years in law school had encouraged him to explore Domination/submission, both of them switching as neither had known much about it, in which time Austin found he preferred the submissive side. "You know, handcuffs and bed ties, that kind of thing."

"Handcuffs?!" Claire exclaimed and Austin thought maybe she was mocking him, but her interest seemed genuine. "Do you still have them?"

"No," Austin lied, not sure whether toys from a previous partner were kosher and making a note to better hide the box of mementos under his bed. "What about you? Do you have any toys?"

"Just a couple of vibrators and some dildos." Austin suspected Claire was lying too but was in no place to judge. She continued, "I always found the mental side of sex more stimulating. I'm sorry, am I making you uncomfortable?"

Austin stammered "Uh, no!"

"Yes I am! And it's ok if you say so. I should say a little more about John, that was my first boyfriend. When we got into me sleeping around, it was great at first, he'd get off on hearing about my escapades, videos I'd send him, etc. But after a while, it just became work for me. I realized I could have all the other stuff without sharing it with him, and it wasn't nearly as much fun for me once I realized he would get off on whatever I did."

She leaned forward and grabbed his hands. "Turns out, it's way more fun for me when I'm pushing a guy's limits. And I'm really enjoying this morning!"

Austin just looked at her, stunned. She laughed and leaned back, releasing her grip. "I'm just fucking with you!"

Austin assessed that, whether she was joking at that moment or not, what Claire said was true. He would have to decide to what extent he was willing to be fucked with, and judged that for now he was willing to go along with it, accepting that Claire would be in control.

"I say," Claire interrupted. "When we're out this afternoon we should go to a sex shop! I've heard of a good one, female staff and not at all seedy. You're so confident and accomplished, I'd love to get to know your submissive side."

Laden with department store bags of professional wear, they arrived at the sex shop, which was indeed quite inviting, all pinks and bright and not just the masses of shelves of X-rated DVDs Austin had pictured, clearly designed to appeal to women. Claire was admiring a couple of comically large dildos when a heavily tattooed and pierced young clerk approached them and asked if they wanted any help. "We're interested in D/s play but not sure what to look for," Claire said. The clerk showed them to the furry handcuffs, whips and related toys and Claire picked up a few to show Austin with raised eyebrows, gauging his response and laughing at some of the more ridiculous options to tell him it was ok to not take this too seriously. "What about for control play outside the bedroom?" she wondered.

The clerk led them to a section of clamps butt plugs, etc, some with remote control activation features. "For the ultimate in controlling your man, though, take a look over here," the clerk gestured.

Austin thought that they hadn't said which side each was taking, but then perhaps it was obvious from their demeanor. He looked to the low shelf the clerk pointed to and cringed. Claire stifled a shriek. Several chastity devices, for both men and women, stared them in the face. "Here," the clerk handed a metal cage to Austin. "What do you think about wearing one of these?"

Austin eyed it skeptically. "Uh, that looks uncomfortable," he said, hoping they would move on.

"Oh you'd be surprised at how much you can squish in there," the clerk reassured, and Claire took the device from Austin to inspect.

"Yeah," Claire mused. "Do you have anything smaller?" Austin blushed.

The clerk gave a cheeky smile and introduced the range, going down to a metal plate that pushed a flaccid penis almost entirely back into the wearer's body. "The size isn't so important, though. The great thing about these toys is you, the woman, get to control your man's orgasms. It's up to you when to release him and have fun together. No cheeky wanking sessions for you," she said to Austin, and Claire gave him a mock shocked look to say you wouldn't?!

The clerk and Claire were clearly vibing and Austin was eager to please. He was indeed intrigued by some of the other ideas and Claire seemed keen, so he picked out a plastic cage that was smaller than the metal one the clerk first showed him but looked more discreet and comfortable. They chose a few other toys for the bedroom and Claire added a vibrating butt plug with remote control.

For the next few days they eased into this play. Austin wore his cage to work for the first time that Wednesday, and grew comfortable as the day went on. Like many of the guys in the office, he started his morning in the gym in the office basement. He was grateful this was not the kind of Big Swinging Dicks environment that his frat house had been. Peter and a couple of the other guys were, as usual, implacably modest, using single stall showers and turning their backs to the room when they pulled on their boxers. Others were more open, but today, for reasons obvious only to himself, Austin took the modest path.

It was, Austin reassured himself, his and Claire's little secret, and she had been the epitome of discretion in the office, chastened by her concerns about their colleagues' reaction to their relationship. She did from time to time during the day tease him by sending raunchy selfies from her collection and links to silly articles with such titles as "20 ways to subdue your man" but he was deep into a project with Anna and she didn't notice his distractions.

That evening, after a late dinner, Claire tied him to her bed and asked him questions about his day. With each unsatisfactory answer she playfully whipped his chest, his thighs, then his balls, further frustrating him until, at last, she released him and gave him two intense orgasms.

Austin, like most avowedly heterosexual men, was skeptical of anal play. Claire warmed him up to it by showing how it was done herself. She selected a butt plug from her collection that was easily twice the size of the one she had picked for Austin, though not one that vibrated. She held it up to his penis for comparison, the girth of the butt plug significantly greater than Austin's. "So, you know, if you can get this inside me comfortably..." Austin, suitably motivated, went to work on Claire with his tongue, then lubed fingers, then gingerly inserted the plug, worried he was hurting her. Claire braced herself and he could hear her taking deep breaths, but she insisted he press on and slowly but surely he got it deeper and deeper. It was tapered at the bottom, so when it was almost all in her sphincter tightened and sucked it the rest of the way. She sat up and smiled. "Now you try?"

The next day, Friday, they went to work together both plugged, Claire professing she enjoyed the fullness of hers. Austin was comfortable but concerned about the app on Claire's phone that controlled his. Testing it in bed had been pleasant, near silent and not overly powerful, but his now-caged cock could not respond as it had at home and he didn't know how much higher the intensity settings went. Twice Claire waved at him, phone in hand, then delivered a mild shock; once she walked past seemingly taking a call then abruptly stopped speaking and delivered a rather less mild shock. But she mostly kept it professional in the office.

After work, the team had drinks in a nearby restaurant. Austin sat at one end of the table with Anna and a young blonde secretary called Sophie; Claire landed next to Peter near the other end. Sophie was blatantly flirting with him and Austin wondered how she could not know about him and Claire, while Anna, who certainly did know, seemed to be egging her on. Twenty minutes in, Austin, listening intently to Sophie, nearly jumped from a much more intense shock. He looked over to Claire, who raised her head from her phone, looked to him and winked. Austin gave her dagger eyes and returned his attention to Sophie.

After a couple more rounds of drinks, Sophie excused herself to use the restroom and Anna was distracted dealing with an email. Austin's gaze wandered, his other adjacent colleagues in the midst of their own conversations. Zap! Austin's head snapped toward Claire with a gasp. That was a big one. Claire, listening intently to Peter, saw Austin out the side of her eye and gave a look of mock confusion, showing her hands and opening them to show no phone. Peter kept talking. A few seconds later, another zzzaaapppp! A long one! Then just a brief pause before it happened again. This time Austin's eyes had been on Claire and he knew she hadn't acted; could it have a timer she hadn't told him about? He looked around uncomfortably but Anna was still busy with something on her phone, so he looked back at Claire pleadingly. And then again, zap! This time Peter turned around and looked towards him and Anna, distracted from what he was saying. Peter turned back to Claire, apologizing, but hadn't got much further when Austin again was zapped and Peter turned his head. Did he have supersonic hearing? Austin worried. Claire laughed at the discomfort she was witnessing. Anna remained focused on her phone.

Shortly after Sophie returned, Austin excused himself and Claire met him outside the restrooms. "I'm sorry!" she said, "it must have a malfunction. I can return it if it happens again. So how about that Sophie?" she teased. "Do you want to fuck her?"

Austin blinked at Claire, unsure how to respond.

"You should go for it if you want! I'll tell you what, I'll unlock you for the evening, but only if you do." How could he refuse? Austin wondered. If it hadn't been for Claire, that's certainly how he pictured the evening going, and if she wasn't concerned then why not? Austin accepted, at which Claire pushed him into the thankfully empty ladies' room and into a stall. She dropped his pants and boxers and pulled out her key, released him and kissed him deeply, while he rose in response to her touch and his freedom. She knelt in front of him and teased him to full erectness, then, when his breathing got heavy, she abruptly stopped and dug her teeth into his right groin.

"Ow! What the fuck!" Austin exclaimed.

Claire pulled up his pants and stood up. "Just marking my territory," she smiled. "Don't want her getting any ideas. Enjoy! Tell me all about it at brunch when you're free. Wait a minute to leave, but don't dawdle, remember you're in the ladies'." She unlocked the door and slipped out. Austin muttered "fuck" to himself then gathered his senses and went back to the party.

Sophie spent an enthusiastic night with Austin and left early the next morning, leaving him in bed to reminisce about the carefree hook-ups of his college days. At brunch, Austin relayed the experience to Claire, who didn't betray a hint of jealousy. "So you liked your freedom, eh? Do you think you could go without it, say until the end of the month?" She was proposing a bet, which she proceeded to detail. "I'd let you out occasionally, mainly for cleaning but maybe also to tease you. You win if you can last until the end of the month, that's one day under three weeks, following my command and with absolutely no relief, if you know what I mean."

Austin was intrigued and asked what they were betting for.

"The winner gets control of half the loser's paycheck for this month. I don't mean they win the money, but rather control over how it is spent. So if you want to go out to eat or shopping, I get to decide how you spend it," assuming she would win, "and you'll depend upon my benevolent control."

Austin accepted, and ten days into the bet he remained confident. This was proving almost too easy, and he wondered again what Claire had up her sleeve. That evening, he got an inkling, when Claire reminded him of the pool party they were invited to that Saturday. He tested a loose pair of swimming shorts and showered in them to see how the cage would look wet, and was reassured it was quite discreet.

On arrival at Shelly's parents' New Jersey home, they were greeted by an African American man dressed only in board shorts. "Michael!" Claire exclaimed and wrapped her arms around his neck, giving him a firm peck on the lips as he lifted her by her waist. Claire introduced Austin after they had separated, then explained they had known each other in their college days in Boston. "I didn't know you and Shelly had got together until the other week. That's awesome! You've kept fit," she teased, putting her hand on his well-defined abs.