Chapter 12: Brian Becomes a Sissy, Part 4

Janey lived on the other-side of town from Brian and Helena, and the drive took about forty-five minutes at this time of night. On the journey, Brian’s mind wandered back to when his Mistress and he were first together. He sighed because each step seemed so innocent and logical that he didn’t realise what Helena was slowly turning him into. Brian believed he was an alpha male, totally in control of his life and relationships. But his, to quote Frankie Goes To Hollywood, ‘undying, death-defying love for’ the beautiful, slender Master’s graduate led him to a place he did not understand he was travelling to.

However, there was no denying that he loved Helena and was prepared to do whatever was necessary to remain in her presence. ‘The sex is pretty damned amazing and frequent, too.’ He thought, admitting the truth to himself. ‘Most of my married friends complain they’re lucky to get some once a month. I rarely go more than a day without Helena doing something sexual with me that involves me having orgasms.’ As much as he hated to say it, Brian found being a sissy sexually exciting and rewarding. Torture wouldn’t make him admit it, but Brian enjoyed being fucked in the ass. Not so much when a man did it, but when Helena pegged him—ahh, sheer bliss! His sex life was far superior to any of his friends who were not in a Dom/me-sub relationship with their partners. Although he did occasionally envy his dominant male friends who had a submissive wife or partner.

As Brian drove, he recalled the week after Helena had caged his cock and put him into chastity.

Brian watched Helena walk across his front lawn to the cab. Her tight ass, barely covered by her micro-mini-dress, swayed seductively as she walked. His dick lurched in its cage, and Brian looked down, dismayed. He’d learned the first lesson of being in chastity: Trying to have an erection whilst in a cock cage was a terrible idea!

Closing the door, he forlornly pulled his panties aside, took the cage in his hands and attempted to pull it off. That didn’t work, obviously. He considered what tools he had to either cut the cage open or to cut the padlock’s clasp. But the thought of something that sharp that close to his cock and balls convinced Brian that attempting either of those things could end disastrously for him.

Brian contemplated getting help from his friends, but the embarrassment of explaining how and why he’d let some slut he was banging cage him was too much to bear. Finally, he wondered if a previous girlfriend would help him. However, he hadn’t parted on good terms with many of them, and realised they’d probably all come over. Not to help, but to point, laugh and tease. Then there was the risk of letting an ex-girlfriend near his dick with something sharp in her hand. Brian’s butt cheeks clenched as he imagined how badly that could go wrong.

There were two sluts that he was currently wooing—backups in case things with Helena went south. But how would he explain to a prospective fuck that one of his current fucks had placed him in chastity? And that meant again, he’d be letting a woman with vengeance possibly on her mind, near his cock with a sharp item in her hand. That didn’t sound like a wise move!

Resigned to his fate, Brian searched for a high-waisted pair of shorts to wear to golf. High-waisted to ensure his panties didn’t show. He found a pair he thought would work, added a polo shirt, shoes and socks, put his clubs in the car, and drove to meet his usual Saturday playing group. Distracted by the cage and panties, Brian shot the worst score he’d had in the last fifteen years. Not since he was ten and just learning the game had he shot above a hundred, but not even holing a forty-five-footer on the last for double-bogey prevented him from shooting a hundred and two for the round.

Brian accepted the ribbing as being due for that kind of performance and good-naturedly paid for the first four rounds as per their standard bet. The boys stayed at the course drinking and gambling on keno and the horses until it was dinner time. They enjoyed a meal and a few more drinks at the club before Brian decided it wasn’t worth risking his licence and caught the club courtesy bus home. He undressed to shower, and only then noticed his phone held several messages from Helena. He shrugged, deleted them without reading them, and then tossed his phone onto the bed. No bitch was going to control his time with the boys!

Brian showered and rinsed his new panties under the shower. It was awkward to adequately wash his genitals with them in the cage, and his pubic hair kept getting tangled and pulling where the cage split apart. He understood why Helena had suggested he shave his pubic hair off when she released him the following week.

It was Saturday night, and he’d typically cruise into town to look for a casual fuck. Of course, with his dick caged, that wasn’t an option. Brian called several mates, but he was at the age where most of his friends were married or living with a woman full-time. He couldn’t find any takers for a boys’ night on the town, so, frustrated, he opened his computer and searched for porn. Brian found his typical diet of tranny porn, seeing no hypocrisy in being homophobic but being aroused by the tranny fucks guy genre. He cued up a clip where a super-hot, big-titted Brazilian tranny porn star had a guy bent over a table. She held his hands behind his back as she pounded his hairy ass mercilessly.

A few seconds of the clip convinced Brian that trying to become erect whilst in a chastity cage was a truly awful idea! He turned the film off and cast his mind to anything except sex and almost prayed for his dick to stop trying to stiffen. Frustrated, he called a cab and went out anyway. Brian avoided The Victory because, being angry with her, meant he didn’t want to see Helena, and didn’t want to risk losing his temper if he saw her. Especially given that she had the only key to his cage.

Brian entered The Jade Buddha on Eagle Street in Brisbane’s CBD. It used to be his preferred pickup spot when he was a few years younger, but it wasn’t somewhere he went often these days. The Jade Buddha’s clientele tended more to the eighteen-to twenty-one-year-old crowd, who were new to drinking and going out on the town. Even at twenty-five, he found the men’s humour puerile, and the sluttishness of the drunken young women annoying. However, Brian was sure Helena wouldn’t be seen dead in this place, so that’s why he chose it.

Brian was early enough to find a seat at the corner of the bar. He ordered a beer and then turned so he could watch the crowd. Several times, women came up and asked him to dance, but despite their lithe, youthful bodies, Brian refused. He knew they’d gyrate against him, and his body would respond in the usual way. Which, of course, meant his dick would attempt to harden despite being caged away. It didn’t surprise Brian that he was like catnip was to cats to these young women. He was at least a cut above the callow males who infested the bar. Older, smoother, more worldly and definitely richer, Brian carried an aura of confidence few eighteen-to-twenty-one-year-old males could muster.

He stayed about an hour before, bored; Brian finished his beer and walked outside. He examined the queue, shaking his head that so many people would line up to enter such a juvenile venue. Brian returned home, his balls aching and his frustration at being unable to relieve his horniness growing. He tried calling Helena, but the call went straight to voicemail. Brian sent several texts, begging her to either drop a key off or send it via a cab. They were all ignored. Finally, he gave up and went to bed, only for his dreams to be filled with erotic fantasies.

Because he’d gone to bed so early, Brian was up much earlier than typical on Sunday morning. He checked his phone and saw a message from Helena. He opened and read, “It’s been less than a day. Harden up, you pussy!” He tried to call her, but only received another “Harden up” text. Frustrated, Brian hurled the phone across the room. Luckily, it hit the curtains and slid down them to the floor unharmed. He stared at his caged cock, sighed, and went to the bathroom. The panties were still a little damp, but he decided to put them on anyway so he could go out.

Brian phoned his club and asked if there were any spare spots in the afternoon field. There was, so he got dressed and caught a cab there. Playing distracted him from his predicament, and as a result, Brian played much better than he had the previous day. He was still well below his best, but so long as he concentrated on hitting crisp shots, he wasn’t as aware of his caged dick and how horny he was.

Before dating Helena and being caged, Brian would toss off to get to sleep and then do so again when he woke up to get rid of his morning wood. If he were home alone, he’d bring up some porn and have a wank several times a day, too. Plus, being tall, fit, handsome, and hung, he had little trouble picking up. So if porn and masturbation didn’t do it for him, he could easily go out and pick up. Being in chastity precluded all of his usual sexual outlets, and he dreaded having to wait for a week before seeing Helena and hopefully being released from chastity.

By Wednesday afternoon, Brian was sure his balls were literally instead of figuratively blue. He felt like he’d returned to puberty because, having had his usual three or four orgasms a day blocked, he was so horny that even a glimpse of an upper thigh or a panty flash caused his cock to try to erect. Angry, confused, and defeated, Brian left work early. He’d tried calling Helena several times, but every call went to her voicemail. Texts went mostly unanswered, and when they were, read things like “Harden up” or “Three more days. Surely you can go a week without wanking?”

Brian got off the bus at the bottom of his street and walked to his house. He was surprised to see a cab in his driveway and Helena sitting on his front steps waiting for him. Helena remained silent, but when he reached her, she moved her head out of his grasp and unzipped him. Then she slid his panties aside and pulled his caged cock out. She unlocked the device, took it off, and accepted his dick in her mouth. Brian’s cock roared to full erectness in moments, and shortly after that, he exploded in her mouth. She continued sucking until he climaxed a second time. Then, remaining silent, she waited until his dick deflated, locked him back into the chastity device, shook her head to show that she was disappointed in him, and got back in the cab. It backed out and left.

Overwhelmed by the intensity of his twin orgasms, Brian tucked his cock and cage away, zipped up, and sat on the steps before his weakened legs collapsed. His phone chirped, and he awkwardly fetched it from his pocket. The text was from Helena and read, “I expected better from you. Call me tomorrow night and tell me where to meet you. It had better be somewhere nice.”

Brian could not believe how intense his two climaxes were. He looked down at his caged dick regretfully, thinking it would have been nice to remember how good Helena’s mouth felt and toss off. However, he was glad he hadn’t thrown the panties away as he’d wanted to do several times. Instead, he’d washed them every night when he showered and hung them to wear the following day. “That woman will be the death of me,” Brian muttered as he stood and entered his house.

Despite receiving some sexual relief, the night and following day continued to be torture for the young man. His balls felt better that night, but by morning, they seemed fuller than ever. He did his best to ignore them and complete his job. Brian had recently come off probation as a stock market analyst and was earning a solid $125,000 per year plus bonuses because his choices of what to buy and sell were so profitable. Despite being the youngest stockbroker at the firm, there was already talk that he’d be offered a partnership before too long.

Brian would accept, but he didn’t want to work for someone else’s company for too much longer. He and another broker, Harry Mills, had discussed breaking away and starting their own company. They were both sure their current clients would follow them to their new enterprise despite the two brokers’ contracts saying they couldn’t approach their current company’s clients to change if they left. However, there was nothing stopping word of mouth from informing those who Brian and Harry had made rich where to follow them.

Brian didn’t cook for himself, and he didn’t feel like eating out, so he ordered pizza and then used the rower and exercise bike in the spare room to ensure he exercised enough not to put on weight from the extra calories. As he cycled, his mind returned to Helena’s assertion that he was a narcissistic, self-centred asshole. He wanted to dismiss her accusation out of hand because it was patently untrue. However, reflection forced Brian to concede that she might have a point.

He regularly used his charm, looks, and wealth to entice some slut into his bed, where he used her hard with little regard for her wants. It was her problem if she didn’t get off when he did, and he had no problem rolling off her and sleeping, leaving her needs unrequited. If the woman complained, he either told her to shut up or go home. Anyone who complained, he never called again. Brian was unaware that many were grateful for that. Like many men with bigger than average dicks, Brian thought his having one should be enough to excite the woman. Therefore, he did not need to warm her up or do anything to help her achieve an orgasm.

Beautiful women are often the same. They think being beautiful is enough, and they don’t need to put any effort into pleasing their partners. Their lovers should simply be grateful that someone as gorgeous as they would deign to sleep with them. Brian realised Helena would not put up with him being boorish, and although she was by a wide margin the most attractive woman he’d ever been with, he realised she didn’t expect her beauty to be enough for him.

Being a typical boorish man, Brian preferred women with big tits and large bottoms. Helena’s were A-cups and so firm Brian wasn’t sure why she wore a bra. He loved her small, conical nipples, though. Helena was slender to the point of being skinny, although Brian realised she wasn’t ‘cigarette and diet soda skinny’. Instead, Helena’s leanness was natural, and her shapely figure was because of long hours at the gym and running. Helena’s tiny ass was the firmest and shapeliest he’d ever seen or been lucky enough to hold in his hands.

Work was busy the following day, which helped Brian to get through it without being forced to consider his caged cock or how horny he was. When he got home, Brian waited until six o’clock before phoning Daniel’s Steak House and booking dinner for two. Helena’s appetite was another thing he liked about her. Many women would order a salad and then push it around their plates, pretending not to be hungry. Meanwhile, their stomachs growled and protested, begging to be fed. Helena ordered fish or chicken, but ate with gusto, enjoying every bite. Once he’d confirmed the booking, he texted Helena the location, address, and time.