Chapter 14: Brian Becomes a Sissy, Part 5

After Helena left, Brian took the stockings off before dressing for golf. He tried several polo shirts before he found one loose enough to hide that he was wearing a bra. Fortunately, he’d grown accustomed to wearing panties, and the brassiere didn’t distract him to the same extent the panties had the previous week. Therefore, his form returned, and he scored well. shooting several shots under his handicap. Not only did he clean up his bets with his playing partners, he won the daily event, too. He celebrated with his mates, eating dinner at the club and drinking until the club closed for the night. He caught the last courtesy bus home and slept like a log.

Brian woke on Sunday morning. The first thing he noticed was that he wasn’t as horny as he’d been the previous week. He put it down to how much sex he’d had on Friday night and Saturday morning. Brian got up and peed before putting on the panties he’d washed during his shower the previous night. He’d gotten used to the pair Helena had bought him, which were a cotton blend. However, Shelley’s silky pair added a higher level of sensation, and they caused his poor caged dick to throb despite being soft.

Brian wandered around his kitchen, making coffee and toast wearing only Shelley’s panties. He marvelled at how good they felt on his groin and then remembered how much he liked how his legs felt in the stockings. Brian picked them up from where he’d dumped them when he got ready for golf and examined them. He scrunched them up as Helena had shown him, and awkwardly rolled them up his legs. It took a bit of fiddling with his back to the mirror before he got the seam straight, and when he had, he took a photo and emailed it to Helena. He received a smiley face in return.

After eating, Brian put on the bra and slip and examined himself in the mirror. A weird emotion came over him, and he searched for something to put in the bra to simulate breasts. He discovered that a pair of his socks kind of worked. He Googled creating false breasts and discovered two options. Brian didn’t have any rice or foot stockings, but he had condoms. He filled two with cold water and put them inside his bra. Shivering, he took them out and broke them open before throwing them away. He got two more and filled those with warm water.

Brian looked in the mirror, and his cock lurched. From the neck down, he looked like a tall, slender woman with generous C-cup breasts. The bulge of his cage ruined the silhouette, and he experimented with trying to hide it. The only thing that worked was to push his caged cock and balls back behind his thighs. So despite the pain, he did that. Brian checked his reflection again and muttered, “I understand what Helena gets out of this. My body looks pretty damn sexy. If I met a woman with a figure like this, I’d probably try to pick her up even if she was a butterface (nice body, but her face!).”

Brian liked how he looked so much that he stayed at home and wore it all day. It was only when he needed to go to bed to be rested for work that he took the condoms out of the bra and split them so the water emptied. He looked in the packet and made a mental note to buy more before coming home tomorrow. He got in the shower and decided he’d shave his armpits and around his cock cage. His legs and arms felt alright, so he ignored them. He was thankful his job required long sleeves and trousers, which hid that he’d removed his body hair.

Despite still being horny, Brian slept much better that night, and he woke up feeling refreshed. His dick throbbed, trying to erect into its typical morning glory piss-fat. He sighed and went to the bathroom to relieve his bladder. Brian learned that standing and peeing through his cage often meant the stream hit the cage and splattered everywhere. So, glad there were no witnesses, he sat and peed. “Sitting like a bitch,” he muttered unhappily. His thoughts perked up when he realised that what he was doing ensured he’d have a three-girl foursome in just five days. “Who gives a fuck if I have to piss like a bitch if I get to fuck three sluts simultaneously?” He said, still muttering.

Because inner-city parking was prohibitively expensive, Brian caught a bus into town where his firm was. He walked up his street to his stop and got on his usual bus. His eyes surreptitiously wandered over the girls as they typically did. But there was a difference. Now, he compared them to Helena and even, to a lesser extent, Shelley. In his mind, none of the girls could hold a candle to the woman who had crashed so forcefully into his life, and there was perhaps only one he’d swap Shelley for. That woman resembled Helena. She was tall, angular, and severe looking with long black hair and pert, high-standing breasts similar to Helena’s.

‘Fuck, I’ve got it bad!’ Brian mused as his dick throbbed. Friday night had been the highlight of his sex life so far, and he knew the upcoming Friday would be even better.

Brian walked from the Queen Street bus stop to his office tower, intensely aware of his stocking-covered legs. The effect wasn’t as pronounced because his trousers interfered with the delicious whisk-whisk of the nylons rubbing together. However, he still found the feeling extremely erotic, and his balls ached with unrequited arousal. Luckily for Brian, when he took his position behind his computer screen and began his daily trades, his professionalism took over, and he completed his tasks perfectly. By the day’s end, his trades had earned a near-record amount and were the best of the firm’s by far.

The four senior partners recognised the excellence of his day’s work, and towards the day’s end, they invited him into the boardroom. A glass of Glen Livet whiskey greeted him as he sat at the table. Chris Savage, the firm’s founder, tipped his glass in Brian’s direction and took a sip and said, “You’ve had a spectacular last few weeks, Brian. Returns forty percent above what is expected and twenty-three percent above the next best, which happens to be me.”

“I had no idea, Sir,” Brian replied modestly. He was honestly surprised.

“Something’s changed, Brian,” Chris continued. “You seem more focused and less distracted by pussy. Is there a new woman in your life?”

“I have been seeing someone regularly,” Brian admitted. “It’s too early to know if she’s the one, though.”

“Okay. I won’t pry any further. But another month of these results, and we’ll offer you a partnership.”

“Thank you, Sir,” Brian said respectfully. “I’m pleased my efforts have been noticed.”

“Keep up the good work,” Chris said dismissively.

Brian knew that was his cue to leave, so he replaced the whiskey untouched, stood and left.

Chris watched him go and turned to Mike Alberts, his supervisor. “Go over today’s trades and ensure they’re legitimate. Also, see if you can understand what he saw to make these trades and tell me if he truly is gifted, or if this is just some lucky streak.”