Chapter 18: Brian Becomes a Sissy, Part 7

Brian remembered the night he went out on the town dressed in drag for the first time. He’d gone out so many times dressed en femme since then that they all blurred together. However, that first time was burned so indelibly into his mind that he’d never forget it. He’d awoken alone the following morning and seen Helena’s message. After reading it and considering his life’s direction, Brian texted Helena saying he was there for the long haul. Little did he know where that haul would take him.

Weeks passed with Brian wearing women’s lingerie beneath his men’s clothes every day and him not realising he’d become Helena’s submissive sissy. The next significant event was months in the making. Brian and Helena’s sex lives were extreme, with Helena regularly bringing her sister, Shelley, or both to his place to play. Having regular sex with his girlfriend and up to three other women (when Anna joined them) meant Brian eagerly continued down the sissy path without realising the ultimate destination.

Helena had encouraged Brian to dress in drag again and go out to The Wickham with her. Thinking he’d experience something similar to the last time when they’d gone there with Janey and Shelley, Brian eagerly agreed. However, this time Helena insisted Brian dance with various men. Those men’s hands wandered onto places Brian did not want them to. Simultaneously, Helena danced with men whose hands were all too free as far as he was concerned. Helena’s twin-tented top showed how much she enjoyed their attention.

Jealous and angry, Brian insisted they return to his place. Jealous because Helena had reacted sexually to other men’s touches, and angry because his cock responded to the touches on his ass and taped-away dick. When they reached his home, Brian stormed out of the cab and inside. He stripped off his clothing, went to the bathroom, and removed his makeup.

Helena paid the driver and followed him inside. She found Brian in the shower and ripped the curtain aside. “What the fuck is up your arse?” She asked.

“Not some faggot’s dick, that’s for sure!” Brian snarled. “Listen, Helena. I’m not a fucking poofter, so stop making me dress like one and trying to make me suck a cock or take one up my arse!”

“Whassa matter, Brianna?” Helena sneeringly replied. “Did all those men touching your boy clitty make you horny, so you’re blaming me because they made your dick hard?”

Brian turned and threw a left cross that caught Helena completely by surprise. He’d pulled it at the last minute, horrified he’d thrown it. But it still spun her head around and made her see stars. Helena immediately dropped to her knees and gobbled Brian’s cock down. She gave him a stupendous blowjob before saying, “This girl is sorry she insulted you, Master. Would you like me to pour you a scotch on the rocks?”

Gaping at her, Brian realised what she’d said, and he exalted. “That would be good, wench. Bring it to me in the bedroom. I will fuck you in the ass and then sleep.”

“As you wish, Master,” Helena said submissively.

Brian watched her go, wondering why he hadn’t smacked her months before, like his father had said he should. He thought, ‘If I’d known she was all bluff and bravado, I’d have put her over my knee and spanked her sublime ass when she first started this feminisation shit!’