Chapter 20: Brian Becomes a Sissy, Part 8

Brian explained the events that led to Helena tying him up, leaving out that she’d threatened to cut off his balls. He didn’t want to terrify the young man too much. Shaving Mark’s legs as he described the events, Brian told Mark how he became what he is—a cock-sucking nancy boy who loved being fucked in the ass.

It took Brian about an hour to work his way out of the ropes tying him to the bed. By then, the rope had rubbed Brian’s wrists and ankles raw. Grateful he was finally free, Brian sat, leaning against the bed, panting. His horror at almost having his dick and balls cut off with a blunt knife and spoon remained fresh in his mind. Helena had him convinced she would do it.

The guilt about punching her intensified when he remembered her sorrowful demeanour, and her hurtful parting words. He wanted to be her man. He’d known that for months now. Now she was gone, Brian realised he was also willing to do whatever necessary to be her man, including sucking cocks and/or taking them up his clacker. Doing that seemed such a minor price to pay to be with someone he adored and who was as sexually free and adventurous as Helena was.

If he was honest, which Brian prided himself on being, he was living every red-blooded male’s dream. He got to have regular sex with multiple women, all of whom his partner had introduced to him. And all he had to do to receive that gift was wear women’s underwear and occasionally go out, dressed in drag, with her and her female friends. Brian finally understood that if he did what Helena asked, it turned her on, and the sex was fanfuckingtastic! And given she and her friends regularly fucked him with their strap-ons, letting a man fuck him wouldn’t be so bad, would it? Also, if his simply dancing and flirting with a man turned her on so much, and he reaped the benefits of that arousal, couldn’t he do that for her?

Brian began crying as he recalled Helena’s last words. He’d blown it. Blown it big time. Picking up his phone, he stared at it through teary eyes. Without hope, he called Helena’s number. It went straight to voicemail. “If this is Brian. Go fuck yourself.”

When the phone beeped, Brian pleaded, “Please, Helena. I fucked up. Talk to me, I beg of you.”

He waited forty-five minutes before trying again. This time the message said, “If this is Brian. What would be the point?”

He left, “I want to make it up to you. I love you, Helena. I will do whatever you want to make this right.”

He tried her phone several more times before giving up at around 1:00 a.m. and sleeping. Brian woke up with the morning sun in his eyes. He’d forgotten to shut the blinds before falling asleep. He checked the phone. Nothing. He called her number. “If this is Brian. Too little, too late.”

That message didn’t change for a week, no matter how many texts he sent her or how many messages he left. On Friday, Brian was called into Chris Savage’s office. His performance had been poor at best, barely breaking even for his week of trades.

“What’s gone wrong, Brian?” Chris asked. “You’ve gone from top broker to also-ran in a week. Is this just this week, or is this what we can expect from you in the future?”

Stockbroking was not for the faint-hearted. Careers could easily be lost in a week of disastrous trading. Brian’s week wasn’t career-ending, but more than another week with poor trades could be career-threatening.

“I’ve had a few personal problems at home, Sir,” Brian said.

“Ensure you leave them there, son,” Chris replied. “You know better than to bring your problems to work. Another week like this one, and you’ll be looking for another job.”

“I understand, Sir. I’ll fix it, I promise.”

“Ensure you do. Dismissed, and I’ll expect to see a return to the performances that had us considering offering you a partnership.”

“Yes, Sir.” Brian stood and left.

“Think he’ll make it?” Andrew, another senior partner, asked.

“If he can’t separate his home life from his work, he’s doomed anyway,” Chris replied dismissively.

Brian went to The Victory on Friday night, hoping to see Helena. She wasn’t there. He waited for two hours, ignoring the various trollops who approached him before he caught a cab to The Valley and entered The Wickham. She wasn’t there, either. Brian waited there until nearly 1:00 a.m., hoping Helena would turn up. He feared that if she did, she’d be with another man. In despair, Brian caught another cab to The Sportsman Hotel in Spring Hill. He didn’t find Helena, but found the nightly drag show instead. Brian watched the drag queens prancing around the stage, looking like overblown caricatures of women, and found them fascinating. He tried to talk to two of them and was surprised by their reticence.

Sitting at the bar was another interesting experience. Several guys approached him, and two tried to pick him up. Brian’s experience being out, dressed in drag, meant their approaches didn’t bother him, but he wasn’t interested. However, one of the queens, Trixie Trinity, climbed onto a bar stool beside him. Using her normal man’s voice, Trixie said, “You wanted to chat with a drag queen? Well, here I am.”

“I’m Brian. Pleased to meet you, Ms Trinity.” She’d been introduced to the crowd during the show. “May I buy you a drink?”

“Trixie’s fine, dahlink,” Trixie said with an extremely exaggerated faux-lisp. “I’ll have a glass of house white, thanks.”

Brian looked at her, amused. His grin nearly split his face. “You’re so funny! You kind of take a woman’s typical mannerisms and then exaggerate them to the extreme. It’s hilarious!”

“Why, thank you, dahlink. A girl does try.” She chuckled and dropped the lisp. “What can I do for you, chap?”

Brian blinked. He was unsure if he preferred the lisp, but the rough-sounding voice coming from an exaggeratedly female face just seemed weird. To hide his confusion, Brian signalled the bartender and ordered Trixie’s wine and another beer for himself. He turned back to Trixie and handed her the glass before saying, “My girlfriend wanted me to dress in drag and go out with her. I did it a couple of times, but then she wanted me to dance and flirt with blokes. I got a little pissy about it, and we broke up. I’m trying to understand the attraction. That’s all.”

“Let me see if I understand. You’re a handsome man, so I assume your girlfriend’s pretty hot?” Brian nodded. “And she gets turned on when you dress as a woman and take her out?” He nodded again. “She gets even hotter when you dance and flirt with guys, and probably just about rapes you if you let them feel you up?”

“Well, yeah. What’s with that?”

“Do you have any sexual peccadillos that, if others knew about them, they’d think were weird?” Brian blushed and embarrassedly admitted he enjoyed watching tranny porn. Trixie nodded before saying. “So if you had a girlfriend who was into watching lesbian porn, would you think she was weird?”

Brian replied, “She’s bisexual, so it wouldn’t be weird at all.”

“Lawd oh lawd,” Trixie muttered, shaking her head that someone could be such an idiot. “Does she bring women home to share with you?”

“Every time I dress as a woman, and go out with her.”

“So, your girlfriend is bisexual, has threesomes and probably moresomes, with you, and all she wants in return is for you to dress in drag and dance and flirt with men?” Brian nodded. “Honey, if I were straight and my girlfriend brought girls home for me to share, I’d suck a dick for her in a flash. Seriously, dude? What’s up with you? You have every red-blooded man’s dream, and you won’t suck a dick to keep it? That’s fucked up, man. Did you realise that most cross-dressers are straight?”

Brian nodded. He remembered Helena saying that.

“Do you understand how many men your girlfriend could have lined up, willing to do whatever she wanted if she’d let them dress as a woman and date her?” Trixie shook her head, bewildered someone could be so stupid. Some guy, who loved to dress en femme and suck a cock, would snap Brian’s girlfriend up in a moment, and he’d never object or dither if she wanted him to blow someone.

“But I’m not gay,” Brian said weakly.

“You don’t have to be. You just need to want to make your girl happy. A girl who brings girls home to make you happy.”

“But I thought she did that for herself. Not me.”

“If she was bringing girls home for herself, she doesn’t need you there. She’d pick a random up whenever her itch for a dick got too much for her.”

“You think she’s bringing those girls home for me?”

“Does she pick up girls while you’re out, or does she bring them with her? Who does she bring if she does?”

“Usually, she brings her sister and best friend over.”

“What?” Trixie gasped. “Your girlfriend brings her sister and her best friend over, and you all have sex together? Your girlfriend and her sister get it on together, too?” Brian nodded. “Jaysus, Brian! I don’t know any guy on the planet who wouldn’t suck a cock for that opportunity! Fuck! Most would take it up the ass to get it! Look, going back to my comment about weird peccadilloes—your girlfriend’s fetish, if you like, is watching a straight guy dress as a woman and play with guys. It’s what revs her motors. What’s the big deal with that?”

“Nothing, I guess.” He thought furiously before admitting, “I’ve been an idiot.”