Chapter 16: Brian Becomes a Sissy, Part 6

“I can’t believe how hot Brian looked in his dress!” Shelley said, gushing as she drove them back from Brian’s place to Helena’s sister’s place.

Shelley, Helena, and her sister were in the middle of a lesbian fuck-fest when Brian sent the photo. It was only because Helena hadn’t shut Outlook down on her computer that she’d heard the message ‘ping’. Computers and messaging were still new and exciting in those days, so she extricated herself from her lovers’ embrace, and checked her email.

“Oh, wow!” She’d exclaimed. “Have a look at this, guys!”

The other two got off the bed reluctantly.

Janey looked at the photo, shrugged and said, “Some poofter in a dress. Whoop-de-shit!”

However, Shelley and Helena exchanged meaningful glances, their pussies frothing over the image. Helena snatched her phone and texted her sissy project that they were on the way over.

“I can’t believe how quickly he’s becoming a sissy,” Helena said drily. “You made a good start in introducing him to CBT. I thought he’d object for sure. But he seemed to enjoy it.”

“What’s the plan for Friday?” Shelley asked.

“We bring food to cook to Brian’s place, sissify him, fuck him, torture his balls, fuck him in the ass with our strap-ons and then go home. If he calls on Saturday, I’ve found my husband. If he doesn’t, I dump him and move on.”

“I like your plan,” Shelley said, sniggering.

Friday evening saw the three girls, Helena, Janey, and Shelley, in Shelley’s car, on their way to Brian’s place. They stopped at a Chinese takeaway near his house and bought plenty of food for that night and probably tomorrow. After discussing her plans with her sister, Helena changed them. Instead of feminising Brian and staying in, the girls planned to dress him all girlie and make him accompany them to The Wickham in The Valley. Janey thought the chance to fuck three women simultaneously was enough to ensure Brian’s compliance.

Janey, who had dated several cross-dressers, had dropped by Shoes of Hollywood, a store that specialised in larger shoe sizes and clothing for cross-dressers. She’d bought a long, wavy reddish-brown wig and a pair of heels she thought would fit. She’d also bought several quite revealing dresses to put Brian in. All three girls’ pussies were foaming at the thought of feminising Helena’s boyfriend and humiliating him by dragging him out into public. All three had brought their strap-ons; Brian’s ass was in for a torrid time that night.

Brian opened his door. He wore just the bra, panties, and slip Helena had given him. The girls grabbed his hands and dragged him back inside and to his kitchen, where Shelley grabbed his ass and kissed him passionately. She handed him to Helena, who did the same, and then she introduced her sister. “Brian, this is my actual sister, Janey. Janey, my man Brian.”

Brian examined Janey. This time there was no doubt this was Helena’s sister. They looked too similar to be anything else. Brian thought they could wear each other’s clothing, even though their hair colouring was different. Helena had raven-black locks that fell in straight lines to her waist. Janey’s was shorter, only to her shoulders, and a wavy, reddish-brown. Janey was perhaps a kilo or two heavier than her sister, with breasts a tad smaller and hips slightly wider.

Brian felt an almost irresistible need to kneel, but he controlled that instinct and took her hand in his instead. He kissed the back of her hand and said, “Pleased to meet you, Janey. You look as ravishing as your sister.”

Janey turned to her sister. “Oh, he’s a charmer.” She turned back. “Flattery will get you exactly what you were going to get anyway. Stop ogling and get plates and forks out.”

Brian blushed, not realising that he and Janey had similar thoughts simultaneously. His was, ‘I’ll definitely take a swing at that if things go south with Helena.’ Hers was, ‘If Helena dumps him, I’m calling him.’

Trying to act cool, Brian got plates and forks out. Helena opened the containers, and they mixed and matched the various meals until everyone had generous helpings of each dish. They sat at Brian’s kitchen table. Brian looked at the three beauties surrounding him and couldn’t believe his luck. He stood long enough to open the bottle of wine he’d bought for the occasion and got himself a beer. Returning to the table, he grimaced when Helena took the beer off him and put it back in the fridge.

In a portent of what was to come, she grinned at him avariciously and said, “Wine for the girls.” She handed him the glass she’d gotten when she put his beer away.

Brian thought of arguing, but Brian’s mum raised no fools, so he shut up and accepted the glass.

After they’d eaten, Helena took the lead. She grabbed Brian by his cock cage and dragged him off the chair and to the bathroom. She unlocked his cage and threw it into the basin. After telling him to strip and setting the water temperature, she pushed him under the water and undressed herself. Brian’s eyes bulged when he saw that Janey and Shelley were both already naked. There wasn’t enough room in the cubicle for the four of them, but with the curtain pulled back, all four girls could get their hands on him.

Janey handed the girls a disposable razor each and then filled their hands with shaving foam. Brian’s tall, leanly muscled body was covered with the foam only seconds later. Working efficiently, the girls shaved Brian’s entire body, removing all hair except for his head and eyebrows. Helena and Janey did Brian’s groin and anus simultaneously. Helena kept her hand on his dick constantly, regularly taking it in her mouth and bringing him close to climaxing. Hands flew over his body as the girls rinsed the foam off him. Next, they washed his entire body with rose-scented soap, and then they stepped out and dried him off.

The girls didn’t need to shower, but the steam from the shower had ruined their makeup and hairstyles, so they sent Brian to his bedroom to wait until they’d repaired themselves. Fifteen minutes passed before Brian’s eyes widened as three stunningly beautiful women entered his room. And his dick raised its big purple head. Helena held a hairdryer, which she used to dry Brian’s hair.

“Sit on the bed’s edge,” Helena demanded.

Wondering why, Brian did as he was told. Helena stood before him, taking items from her toiletry bag. Brian wondered what she was doing, because her makeup looked perfect to him. He snatched his head back when she poured foundation liquid onto a sponge and tried to apply to his face.

“Hold still!” She growled.

“What? No way! What the fuck are you doing?”

“You’re coming on a girl’s night out. You’re not a girl, so we have to make you into one.”

“What? No fucking way! I’m not some cross-dressing poofter!”

Janey sniggered. “We’ve seen photos that belie that statement.”

“What’s your fucking problem?” Helena snarled. “You have three women who want to take you out, and when you return home, we’ll all fuck you. Why are you being an asshole again?”

“That wasn’t our deal,” Brian said weakly. “It was only that I wear a bra and panties for a week and then you’d bring Janey and your sister over and we’d all fuck.”

“So?” Helena replied. “I want you to experience being out on the town as a woman. Perhaps you’ll understand why some women are so cynical about men. And again, doing these things to you turns me on.”

“Me too,” Shelley said.

“Me three,” Janey added.

“There you go. Let me doll you up, and three hot, horny women will take you out and be all over you like a fat man on a pie before we take you home and fuck you even more senseless than you currently are. But if you don’t want to, fine. Janey, Shelley and I will go out and pick up. Trust me, none of us will have problems picking up a stray root or two. Or maybe we’ll find one lucky guy and fuck him senseless instead.” She mused silently for a bit and then added as if curious. “Did you know that most cross-dressers are heterosexual? I bet we’ll find one at The Wickham who will be more than happy to entertain three hot chicks simultaneously.”

It occurred to Brian that further objection would nullify his earlier thought that his mother hadn’t raised a fool. Shit! He knew guys who’d said, “I’d give my left nut to have a threesome,” and they were only partly joking. He’d had two threesomes and had the chance for a foursome, and he was blowing it! If letting them dress him up as a woman was the price he had to pay, then pay it he would!

“Let’s do it!” He said, gathering his courage while thinking, ‘I hope like fuck no cunt from work or any of my friends or family sees me out dressed like a tart.’

The girls swarmed around him, dollying him up. Janey put fake nails on his fingers while Helena did his makeup. Shelley brought the wig out and held it while she brushed it, then she assembled the outfit they’d chosen for him, including the breast forms they’d bought when they got the heels and dresses. Brian wanted to object when Janey started painting his toenails, but he bit his lip. After all, he always wore shoes when he was outside the house, so what did it matter?

It took about thirty minutes before Helena stepped back, satisfied with how Brian looked. The others gathered, and Janey suggested slightly darker lipstick. Shelley agreed, so Helena retrieved another stick from her bag and applied it.