Chapter 29: Present Day 15

Sunday morning dawned, and Brian’s eyes opened. He could hardly believe his eyes, but he remained in Helena’s bed and she was still in his arms. Sometime after they’d fallen asleep, Helena had rolled onto her back. Brian had stayed on his side with his head resting on her shoulder, under her chin. He still cupped Helena’s small, taut, conically shaped breast as his thumb strummed her nipple unknowingly. Helena’s breast felt bullet-tipped in his hand.

Easing out of bed, Brian went to his room and put on a bra and panties and a long, loose dress with leg slits almost to his panties. He walked to the main bathroom, washed his face and brushed his teeth and hair. Then, remembering they had another sissy visiting, Brian went back to his room and put a wig on and his breast forms in. After completing those tasks, he walked to the kitchen to start breakfast. He mixed eggs for omelettes, grated cheese, and sliced tomatoes and spinach. He put those aside for when his two Mistresses arrived, then he halved English muffins and readied them for toasting.

Helena strode in first, and Brian immediately wished he’d put his chastity device on because his dick lurched and erected. Helena quirked an amused eyebrow at his tented front, but said nothing. Brian gaped at her as she passed him. Helena wore black leather trousers that appeared as if she’d been poured into them. On her feet were black 7-inch heeled ankle boots with silver buckles. Above her leather pants, Helena wore a dark-purple leather bustier that clung to her sublime body like a second skin and displayed her small, tight breasts deliciously. It also left her midriff and lower back bare. Her diamond-centred sunburst belly button ring sat between her bustier and pants, and emphasised her muscular stomach.

Helena’s long, naturally greying black hair hung from a high ponytail down to her magnificent ass, and emphasised that divine asset superbly. Her makeup was done more dramatically than usual. With her eyebrows and eyes outlined more heavily than she typically did them, her foundation and blush much darker, and her full, pouty lips heavily outlined with dark-red lipstick, Helena looked ready to grace the cover of BDSM International magazine. If she were to be on the cover page, she’d pick up a multi-tailed leather flogger and hold it seductively just before the photographer took the shot.

Brian waited until Helena sat at the breakfast bench and then brought her coffee. “Would you like your breakfast now, or would you prefer to wait for Mistress Haley?”

“I just received a text from Mistress Margaret saying she was on her way here with Kennedy and Mistress Angie. Please make extra to feed those two. Don’t forget to prepare breakfast for yourself, Kennedy, and Mark. You may sit at the sissy table as we eat.”

“Of course, Mistress. Is it okay if I do bacon and eggs for us sissies?”

“You may.”

“Thank you, Mistress. Tap your cup when it needs filling, and excuse me while I prepare extra for Mistresses Margaret and Angie.”

“I believe Mistress Angie has dressed her trainee sissy in something quite spectacular. Perhaps rather than being embarrassed by being less dressed than sissy Kennedy is and new-sissy Mark will be, you’d like to dress in something racier and do your makeup? You have almost an hour before Mistress Margaret gets here.”

“Thank you for your consideration, Mistress,” Brian said thoughtfully as he selected his outfit in his mind. He gathered what he’d already assembled and put it in the fridge and then returned to his bedroom. He sat at his vanity, which mirrored Helena’s setup, and started his makeover. Brian had done it so many times that it took very little time to do an over-the-top sissy face. Then, opening his closet and considering his options, Brian thought, ‘Mistress is wearing an all-leather outfit, so I should contrast that by dressing in silk and lacey frills.’

Nodding at his outfit choice, he took off his dress, bra and breast forms. Then he stepped into his gaff and tucked his sissy-cock away. A white thong, suspenders and stockings followed. He took out his silicon chest plate with the 16DD breasts and worked that down his arms and over his head, settling it into place. A white stretch sleeveless T-shirt served to hide the plate but not restrain the plate’s full, bouncing fake breasts. Next, he put on a frilly fetish milkmaid’s outfit, complete with a brown pinafore front. The skirt part of the dress was lacy frills that bulged widely and left the bottoms of his ass cheeks, the suspenders and his stocking tops exposed. 7-inch heeled ballet shoes completed Brian’s look.