Chapter 6: Olivia and Barry

Barry ran upstairs, remembering the last time he’d been there—Olivia had blown him before allowing Barry to fuck her in the ass. Barry had no doubt Gloria and Courtney would fuck as they selected an outfit for Gloria to wear the following night, and he felt no compunction about hoping Olivia would let him fuck her again that night.

Olivia sat on her bed when Barry entered her room. She looked stunning in a red, sleeveless, vee-necked lace dress. Her long, lean body glowed under the bedroom lights, with much skin deliciously exposed and long legs encased in sheer silk stockings shimmering in the light. Strappy red high heels showcased Olivia’s shapely ankles and delicate feet. Olivia’s long, honey-blonde hair cascaded around her toned, shapely shoulders. Her makeup was perfectly on point, with her full lips delightfully outlined and filled in with mahogany red lipstick. Her eyebrows arched over clear hazel eyes, and her eyes’ whiteness and clarity were emphasised by eyeliner and mascara.

Barry stumbled to a stop, overawed by Olivia’s pure, sensual beauty. ‘That’s a man!’ Barry’s befuddled mind reminded him. ‘But fuck! What a beautiful man!’

Olivia stood and performed a slow pirouette. She smiled and said, “I take it that you approve?”

“Fuck me!” Barry exclaimed. “You’re fucking gorgeous!”

“Thank you, Baz,” Olivia said demurely. “Please strip and take a seat at my vanity table. We have quite a lot to do before seven, and it wouldn’t do to make Samuel wait for us. Doing that might become quite painful for myself and Courtney.” Olivia grinned. “Samuel’s looking forward to meeting the new you, Baz. I hope you’ll like her, too.”

Barry had little idea what Olivia meant but guessed he wasn’t required to answer, just obey. Barry dropped his sweats to the floor and sat on the proffered seat. Olivia turned him to face her, and then, humming, she began to transform Barry’s face.

First, Olivia covered Barry’s face with concealer, erasing the few skin imperfections he had. Next, Olivia spread Dermablend foundation over the same area, smoothing out and evening up Barry’s skin colour. Then, Olivia used blush to create cheekbones for Barry. After that, Olivia used more blush to create the illusion of a narrower nose, a less pronounced forehead, and a softer jawline.

Olivia sat back and examined her work. She retouched some areas until she was satisfied with how Barry looked. “I learnt this from the very best there is,” Olivia mused as she began doing Barry’s eyes. “Arpi from Arpi’s House of Transformations on the Gold Coast is a world-renowned film and stage makeup artist. She specialises in creating male-to-female characters for the many productions she’s involved in. I’m not in her class, but I do okay.”

“If your makeup is ‘just okay’,” Barry muttered. “Then I really want to see ‘good’ or ‘perfect’!”

Olivia laughed sultrily before adding a final swipe with the mascara brush. She stepped back and examined her project critically. ‘Pretty damned good,’ she thought. ‘In my earlier life as a male slut, I’d have tried to bang her.’ Then, after taking out the mid-length, page-cut, brunette wig she’d chosen for him and placing it on Barry’s head, Olivia turned Barry to the mirror.

Olivia giggled when Barry did what she’d done after Arpi had done her makeup for the first time. Barry turned to see who stood behind her. Barry turned back to the mirror and blinked, trying to clear his eyes and disbelieving that the beauty before him was him.

“You like?” Olivia asked needlessly. She already knew the answer.

“I,” Barry hesitated. “Fuck me, but I look hot!” He gushed, his meagre cock twitching and rising. “I’d fuck her in a nanosecond.”

“Good, because I believe many will want to. But you’ll need to fuck some, too, because many men fantasise about being banged by a hot tranny. The problem is that currently, I’m the only one attending Samuel’s parties. By the night’s end, I swear I’ve rubbed an inch off my poor cock fucking everyone that wants me to fuck them.”

“Condoms?” Barry asked.

“Forty-eight hours before the party, everyone attending has to get blood tests to prove they’re clean. That means everyone is bareback that night. If the women attending aren’t on the pill or don’t have IUDs fitted, then any pregnancy is on them.”

Olivia bit her inner cheek, wondering again if she wasn’t exposing herself and Courtney to more ridicule and trouble. She hesitatingly confessed. “We have no idea if Adriel, our daughter, is biologically mine. Courtney wanted to be randomly bred by a big-dicked anonymous bull, so she allowed anyone above my seven inches to cum in her unprotected cunt until she was pregnant. Of course, I was fucking her most days after she decided she wanted another child, so Adriel is probably mine, but we don’t know.”

‘Fuck, that’s hot!’ Barry’s confused subconscious exclaimed as his rational mind wondered how John could accept his wife being impregnated by another man so readily. He didn’t know what to say, so he remained silent.

“Fucked up, huh?” Olivia asked. “But I was being blackmailed by our tranny babysitter. Courtney was royally pissed at me for having to put up with me fucking anything that moved for all of our marriage, and I’d discovered that I was innately submissive and couldn’t refuse anything Hannah, Courts, or Samuel asked me to do. Allowing a bull to breed her was how she chose to punish me for my infidelities.

“And you’re okay with it now?” Barry queried.

“Courtney and I are closer than we’ve ever been, Barry,” Olivia smiled. “Having Samuel as our dominant completes us and gives us many opportunities to bring our inner slut out to play. We have but one rule for these weekends that we stay with Samuel and attend his parties: We can fuck anyone we want to, except each other.”

“So, you can fuck Gloria and me but not Courtney? We can fuck your wife, but you cannot?” Barry asked, clarifying.

“And Samuel can fuck all of us,” Olivia grinned. “But we’d better get moving, or we’ll be late for dinner.”

Olivia dragged several items from various dresser drawers and handed them to Barry. He had no idea what to do with them, so he placed them on the bed. Taking the last item out, a pair of skin-coloured stay-up stockings, Olivia picked up the first item she’d handed to Barry.

“This is a Gaff,” Olivia explained before showing Barry how to push his cock into the gaff’s cock pocket and pull it tightly against her perineum, disguising his cock’s bulge. “Unfortunately, wearing a gaff precludes wearing thongs or G-strings because you need at least a bikini brief to hide the gaff.” Olivia handed Barry a soft pink pair. “But it works better than taping your cock and balls away because you can take off the gaff and be ready to fuck someone instantly.”