Chapter 23: The Party 4: Olivia

Olivia had a spare moment between transforming Barry into Bianca, greeting guests, and ensuring she was prepared for the party. She slipped away to her and Courtney’s bedroom and sat at their shared double-vanity table. Examining her beautiful features in the vanity’s mirror for any flaws, Olivia sighed before wishing, once again, that she and Courtney had never met Hannah. Hubris, Olivia realised.

Her male persona, John, was a gifted AFL player who the Brisbane Lions paid a lot of money to malinger in their reserves, hoping he’d develop into the team player and star they knew he could be. But John was too arrogant and self-centred to understand that his self-centredness was the very reason he languished in The Lion’s reserves.

John’s teammates recognised his exceptional talents but hated his selfishness and ‘me, me, me’ attitude. They refused to kick the ball to him even if he was free in goal. Being dropped and delisted was inevitable.

John had knocked up Courtney on the night of their School Formal (Prom). She was a virgin, although John wasn’t. Despite his selfishness in sport, John was an honourable man and asked Courtney to marry him. She agreed, and they had two children together in quick succession.

John, being a typical young, virile sports star, and despite being married, fucked every slut he could lay his hands on. The list of his infidelities made Tiger Woods’ look almost amateurish in comparison. John was so sure of his wife’s ignorance and/or acceptance of his affairs that he regularly fucked their babysitters on their couch. His arrogance extended to believing he was above being disciplined or dropped by his club. He was a star, FFS! They wouldn’t dare void his contract.

Hannah’s entrance into his marriage precipitated his fall. Losing Courtney to the hyper-dominant transsexual, being brutally forced-feminised, made to have homosexual sex, forced to watch his wife fuck other men, and facing the loss of his children and home, made John finally admit how much he loved Courtney. Moreover, he was prepared to accept everything she and Hannah did and planned to do as long as he was allowed to remain Courtney’s husband and father to their children.

Everything Hannah and Courtney forced him to endure opened his eyes to his own selfishness and changed him irrevocably. Then, meeting and being seduced by Samuel, an older, calm, dominant man, exposed his innate submissiveness. He became a better person, surrendered his masculinity and sexuality to his wife, accepted her as his Mistress and Samuel as his Dominant, and therefore, salvaged his marriage and, strangely, his football career. His open marriage was strong, and he was now a bonafide AFL star with many clubs prepared to offer him a lot of money to move to them. He honoured The Lion’s years of putting up with him before dropping him and welcoming him back, and he remained loyal to his first club. Plus, he and Courtney ran her parents’ farm, and he found that kept him grounded.

Olivia checked her elegant gold watch, a present from Samuel, sighed, and left for the party. Olivia knew her melancholy would lift as soon as she walked into the dungeon. She was so horny that her cock throbbed in time with her clenching ass. Olivia grinned, not caring who saw. You could be depressed before an orgasm and after one, but you were never depressed during an orgasm! She was looking forward to having many!

Olivia saw her wife’s delicious, barely covered ass entering the dungeon just ahead of him. She skipped across to the door and immediately circled the opposite way to Courtney. Using her feminine persona to get away with it, Olivia greeted guests with ‘cock and cunt handshakes’ and cheek kisses. She’d blatantly grab the guy’s cock when she kissed them and shook it. Or she’d press a finger against the woman’s often bare clitoris and rub it, doing the same. If the woman was wet, Olivia dipped her finger into them.

It only took three greetings before a couple had her on one of the benches. Her tight, sexy ass waved delectably in the air, almost begging to be fucked and spanked. Her mouth was tightly attached to the woman’s cunt, and she stabbed her tongue into it. The man moved behind her, walloped her ass with a paddle, growled at her to lower her tight ass, and prepare to receive. He pulled her plug out and viciously rammed his medium-sized but rampantly erect cock into her ass only a few moments later. Olivia squealed into the woman’s pussy as the man slammed into her, but it was an act. It felt good being taken that roughly.

“Take it, you slut!” The man snarled, pleased his mediocre cock had hurt the young tranny. He whacked Olivia’s ass with the paddle again.

The woman on Olivia’s tongue climaxed first, then she pulled the much younger woman higher, grabbed her throbbing cock, and guided it into her wet, saggy cunt.

“So tight,” Olivia moaned despite feeling little other than a warm oil-like wetness around her 7-inch cock.

“Oh, Gawd, fuck me!” The older woman moaned, also pleased with Olivia’s unnoticed deception.

Olivia closed her eyes and timed her thrusts into the woman beneath her to match those of the man above. She’d pull back as he thrust in to meet her ass, and she’d allow him to power her back into the woman, then she’d repeat. As he slammed her into his wife, Olivia would purr, “OMG, so tight, honey. Gawd, it feels so good. Cum for me, baby.”

“Uuuuuuuuuuuugggggggggghhhhhhhh!” The woman moaned as her climax hit, her body shuddering with bliss.

Olivia knew the pair would want her to cum, so she let her mind imagine it was Samuel who was powering into her tight boy-cunt. She was close, so when the man came in her ass and sprayed her prostate with cum, Olivia orgasmed into the loose, slippery cunt around her cock.

The man pulled out of her ass and fetched a washer. He helped Olivia off his wife and kindly cleaned her cum-filled ass. Courtney pushed her ass back appreciatively as she lowered her mouth back onto the woman’s semen-drenched cunt. Using her tongue and mouth to clean the woman’s vulva gave the woman another small, satisfying climax. They thanked Olivia profusely before holding hands and walking away.

Olivia dropped by the washroom to douche, wash her face, and repair her makeup before rejoining the fray. She walked from the room, and a middle-aged man approached her. Olivia smiled. “Hello, Andy. Where’s your sexy girl?”

“Mistress Gloria is playing with her,” Andy explained.

“Oh, wow!” Olivia exclaimed. “I bet she’ll love that.”

“There’s a wrinkle,” Andy said nervously.

“What’s that?”

“Mistress Gloria has told me that if I don’t return with an ass full of your cum, she’s keeping Sonya as hers.”

Olivia looked at Andy evenly. Neither Andy nor Sonya had ever played with her before, so she wasn’t sure how to respond. She decided to give Andy an out. “You could use your safe words and reclaim her anyway. Besides, I doubt Gloria was serious.”

“I could, but why risk it?” Andy said doubtfully. His eyes dropped to his tented trouser front. “Besides, little Andy seems quite excited by the idea.”

“Yes, he does,” Olivia said, smiling beguiling and reaching out her fake-nails-covered fingers to stroke Andy’s swelling cock. She took Andy’s hand and led him to a low bench. Then, she sat, pulled his pants down, took his entire throbbing <6-inch cock in her mouth and sucked.

“Oh, Gawd!” Andy awedly moaned as Olivia’s talented tongue slashed over his glans and probed into his cock’s eye, drinking the precum drooling from there.

Olivia eased her hand along Andy’s perineum and slid her nailed finger onto his starfish. Andy hummed, “Hmm,” as he spread his legs and allowed Olivia better access.

Taking his hand, Olivia encouraged Andy to sit and then lie on the bench. Then, she slowly worked on opening his back passage so she could take his anal cherry. Andy hummed again as Olivia’s first two fingers slid inside without resistance. Releasing his cock, Olivia tittered, “Someone’s been practising!”