Pain and Pleasure

Olivia

Olivia arched her back as another vicious stroke of the flogger landed across her already red and burning back, the pain sending a burning jolt of hot pleasure straight to her core, there she felt her pussy clench tight around Rose’s cock. The hot rod of flesh was pounding her hard whilst Olivia could only groan and drool, acting the part of a woman getting her brains fucked out by how good a pounding she was getting.

Internally Olivia was assessing, Rose wasn’t the worst roll in the hay she’d ever had but there was definite improvement needed if Olivia was to be bound to Rose as a member of her harem. The flogger struck again and Olivia let out a deep groan of satisfaction, only exaggerating a bit as she felt Rose’s cock start to twitch inside her.

Looking back at her ‘Mistress’ Olivia could see how sweaty and out of breath Rose was, the young trans woman had obviously never been in this position for so long before, the pain she caused Olivia with each stroke of the flogger or spank on the ass flowing straight back to her. Olivia felt like the entire weight of an ocean of pleasure was pressed up against her pussy.

“Please Mistress Rose! Let me cum! Please tell me I can cum!”

Olivia: +5VP (Fucked by the Mistress), +2VP (Flogged by the Mistress), +2VP (Clamped by the Mistress)

This was the most genuine Olivia has ever been in the last five years she thought, it wasn’t an angle she was playing but just a deep rooted physical need to cum.

Rose

Rose could hear the honest clear desperation in Olivia’s voice, it had been awkward at first but as soon as she got the first spikes of pleasure from whatever Olivia had done to turn punishing Olivia into pleasure for Rose, it had all seemed very clear to her.

Her cock was being squeezed from every direction by the hot wet hole of her former vice principle and Rose was loving every moment of it. She’d never dreamed of doing this, punishing the fucking bitch who’s inaction had made her life a living hell but here she was. Rose reached down and yanked the nipple clamps off Olivia at the same time as she twisted the clamp on Olivia’s clit.

“Cum!”

The burst of pleasure from Olivia’s pain pushed Rose over the edge and she came…hard. Her vision going dark at the edges as aftershocks rocked her body. That same pain pushed Olivia to the edge, her eye wide and spittle spraying from her mouth as she howled. Then Rose’s permission registered and the dark haired woman let out a scream that could have shattered mirrors in a movie as she came incredibly hard, days of awful build up finally released in one giant surge. Olivia collapsed with the power of the orgasm surging through her, Rose falling down next to her, the young trans woman’s softening condom wrapped cock sliding out of Olivia.

Rose was drifting on the edge of sleep, her body drained by the intense sex session that had felt so…liberating. Taking out her frustrations on the canvas of pale and willing flesh that was Olivia. Gentle hands pulled Rose up to lay on the bed next to Olivia and her head was guided to sleep on Olivia’s large soft breasts, Rose started breathing deeper and slower as Olivia recovered, her own breathing calming slightly as a cruel smile spread over her face. Able to see the new score on the tablet that was in its cradle on the bedside table. She had established a firm lead now and a position as the Mistresses whipping girl.