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Fiona did as she was told and immediately returned to laying upon her forearms and knees with her ass raised high up into the air and her tail swishing above her.
Flashing Lydia a grin, he tilted his head for her to join them whilst positioning himself on his knees behind Fiona once again. The other courtesan eagerly crawled over, her mountainous tits swaying beneath her as she moved up beside Fiona.
“See? I know you try to be a good girl for your master, but we know better, don’t we, Lydia?” he asked.
“Oh yeah,” Lydia agreed wholeheartedly. “Deep down, she’s always going to be a naughty, dirty little whore who needs to be punished.”
“Well now, you’re starting to see my problem.” Gregory played along, clicking his tongue against his cheek whilst shaking his head with the struggle before him. “She needs to be punished, but have you felt how tight and wet this pussy is?”
He highlighted the question by reaching out to spread open Fiona’s lower lips with his fingertips until she was fully exposed before all the onlookers. Her inner folds were shiny and pink; fluttering slightly before their eyes.
“There’s no way in hell I’m going to be able to resist a pussy that fuckable long enough to give her the spanking she deserves. So, do you want to help out?”
“Fuck yes!” Lydia cried out; this time without a hint of the play-acting they’d been doing until that point and instead with full-throated conviction.
He jumped slightly at the exclamation, and then let out a little laugh before turning back to once again grasp a handful of Fiona’s long, black hair. After adjusting his grip slightly so that the tension was spread evenly over her head, he shifted behind her and once again filled her saturated pussy up with his cock. Pulling her head back, he began to slowly grind himself in and out of her from behind.
“Ok then, Lydia. I think five spanks will be enough for now. Slave? After each spank I want you to thank Lydia for helping me punish you and politely ask her for the next one. Is that understood?”
“Yes, master!” Fiona said. “Please-”
SMACK!
Lydia’s hand came down fairly hard on Fiona’s rear cheek, making the girl’s pussy tighten around his cock and her body tense up from the stinging pain. She wiggled her ass against him and mewled when the pain mixed in with the pleasure of his cock grinding inside her.
“Sorry!” Lydia apologised. “Got a little too eager there.”
He smiled over at the busty brunette whilst continuing to slowly fuck her friend.
“That’s alright,” he said; rallying his authorative tone. “Slave! What do you say?”
“Th-thank you, Lydia.”
“And?” he urged her further; pulling on her hair slightly to lift her head up and forcing her to arch her back.
“Thank you, Lydia f-for helping my master punish me. Please will you spank me again?”
Another slap rang out through the room as Lydia’s palm connected with Fiona’s other cheek. A loud scream of pleasure and shock escaped Fiona’s lips, and this time she didn’t hesitate.
“Thank you, Lydia for helping my master punish- oh!” She stopped when Gregory sped up his strokes, fucking her at a much faster pace than the slow grind he had been. “Oh yes! Thank you, Lydia for helping my master punish me! P-please will you spank me again?” she yelled over the wet slapping of her ass colliding with Gregory’s pelvis.
He slowed down to allow Lydia to deliver the third spank and then once again he sped up his thrusts to fuck her through her request for another. This continued until all five spanks had been administered. Three on one cheek and two on the other.
“Thank you, Lydia.” Gregory said whilst pounding Fiona’s pussy hard and deep.
“Any time!” With that, Lydia went back to the head of the bed to join the others who were still watching the show with fascination.
“Master!” Fiona cried out. “Please may I cum again?”
“No,” With his other hand he reached out and grasped the base of her tail. “You may-”
“Aargh! Stop! Wait! Skyline! Skyline!” Fiona cried out.
Both Algra and Janette jumped closer to the master and the slave, each sensing that Gregory must have been getting close himself and feeling that he might have passed the point of no return. To his credit, however, he immediately released his hold on Fiona’s tail and her hair before pulling his cock from her pussy and jumping back off the bed. Rushing to the corner of the bed, he rapidly unfastened Fiona’s shackles and the girl’s hands reached behind her to rub the sore spot just above her ass.
“Fiona, are you ok?” he asked. “I’m so sorry. What was it?”
“My tail.” She winced slightly as she stroked the offended area. “I don’t think it’s as sturdy as you seem to believe.”
“Oh! Fuck, I am an idiot. Is it ok if I sit down?” he gestured to the bed beside her.
“Sure it is. And I’m the one who’s sorry. I should have told you it hurt before.” She looked up at him as he took a seat next to her and then immediately leaned in against him when he did.
“Yeah, I’m not exactly briefed on the proper sexual etiquette of tails.” He smiled, and it brought a mirrored expression from her.
“I don’t expect you to be. It’s fun when you grab it when you’re going slowly. It does hurt, but just a little, and I’m kind of into that. When you’re fucking me like just now? It’s way too painful.”
“Are you alright?” He looked over her shoulder down toward her tail but the fur blocked out any signs of reddened or bruised skin on her.
“I’m fine! I was having so much fucking fun too. I love the way you pull my hair, and getting spanked whilst you fucked me is now my idea of a happy afterlife. I should have told you about the tail before, but I thought I could handle it.” She frowned, obviously pissed at herself for the misjudgement.
“You could keep going!” Janette encouraged them.
“Haven’t I ruined the moment a little?” Fiona asked with a sad smile.
“Fiona, don’t be crazy,” he said. “You haven’t ruined anything. A safe word is used for a reason. It’s more than ok to use it when things stop being fun for you, and if I ever found out I’d actually hurt you like that and you didn’t use it then this never happens again. Alright?”
She nodded her acceptance, and her smile became more genuine on hearing his words.Content is property © NôvelDrama.Org.
“Good. Now, do you want to continue? This isn’t going to be a one-off if you don’t want it to be, and if your tail is sore-”
“I want to continue. Master.” She nodded fiercely.
He fought the urge to grin at her, and instead stood up again whilst Lydia, Algra and Janette all happily piled back up to the top of the bed to watch the show.
“Stand up, hands behind your back, wrists together.” He took on his authorative, sharp tone with her once again.
Fiona happily followed the demand, standing just as she’d done before with her feet shoulder length apart and her chin up whilst putting her hands behind her.