Jon gasped at the pain of initial entry. Elizabeth did not move for several seconds, giving him time to adjust to the welcome intruder. She wanted their first time to be perfect pleasure for him, or as near to perfect as she could make it. He exhaled slowly, and closed his eyes, waiting. "I'm going to move a little farther into you now, Jon. Tell me if it is too much." she said, exerting a gradually increasing pressure which moved the device an inch farther into him. His breathing remained deep and even, but she felt a shiver pass over his immobilized body.
Elizabeth was motionless, watching his face for signs of both pleasure and pain. There was no question of her power over him at this moment. She felt both the excitement of his surrender to her, and a deeply satisfying sense of responsibility for his well-being. His eyes opened and met hers, and she felt the desire flash between them. Still holding his gaze, she very gradually pushed another inch into his warm and inviting ass. She felt her erect clitoris throbbing against the base of the strap-on, and pushed again, closing her eyes. His body quivered slightly beneath her, and he gave a low groan of painful pleasure. She did not stop this time, but continued the slow and steady progress until her pussy lips could feel his balls beneath them. The entry was complete.
She held the position, without moving. "You are mine now," she said in a fierce whisper, just prior to beginning a slow retreat.
"Yes, Mistress" he replied, grimacing in both discomfort and intense arousal as she moved again, this time pushing the pink rubber extension of her body all the way back to its previous location. "Oh yes, Mistress", he sighed, as the pleasure began to conquer the pain.
She paused again, and said "I am going to fuck you until I decide to take a break, and then Margarite will take over. Unless you use your safe word, you cannot stop us. Do you understand?" She was getting into a slow, but steady, rhythm in her movements. The tension she had felt in his body earlier was dissipating, as he relaxed and welcomed her motion.
"Yes, Mistress, I understand" he replied, his voice just above a whisper.
They both heard the click of heels on the steps outside, and froze, just a moment before the door opened.
"Only me", Margarite called, cheerfully, as she entered the room and closed and locked the door behind her. She was wearing a pair of black silk pajamas, with a red robe. "Ah, very nice, Elizabeth. That is exactly what this SlutSir needs; to be ass-fucked by his submissive.", she continued, laughing as she spoke. "By the way, how is he?" she asked her friend, walking from the door toward the futon.
Elizabeth had resumed her steady tempo of retreats and advances, and her attention was once again given to the man she had impaled. Jon appeared to be lost in the sensations and his own lack of power to stop them. Elizabeth knew the feeling of that type of headspace quite intimately, and it thrilled her to see it behind his eyes. He was loving it all, she was sure.
Margarite stood next to the futon, near the end where Jon's bonds were attached. "Yes, I see you are enjoying this, SlutSir", she continued, letting the robe slide off her shoulders and fall to the floor. "makes me wonder what else you will enjoy before we tire of fucking you…" she trailed off, with a mischievous smile.
"Whatever you desire, Ma'am", he replied.
"I have what I desire right now", Elizabeth interjected. "I am fucking your beautiful, tight ass, and you are loving it. Aren't you, SlutSir?" She had been moving away from him as she spoke, and at the end of her question, she thrust into him deliberately, making him catch his breath before he could answer.
"Yes, I am, Mistress", he said. "I am loving you taking my ass."
Margarite assumed a more serious demeanor, and sat down on the corner of the futon, near Jon's shoulder. "You are going to need to take a more active role, Jon, While I fuck you, you will be thanking Mistress Elizabeth by eating her wet pussy. You won't be allowed to stop until one of us gives you permission. Are you ready to show your gratitude, SlutSir?", the Domme asked.
"Oh, yes", he whispered in reply, a smile playing at the corners of his lips.
Elizabeth began an agonizingly slow retreat from his depths. Even with the knowledge of more to come, it was still difficult to force herself to disengage from their new intimacy. "You don't want me to go, do you?" she rhetorically asked, feeling his body shiver In pleasure beneath her.
"No, Mistress", he answered, as the rubber dildo slipped easily out of his ass.
Elizabeth climbed off the bed while Margarite removed her Hefneresque pajamas to reveal a purple leather harness and a realistic version of a penis. It was both longer and wider than the one Elizabeth was now in the process of removing. The harness had been fastened loosely, so the substantial appendage which protruded from it would hang close to her thigh and not spoil the drape of her outfit. With the clothes gone, she no longer wanted it in an at-ease position, and was making adjustments to bring it to the appropriate angle for use. Jon was watching her, speechless with both anticipation and anxiety.
When Margarite was satisfied with the adjustments, she tightened the harness and ran her hand up and down the 8 inches of Caucasian skin-tone silicon, reveling in the feeling of her new cock. "You should feel this, Jon, before it enters that eager and open hole. Here, put your fingers around it" she said, as she knelt on the corner of the bed, positioning the dildo so he could grasp it with his still restrained hand. Obediently, his fingers closed around the two inch wide tool, and his breathing quickened, imagining it invading his recently stretched ass. "It is a bit larger, but you should be ready for it now", she continued, removing his hand and then positioning herself so that the cock's head was barely touching his asshole, poised, and ready to sheath itself in his tight, warm anus.
Elizabeth was free of the strap-on now. She removed the cock from the harness opening, put the harness atop the dresser, and laid the pink phallus on Jon's broad chest. It was felt warm on his skin, and was still shiny from lubricant when he glanced down at it. The memory of how it felt inside him only minutes earlier sent a bolt of desire through his entire body. Elizabeth looked to her friend, saying "I think we should start with his ass, and then I will climb on his face when I am ready. Besides, I want to watch him take this one", she said, smiling.
"You are such a voyeur", Margarite chuckled, and began her descent into their willing victim's body. Her pressure was steady and slow, without the initial pauses Elizabeth had given him. The broader head of this cock made him utter a small cry of pain, closely followed by a sigh of pleasure as it went through the tight ring of sphincter muscle, gaining complete access. "See, sometimes bigger is better", she continued, pulling back slightly, then moving forward again, evoking a moan from the helpless man beneath her.