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Hello! If you haven't already, I recommend reading the pretext on parts 1-4 to get an idea of what you're in for before continuing.
As a disclaimer, this story contains ~consensual~, but harsh cuckquean content - humiliation, degradation, emotional abuse, and body shaming. Take this as a potential trigger warning. And if you've been sticking around since part 1 waiting for the cuckquean through-line to come back, it's about to get even messier.
Enjoy!
-TheDaggerAndTheCup
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I led Gemma into the bedroom, where the cat was lying on a pillow. He got up and ran out when he saw us. Ann's four poster bed was high off the ground and had lovely sheets on it. It looked almost regal. Ann and I had shared tender moments in that bed. Orgasms, feelings, dreams. I was excited to make Ann watch as I plowed Gemma in it.
I picked Gemma up and threw her onto the bed. She stretched and arched her back on the duvet, feeling the softness of what used to be Ann's safe place. As she reached, a stuffed teddy bear rolled off the pillows and onto her arm. She picked it up and looked at it.
I laughed. "That's Snugglebear, Gemma. Ann's teddy. She's had him since she was little."
She spit the buttplug she had been carrying in her mouth onto the bed and got up. "Oh my god, you sleep with a teddy bear? Aw, you little sensitive sweetheart. Here-" She tossed it onto the ground in front of her. "You can hump it if you get too worked up." She smirked.
I spit in my hand and rubbed it onto my cock, crawling onto the bed after her. She spread her legs and lifted them, inviting me in. I pressed my head against her asshole and pushed it inside one more time. Gemma's eyes rolled and she moaned. As she opened her mouth I shoved the plug back in. It was still warm from being in her ass. I leaned over her and sucked on her beautiful tits, playing with her barbell piercings with my tongue. I glanced up and noticed Ann kneeling next to the bed, Snugglebear between her legs. Her eyes were welling up again with tears. A slow river of drool was running out of her mouth, dripping down her sloping, baggy tits. I held eye contact with her as I massaged Gemma's breasts, pumping in and out of her ass. Reveling in her body. I sat up and took the plug from her mouth.
"I want to make sure you stay nice and stretched out for me," I said.
"Of course, Daddy," she replied, gazing up at me.
I pulled out and scooted back. She flipped up onto her hands and knees, facing Ann, and arched her back, presenting her holes for me. The hitachi was still taped to her leg, ready for another round. I rested the head of my cock against her waiting pussy, feeling her incredible wetness. I spit into her ass and pressed the tip of the plug into her hole. I could hear her moaning as I stretched her out again, the bulb of the plug being engulfed by her stretching rim.
"Fuck, what a good little slut." I was probing the tip of my cock into her pussy. I remembered suddenly that I wasn't exactly sure she was on birth control. But honestly, it was far too late now to worry about it. She sighed deeply.
"Beg me for it." I commanded.
A pleading string of moaning open vowels gurgled out of Ann. She was leaning forward, her eyes big and demure, despite the fresh tears rolling down one of her cheeks. She seemed to remember herself and stopped.
"Mm, look, Daddy, even our new cucktoy wants you to fuck me." Gemma reached out and grabbed Ann's face again. "He wasn't talking to you, sweetie. Now, if you cut me off while I'm fucking my new man again, I will kick you out of the room. Understand?"
Ann nodded slowly.
"Good." She turned her head to look back at me. "Daddy, please. I need to have my holes filled. I
need
it." She pushed her ass out and wiggled her hips enticingly. "Fuck me and flood my little cunt, please, Daddy, please."
That was all I would ever need to hear. I dragged my head from her clit to her opening, her juices collecting on my cock. I pressed against her and felt myself glide inside her perfect pussy effortlessly. Finally, finally, finally, at long last, I was fucking Gemma's delicious, dripping cunt. The added pressure of the butt plug made her incredibly tight, and I felt her stretch around me as I entered her, but the sheer amount of lubrication relieved any resistance there might have been. We moaned in unison as the head of my cock brushed her cervix and hit the back of her pussy. I was just shy of having my entire cock inside her, and I knew with some more warming up that she would relax to accommodate me.
"Mmm, fuck, Daddy, stretch me out," she moaned.
I grabbed her by the ponytail with one hand and took her by the throat with the other, pushing her down into the mattress and then angling her face up. I saw her and Ann's eyes lock. I felt one of Gemma's hands grab my balls, fondling them softly. I pulled out an inch or so and then thrusted my whole length back into her in a smooth motion. I could feel myself pressing against her P spot. The butt plug was pressing my shaft into the outermost wall of her, making her even tighter than she already was. She moaned loudly. But that wasn't all.
I felt something familiar inside of her. As I slid my cock home, a circular lip of something foreign, almost plastic-like, rubbed across my glans. It was a nuvaring, an intravaginal contraceptive. Ann had always taken the pill, but I had had other partners that had used them.
Oh thank god, what a relief,
I remember thinking,
she is on birth control.