Taking Turns

After a dinner that included frequent use of the vibrator’s remote-control, Jacob led Anna back to the bedroom. He had her lay spread-eagle face-down and used the restraints he had set up that morning to fasten her to the bed. Once she was secured, he grabbed a large buttplug from his bag and the bottle of lube from the nightstand. He repeated the same process he had earlier to insert the large buttplug into Anna, eating her ass and using his fingers to tease and stretch her opening.

Once the buttplug was in, he turned his attention to her pussy. The vibrator she had was designed to allow simultaneous insertion of fingers or a penis, so he used two of his fingers to finger her while he slowly ramped up the vibrations. Anna cried out in ecstasy, but Jacob backed off whenever she began to approach orgasm to keep her on the edge. He eventually withdrew both his fingers entirely and got up to retrieve the dildo. He inserted it into Anna’s pussy alongside the vibrator, then moved to sit down in front of her face. He lifted her head up and ordered her to give him a blowjob. Once his cock was in her mouth, Jacob looked down at Anna.

“Does my slut like having all three of her holes filled?” he asked, to which Anna nodded as much as she could under the circumstances. “I bet you love being filled. You look so good all airtight,” Jacob continued.

Anna continued to nod approval, and her moans were causing her mouth to vibrate slightly around Jacob’s cock, adding to the feeling of the blowjob. She did love having her holes filled. She loved the submissiveness of it, loved the feeling it gave her, and loved being so on display for Jacob.

After a few minutes, Jacob moved back down between Anna’s legs. He removed the buttplug and the dildo. He placed the buttplug off to the side, then applied additional lube to Anna’s asshole. It had been stretched after a few hours of being filled with the various buttplugs. Jacob pressed the tip of the dildo against Anna’s asshole, and the residual juices of her pussy combined with the additional lube on her asshole allowed it to slide in easily.

Jacob then positioned the tip of his cock against Anna’s pussy before sliding in all the way alongside the vibrator. The fullness combined with the vibrations caused Anna to begin to rapidly approach an orgasm. Jacob began to slowly fuck her as it built, and when he felt it begin he picked up the pace and force of his thrusts, timing them with Anna’s orgasm. As Anna’s orgasm subsided, Jacob removed her restraints. He then laid on his back and ordered Anna to straddle him. He guided his cock to her anus, and she lowered herself onto him. Jacob was incredibly horny at this point and knew that the day was building to an incredible finale.

Anna took a second to adjust to Jacob’s cock, although having been stretched already she did so quickly. Once she was adjusted, she began to ride Jacob. Jacob reached up to Anna’s neck and began to lightly choke her. He knew she liked rough sex, so he removed his hand from her neck and gave her a light slap across the face with his fingers. He did this a few more times before moving his hands to her waist. He gave her a few spanks with each hand, but as he felt his orgasm building he grabbed tightly to her hips.

“Make me cum Anna,” he moaned. “Make me cum into that perfect, sexy, tight ass of yours.”

“Cum in me Master,” Anna moaned back. “Use that nice big cock of yours to spray your cum into your little slut’s ass.”

Jacob was as horny as he had ever been, and his cock was on the verge of exploding. The view he had was unlike anything he had ever seen. He could see his cock stretching Anna’s asshole as it slid in and out. He could see Anna’s pussy dripping juices from the vibrator’s constant work. He could see her tits bouncing up and down as she rode him for all she was worth, and the whole time she was staring directly into his eyes.

“Cum for me master, please cum in my ass,” she moaned as she stared at him.

That was enough for Jacob, and he began to cum. As he did so, Anna orgasmed as well, succumbing once again to the vibrator that hadn’t stopped since before her last orgasm. The feeling of Anna’s orgasm made his even better, and he shot his cum deep into her ass as he had the best orgasm of his life.

They collapsed and laid there catching their breath for a few minutes before Jacob turned to Anna.

“Bedtime. I hope you enjoyed being mine for the day,” he said.

“I loved it, and I can’t wait to take my turn with you tomorrow,” she said with a smile.

They cleaned each other off once more in the shower. As they lay in bed after, Anna spoke to Jacob.

“Tomorrow, I’ll wake up before you do. I’ll set up everything while you sleep, and I’ll wake you up once I’m done. As soon as you’re up, you’re mine,” she said.

“I can’t wait,” replied Jacob.

The next morning, Anna woke as the sun rose. Careful not to wake Jacob, she climbed out of bed. She grabbed the bag full of toys that he had used the prior day and then silently walked downstairs and retrieved the bag of items she had purchased for her turn in charge. She dumped the contents of both bags onto a table and began to prepare. In one bag, she placed an enema kit, a pair of men’s lingerie that had a hole in both the front and back, a chastity cage, a small buttplug, a cock ring, a blindfold, a ball gag, a clitoral vibrator, a collar, and a leash. She placed the rest of the toys in the other bag and returned it to its hiding place in the living room. She walked back into the bedroom with the first bag. She placed the enema kit and underwear in the bathroom before placing the bag into a nightstand drawer before undressing herself. She looked over at Jacob, who was sleeping soundly lying on his back. She checked that the restraints were still under the bed and began attaching them to Jacob while he slept. She had gotten his right wrist and was finishing strapping his right ankle before he woke up. She saw his eyes open and looked up at him once she finished with the strap.

“Spread eagle, middle of the bed, so I can finish tying you up,” she commanded.

Jacob complied, and Anna finished strapping him down. She then climbed onto the bed, straddled his face, and lowered herself down.

“You’re going to start my day by making me cum, so get going,” she said.

Jacob began eagerly eating out Anna, who grinded back into his tongue. Turning around, she could see he was quickly forming an erection, which pleased her. She continued to grind into him, and after five minutes was close to orgasming.

“Fuck yes Jacob, oh my god,” she screamed as she came all over his face. Once she stopped spasming, she moved off of his face, which was coated in her juices.

He looked up at her, clearly expecting her to start doing something to him. Instead, she undid his straps.

“Enema and shower. Shave everything down there too while you’re at it. Once you’re done, put on the underwear that is in the bag. I’ll be on the bed waiting,” she said.

A short time later Jacob emerged from the bathroom. His partially erect cock and his balls hung through the front of the underwear. Anna ordered him to turn around and admired his ass and the easy access she would have to it. She then ordered him to kneel in front of her.

“The rules for today are similar to yesterday. ‘Stop’ means stop, and ‘Wait’ means to hold on. You may only refer to me as mistress unless I say otherwise. You must obey every order I give you. If you disobey, I will punish you.” Anna pulled out the chastity cage to demonstrate her point before continuing, “If you are good, I will reward you for it. You may not speak to me unless I speak to you first. You will wear that underwear at all times unless told otherwise. You may not touch my tits, ass, or crotch without permission, and may not touch your cock, balls, or ass unless I instruct you to. Is that clear?”

“Yes, Mistress,” Jacob responded.

“Good,” said Anna before pulling out the collar and placing it around Jacob’s neck. She attached the leash, then spoke, “Now, I believe it is your turn to make me breakfast.”

After breakfast, Anna led Jacob into the living room. She instructed him to kneel in front of the couch. She retrieved a set of handcuffs and secured Jacob’s hands behind his back. She then sat down in front of him, spread her legs, and began using her fingers to masturbate with Jacob just inches away. She looked Jacob in the eyes and began to moan, expressing her pleasure knowing the inability to participate would drive Jacob wild. After a few minutes, she removed her hand and held out her fingers to Jacob.

“Clean them off,” she commanded.

Jacob leaned forward, sucking the fluid off of each of Anna’s fingers one at a time.

“Good boy,” she said. “I got myself pretty close to cumming. If you can finish me off using your mouth within one minute, I’ll let you cum in my pussy. If not, I’m going to give you a demonstration of the chastity cage.”

Jacob leaned forward and began eating Anna out, mustering all the effort he could in an attempt to get Anna to cum. It was a valiant effort, but Anna had lied about being close. She wanted an excuse to get Jacob into the cage so she could tease him and get even for the prior morning’s edging he had subjected her to. After a minute was up, Jacob sat back defeated.

“Shame. Time to get that cage on,” she said, grabbing his leash and leading him up to the bedroom. She ordered him to remove his underwear before strapping him back down to the bed. She removed the chastity cage and waited for his erection to subside. The cage was about four inches long, which was enough for him to fit in comfortably while soft but would not allow him remotely enough room to achieve an erection. Once Jacob was soft, she placed it on him. She then laid on the bed next to him, got her vibrator out, and got to work. She brought herself to a loud orgasm before looking back towards Jacob, whose cock was straining desperately against the cage.

“Looks like somebody is horny. Would you like me to play with your cock?” Anna asked.