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.

"Yes, Mistress, please," begged Jacob.

Anna lowered her vibrator and pressed it to the underside of Jacob's caged cock. She smirked as she saw him tense up, struggling against the restraints and confines of the cage. She held the vibrator there for 15 seconds before pulling it away.

"I'm going to untie you. Once I do, flip over and get spread eagle again," she said as she moved towards the restraints.

Jacob complied and was soon tied back up, although this time he was laying on his stomach. Anna retrieved a bottle of lube and the smallest buttplug that she had bought. She covered her finger and began using it to explore Jacob's asshole. She knew he enjoyed when she played with her ass, but she was enjoying the fact that no matter how much he enjoyed it he wouldn't be able to get hard. She took her time, teasing him and driving him wild until eventually she slipped the lubed-up buttplug into him. She then reached between his legs and grabbed his caged cock before turning on her vibrator and placing it against the tip of his penis. Jacob again began to struggle, but Anna did not hear a safe word and held the vibrator where it was for another 30 seconds before stopping.

Anna decided Jacob had had enough of the cage for now and removed it. She then untied him and ordered him to flip over. Now on his back, Jacob's erection was clear. Anna moved down between Jacob's legs and wrapped a hand around his cock. She began using her thumb to rub just under the head, which she knew drove him wild.

"Do you want to cum, Baby?" she asked Jacob.

"Yes, Mistress," Jacob responded.

Anna straddled Jacob and slipped his cock into her pussy. She began slowly rocking back and forth, although too slowly for Jacob to cum from.

"Do you like having the plug in your ass?" asked Anna.

"Yes, Mistress."

"Is your body mine?"

"Yes, Mistress."

"What if I wanted to put something bigger in your ass?" asked Anna.

"Anything you want, Mistress."

"Good boy."

Anna lifted herself off of Jacob's cock and instructed him to flip over. She went and grabbed a medium sized plug, then went between Jacob's legs and removed the small plug. Unlike the small plug, the medium one she had grabbed was curved and designed to stimulate Jacob's prostate. Anytime he moved, the plug would move inside of him and stimulate him. At least, that was how it worked in theory, but Anna wanted to see for herself. She lubed it up using the bottle that was still at the base of the bed, then slowly worked it into Jacob. Job done, she ordered him to flip back over. She climbed back onto his cock and began to fuck him slowly once again. She reached down and grabbed his throat, then used it to move his head so she was looking him in the eyes.

"I'm going to make you cum now," she said. "You have my permission to be as loud as you'd like."

She began fucking him, riding him quickly. Jacob began moaning almost immediately, voicing his pleasure. She removed her hand from his throat and used it to slap him.

"Cum for me Jacob," moaned Anna.

"Fuck, Anna," Jacob yelled, and Anna felt him begin to cum in her.

She continued to fuck him hard during his orgasm, and when he was finished she lifted herself off of him. She then turned around, backed up, and sat her cum-dripping pussy on his face.

"Clean me out, Slut," she commanded.

Jacob had never, to her knowledge, had his own cum anywhere near his mouth, and they had certainly never done this before. Anna wanted him to feel completely submissive though, and few things she could think of would accomplish the task as quickly as having Jacob eat his cum out of her pussy. Jacob obeyed, and Anna soon felt his tongue reaching inside of her. Once she felt that he had done a thorough job, she sent him to shower and clean himself. She told him to keep the buttplug in, and that when he was finished he was to come kneel naked before her.

Jacob emerged from the bathroom, still slightly damp, and kneeled in front of Anna. He looked up at her expectedly.

"Turn around and get on all fours," she commanded.

Jacob obliged and Anna took a moment to admire the view. His cock hung between his legs, and she had a nice view of the plug that was stressing his asshole. She leaned forward and gave Jacob a slap on the ass.

"Time for lunch," she said. "Put on the underwear I gave you, a t shirt, and a pair of shorts and meet me down there."

A few minutes later, Jacob met her downstairs and they enjoyed a light lunch. After eating, Anna ordered Jacob to strip down to his underwear and stand with his hands behind his back. Once he was doing so, she stood up and grabbed his penis. She toyed with it until Jacob was erect again, then grabbed it and began leading him back to the bedroom.

"I hope you enjoyed your break, because I still have plenty of plans for you," she said.

Once upstairs, Anna instructed Jacob to sit near the top of the bed. Once he was seated, she handed him the largest buttplug she had bought along with a bottle of lube, which he placed next to him. She then grabbed the ball gag and placed it in his mouth. Finally, she grabbed a cock ring and her vibrator and sat between Jacob's legs, facing him.

"Masturbate for me. Bring yourself close to orgasm, then stop," she instructed.

Jacob reached down and began stroking himself. The ball gag muffled his moans, but Anna could tell he was enjoying himself. She turned on her vibrator and placed it against her clit. She enjoyed watching Jacob play with himself, and the visual combined with the stimulation to her clit quickly got her horny. The sight of Anna masturbating clearly turned Jacob on as well, since it was not long before he stopped stroking himself. The precum glistening on the tip of his cock revealed he had been nearing orgasm. Anna set her vibrator down, then used her hands to place the cock ring around Jacob's cock and balls. She then blindfolded him before returning her vibrator to her clit.

"Remove the buttplug and insert the one I gave you. You are not allowed to touch your penis during this," instructed Anna, stifling moans as she did so.

Jacob got the buttplug out relatively quickly. He started reaching around for the larger one, but Anna spoke up.

"Before you do that, use your fingers to stretch yourself for a minute," she said.

Jacob lubed up his fingers, although the blindfold meant it was a bit of a messy process. Anna enjoyed watching him struggle. He eventually got his fingers lubed up, then began to finger his own asshole. He started with a single finger, but soon added a second.

"Fuck yourself a bit," Anna commanded.

Anna wasn't particularly into stuff involving Jacob's ass, but she did enjoy the submissive nature of what Jacob was doing. She knew that if he was willing to do this for her, she he would do anything else that she desired the rest of the day.

The vibrator continued to work its magic, and soon Anna cried out as orgasm washed over her. Once it subsided, she ordered Jacob to start working on getting the large plug inside of him. Knowing that her body needed a break if it was to last the rest of the day, she turned off her vibrator and watched the rest of Jacob's show in silence. When he finally had the buttplug inserted, she reached forward and removed his gag and blindfold before taking the cock ring off him. She then turned around and got on all fours with her ass pointing towards him.

"Eat my ass," she said.

Jacob quickly got into position and began hungrily exploring her ass with his tongue. He started by moving his tongue around the outside of her anus and gradually began to probe closer the center. He could tell by the subtle movements of her body that she was enjoying it, and she soon began pushing back against his face. He took this as an invitation to dive in and he began plunging his tongue in and out of her asshole, causing her to moan with pleasure. After a few minutes, Anna pulled away from Jacob and flipped over onto her back.

"Vibrator, now," she commanded.

Jacob complied and handed her the vibrator. She quickly turned it on and placed it against her clit, and within a minute she was bringing herself to orgasm while Jacob watched from between her legs. She cried out in pleasure as she came. Once her orgasm subsided, she set the vibrator down and ordered Jacob to stand beside the bed, facing her. She sat up and put her legs over the side of the bed in front of Jacob. She reached out and began stroking him slowly before looking up and speaking.

"Did you enjoy watching me cum?" she asked.

"Yes, Mistress," Jacob responded.

"Do you like having the big plug in?"

"Yes, Mistress."

Anna removed her hand from Jacob's cock, using one of her fingers to wipe away the drop of precum that had emerged from the tip. She looked him in the eye as she slowly licked the precum off of her finger. She got off of the bed and walked behind Jacob.

"Bend over, hands on the bed," she ordered.

Jacob complied, and Anna reached out and applied a bit of pressure to the end of the buttplug that Jacob had in, which caused him to lightly moan. She then spanked Jacob twice, once on each side of his ass. She saw her handprints start to form and smiled.

"Time to clean up," she said.

Jacob looked over, clearly disappointed he wasn't about to cum, which Anna noticed.

"Do you have a problem with that?" she asked.

"No, Mistress."

"Good, that's what I thought."

Anna led them into the bathroom and started the shower. She scrubbed Jacob off before having him do the same to her. Anna teased him when she could, careful to keep him far from orgasming but also horny enough to keep him on edge. After drying off, she ordered him to stand still with his eyes closed. She retrieved the items she needed, then got to work putting them on Jacob. She started with the blindfold to make sure he couldn't see what she was doing, then got to work on the rest. Jacob's cock had finally softened, so she placed the cage back over it. She then put the leash and collar around his neck. She checked to make sure his buttplug was still firmly in place, then she grabbed the leash and led him downstairs. She glanced at his cock as she walked and smiled. As planned, the plug in his ass was rubbing against his prostate as he moved, which turned him on and caused his cock to strain against the cage.