Amanda, Jen and Ryan Pt. 07

[This story contains elements of power exchange, including blackmail, corporal punishment, chastity, female domination, and other sexual fetishes. If you are offended by this type of content, please do not read.]

Part 7 - There's Good, and then There's Total Bliss

Ryan walked uncomfortably up to Jen's front door. He was holding two bags of groceries. Jen had not asked him to bring dinner, but he thought it would be a nice gesture - perhaps build some good will with Jen.

Amanda opened the door. She was wearing only thin cotton panties and had two nipples clamps hanging down from her pert little tits, both with weights on them. She reached out and took one of the bags from Ryan and then Ryan stepped inside. He heard the TV on in the family room. Amanda locked the front door the led the way to the kitchen. Ryan put the cold items he had purchased into the refrigerator, and then left the other items on the counter. He walked into the family room and Jen was lounging on the couch. Amy lifted her feet and sat down with Jen's feet resting in her lap. She gently massaged them as Jen looked up at Ryan.

"Well?" Jen said smirking.

"Well what?"

Jen leaned forward and picked up a remote, and Ryan's eyes grew wide when he realized it was not for the TV.

ZAP!

Ryan dropped to the floor and grabbed his caged cock. "Jesus!" He exclaimed.

"That was level 5." Jen said.

"What was that for?"

"Your snarky attitude. Are you here to have fun, to explore, to SERVE, or did you just want to get punished over and over?" Jen held her finger over the remote.

"No! Please! I'm here to have fun and serve. I'll be good. I promise. But please Jen, I need to come. You have no..."

ZAP!

"So sad. That was level 6. You address me properly. And it's only been a little bit of denial, can you not control yourself?" She looked at Amanda. "Maybe we should keep him in chastity until Thanksgiving. Give him something to be thankful for," Jen said smiling, a sadistic evil glint in her eye.

"NO! Please Goddess Jen!" Ryan quickly knelt up at Amanda's feet and then leaned over and kissed both of Jen's feet that were in Amanda's lap.

"Now that's a good boy," Jen said. "Lay down on the floor and worship Amanda's feet while we watch the rest of our show."

Ryan settled in front of the couch and used his hands to guide Amanda's feet onto his chest. He started to massage them with his fingers and Amanda shifted one foot toward his mouth, and he reflexively opened his mouth and began to kiss and suck on her toes. Toes that were perfectly manicured and painted a luscious purple. Ryan's head began to swirl as his cock strained against the cage.

Ryan's mind was sinking into sub-space. Here he was, a strong and capable 18 year old, caged and laying the floor sucking on the toes of his girlfriend at the command of her what... her mistress I guess. But he could not help himself, he absolutely loved it.

Amanda's foot worship came to an end along with the show they were watching. Jen put her feet on the ground at the other end of the couch and snapped her fingers pointed at them, and Ryan crawled over to them and began the same service he had given Amanda. Jen told Amanda to run and get her hairbrush and a leather paddle from the basement. She returned quickly holding the two items out for her inspection.

"Good girl," Jen said. "Now, over my knee."

"Why?" Amanda asked, realizing too late her mistake.

"Because I said so. And for questioning me, I think I am going to make this a very thorough punishment. Push you a little. Let's see is Ryan here can handle your screams and begging."

Jen turned to Ryan.

"Keep worshipping my feet and you may also worship my legs. If you stop at any time, or you ask for mercy for Amanda here, you will get the same when I am done with her."

Ryan looked up at Amanda who was visibly shaken. He continued to suck on Jen's

toes and lick her soles, but his eyes were on Amanda's face. The hand spanking only lasted for a few minutes before Jen picked up the hairbrush. Jen did not pull any punches.

"CRACK!"

"CRACK!"

"CRACK!"

Three gunshot like smacks to Amanda's sit spot, and she cried out. Jen delivered three more, and then three more and by the time she reached twelve, Amanda had tears falling down her cheeks. Ryan shifted uneasily as he began to move his tongue up Jen's leg, offering a caring smile to the crying Amanda.

Jen's arousal was palpable as she continued the spanking. She loved to hear her subs beg and cry. She knew she was a sadist. She had known since a young age, but only recently had she been able to really experience the pleasure it brought her. She was soaking her panties and likely the couch as she finally put down the brush and picked up the leather paddle.

Jen smirked at Ryan. He was straining to continue the worship of her legs, and it was more of a distraction now than pleasurable. She looked at Amanda writhing over her lap and then leaned down and asked her a question.

"What do you want my little kitten?"

"To please you mistress." Her answer was sincere and Jen smiled.

"Does that mean you want to suffer for me? Take my paddle on your sore and red ass until I am satisfied?"

"Yes, if that pleases you mistress."

"And if I decide you don't get to come, is that ok?"

"Whatever pleases you mistress."

"Good little kitten."

Jen raised the leather paddle and began a much harder volley of spanks. Amanda cried out and Ryan lost his control.

"Please Jen!"

"I knew it!" Jen said triumphantly. "You think so little of her that she can't take a little pain? I told you once already - she likes it. But you don't see it. "

Jen nudged Amanda and instructed her to get up. She patted the couch next to her. "Come sit here Ryan."

Ryan got up and sat on the couch. Jen handed him the leather paddle. "Let me show you." Jen gestured for Amanda to lay across Ryan's lap and Amanda looked at her and then meekly obeyed.

"Come on, spread your legs a little," Jen ordered.

Amanda blushed and turned and looked back at them. Jen took Ryan's hand and placed it between Amanda's legs, just shy of actually touching her sex.

"Feel that heat? She's so aroused right now I could make her come with a feather. Now give her a dozen reasonably hard swats with that paddle."

Ryan looked at Amanda and she nodded. Ryan raised the paddle and brought it down with little to no force and Amanda laughed. Jen took his hand in hers and she swatted the paddle down with a good amount of force and the sound it made was a satisfying SNAP. Amanda winced and shifted, her core heating even more. Jen guided Ryan through for more good slaps and then released his hand.

"Now give her 5 more good ones." Jen instructed.

Ryan felt more confident now and rained down five more good slaps. Amanda moaned at the last two, and Jen pointed at her cotton panties which were now soaked with her arousal.

"You really like this don't you? Being spanked like a bad little girl. How come you never asked me to spank you?" Ryan asked.

Amanda did not answer, so Ryan brought the leather paddle down. Six more times, and then bunched up her panties into her ass crack so the last four swats he delivered landed on her bare ass.

"I asked you a question."

"I don't know sir, I was embarrassed, but I love it." Amanda said turning bright red with shame.

"See?" Jen said smugly. "I know what I'm doing. And you just volunteered for a spanking of your own by begging me to stop. And to think, you not only brought on your own punishment, but you deprived Amanda of a well deserved orgasm while I was spanking her. "

Amanda whined at that remark. "Please, can you just do it a little more?"

"No, Ryan has ruined it for you. Perhaps later we can see to your needs. But now, Ryan, you and Amanda switch places. Time to warm up your little bottom. To his credit Ryan was still wearing the plug from last night.

"What a good little bitch you are Ryan. Keeping that plug in all night." Jen pulled the plug from his ass and her finger explored the gape that was left behind. "This will be fun to play with," Jen said, smiling at Amanda.

Jen started with a hand spanking to warm Ryan up, and then progressed to the hairbrush until his ass was red and he was squirming and beginning to tear up. Jen reached over and picked up a bath brush and handed it to Amanda. "Now, " Jen said, "30 with the brush and we can move on to more pleasant activities."

Amanda knew it didn't take much from the brush to cause real distress, so she was holding back a lot and Jen chastised her. "Unless you want the same 25, from me, I suggest you pick up the intensity."

Ryan cried out as the brush slammed into his sensitive sit spot. Jen laughed and said, "Good girl. Just like that."

Ryan began to cry and kick his legs, but Jen held him in place as Amanda gave him every last one. He was sobbing by the end and Jen told Amanda to caress his blistered bottom for a few minutes.

Jen kissed Ryan on the cheek. "Good boy," was all she said.

After Ryan had some cream rubbed in and composed himself, he cooked dinner, and cleaned up the dishes. They watched a movie and then Jen led them back down to the basement.

Jen led Ryan over to a table in the corner. There was a rolling cart against the wall that was covered, and Ryan looked at Jen and then at Amanda.

"I'm trusting you guys." It was a statement that sounded more like a plea.

Jen had a mischievous look in her eyes, but leaned in to whisper quietly in Ryan's ear.

"You've got a safeword if you need it."

They secured Josh to the table in the most humiliating way possible. His arms were secured to the table at his sides, his chest had a leather strap around it holding him to the table surface. And his legs were bent at the knees, spread wide, and tied to posts at the top of the table. His legs were pulled back so far that he was staring at his own caged cock. He was entirely exposed and helpless. He looked at Amanda and said one word.

"Please."

Jen laughed as they rolled the cart over from the wall. Ryan closed his eyes before looking over as Jen removed the cover revealing the edging machine from earlier.

"No! You promised that today I would get the real orgasm!"

Jen leaned down and looked at him sternly. "You'll get what I give you. And don't question my integrity or I'll put your cock and balls through hell, and you'll be in so much pain you'll beg NOT to come."

Ryan shut his mouth as they once again attached the leads and plugs and then removed his cage and put the apparatus over his cock. Jen turned it on and adjusted some of the dials.

"Now we are going to play a game Ryan. I am going to ask you questions, and you will answer honestly and quickly. If you lie, you will get this."

She pressed a button and Ryan's balls exploded in pain and he gasped."

"The more you lie, the longer the duration. The more you are honest, the quicker this teasing session will end, and you get to your reward. Understood?"

Ryan only nodded.

"I asked you a question!" Jen said, pressing the button and causing Ryan to cry out.

"Yes goddess! I understand!"

"Good," Jen said. "Let's begin. Are you a virgin?"

Ryan hesitated. He did not want to appear inexperienced or be seen by either of them as a loser for not having had sex yet, but that was the truth. But if he told them, what we would do with it. What would Amanda Think?

"Too long." ZAP

"Ahhh.... All right! Yes!"

Jen smiled. "Good boy."

"Prior to being caged, how often did you masturbate?"

Again Ryan paused and received a a slightly longer ZAP from Jen.

"Ok! What the fuck,. You're not giving me time to answer."

"You don't need to think up what we want to hear, you just need to answer." She zapped him again.

"FUCK! Three or four times a day."

Jen smiled and Amanda leaned down. "Really? Four times in one day."

"Sometimes more on the weekends..."

"It's not something to brag about," said Jen.

Jen continued the questioning. The machine began to do its job ever so well, bringing Ryan to very brink of orgasm, and then pulling him back. The denial and stimulation were building and his balls began to ache.

"What do you think of when you masturbate? And don't be generic, I want specifics. List the top 5 things."

Ryan shook his head. This was deeply personal and completely humiliating.

"Amanda. Me fucking Amanda in... in... the ass."

"And?"

"Amanda going down on me and then swallowing my load. God this is so humiliating."

"That's two."

"Being spanked sometimes, and being tied up and being made to service young women, like Amanda and you."

"Excellent. No points for sucking up though. And the final of your top 5."

Josh was struggling with the last one. He didn't want to reveal it.

"Stubborn boy!" Jen zapped and this time held the button for a full four seconds and Ryan thrashed on the table.

"OK! FUCK! Being pegged."

"Now was that so hard?" Jen mocked him and then turned the dial up on the machine making the edges last longer and longer.

"Do you want to come Ryan?"

"Yes please goddess. Please!"

"Now think carefully about this next question. You can come in the machine, and it will be quite the experience for you. Or you can wait until tomorrow and you can come in Amanda's ass."

"You want me to wait again?"

"No, I want you to choose how you want to come."

"Please Jen, I'm not sure I can make it until tomorrow. My balls ache already."

"You want me to release some of the pressure? Just a little maybe?"

"Yes. God yes. But I still get to come in Amanda's ass tomorrow? No more games."

Jen laughed. "There are always games. But you still will have that option, yes."

"Fine! Please take some of the pressure off."

Jen picked up a long needle and Ryan screamed his safeword. "AVOCADO!"

Jen put the needle down and laughed. "That was a test. I'm glad you passed."

"What? What test?"

"I wanted to make sure you would use the safe word when you really felt it was too much. I don't use needles, but I keep this around because it typically evokes that type of response."

"You're evil you know that."

"Yes. And I love it." Then Jen help up a small oddly shaped device and poured lube on it. "Now just relax." Before Ryan could object he watched as she inserted the device into his ass, slowly. She teased every inch and made it almost pleasurable.

She was watching Ryan closely, staring into his eyes. Then she felt his ass clench as she found his prostate, and the terror in his eyes was delightful.

"Wait! I'm going to pee!" Ryan exclaimed.

"No, it just feels that way."

Jen ordered Amanda to stop the machine and remove it from his cock. He was rock hard and purple from the teasing, and Amanda was careful not to push him over the edge. Jen continued and Ryan was forced to start at his poor neglected cock as Jen probed and then she found the right spot. His face contorted as he clenched again and a pitiful dribble of come leaked out of the tip of his cock only to drip onto his face. Jen continued to push and probe until she was able to extract three more dribbles and then removed the probe.

"How was that?"

"Weird, and incredibly frustrating," Ryan said. "Some of the pressure is gone, but it was not satisfying or any real release."

"Yes - that is the point of a prostate milking. It's how we keep you caged boys healthy without letting you actually come."

"But why?"

"You'll find out tomorrow."

Jen produced a bag of ice and shrank his cock quickly to fit back in the cage, and Amanda helped her lock it back in place. The released Ryan from the bonds on the table, and Jen walked both of them upstairs to the master bedroom where a huge steam shower awaited them.

"Enjoy a nice steam shower. Come down when you are ready. "You may serve Amanda however she desires."

Ryan said, "Thank you goddess." Amanda smiled and they turned on the shower and stepped inside.

The soaped each other's bodies and kissed several times before rising off and turning up the steam. There was a long bench at one end of the shower, and Amanda laid back on it. She spread her legs and Ryan needed no invitation to fall to his knees and devour her completely. Amanda rode Ryan's face to three wonderful orgasms before she told him to stop. She was full satisfied now, and they rinsed one final time before exiting the shower.

The evening was uneventful, the three of them watching TV and relaxing, though

Ryan was always the one getting a drink, or a snack for one of the girls. He rubbed both of their feet at one point and eventually fell asleep on the couch. He woke by himself in the living room, and went in search of Amanda and Jen. He found them in the kitchen eating cereal and talking, both wearing long night shirts.

"Good morning!" Jen said. "The coffee is over there if you want some."

Ryan went over and poured himself a cut of coffee and sat next to Amanda.

She smiled at him. "You slept a long time. It's almost ten."

"I was wiped out I guess. You girls take a lot of energy to keep up with."

Jen decided now was a good time to mess with him.

"Who said you could sit in my presence bitch. Get on the floor." she watched his eyes.

Ryan fumbled and got out of the chair and onto his knees.

Jen laughed and Amanda looked directly at her, "Come on!" She turned to Ryan, "She's fucking with you Ryan. Get up."

Jen laughed again. "You really are a total submissive. I love it."

They ate breakfast and Ryan and Amanda cleaned up before they want out to the pool for a swim. Ryan was on edge the entire time, afraid to ask when they could continue what they started yesterday. His cock was straining in the cage despite the cold water. It was Jen who finally spoke up.

"I'm impressed Ryan. You haven't begged once for your release. I really thought it was going to be the first thing you said this morning." She looked over at Amanda.

"You ready? "

Amanda only nodded nervously. She had never had a real dick in her ass, but Jen had certainly played with it and used her strap-ons enough times that she was certain it would be ok. Jen led the way back down the basement and she had Ryan help her bend Amanda over a bench such that her head was about waist height and Jen secured a ring gag in her mouth and buckled her legs and arms in tightly so she was completely helpless.

Ryan's cock was practically ready to explode as Jen took the key from around her neck and opened and removed the cage. His cock sprang to its full length almost immediately and Jen stroked it once.

"God that's fucking hot."

Amanda moaned from the table, a pang of jealousy overtaking her as Jen stroked Ryan a few times. Jen looked over to her.

"Maybe I'll let him fuck me instead, and keep you all tied up and needy."

Amanda shook her head, unable to speak, but wanting to convey her displeasure with that thought.

Jen laughed and went over to a set of drawers and removed a harness and strap-on that was only about a third of the size of Ryan's erect cock. She fastened it around her hips and strapped it in place.

She went over to Amanda and pushed it into her mouth. She gagged as the length bottomed out in her throat.

"Let's go Ryan. Come over here are get nice and wet and ready for her ass."

Jen stepped behind Amanda and donned a rubber glove, then poured a generous amount of lube over her ass and pushed a single finger in, making her gasp. Amanda nodded to Ryan as he placed his cock into the ring gag and slowly pushed it into her mouth. Her tongue immediately explored the tip and she began to swirl it around making Ryan draw in a sudden breath, not wanting the pleasure to end too quickly.

"I almost forgot," Jen said pulling her fingers from Amanda and removing the glove. She moved quickly over to a set of drawers against the wall, pulled out a thick rubber ring. She motioned for Ryan to pull out of mouth a moment and then stretched the ring around Ryan's entire shaft, pulled a little and pushed his balls though and then released it. It gripped him entirely, making his cock swell even larger.

"That's a cock ring. It will help you delay the orgasm that will likely build very quickly after all the denial. It's not going to stop it, but it will make it a little easier to control."

Ryan nodded and fed his member back into Amanda's mouth, Her tongue went to work again and it only took a few thrusts for him to pull out and take a slight break before repeating it over and over.

Jen picked up a leather harness and began to strap it around Ryan's chest.

"What are you doing?" He asked Jen.

"Just a little precaution to prevent anyone from getting hurt."

There was a metal ring at the back of the harness and she tied it to a rope hanging from the ceiling. It wasn't enough to restrict his movement, so he didn't think anything of it as he s positioned himself behind Amanda.

It was tight at first. He pushed slowly and Amanda moaned. Jen encouraged him standing in front of Amanda.

"Keep going, she's good."

Amanda nodded as best she could and Ryan pressed and felt the head of his cock pass through the tightest part, and as Amanda gasped he slid the rest off the way with little resistance.

Ryan's voice was shaken as he said, "Oh God! That feels incredible."

Jen smiled almost giddy as Amanda moaned when Ryan pulled out a little and then went back in. Slowly he developed a rhythm and began to fuck her ass. Amanda started moaning with each thrust. Jen picked up a vibrator and sank to her knees in front of Amanda. The moved it toward her clit and then told Ryan to pull out completely and then thrust back in.

Ryan was on the brink of orgasm as he pulled out completely and then pushed straight back in, balls deep as Amanda screamed and a thundering orgasm overtook her. Ryan repeated the thrust three more times as Amanda was coming and suddenly he began the most intense orgasm he ever experienced, lasting not the few seconds he has come to expect from year's of masturbation, but a euphoric orgasm that lasted almost a full 90 seconds and he actually cried out before he collapsed, the harness holding him up.

Jen removed the vibrator and began to untie Amanda as Ryan hung from the ceiling, completely spent and still experiencing the high of such a powerful orgasm. Amanda kissed Jen as soon as she was freed and then embraced her fully with both arms. "Thank you! God that was so good."

[To be Continued]