A New Dynamic

The restraints made this particular activity more difficult, so Jessica put them to the side. "Let's revisit these later. You certainly have more things to spank someone with than I've ever thought of. What's this?" She held up something that looked like a large X.

"It's an over-the-door restraint system. It's for tying someone up while they're standing."

Jack said that while trying his best to look up from his vantage point hogtied on the bed.

"Set it up."

Jessica unclipped the hogtie and Jack slowly righted himself. He opened the door to the closet, added the anchors at the top and bottom, and closed it again. He managed to clip both his ankles to the bottom of the X, then secured his right hand. Seeing his efforts, Jessica walked over and finished his left.

"Hmm. Progress, but needs something else." She walked back to the case and Jack tried to study her and divine what she was thinking. When she came back, she put a blindfold on him. Suddenly deprived of sight, he got even more excited. He tried to listen to the rustling to figure out what she might try next.

"Let's see how you react to this," she mused as she attached a nipple clamp. She heard the sharp intake of breath, then repeated it on the other side. They were connected by a short chain. She tried pulling on it a few times to see what different reactions she could get out of Jack.

Then, thinking she wanted a souvenir to help her process things later on, she took out her phone and snapped a couple pictures. Lastly, she leaned in, bit his ear, then whispered, "Don't come." He only had time to answer "Yes, ma'am" before he felt her lips around him. It felt incredible. He couldn't help but moan.

Jessica had never been a huge fan of giving oral, but she enjoyed how he was reacting, what she was doing to him. She didn't even mind the precum that seemed to be steadily leaking. After a few minutes, she could tell that he started to gyrate faster and moan a little more. She leaned back and asked, "Are you close?"

"I can't remember being this close. Please can I come?"

She just laughed and said, "Nope. Wouldn't want the night to end so soon."

She walked away and Jack heard her ask, "How does this work?"

Jack laughed too once he had recovered. "I can't see anything."

"Oh right." She took his blindfold off, tossed it on the bed, and kissed him slowly. Finally, she held up the chastity cage so he could see. It was clear silicone and quite small; there was a key in it. "How does this work? There's no way your cock will fit in there."

"Not right now. When you take the key out, it splits in two. One piece goes on behind the balls, then the other piece connects to it. I have the clear silicone one so I can go through a metal detector if I need one; actually went to an amusement park without any issue once. You can't be erect when it goes on."

"Hmm. If I wanted to test it, what would you suggest we do about this?" She ran one finger up the length of his shaft.

"Well, we could have sex?"

"Nice try. What else would work?"

"Spanking might work if it was hard enough... The other idea people often use is ice."

"That could work. Lay on the bed."

Jessica unclipped him from the door and led him to the bed. He connected his legs and showed her how to tighten the straps. Jessica did the same with his arms and tightened everything so he could barely move.

"It would be a shame to not use this opportunity, right?"

Jessica slowly disrobed until she matched his state of undress. Slowly, she crawled up his body, stopping to kiss his cock, his abused cock, and his neck. Finally, she was kneeling over his head. She asked, "Do you want to get me ready?"

"Yes, ma'am. Please, I'm dying to."

Looking in his eyes, she believed him and she lowered herself down so her mound was over his mouth. He was enthusiastic. She was moving quickly over his face and he tried to keep up. After several minutes, she was able to climax, grabbing his head and forcing him deeper.

Once she recovered, she climbed off of his face and mounted him. She guided him into her with one hand while she pulled the chain of the nipple clamp with her other. She pulled it high and tight, but he was not able to go anywhere with her on top of her. She leaned in and said to tell her if he got close. She tried to play with the nipple clamps to keep him distracted so that he didn't finish too soon. After several minutes, she started to increase her pace.

"OK, OK. I'm going to come if you keep going."

"Damn," she said, slowing down. "I guess you're done with this part of the evening."

"Yes, ma'am," he said, frustrated. He thrust upwards at nothing in frustration as she put the blindfold back on. Jack has no idea how much time passed before she came back in. He gasped as he felt bags of ice on his package.

"Try to stay still so this doesn't fall off. I have some more research to do."

"Yes, ma'am."

She left him to go through the rest of his container. The strap-ons were interesting. She hadn't really ever given much thought to wearing one. She put one together with a dildo that was similar in size to Jack. Looking at the contraption and Googling on her phone, she realized that there was a pocket for a vibrator. She installed one, then tested it. She liked the way it felt. She felt powerful.

Once she was done, she removed the ice. Jack was as flaccid as she had ever seen him. She held up the cage; it would be a close fit. She thought it might work, especially if Jack had worn it before.

"I'm going to try to put the cage on you. Try to control yourself or we'll have to start the ice all over."

"Yes, ma'am."

"How does it go on? I have the ring, but it doesn't look big enough?"

"It only works if you put one ball through at a time, then the shaft."

"Romantic," she quipped.

"Sorry. There's no other way to explain. If you uncuff me, I could do it."

"No, I want to understand the whole picture."

With that, she started trying to push one of his testicles through the ring. Jack groaned softly as she was a little less gentle than he was, which made sense. She couldn't feel it. In a moment, the base ring was in place behind his balls. He started stirring to life.

"What did I tell you?" Jessica asked, as she replaced the ice to counteract his excitement.

"Sorry. It's kind of a catch-22. Once you're touching me down there, it gets excited. Doesn't really follow directions well."

Jessica took the ice off one last time and forced the tube on. It was tight, looking smaller than his very full balls at the moment. Once she got it locked, she shouted, "Yes!" and pumped her first. She took one more picture before continuing. His cage was extremely visible in his current predicament.

She finally removed the nipple clamps and he groaned as the blood returned to them. She playfully bit and sucked them, as her hand cupped his balls. He became as erect as the cage would let him. As he tried to get erect, the ring was pulled more and more tightly against his balls. He wouldn't ever be able to cum while wearing this, she thought.

Taking one picture to more clearly remember his predicament, she asked, "Is it really safe to wear that for more than a few hours?"

"Yes, it's totally safe. Not always comfortable. Almost always wake up early in the morning when it tries to get hard and can't. Sometimes, it can get to the point I almost forget I'm wearing it, but if I have any thought that gets me aroused, I instantly remember. In this case, I'll think of you because you have the keys."

"Interesting. Keys? There's more than one? I just saw the one in the cage."

"There's an emergency key in my nightstand."

"Got it," she said after a moment. "How do you feel knowing I have the only keys to your freedom?"

"Nervous," he admitted. "Excited too. How are you feeling? I know this is probably not where you were expecting the evening to go."

"Understatement of the year. I'm good though. Cautiously optimistic you might say. And you aren't getting the keys back tonight."

"Good, although when I played these scenes out in my head, I wasn't already desperate to come when I started wearing the cage."

"Poor baby," she purred sarcastically, kissing him while grabbing the cage. "When was the last time you came?"

"Five days ago, when I last saw you. I was trying to already act like I was wearing one."

"Doesn't count, but it's good to know. I'm going away for a while soon, so you won't get out before I get back. There are a couple more things I'd like to try tonight. How would you suggest I position you for a spanking? I kind of like having you tied up."

"There are a lot of different ways. Over your knee is the most common. The easiest is using these same restraints, but face-down over some pillows so you get a better angle. There's also bent over the bed or the diaper position; that's where the person is restrained on their back with their legs up. It's supposed to be pretty mortifying."

"I'll remember that, but for now just roll over once I let you free and don't touch the blindfold.

"Yes, ma'am."

It proceeded just as she instructed. Once he was face-down, she had him lift his ass so that she could put a few pillows under him, then reattached the restraints. He was at her mercy. They were finding out that they both liked it that way.

"There are 6 implements here:

a paddle

a flogger

a crop

a wooden spoon

a hairbrush

a bathbrush

"I'll start with my hand and add your belt too. Why don't we do 10 of each?"

"Yes, ma'am."

"I wasn't really asking you. We both know you think you want this."

She knelt on the bed next to him, careful not to poke him with the strap-on. She did not want to ruin her last surprise. She steadied herself with one hand on his lower back. Without any further ado, she came down on his left cheek. The crack was much louder than she expected. She came down on the other cheek and eventually found a good rhythm. After 10, her hand was definitely feeling it. She was glad that there were implements, because she didn't want a sore hand in the morning.

Jack's ass was nicely reddening and warm to the touch. He'd managed to stay stoic throughout. Jessica picked up the paddle. It was light, only big enough to hit one cheek at a time. She was able to get a little more force and got a grunt out of Jack. After 20, his ass was definitely getting red.

"Wow. Your skin is so pale, your ass is practically glowing. Are you ok so far?"

"Yes, ma'am. I'm alright."

He sounded pretty chipper, so she believed him. She let her fingers explore his caged cock and balls, his ass, even gently going over his asshole. They'd never played that way, so this was a new experience.

She switched gears from implements that thudded to those that were more stingy. After 10 each with the crop and the wooden spoon, he was trying to move his ass to get some relief and she even noticed his toes curl. She was convinced that he would have kicked his legs if they weren't restrained.

"Ready for a surprise?"

"I think so, Ma'am."

She picked his belt up from the floor. This one she could use standing up. She expected it would be difficult. She hadn't anticipated enjoying it. He let out a loud "fuck" after the first and didn't stop there. He was cursing a lot and breathing heavily by the end.

"Still ok?"

He nodded. She spanked him once more with the belt, for an eleventh surprise. He cried out, but she leaned in and whispered casually in his ear.

"I didn't hear you."

"Yes, ma'am. I'm ok. Definitely more intense than I'm used to, but I'm ok. Just two left, right?"

"Yup, the hairbrush and bath brush. Actually never seen one of those in person. It looks like it will sting."

"You're right. It does. I've tried it on myself, but can never get the angle right for it to be effective."

The hairbrush hurt but the bath brush was excruciating.

"I think you should ask me for more. What do you think?" Jessica asked sweetly.

He nodded, but this was suddenly more real that it was in his fantasies. "Please, I'm begging you, spank me an even hundred times. We're at 81, and I like round numbers. I never run more or less than an even mile. Plus, after everything I sprung on you today, I think I deserve it. Don't you?"

"OK, you convinced me," she smirked, though he couldn't see it. "Any guesses what I'm going to use?"

"Your hand?"

"You wish. Count down from 19."

He cursed as the bath brush landed, then said "19, Ma'am." By the time they got to 15, he was straining at the restraints. He hadn't bought the cheap ones, though, and they held. He was nearly in tears by the end, although he managed to hold it together. She rubbed his ass, then stepped back.

"What do you say?"

"Thank you Ma'am."

"I'll bet you still feel that one tomorrow. I'll give you a minute to collect yourself."

Jessica snapped one picture to remember just how red she'd managed to make his ass then walked out of the room. He probably did need a minute. Besides, she needed to mentally prepare herself for the last experiment. She wanted to surprise Jack, so she didn't want him to hear or see anything. She knew that if she removed the blindfold, he'd see the strap-on and definitely get excited. She didn't want him to have a clue, though.

She'd told him about her first and only anal experience. Her partner had not been gentle and it had been quite painful. She wanted his experience to be better. She thought it likely would be. The plug was on the girthier side and had likely stretched him out enough to accommodate the 6 inch dildo she was wearing. She opened the lube outside of the bedroom, so he wouldn't hear. She caught sight in the hallway mirror of what looked to be her jacking off the cock she was wearing. That was a trip. When she was ready, she turned on the small pocket vibe. She enjoyed the sensations, but could tell it would be more effective once she was thrusting and it was forced against her clit.

Walking back into the room and asked how he was feeling.

"I'm ok. My ass is on fire though. When are you going to let me out?"

"Soon, I think."

She knelt behind him and left a hand on his ass. With her other, still coated in lube, she unceremoniously violated him with just a finger.

"Oh, fuck," he said, as she let him get used to the feeling, then started gently moving back and forth."

"Are you ready for the main event?"

"God, yes."

She knew how excited he was and forgave the slip in protocol. She spread him with one hand and guided "her" cock with her other until the head was forced in.

"If you want the rest, you'll need to beg me for it."

He was stunned. He wouldn't have guessed she had this side to her. Dirty talk was not something they had gotten into.

"Please, ma'am. Fuck my ass."

"Do better," she prodded.

"Please, fuck my ass hard and make me your bitch. I'll do whatever you want."

"If you want it that badly..." She slowly forced it in, until it was all the way in, and the vibe had nowhere to go but against her clit. She brought it all the way out and back several times, savoring his reactions and moaning. She wondered if this was what it was always like for guys.

Once she was sure he was used to it, she increased her tempo. Finally, once she couldn't resist any longer, she was slamming into him. It started out just as something she wanted to do for him, but her own orgasm built and built. She climaxed and forced the dildo all the way to better grind against him and the vibe.

Once she came back to earth, she disconnected the strap-on so the dildo. She then connected it to him, so the dildo couldn't fall out. She just had to take one more picture to complete her set. Then, she kissed him on the cheek and went to take a shower.

Jack didn't know what to do with himself. Most of his fantasies were coming true live, though he was desperate for an orgasm. He had no idea how long he was left tied up, in a cock cage, with a vibrating dildo stuck in his ass. He couldn't complain though. He was in heaven. It was likely about half an hour. When Jessica removed the blindfold, the dildo and harness, and the restraints, she was showered and fully dressed. He hadn't realized how stiff he'd gotten.

They kissed deeply. Breaking the silence, she said, "I have to leave soon. I have an early flight."

"I forgot about that. When are you back from your work trip?"

"It will be a week. Are you ok after everything?" she asked.

"I'm fantastic. How are you? You were more into things that I expected."

"I didn't expect that either. I really enjoyed it though. I'm going to bring your keys with me on my trip."

It wasn't a question.

"I am going to think over everything while I'm gone. When I get back I'll either give your keys back or I won't."

Their eyes matched. "Yes, ma'am."

* * *

A week later, Jack was nearly climbing the walls he was so horny. He picked Jessica up at the airport and they had a nice lunch. They caught up and enjoyed each other's company. Once the meal was nearing her conclusion, she brought up the topic they'd both been waiting for. She unbuttoned the top two buttons of her blouse and a key was dangling on a necklace between her breasts. He instantly tried - and failed - to get hard.

"I've read and thought a lot about what happened, what we did, last week. I think I have a decision."

"I'm listening."

"I really enjoyed the activities. The more I thought about it, the wetter I became. I think I rubbed one out every day over the last week. How about you?"

"Can't say the same, though I have replayed it in my mind 100 times."

"Every time I looked at the pictures, I had to take care of myself."

"Pictures?"

She brought up an app on her phone and handed it to him. His eyes went wide as he went through everything.

"I've decided I can't do something a little bit. It's either all the way or not at all. So, I'm going to offer you the key."

Jack looked down, disappointed, but not wanting to show that to Jessica.

She continued, "Option A - you take the key, unlock yourself once we get home, and we don't do it again.

"Option B - you give it back and I keep it. It becomes real. You may not wear it all the time, but it should be your default from now on unless I tell you otherwise or take it off of you. Do you understand?"

"Yes, ma'am."

With that, she took off the necklace and held out her hand. Jack swallowed, thinking of the possibilities and repercussions, then reached out and closed her hand around the key. She smiled.