She patted him on the ass and then walked to the wall and gathered a few things from a drawer before walking back to him and making sure he watched her put on a pair of medical gloves. She saw him hump the table once and his eyes got big – now he understood why she had oiled up the area under him. When he humped the table, it felt good. She wiggled her gloved fingers and then smiled at him, running her hand from the top of his head all the way down to his ass as she walked around behind him.
"Not a word, Eric. Unless you want to tell me one of your safewords, not a word comes out of your mouth."
She lubed up the fingers of her right hand and then squirted some lube on the outside of his ass before shooting some inside. One finger wasn't a problem, even though he was tightening up really badly.
"Eric, I need you to relax. Push, like you are trying to push me out. Yes, there you go, that's it."
She worked him for a bit with one finger and saw him fighting to not hump the table. She could smell his growing arousal, so she added a finger and then felt herself smiling as he moaned. Once he was comfortable with two fingers and was still fighting to not hump the table she said, "Eric, fuck the table, hump it. Go, NOW."
He started to slowly hump it and she decided he needed a threat. "Do it in earnest unless you want another finger. Move your ass, fuck the table, like you mean it. I want you to come all over the table Eric." She pegged his prostate, "I want you to come with my fingers in your ass."
She’d restrained him, but she still wanted him to actively participate. And she wanted him to start identifying something in his ass with pleasure, with orgasm. She loved the feel of his ass around her fingers, the conflict she could smell in him, and the arousal she smelled. He was so horny, but he was fighting it. He didn’t want to be horny with something in his ass. She kept encouraging him to move, threatening something larger in his ass if he didn’t start moving, and finally he started humping in earnest. Once he lost himself in the sensations, he didn't last long, less than two minutes. And when he came, he did so with a roar, going crazy on the table, spasming around the fingers she held in his ass. She knew she needed to get him aroused again pretty quickly so she immediately got him up from the table and cleaned him up before seating him in the bondage chair. This chair reclined him back at a bit of an angle so his torso wasn't sitting up straight, though his bottom was sitting on an even surface. She restrained his ankles and thighs out to the side so he was spread wide, also attaching his wrists to his outer thighs while she was at it. Then she restrained his waist and chest. She reached for a warm baby wipe and cleaned his dick and balls once again, then went down on him until he was hard. She considered biting him to give him a hard on, but she would save that for another time. Tonight they needed to know the hard on was all him and wasn't metaphysically or chemically induced. Once he was hard she teased him a bit and then got up to go get her kit with the sounds, plugs, and inserts. She wouldn't make him take the medical sounds yet, she needed to work up to those.
As she opened her kit in front of him she said, "These are my personal toys, they do not stay in the play room. They are autoclaved after every use, and if they go a time without use they are autoclaved again." She pulled one of the penis plugs out, "I put these through the autoclave last night after you went to sleep. They are sterile. I will start with the smallest to see how you handle it. Eventually I will hurt you with these, but tonight the goal is discomfort, the goal is sensation, not pain. Feel free to speak at will now Eric, just do so respectfully. If it hurts, tell me. You don't have to use a safeword if you don't want, just tell me it hurts, or say ouch, or something."
"Yes ma'am."
Kendra took him into her mouth again to give his erection another boost. He wasn't soft by any means, but he wasn't rock hard anymore, either. So she worked him with her mouth for about thirty seconds until he was rock hard again and then pulled up and used vamp speed to get everything cleaned and lubed and then stopped the vamp speed just as the smallest one was an inch from the tip of his cock. She paused for about five seconds and then began to slowly insert it. He sucked his breath in and held it as she did, but didn't say anything. She smelled adrenaline and arousal, with a hint of fear. Just what she wanted him feeling. When it was about two inches in he said, "Oh. God."
"It's two thirds of the way in Eric, you can do it. You are pleasing me so much, you wouldn't believe how hot this is making me."
When it was all the way in and he felt the flared tip of it resting against the top of his dick he started breathing heavy, trying to put all of the senses together. She didn't smell pain, not much, anyway. There was arousal, and he was rock hard, but he hated that he was rock hard, too, so there was a lot of conflict. Some men got hung up on the fact that their cock was in essence being fucked. They were being required to take something into their body, into their sexual organ, and some men got too hung up on that to be able to enjoy it. She didn’t think that was it, she thought the conflict was just in enjoying something when he wasn’t running the show, when he was the person experiencing the sensations instead of giving them. She wanted to fuck him, but she knew she needed to make more of a
Mistress
impact than she had. She intuitively realized she needed to assert her dominance with some pain, not just with sensations. But first, she loved watching a man trying to take something into his cock, loved the groans as she did something he felt was so unnatural. Eventually she would build him up until he could take larger sounds and plugs, and she would bring him to the point where he could wear a penis plug for an extended period. But for now, he needed to learn to deal with the small stuff.
"It's okay if you like it. You don't have to hate this Eric, there is nothing wrong with enjoying this. In fact, I love that you like the way it feels. It means it's time for something bigger."
"I don't think I can take anything bigger, oh God, Kendra, Ma'am, I don't think I can."
"Let's try. If you can't then there are other fun things I can do to your cock, but let's give it a try and see if you can."
When she pulled it out she could tell it really did something for him, even though he was trying to not show it. She went up two sizes, knowing he could take it. She was tempted to go three, but didn't want to push things, she was going for discomfort tonight, not pain.
She lubed everything and began inserting. Very slowly. This one would look like jewelry once it was in, with a pretty little jeweled flower sitting at the top of his cock once it was all the way in. He was still hard as a rock and he was in some pretty major discomfort and she wasn't sure if he'd make it or not. At about an inch and a half in she reached down and gently caressed his balls and then moved up and worked the base of his cock as she slowly let gravity do its thing up above. She let the last inch go in fairly quickly and then started jacking him off pretty good once it was in. She knew he was close so she stopped and stepped away, leaving him sitting there without her touch. He looked up at her, so uncomfortable, so aroused. She walked to the wall and got a small flogger. Not a mean one, in fact, this was about the gentlest one in the whole playroom, made for sensation instead of pain. She didn't really want to hurt him at this point, she wanted him to learn to relax under a flogger, and this was the perfect way to begin teaching him to do that.
Eric’s eyes were on her as she walked back to him, and she felt her own arousal level go up when she saw the submission in his eyes. He was her captive, with that pretty plug in his dick. She leaned down to give him a kiss that she hoped showed him how turned on she was. Just as he was processing the kiss and learning there is a difference in kissing someone and in being kissed, she pulled the pretty jewelry out all at once. He half screamed into her mouth, not in pain so much as surprise. She got another warm baby wipe and cleaned the excess lube off, then trailed the flogger at his hands so he could feel the strands.
"You know enough about floggers to know this one is mostly for show and not pain. I'm going to whip your cock with it, but I'm going for sensation and not pain. When I'm done with this one I will use a regular cock whip to give you five lashes. Those five lashes will hurt. If you can take those five lashes and stay hard then I will fuck you. There are bars behind you at the perfect height for my feet and hands so I can fuck you right here without having to move you. You can stop things without taking those five lashes, but if you end the scene you won’t get that. I’ll untie you and hold you and give you lots of TLC, but there will be no fucking, and no orgasm by my hand or my body. Understand?"
"Yes, ma'am."
He flinched for pain when the first strikes of the flogger fell, but once he realized it didn't really hurt, he relaxed. She kept at it until he was used to it and even seemed to be enjoying it. This was the beginnings of trust, she’d told him it wouldn’t hurt, and even though he thought it would, he’d realized she was right. The trust aspect was such a huge part of the turn on for her. That someone would willingly allow her to do extreme things to them, and trust her to not hurt them. Trust her to take care of them. Trust her that it would be good, even if it hurt. When she felt like he was to the point of wanting more than the sensations of the soft flogger she reached for the cock whip and said, "Five strikes Eric. Then I fuck you. Take it for me. Take the pain."
At the first strike he sucked in a breath, at the second he gasped. But his adrenaline levels spiked, and she knew he wasn't going to safeword. The third had his eyes watering. She stopped for about twenty seconds to give him a chance to compose himself and said, "Two more", and then gave them both in rapid succession, each strike twice as hard as the first three had been. She then tossed the flogger to the side and grabbed the bar that ran behind the chair at the same height as his head and swung her feet up to the one just behind his lower back, settling her boots on the bar so the heels acted to help hold her on the bar. She let go with one hand and held his dick out so she could sit down on it, and then sank down onto the hard length of him, all in one motion. She paused for just a few seconds and then started pistoning up and down on him as he moaned in pleasure. She did that for a few minutes until he was beyond rock hard again and then reached for the nipple clamps that were hanging over the bar she was holding on to. She stopped moving on him, sitting on his length and pulled the clamps down with one hand so he could see them. She still had the bar with her other hand for leverage, but she was mostly balancing her weight on his dick now as she pulled the clips down and put them first on one nipple and then the other. They weren't super strong, but strong enough for real pain, not just discomfort. He sucked in his breath in pain and she raised and lowered herself as she said, "Do you see storm clouds Eric? Do you want the scene to end?"
"No, ma'am, no storm clouds, but that really
really
hurts."
The sound of his voice, straining to take the pain, almost made her come right then, but she just said, "I know."
And she started riding him again, in earnest this time, saying "You don't have permission to come until after I've come twice, and then you may come whenever you wish. But those clips aren't coming off your nipples until you come. I want you to orgasm with them on."
Kendra came almost immediately, as she knew she would. As she approached her second orgasm about five minutes later she could feel him straining against the restraints, wanting to be able to move inside of her but unable to because of the way she‘d restrained him. She knew he was close, and as she started to spasm she felt him letting go inside of her. She came hard, but still managed to keep an eye on him, since she was supposed to be the one in control. As soon as they had both stopped spasming and she was sure they were done, she stood beside him and then released the clamps before immediately using the quick-release function of the wrist cuffs. She casually gave him permission to rub his nipples if he wished while she released him the rest of the way.
When she'd released all of the bondage points she picked him up like a baby and carried him to the large padded bondage table and laid him on it. She removed the wrist and ankle cuffs and then crawled up beside him, leaned across his chest, and whispered into an ear, "I'm hungry Eric, let me give you one more orgasm."
He didn't open his eyes, just lazily moved his head to give her access as he said, "Yes, ma'am."
She sank her teeth into his neck and he began coming almost immediately as she drank from him.
Kendra felt their auras mixing again, felt his life force mixing with her life force. She drank slowly, letting their aura's mix and mingle with each other. It felt like their souls were dancing. Their aura's didn't merge into one, but that was okay. Kendra knew it wasn't far off, she'd never felt this close to someone this soon.
When she was done feeding she cleaned him up with warm baby wipes again and then covered him up with a flannel sheet and snuggled against him until he dozed. When she was sure he was deeply asleep she got out the bleach mixture and cleaned the equipment they had used. She knew he’d be more comfortable in her bed, so she gathered the things that were hers and went to the hooks on the back of the door to get the robes that she'd placed in there earlier. She put hers on and then roused him enough to stand him up and help him into the one she'd brought for him. She walked them back to her room, mostly supporting his weight, and put him into her bed and cuddled with him until he was asleep and then grabbed her laptop and stayed beside him until he awakened two hours later, wanting food.
Kendra had started keeping a few items of human food in her mini-fridge for him, so she pulled out some bread and sandwich meat and cheese and mayo to make him a sandwich. She also kept some greenish yellow sports drink handy for him to help him build up his fluids. Once he'd eaten she asked him if he was ready to talk about it.