Safeword: Storm Clouds(57)

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."