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?"