Diane was tied over a horse in Michael's basement, sweating. Completely naked, the horse was wide enough to support her whole weight, and long enough that she could rest her head on it; just at Michael's hip height, her groin was on the very edge of the end. Both legs and hands were tied to it and her breasts felt squashed flat, but at least he'd taken off the bondage rope. Michael had left her awhile ago, but there was plenty for her to look at. Before leaving her down there he'd told her to get a good look around while she could, since later she probably would have her attention on other things. On the walls there were whips and paddles, riding crops, ticklers, and lengths of rope. There were shelves with various dildos, probes, butt plugs, and other items that she could see were there but couldn't make out what they were. Other than the horse she was tied on, there was also a large wooden frame, a hook in the ceiling with a chain hanging down from it, some kind of harness or swing, and another structure. It was about the same height and length as the horse she was on, but was much thinner, and the top part of it was like a triangle, but smooth and rounded instead of pointed. She had no idea what it was for, and wondered if maybe it didn't have anything to do with her. Although, that seemed unlikely with just about everything else in the room obviously being for her.
She squirmed uncomfortably, wondering how long it would be before Michael came back. At least he'd let her go to the bathroom before tying her up, but the more time he left her to think, the more she imagined what he might do to her. And the hornier she got, and also the more nervous and anxious. He'd taken out the dildos, but really that just made her feel empty, and in some ways more uncomfortable because she'd gotten so use to the feeling of being full, her mouth was full though. A new kind of gag had been placed in her mouth, it was shaped like a small penis and was about 3" long, covering her tongue but without making her gag.
Thoughts turned round in her head. When they had first come home, Michael had had her fill out a sheet he had which listed activities, and she had to answer either yes or no, he said it had been to establish their limits. Fortunately, she'd found out that he had no taste for certain deviant acts either, and some things were to be used only for punishment (not very consoling when she knew this weekend was mostly going to be about paying for her transgressions during the week.). Still, the list had held a few surprises for her, and she was curious to see how everything would be implemented. She was also unsure of her bravery in saying yes to things like being whipped and cropped, now that she had time to contemplate the actual instruments. But she hadn't wanted him to be disappointed in her, so she'd said yes to everything that she thought she could at least handle, even if she might not necessarily enjoy it.
Finally (it was actually only about 20 minutes, but to Diane it felt like at least an hour) Michael returned, wearing nothing but a black silk robe that hung down to his knees, rippling around him as he walked. Diane hummed her pleasure at the sight of him, but quickly lost her happy feeling as he looked at her and then reached up to take down a paddle from the wall.
"So. Today, you did not catch up on your work. All week you have worked at a much lower rate than you needed to. This weekend is going to be about you learning that when I tell you to do something, you will do it, even if you are distracted. Maybe, if you are very very good, then on Sunday I will have a treat for you." Diane vowed to herself that she would be good... whatever that entailed. Not just for the promised treat, but also because she didn't want him to decide that maybe she wasn't worth having around. To disappoint him would be terrible.
WHACK!
The paddle hit her ass. WHACK! WHACK! WHACK! She jerked as it covered the entire area of her ass, it hurt more than she'd thought it would, but she felt that she was bearing up bravely. Having a spanking at the end of each day at work had probably helped. After 35 hits with the paddle she had started screaming behind her gag, even though the beating was being spread out over her whole ass, each hit was really starting to smart. By the time he reached the end - 50 - it felt as though her ass was on fire, and there were tears streaming down her face. A smooth hand caressed her burning ass, and he chuckled, "You should see the color of your ass, a nice cherry red. And that was just the paddle, your spanking for today's lack of effort." One finger slipped down to stir her pussy juices, and she realized that the hard spanking had made her very wet.
While his fingers began to violate her pussy, his other hand began to alternatively caress and lightly slap her reddened ass, the combination of pain and pleasure making her gasp, twitch and moan. Then she stiffened as the fingers in her pussy began transferring some of her pussy juices to her ass, rimming it with wetness. More chuckles at her discomfort.
"If I were you, I'd try to loosen up a little. Since you were so bad this week, I decided that you'll be doing without extra lubrication for you ass, so you might want to be more enthusiastic about what you do get." Fear at the thought of having him try to shove that huge dick up her ass dry - and certainty that he meant what he said - made her try to relax her ass hole. Still, it clenched and unclenched as he slowly pushed one large finger, as she tried both to expel the invader and to allow its entrance. Her hole had already shrunk back to its normal size after he had taken the butt plug out - not that the butt plugs had ever been all that big. Compared to the ones up on the shelves, the ones he had used on her had been pretty small. Two fingers, both coated in her juices, pushed up her smaller hold, twisting and turning inside of her; she spasmed around them, and wiggled, trying to relieve the pressure on her poor asshole. Then he pulled both out, and she could hear the robe slip to the floor beside them, feel him moving behind her; she tensed as she anticipated the assault on her second hole.
Instead, he pushed swiftly into her pussy, feeling its tightness pulse around his dick at the unexpected invasion. A few quick strokes to completely coat his dick in her juices and he pulled out and began pushing lightly against her ass hole. With his hands on her hips to hold her, he began the slow push forward, barely nudging in and then pulling away, before nudging forward again, slightly more this time. She could feel her ass opening and closing, then it felt like one long push, and her ass burned as the head popped in, and her ass closed around it. Arching her back and biting down hard on the rubber penis in her mouth, she tried to deal with the pain. It hurt more than she thought it would, after all the stretching his fingers and the butt plugs had done... she felt spread wider, and more full than ever, and he only had the head in. Slowly, agonizingly, he began sawing his dick back and forth, each time pushing another half inch in, even though she started becoming accustomed to the girth, the new length filling her would make her wiggle and squeal each time. It was as though he was drawing out the pain and discomfort for as long as possible. Finally, his hips were against her ass, she was panting for breath behind the gag, feeling stuffed and overly full.
