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Upskirt Shot Story

Fridays. Fridays were always the most interesting days for Sigma, ever since he met...him.

That was the only way he had to refer to the guy, just as 'him.' The feline wasn't even sure if 'him' was even a male, but he doubted that a female would want to see the things that he was asked to do every Friday.

The dark furred feline stood over a small box, sealed with a little lock. In his paw was a key, small and slightly shiny, with a curvy S emblazoned on the end. It was all he had on his person; whatever clothes he'd been wearing earlier in the day had been folded up and put away almost half an hour ago. They were locked away until 'he' said otherwise, which was usually at the end of the session that was coming up.

Despite how many times he had done this before, Sigma wondered if there was some way out of this. His fingers clenched down on the key he held, half considering putting it away. Just the thought of what he was about to do had him blushing already, and he knew how bad his cheeks would be burning if he went through with it again. The dark furred cheetah thought about this every time, and every time he almost threw the key away.

However, just like every time before, he slowly crouched down to the small locked box. He gripped the lock - heart shaped, just like the end of the key, and emblazoned with the same curvy S - and slowly turned the key in it. The soft click of the lock coming undone was almost deafening to him, and he half winced, half shivered as he slowly pulled the lock out of the way of the latch. Setting it carefully to the side, he slowly pushed the lid back. Soft threads of silk kept it from going more than halfway back, keeping the lid half raised so it wouldn't thump along the back of the small chest. He kept hold of the lid anyway, the wood something solid to hold onto, something he felt he needed at that moment.

Inside of the box were his Friday clothes, as he called them. 'He' called them something different entirely: the sissy clothes.

The clothes were soft, silky, satin in the case of the panties inside. It wasn't much, only a skirt and a pair of panties, with an anal toy off to the side. Sigma's blush worsened as he remembered where that was going to go, but he felt a little twitch back there anyway, a slight tensing of his hole. Even as he blushed, his body remembered last week, and how much it had enjoyed itself, no matter how humiliating it could be to wear the clothes that went with it.

He knew better than to waste time, to keep 'him' waiting. Reaching down into the chest, he pulled out the panties first. They were light, so light of a pink that they were almost white. They wrinkled slightly in his grip, but they were smooth again as he pulled them straight. Looking at them, he could hardly believe that he was about to put them on, but he knew that he would. He placed them on the floor gently, then slowly stepped into the leg holes, standing on his tip toes to make sure that he didn't trample the panties themselves. Slowly he pulled them upwards, the soft satin of the undergarments rubbing against his legs gently.

It always thrilled him to do this, no matter how much it also made him blush. The panties were so much softer than his normal underwear, and the slight smell that came from them - the scent of perfume and a different sort of detergent, something more feminine - just made him feel more...naughty, more..feminine. His body was already responding, his shaft hardening and slowly pushing outwards, upwards, forcing him to hurry, to pull up the panties faster to make sure that it was covered before it got too hard.

Thankfully he managed to get them up, suppressing a slight moan despite himself as the soft cloth slid over his shaft. It pressed it down tightly against his crotch, holding it flush against it. There was an obvious bulge in the otherwise feminine panties, as well as the slightest hint of a wet spot at the tip, and he was almost sure that he could see his shaft twitching, pulsing lightly under the panties. It was tempting to reach down, stroke himself, tease himself through the satin, but he held himself back. The feline didn't want to displease 'him'.

Even as he reached for the skirt to complete the little outfit, he felt his shaft rub against the panties from his slight movement. Trembling a little at the soft, stroking sensation, he held the skirt out in front of him. It was a deep sort of red, but not the sort that a man would wear. Only a female would wear something of this hue, this particular red. He didn't quite know why, or how, he knew this, but he did. More than that, he knew how feminine this skirt made him look, the way it hung around his hips and covered his legs. It was a short skirt, but it still covered just enough to entice.

Blushing all the while, he gradually stepped into the skirt, pulling it up and over his legs. Silky as it was, it rubbed gently against his fur, and he unconsciously started to purr. He barely noticed it, more intent on the feeling of the silk rubbing his legs, all the way from his calves to the thighs. Eventually he settled it a little above his waist, revealing even more of himself with the short length of the skirt, the bottom of the panties just visible, he knew from experience. He pulled the skirt waist tight, making sure that it was secure in place, before pulling his hands back.

That only left one thing in the box, and it was the object he both feared and anticipated most. He looked down at it again, taking in the sight of the knotted red toy in the chest. It was almost as red as a real dog cock, and Sigma had started to wonder what a real shaft would feel between his cheeks, what a real flow of pre would feel like as it pumped into him, filling him with that instead of some cool lube that he used at 'his' insistence.

The thoughts had never come around before he'd started acting like this,and at first he'd wanted them to go away. But lately, he enjoyed them. Even....even pleasured himself to them.

His fingers wrapped around the toy agonizingly slowly, his face on fire like he was groping a real male rather than just a toy replica of one. His imagination filled in the details, the throbbing that he felt whenever he touched his own cock; the little pulses of blood flowing through it, making it harder; even the feel of veins rather than the smoother feeling shaft before the knot. He clenched his fingers around it, squeezing the toy tightly, but the firm material refused to give under his tight grip.

It took him a few moments to pull himself back from his own fascination with it, and he shook his head. The call would be coming soon; he needed to be ready, and he still had a few more things to do.

Reaching down with his free hand, he grabbed a bottle of lube that was also kept in the chest, just towards the back, usually covered by either the skirt of the panties. A slight glance confirmed that there was enough left in it for this session as well as a few more, but he would need to get it replaced before too much longer. The thought of going to a store and picking up more lube - of being made to go in and get more lube - was enough to bring his blush back at full force, his face burning up with embarrassment at the mere thought of going in there. Yet, as much as the thought embarrassed and humiliated him, it excited him too, as his throbbing shaft attested to. It pushed and pulsed against the light panties that covered it, and bulged out the front a little more.

Forcing himself to be satisfied with the light, almost non-existent stroking that he got from his cock sliding against his panties, Sigma hurriedly pulled the lid closed and locked the chest again, setting the key down on top of it. Dildo and lube in hand, he made his way to another room.

On the far side of the room was a computer with a large monitor and a camera hooked up to it. A slight cushion with some towels laid out near it was in the middle of the room, and the camera was pointed right at it. It was so familiar, yet he still shivered in excitement, just as he did every Friday.

The monitor lit up as a voice call suddenly tried to come through, and Sigma hurried over to it. It was 'him', it had to be. 'He' was the only one that would call at this time. The feline threw the toy and the lube down on the small cushion and slid himself into the chair by the computer, clicking the 'respond' button. "Hello?" he said, his voice quiet and soft.

"Hello, Sissy," the voice on the other end said. It was deep, masculine, almost comically so. But the way that the owner of the voice handled him, teaching him, it never tempted him to laugh. At least, not after the first time. "Are you ready to give me the weekly show, and learn your next lesson?"

"Yes...yes sir," Sigma said after a moment.

"Good. Turn on the camera and get on your cushion. I want you to show me what a good little sissy you are, and how well you've been learning your lessons."

It only took a moment to click the camera on, and only a quick glance to make sure that the red light was on. It was, so he got down from the chair and walked back to the cushion. He could see himself from the stomach down on the camera, and slowly lowered himself so that he was fully on screen, from his face to his feet completely viewable by the male on the other end. He could only imagine what 'he' was doing, but he couldn't stop himself from wondering. Was the other male stroking himself to what he saw? Did 'he' think of Sigma as a male to humiliate, or as just a sissy to be used? Or, most embarrassingly, did 'he' see the cheetah as a real female, with his pussy between his butt cheeks rather than between his legs? That thought was so wrong, so naughty, yet so good, and he moaned softly, his hand reaching down the front of his skirt to softly rub against the bulge of his shaft.

"Ah ah ah, Sissy," the voice said, stopping him after he'd barely gotten in a single little rub. "That's not the way that sissies have fun. You know what you're supposed to do." Sigma slowly turned to look at the dildo at his side. "Yes, that's what you're supposed to use. It's what you need now, isn't it," the voice asked as the feline slowly picked it up. "I can see it in your eyes, Sissy. That appeals to you even more than stroking your own dick, more than pushing it into someone. You need to use that. You need a cock in you. Fake or real, you need it."

The words were familiar, but the feelings they inspired were not. Sigma had never felt the same rush of excitement when 'he' had talked like this before, but he felt it now. His hole twitched again, and this time he felt it clearly, the hunger and heat down there. No longer just curious for something new, he did have a hunger, a real need for that cock. Whether it was fake or real, whether it was a detached toy or a real shaft attached to another male, he wanted it inside of him, wanted to feel it spreading him open, teaching him how to submit like a good little sissy, to be true to his new name.

Under the encouragement of his viewer, he slowly uncapped the lube bottle, letting the slippery stuff inside come free. He splashed it into one hand and then brought the dildo up with the other. He stroked his fingers along it a few times, admiring the shaft, before grabbing it tight, jerking it, stroking it, imagining that it was attached to a nice big male who would be panting from what he was doing.

Soon it was slick and shiny looking, the hard material glimmering a bit as if it had been worshiped in the mouth of a devoted cock sucker for long minutes. He stared at it, his breath coming hard, ragged, shaky, unable to fully contain his excitement. His cock pulsed in his panties, but it didn't leak. He barely noticed; all of his attention was on what was about to happen, where the toy was about to go.

Getting up in a squatting position, Sigma pushed the toy back between his legs, pushing it so that the tip was angled right towards his rump. Under the view of the camera, he slowly pushed the panties off to the side, exposing the space between them. He moaned softly, slowly lowering himself down towards it. The tip was cool, but it was slick, and his hole welcomed the touch of something against it. The lube was good, strong, and the toy immediately started sliding in with only minimal resistance from him. His mouth fell open, and the blush seemed to fix itself to his cheeks, not growing any brighter, but not dissipating either.

As he slowly slid back onto the toy, he lifted the front of his skirt with one paw, holding the other down at his side. He made sure that his bulge in his panties was on full display, feeling it bounce a little bit inside the tight satin confines. It throbbed eagerly, pulsing harder with every inch of toy that he managed to get in.

"Yes, such a good little Sissy," 'his' voice said through the speakers. "This is what sissies do. They are there for other males. They're there to look pretty, and they're there to serve. And you're learning how to serve very, very well, aren't you, Sissy?" Sigma nodded with a soft moan as he pushed down all the way to the knot, feeling it pressing against his rim before he pulled up again. "Yes, very good, very good, little Sissy. You know your place. You know what you are. What are you, Sissy?"

Sigma blushed a little bit, but slowly, softly spoke. "I...I'm a sissy...a girly sissy...who wears panties and loves cocks in me," he whispered.

"Louder, Sissy. What are you?"

"I'm a sissy. A girly sissy...oooh...who wears panties and loves cocks in me," he said, moaning softly.

"Louder. What are you?"

"I'm a girly girly sissy who wears panties and loves cocks in me!" he nearly shouted as he pushed down against the toy, the knot stretching him out for a second and popping inside. Sigma's eyes went wide for a moment before he fell back, sitting down and driving the toy just that little bit deeper. He felt like he might climax, but it was just short of being enough. He just needed something...just a little something more....

'His' voice chuckled through the speakers, Sigma just barely able to hear him. "Good, good, you're progressing well, Sissy," 'he' said from the other side. "You know, I think you might be ready for your next lesson. Now, ride that thing a few more times, show me what you can do."

Sigma blushed, but nodded, slowly rising up to continue. He still had an hour to go for this session, after all, and he wouldn't want to make 'him' upset.