The Secret Date - Part 1

Cameron opened his drawer and took out his favorite pair of panties. He slid on them on, pulling them snugly up against the buttplug that he had inserted that morning. He reached back into the drawer and chose a chastity device , the small pink one that fit familiarly over his shaven little dick and around his tiny balls. As he continued putting the rest of this one, routine outfit on, he thought about how devastating it might be for the girl he hoped to pick up to see it once he began taking off his clothes, if he should be so lucky to get to that point. He remembered how the last girl had gasped at the sight of his panties, gave an embarrassed gasping laugh when she saw the butt plug protruding from behind, the chastity device sticking out into his panties; he could still feel the intoxicating wave of shame that had swept over him when he felt her reaction. Cameron had loved the anticipation of it all, the honest interaction they had at the bar, how he had played the part of a straight man trying to just pick up a girl, how she had no idea what he was waiting for her to see, how he had no idea what it would lead to, but knowing full well, hoping even, that it would not lead to him somehow fucking her. He was fully aware that he was addicted to being rejected by women, denied pussy, and doing it all willingly. It was a shame too, because she had been such a nice girl, homely and kind. She had turned out to be horny as well, and she would have eventually fucked him, but his plan to be discovered as a sissy, for her to see everything that was hidden beneath his regular male clothing, had worked. Her reaction could have been disastrous. For any girl to be thrown for such a loop could have made them angry and made them possibly even attack him. But it wasn't in this girl's nature, and she had politely dismissed him after seeing what she saw.
"That's not what I was expecting," she had stammered in the dim room.
"What hadn't you expected?" Cameron had inquired, craving the burning shame that would come from her specificity. He ached for her to humiliate him, say something direct and outright about him being a sissy, a loser, a boy who dressed like a girl and wore panties and a chastity device. But she had been too jarred to do just that.
"This... stuff you have on," she had managed to say. "Please just leave now... this is so embarrassing."
It having been his first time doing this to a girl, he hadn't pressed any further, and, satisfied with the whole experience, slid his jeans back up over his stockings, garter belt and panties, and had left. As he walked home that night, he had relished the whole experience. Reliving each moment, he had masturbated, assturbated, of course, as he only allowed himself to be pleasured through his "sissy butt" as he called it, which he had learned to do from all the videos he watched online. And when he finally came through his chastity device, he moaned, and reveled in the shame and humiliation of it all, loving the feeling of having exposed himself as a sissy, and being able to finish by cumming only through anal stimulation, alone at home.


Now, as he put the finished putting on his female and male outfits, he craved that same shame and humiliation again. Cameron hoped that this time, maybe, it would be even better. He hoped that maybe this time, the girl might not ask him to leave so soon, that she might make him stay so she could ask him questions about why he might possibly do this to himself. That she might laugh at his weak responses, that he could feel her scorn and derision as he replied by saying things like, "Well, I'm a sissy, so this is how I like to dress; I don't think I really deserve women except to be rejected and mocked by them; I've never had sex with a girl, and I expect to be pussy-free for life; I want to have sex with real men - Maybe you can help me find one and show me how to suck his dick and fuck him?"