Crossdressing Housesitter

There was a caller today that was a crossdresser, not an uncommon thing by any means. It’s astounding how many men enjoy dressing up in women’s clothing. This crossdresser though had a bit of an unusual story. His boss had asked him to housesit while they were away on vacation and he took that time to rummage through all her drawers and try on her lingerie and stockings and prance around in them. He never did get caught doing this, but it was his fantasy that she had come home early and caught him wearing her lingerie and what would she have done had she walked in on this little scenario.

He liked to imagine her being shocked, surprised, and horrified stumbling upon this unexpected scene in her own bedroom, and that she would turn him into her pussy worshiping sex slave for doing this. He’d have to lick her pussy on demand any time she wanted it done, and she’d also use a strap on, on him as well. Her stash of sex toys was one thing he;d found in her drawers he’d been rummaging through and he saw it in there and fantasized about her fucking him with it.

If she was very mad, she might even bring in one of her male friends to have him give blow jobs to and service sexually anyway they saw fit. He’d be serving all of them, and be grateful to do so. All the while dolled up in her lingerie and his cock as hard as a rock as she fucked him and he stroked himself. He found himself willing she would come home early from her trip and do these things to him. In all likelihood she wouldn’t have made him a sex slave, she’d likely have fired him and maybe called the cops, but hey, ones have their fantasies.

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