When I was still in school, I did a little housekeeping for a few different people in my neighborhood. I figured it was a good way to get some extra cash for the summer. One of my client’s names was Jake. He was a middle aged bachelor. who lived alone just a few houses down from me. One day while I was putting away laundry in his room, I noticed that the big cedar chest at the foot of his bed was missing the lock that had always been on it. Now, I know it isn’t polite to snoop, but I was really curious as to what was in that chest. So I opened it just to take a quick peek, and to my surprise, I found much more than I ever expected. In that chest lay an array of bras, panties, and stockings. There were also dildos, vibrators, lube, handcuffs…I opened it wider and reached down to sift through the contents, and I immediately realized that I was looking Jake’s very own kinky little toy box.
About the time the realization dawned on me that Jake was a sissy, I heard a horrified gasp from behind me. I turned to look at him, holding up a large black dildo and a lacy red thong from his secret toy box in my hands. The look on his face was priceless. His cheeks were bright red, and his eyes were wide with terror.
I smiled really big and while pointing the dildo towards him, and asked “Well, well, what is this?”
At first he was scared speechless. But finally, with as much voice as he could muster, he begged, “Please don’t tell anyone about this. I’ll do anything you want.”
I laughed, and tossed the panties at him, and told him the only way I would keep his little secret was if he would dress up for me. And he did just that. He stripped down to nothing, and put on that red thong, and a matching bra. I noticed that he was completely shaven, and his toes were painted with a deep red polish. He told me that standing in front me dressed like that made him feel like a dirty slut. I just laughed, and told him that I hadn’t even begun the process of making him my dirty little slut yet.
“But very soon you will prove to me just what a sissy bitch boi you are. My boyfriend will be here any minute to pick me up, and I was going to invite him in. If you want me to keep my mouth shut about what a fucking sissy perv you are, you’re going to have to let him do whatever he wants to you. But until he gets here, why don’t you get on your knees and crawl over here, and suck on this fat black dildo.”