Caught - Sex Stories

Caught

... After I put on my uniform, I strolled around the house until going to my s****r's room. She had a huge mirror with tons of make up. Through years of experimenting and trial by errors, I had discovered the perfect combination for myself. I hardly used any of her important make up and the affect was quite pleasing. I went back to my room and applied the last few things. I had also just ordered a wig online as well. I had never worn a wig before, but I was curious about the feeling of having long hair. Since I always kept my hair short, a wig seemed to be the obvious solution. The hair was a light brown/dirty blondish color and measured several inches past my shoulders. I went to my mirror and adjusted it and tied little pigtails on it to enhance the whole schoolgirl look. The whole process had taken well over three hours. I didn't mind the long process, however. The process was part of the fun. My parents had a full-length mirror in their bathroom so I trekked my way to their room. What I saw staring back at me was a shock. The total affect of the uniform, make up, and wig almost made me gasp. I actually looked like a six-teen or seven-teen year old girl. I always had a smaller frame than most guys and my facial characteristics were less pronounced, but I never imagined I would be able to pass so easily for a young lady. I don't mean to sound egotistical, but if I hadn't known it was me under everything, I would be checking me out. For the next hour, I lounged around the ...

... house and watched TV enjoying the feelings of being fully dressed. I was trying to decide when to begin the next part of my evening. I froze several keys attached to strings the night before. I decided to check my other materials. As I went to my room, I felt my skirt brush against my pantyhosed legs, making my cock spring to life. The ecstasy was incredible. I began to worry about how long I could hold out before I needed to release. If I started the next phase of the evening, I wouldn't be able to do anything about my hard cock. Instead of going to my room, I headed towards the freezer and retrieved one of the ice cubes. I grabbed a cup and hurried to my room. I opened my drawer and removed several layers of clothing before finding my stash. Over the years, I had collected three pairs of handcuffs, two pairs of leg irons, five chains, and numerous locks. I would have preferred the snug feel of rope against my skin, but I had no partner and it's very hard trying to bind oneself with rope. Cuffs were easier to use and held no chance for escape, which stirred strange desires within me. I felt my stomach drop as I positioned myself on the floor. I placed the cup on my desk with the string dangling down in easy reach. I figured I would have about half an hour to forty-five minutes before I could escape. I cuffed my legs together with a pair of leg irons. Next, I cuffed my hands behind my back, my stomach churning once again as I felt the last click and realized my helplessness. ...