Flat Chested Ladyboy In Stockings Gets Nailed

She was glaring down at us and holding her hand like she had just snapped her fingers. She smiled a very cold smile at us both and said, “And they will both do much better in the beautiful butt contest.” She watched as holly gasped and I looked back at her wide-eyed, not knowing what she meant. “I wasn’t going to enter them,” she said evenly, “but they have just displeased me and I will enjoy seeing guy fucks shemale their beautiful butts displayed for everyone’s amusement.” Actually, it was called, “The Cutest Ass Contest,” and like about everything else at the club, there were six contestants. I have no idea who the others were... except holly. But I didn’t even know which one she was because I couldn’t see anything once they got me prepared. When we went backstage, Mistress Gloria was leading holly and Mistress Sam was leading me. They had attached leashes to our collars just to add to the humiliation. Mistress Sam strapped me into this really strange-looking thing with a lot of padded shelves. I’m not exactly sure how it worked, but I ended up strapped over one of Small Boobs the shelves with my knees on another and my arms crossed above my head on another. Then they cumshot cranked a bunch of handles and turned me almost upside down so that my ass was really high in the air. At that point, Mistress Sam said, “Time to add a little decoration to help you win.” She came around in front of me and showed me four paddles. One had really sharp ridges on it that stuck up almost an half-inch from the paddle itself. Those ridges would really cut and bruise your ass. The second was divided long-ways into three segments. The center segment was leather while the outer two segments were wood. The center segment was slightly longer and had little pyramid-shaped metal things near the end of the leather. Evidently the wood would hit first and then the leather with stockings the metal. That one would really tear up your ass. The third paddle had holes of various sizes drilled through it. The smallest was about a blowjob quarter inch. The largest was at least two inches. Those holes would cause welts and blisters with every swat. The fourth paddle had a heart carved into it. It wasn’t quite a hole because it was only cut about half way through the wood. Mistress Sam flipped that one over so I could see that there were two smaller hearts carved into the other side. “Which one should I use?” she asked aloud. I thought she was just thinking to herself and didn’t say anything. Then she slapped me with her hand, low on my thigh. “They all will hurt,” I said quickly. “They’re supposed to hurt,” she replied curtly. “Which one do you think I should use?” I was thinking fast. “If my ass is supposed to look cute,” I answered, “then you shouldn’t use any of the first three. Emily yelled. Kaylie pulled back and lightly blew on her teacher’s clit. I had an eight day load and knew I would not last long. No one cumshot has taken such good care of me…. My car came Small Boobs equipped with heated seats and the girls turned theirs on. After a while I still couldn’t concentrate blowjob so I went to the family room and turned on the box. The pain became exquisite and absolute. guy fucks shemale Ashley I’m taking Jim stockings to bed with me. He will be well taken care of. It was one of those offices with windows and open blinds to view the waiting room and service areas. “Relax! "Surprise," I giggled and started groping for his erection as I stepped out of my shoes. "That was amazing and you are really beautiful. The teenager mowing her lawn had become her sexual fantasy.