f***ed to cross dress on Halloween - Sex Stories

f***ed to cross dress on Halloween

... anxiously with a towel wrapped around him. “You smell nice. Now, let me put this on you so it won’t spoil the surprise.” I said while tying the black satin blindfold firmly around his head. “Yes, mistress.” He was in a meek and obedient state, just the way I like him to be. With the thick satin blindfold tied tightly around his head, Mark could not see how much trouble he was in. With the thick satin blindfold tied tightly around his head, Mark could not see how much trouble he was in. “Follow me.” I instructed my pet as I grasped his hand and led him into the bedroom. With a quick tug I removed the towel that was wrapped around his body. Quite literally his safety blanket fell to the ground. He let out a moan and cringed a little. “Oohh, I like how smooth you are.” I stated while inspecting his handiwork. In front of me stood a male in his early thirties who was completely hairless from the neck down. “Now, be a good boy and spread your legs for me. Right, that’s it.” I encouraged him. The amount of accesoiries, toys and pieces of clothing that I had prepared while he was in the shower was impressive. To start things off, I grabbed a big steel butt plug and applied some lube. With my left hand I put pressure on his shoulders, forcing him to bend over while whispering “Now, be a good boy and grab your ankles for me.” Eagerly, my little pet obliged and he was now showing off his naked butt. He probably had some idea of what was to happen next, he was no virgin when it came ...

... to his little naughty hole. The cold tip of the lubed butt plug touched his ass and I could sense the shivers going through his body. I applied some pressure with my right hand while I grabbed his balls with my left hand and squeezed a bit. “Accept your new cold friend, sweetheart.” I said with a smirk on my face. I was enjoying this. “Aahh” he called out as the plug was slowly sucked all the way into his ass. *SLAP* With a lot of f***e, I slapped his ass with my right hand as I still held on to his precious balls. “Be quiet.” I hissed. “Sorry mistress.” He replied, almost whispering. This cold toy had already gotten the attention of his manhood. It was growing, which was something I did not want just yet. While I expertly grabbed the first piece of the next torture instrument with my right hand, I squeezed a little harder around his balls. I could feel his pulse through my tight grip. His erection responded by slowly becoming smaller and retreating. I fit the outer plastic ring around his balls and base of his cock while grabbing the cage, a new chastity toy I’d purchased recently which we’d had the not so nice pleasure of experiencing a few times before. With a little lube on the inside, it quickly slid over his hard member. Mark was aware of what was happening and wanted to protest, but before I let him say a thing I squeezed just a little harder while whispering “Don’t even think about complaining. We have a long day ahead of us.” I let go of his balls, hearing the relief ...