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One was a 22 year old bear who’s cock was way to big to be real. He was really eager though so I decided to meet him and headed out just 20 min after starting to chat with him. I got to his place and made my way to the basement suite entrance. I was fully dressed and in my wig with just a hoody and sweat pants coving my little schoolgirl outfit I’d chosen to wear. I knocked and he opened the door almost instantly, he was huge, 6’5” and muscular with a hairy chest and shoulders, I felt like such a pathetic sissy standing in front of him. He invited me in we made our way to the bedroom. I quickly shed my outer layer and he complimented me on my slutty outfit and my makeup. He poked fun at my little caged cock poking out from under my skirt and sat on the bed pulling his sweats off as he did. His cock was only semi hard and already it was the biggest cock I’d ever seen... I was almost nervous but knew that even with that big of a cock my sissy pussy was trained well enough to please. I will see you Friday.”So after another long day at work on Friday I decided to head over to Ryan’s house to talk with his brother and hang out for a while. I like Ryan even if he isn’t letting me have sex with him so I figured it would still be a fun night. I show up at his house and his little brother, Caleb, answered the door, “Hey, Dan, Ryan’s not here right now.” Caleb is a really nice guy. He is a perfect gentleman and always respects his elders. Unfortunately he always seemed really sad. Even at times when he probably was happy his face still had this deeper sadness to it. I don’t really know how to describe it, but he always seemed to be in pain. He had just turned fourteen in April and looked it. Like his brother he, too was thin and athletic, but he lacked the muscle tone. He looked a little scrawny with very thin arms. Despite looking weak he was actually fairly strong for his age. He was still very boyish looking, but you could tell he was getting ready to.
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