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It started when my Mom stuck a Vaseline lubed finger in my hole to ease in an enema nozzle when I was really little. It felt so good I always tried to duplicate that feeling with my finger, the enema nozzle, carrots, smooth sticks and as I grew older, the head of my G.I. Joe action figure. When I was about nine, I had my first anal sex even though I didn't know what it was and I hadn't looked for or expected it. How it happened is this story. My sister was teens sixteen and when ever our parents were gone she was expected to baby sit for me. When she did, she also took the opportunity to have her current boy friend over and have sex in her room all evening until just before my parents came back. My room was right next to hers so I heard everything that went on but I never said anything because I didn't think it was any of my business and after all she was “older” and could do “those things.” Plus, she left me alone in my room Girlfriends to do what I wanted which was to imagine what my sister and her guy were doing to make those strange sounds and for me to play with my little wiener and ass hole. Of course, I always went to bed earlier than everyone and slept nude. One night when Sis was “babysitting” me since our parents were going to be real late getting home I had my first anal experience just by chance. My sister was entertaining her then 17 year old boyfriend at the time, Jess. As I got the story weeks later, after their usual lengthy sex play and after he shot his load into my sister without a condom (she was on the pill) he was on his way to the bathroom to clean up when he passed my room. He told me, my door was open a little, my night light was on as he passed and when he looked in, he could see my little naked ass sticking out from the edge of the bed as I lay sleeping on my side with the bed linens off me. He told me, he didn't know why but even though he just had a satisfying fuck and had shot a load of cum into my sister, his semi-hard boner got real hard when he saw my little butt. He said my little ass looked just like my sister's but firmer and fuller. He told me he entered my room, closed the door and knelt by my bed and just couldn't help himself but rub his cock in my ass crack. His cock was still liberally lubed and coated with my sister's pussy juice and in addition his cock was still oozing the last of his cum from his climax. He said the heat from my little ass got him fully erect. He easily slid his cock along my ass crack and said I wiggled and moaned a little and he swears I pushed my little ass out to meet his cock. I didn't remember a thing. He said he got more excited and continued to rub and lube my crack until he separated my two ass cheeks and aimed his cock at my little pink star. He then told me he just naturally started to push in and since I didn't wake up he kept pushing until real the head popped in. He said he froze worried that he may have hurt me but again swore that instead I moaned a little, wiggled and pushed back to take more of him into me. He said when the head was in he paused to see if there was any reaction from me or if he was hurting me but since I was pushing back, he assumed I liked it so he kept on sliding in slowly. He told me later that my sister would never let him do her anally so he really wanted to get into my little ass. He pushed in slowly until he was fully in and he said I was so tight and my hole felt so hot, he could only fucked me a few strokes when he shot a load of cum deep in my ass. sexy He said he pulled out and immediately went to the bathroom to clean up. He never mentioned anything to my sister and when he left, he was worried of what may happen later if she or I ever found out what he had done. As it turned out nothing happened. I woke the next day with cum dribbling out girlfriend of my ass as I went to take my morning piss and I felt a little tenderness at my hole but I didn't think anything of it and just thought it was because “I was maturing” or because I had been playing with myself. I guess it was the fact that I could take the head of G.I. Joe that made it easy for me to take Jess' cock. The next time Jess was visiting he paid a little more attention to me but I wasn't suspicious at all, he was a nice guy and I sorta liked him. He never mentioned what he did that night and there were only a brief discussion if I was sleeping alright, which I told him I was. But I never connected the fact that every time he was with my sister and my parents weren't home I always woke up the next morning with cum dribbling out of my asshole but I no longer was feeling any tenderness. It became a regular thing for him to look forward to fucking my little ass a few times after fucking my sister and looking forward to having seconds in my tight hole. One night for some reason, I wasn't deeply asleep and woke up as he was fucking me. I felt his cock deep in my ass and I really enjoyed it and without knowing it I started to push back to get more of his cock deeper into me. The more I did that the harder he fucked me and he then realized I wasn't asleep anymore. He put his hand over my mouth and whispered into my ear “Shh” and fucked me until he shot his load. When he finished, he lay over me and slowly pulled out, I could feel his cum oozing out of my little hole. He whispered he was sorry and asked me not to tell my sister. I turned and said, that wasn't a problem since I enjoyed it a lot and would like him to do it some more. Something must have happened with Brian, She deduced. Did that mean incest was a tradition in Clint's family. “I guess that would be OK, Mom and Dad won’t be home for another hour. This was a problem, a series problem. He then leaned over and took my cock in his mouth. Just as I started to go, the door opened, and Candice came in. The cold air hit her in the chest and another shudder flowed through her body. Still wrapped around my torso she broke her kiss and smiled at me, “Is it okay if I can play around with your cock today Daddy?” “Having a family take care of is a great motivation for a guy to excel in life. The platform was only long enough to support her from her waist to real her shoulders. “Well, when you caught me masturbating, that when I was first attracted to you and that’s why I was moaning your name. I must have moved my feet apart a bit because I could tell her fingers were getting wet. “I'm not fucking for votes.” Alicia shyly walked into the large office. Those legs, and her sexy skill on the volleyball court, had landed the 18 year old a full scholarship at the university in Richmond. You will give up your life for him. Brie shook her head. I see McHenry kiss, Sharon, quite nicely and offers to call a cab for her. Mark and Tim subtly looked at each other in astonishment at girlfriend what Ron had uttered. It is not very often I do it, but I arrange for a teenage girl from up the road to come down to babysit the kids until later on. What’s more teens I remembered to shout ‘Priapus’. Mein Göttin. Now Harry felt uneasy. Maddi started to pout with her puffy lower lip turning her face into a frown and said in a whiny little voice, “Answer the question daddy!” Be good, follow the laws.” "You know," she said, leaning towards me. "I don't usually have sex on the first date," she informed Girlfriends me, placing her palms on my tits.