My Sister's Boyfriend by Larry Malone Even when I was very young, I loved to play with my asshole. I was always, what I later found out, was called “anal erotic” I loved having something in my little ass hole. 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 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 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 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. 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 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. He smiled, patted my ass and got up to clean up and left. By that time I knew I really enjoyed getting fucked and decided I shouldn't have to wait until Jess saw with my sister. It didn't take long for me to find classmates and school mates who had similar interests. I always acted as if I really didn't want to get fucked so the guys wouldn't think I was a fag so I always made sure I had to be convinced or tricked. And over the years it worked. That kept my hungry asshole full of cum any time I wanted it all the way through college. A few weeks later, when my sister was again babysitting me, I was awaken to a loud fight I heard from my sister's room. I don't know what it was about but I did hear my sister tell Jess to “get the hell out!” I jumped out of bed and went to my door and saw Jess leave my sister's room, I opened my door and motioned him to come into my room. I was nude and got a little stiffy and asked him not to leave and led him over to my bed. Without saying anything I laid face down and spread my legs. Jess got the idea and wasted no time taking off his clothes and getting on top of me. He asked me if I had any lube, which I did but before he used the Vaseline, he spread my little ass cheeks and started to lick my hole. He slowly started to tongue fuck me which I thought was the best and then changed positions, got on top of me and lubed my hole and his rock hard 7” cut cock. Slowly he started to enter me and his tongue prep (and my solo ass play) worked to loosen me up, he was sliding in easily and I was feeling no pain only a satisfying pleasure of warmth fullness. I started to moan since it felt so good that he told me I had to keep quiet so I buried my face in my pillow. Since he hadn't first cum in my sister like other times, his cock was harder and he fucked me longer and deeper. It felt fantastic but he was so horny that he didn't last very long and for the first time I felt his full large load deep in my hole in multiple shots. It felt great and I loved to feel the throbbing cock pumping cum into my ass. I was disappointed that he didn't last longer since I was enjoying it so much. I thought he was going to pull out and leave like before but I was wrong. He stayed deep in my hole on my back and stayed semi-hard as he kissed the back of my neck and wiggled his cock in my cum flooded hole. I squeezed my internal muscles and fucked him back by lifting up my little ass. In a little while he was rock hard again and started to fuck me full strokes. He fucked me for another half hour before he added his second load deep into my hole. Only then did he get up, dress, and quietly leave. I found out later that the fight was about him again trying to get into my sister's asshole for anal sex which she didn't want so that ended he and my sister's dating for good. He met me after school one afternoon and told me he would still like to get together with me and do our “thing.” Although I never mentioned my other anal adventures in the school I felt really happy and grown up that an “adult” wanted to share with me something I loved doing. We arranged that on certain days when I supposedly had “band practice” he would pick me up after school or whenever I could get away we would meet and he would take me to his place and he would fuck me until it was time for me to go home. We became very close and he taught me everything about sex including swapping blow jobs. Over the years as I grew older and my cock grew larger, I eventually swapped ass fucks with him and others as he let me take his ass cherry and we switched back and forth. We kept that up until I went to college and he moved away.