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 retentive titillating"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 nose when I was really picayune. It felt so good I always tried to repeat that feeling with my finger's breadth, the enema nose, carrots, legato reefer and as I grew older, the psyche of my G.I. Joe action figure.

When I was about nine, I had my first anal sex even though I did n't know what it was and I had n'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 champion over and sustain sex in her room all evening until just before my parents came back. My room was flop next to hers so I heard everything that went on but I never said anything because I did n't call back it was any of my business organisation and after all she was"sr."and could do"those things."Plus, she left me alone in my elbow room to do what I wanted which was to envisage 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 before than everyone and slept nude. One dark when Sis was"baby sitting"me since our parents were going to be real previous getting rest home I had my first anal experience just by chance. My sister was entertaining her then 17 year old young man at the time, Jess. As I got the narrative hebdomad later, after their common lengthy sex play and after he shot his load into my Sister without a safety ( she was on the oral contraceptive pill ) he was on his way to the lavatory to clean up when he passed my elbow room. He told me, my door was undefendable a petty, my night light was on as he passed and when he looked in, he could see my fiddling 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 did n't cognise why but even though he just had a solid 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 picayune ass looked just like my baby 's but firm and fuller. He told me he entered my room, closed the doorway and knelt by my bed and just could n't aid himself but rub his putz in my ass crack. His cock was still liberally lubricate and coated with my sister 's pussy succus and in add-on his tool was still oozing the in conclusion of his cum from his flood tide. He said the heat from my little ass got him fully erect. He easily slid his hammer along my ass crevice and said I wiggled and moaned a slight and he swears I pushed my little ass out to meet his stopcock. I did n't recollect a thing. He said he got more excited and continued to rub and lubricate my crack until he separated my two ass boldness and aimed his shaft at my little tap star topology. He then told me he just naturally started to bear on in and since I did n't wake up he kept pushing until the capitulum popped in. He said he froze worried that he may take in hurt me but again swore that instead I moaned a small, 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 picayune ass. He pushed in slowly until he was fully in and he said I was so tight and my cakehole 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 pick up. He never mentioned anything to my baby and when he left, he was worried of what may come about 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 warmheartedness at my hole but I did n't intend 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 question of G.I. Joe that made it easy for me to train Jess'cock.

The adjacent time Jess was visiting he paid a little More attending to me but I was n't shady 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 clip he was with my sister and my parents were n't home base I always woke up the future break of day with cum dribbling out of my prick but I no longer was feeling any tenderness.

It became a regular thing for him to take care forward to fucking my little ass a few times after fucking my sister and looking forward to having second base in my besotted hole. One night for some cause, I was n't deeply gone and woke up as he was fucking me. I felt his peter deep in my ass and I really enjoyed it and without knowing it I started to agitate back to get to a greater extent of his cock deeper into me. The more I did that the harder he fucked me and he then realized I was n't numb anymore. He put his hand over my backtalk 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 footling muddle. He whispered he was sorry and asked me not to evidence my sister. I turned and said, that was n't a problem since I enjoyed it a lot and would care him to do it some more. He smiled, patted my ass and got up to make clean up and left. By that meter I knew I really enjoyed getting fucked and decided I should n't bear to waitress until Jess saw with my sister.

It did n't claim long for me to chance schoolmate and schoolhouse mates who had similar pastime. I always acted as if I really did n't want to get fucked so the hombre would n't think I was a fag so I always made sure I had to be convinced or tricked. And over the class it worked. That kept my hungry asshole full-of-the-moon of cum any time I wanted it all the way through college.

A few workweek later, when my sister was again babysitting me, I was awaken to a loud fight I heard from my sister 's room. I do n't have it away what it was about but I did hear my baby tell Jess to"get the nether region out !"I jumped out of bed and went to my room access and saw Jess bequeath my baby 's room, I opened my threshold and motioned him to come into my room. I was nude person and got a little stiffy and asked him not to pull up stakes and led him over to my bed. Without saying anything I laid face down and unfold my leg. Jess got the idea and wasted no metre taking off his clothes and getting on top of me. He asked me if I had any lubricating substance, which I did but before he used the Vaseline, he spread my slight ass boldness and started to work my hollow. He slowly started to tongue fuck me which I thought was the in effect and then changed positions, got on top of me and lubed my maw and his rock hard 7"cut cock.

Slowly he started to enrol me and his tongue prep ( and my solo ass play ) worked to tease me up, he was sliding in easily and I was feeling no pain only a satisfying joy of warmheartedness fullness. I started to moan since it felt so good that he told me I had to celebrate quiet so I buried my face in my pillow. Since he had n't outset cum in my Sister like other times, his cock was harder and he fucked me longer and bass. It felt antic but he was so horny that he did n't in conclusion very long and for the initiatory time I felt his wide great load oceanic abyss in my hole in multiple jibe. It felt great and I loved to sense the throbbing cock pumping cum into my ass. I was disappointed that he did n't live longer since I was enjoying it so lots. I thought he was going to pull out and leave like before but I was wrong.

He stayed deep in my golf hole on my spinal column and stayed semi-hard as he kissed the back of my neck and wiggled his prick in my cum flooded hole. I squeezed my home heftiness and fucked him back by lifting up my petty ass. In a little while he was rock hard again and started to fuck me full-of-the-moon strokes. He fucked me for another half hour before he added his second load deep into my pickle. Only then did he get up, clothes, and quietly leave.

I found out later that the fight was about him again trying to get into my sister 's son of a bitch for anal sex which she did n't want so that ended he and my babe 's geological dating for sound. He met me after schooltime 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"banding practice"he would pick me up after shoal or whenever I could get away we would fulfill and he would take me to his lieu and he would screw 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 shtup with him and others as he let me take his ass cerise and we switched back and forth. We kept that up until I went to college and he moved away .