My Sister's Boyfriend

889Report
My Sister's Boyfriend

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.

Similar stories

Pigslut

I was gangbanged by 37 men in a filthy VIP room in the top of a bar room in New York, my husband took me to a party and left with another blonde girl, I sat at the bar all alone when 15 men approached me, they told me I was very beautiful and asked if they could take some pictures of me, I said ok, but they said it was too crowded in the bar can we go to a room where it's a little more quiet, I said ok, one of the men took me upstairs, to a dirty...

810 Views

Likes 0

An Incest Birthday Chapter 17

An unfortunate accident kept me away from the computer for a long time, but I'm all healed up and ready to get back to writing. I just hope I am as close to where I was writing wise before my abrupt disappearance. So after over an 8 month absence, the story of Rita and Randy Stevens continues right here, hope you enjoy it. I stirred in my sleep, waking up when I felt something push at my chest over and over, to the point where I had to address the issue. With blurry eyes I looked through the darkness until they...

383 Views

Likes 0

Surviving Dawn part 1

Today started just like every other Wednesday in recent memory. I woke up at 2pm, got ready, let the dogs out, and left for work. I arrived at work at my usual 3:11pm, and walked across the parking lot feeling good and soaking up a little sun. When I got to the basement and walked into the maintenance shop; I heard my boss babbling on about the local news report. I started my standard mundane routines when I heard thunder outside. I assumed that now would be the best time to get my chemical readings from the pool, under the impression...

172 Views

Likes 0

The Wood

It was cold. I lay hidden behind the bush close to the grassy path lining through the dark wood, it was my fifth night waiting. Often times a man or a group would walk past, but that wasn't what I was here for. It wouldn't be long - maybe tonight would be my night. I sat patiently, eager for the sound of footsteps. I checked the time... 12:54.It seemed quiet for a change. But then I heard the rising sound of faint footsteps followed by the crack of a few twigs. Then I seen her. Down the path to my right...

138 Views

Likes 0

Pounded at the shelter

I am a 35 year old man who lives alone in a secluded cabin in the woods. I am 6'1 with blond hair and blue eyes. I have never had a problem bringing ladies home. I am a Veterinarian and have an office in the city. I also do volunteer work at a dog shelter on the weekends. The owners rescue dogs and find homes for them once I have examined them. Some come in pretty bad shape so they take a little longer to heal. Others are beautiful dogs that were simply abandoned somewhere. The nearest neighbor lives 15 miles...

210 Views

Likes 0

Ruby's New Life Ch. 15

Days went by; I was left out of all discussions as to what my future would hold. I was allowed to do all of the shopping so I could earn Tavern time and video store time. They deemed it necessary for my mental health. It was also good for business. I was quickly becoming very popular in town and there was a following of men who kept tabs on where I would be working and when. They also resumed my anal training so that my body would be ready and willing as it should be, regardless of what they decided. I...

202 Views

Likes 0

Addiction_(0)

Enjoy the story and please leave a comment. Addiction “So Doc, ahh crazy question - is it possible to be um, like, addicted to a person?” It was a crazy question and Tom was somewhat embarrassed by even asking it, but it was a question that he had been wondering about for days now. The doctor, actually a psychologist, was a bespectacled balding man in his fifties, who had heard a whole lot of crazier things in his twenty odd years of practice. He was aware that Tom was serious and he needed more information before he could give an answer...

210 Views

Likes 0

Debauchery: The Invitation

Debauchery: The Invitation ~Prologue~ I pulled up to the huge mansion in my car. Valet was waiting with smiles on their faces. “Hello.” The young man said opening my driver side door. I grabbed my bag and purse. “Here is your ticket, enjoy your evening.” He said. “Thank you.” I smiled He hopped in my Buick Enclave and drove off, leaving me there standing on the gravel. I paused for a moment and looked around. All I heard was the singing sound of the crickets. I slowly walked to the door. Did I really want to do this? Was I really...

189 Views

Likes 0

Tuesday Night

I set at my desks a few minutes past 5 in hopes my coworkers would clear out. I did not want to wait to long, for fear of making my trainer mad. As soon as the mob got past the time clock, I rushed out to my car just as fast as I could. I was both surprised, and relieved, he was not there yet. I got in the drivers seat, started the car, and turned on the radio. The third song had just started when my driver side door jerked open. Move your ass over I’m driving. As I was...

167 Views

Likes 0

The First Time Part (one)

This is my first story and my true fantasy how i would like my first experience to be, so i hope you like it and try not to be too harsh with me i am a little sensitive. I hope the theme covers all without offending too many of you cute ladies and women or girls... Love you all and hope you enjoy. The First Time We Were Alone. As I lay you down and kiss you passionately until the faint moans try to escape your throat. My hands explore your body until I find your pert tiny breasts that attracted...

175 Views

Likes 0

Popular searches

Share
Report

Report this video here.