I can remember exactly when it first started even though I am now much older.
My brother Mike was a newly minted teenager, full of life and adventurous. I was so much younger and sort of looked up to him. We lived in a small house because my Mom was on her own and worked nights a lot. Two bedrooms, one for her and one for us brothers. We slept in the same bed.
We had some sitters and housekeepers off and on but my Mom always fired them if she thought they were taking advantage, so even at such a young age I was alone most evenings. Mike was supposed to stay in with me but often went out with his friends who were already chasing girls. Mom usually got home about 2 am, long after we were asleep. I thought if I told her Mike left me alone so much it might be worse for me so told her nothing. I usually saw Mom when I went home for lunch and again after school before she went to work. She was doing the best she could and didn’t have much life herself.

There were times when Mike and me fooled around with our cocks out. That started when he was eleven, the first year we fooled around. Masturbating each other. Mike had a very large cock and he made me jack it often at night until I made him cum. It only took a few strokes with my hand. I kind of liked when it got harder after a while and he was already able to emit some goo. He was mature for his age and most people thought I was too, even though I was six years younger than him.

And at thirteen, Mike was kind of mature and sort of making his own way and would stay out at night with his friends talking to girls. I got into the habit of either being asleep when Mike returned or pretending to be if he got home late. He would usually just crawl into bed and turn the light off, but other times he would be horny and want to make me masturbate him. If I pretended to sleep he would just whack himself off and make the bed jiggle and I never responded.
Mike could be mean when he wanted to be, and beat me up sometimes, but he was afraid I would tell Mom he went out each night so didn’t do that anymore.

I always just had my back turned to him so he couldn’t see if I was awake or not. One night he came home and tucked in behind me. I knew he wanted me to jack him off as I assumed he was excited from chasing girls but having no success with them. He moved very close and whispered to see if I was awake, so I kept my eyes tightly closed and pretended sleep. He even took my hand and placed around his swollen cock but I didn’t feel like it so did nothing. He let it go but I had his precum on my hand. It was sort of slippery like olive oil. I hoped he would give up with my back to him.
That’s when he moved closer behind me and pressed his cock between my legs at my bum crack over my pajamas. His cock was warm and seemed heavy. I really thought he would just go to sleep but Mike must have been feeling real sexy that night.

He pushed his cock harder under my rear and whispered my name a little louder. It felt a little odd but after a while he reached in front of me and undid the knot to my drawstring pajama bottoms. Pulling them down very slowly to expose my bare bum. It felt a little funny being part naked. Now it seemed now like he wanted me to stay sleeping. I was glad he didn’t touch my dink or he might have known I was awake. It was kind of a weird fluttery feeling in my stomach.
Now Mike moved his hard cock between my bare legs, letting it press under there, moved it forth and back for a bit and then pushed into my crack. It felt warm against my skin.
And he began rubbing his finger at my bumhole and I realized he was putting his precum there, because it was so slippery.
He let his forefinger slip into me and pushed it in a bit. It was uncomfortable at first but I thought he would give up if I didn’t respond, if I woke up he’d demand that I make him cum off, so I just laid still. He circled his finger around my moist asshole steadily until it began to feel real nice and he started to push it in and out too.

Mike was determined and seemed to rub more of his juice there until he moved upward and I felt his wet cockhead against my hole and thought he would never try to get that big thing inside my bum. It was already 6 inches long at thirteen. I was wrong.
He pressed his cock slowly against me moving it up and down over my now slippery hole until I could feel my ass expanding. Now he was being gentle because he was afraid I might stir and he’d have to stop. He just pressured a little at a time, using his finger and his warm hard cock. His movements were slow and careful. When I first felt it go in it sort of hurt and felt good at the same time but I didn’t know what to do, and now didn’t want him to stop either. He even held his hands on my hips so I wouldn’t slide away and pulled apart my bum cheeks with his thumbs. Now I had no idea how to respond and still just laid there quietly. He pressed his cock at my hole and pushed but it wouldn’t go much inside me. I think his cock had expanded.
Mike got up and went into the bathroom and I thought he was whacking off in there and would just go to sleep when he returned. Boy, was I ever wrong.

He slid in behind me again. Moved close. He was very warm and his cock was now harder than ever. He pressed the knob close again and this time rubbed something into my asshole that was slippery. I closed my eyes tighter and now was anticipating pain and wondered if I should wake up and try to stop him. If I did he might get angry which would be bad for me. But had to admit I was now enjoying that tingly feeling in my rear.

He said, “Terry”, once more, still wondering if I would wake up, when I just lay there he pressed a finger into me then another I think, moving them around in there.
Then Mike pushed his hot cock to my bum, it kind of scared me at first, but this time ever so slowly worked it into me a half inch at a time until I knew his cock-head was fully inside my asshole. My stomach had a fluttering nice feeling inside. Now I had my eyes wide open in the darkness, it was a weird feeling with that large thing slowly going inside me! It was odd but I could feel his cock sort of pulsing. I could also feel Mike’s tension as he tried to be stealthy yet insistent. He would lie very still a moment, then move it inside me a bit at a time. I could actually feel his pulse through his cock in my bum! I was getting a little hard-on myself and hoped he wouldn’t know it. We were both keeping a secret, even from each other. I wondered who had taught him to do this?

I laid there in silence as Mike pushed against me very slowly until he slid more of his young cock into me, but still not even half of it. It was beginning to feel sexy, and I wondered what the feeling was like for him I was not sure if it would have gone in better if we weren’t both lying on our sides. I know it was six inches because he measured it one time. He seemed to slow a minute and then I could feel his cock actually begin sliding forth and back now inside of me, rubbing everywhere in there and at the entrance. I was being fucked!

I was unsure what to do as but my heart was pumping so hard I thought Mike might hear it. I had no idea that a thirteen year old could fuck a seven year old, even brothers. And I had no idea it could feel like this. He pushed it in farther and almost out in steady long motions and it began to feel really like I was stuffed with a cock. I wanted to jack myself off but couldn’t show I was awake or Mike might stop. My ass was now expanded enough so it didn’t hurt at all. He was so hard and pulsating. His hands tightened on my hips and he jiggled forth and back quickly in short motions until he let out some quiet groans and a long sigh, his cock throbbed inside me for a few more times and I thought he must be cumming in there. His body jerked at the same time.
Finally he slipped out of me and turned over to sleep. Leaving me wide awake in the darkness with his cum inside me. It was strange but I was sort of thrilled and excited.

Next morning I said nothing and neither did Mike except to ask if I slept well. Odd, but he seemed a little more attentive to me, which was unusual. I couldn’t think of anything to say and didn’t want Mike to know I had been awake when he fucked me in my bum. It seemed so strange to say that. I had been fucked almost like a girl and the idea made my stomach flutter again. My bum felt a little slippery that morning but okay too, not really sore just a little sensitive. Mike often talked about wanting to fuck girls but the idea seemed very distant to me. Yet he being thirteen it was natural for him. He had been making me masturbate him for years now and when he did me, which was rarely, I came but spurted nothing. Just had a nice little shudder. I hoped they might get as strong as Mike’s was last night.

After school that day I even looked at my bum in the mirror to see if it was different but noticed nothing. Mom left for work after making us early dinner. Mike went out right after she left so I was alone again. Just watched TV until my eyes closed and I went to bed.
I lay there thinking and even had a strange new tingly feeling in my stomach. I know now that it was lust. I was almost asleep when I heard Mike coming up the back stairs. I thought he might be too embarrassed by what he did last night and go right to sleep. I didn’t really think he might try those secret actions again. But he must have been thinking about it all day too.

I closed my eyes and snuggled into my pillow. Pretending sleep. He spent some time in the bathroom before coming to bed. He must have been wondering if he could do the same thing again as he turned out most of the lights, only one burned in the kitchen. I think he wanted me sound asleep as it seemed like an hour before he moved behind me and asked if I was awake. This time in a louder voice. I just stayed quiet and breathed as if I was soundly sleeping. He even nudged me a little like he was trying to wake me but I knew he wasn’t really.

After a few waiting moments he slipped my pajama bottoms down to my knees.
I could hear him undoing a lid and now I guess it was the Vaseline jar that was always in the bathroom. He gently rubbed some on my ass-hole again before pressing his hard cock against it. Being very stealthy. His cock was so warm. And sort of hard and soft at the same time. He moved his cock head forth and back in the slippery Vaseline until he made my hole more receptive and then pushed it slowly in. I was glad he was doing it so gently so I could remain asleep but awake. But now it was pleasuring for me too.

This was so strange. My brother had a large cock and I knew I must have a tiny bumhole, but he was able to slide it inside me again, this time a little more easily. I could feel my own heart pounding now as he actually began stroking it in and out of me, holding his hands on my hips. I was just like a girl being fucked and that idea seemed exciting. My little prick was standing straight out! Now it was feeling really nice as he gripped my upper leg by the thigh and lifted it upward a little and continued fucking me deeply. This time he pressed more cock into me, until I could feel his tummy right against my back. He would pause a moment with it deep inside, moving only in little jerks, before he fucked me a little faster, it was making my head spin because it now felt really good in there. It seemed so tense at that moment. Then he groaned aloud when he came and I could really feel the spurts of cum from his cock and his thrusts were harder and I knew he had his cock fully inside of me. This time when his body jerked I shuddered too and had that really great feeling myself, an orgasm from being fucked! I didn’t know that would happen without me tickling my cock!

Somehow I was now thrilled at him having an orgasm from fucking me. It made me feel really sexy. and it showed he really liked it or he wouldn’t do it twice. I had never dreamed someone would like sticking a cock into me there. Mike drifted off to sleep with out even pulling my pajamas up again.

He had no reaction about it the next morning either. And I pretended I knew nothing. Although he did remark that he made noise last night and didn’t even wake me. I made no comment. I think he was fishing to see if I was so sound asleep that I could really be fucked without waking up! And at school I would whack off in the boys toilet thinking about it and even nearly got caught by another grade two teacher one time who stood just outside my stall door and I thought he was peeking in through the crack. But that only made me wonder what a man’s big prick would be like? Could a man fuck a seven year old boy like me? I thought about that all day and went back into the can to finish jacking off again later!

Over the next few months, my brother fucked me almost every night. I even made sure my bum hole was clean because now I didn’t want him to get a stink back there. And he was a lot nicer, doing some of my chores as well as his own.
One night he did it to me and I fell asleep right after, but woke sometime during the night to feel him pushing it in there again! Sometimes I would really be asleep when Mike came home, but once he slipped into bed so close behind me, I always woke up. We never talked about it at all and he never knew I knew he was fucking me. I jacked off after school in the boys bathroom at school now every day, recalling the previous evening. I sort of wondered what would happen if that teacher caught me doing it. Would a grown man want to fuck me too? And I wondered whether it was okay for me to be enjoying it like I was. Mike was out most nights if Mom worked and told me he had met some older guys and was having fun with them.

But he was full of sex and it was usually the same routine, Mike would come in late, I would lie there pretending sleep until he started to fuck me. And things were changing slightly. Once he started fucking me I would respond by pushing back into him, allowing his cock to penetrate me deeply. I couldn’t help doing it, I was enjoying it so much. My stomach fluttered whenever he started pushing his hard cock into me. And when he came I often trembled with my own little orgasm but he never knew because I didn’t spurt any cum yet.

The first time I pushed back onto his cock he stopped and waited, and said in a low voice, “Terry?” But I just kept quietly breathing until he resumed. After a few more times, I was able to respond to his thrusts without him even thinking I was awake! It even became so pleasurable to me that once his cock was there at my entrance, I would thrill at the foreplay until he put it in, jerking with my own little fuck back motions. I could tell that my movements excited him after he decided that I was doing it totally asleep and oblivious to him fucking me! I had become his secret little sleeping fuck boy!

Once Mike turned me toward him a little, so I was almost lying on my back. He knelt over me and moved upward until his cock was now at my mouth. Now I wasn’t sure at all what would happen if he put it in there. He tried but it was too hard to push in stealthily like fucking so he gave it up after rubbing it over my lips a few times. I wasn’t sure what to do even and only let my tongue out a little to feel his cock with it. However I did get the taste of his precum on my mouth and that seemed strangely exciting too. I hoped he might find a way to try it again.

One night when I heard Mike coming up the stairs I thought I heard more footsteps. Mike was very quiet in the kitchen. I lay waiting in bed, turned away from the door, on my side with my knees up, and my pajamas very loose. Mike came into the bedroom a couple of times to be sure I was sleeping soundly. I could sense the light change when he stood in the doorway. But now I thought I heard whispering in the kitchen.
It occurred to me that my brother might have brought a girl home to play with. But he finally slipped between the covers behind me and started playing with my asshole. Rubbing some new lotion into it that had a pleasant smell.

I sensed something was different but only stayed in my usual position with my asshole so available and now anticipating a sexy fuck.
Mike pressured his hard cock into my waiting ass. I relaxed as he stroked slowly and gently. He went on for a few minutes but didn’t cum. Slipped it out of me and went out of the bedroom. After a few seconds he slipped in behind me again and felt for my bum. Moved closer and used his finger for a moment. It made me do little jerks before he started to guide his cock into me again.
It felt different right away, and I wondered for a moment until I understood, that it was not Mike behind me, but someone else with a bigger cock. His breathing was different and he seemed heavier than Mike. My heart pounded with excitement of not knowing who it was but anticipating what was going to happen! Mike was going to share me with his friends and that sent an electric thrill through me.

I felt the strange cock head pressuring to go inside me and was helpless to react except to push back onto it. It felt so good and sexy but bigger and longer than Mike’s cock.
The stranger backed off a moment until I could feel something real soft and slithery at my bum hole. It was his wet tongue, circling around back there. He stuck it into my rear and twirled it around and it made me feel really nice. His lips were kissing my hole with his tongue licking inside. But he stopped and shifted back up behind me. I was feeling real odd at that moment, sort of had my head spinning at that feeling. He pressed close again.
This person’s erection seemed filled with strength and tension. The cock was thicker too. As the guy began slowly entering me I realized I wasn’t able to react any other way than to enjoy the fuck like always. If I awoke, Mike might know I was not asleep all those weeks of him fucking me.

And somehow, the stranger behind me was so sexy. He stroked my sides and legs, even felt my nipples and my own dick which hardened right away with his fingers. Kissed me wetly on my shoulders. He started fucking me with steady pushes and I shuddered and trembled with each long stroke. It went way in and rubbed everything as it did, then when he pulled back I squeezed him with my insides. He held strong warm hands on my hips. I heard him whisper, “Jeezuz.” as he pushed way deep into me.
Now the doorway darkened and Mike whispered, “See Jack? I told you.”
Jack kept sliding into me and holding there. I could feel his cock throbbing inside me, filled me with it. He whispered back, “Gawd, Mike, this is fantastic! He wont wake up?”
“No, I fucked him three times one night. He never wakes up.”
“Jeeze Mike, your little brother is a beautiful fuck!”
I could feel Jack quicken and even felt his cock harden and swell more. His breathing became jerky. It throbbed and I tightened my inside bum muscles. And now couldn’t stop jerking forth and back a little when it went in so deep.
Jack said, “I’m going to cum in him.” Holding it in there as he spurted again and again inside me, pulling me by my hips hard onto him until he shivered and groaned aloud. I was shaking myself with my orgasm too but he wouldn’t have noticed.
Wow, I had made another guy cum from fucking me! A real man.

Jack laid there panting, said, “Jeezuz Mike, it was like he was milking my cock! That was fantastic!”
Jack pulled away and Mike slid into bed right after, sliding his cock into the slippery hole just used. He fucked me quicker than usual and was then gone. Left me still vibrating with the new experience of being fucked twice by two different guys.
So I was still wide awake and trembling from the thrill of what had just happened. I listened hard, heard more whispering in the kitchen, sat up and could hear as Jack thanked Mike for sharing his boy-fuck. He asked if I liked being sucked off and Mike said he didn’t know. Jack said he would do it if I ever woke up. So I would have something to like and not be mad. Or even if I didn’t wake up. So he could get me trained to do it to him too. Jack told Mike, “And if we put him on his stomach with pillows under his belly, his ass will be up there just right for great fucking. It’s a better position.”
That idea sent a thrill through me. The thought of the guys using me for their pleasure.

Jack said there were a lot more buddies he knew who would love the chance to fuck someone so young. And said he would bring his friend tomorrow night. Same deal. My heart quickened with that idea. Was this the start of some sort of youthful sexual career for me? I was totally excited that I could have made two guys cum like that, and judging from Jack’s voice, he was a man not a teen like Mike. I wondered how many grown men would really like fucking me? Like to use me as their private little fuck toy.
I tickled my dink and had a really nice shudder through me.

Whatever was going to happen, the idea was making my stomach tingle like crazy. I fell asleep with the thought of sucking on a warm hard cock but wasn’t sure about making it spurt into my mouth, and wondered if Mike would ask me to try it soon. I had no idea what to do.
I awoke later with Mike fucking me again and knew that he was excited all over again by what had happened with Jack, sometime I was going to have to stay awake for the fun, for now I felt that this was a great sexy secret between us that neither wanted to expose. Except I wanted to tell Mike that I would not awake when it was happening because I knew he was worrying about it now. Especially since he started to share me with his friends. Whenever he made reference to me sleeping so soundly I always say I don’t hear anything at all.
My mind even wandered sometimes to that man teacher at school and I wondered how to get him to show me his cock? This was way too good for me not to try for more men for fun times.
I wondered what Jack’s buddy would be like?

End of Part 1