Another story about Simon, that signs my name [ Milker ] to other people's stories and leaves his shitty little comments
I was 9 almost 10 years old when my cousin Billy and another boy named Tommy got me to [ Ride The Pony ].
It was his friend Tommy that had brought the 6 or 7 dirty pictures over and they had me in my bedroom and were showing them to me. They were all pictures of older men getting women to suck on their huge [ Huge to me ] hard cocks and in 2 of them they even had the women sitting up on top of them, straddling them and that's what Tommy and my cousin Billy called, [ Riding The Pony ].
I don't know how long we had been in there looking at the pictures, when all at once my cousin whispered, " Wanna see my boner?" And before I could even say " No," he just reached down, pulled it out and sat there on the side of the bed and showed it to me.
It wasn't the first time that I had seen a boner on a boy because I had 3 brothers, 2 of them older than me and one of them younger. Yes, I had seen their boner's before, all 3 of them. No, I wasn't running around looking to see their boner's. But it was really hard not to see them, since my older brothers would pass me in the hallway in the morning and one if not both of them would usually have their morning pee boner's. My little brother slept in the same bedroom with me and even though he was a year younger, he would always have a little boner to, when he woke up in the morning and had to pee. But this was the first time that a boy had taken his boner out and was showing it to me.
I don't know if it was looking at the dirty pictures that had done something to me or looking at his boner that was doing it. All I know is that I was getting a strange feeling inside and somehow he seemed to know it, as he reached out and pulled my hand over to it and whispered, " Play with it " and even though I was able to turn my head away and not look at it anymore, I couldn't pull my hand away and the next thing I knew he was moaning and saying " That's it, that's it, play with it " and I did.
I don't know how long I been playing with my cousin Billy's boner, when I felt his friend Tommy trying to undo my pants and when I tried to stop him, he whispered, " Hold still, I just wanna see it " and the next thing I knew, I was letting him undo my pants and even watching as he slowly pulled them down. For whatever the reason, I was ok with letting a boy pull my pants down. But when he took ahold of my underwear and started to slide them down to, I said, " No " and he got mad at me and just jerked them all the way down and watched as my little boner popped up. Yes, I had a boner, even though it was little, it was still a boner and it was sticking straight up. I don't even remember how he finally got my pants and underwear all the way off. All I know is that one minute I was saying " No " and the next minute he had me sitting on the side of my bed with nothing on but my T-shirt.
As soon as he had my pants and underwear off, he went into the bathroom and closed the door. I thought that he was peeing and didn't think anything about it but then the door opened and there he was standing in the doorway completely naked and now his boner was sticking straight out too.
Even though he was 14 years old just like my cousin Billy, his boner was only 4 to 4 1/2 inches long and that shocked me even more because even mine was almost that big and I was only 9 almost 10.
I really didn't understand what was going on as he walked over, crawled up onto my bed, laid down and started playing with it. Not even caring that both of us were still in the room and watching him, while he did it.
I don't know how long Tommy had been laying there playing with it, when all at once my cousin Billy whispered, " Wanna Ride The Pony " and I heard myself whimpering and saying, " Nooo."
Tommy looked over at me and said,"Come on, I won't hurt you, [ Ride the Pony ]."
When I still wouldn't do it he said, " Ok, then pretend ride, ok."
I was still looking over at it when he said " Pretend Ride " and the next thing I knew, I was crawling up on top of him and holding real still, as I let him start rubbing the end of it up against my little asshole, my tiny little asshole. Not even understanding that what he was doing, was smearing his clear pre-cum all over it, wetting it, getting it ready, ready so he that could have his way with it and fuck it, as he made me [ Ride The Pony ]. One minute he was gently rubbing the tip of it up against my little asshole and the next thing I knew he was slowly trying to ease it up into me and I didn't even know it. I didn't know it because it felt just like it did when I went to the bathroom back there, when my little asshole would just open up and let something slide out and then close back down again. But this time as it had opened-up, something had slid up into it and was holding it open, not letting it close back down again and that's what my little asshole didn't understand, as it went into spasm around his warm stiff boner.
As soon as Billy saw him easing it up into me he started screaming, " That's it, Ride it, [ Ride The Pony ]." Even though it was painful and I was wondering why the women in the dirty pictures liked doing it, I soon found out why, as I started riding it up and down on it, just like they wanted me to.
I can't even describe how his warm cock felt, as it moved back and forth in me, stretching me more and more and making me whimper. But somewhere along the way all the pain went away and left me with nothing but pleasure as they got me to [ Ride The Pony ] faster and faster.
Just when it was really starting to feel good, a car pulled into the driveway and my cousin Billy grabbed ahold of me, jerked me up off of it and screamed, " Get your clothes on, get your clothes on, someone's here." And while Tommy ran into the bathroom and was getting dressed again, my cousin Billy looked over at my little butt, while I was slipping my underwear back on and whispered, " Wanna ride my pony to Simon?" And I couldn't believe what he had just said and didn't understand it at all, as I looked at him and said, " Now?"
" Nooo later, will you?"
Even I was shocked when I heard the little moan that came out of me, as I thought about what he wanted to do to me, get me to[ Ride The Pony ], his pony, so he could fuck me to, just like his friend Tommy had started to do to me. Just as I was about to answer him, my aunt came through the front door and yelled out, " Hello, anybody home."
Even though he hadn't gotten me to answer and say " Yes or No, he could still tell by my face that I was still excited after just being fucked by his friend Tommy, so he already knew what the answer was going to be.
2 weeks later after my aunt left again, he picked up the phone and called Tommy. Even though I couldn't hear everything that he was saying, I did hear him say, " Yeah, bring some more pictures " and later on in the conversation he was saying, " Oh yeah, he'll ride it alright, you should have seen his face the last time, just after you finished fucking him, it was all red and flushed just like Brenda's face had been that night when she almost got caught letting both of us fuck her to, remember?"
Less than 15 minutes later, the knock came at the door and sure enough it was Tommy and he had more of the dirty pictures with him. Neither of them said a word as they went into my bedroom, got me to follow them and once again started showing the pictures to me, trying to get me horny, so they could fuck me, as they got me to ride it, [ Ride The Pony ].
As soon as they thought that I might be getting excited from looking at them, Tommy stood-up and started taking his clothes off just like we weren't even there. When he was completely naked he crawled up onto my bed and started playing with himself.
Even though I was trying not to look at him while he was doing it, I'd still catch myself peeking over at it and comparing the size of it, to the ones that were on the men in the pictures.
He was really embarrassing me because the whole time he was laying there stroking it, he was looking right at me. I wanted to run out of the bedroom but I couldn't and somehow he knew it, as he just kept playing with it and getting me to watch him.
All of a sudden he let go of it and whispered, " Wanna [ Ride the Pony ] again?" It was almost like I couldn't catch my breath and couldn't answer him and he said it again. " Come on Simon, [ Ride the Pony ] you liked it the last time, remember?"
I don't know if I answered him or not. All I know is that right after I heard him saying that, my cousin Billy started undoing my pants and I let him. Once again being totally embarrassed as he pulled my underwear down and they saw my little boner, as it sprang up.
Tommy moaned and said, " Oh yeah, he's excited alright, look at that, " as he pointed to my little boner, making me so embarrassed about having it that I wanted to hide it.
What happened next embarrassed me even more because as soon as my cousin had taken my underwear off, he bent down over my little boner, slipped it into his open mouth and started sucking on it. I moaned, " Nooo, Nooo, what are you doing, stop it, stop it," but he wouldn't. I don't know why it embarrassed me so much, to have Tommy watching him sucking on it. I guess because it was my cousin doing it and not someone else and I didn't want Tommy to know that my cousin Billy did things like that.
If I said that it didn't feel good as I watched his head bobbing up and down on it I'd be lying because it did. I even grabbed ahold of his head a couple of times while he was doing it.
Just watching my cousin sucking on me was making Tommy even more desperate to cum as he pulled my hand over to it and made me start working it up and down slowly, as once again he said, " Come on ride it, [ Ride the Pony ], you know you want to."
When my cousin heard him saying, [ Ride The Pony ] he raised-up off of my little stiff boner and said, " Go on Simon, Ride it, ride it like you did before, remember how good it felt when you rode it."
I did remember how good it felt and before I knew it, I was crawling back up on top of Tommy and once again letting him rub the wet end of it against my little asshole. Smearing it with his wet clear pre-cum, so he could fuck it, while Billy watched him. I screamed as he grabbed ahold of my hips and pulled me down on it, driving the entire length of it up into me and holding me there, as my little asshole went into spasm. Spasm from being stretched open so fast and then slowly wrapping itself down around him.
" Aggghhhhhhhhh, Agghhh Shit, he's tight, you should feel what his little asshole's doing to me."
I don't know how long it took before he saw that I wasn't going to fight it and let go of my hips. Laying there under me and watching me, as the pain went away and my little butt started to slowly move up and down on it. Just like he wanted it to.
" Oh Fuck, Oh Fuck, Thats it ride it."
I don't even know how to describe how good it felt as it slowly moved in and out of me, stretching my little asshole and stretching my warm soft rectum, to the limit.
" Oh yeah, Fuck yeah, ride it Simon, [ Ride The Pony ]." " That's it, that's it faster, ride it faster." " Oh shit yesss." "Agghhhhhhhhhh...Ohhh shit Noooooo, I can't hold it, I can't hold it anymore, here it comes Simon, here it comes, [ Ride the Pony ] " Squirt...Agghhhhh, Squirt...Agghhhh, Squirt...Squirt...Agghhhhhh...Squirt." " Oh Fuckkkkkk yesss," squirt.
Every time his warm hard cock would jerk and squirt up inside of me again, my little ass would jerk and then quiver, before settling back down on it. Leaving no doubt whatsoever in my cousin's mind, that his friend Tommy was squirting his pearly white cum up into me again and again, as he got me to ride it, [ Ride The Pony ].
I was still straddling his friend Tommy, when my cousin Billy crawled up onto the other side of the bed and while holding his boner he looked at me and whispered, " Wanna ride mine to, when you get through riding his?"
Just looking at the size of it, told me that it was going to hurt me, more than Tommy's had hurt me. But something had changed inside of me while Tommy was fucking and stretching me back there and I'm embarrassed to admit that I wanted to feel his swollen cock as it stretched me back there to.
The shame I felt, as my cousin Billy watched me slowly raising up off of Tommy's now simi-hard boner and watched as it dropped back down and laid across his belly, was unreal.
I couldn't even look at him, as I crawled over and straddled him, waiting for him to do me, like his friend Tommy had just done. I could feel him moving the tip of his boner all around, circling my little asshole with the tip of it, teasing me, trying to get me to [ Want It ] and it worked because [I did ]. All at once he found it and before I could even finish saying, " Please don't hurt me " he was already working it up into me and since is was thicker than Tommy's it was hurting me and I started screaming and begging him not to do me with it. Even though I was screaming and crying he wouldn't stop and that's when I found out just how really mean boys can get when they want to fuck something and are about to be denied it. When he couldn't get it all the way into me, he grabbed ahold of my hips, pulled me down onto it and rammed the rest of it up into me as hard as he could. " I screamed and screamed as he worked my little hips up and down on it, working it up into me deeper and deeper until finally it was all the way in and he was saying, " I'm in, I'm in, don't cry Simon, the pain will go away and it will feel good again, remember."
I don't know how long he held me down on it like that before he heard the strange little moan come out of me and knew that my little asshole had finally given-up and was going to relax and let him fuck it.
" Ohhh Yeah that's it, that's it relax, you want it now, don't ya?"
" Uh huh.....uh huh."
" It's all yours, [ Ride the Pony ] " and the next thing I knew, I was riding it and not caring what either one of them thought of me, as they watched me doing it.
It didn't take long for my little asshole to open up, relax and let him start fucking me as hard and as long as he wanted to.
I don't know how long he had been fucking me when all at once he stopped and started screaming, " Get up, get up, get down on the floor, I wanna do you down there, I wanna do you [ Dogstyle ].
I couldn't believe what he was saying to me. How had it gone from them simply wanting me to [ Ride The Pony ], to where he wanted to fuck me, yes, fuck me, like I was some kind of animal?" Yes, I knew that they were [ Fucking me ] when they were getting me to [ Ride The Pony ] but somehow my mind wasn't looking at it that way and now it had to, because now he wanted me to get down on the floor and let him mount me like a dog, a dog mounting another dog in the bushes.
The shame or embarrassment that I felt as I got down on the floor and let him mount me, like he wanted to, was unreal. But the need to feel his warm cock sliding back and forth inside of me again had taken over and there was no way that it was going to be denied, so I was totally at his mercy and he knew it.
While my cousin Billy had me down on my bedroom floor and was fucking me [ Dogstyle ] his friend Tommy went into the bathroom, peed and came back out. But instead of walking back over and sitting back down on the bed, he walked over to where Billy was fucking me and stood right in front of me. Showing me his now limp cock and trying to get me to suck on it.
I don't know what happened. One minute I was looking at it while Billy was fucking me, saying, " Nooo " and the next thing I knew he was holding my head and moaning, " That's it, That's it Simon, suck it " and I did.
I guess seeing Tommy getting me to suck on his dick after he had just fucked me with it was to much for my cousin Billy. Because all at once he pulled back on my hips and drove his warm boner and the way up into me and held me there on it, as he moaned real loud, " Agghhhhhhhh " and I felt it jerk, Once..." Agghhhhhh," Twice..." Agghhhhhh " Three times..." Aggghhhhhhhhh " and I knew that he was leaving his warm white cum up inside of me, just like his friend Tommy had done, 5 or 10 minutes earlier.
Tommy never did cum again and I was glad because I don't know if my mind could have handled it or not.
As soon as they were finished with me and had left, the shame of what I had let them do to me set in and ruined it all for me. It was like letting them get me to [ Ride The Pony ] was alright but to get down on my hands and knees like that and let them fuck me, my mind couldn't handle and I could never let them do me like that again, when they once again they would get me to [ Ride The Pony ].