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Introduction:

Another story about Simon, that signs my name [ Milker ] to other people's stories and leaves his little shitty comments
It was the 3rd time that the same man had picked me up hitchhiking, that it happened.

I really didn't want to get into the car with him but I had been standing there for quite awhile and I was horny. That's why I was hitchhiking.

Yes, that's right, I was horny and trying to once again get my dick sucked, to be honest about it.

I really didn't care if it was a girl or a boy, a man or a woman that did it, I had been sucked by all of them before and to me, there really wasn't much difference on how their mouth's felt wrapped around my hard stiff boner. I guess that that sounds like I looked down on the people that sucked on me but I didn't. Shit, I had been getting it sucked on by girls since [ Windy ] the little girl nextdoor wanted to suck on it and I was only 13 and she was only 11. I never did ask her why she liked to do it, she just wanted to, so I'd let her.

Now here I was years later, still trying to get someone to suck on it. But even I knew by then, that it was usually a man that picked me up hitchhiking, so looking forward to having a girl pick me up, was pretty much out of the question.

Like I said earlier, this man had picked me up before and each time he did, he told me that he was a masseur and offered to give me a massage for free, at his house. But something about having a man rubbing and squeezing on my body didn't sound all that good to me, so I never went home with him. But this time I was so horny that he was able to talk me into it and the next thing I knew, he had me standing in the middle of his living room, taking my clothes off, leaving nothing on but my underwear.

I felt weird or strange standing there in front of a man, with nothing on but my underwear. But he was comfortable with it and tried to get me to relax as he brought his massage mat out and laid it down on the floor, telling me to lay down on it on my stomach and I did.

I don't know what kind of oils he was using but I do know that they were bringing the warmth up from my skin and I liked the way it felt as he massaged my back first and then worked his way down one leg and then up the other. Just brushing my little ball sac, that was still inside of my underwear with the edge of his hand, just to see what I would do, as he worked his way back up to the top on first one leg and then the other.

When he had finished with my legs, he went back up to my back and started massaging slowly, working both hands closer and closer, to the top of my underwear. Eventually bending over and whispering, " I could do it alot better Simon, if you'ld let me pull these down, if only a little, at least they'ed be out of the way." And without waiting to see if I'd let him, he started to slowly slide them down, until they were at the bottom of my butt cheeks and that's when he lost it and moaned, " Oh Simon, you have a nice ass, a really nice big ass." And before I could recover from what he had just said, he was pouring more hot oil down onto it, massaging it and I let him. I could feel his big hands gently spreading my cheeks and then felt his well oiled fingertip massaging against my little asshole, coaxing it to open and let him slip his oiled finger up into me. But that's not what he wanted from me as he coaxed me into rolling over. Rolling me over onto my back, exposing my little boner to him and he knew that I was his now, if he wanted me.

I watched as he raised the little hot oil bottle over it and the little stream of oil spilled out over the lip and dropped straight down, burning and stinging my little boner from the warmth of it. When he heard me scream and then the moan that came out of me, he raised it back up, so the oil wouldn't go over the edge anymore. Just when I thought it was over he poured even more of the hot oil down onto it. Burning it once again and bringing another little moan out of me. A little moan that told him that for whatever the reason I had liked it and that's when he said, " Don't move Simon, I have to get more oil. "

I couldn't believe it as I laid there naked on a man's livingroom floor and waited for a stranger to come back into the room and pour hot oil onto me. Onto my boner,my now even harder boner that was getting stiffer and stiffer, from the hot oil that he was pouring onto it. But for some reason I couldn't get up and leave, It was like I had to let him do it, I don't know why.

When he finally came back into the livingroom with the hot oil, I was still laying there with my legs spread, just like he knew I would be, the only difference being that this time I had my eyes closed. I think that I was ashamed of what I was doing or letting a man do to me and that's why I had them closed. I don't know.

It wasn't until he had stepped over me again and was straddling me, making me wait a long time before pouring it onto me, that I opened them back up and screamed, " Nooo." He was standing over me naked and he had a boner. I was shocked because he was naked and I was even more shocked that he had a boner, mainly because he was 50 or 60 years old and I didn't know that men that old could still get a boner, especially one that was that big, it was 8 or nine inches long, maybe even longer. That's how naive I really was, I didn't know that old men, as old as he was could still get it up like that.

When I started screaming about him being naked, he kept telling me to shut-up and that he'd only taken his clothes off in the first place to keep them from getting any of the oil on them. Before I knew it, he was pouring another stream of hot oil onto my boner, standing there, watching and listening to me squirm and scream as he dribbled it back and forth across it and then slowly work the stream of hot oil down and onto my little ball sac, " AGGHHHHH NOOOOOOOOOOOOO."

" Rollover Simon ."

" No more, no more, please no more, it hurrrrts."

" Shut-up and rollover."

No sooner was I on my stomach, than he started dribbling the hot oil down and along my back. Working his way down and stopping were the hot oil was dripping just above my butt cheeks.

As I was laying there thinking that that was as low as he was going to go, I heard him say, " Spread um Simon," in the strangest sounding voice.

" Nooo."

" Spread um."

I had the weirdest feeling as I reached back and slowly started pulling my cheeks apart, knowing that he looking at my little rosebud of an asshole and was about to pour hot oil down onto it. Just as I was going to tell him " No, I don't want to do it anymore " he poured the first of the hot oil down onto it and I screamed, " NOOO, NOOO, STOP STOP IT'S TO HOT, WAY TO HOT." But he just kept pouring and watched me squirming and screaming underneath him, until all of my screams eventually turned into moans and he knew he had me. " Keep um apart Simon , there's only a little of the oil left, I promise." And once again I felt nothing but shame, as I laid there holding my butt cheeks apart and letting a naked man pour hot oil down onto my little asshole and felt it puckering up for him, just like he wanted it to.

I can't even describe the feelings that were going through me while he was doing it. One minute it was burning and stinging and the next minute there was a warmth and a weird pleasure and my mind was going back and forth from the pain and then back to the pleasure..

When all of the oil was on me, he set the little container down and squatted down on me. Sitting back on my legs gently as he started rubbing the warm sweet oil first into my back and then working his way down and kneading it into my wide butt cheeks.

If he was only kneading it into them, it would have been alright. But he was doing more than just kneading them, he was brushing his fingertips inbetween them and lightly touching my little asshole hole with the edge of his finger, causing it to pucker up and I lost control of my ass. The next thing I knew he was slowly easing his fingertip up into me, holding me down on his livingroom floor and finger fucking me,not caring whether I wanted him to or not

Being a boy and being finger fucked in the ass by a man was hard enough for my mind to handle.
But the real embarrassment came when he felt my little asshole clamp down, closing tightly around his finger, squeeze on it again and again, like it was trying to milk it, and then slowly release it only to start doing it all over again, causing him to moan, " OH YEAH,FUCK YEAH, YOU LIKE THAT DON'T YOU SIMON?"

All I wanted when I went out that night was to cum and just when I thought that his finger was going to do it, he slowly eased it back out of me,leaving my little asshole throbbing and wondering what had just happened to it and laid down on top of me. Just as I started to say, " What are you doing," I felt his warm boner sliding back and forth inbetween my butt cheeks and rubbing against my little asshole. across my little asshole. He was dry fucking me,just like we used to do girls, right there on the livingroom floor.

If I said that it didn't feel good, feeling his boner sliding back and forth across my little asshole, I'd be lying because it did. But once again I started feeling guilty about letting an old man use me sexually [ even though he wasn't really doing anything to me] and I started whimpering and begging him to get off of me but he wouldn't. I could hear his breathing starting to change and that's when I felt it. I felt him putting the end of it against my little asshole and before I could even say " Nooo" he pushed. Pushed so hard that the end of it tore my little asshole as it went up into it. I screamed and screamed but nothing came out. I was screaming that it hurts and begging him to take it out of me, in my own mind but nothing was coming out. Since I wasn't screaming he thought that I liked it and pushed another inch or 2 up into me, holding me there, waiting for my little asshole and warm soft rectum to adjust to the size of it. I was laying there in shock because an old man was holding me down on the livingroom floor and pushing his warm boner up into me and I couldn't understand, why.

Finally my screams came out, " NOOO, NOOO, IT HURRRRRRRRRTS, IT HURRRRTS, I'M NOT THAT WAY, TAKE IT OUT, TAKE IT OUT, PLEASE TAKE IT OUT." " AGGHHHHHHHHHHH."

But the more I screamed and begged him to stop, the more he thought that I liked it and pushed even more of it up into me. When he finally had enough of it up inside of me to fuck me with it he did. Slow at first but getting faster and faster as his warm hard boner stretched my little asshole and warm soft rectum forever.

Feeling a man's boner working back and forth up inside of you is a feeling that can't be explained because eventually the pain turns into some kind of pleasure and you feel guilty, especially when you feel your ass starting to respond to him and you don't know why because your a boy and he's a man and that's not how it's supposed to be. I found this out while he was still fucking me and inbetween his grunts and groans, he was saying, " Can you take more Simon, can you take more " and I was shocked when I heard myself whimpering and saying, " Uh huh uh huh deeper, deeper, do me deeper."

I don't know if he ever got the full 8 or 9 inches all the way up into me or not but I do know that before it was all over I could feel his heavy ball sac slapping against my little one again and again.

All at once he drove it as far up into my ass as he could and held it there, just as I started screaming, " Don't cum in meee, Don't cum in meee, Pleeeeease don't cum in meee " but that's when I felt it start jerking way up inside of me. ONCE...SQUIRT and he moaned " Agghhh ", TWICE...SQUIRT and once again he moaned " Agghhh " and the next think I knew my wide ass started bucking and jerking underneath him and I was moaning just like he had done. The whole time that it was bucking and jerking underneath him, he was riding it and saying, " That's it, that's it, cum baby, cum." and I did. He rode me the whole time I was cuming. I don't know if he came anymore or not. All I know is that I had the weirdest feeling as I felt his now limp cock sliding slowly back out of me, felt him get up and go into the bathroom.

I don't know how long I laid there with my little asshole throbbing from what just happened to it, before I was able to get up, put my clothes on and sneak out the door. Sneak out the front door like some kind of animal, some kind of animal that had just done something wrong and not understanding it at all.

The shame I felt as I made my way home, was unreal. I could feel his warm cum slowly oozing back out of my now swollen asshole, soaking thru my underwear and running down along the inside of my thighs and I felt awful. The shame was coming from the fact that somehow I just knew, that everyone in the car's that drove past me, somehow knew that I had just been had. Just been had by a man that coaxed me into taking it [ Taking It Up The Ass ] and I couldn't deny it.

If I said that it stopped there I'd be lying because it didn't. It was 5 or 6 weeks later and I was drinking and the next thing I knew and I do mean the very next thing I knew, I was standing at his front door in the middle of the night knocking on it. Neither of us said a word as he opened the door and saw that it was me. He just let me in, watching the movement of my big ass as I went into his livingroom and started stripping my clothes off. He knew why I was there and what I [ Needed ] as once again he went into the kitchen, got the oil down, started heating it up, heating it up even hotter than the last time, to see if I could take it and I did. Before the night was over he had burned my little asshole again and again with his hot oil and fucked me with his long hard cock 3 more times, for a total of about an hour, before he would let me leave again.

Before it was all over, almost 7 years later, I had not only let this old man fuck me more times than I can remember but I had also let 2 of his close friends fuck me to and both of them were in their 70's.
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