Blog : The Sitter

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9/15/2023 6:53 pm

The Sitter

When I was young my parents paid a girl to sit but by the time I was 12 they just had a retired neighbor, named George, sit when they went out of town. George was a big fat man in his early sixties who was real cool, letting me take my girlfriend up to my bedroom. Amy was only 11, but we both were very horny and loved to fool around, make out, and play with each others bodies. I remember her pussy was always soaking wet by the time I went to finger her, and although she squirmed and moaned with pleasure, she would never let me fuck her.

I would close my bedroom door but I had a jack and jill bathroom and I would leave that door ajar. George stayed in the bedroom on the other side and it always turned me on to think he was watching me and Amy fool around. Amy was a tiny thing but chubby with very soft and fair skin, almost pale. Once after using my bathroom she came back to my bed and whispered that Georges side of the door was open, but she didn't close our side, and she was kissing all over me, and so we kept fooling around and I assumed she didn't really mind if George was watching.

Amy was a big tease, and after a while I was sure she liked being watched, which turned me on even more, but she still wouldn't let me fuck her. At that age we didn't go down on each other so basically we just kissed and fondled each other. After she would leave, I was so horny I would go back to my bedroom and jack off while laying on my bed, and I would sometimes hear George in the bathroom. With the bathroom door ajar and no lights on I couldn't see George but I often heard him and knew he was sitting on the toilet in the dark watching me.

Knowing George was watching me totally turned me on and so I would strip naked and play around, humping the bed, turning over to stroke my dick, and eventually I would lay sideways on the bed and push my naked little butt off the side of the bed and reach around to play with and finger my butt hole with one hand while my other hand played with my penis. After doing that on a couple occasions, I escalated to getting on my knees, with my cute little butt facing the bathroom door, and after spitting in my fingers , reaching around to fingers my asshole while George watched and jacked off in the bathroom.

I was only 12 and maybe 120 lbs., but after plenty of spit and some time I was able to make my tight little fairly loose and sloppy, but try as I might I couldn't get George to molest my horny little body. After a while neither of us ever closed our jack and jill bathroom doors, and I often saw George naked in the bathroom and when I was in the bathroom I would see him jacking off on his bed and so I would sit on the toilet and play with my dick and watch, but we were both too scared to follow through. Then one night, when Amy's parents were out to dinner, she came over and we were fooling around with my fingers deep in her soaking wet cunt, and she looks at the clock and says something like oh shit I have to go, and she quickly got dressed and left, leaving me naked and very horny on my bed.

Knowing George was watching I simply pulled the blanket over my head, leaving the rest of my body naked and started playing with my dick and nipples, and when that didn't work I reached up and turned off the lamp, so that it was completely dark, and then lay back on the bed naked, on my side, with my cute little ass hanging off the edge, facing the bathroom, and pretended to be asleep. Soon I felt Georges big hand touch my butt cheek, and it scared me so I jumped, which made George whisper "oh sorry, should I go?", and without turning to look at him I just shook my head and said no, wiggling my ass all sexy like as I did so. As George started to fondle my ass, I reach down between my legs and played with my penis, squirming with pleasure as he spread my little cheeks and played with my butthole.

After a while he spit on his fingers and worked it in to the crack of my ass, using one thick finger work the spit in to my tight butthole. I was facing the wall and couldn't see George at all but it was a total turn on to have this fat old man fingering me with his thick finger. We both moaned with pleasure as I arched my back and pushed against his finger, making it sink all the way inside me. As George finger fucked me I felt his hard dick against me as he slapped it on my butt cheek. After a while George started to moan and breath louder and louder until he exploded all over my ass cheeks. He quickly thanked me, lol, slipped back to his room without me ever actually seeing him. I rubbed his cum all over my butt cheeks with one hand and jacked off with the other.

The next night started as a repeat of the first night, turned out the lights and getting naked on my bed but this time he slipped in to my bed, spooning me from behind. I again couldn't see him but I could feel that he was completely naked as I felt his hard dick rubbing up and down in the crack of my ass, and as he humped me slowly he reached around and played with my nipples, and putting his lips up to my ear, whispered " does that feel good?" and I nodded yes and wiggled my little ass against his hard dick until he got off in my ass cheeks. Again he thanked me which was weird but somehow a turn on, and then went back to his room.

The next time Amy was over I talked her in to letting me blindfold her with my bandana, and lay face up on my bed naked. She seemed to immediately get in to it, spreading her legs and playing with her own tits, something she had never done before, and as I fingered her wet pussy I decided to get brave and straddled he head with my knees. I didn't stick my dick in her mouth, I just lay down on to her body and let it flop in her face, but she quickly grabbed it and started to kiss it as I played with her sopping wet pussy, which was now in my face where I see it and smell it, and it wasn't long until I was licking her pussy and she was sucking my cock.

I knew George was watching from the crack in the bathroom door and so I pulled up one of her legs to give him a clear view of me fingering and licking her pussy. I turned around to finally fuck that fine wet pussy of hers but as usual she quickly put the breaks on, took off her blindfold and stopped me. This time I didn't even attempt to walk her out and just laid there naked on my bed and as I heard the front door shut I took the blindfold, put it on, and lay back on my bed, playing with my dick. Within a minute I felt Georges heavy body beside me on the bed, his fat belly pressing on my side and his hard dick on my hip, as he quickly took over the job of playing with my penis.

Soon I felt his warm mouth wrap around my dick and I was in heaven, playing with my nipples as George sucked me off. I couldn't see him with the blindfold on but I felt his big ass cheeks against my shoulder as he turned around to suck on my dick, and so I started exploring with my hand, rubbing his butt cheeks, and letting my fingers go down the crack of his ass to his nasty, sticky, smelly hole. Georges butthole was much bigger and smellier than mine, and his balls were big and saggy, all of which oddly turned me on. My hand found his hard dick and I played with that until I got off in his mouth, a first for me. He spit out my cum on to my belly and then stood on his knees and jacked off on my belly, adding his cum to it.

That was Georges last night baby sitting and it was many months before I saw him again and in the meantime Amy's family moved out of state. It was awkward at first, but we both just acted like nothing had happened, had dinner, watched some TV, and I went to bed. Taking no chances I opened the jack and jill bathroom door all the way, turned off all the lights, and then lay naked on my bed sideways, facing the wall and with my little ass facing the open door started using my spit to lube up my tight ass.

It wasn't long until I felt Georges fat naked body slide in behind me, reaching around to play with my nipples, as I reached back to play with his penis. It was still soft and to my surprise, uncut, something I had only seen in the locker room. I explored his dick with my hands and fingers, feeling the stickiness inside his tube of flesh, stroking it all the way down until his dick head popped out against my butt cheeks, and so I rubbed it all over my ass and then, as it got harder, in to my crack and down to my lubed butt hole. Then I heard him spit in to his fingers and rub it all over his dick before guiding in to me.

He gently pushed against my dirty, virgin, hole, and I reached back to help push the tip of his dick in to me. The it was just a matter of time as he grabbed my hips and forced his dick slowly in to me. Georges dick was big and it hurt like hell at first but then it was in and he just held it there whispering "shhh, it's ok" before pushing it deeper and deeper as he slowly spoon fucked me, while kissing my neck and fondling my body. The the pain had resided and my dick was hard in my hand as I jacked off, until he shot his load deep inside me.

As we lay there with his softening dick still inside me, I kept playing with my dick and George ask me questions, about my girlfriend, whether this was my time having a dick inside me, if I liked it , if I had ever sucked a dick, etc. It really turned me on talking about things with his dick still inside me, and so while I played with my dick, I squirmed on his dick, pressing back to keep it from popping out and then I felt it start to grom inside me and so I just asked "can I suck your dick?" sheepishly but he imediately chuckled and said "sure" with gusto and so, without thinking, I just lifted off his growing dick, and turned around, getting on my knees to suck his dick, but when I did my butt exploded with a loud, wet, gushing, cum fart.

I got embarrassed and said "oops, sorry" but George just moaned with pleasure and said oh, don't be sorry, that was awesome" as he started to rub all that cum over my butt cheeks, and legs, while I lowered my mouth down to his big, wet, semi hard, uncut penis. It was gross, covered in cum and nastiness, and I loved it, pulling down his foreskin and licking his dick head clean before sucking it all in to my mouth. I reached around his fat butt cheeks, pulling him in to my mouth as I let my fingers explore has dirty, nasty, butt hole. He pulled one of my legs over his face so that we were in the 69 position with me on top, and my dick in his mouth and soon I exploded inside his mouth. I collapsed with my head in his lap as my dick quivered. George grabbed his dick and quickly got off, shooting his load on to my face.


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