Boys as they get older are not enamored of teen girls as baby sitters and when even older of being babysitters themselves. But sometime chance forces new roles which can be fun now and later. This story is fiction.
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I can still remember the very first time I saw Stanley's buns. It was almost three years ago when I had just turned fifteen and I found myself baby sitting the then twelve-year-old and his little brother, Kenny, ten. I normally did not do babysitting, leaving that to the girls, but the boys' parents suddenly had to go out and could not find any of their regulars. In desperation, their mom asked my mom and I was volunteered. "It not like you have to change diapers or anything. Just make sure that don't get hurt, they eat and get to bed on time." said my mother adding "They are definitely house broken." with a chuckle. "And you'll get paid enough to get a couple of those CDs you want." That last thought convinced me and I would even get paid to watch TV or do my homework.
So at five I rang the bell. Little Kenny greeted me with a big smile. He was happy not to have a girl babysitting him. They always fussed over him and never wanted to play boy games. The three of us got instructions from their parents and I could not help to smile how the two little happy faces dimmed a bit when Dad finished up with: "… and if I get a bad report about you then you're going to get a spanking in the morning."
"Yes, father." they responded and their parents left.
We played catch for an hour and then ate. Putting stuff into microwave was easy and there weren't any dishes to clean up for everything went into the garbage. I started to watch TV with them but it quickly turned into a rough housing session which was also fun. Kenny's bed time came up and when I sent him off to shower and to bed, he did as he was told. Stanley was different. He talked about being almost thirteen and that his bedtime was too early. He was starting adolescence and needed to exert himself. I let him have a few minutes extra but then I told him that if he was not showered and in bed in ten minutes he would have OTK discussion with his dad in the morning.
Ten minutes later I had to drag him off to shower and bed. As I did so, I told him that he could discuss being almost thirteen and staying up late with his father in the morning. He showered, brushed, peed quite quickly under my watchful angry eye and without a word hopped into bed. I returned to the family room to watch TV.© YLeeCoyote
It was a quarter hour later that a meek and worried Stan came into the room. He claimed to be sorry that he been trouble and begged me not to tell his father. It did not take much questioning to learn that his mom had just moved up to the hairbrush from the wooden spoon and his dad was already talking about a belt for when he became teenager. He also admitted to having earned punishment.
"I'll be negligent if I don't tell your folks and you get away with this." I told him. His pleading eyes said it all as I shook my head. He started to return to bed and then came back.
"Dad will probably use the belt and ground me also." I could have said that he brought this on himself so I just gave him a helpless gesture. He stood silent for a full minute, thinking very hard, before he spoke. "Please, spank me and not tell Dad?"
That was a real bombshell. I was dumbfounded.
"Please, Jon, Please." with that he stepped to my side and yanked down his pj's and laid across my lap. It was a position that I was familiar with, albeit from his angle. I just couldn't resist and I grabbed his waist with my left hand and patted his little boy butt with my right.
"You seem very sure of this, Stanley." he nodded. I raised my hand and brought it down on his buns for the very first time. SPANK! I watched as my hand print formed in red. It took a couple more spanks before Stanley took notice of me in a serious way. I don't think he expected me to hit so hard. He yelled and complained just like I did when Dad spanked me although, to his credit he did not try to get away. Then he started to promise to be good and to cry. I had a feeling of power that I had never experienced before. Stanley had totally surrendered to me and was accepting a painful spanking. My cock was harder then it ever was before. That encouraged me to SPANK harder and then I felt him go limp. Just like I had done when Dad spanked me. He had enough and I stopped.
I lifted him up and held him while he cried his hard but still hairless cock poking me. When he stopped he promised to be a good boy and reminded me not to tell his parents. We shook hands and he went to bed. I jerked off to a vision of his hot cherry butt.
Thinking about that never fails to get me hard.
I babysat them a few more times until Kenny was old enough to be by himself. Stanley minded me perfectly most of the time but I spanked him a couple of times a year.
I was very surprised when Stan come visiting me a couple of months ago. He wanted help with his school work and figured that a seventeen-year-old high school senior could help a fifteen-year-old freshman. It took an hour but it became apparent that his problem was not lack of brains but lack of application. Once I got on the subject he admitted it. He was worried about what would happen when he got a poor report card. "Dad has little hesitance to use his belt – long and hard – not to mention restrictions." he volunteered.
"Then you need to buckle down and do your work." telling him the obvious.
"I need help, Jon." he said starting at the floor. "You helped me a few years ago." He paused a long time before continuing. "Will you help me, again? The same way?"
My cock stiffened at the reminder. I probably should have sent him to his father but my smaller head took control over the more rational one. I lead him over to the bed. I pulled his t-shirt out of his pants and up over his head. He cooperated with me. "This will be for real. Just a taste of what your dad will do if you don't do your work, young man."
"Yes, Sir." he said with a nod.
"Kick off your sneaks." As he did that, I pulled his belt out of his pants which I opened and pushed down. "Take them off, boy." I noticed that he had grown a lot in the last three years. He had a nice cock which even if it stopped growing would be more than adequate with a nice bush above. He was no more modest than three years ago. I sat down on the bed and pulled him across my lap. I did not bother to ask him why he was being spanked.
Spank. Spank! Spank! SPANK! SPANK!
Just like three years ago I loved seeing my hand prints show in red silhouette on his firm bubble butt. As I continued to spank hard my cock stiffened.
SPANK! SPANK! SPANK! SPANK! SPANK! SPANK! SPANK! SPANK! SPANK! SPANK! SPANK! SPANK! SPANK! SPANK! SPANK! SPANK!
His smooth butt was glowing nicely. I was rock hard.
I reached for his belt and folded it.
WHACK! WHACK! WHACK! WHACK! WHACK! WHACK!
That got his attention. Another twenty and he was sobbing. "That just an appetizer compared to what your dad will do." I wondered if he noticed my cock trying to bust through my jeans.
I pulled him up and saw that he was hard and dripping. He dropped to his knees between my legs. He did not look up as I held him. Then he leaned away and reached for my belt with his hands as he nuzzled my crotch. As he opened my pants, "I was sure you'll get hard again." I raised up so that he could pull my jeans and boxers down free my cock. He opened his mouth and started to suck it. He was not experienced but I'm sure he did his best. I had to tell him "no teeth" several times. I just leaned back and gave him his head giving me head. The ecstasy built up and I exploded into him. He took it all and let it slid down his gullet into his stomach. We were both quiet for a long time.
He spoke first. "That was great, Jon. For the last two years I been dreaming about you. When you spanked me three years ago I felt your hard-on but did not really know what it was about. Later I felt different than after a spanking from Dad. When I learnt what it was about, I couldn't stop thinking about you especially when Dad strapped me." He paused and kissed my cock. Then he licked it. "I want you to fuck me, Jon; to take my cherry." My cock jumped back to full attention. I had to confess that I had jerked off to the vision of my cock in his butt.
I got up and stripped to bed to the sheet and as I stripped told him to get on his back. I got my jerk off lube from the drawer. I rolled it on my rigid shaft and put a glob of lube on his virgin hole. I worked my finger in and played with him a while. As he relaxed, I moved up to two and then three fingers. As I wanted to see his face as I claimed him, I rolled him over onto his back and put his legs on my shoulders. He was smiling at me. I moved forward and pressed my cock against his relaxed hole and slid in slowly. As I bumped his prostate he moaned with pleasure. Soon I was completely in. I paused and then started to fuck him in earnest. I was glad that he had blown me so I did not come immediately but took a few minutes. We both had great climaxes. He made a big mess on his chest and even some of his face while I injected my semen deep up his bottom. He stayed in my arms for sometime.
© Copyright A.I.L., December 24, 2001
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Last updated: September 15, 2023