The Night Before the Morning After
Babysitting is a mixed bag for a fifteen-year-old young man. I had hung out my 'shingle' in the local supermarket and a few other places looking for work although I had sitting experience here in the past. I was back in the neighborhood after a year away while my father was on assignment abroad. I even indicated my 'specialty' – older boys of nine to twelve who tend to have great antipathy to girl babysitters who makeup the cadre of most of the available sitters. Actually, I went through that myself and, additionally, found that girls are harder to sit for than boys since they frequently think that I should be a love interest. With boys I can find mutual interests helping the time pass quickly and I can do my homework after they are in bed.
It is really amazing how much more willing they are to bathe if I say: "Well, it's time for me to give you your bath. Why don't you start the water?" Almost always they claim that they can do themselves. Even when that is not true, I let them do it. They love me for that and it saves a lot of arguments, especially since it carries over to tooth brushing and all the other stuff to get to bed. It a lot easier, even if it delays bedtime a few minutes.
One of my first clients was Mrs. Milner for her twelve-year-old son, Alvin. I had watched the lad before I had been away and Mrs. Milner was delighted I was back. She told me that he had recently seemed to have outgrown bed wetting. I was glad of that since it meant that I would not have to diaper him. Of course, that was a much simpler, cleaner and more pleasant operation than having to have change him.
* * * * * * * * * *© YLeeCoyote
Alvin remembered me and even though I had spanked him a few times – with parental permission – did not seem to harbor any grudges. After all, he only got spanked by me after repeated warnings and for good cause. When we had dinner (his choice of delivery) he boasted that he no longer wet the bed and then showed me that the wet/dry calendar record was not hanging in his room any more. I praised him for that and also told him that I was glad I would not have to diaper him as in the past. He was even more pleased than I was about that.
We watched a movie and then I told him that it was his bedtime. He insisted that it was not since he was a big boy – a young man, if you please – of twelve. I did not want to force him so I continued the discussion. He was most stubborn as well as petulant and soon passed the point that was acceptable. I grabbed him as I sat down on the couch and pulled him over my lap. A few quick spanks got his attention and he immediately settled down. I raised him up, opened his shorts and yanked them and his underpants down. Then I flipped him back over my lap and spanked him some more. I did not want to make him too upset but just to impress on him that naughty, little boys, like him, get spanked. Actually he was starting to show showing the beginnings of some pubic hair growth but I ignored that.
As soon as I released him, he stood up, glared at me and pulled up his shorts. "Next time I won't be so gentle, Alvin." I told him. "How about you just get to bed like you are supposed to?" I gently suggested.
He countered with a deal. "Let play 'tie-up' like we used to and if you can't get free I can stay up." It was a game we used to play a couple of years before and he always lost. Even if he had improved, I figured that I still could get free and if not then he would just get to bed late. There was not any school the next day so it was not really so very important.
I was very wrong as I found out to my displeasure. He went and fetched some lengths of clothes line – less than ten feet (three meters) total. I should have realized that he had learnt a lot for in the past had gotten ten times that amount of rope. I lay down and put my hands behind my back as ordered. Alvin quickly slipped loops of the rope about my wrists and then did the same to my ankles. He used the third piece of rope to tie the wrist-rope to the ankle-rope getting me into a hog tie. That latter bit was actually overkill. Unlike the huge expanses of rope he used in the past, just a yard (meter) used properly was quite sufficient. He pretended to watch a silly sitcom as I struggled to get free constantly smirking at me.
I owned up to defeat and asked him to untie me. "Not so fast, boy." he said, "Remember that you boasted you would get free and you could not. That was a LIE! Little boys who lie get spanked. You taught me that many times." I was surprised that he recalled my boast of almost two years ago. Of course, I insisted that I was not a little boy but he scoffed at that. "We will see if you're a little boy or not."
I had no idea what he meant but I was about to find out. He reached for my belt and opened it. I told him to stop and untie me but he only laughed as he continued to open my jeans. It took several yanks and pushing back and forth so he could get them down to my knees exposing my briefs. My continued protests and demands were ignored. He mocked me for a small piss stain. "You did not shake your pee-pee off. You're just a little boy." Just like with the jeans, he pulled my briefs down exposing my package. It is said that size is not that important but Alvin said he was having trouble finding my leaky pee-pee because it was EVER SO TEENY-TINY. I was blushing at that for it is on the small end of average but is not that small.
"I know how to find it," he chortled, "I'll be right back. Don't go way." A lot of good that was since if I could get away, I wouldn't have been in this predicament in the first place. When he returned, he immediately started to take some pictures. When he showed them to me several included my face and well as my junk. Next he proceeded to snip my pubes off using a small scissor. I yelled that he must stop but he only laughed. Eventually, he was done and then he had another horror in store for me. He had a washcloth and he got my pubes wet and then covered them with shaving gel. "I'll soon have you properly smooth." he said as he started with the razor. "Totally bald like a proper little boy with a little, itsy-bitsy, pee-pee should be." Again he used the camera.
He went and got a bag of crushed ice and held it to my junk. Of course, I reacted like every guys does and everything got a bit smaller. He took the bag away and took a few more pictures this time with a ruler to record my shrunken state. "Well, we can see that you're just a little hairless boy with a little, itsy-bitsy, pee-pee, right?" I denied it but he persisted. Eventually, I agreed as he squeezed my balls tightly.
"So, you're a little naughty, lying boy. What does a naughty, lying little boy need?" I did not answer so he continued reminding me of what I had taught him. "He needs a good hard SPANKING on his bare bottom." What the hell was he talking about? I demanded that he untie me immediately. Of course, he did not obey me at all. He rolled me to my side and pulled one of my sneakers off and started to spank me with it.
I howled in pain as the hard rubber-like sole of my sneaker communicated with my own soul via my bottom. I could not protect myself because I was tied. I guess that he was releasing years of pent up anger at being spanked. Being spanked, even by a boy, made me feel like a little boy and I was on the verge of tears. "Are you ready for your bath now or should I continue to spank you?" he asked sarcastically. I agreed to the bath. He untied me and led me to the tub. He got the water running and then proceeded to wash me like I was a little kid. My butt hurt enough that I remained docile long enough for this. After he dried me, he took me to his room. "See", pointing to a Spidey poster, "no more wet/dry chart." He was genuinely proud of that. "But I still got diapers here for my wetting cousin … and for you." I watched as he dug into his closet for the diaper. As he pulled the diaper from package, I could see two important things – his old teddy bear, Quinn, and his wet/dry chart. That Quinn was there was understandable but the chart he would have gotten rid unless it was kept for reuse.
I grabbed the chart. He protested but I examined it anyway. He had just made the three week dry sequence required so as not to have to wear a diaper at night. He was not the big, dry boy he was pretending to be. "You've been lying to me, Alvin Paul Milner." I snarled, "That means a spanking." I grabbed him and pulled him into position for the second time this evening.
"I'll show the pictures to everyone." he threatened. A few hard spanks, even on his shorts, had an effect. "Bath time. NOW!" He did not argue but stripped and I led him to the bath.
"Please, I can wash myself. Honest. Mom lets me." he pleaded.
"Fast and thorough, Alvin." I said and he got right to it. After he had rinsed off, I told him to stand with hands on his head. By he know that he had pushed me too far and that had better not disobey at this point. I used the same razor he had on me to shave his just sprouting pubes and peach fuzz. Then when he was dry, I had him brush his teeth and pulled him back to the bedroom. "Time for the diaper." I pushed him down on the bed on top of the diaper. Then I oiled and powdered him before taping tight the one and same diaper he had planned to use on me.
"Please. Let me pee first. I hate wearing diapers. I'll wet it unless you let me go." he was practically crying as he begged. "I'll be stuck in them for weeks now. Please, pretty please. I'm sorry I was so nasty."
I was angry at him and did not yield to him. I just tucked him into bed. I got the camera and deleted all the pictures so he would not have them to blackmail me with. In the box with Quinn I also found a couple of old books. I gave Quinn to Alvin and then sat and read to him. He could not resist and calmed down. I tried to get him to smile but he wouldn't so I started to tickle him. I tickled him a lot and, as expected, he lost control thus wetting the diaper and then started to cry.
I left him crying and got dressed. He was very unhappy because he would now be stuck in diapers for at least a month. When I returned, I explained things to him. "Alvin, all I'm going to tell your folks is that you felt that you needed a diaper tonight and Quinn as well after you were spanked for refusing to go to bed. You can forget about the pictures you took because they are all deleted. It would be a very bad idea to talk about the other things you did. I promise that you will regret it for a long if you do. So just be a good little diaper boy."
I stayed with him so that he could not take the diaper off and hide it. As it was well past his bedtime, he soon slipped off into Never Never Land. When his parents returned, I explained that he felt the need for a diaper and his teddy bear. No matter what he did, they would see the wet diaper and he would be back in them for weeks. A very appropriate punishment indeed.
The Morning After the Night Before
I woke up miserable for I was in a wet diaper. It took me a few minutes for my head to clear and to remember why I was in a diaper. Gradually, I remembered that Logan had sat me the night before and I went overboard with him so that he turned on me. My butt still felt the fire that he had spanked into it. I slipped my hand into the diaper and felt for my little bush. It was gone. That Logan had shaved me was not just a nightmare but was horrid reality.
I reviewed what Logan and I had done. It had been so wonderful when I had gotten him tied up and spanked and shaved him and even took pictures of his boyish wiener. If only I had stopped then and just went to bed after showering like he told me to rather than trying to turn him into a diaper wearing baby I would not be here in a wet diaper with my teddy bear like a baby. I guess that I was pretty stupid thinking that I could do anything to Logan like I was in charge.
He said that he would just tell Mom that I got the diaper by myself and nothing else. Well, maybe he did not even tell that much. I thought that if I get up and shower, then maybe Mom won't even know. I moved my ass and started to get up but just then Mom came in. She was all sweetness except that she insisted on checking my diaper which is soaking. "I'm sorry, Alvin," she said, "but you better put up your wet/dry chart after you shower and dress. Then come down for breakfast." Since Quinn was right next to me, she saw him also.
I am doomed. I'm back in diapers for three weeks at a minimum. Three long weeks provided that I stay dry for each and every one of those nights, otherwise the count is restarted and might never end. To make matters worse, a couple of my buds are sleeping over next Friday night. I'll be lucky if they just tease me about being back in diapers. If I'm unlucky, they will tickle me until I lose control and wet again for their great amusement. I am doomed.
Once I was home I discovered that my own smooth pubis that was a good thing although I'll never tell Alvin such a thing. First, I found it strangely erotic and when I jerked off that night it was extra good.
Second, I won more at school than I made babysitting Alvin that one night. A few of the guys at school had gotten a challenge going. It had been started as a dare so all the guys with pubes had to join into the game. It was one of those silly macho dare things. In the gym showers on Monday, I happily claimed the cash. It was clear that I had the balls to shave my pubes off. I even got extra points (but no more money) for my cock was small. It was great timing and I never had to explain what happened.