I, Babysitter - Part 40


by Sawyer

Well, it took me long enough, but here it is! The start of the BRAND NEW series of stories - a whole new season, dontcha know! First up, this is a revamped version of this story that originally appeared in February 2000.

This thing is FAR from done!!

"Took you long enough, man," he said.

"Sorry," I said, throwing him my sleeping bag. "Things to do, see."

"Yeah, yeah," he said, walking back into his room. "I heard you talking it up with the old bitch."

"Gavin!" I snapped at him. "Stop that."

"Sorry."

"I know you're angry, but she, well, she's trying, dude."

He didn't say anything. He threw the sleeping bag down and sat on his bed. I walked over to him and stopped in the middle of the room to look around.

"So, this is your place?"

"My cell," he laughed, undoing his pants and dropping them down.

"Seems nice," I said, as I got my first faint scent of urine; I really hoped we would be camping out in the living room and not in here. This would really make me sick after awhile.

"I don't like it," he said, as he pulled the pants all of the way off. "The guest room is actually bigger. Kind of bites that they put me in here."

"I see," I said, looking around again, this time spotting the digital video camera sitting across from his bed on one of the two dressers. "WOW! This is tight!"

"Tell me about it," he laughed.

"I thought it was a still camera?" I said picking it up.

"What do you mean?"

"You know. A camera that only takes pictures, not video."

"Oh, that camera is somewhere else. This is Dad's," he said standing up and showing me how to turn it off and on. "I was playing around with it earlier...ahhh..today. Filming my own TV show."

"The Gavin Show?!" I laughed. "Sounds cool. We should watch it."

"Yeah...maybe later," he said, sitting back on the bed, as I turned it on and pointed it at him.

"Should we do this now, huh?" I asked, looking at him through the view-finder.

"Uh-huh." He took off his shirt, and put it on the floor. "After you turn the camera off!"

I turned it off and put it back. "Spoil-sport."

"You wouldn't want me videotaping your spanking your naked butt, would you?"

I paused for a moment - what would make him even think of something like that, much less say it? "Of course not," I said. This was one weird situation.

"I didn't think so."

"Are you going to be totally naked?" I asked, changing the subject as I put the camera aside.

"The only thing I'm allowed to wear from here until morning is the...the...thing," he said, pointing to the opened box of size 12 diapers.

"And you aren't allowed to put them on?"

"Nope," he said, as he took his socks off. "Sorry."

"But what about if you have to get up in the middle of the night and...well...?"

"Go to the bathroom?"

"Yeah," I laughed. It did seem kind of funny, now.

"I have to go in that," he nodded again at the diaper. "And they will change me in the morning."

"Ahhh, man," I said, wrinkling my nose. "That stinks...ahhhhh...I mean, that's TOO BAD!"

Gavin laughed. "I heard you the first time," he said. "Don't worry, you will be out of here and over spanking Vincent before they will get around to changing me."

"That just seems so wrong," I said.

"Diapering me or spanking Vincent?"

"You knew what I meant, wise ass."

"It is, but it does work, I guess." Gavin rested back on his bed. "It's actually been about three weeks since I wet the bed." He looked so anxious.

"So, it's not every night?"

"Not any more." Man, he looked so sad and hopeless, laying there. "I hope not again either."

"I see," I said, as I became aware of the fact that I was rock hard in my pants. I could think of so many other things to do with that mostly nude kid - diapering him was not one of them!

"We need to hurry this up," he whispered. "They might poke their heads in any moment, and I don't want them to see my red butt from the dickweed at the mall!"

"You sure your parents would really freak?"

"I told you about my Uncle Lou, right?"

"Yeah, sorry." I had forgotten about the Uncle that was banished for once raising an open hand to little Gavin.

"And he was my Mom's own brother. Let's just do this and do this quick."

"Gavin," I said very softly. "Why didn't you tell me? About the diaper?"

His eyes began to water. "Please Matty not again - not - not now," he begged. "Just get this over with. I will explain everything later."

I sighed - what else was I to do?

"What do I do?" I said softly.

"You need to take off my underpants and..."

"Gav, can't you do that, dude?"

"I'm - I'm not allowed...not when I'm being punished like this," he closed his eyes and gulped. "Go ahead...It's cool...I won't mind...just...just don't tell anyone."

"Of course not, buddy."

I looked down at him. He was quivering and nervous and so scared. I knew I was making things worse by acting like a dick, but I couldn't help it. This was just too weird, even for me. I leaned over and took a hold of each side of his underpants. Slowly I lowered them down past his thighs. His beautiful penis sprung out. It was the second time in one day that I got to see it, but this was the first time, since that time he rode my back in the bath tub that 'I could see it this close.

No...

...it was never this close before...

...this time it was just a few inches away from my face!

Ooooh...man!

I knew what it felt like in my hand...oh man oh man...I wanted desperately to see what it felt like in my mouth...but I couldn't...!

I gulped, and looked over my shoulder to the open bedroom door, then back to my friend. The underpants went past his knees, over his calves, and eventually I got them over his feet. I then put them on his bed and just looked at Gav, looking so vulnerable and meek. His eyes were still closed, but I could see tears running down his cheeks again.

"Quick," he whispered, with eyes still closed. "There should be one of those - those things in the bottom drawer of the dresser."

"Which dresser, dude?"

"The one next to my bed."

"What about the open box?"

"No," he said. "Need to go through the ones already in the drawer first." He opened his eyes. "She has a ton of them stashed everywhere. She doesn't even know how many she has, she has so many."

"I know."

"I mean, she didn't need to buy the ones at the supermarket," he began to cry, his voice rising and tears flowing and flowing again.

"I know, sweet-heart," I said, leaning over and kissing his forehead. "She confessed."

He looked at me confused, then closed his eyes again, before whispering, "Bitch."

Breathlessly I went over and opened the drawer up. Sure enough, there was just one pair of plastic underpants, size 12, in there. I took it out and turned around.

Gavin was now holding his legs up to his chest. His eyes were open, and they were darting back and forth to the open door and to me.

"Hurry up, with that," he whispered. "Let's get that on me."

I sighed. I went over and put it down under his butt.

"No, that's upside down!" he snapped.

"Ok, ok," I said. "I've never done this before." I flipped the diaper. "What now?"

"How's my ass look?"

"Cute," I giggled.

"Ha-ha...is it still red?"

"Yeah," I said, touching it.

"Ouch!" he cried out.

"Sorry."

"Dang! I can't believe it's still stinging!"

"I think mine will be stinging well into Mr. Cobbler's class tomorrow," I said checking him out from head to toe, which (coincidentally, were now only an inch from each other!). I was sitting at the foot of the bed. It was like his ass and balls were on a private exhibition just for me.

"Crap," he said. "There should be some lotion over there, on the dresser...the same dresser."

I got up and walked over. "Which stuff is it?" I asked.

"That white bottle," he said. "Next to the tube of Vaseline!"

"Oh, ok," I said, picking it up.

"Quick, rub that on my rear end," he said, motioning for me to come over there quickly. "These - these things are uncomfortable enough on their own. I can't imagine what it would feel like to be wearing them with a - well ..."

"Spanked butt?" I whispered, sitting back down, and opening the jar of lotion.

"Yeah," he said, closing his eyes again. "God this sucks."

I began to smear the lotion on without saying a word. I figured he would say something if I was doing it wrong. He just laid there, holding his legs tightly to his chest, trying not to burst out sobbing even more.

"Ok," I said, as I finished up, my hand straying off course and gently rubbing his still beautifully hairless testicles. "I guess I'm done."

He positioned himself over the back of the diaper, and spread his legs. "Hurry," he said. "Bring those sides around this way...yeah ...like that...now bring that part up through ...yeah... ok...now, fasten them with the velcro and... ok..."

"No pins?" I asked, finishing him up.

"Not for the plastic ones," he said, sitting up, but unable to look at me in the eyes. "Sometimes I have to wear cloth ones. They are more comfortable, but much messier."

I wrinkled my face.

"Sorry," he said. "You didn't need to know that, did you?"

I laughed and shook my head.

"Is that it?"

"That's it," he said.

"Not as bad as I thought."

"You weren't the one being diapered, Matt!"

"Touche," I said with a slight, relieved chuckle. "Too bad for Lee he can't see us now, huh?"

Gavin wiped his eyes. "Why would you say that?"

"He would have probably enjoyed it, is all...sorry, I know this isn't funny."

Gavin smiled. "That's ok, I know...if it was someone else I'd find it all pretty funny too." He then got serious. "Please don't tell him, Matt. Please!"

I hugged him. "Of course not, buddy. This is between me and you...and your folks." I wiped away the tears that were all the way down to his full, perfect lips. "Besides, I don't think Lee needs any more wild ideas, do you?"

Gavin smiled and laughed. "Imagine him taking a bunch of diapers to camp next year?" he whispered.

"Or him diapering up his father's cub scout troop!" I said.

"Oh, man," Gavin said as he leaned back on the bed. "I didn't think about that. Those parents would be pissed as hell!"

"He wouldn't do anything like that, anyway, but it is a funny image."

"Yeah," Gavin sighed. "Funny when it is someone else."

We sat in silence for a few minutes thinking about what had just happened and what this might mean. Eventually his mother did stick her head in.

"Safe to come in?" she asked.

"Yeah," Gavin said, as he turned and stood up. He then twirled around. "Matt did it."

"All by yourself, Matthew?" she asked.

"Gav just told me what to do."

She smiled, and told us to come down for dinner, and nothing else was mentioned about the diaper or the punishment that night. She was so pleased with the way I had handled Gav, she asked if I was free to come over Friday night to babysit him while she and Gavin's father went to a preview of an opera in Pittsburgh. I had wanted to go to the big football game at the high school, but the Rams kind of sucked this year ao I said sure - Gavin actually seemed pleased with that development.

We did sleep in the living room, in our sleeping bags, but when I woke up in the middle of the night he was gone - he had gone back to the comfort of his bed.

I overslept, but figured the Hansons wouldn't mind if I was a little late. I got my stuff together and went up to see Gavin. He was out cold, as I lightly rocked him awake. _d_a_m_n_ he was cute!

"Hey," I said when he opened his eyes.

"Hey."

"Sorry I have to leave," I said.

"That's ok," he said, yawning. "I understand."

"Cool."

"I'm sorry I abandoned you. My back was hurting on the floor."

I nodded. "That's fine. You want me to call you when I get home from Vincent's?"

"No, I'm busy today with Dad all day."

"Oh, ok then. Guess I'll watch the game with Dad then."

"Who are they playing?"

"Buffalo."

Gavin was silent for a moment. He was still trying to wake up. "So...so you are going to go over and spank Vincent this morning, huh?"

I smiled. "If it's Sunday, it must be." I looked at his clock. "In fact I'm going to be a little late."

"I'm sure his butt will wait."

"I'm sure it will too," I laughed.

"That sounds like fun," he sighed.

"It...it really isn't, but I guess it is," I sighed. "I can't explain...it's different than with us."

"You should take the video camera!"

I laughed. "You horned up little spanking monkey! You'll have another chance soon enough, " I said, sitting on his bed and tickling him.

"Heeee-heeeee-heeee You said SPANKING THE MONKEY!!!" My ticking intensified, as he then yelled out, "Stop it!" he giggled. "I'm- oooohhhh - I'm....!"

I stopped and smiled at the beautiful boy. "I wouldn't want you wetting your pants!"

"Ha - ha," he said, smirking, as he brought his covers up to his chin.

"I should go," I said, standing up.

"What about tomorrow?" he blurted out.

"Monday? What about Monday for what?"

"How about I spank you right after school tomorrow?" he said, still looking very innocent in his bed.

"After school?"

"Uh - huh," he said. "That way this will all be behind us."

"No pun intended, right?"

He smiled.

"Right."

"Fine, after school it is," I said, leaning over and kissing his forehead. "I'll see you at the bus stop, dude."


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