I babysat Tucker for years, ever since he was about seven and then, when he had just turned fourteen, he began coming out after his shower, in his pajamas, and would sit next to me as I watched TV.
It was pretty obvious that he had an erection and he seemed to want me to see how he was poked out. He also began leaving the bathroom door open when he showered, even once calling out to me that he'd left his pajamas in his room.
I was almost seventeen so I had quite a good idea what he was up to and humored him, taking his pajamas into him as he dried off. He made little effort to cover himself, in fact, even took special care to towel himself off over his middle.
I knew what he was up to and did my own game as well, mostly in what I wore when I came to babysit. I never made it too obvious so his parents would be suspicious but, a few times after they left, I would go in another room and remove my bra or my panties, especially when I wore a loose pair of shorts.
This went on for months, him finding a way to show me he had a hard-on, me giving him glimpses of my panties or even a peek at my pussy or breasts. He began to get a bit more bold especially when I came in to say goodnight which often went on for a bit as I would give him little looks at me.
He would be under the covers but it was obvious he was slowly masturbating. It kind of became a game, an unspoken game between us. It really turned me on that he was rubbing his dick while I was there, especially when he would lift his knees to hide it. But I knew and I would tease him even more.
I don't think he ever got off while I was sitting on the bed with him but I really can't be sure, either; he might have.
Then, one night I was there, he had made sure I saw his erect penis and then when he was in bed, his knees lifted to hide the movements underneath, I asked, "What are you doing under the covers, Tucker?"
"Nothing," was his immediate answer.
"I have an idea of what you were doing, Tucker."
"No, I wasn't doing anything, really."
"Come on, Tucker, I know what you were doing. It's not a big deal, you know. We all do it."
"You do it, too?"
"Of course. Everybody does, didn't your mom and dad tell you that? It's nothing to be ashamed of. Why don't you just go ahead and do it? I won't tell."
"Will you watch me?" he asked, confirming that my babysitting charge was certainly a sexual exhibitionist. "You won't ever tell?"
"I promise. I'd really like to watch you do it, Tucker."
The covers slid back and his briefs were down around his ankles. He smiled at me as his dick stood straight up from his lap.
"Go ahead, Tucker," I urged him and he asked me to hand him the bottle of hand lotion that was in his bedside drawer. He drizzled a line of lotion on his dick and began sliding his hand up and down as he looked at me. He really wanted for me to see him jack-off.
"Is it good, Tucker? Does it feel good?"
"Mmm, yeah, I really like you watching me do it."
"You've been wanting me to see your dick, haven't you?"
He looked kind of funny at me, hesitated, then admitted, "Yeah, I guess I was."
"I thought so," I told him as he stroked himself rather proudly while I looked on. I dropped my hand down onto my shorts and began rubbing, bringing a wide grin to his face.
"You're making me hot, Tucker," I told him, no doubt making his day.
"Mmm, it feels even better when you're here watching me do it," he moaned as his hand went up and down.
"You really like me watching you, don't you?" I teased and right then his cum began spurting up out from the end of his dick as he groaned in pleasure.
I handed him some tissues, kissed him goodnight and went into their spare bedroom and masturbated in the darkness.
It was about two weeks later when I was back to sit for Tucker.
Everything seemed back to the usual until his parents left. Then he disappeared only to return a few minutes later naked with a boner on display.
"Tucker, you're something else. Is this for me? You really like me seeing you like this, don't you?"
He grinned and just stood there proudly showing me his cock.
"I suppose you want to jack-off for me again, is that it?" I asked and he nodded. I told him to get some hand lotion and I would watch him.
He was right back with it and dribbled some on his palm and stood in front of me and began stroking as I widened my legs, showing a little skin near my pussy. I had worn some cutoff shorts and no panties, knowing something like this was likely to happen.
He jacked-off and then, after he'd wiped it up, sat there next to me while we watched a movie and he played with himself; I knew he was getting his jollies from doing it sitting right next to me.
"You like playing with yourself, don't you, Tucker?"
"Especially with you, Amy. I like for you to watch me."
"You like making me horny, don't you?" I said as my hand took a quick rub along the inseam underneath.
"Yeah, it's so cool to be like this."
"You'd like to fuck me with that, wouldn't you?"
"Yeah, more than anything. Could I?"
"No, Tucker, you may not. Don't you think this is enough?"
"You're really beautiful and so sexy, Amy, see what you do to my dick?"
"Come on, it's like that even when I'm not around."
"Okay, but you make me crazy, I just want to fuck you so bad."
"Well, it's not happening, so jack-off."
"Okay, I am, I am."
Soon, he was cumming as I rubbed a finger jammed up under the leg of my shorts. I knew it wouldn't be enough and that I'd have to use the guest room again but it was good enough for the moment. We watched the rest of the movie while he eagerly played with his dick, then I sent him up to bed.
"Are you coming up to say goodnight?"
"You just want to have me watch you masturbate again, right?"
"Yeah, I love it when you do. It makes it feel so good when you're there. Come on, you know I love doing it while you watch," he pleaded and I went up with him, watched him brush his teeth then get into bed and begin jacking-off for me.
I sat sideways on his bed so he could see up the short shorts I was wearing, maybe seeing a little pussy as I took a swipe back and forth into the leg opening just to make him crazy.
"I wish you'd let me use this on you, Amy. I'd always remember it, I promise."
"You wish, all right. Just jack-off, that's all you're getting."
I certainly didn't discourage him so much that he stopped, oh, no, he went right on stroking until he got off again.
After he cleaned himself, I kissed him goodnight and went down the hall for my turn. I left the lights off and the door ajar hoping he'd take a peek and I can't really be sure he did but, knowing my horny little Tucker, he probably did. He heard me if nothing else.
The next day, Melissa, my fourteen-year-old sister, came to my bedroom door and rapped. It was open so I told her to come in.
"What's up?" I asked and she told me she'd been talking with our mother about starting to offer babysitting services herself.
"So, could I go with you sometimes to see what it's like?"
I started laughing, just thinking about my main source of income, a boy her age who loved to show his penis to girls.
"Yeah, that might be a learning experience for you. I could take you on Saturday when I babysit for Tucker."
"Would you, really? That would be great. You're a great sister."
"Yeah, then Tucker would have another girl to show his dick to."
She stood there a minute.
"Show his dick?"
"Yeah, he loves to show his dick and he usually masturbates a couple of times while I'm there."
"You're shitting me, right?"
I grinned and told her I wasn't.
"I know Tucker from school. He shows you his dick? Right out in the open?"
"Naked ... he gets naked and shows me his dick and he jacks-off."
"He's cute. He really does that? You're not kidding me?"
"He really does that and, Melissa, I'm not kidding you. If you want to see your little classmate naked and jacking-off, come with me Saturday."
"Omigod, I'd love that, I'd love to see his dick and watch him jack it off. That's incredible."
"But you'll have to keep it quite, never tell a soul, after all, we'll all be in the same school, okay?"
She agreed and I was seeing a new and different side to my sister as her hormones started kicking in just as mine had a few years earlier. Melissa was becoming a hot, sexy girl.
I had called Tucker's parents to make sure they were okay with my bringing my sister and Melissa and I walked the two blocks to their house at six-thirty.
Tucker seemed normal, of course, and after they left he came and asked if he could talk with me, privately.
"Does she know what I do when you babysit me?"
"Just leave it to me, Tucker. Do you want to show Melissa your body? Jack-off for her, too?"
"Oh, yeah, she's hot, I'd love to do it. You think she'd be okay with that?"
"Just leave it to me," I told him and we went back into the den.
I sat down next to Mel and said to Tucker, "Take your clothes off and show my sister your dick," and he pulled off his teeshirt, pulled down his shorts and briefs to stand there proudly erect.
Melissa looked at me then back at Tucker, grinning ear-to-ear.
"Wanna see him jack-off?" I asked her and she nodded, obviously fascinated with the whole thing. I handed him the bottle of lotion and he put some on his palm and began, telling my sister, "I love doing this for your sister and now I'm doing it for you, Melissa. I think you're the hottest girl in my class. You're really making me hard."