Tommy Has a Babysitter

byCharles Petersunn©

"Do you have a rubber ducky or boat you like to play with?"

My gosh! How old does she think I am? "No, no, ma'am. I don't wash with anything. I mean, I don't play with anything."

"Well, if you're sure."

"I'm sure, really, honest."

"Well, I guess then maybe you are a big boy now."

"Yes, ma'am," he softly replied, not feeling particularly like a big boy.

Miss Landers then soaked one of the wash cloths in the bath water and squeezed it over his head a few times, getting his hair thoroughly soaked. She picked up the shampoo that was sitting by the tub, filled the palm of her hand, and proceeded to wash it into his hair.

"Miss Landers, Miss Landers," he protested, "I can wash myself! I always wash myself."

"No, no, dear, I need to do this. Now, keep your eyes closed. They'll sting if any of this shampoo gets into your eyes. We really should be using baby-safe shampoo. I'll bring some baby-safe shampoo the next time."

There was no way there was going to be a next time, no way at all.

She thoroughly washed his hair and said. "Okay now, get onto your knees, bend over, and rinse your hair out in the tub. Be sure to keep your eyes closed."

"Yes, ma'am," he replied, his eyes indeed stinging from the shampoo that had soaked through his tightly clenched eyes.

It was kind of good to have his eyes closed, as the less he saw of her the less he was reminded that he was naked before her. However, when he got into position he realized that he would be poking his naked bottom up in the air.

And, it was indeed a very cute sight. His bottom was even sweeter now, all glistening and shiny when wet. When his face was underwater she placed her hand on his bottom and openly stroked and fondled the soft, smooth curves.

His almost opened up his eyes at the shock of her touch. He did though work as fast as he could to rinse out his hair, springing back up to get his bottom back under the water and away from her hand.

But, she was not done. She proceeded to wash every inch of him. Like, every inch: his hands, his ears, behind his ears, his feet, under his arms. She made certain to get under his fingernails, just as his mother had insisted. Much of this was quite boring, albeit very demeaning. What boy would like to have his teacher wash under his arms? Not too many. But, it even got worse.

"Okay, Tommy, now stand up and turn around."

He figured she was going to wash his legs, although probably his fanny as well. He did as she instructed.

"Bend over, and let me clean your bottom."

What? "I don't think you need to clean me there," he protested.

"Tommy, is your bottom part of your body?"

"Well, yea, sure."

"And do dirty things come out of your bottom?"

He flushed with embarrassment, and didn't respond.

"I imagine that you even have brownie stripes in your briefs. Do you want me to check? I will be happy to check them. Does your mummy check them for you? If they're clean, then I won't need to clean you there."

He really didn't want her to check his briefs. Frankly, he didn't think she would find much, but he certainly didn't covet the thought of having her go through his underwear to check for brownie stripes even if none were found. And, if she found anything at all (which she probably would, at least a bit) it would be terribly, terribly embarrassing and he would still have to be washed back there. "No, no, that's fine."

"Okay then. Here, actually, get down on your knees and stick your bottom up for me."

This was so degrading. Could it really be any worse than this?

"Now, spread open your cheeks for me, Tommy. I need to get in there real good."

Well, apparently it could get worse. He looked back at her, looking so pathetic, pleading for her consideration. "Mother has never cleaned me back there, really. It's just not necessary."

"Oh I'm sure she did, Tommy, when you were younger. You just don't remember. Now, come on dear, and open it up for me like a good little boy."

"Really, Miss Landers, I just don't feel it's needed."

She rested her hand on his bottom and gave him a stern expression as she lightly patted his butt. "I suppose we could use an enema instead. Would you like that?"

Tom's heart was racing. "No, no, ma'am." He really, really didn't want that. He had never had one before but he was very confident that he would not enjoy it.

"But, even then I would still have to tell your mother how resistant you were and I don't think you would like to have that spanking. I suspect that she would even spank you while you're getting a second enema."

He looked away and reached back. He really couldn't believe he was doing this, spreading his cheeks open for Miss Landers, letting her see his most personal spot on his body, a part he had not even ever seen himself.

Miss Landers smiled broadly at the boy's humiliation, and at the sight of his little brown star. Again, she did not find a man's hairy asshole to be particularly appealing, and certainly not attractive, but this more innocent rose bud was actually really quite cute, and it didn't have any hair at all.

She first just rubbed the soap up and down and around and around his anus, getting it all clean and soapy.

That actually didn't feel too bad to Tom. In fact, it felt kind of nice. He didn't realize how tingly, tickly, and titillating it would feel to have something slippery and wet massaging his butt hole. He could feel all his muscles relaxing, including even his sphincter, and he gave himself over to what was in fact a rather pleasurable experience. He had never imagined Miss Landers tickling his butt hole when he was younger, but he hadn't then appreciated what it would be like to have your teacher tickle your anus.

He was even disappointed when she eventually stopped. But, she only did so in order to thoroughly soap up her finger. She even squirted some shampoo onto his puckered anus. He was now well prepared, and she brought her finger back to the hole, this time to insert rather than to tickle.

He at first instinctively clamped down hard with his sphincter, wanting to deny her entrance.

She felt his resistance and didn't try to push her finger in. Not yet. She at first just lightly, softly, affectionately, rubbed the tip of her finger around and around his butt hole, delicately massaging his anus with her wet and slippery finger tip.

Tom softly moaned in pleasure. He could even feel his dick beginning to swell. He was now finding this to be intensely erotic, although he imagined that there was no way he could admit that to anyone. It seemed so dirty, so naughty, so wrong, yet so nice, so sexy, so arousing.

She then forcefully shoved her finger deep up inside his rump. The intrusion was shocking, even appalling, for the boy. His eyes opened up wide with surprise. It didn't hurt. It did slip in very easily, as his sphincter was so relaxed and lubricated, but it did feel a bit uncomfortable and it was so wrong, so invasive, to have this woman's finger stuck up his butt. And, to make it even worse, she began to work her finger around and around within his rectum, like she was actually trying to clean him inside.

She was indeed. She pulled her finger back out with a big pop, loaded it up with more soap and shampoo, and then shoved it back up again, to wash and clean him inside.

"Doesn't that feel good Tommy?"

He wasn't sure how it felt. It sure felt odd. Maybe it felt good. But it was definitely odd.

"It always feels nice to get good and clean, to get a real good scrubbing."

She repeatedly removed, soaped, and reinserted her finger into his butt, at times exploring his insides, smiling as she felt his little prostate.

Tom was very grateful that he didn't have to go to the bathroom. That would have been terribly embarrassing for her to come across something. And, what if she would have wanted to watch him take a dump? There was no way she would do that. Would she? There was really no telling what this woman would or wouldn't do.

She at times was just shoving her finger in and out of his butt. He had the distinct impression that he was actually being finger fucked up the butt by his pretty and buxom elementary school teacher. But, she couldn't really being doing that, could she? Against his best wishes, he could feel his penis swelling further, which he found terribly confusing. It wasn't like he was really enjoying this, was he? It was just that it was his sexy teacher, in her sexy summery dress, doing naughty things to him. It was okay to find that pleasing, wasn't it?

"There, all clean, like a good little boy. When your mummy gets home, I think you should show her how clean you are back there."

Man, there was no way he was going to do that. He would go right to sleep as soon as this was over. There was no way that he would allow that.

She washed off her finger in the tub and said, "Okay, stand back up and let's do the front side now, and then we'll be done."

He was glad to get the butt cleaning over with. He did not though want to turn around quite yet as he was rather embarrassed over the growth of his penis. It was bad enough to have gotten aroused in front of her. It was ten times worse to have done so in response to her sticking her finger up his butt.

"Oh, that's okay, I can do that myself."

"Oh no, Tommy, that's the most special and important part to wash. Every boy needs to wash his pee-pee."

Tom's face flushed with embarrassment. "Yea, yea, I know, I know."

"Does your little man wear a hood?"

Tom furrowed his brow and turn his head back to Miss Landers, although keeping his private parts still turned away, has hand covering them to be doubly sure they were hidden from view. "Excuse me?" He didn't understand what she meant by that.

"Does your pee-pee have a coverlet?"

He still didn't understand.

"Foreskin?"

'Jeeeez,' he thought. 'Why didn't she just say that?' "Yea, sure, yes, it does." He didn't really like that he was not circumcised. He thought it looked goofy, all that curled skin bunched up at the end. He would sometimes even pull the foreskin down and off in the bathroom before entering a locker room so that when he took down his shorts people wouldn't see it. He felt it looked more manly that way with the foreskin pulled back.

"Well then, it's even doubly important to wash it there every day. Do you know what happens if you don't wash underneath your coverlet?"

Tom could feel his face getting real warm. "Yes, I know, I know."

"Well that's very good. Perhaps you are a big boy now. Why don't you tell me."

"Excuse me?"

"Tell your teacher what happens if you don't wash under your blankee."

This was really the babysitter from hell. He would have to insist that his mother never, never, ask her to babysit him again, forgetting for the moment that he shouldn't even have to go through this again with anyone. In any case, it was bad enough to admit to the existence of penis cheese, or smegma, but did he have to actually talk about it to her, his sixth grade teacher, while being naked in a bathtub?

"Now, don't be shy about it, Tommy. Little boys shouldn't be shy about things like this, especially with their babysitter."

"It can get dirty underneath."

"Have you ever gotten dirty underneath?"

His face got even warmer, actually hot. "No, no, it's never happened to me."

"Oh Tommy, I don't believe that one second. You're not lying to me, are you. If I ask your mother if you have ever had penis cheese, what will she say?"

There was no way, no way at all, that he was going to have them talk about this. They would probably even have him stand right there as they discussed it, perhaps even have his penis out for a penis cheese inspection. "Yes, yes, okay, yea, I've had it."


"Now that's much better. You turn around now and let Miss Landers clean the little man up, all the way from head to toe. We'll give him a good little bath so he is all fresh and clean, and there will be no nasty penis cheese gathering under his collar."


The good news is that all this discussion had managed to deflate his swelling. He was now back to his limp state. The bad news is that he had to turn and present his little limp penis to the pretty teacher.

He got up and turned to face her and reluctantly withdrew his hands from his privates, presenting for her eyes, for her inspection, his penis and testicles. And, with him standing in the tub and her kneeling before it, his privates were just inches from her eyes.

She smiled broadly. "Oh, he's such a cute little baby, all curled up in his blankee! He's just sleeping away, probably having wonderful little dreams." She looked up into his eyes, which were actually looking away. "What does your little man dream about, Tommy? Does he dream about playing with little girls?"

Tom would normally think that presenting his cock to his pretty teacher, the engaging, attractive, and voluptuous Miss Landers, would be a dream come true, particularly if he was presenting himself just inches from her eyes or, more importantly, her lips. He would assume that he would get rock hard within seconds. He had in fact imagined such a scenario when he was in her class. But, he had not imagined that it would be like this. He didn't respond.

"We'll try not to waken him while we give him his bath. It's best, don't you think, not to disturb him."

He knew what she was referring to, and he just nodded.

"And, besides, you wouldn't want to get a boner in front of your teacher, would you?"

Why couldn't she just get on with it? Although, if she continued to talk about it in such an humiliating way, the danger of it happening would certainly be low.

She thoroughly soaped up her hands and proceeded to wash him. She first did his testicles, being very heedful and gentle as she worked in the soap; firmly but sensitively working her fingers all around his tender sack and balls.

Tom closed his eyes, but this time more with nervous excitement than embarrassment. Her fingers did feel nice. This was now closer to what he had imagined. It certainly fell far short of what he had fantasied, but it was a darn good close second. He did not himself play with his balls when he masturbated. He typically, like all men perhaps, skipped the foreplay and went right to the meat of the matter: his dick. He hadn't imagined that it would add much to the experience to fondle, to play with, his testicles, but he now knew he was clearly wrong. It is amazing what one can learn from your teachers. They do apparently know quite a lot, and there was much to benefit from their instruction, their example. He vowed to try this the next time, as her fingers felt so, so good.

She kept the fingers of her left hand gently cuddling and nestling his nuts while she shifted her right hand to grasp his penis, now working the slippery soap into his soft shrunken shaft.

She of course pulled back the foreskin to get the soap underneath, and in fact kept sliding the foreskin on and off the head of his penis as she washed his little man. Sliding the foreskin on and off was a good way to clean the head. It was like the penis had its own built in slippery soft smooth shammy. To Tom, though, it really wasn't much different than being masturbated. He looked down, to see his penis in the feminine, gentle hands of Miss Landers, being held just above her prominently displayed breasts, and from this angle he was looking right down into that deep luscious cleavage. He could see her breasts wiggle and jiggle like two large bowls of jello as she slid his foreskin on and off his cock. He very quickly began to swell. It was really unavoidable.

She looked up at him and smiled sympathetically, "Oh my, I'm afraid I woke up the little darling."

"I'm sorry, I'm sorry, really, I'm sorry," he kept saying. He felt so embarrassed. Actually, he felt really good, at least physically. Whenever he had an erection he felt good. It just basically always felt good to have an erection. But, this time it was coupled with such a strong feeling of embarrassment. She was absolutely correct, he did not at all like getting a boner in front of his teacher, as if he was a little boy who could not control himself.

"Please don't tell my mother, Miss Landers." He sincerely wished she would not, but just saying so made him feel like he was accepting the 'fact' that he was being a very bad, shameful little boy.

Miss Landers, being the empathic teacher, however, was very understanding and reassuring. "Now, don't be ashamed, Tommy. This happens all the time when I wash little boys' penises. It's only natural to get excited."

That was reassuring, to an extent, although he wondered how many little boys' penises she had washed, and the fact was, he was no little boy.

"Actually, it's really very helpful for the cleaning. It's so much easier to do a very thorough and complete job when it's all stiff and hard like this." It was indeed, and she firmly wrapped her fingers around his stiff shaft and proceeded to slide her fist up and down its length, working the slippery soap into his skin and all around and around the shiny, swollen bulb. She was particularly thorough there, being sure to get the sensitive underside so completely and thoroughly cleaned. He jerked and twitched at the intense stimulation her warm soapy, slippery fingers were providing. "You see, it's so much easier now to work the soap into every single inch of the skin. Everything is all exposed. Do you make it hard like this, Tommy, when you clean it?"

Maybe he had, once or twice, by accident, but not usually. Nor did he reply. He wasn't about to tell her about how he masturbated. In any case, his mind was more focused on steadying himself, bracing himself with a hand against the tiled wall. This was very, very distinctly like being masturbated. In fact, even better than normal cause her hand was so slippery with soap. Plus, it was being masturbated by his elementary school teacher, the one with such big tits that were now really jiggling hard. This was indeed very much like the fantasies he had as a boy and obviously so much better as it was for real. This he would tell his friends, although how he got into this situation might be hard to explain.

All that could be heard in the room was the squishy and slurpy noises of Miss Landers's soapy hand cleansing, massaging, stroking the young man's hard, naked cock.

She eventually broke the silence though to ask. "Are you old enough to squirt, Tommy?"

"What? Well, yea, of course," he gasped, his voice breathless with arousal, with excitement. What a question to ask. He understood that she was pretending to treat him as a little boy, as part of the punishment his mother had worked out with her, but wasn't that a bit too much? Not only was he more than old enough, he was about to do it, any second now. He was indeed about to squirt, and he would do it all over Miss Landers's pretty face and onto that terribly wonderfully exposed cleavage. He would cum all over Miss Landers and her boobs. What could really be better than that. Suddenly the babysitter from hell became the babysitter from heaven. He didn't care if it got him into trouble. It would be well worth it, as this was well past any imagined fantasy. He would show her that he was indeed very much old enough to squirt.

"Well, we can't have you squirting it here." She let go of his hard cock and said, "My, my, you might even get some of it on my nice summer dress." She got up off her knees and stood up, presenting her large full breasts just inches from his eyes, now even more enticing as her dress had gotten quite wet and was clinging snugly to her boobs. He wondered if in fact he might even be able to see through the fabric a bit, seeing perhaps a bit of lacy brassiere. The dress was certainly tightly molded to her large round tits. "Do you like my dress, Tommy? I just got it today. I think it has such a pretty color. I just love pink, don't you? And, don't you just love the little red violets sprinkled all over? It's just so gay and happy."

Report Story

byCharles Petersunn© 22 comments/ 219239 views/ 48 favorites

Share the love

Report a Bug

PreviousNext
6 Pages:1234

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel