Tommy's Babysitting Experience - Chapter 1 & 2


This is a story of a somewhat odd relationship. It might not be the cup of tea for everyone, but that is, of course, the nature of erotic fantasies. We all have quite different fantasies, and not all of them will I enjoy or expect you to enjoy. It has CFNM and submission themes. For those who would enjoy this, please do, and, please note, all characters in this story are indeed at least eighteen years old.

- - - - - - - - - - - - - - - - - -

"Mother, I'm much too old for a babysitter." That was certainly true. Thomas Jackson was 18 years old, a senior in high school. He couldn't even remember the last time he had a babysitter.

"Apparently you're not."

"Mother, I said I was sorry. I said it wouldn't happen again."

Tom's parents had left him home alone last week, only to return to find that he had hosted a rather loud, rambunctious party. The house was a complete mess. There were empty, half-full, and spilled cola cans strewn everywhere. Two neighbors had complained about the noise. There were even cigarette burns on the couch and he knew he wasn't even suppose to smoke, let alone smoke in the house, let alone allow a burning cigarette to fall onto the couch. He had denied that he had been doing the smoking, but that hardly mattered. He was obviously not demonstrating any maturity or sound judgment in allowing one of his friends to drop a lit cigarette onto the couch. Goodness, the whole house could have burned down! No, they were very, very upset, and that was putting it mildly. To express their frustration, their disappointment, they were going to teach him a lesson. If he was unable to act like an adult when they were away from home, then he would not be treated like an adult.

"I've asked Miss Landers to come over and sit for you."

"Miss Landers?!" Miss Landers was a neighbor of theirs, one of the neighbors who had complained about the noise. That was partly why Mrs. Jackson asked her to do the sitting. But, there was also one other important reason for asking her in particular. She was a bit more than just a neighbor. She had been Tom's sixth grade teacher. What better person to convey the message that you're still acting like a little boy than having one of your elementary school teachers baby sit you. She was really a very good choice for this lesson in growth and maturity.

"Now don't act all upset and everything. You know how much you like her." Mrs. Jackson looked down knowingly at her glaring son. He wasn't a very tall young man. His mother was actually a good two inches taller. She said, "As I recall, you had quite the crush on her when you were a little boy."

Tom's face reddened at the reminder, a reminder his mother never seemed to fail to enjoy. It was though quite true. He had a big crush on her when he was in the sixth grade, and it didn't help squelch his young passion that she was also a neighbor. When he was a boy he would often visit her at her home and offer to run errands, help with her gardening, feed her puppy when she was out of town, or just about anything else she wanted.

Miss Landers was not troubled or offended by the puppy love. It was not unusual for young boys to develop a crush on her. She was a very pretty lady with long wavy brown hair, large, round hazel eyes that seemed to sparkle behind her spectacles, and rosy red cheeks with quite pleasant dimples that would always appear when she smiled, which she did quite a bit. She was everyone's favorite. And, it probably did help as well that she had very shapely legs, a perky bottom that was so nicely and so often displayed by her tight skirts, and really quite prominent, full breasts, which she would try to hide behind suit jackets, but once the classroom became warm, off the jacket would come, much to the boys' delight.

She would just be patient with the young boys' crushes. They would eventually grow out of them, particularly when they graduated up to the sixth grade and she was no longer in their line of vision. Tommy's though had lasted much longer than most, probably because he could see her so often outside of class.

"Mother, this is really, really embarrassing."

"Well, you should have thought about that before you decided to have your friends over to burn down the house when we left you alone."

"They didn't burn the house down."

"Are you getting smart with me, young man?"

"No, mother."

"If you like, we can have Miss Landers come over every time you're here by yourself."

"That's not necessary."

"Well, we'll just see. If Miss Landers reports that you were a good little boy, that you behaved yourself and minded her, then perhaps we can trust that you will act your age and behave maturely and responsibly the next time we have to leave you home alone. Now, get upstairs and into your pj's as she will arrive any second now."

"Pajamas? I have to put on pajamas?" He stopped wearing pajamas a couple of years ago. He considered them to be immature and childish. And, besides, even when he did wear them, he wouldn't wear them in front of his parents or their guests.

"Yes, yes you do. It will be bedtime soon and I want you to be ready. Miss Landers was very nice to come over on such short notice. You could at least demonstrate some consideration for her by being prepared for bed. Now, get yourself upstairs and change into your pj's right now or you will know it tomorrow!"

"Ah mom!" However, the expression on her face, as well as the arrival of his father, spoke quite loudly and clearly. He really had little choice. He was eighteen but he was still in high school and still lived at home. As his father would say, "When you are under my roof, you play by my rules!" He turned around and dragged his feet down the hall and up the stairs to his bedroom. This was so unfair, and so infantalizing. His friends would never believe it. Actually, he didn't think he would even want to tell his friends. They would probably think it was rather funny and may never let him live it down.

He at least chose pajamas that were the most adult. They were solid black. As he looked at himself in the mirror, he wondered if it would be as bad as he thought. They didn't look so bad. Hugh Hefner always wore pajamas, and typically ones just like these. Nobody questioned his masculinity. Of course, his were probably silk rather than cotton. But, still, these didn't look too bad.

"Tommy! Hurry up!" His mother called from the front hallway. "Your sitter is here and we have to go. C'mon down and say hello."

With a deep sigh he trudged to the stairs and pattered down the steps in his socks. He felt so childish.

And, he felt much worse when he saw her. Just the sight of her made him feel like he was back in the sixth grade.

Miss Landers bent over when she greeted him, her hands on her knees. Tom had been one of the littlest boys in her class, and he was still rather short for a guy. She smiled sweetly at him, her dimples appearing. "Hello Tommy. I'm going to sit for you tonight. Won't that be nice?"

A part of this might not in fact be so bad though, as Miss Landers was not wearing one of her business suits. She was in fact wearing a rather tight pink summer dress with open shoulders and very thin straps that hardly seemed to have the strength to hold up a dress, not that her dress was much to hold up. It hung quite low on her breasts, providing rather nice cleavage, more than he had ever seen before, and quite a bit more as she bent over to greet him. His eyes opened up wide as the tops of her breasts appeared to almost spill out of her dress.

"I love your pj's. Just like James Bond. I think he wore pj's like that in one of his movies. Were you trying to pretend like you were James Bond?"

He stared blankly at her. He said flatly, "No. No. I wasn't." Trying to look like James Bond in your pj's was tremendously childish. He considered explaining that they were like the ones that Hugh Hefner wore, but that could in fact just make matters worse.

"Well, I think you look very handsome in them."

He didn't respond.

"Tommy," his mother said. "What do you say to Miss Landers?"

No, maybe this wouldn't be much fun at all. How much fun could it be to be treated like you were twelve years old again? He obediently replied, "Thank you, Miss Landers."

She smiled at him, bent over once again, and extended her hand.

He smiled awkwardly back, his eyes going to the cleavage as they politely shook hands, the tops of her breasts jiggling even with this little bit of movement.

Memories of his childhood flooded back: memories of admiring those luscious breasts that at times seemed to want to burst through her tight blouses, ripping out the buttons that were straining to be undone. He and his friends would at times make bets on whether one of the buttons would indeed slip its grip. None of them ever did, but a few times it seemed to get awfully close. When she hung over your shoulder to help you with a problem, it was maddening. His smile now felt a bit more sincere.

"Well, I'm so glad you're feeling better about this, Tommy," his mother said. She turned to Miss Landers as Mr. Jackson helped her put on her coat. "He got all upset when I told him to put on his pj's but I actually think he likes showing them off for you."

"Mother!" Tom exclaimed. It would be so nice to get the conversation off of his pajamas.

His mother leaned toward Miss Landers and in a stage whisper said, "He calls them his 'Hugh Hefner' pj's." They both had a giggle over that.

"Mother, please."

His mother, though, simply ignored him. "You know, he had quite the crush on you when he was a little boy."

Tom's face flushed red.

"Well, he does look very cute in them." Miss Landers turned to him. "I imagine they're very comfy."

His smile had long disappeared.

"Well, just see that he is in bed by ten o'clock, and," she turned to Tommy, "no cookies in bed."

Tom rolled his eyes. It was like he was in some sort of twilight zone, where time had been reversed. Mr. Edwards, his fifth grade teacher, had at one time threatened to send him back to the third grade if he continued to misbehave. He later realized that he must have been only bluffing, but at the time he thought Mr. Edwards meant it and he acted much, much better after that, at least for a few weeks. Imagine having to go back two grades and start over? That was frightening. Well, he seems to now be going back six grades.

And, it got even worse as his parents were heading out the door. His mother suddenly looked back and said. "You know, actually, Miss Landers, why don't you have Tommy take a bath. I think he's having a bit of a body odor problem. You know, budding puberty and all."

"My gosh mother!" Tom protested. This was really going much, much too far. He didn't need a bath, at least he didn't think he did. More to the point, he didn't take baths anymore. He took showers.

"Yes, Mrs. Jackson, I will be sure that he gets a very thorough cleaning."

"Yes, yes, please do. Make sure that he washes behind his ears and under his fingernails. Don't let him get away with just a superficial wash. He needs a good scrubbing."

"Mother, really."

"You know what I am talking about, young man. Now, we have to go. You do everything she says, Tommy. When I return, I want to hear from Miss Landers that you were a good little boy." She turned to Miss Landers for the final word. "If he disobeys you in any way, you let me know and he will get a good spanking!"

He so wished that she would just leave. Once she left it would probably be fine. Just please leave.

When his mother did depart, Miss Landers turned to Tom, took his hand, and led him down the hall to the bathroom. "Well, very good, Tommy, let's go have your bath. Where is it?"

"At the end of the hall," he reluctantly replied. Tom dragged along behind her, feeling very frustrated and annoyed at the thought that he would have to take a bath. It also didn't help that she led him along by the hand, just like one would do for a recalcitrant little boy. There really was no need for a bath, and he certainly didn't care for his mother's suggestion that he smelled. He knew though he would check once he got into the privacy of the bathroom. Did he really smell?

Being dragged along behind Miss Landers did provide the opportunity to admire her behind, which swayed nicely in her short summer dress. The skirt was really quite short. It didn't extend much beyond her bottom, which was as perky as it had ever been. He could even see the top of her thigh-high nylons, which made little swishing noises as her thighs rubbed back and forth, accompanied by the clicking of her high heels along the wood floor of the hallway. He briefly harbored the fantasy of her joining him in the bath. It was a rather nice fantasy, and she was helping him to ponder such a fantasy by taking him by the hand to the bathroom. He wondered if he should, if he might, even suggest it? No, that was a purely crazy thought. But, still, he was eighteen now. It wasn't like inappropriate, was it? And, she did say, 'Let's go have your bath.' He could suggest that he just misunderstood what she said. No, no, no! He had to stop this thinking as his dick was now swelling within his boxers. He would not particularly like his pj's to be sticking out by the time they reached the bathroom, and the fantasy was certainly quite absurd.

But, it didn't help that she led him right into the bathroom. He assumed that she would just drop him off at the door. Instead, she walked in with him.

She did let go of his hand as soon as they entered the bathroom, but she did so in order to run the bath water. He didn't really like her doing that. He could do that himself. Even when he was still taking baths, there came a point when he ran his own water. He couldn't recall for sure whether he did run his own bath in the sixth grade. He must have, as he was indeed beginning puberty back then. In any case, it only added to the feeling that he was being treated like a little boy. But, that was obviously their intention, his mother and Miss Landers. They were going to make their point by treating him as if he was in fact just a little boy.

Still, though, her running the bath did give him an opportunity to freely admire the sight of her bottom sticking up as she bent over the tub. Her skirt was rising up quite high on her thighs, well past the tops of her nylons and almost high enough to get to her panties. He considered dropping down onto his knees to peek up her skirt. He and his friends had done that a few times in her class, and this was much better than what they had been offered back then. Plus, her breasts were now hanging down, even swinging a bit in her loose dress as she worked at the hot and cold faucets, trying to get them just right. He adjusted his penis within his boxers as her attention was focused on getting the water at the right temperature.

"Tommy," she said, still concentrating on the faucets.

"Yes, ma'am," he replied.

"Why don't you get out of those pj's while I get the water ready."

He was swept away by a rush of anxiety, even panic. "What?"

She turned back to him, smile sweetly as she continued to monitor the water with her left hand as she spoke to him. "Get out of your pj's, silly" she repeated, not acknowledging or even seeming to be aware that the suggestion was so inappropriate, so wrong, so provocative. "You don't want to take a bath in your pajamas, do you?" She turned her attention back to the water rushing out of the faucet and laughed at the silliness of him bathing in his pj's.

Tom now asserted his age. "Miss Landers, I just don't think that's right."

She again looked back at him. "But, what's wrong, Tommy?"

"I mean, um, well, you shouldn't be seeing me naked, you know."

She smiled reassuringly, like a mother to a young boy. "Oh Tommy, I've babysat boys quite a number of times, along with being a teacher, and I've seen lots of little boys' pee-pees. Now, don't you be embarrassed about that at all."

"But, ma'am. I'm not a little boy anymore. I'm a young man."

"Oh pish posh. And, besides, your mother told me to be sure that you got good and clean. I don't see how I can do that if I'm not even here."

She was going to watch him bathe? This was going from bad to worse. Although, perhaps his fantasy would actually come true? "Are you going to bathe with me?"

She laughed loudly at that suggestion, her breasts jiggling with her amusement. "You are the little scamp, aren't you! Don't be silly, Tommy. That would be most inappropriate indeed, don't you think? Do you think a teacher really should take a bath with one of her students?" She looked back at him. "Did you used to think about having a bath with me when you were in my class?"

His face reddened. That wasn't actually one of the fantasies he used to have. But, it wasn't perhaps too far off from many of them he did have, and any reference to those fantasies was now terribly embarrassing. "No, no, no I didn't, not at all."

"No, of course not," she replied. "You're a good little boy, aren't you." She had gotten the water at the temperature she wanted and so turned her full attention to him, sitting on the edge of the tub, her hands clasped demurely in her lap, her breasts presented so prominently before her, her skirt riding up high on her thighs, the top of her nylons so clearly displayed beneath her clasped hands. "You do want me to tell your mother that you were a good little boy, don't you?"

He surely did want that. He wouldn't want to go through this again. "Yes, ma'am."

"And she told you to do everything I said."

"Yes, ma'am."

"Alright then, let's get out of those pj's and into the water. The tub is just about filled and I think you'll really like it. It's nice and hot."

Well, one consolation was that the discussion and anxiety had curtailed his budding erection. Imagine if he still had that?

He turned his back to Miss Landers, unbuttoned and removed his pj top, and then pulled down the bottoms and boxers.

Miss Landers smiled at the sight of the boy's cute little rump. She did not find a guy's butt particularly appealing. Tommy's though was really rather cute, perhaps because he was a rather short, little guy. Plus, when he bent full over his testicles came into view. She suppressed a giggle. They were a bit small.

Tom stepped out of his pajama bottoms and into the tub, left foot first. He would normally put in his right foot first, but this way he could keep his back to his teacher. He really didn't want to show her his stuff. He wouldn't want her to see him when he was all limp and curled up. It was not particularly impressive then. But, then again, he would be even more embarrassed if he showed her an erection. She would naturally consider him to be a pervert, and might even be shocked and appalled. What if she told his mother about it? And, she probably would. Imagine having your babysitter, or your teacher, tell your mother that you got uncontrollable erections. It was clear, either way he lost.

The water was a bit too hot for him and he just stood there for awhile, waiting for his feet and ankles to acclimate.

"Now hurry up, Tommy. You have to go to bed soon and surely you want to be able to watch at least one TV show." She added as she patted him on the bottom, "You just get that cute little fanny of yours down into the water!" It was so darling to pat, so soft and jiggly.

Tom quickly sat down, not particularly enjoying the patting on his bare butt, but he paused just as his nuts hit the hot water. Did she make it so hot on purpose? He grimaced and then let his weight bring him all the way in.

"Good boy, Tommy! Now, that wasn't so hard, was it?"

"No, ma'am," he glumly replied. Boy, imagine if his friends could see him now. They would laugh so hard. He would never get over it!

"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.


'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."

Tom didn't know what he was feeling. His eyes were just glued to two large pink globes sprinkled with red violets. He was speechless, and breathless. He wanted to cum so bad. He had been so close. But, instead, he had to just stand there, his hard dick thrusting out, his eyes just inches from those fantastic boobs. He so much wanted to just bury his face in them, in their soft, wet fullness, and then grasp his cock and jerk it off. It wouldn't take long, just a couple more seconds and it would be over. But, with the releasing of her hand from his cock the spell was broken, and he now had enough rationality, enough capacity to reason, that he knew he shouldn't do it. But, man, would he take care of himself when he did get to bed. At the moment, he no longer minded having to go to bed early tonight. He wanted to go to bed right after his bath. He turned his face up to the taller woman, looking up past her jutting mounds to her smiling face, her large pretty eyes, and her fluttering lashes, and said, "Yes, it's a very pretty dress."

"That's so sweet of you. Such a nice little man." He took some solace in her finally referring to him as a man, even if he was still little.

"But, oh my," she exclaimed, "I seem to have gotten a bit wet myself. I better get out of this and hang it up to dry. I certainly can't be walking around in a wet dress, can I, Tommy?"

"No, ma'am. You certainly shouldn't do that." He sure hoped that was the right answer.

She pulled the thin straps off her shoulders, all the while smiling so coquettishly. She held the dress against her breasts as she pulled her arms free of the straps. Once the straps were hanging free she smiled at him and let her hands fall to her sides. The wet dress clung to her breasts, but only briefly, and then slipped to the floor, to gather at her feet in a small crumpled pile of pink with red violet sprinkles.

But, he had not followed the path of the dress down to her feet. His eyes were instead glued to what the dress revealed. There before him was the pretty, the voluptuous, Miss Landers, dressed only in her brassiere, panties, garter belt, nylons, and high heels. It was a boy's every dream to have his teacher dressed this way, or undressed this way, standing before him. His dick gave an instinctive twitch of approval.

She was wearing a white lacy, half cup, strapless brassiere. The cups were no more than just that, cups filled to the brim, actually overflowing, with soft full white breasts that rose up well past the rims like two large pale mounds of ice cream. And, her stiff, perky nipples were readily evident through the thin lace. Even if the cups were solid cotton he still would have seen them, as they were so stiff and pointy. Would it be wrong to grab hold of his cock now? Wasn't that only natural?

His eyes traveled down further to her panties, which were matching white lace bikini panties. They seemed to be two sizes too small, as they covered very little and were so very, very tight. The lace ended at the most important spot, the spot where a rising mound of flesh could be seen, but they were still so snug that he could clearly see a split in the mound: Miss Landers's camel toe. He was actually looking at Miss Landers's camel toe? Okay, he really had to grab hold of his cock now. It's obvious that she would want him to. Why else take off the dress?

"Do you like seeing your teacher in her undies?"

"Um, yea," he replied, taking hold of his hard cock.

"Tommy! My goodness! No!"

He quickly let go. No, apparently she didn't want him to do that.

"Tommy, did your mother tell you it was okay to play with yourself in front of your teacher?"

He shook his head, suddenly feeling very nervous and concerned.

She put her hands on her hips and looked at him quite sternly, as she had done when he had misbehaved in class. "Well, I would certainly hope not. Do you think it is proper to play with your hard stiff pee-pee in front of your teacher?"

"No, ma'am. No, definitely not." He wondered if she was going to have him stand in the corner. Maybe he could at least play with himself there.

"Yes, well, I can see now why your mother had me come over. Goodness gracious. Did you and all your little friends play with yourselves at your party?"

"No, ma'am. No, no, no we didn't."

"Well, I do understand that boys do get erections when they reach a certain age, but you must also know that you need to learn to control yourself. You can't just start playing with yourself the first time you see a pretty girl."

"No, ma'am, of course not. I won't do it again."

"Well, alright then. Now, you get out of that tub and I will dry you off."

"Yes, ma'am." He carefully stepped out. He was always careful to step out of a tub, having once slipped on the wet tiled floor, badly bruising his hip. And, at the moment, he felt especially unsteady on his feet, and so he moved quite gingerly.

"Here, let me help you," she said, and used her left hand on his shoulder to help steady him, her right hand grasping hold of his stiff dick to guide him from the tub.

Tom wasn't at all sure why she would use his hardened cock to help get him out of the bath, but at the moment he was not complaining. It just felt so good to have at least someone's hand on it, and her hand was in fact a lot better than his own.

She retrieved a large bath towel from a lower cabinet and proceeded to dry him off. She made sure that she got every inch of him, and paid particular attention to drying his bottom, even between the cheeks, down into his crack. She made him bend over for that, and even spread his cheeks apart. "We don't want you to get a rash or anything," she said, as she gently rubbed the soft cloth up and down within the crack of his butt. She then bent over very close, getting her face just a couple of inches from his butt, perhaps even less, and lightly blew soft puffs of air against his anus.

It felt strangely erotic to Tom, having a woman blowing wisps of air at his anus. How very subtle, how very alluring.

She did, though, explain. "This will help you get even dryer. You know, it can be very helpful to use a hair dryer around your pee-pee after you bathe, so you don't develop any nasty old crotch rot." His penis began to soften once again.

But, it sprung right back up when she turned him around to dry him there, using her special drying technique. She pulled back his foreskin and lightly blew puffs of air all around the crown, even on, or perhaps especially so, underneath the crown, where he was most sensitive to touch. He became so stiff and hard. He wondered if he might even be able to cum simply by the touch of puffs of air, it felt so nice, and it was so well complemented by the sight of her red lips, less than an inch from his swollen bulb, all puckered up as if she was actually going to kiss him right on the tip, all over the crown, and underneath. What a wonderful time it would be now to cum. It would just splash all over those sweet, feminine puckered lips and then drip down into that deep valley of white wiggly pulchritude hanging out beneath his stiff, swollen cock.

But, he didn't get the opportunity to find out, as she didn't do it too long, or at least not long enough. She got back up on her feet, her breasts wiggling in their fragile cups.

Miss Landers then grasped his penis in her left hand, and led him out of the bathroom. "Now, let's get you into a fresh pair of pj's."

As they left the bathroom, she asked. "Which way to your bedroom?"

"Upstairs, ma'am," he softly, deferentially, replied. Her hand, of course, felt terribly nice grasping his cock. What could be better than having your teacher dressed only in her undies grabbing hold of your naked hard cock? But, she wasn't doing it to jerk him off. It was not a sensual, sexual hold. And, there was something about being led around by your erection that made one feel a bit demeaned, a bit childish.

"Well, then, let's go see what we can find," and she led him up the stairs, towing him along by his hard cock.

His eyes were fixed on her swinging, swaying pantied bottom as they worked their way up the stairs. The panties were so tight on Miss Landers's round perky ass. He could see every curve, all her roundness, wagging and waving this way and that as she worked her way up the stairs. He always enjoyed following the sight of a girl's bottom as he trailed her up a stairway, and one dressed only in small, tight panties was a step even higher. It was quickly becoming quite erotic again. A pretty woman was grasping his hard cock, her bottom was swinging flirtatiously before him, and they were headed to his bedroom. He was actually going to be in his bedroom, naked, with his teacher, dressed only in her undies. This part he would likely tell his friends; well, maybe not the part where she is towing him by his dick.

"You know, Tommy," she explained as she led him up the stairs. "A few of my students have at times come around my house and peeked through my windows." She stopped and turned back down to him, looking him in the eye sternly, while firmly, roughly, squeezing on his cock. "You never did anything like that, did you?"

Actually, he had, maybe once, maybe in fact twice. But, he had never seen anything. "No, ma'am."

She cocked an eyebrow, trying to judge if he was lying. She knew he was, and so could Tom tell that she knew, or at least he suspected that she didn't believe him. Maybe there was more to what she was doing tonight than just punishment for having a party.

She turned back away and continued to lead him along by his cock. "Well, I caught one of them once. Little Timmy Thompson. He was peaking through my bedroom window when I was only dressed in my panties and brassiere." She stopped and turned back once again, this time with a flirtatious smile. "Just like I'm dressed right now," providing him this time with a more gentle, sensual squeeze.

"Yes, ma'am," he gulped.

She turned back to finish her climb up the stairs and led him down the upstairs hallway to his bedroom, which was easy to find with the poster of Hugh Hefner's Girls Next Door on the door. He particularly liked Bridget. He even had an autographed picture of her. "I snuck outdoors and caught him, and made him come inside." She paused at the entrance to his bedroom. "Do you know what I made him do?"

He didn't really want to ask, but he knew he had to. "What?"

"I made him take all of his clothes off and be naked with me all evening. I wanted him to feel what it was like to be so naked and exposed, and have someone else look at, stare at, your naked parts." She leaned in closer to him, pressing her lacy brassiere, her soft breasts, against him, and said, as she softly ran her fingers up and down his shaft. "He even got a stiff willy just like you." As she opened the door she said, "Although, I do think yours is a bit bigger than his."

He smiled at the compliment, although he also realized that of course his would be bigger. His should actually be a lot bigger. Shouldn't it? He knew that his wasn't so large, but it wasn't so small, was it? Funny how a compliment could actually be perceived as a denigration.

She towed him into his bedroom, let go of the tow bar, and proceeded directly to his dresser. She searched some time through the drawers for suitable attire. He briefly contemplated relieving himself right there. He could perhaps pretend to be looking for slippers beneath the bed and then jerk off out of her sight. But, he knew he would unlikely get away with it, and that would be a very bad story to have to tell his mother. How many boys jerk off behind their babysitter? No, that wouldn't be too good. And, how embarrassing would it be to have his teacher catch him jerking off? He wondered what happened with Timmy Thompson. Did she eventually give him relief or just send him on his way? Perhaps he could ask her to finish the story?

Miss Landers then exclaimed, "Oh my, yes, here is a wonderful pair!" She turned around, and displayed for him, hanging from her hands, the bottoms to his old cowboy pj's. He hadn't worn them in years. He had in fact forgotten that they were still there. They must have been stuffed way down toward the bottom of the drawer. Why did she have to find that pair?

His face turned beet red. "Oh I don't think I can fit in those anymore. I don't wear them anymore."

"Oh pish posh. I'm sure they will fit. You're still quite little, you know."

Why must she remind him of that, particularly as he was standing there before her, naked and stiff? How many guys would like that? Being told that they were "quite little" as they stood before you displaying their big hard cock. Well, she wasn't actually referring to his cock, was she?

"Now you come over here and try these on."

"Yes ma'am," he glumly replied. So went the fantasy of the Hugh Hefner pajamas, he thought, as he walked over, his stiff dick swinging back and forth like an extended crane. He did at least use the excuse of needing to steady himself by resting a hand on her bare shoulder. His eyes were fixed on her bobbling boobs as he stepped into the pajama bottoms. Regrettably, they did still fit, at least good enough, although his cock was poking out the front pretty badly.

"Here, we can't have him stuffed inside like that." She unbuttoned his fly, reached inside, and pulled out his erection. "There, that's much better. That way if you have an accident you can squirt on the floor and not soil your pj's. Your mummy will appreciate that."

The thought of possibly being able to shoot off, shoot off anywhere, he didn't care at this point where, was encouraging. Although, he certainly wouldn't want Miss Landers to tell his mother about it. He knew he really should probably control himself. There was no way that he could cum without his mother becoming upset about it. How many mothers would be pleased that their son ejaculated in the presence of the babysitter? No, no, he had to control himself, as best he could in the presence of this so terribly erotic teacher.

"Now," she said, as she pulled out the matching top from the dresser drawer and handed it to him, "You get the top on, put on some slippers, and meet me in the living room. You were a very good boy to take your bath and we still have time for at least one TV show before it's beddie bye" As she was about to leave the bedroom she turned back to him and said, "Tommy, really, you look so cute in those pj's. I can see why you like them so much."

He was at a loss for words. He just looked at her dumbfounded as he pulled his arms into the soft cotton sleeves.

"And they're really quite fitting, you know. It's like you have your own personal rifle sticking out, all cocked and ready to shoot." With that she puckered her lips, blew him a kiss, and said, "If you keep your rifle good and hard, I'll have something special for you downstairs." She then turned and left, leaving him to ponder what she might have meant by that.

His fantasies ran amuck. There had to be only one meaning. She was going to have sex with him? No, no, she wouldn't do that. That was expecting way too much. Maybe she would just blow him? Imagine that, getting a blow job from his elementary school teacher. That would be so, so cool. As she had instructed, he put his hand on his cock and stroked it as he thought about it, keeping it good and hard. It hardly mattered that he was now eighteen. She was still very, very, very sexy, gorgeous as a matter of fact. She hardly looked any different than when he was in her class, and now she was dressed only in bra and panties, and very sexy ones at that. It would be so great, and it wouldn't even be wrong or illegal or anything. He was free to do what he wanted, as was she. Frankly, it would be great even if she hadn't been his teacher. Having a babysitter was turning out to be fantastic. He then suddenly felt the urge to cum. He had been jerking himself too hard. Actually, he realized that he could probably get away with jerking himself off right now. Shoot a good load and then get it hard again. But, she had said to keep it good and hard for his reward. If he jerked it off, he might not be able to get it hard again, at least not that quickly or not that well. But, surely he could, surely he could with the thought of what awaited him downstairs, he figured, as he resumed his stroking, thinking about Miss Landers's pretty soft red lips wrapped around his hard cock, her wet tongue washing him once again.

He let go. He better not take the chance. He better do exactly what she says. Even if he got hard again she might be able to figure out that he had jerked off. There would be the smell of cum on his cock, or his face would be flushed, or she would just simply be able to tell that he was hiding something from her. Teachers do have a way of telling when you are lying. He could tell that she didn't believe him when he denied ever peeking in her window. But, he hadn't seen anything. He probably should have said that, simply told the truth. It's always best to be honest with your teacher. His balls ached so bad as he slipped into a new pair of socks and ran down the stairs, his cock swinging back and forth like the crane was now in a storm.

He dashed to the living room to get his reward.

And, there she was, waiting for him, looking so pretty, standing there dressed only in her half cup brassiere, panties, nylons, and high heels. Her expression was rather shy and coy, with her hands clasped demurely behind her back, one knee cocked inward to slightly hide her cunnie, her face conveying a bit of discomfort at standing, posing like this for him in the middle of his parents' living room. Her breasts were rising and falling within their cups, revealing a nervous excitement. The curtains were closed to protect their privacy. The light from the television was casting a warm glow on her body. The sound was off, perhaps because they were not in fact going to watch television? Her modest smile turned into a big grin as she watched his waving hard-on proceed him down the hallway.

"Oh Tommy, such a good little boy. Your little boner is still there. I guess young boys can keep them up a pretty long time. I think your mother would be very proud of you."

He did not understand at all why his mother would be proud of that, nor was he expecting her to actually tell his mother about this. She certainly wasn't planning on telling her about this, was she? She couldn't be that naive. But, he wasn't going to think about, worry about, that right now. He had much more important plans. He wanted his reward. He wondered if he would be able to grasp hold of those big soft mounds. He wouldn't even care if she wouldn't let him under her brassiere. He wouldn't even care if she made him take care of himself. Well, at this point, that would be a pretty big disappointment. No, she would obviously do it for him.

"Well, come here, little man, and get your reward. I made you some milk and cookies!"

His heart fell. That was it? Milk and cookies?

"Well, I didn't actually make the cookies. I just got them out of a box. They're gingerbread cookies. I hope you like gingerbread. But, I guess you must because why else would your mother have them?"

Actually, these were his father's favorite cookies. His favorite was chocolate chip. His mother never did make those anymore. Sometimes it's hard to grow up.

"Now, let's sit down on the couch and watch TV together."

Miss Landers went over to the couch and patted a spot next to her. "Come on over, Tommy, and sit right here next to me. The milk and cookies are right here for you on the coffee table, although I guess it's a milk table right now." She giggled at her little joke.

She was smiling every so invitingly, but also now seemingly oblivious to the fact that she was wearing only her bra and panties, and that his cock was sticking out of his pj's.