tagMatureTommy Has a Babysitter

Tommy Has a Babysitter

byCharles Petersunn©

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. This story is classified in the May/December (mature) genre. It also 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.

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"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.

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byCharles Petersunn© 30 comments/ 300682 views/ 119 favorites

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