Tommy Has a Babysitter

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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.