Tommy Has a Babysitter

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"We can snuggle up together on the couch, Tommy." Well, that sounded more inviting than just having milk and cookies.

"Okay, okay," he said, and proceeded over to her, now feeling very self-conscious about his erection. It was like she wasn't even noticing it, like it didn't mean anything at all. Imagine exposing yourself to a pretty woman, dressed in her panties and bra. Your big hard cock is all poking out, and she acts like it isn't even there! He found himself wanting her to at least tease him about it. Sometimes it's much worse to be ignored than to be teased.

"Wonderful. It will be so nice to be able to tell your mummy what a good boy you have been."

"Yes, ma'am," he replied as he sat down on the couch, next to her, his dick poking up out of his cowboy pj's. She used the remote to turn on the sound. "I found this wonderful show. I'm sorry but I couldn't find any cartoons this late at night, but I think you will like this. It's very educational."

Yes it was. It was some documentary on all 154 of Shakespeare's sonnets. It would have been difficult for Miss Landers to have picked a more boring show if she had tried, although he wondered frankly if perhaps she had tried to find the worst possible show. He would even have preferred a cartoon, although that would have been more embarrassing than this.

The show did though at least help him lose his erection. It was obviously not going to be put into any good use and so he would prefer that it just slip quietly away into the night. His balls couldn't take much more flirtation, and he would handle it, literally, when he got to bed, thinking about their time in the bathroom, at least when she was cleaning off the front of him, but, then again, the memory of her cleaning his behind was now rather appealing, particularly if he imagined her reaching around, pressing her breasts against his butt, stroking him as she worked her finger in and out of his ass. Wait, thinking about this was not helping him lose his erection. He picked up a cookie and his glass of milk and settled back into the couch, looking forward to the fact his dick would soon soften and disappear into his pj bottoms.

Miss Landers though didn't help the cause. She slid over toward him on the couch so that they were pressing up against each other. "Now, don't be a stranger, Tommy. You snuggle right up against me." She even wrapped her arm around his shoulder and pulled him toward her, pressing the side of his face into her brassiere, into her large full breast.

It was a little awkward eating a cookie and sipping milk while his head was resting against a boob, but this was a sacrifice he was willing to make. It felt like such a nice big soft pillow tucked into a very lacy pillow case. He sighed deeply with satisfaction, munching on the tasty cookie (even though it wasn't his favorite, he would have to admit to really liking gingerbread), sipping the cool refreshing milk, and snuggling up against a full soft breast. This was kind of nice.

His penis though softened despite the contact with her breast. He could thank the power of the Discovery channel for that. The show was so boring. It just seemed to drone on and on and on. Why did he have to write so many sonnets? In addition, the room was incredibly warm. Miss Landers apparently turned the heat up, quite literally so. Couldn't blame her for that, as otherwise it would probably have been a bit chilly for her, in her present state of undress. He got through about half of the show, and half the cookies and milk, and began to openly yawn.

"Oh, I'm sorry, Tommy. This is perhaps too much of a grown-up show for you, isn't it. I should have realized that. Here," she said, taking his milk from his hand and drawing his head down into her lap. "You can rest your head on my lap. If you need to go sleepy bye, you just go ahead."

He was indeed feeling tired, perhaps it was the milk as well as the show. A glass of milk had always helped him to go sleep as a little boy. He snuggled into her lap, but quickly appreciated that his cheek was now lying right across her bare womanly thighs, so silky smooth in her nylons. He turned his face away from the television, ostensibly to find a more comfortable position, but more truthfully to turn toward her panties. His eyes, and his lips, were now just an inch, or less, away from the gossamer lace. His eyes widened with delight at such a very close, so intimate, appraisal of the womanly cunt of Miss Landers. His penis stirred as he carefully scrutinized the outline of her mound and, more importantly, her feminine lips, appearing through the sheer, diaphanous fabric, and he breathed in deeply her scent. It was such a lovely, earthy aroma.

He suddenly turned his head up, wondering if she was noticing that he wasn't trying to sleep at all, but he quickly discovered that she probably couldn't see that his eyes were wide open, as he couldn't see her eyes at all. All that he could see were these two towering lacy half globes seeming to hang precariously over his face. They looked big before, but they were now even more terribly impressive, just inches above his eyes.

He lost all interest in falling asleep. How can you sleep when you're lying beneath two large snowy hillocks hanging out over your head? He smiled at the thought of being smothered by such a delicious avalanche of squishy flesh.

"Goodness, Tommy," Miss Landers said, leaning forward a bit so that she could look past her tits down to his face looking up at her in her lap, "The little rascal slipped back inside, didn't he." She leaned back against the couch, again out of eyesight, while she slipped her fingers into the flap of his pj bottoms and once again grasped hold of his penis. He gasped with surprise, and pleasure. Any intention of sleeping now was lost entirely. "Well, I'll keep an eye on him for you. You just go sleepy bye. Maybe he'll have some happy dreams if I play with him."

His penis very quickly swelled with her feminine fondling, climbing out of his pj's like a snake emerging from its nest, rapidly becoming stiff and stout. "Well, goodness gracious, there he is! All pleased and proud." She danced her fingers up and down its length, and then softly caressed the tip of his crown with the tip of her index finger. "I think little boys' penises are so terribly cute." She leaned back over her breasts again and asked, looking him in the eye, "Have you shown your little man to a girl, Tommy?"

Well, of course he had. He really wasn't a little boy, you know. "Yea, sure, sure, plenty of times."

Miss Landers gave his erection a sharp flick with her middle finger, snapping it off her thumb so the hard fingernail hit sharply against the soft, sensitive head.

"Yeow!" he screeched, both in shock and pain.

"Little boys should not lie to their babysitters, Tommy. Now you tell Miss Landers the truth, otherwise, she will send you to bed and no more pee-pee play."

He wouldn't mind going to bed, and particularly he wouldn't mind if 'pee-pee play,' meant additional nasty painful flicks. Plus, he could then finally take care of himself, get the relief he so desperately wanted, needed. His balls felt like they were beginning to turn blue. But, what young man would, could, deny himself the more sensual touch of feminine fingers on his erect cock, even if it came at a price. No price that one could pay would be too high, at least when you were so aroused, so in need of relief. He could play along in this game of make believe, if that's what was required. "Okay, okay, no, no, I haven't had a girl see it yet."

Miss Landers smiled in triumph. "Well, of course not." She sat back in the couch and resumed her soft caressing, much to Tom's pleasure, whose eyes half-closed in sweet bliss at the feel of her tender fingers caressing his dick as he gazed up at the two full moons hanging above him, his head resting on the silky thighs of Miss Landers. "You're a good little boy and you wouldn't go around showing girls your dirty, naughty thing." It might be a perverse little play, but it sure felt good.

She grasped her fingers fully around the shaft and stroked him up and down. They could both hear the squishing noises of precum lubricating beneath his foreskin as it slid on and off the head of his cock. "Oh my goodness, Tommy. I just realized that mine would then be the first girl's fingers that have ever touched your wee-wee!"

"Yes ma'am," he groaned, feeling himself getting close once again.

"It must be kind of fun having your teacher stroke her hand up and down your little boy cock."

"Yes, yes, it is," and if she kept doing that, she would soon find out how much fun it really was.

"Did you ever think that Miss Landers would stroke your penis like this, Tommy?"

"No, no, not at all," he gasped.

"Well, I just hope you don't tell all your friends." She briefly stopped, gripped him hard, and leaned back over her breasts to speak to him directly. "And certainly don't tell the principal, Mr. Beaumont!" She leaned back against the couch. "I don't think he would understand one bit."

"No, ma'am," he softly replied. "No, he wouldn't." Either did he, really. For a moment Tom wondered if Miss Landers was in fact psychotic, really believing that he was twelve years old again, but when she began to softly caress the underside of his dick, just behind the crown, he felt reassured. No crazy woman could be so sensual, so erotic.

"Oh my," she said, feeling his cock twitch and swell in her hand. She suddenly let go of it. "You were just about ready to squirt, weren't you, Tommy."

"Oh yes, yes, yes I was," he replied breathlessly, shoving his pelvis up in the air, trying to get her to grab hold of it again.

She did grab hold of it. "Here, let me help you with that." She did, but not in the way he was expecting, or hoping. She wrapped her thumb and index finger tightly around the stem, just below the crown, and squeezed hard. "This will relax you." It didn't relax him. It was in fact quite uncomfortable, even a bit mildly painful. But, it did take away his urge to ejaculate.

He squirmed a bit but she kept squeezing until his erection began to dissipate. "There we go. All better now. We can't have boys getting the hiccups in class, can we. You just remember that yourself. When you think you're going to squirt in a class, just give it a good squeeze."

He began to think she might be crazy again. But, she then giggled, tipping her hand that she was in fact having considerable fun playing this game. Perhaps he should just stand up and demand that they stop. It was pretty weird. Still, a good sex game isn't necessarily logical or sensible. "Yes, ma'am, thanks, yea, I will."

"That's a good boy. You wouldn't want to squirt your dirty juice all over your new, fresh pj's would you?"

He slid his head down her nylons to look up at her, past her thrusting breasts. "It would be okay. I wouldn't mind. I'll even wash them myself."

"Oh no. That's very nice of you to offer, Tommy," she replied, as she ran her nails down along his taut stem, sensually scratching the sensitive skin, and then cupped his balls with the tips of her fingers, lightly bouncing them up and down, "I wouldn't be a good babysitter if I had you do that. My goodness, though, it does feel like you have lots of boy juice in there."

"Yes, ma'am," he gasped.

"Do you tend to ejaculate a lot of semen, Tommy?"

He thought he did. "Yes, yea, I do. Do you want to see me do it?" By playing along perhaps he could in fact get relief?

"Tommy, want a naughty thing to say to your sitter?" She let go of his nuts and shook her finger disapprovingly in his face. "Do you offer to spurt and squirt for all of your babysitters?"

"Oh no, no ma'am. Never before at all. Honest!" That certainly was true. "This would be the first time." Perhaps appealing to the first time would help. She seemed to like the fantasy that she would be his first time.

She did appear to contemplate the option. She returned her hand to his cock, this time pressing the head of his swollen bulb into the palm of her hand and massaging the tip around and around in her palm while she fondled and tickled the stem with her fingers. "Well, maybe you shouldn't go to sleep like this." She shifted her fingers back down to his balls. "It might not be healthy for a little boy to go to sleep with his testicles all stuffed up." She leaned forward again to speak to him directly. "You should always blow your nose, you know, before you go to bed. It's not good to be all stuffed up." She leaned back. "But, oh my," she said, noticing that another show was beginning to start on the Discovery channel. "It is now your bedtime. Goodness, how time flies. Yes, well, off to bed with you," she instructed, lightly tapping his hard dick, like she was tapping him on the shoulder to encourage him. "You run along. You know how upset your mother would be if she knew you stayed up past your bedtime."

Tom moaned as he crawled off her lap and off the couch. His cock was so, so hard. He aimed it right at her as he said. "Can't I stay up for just a little longer. I won't tell mother." He wondered, 'Can't she see how much pain I'm in, how much I need relief?'

"Tommy, you've been a very good boy all evening, don't spoil it now. You just run along, and if you go right to bed with no further complaint, I'll come upstairs and give you a very nice reward."

He didn't waste a second. "Okay, okay. I'll do it!" He then turned and dashed off, his cock again waving in the air before him, like a fishing pole in a storm, bobbing and weaving with the rocking of the boat.

She yelled after him, "Be sure to brush your teeth!" She cleaned up the coffee table, and took the glass of milk and cookies back to the kitchen.

He did indeed brush his teeth, although it was a little odd to be doing so with a hard-on sticking out of his pj's, all the while wondering what the reward would be. It couldn't be another snack. His mother had made it very clear that he was not to have any cookies in bed. And, they had just been talking about getting relief. It had to be something sexual. He couldn't belief his good luck. It had been a pretty tough evening. In fact, really tough. But, it appeared that it was going to have a very happy ending. He was ecstatic.

He seriously doubted that she would actually have sex with him. Imagine actually fucking your pretty elementary school teacher. Now, that was a boyhood fantasy coming true. But, it wouldn't be that good. A blow job would be just as fantastic, and she did say something about blowing his nose. Imagine having those luscious lips that instructed him for so long, that sweetly nurtured him as a boy, that lectured and scolded him so often, now wrapped around his cock, her pretty face embedded in his crotch, and then shooting off his load, filling her mouth up with all his cum, perhaps even popping out at the last minute and covering her face with his cum? His balls were broiling for relief.

When he finished brushing his teeth he ran up the stairs in a mad dash. Never before was he more anxious to go to bed. He literally leaped into bed, pulled down the covers, and got underneath, but then realized his mistake and pulled the covers back down. He positioned his stiff cock so that it would be very evident and clear when she entered the room.

He could hear her steps as she came up the stairs. His heart was beating so fast. He felt like reaching for his cock, stroking it. Yes, that would be good, to be jerking off when she entered the room. She couldn't ignore that. But, he knew he was himself on the verge of cumming already. It would be climactic but also rather anticlimactic to shoot his load all over himself just as she entered the room and, even if he didn't cum, he wouldn't be surprised if she acted all offended by what he was doing. She got pretty upset the last time he put his hand on it. Most babysitters would probably be rather upset, to say the least, by the sight of the boy openly masturbating in front of her. A moment of panic overwhelmed him, perhaps he shouldn't even have it sticking out! She obviously knew already what reward she was going to provide him. It was already decided. All he could do now was to mess it up by doing something stupid or offensive, like waving his erection at her. As she rounded the door to enter his bedroom he quickly grabbed the bedspread and covered himself up.

"Oh Tommy, what a good little boy you are. All tucked in."

"Yes, ma'am." Whew. That was close.

"Well, scoot over then and let me get in beside you. I have a nice surprise for you."

Tom was bursting with anticipation, as well as with a lot of stifled, pent-up cum. He slid over to make room for his teacher, his eyes naturally following the wiggling of her boobs as she stepped out of her heels and got into bed beside him, sliding as well under the covers. It was a little disappointing to have her lower half now concealed by the blankets, but also rather tantalizing to realize that he was in fact sharing a bed with the pretty Miss Landers, and she in her undies. Besides, the upper half was still outside, and it was a pretty darn good half. The glass was clearly half full rather than half empty.

"Isn't this comfy cozy?"

"Yes, ma'am."

"Now, I have a very lovely bedtime story for you. Won't that be wonderful?"

"Is that the surprise?"

"Yes, of course, sweetie! What did you think it was going to be? A new toy or something? Such a silly boy."

Tom sighed in disappointment, not disguising the fact that he was indeed hoping for something else. He wondered if perhaps he should have been outside of the covers. Clearly he didn't have anything to lose. And, what was she going to read to him? Probably some Hardy Boys story or something. Maybe even worse. Maybe it would even be a child's fairy tale. At least please be a very, very short story.

"Now, you scrunch over close to me. It's kind of a long story."

Oh man! When will this end?

"Mr. Petersunn does tend to write long stories but, you know, Tommy, I prefer them that way. I like how they slowly build up, flirting with the ending, slowly building up to the climactic ending."

His climax would come after the story, and he was indeed in a hurry to get there.

"I'm going to read to you the story about how 'Chrissie and Michael Lead the Way.'"

'Great,' he thought. 'It is going to be some children's story.'

"It's from a very nice website, Literotica. It's a wonderful story about Chrissie and Michael, who must go to college one day without any clothes on whatsoever."

'What!?' His ears perked up.

"Now, Tommy, I must first tell you that all of the persons in this story are eighteen years old, just like you. It would be very wrong if one of them one was not, wouldn't it?"

"Oh yes, Miss Landers." He breathed a deep sigh of relief. It was so nice to hear her finally acknowledge his age. Thank goodness she wasn't actually delusional. On the other hand, oddly enough, hearing her acknowledge that she knew his real age kind of diminished the playful pretending, at least just a little bit.

She began to read to him the story of Chrissie and Michael. It was not a children's story. In fact, it was pretty interesting: how Michael had to masturbate in front of a human figure drawing class, squirting his stuff all over the floor, and then there was the prostate exam that all the pretty coed nurses gave him in another class. He particularly liked the part where Michael wound up ejaculating all over Beth's face.

Tom was understandably fascinated, and aroused. "Do they really do things like that?"

"Oh yes, dear," Miss Landers replied. "This is actually a true story about Abberville College. You might consider applying there."

Tom had indeed heard of Abberville College. He was actually thinking of going to Livingston College, but this sounded a whole lot better. "Wow, I can't believe they actually go to classes naked."