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.
