Perverts 'R' Us

Alex and the Babysitter

By Anna Cater ( m/F, pt, 1st, cons )

I would be interested in hearing from other women who have a fetish for woman-boy love stories. Or send feedback to annacater@gmail.com

"Alex, the babysitter's here! Can you get the door for me?"

Alex ran downstairs, eager to obey his mother. He loved it when the babysitter came to watch him; he thought she was the prettiest girl he'd ever seen.

Lily had been his babysitter for a year, since he was eleven. She was a nineteen-year-old student with long auburn hair, big brown eyes, very fair clear skin, and did indeed have a sweet girlish face that was very pretty. She was tall enough that when she gave Alex a hug, his head was nestled on her breasts; he thought that made her the perfect height.

Lily gave Alex a lot of hugs. She was very affectionate, and when they sat watching television together, would kiss and cuddle him, and whisper in his ear how cute he was. One night he insisted on staying up late to watch a movie with her. Rather than argue with him (for Lily never got cross or raised her voice), she settled him down so that he was lying with his head on her chest. She began gently stroking his dark blond hair and nuzzling the nape of his neck, and within only a few minutes he had blissfully fallen asleep, so that Lily could carry him upstairs and put him to bed.

Alex also loved the games that he and Lily played together. When they played hide and seek, he would hide himself in the big closet in his room, or under the bed, or behind the heavy drapes in the living room. He would always feel very excited, and his heart would hammer in his chest almost painfully. He knew that Lily would find him in less than ten minutes because he always chose the same hiding places, but the thought of being found made him tense with anticipation.

The first time they played together he had hidden in his closet, curled up in the darkness with the door shut. When Lily found him, instead of pulling him out of his hiding spot with a cry of "Got you!" as he had expected, she pretended to be a wild animal that had caught him. She climbed into the closet with him and pretended to maul and eat him. He giggled and squealed as her fingers went all over him, and her mouth did as well. She pulled up his tee shirt and began licking and sucking at his chest and abdomen, then did the same thing on his thighs, going further and further up until her mouth and fingers were inside the leg of his shorts, right near his groin. He thought that was the most wonderful game ever invented, and never got tired of playing it.

But the most incredible thing that Lily had done with him he was not even sure had ever happened.

A few months ago his mother had had to go to the funeral of a distant cousin, and had asked Lily to watch Alex for the afternoon. He had been playing with a football in the back yard while Lily watched him from the window. He was showing off for her, and tried to run as fast as possible, kick the ball hard, and jump as high as he could to catch it. Every time he glanced over at Lily, she was watching him carefully, and would smile and wave to let him know she could see him. He imagined that when he came in, a conquering hero, she would praise him for his skill, and tell him he was the best football player she had ever seen.

With all the running, jumping, kicking, and trying to see if Lily was watching, it was hard for him to concentrate on what he was doing. He gave an impossibly high leap, twisted around to see if Lily had witnessed this feat, and then fell down hard on the ground, scraping his leg and hurting himself. As Lily rushed outside to him, Alex struggled not to cry with tears of pain and humiliation. Instead of being a conquering hero, Lily would think he was a stupid little kid who couldn't even play with a ball without falling over.

However, when Lily ran to him, her face was white; he had never seen her look so frightened. Even in his distress he noticed with interest that her breasts bounced when she ran.

"Alex, are you alright? Please be alright; I'll never forgive myself if there's something wrong with you."

She knelt beside him and cradled his head against her breast; she held him tight and began blindly kissing him all over his face as if that would somehow make him better. Alex was beginning to discover that although conquering heroes have all the glamour, there is a pleasure too in being a fallen warrior, and being ministered to by an adoring nurse on the battlefield.

Lily picked him up and carried him inside, laying him carefully on the living room sofa. She asked how much it hurt, and when he answered "A lot" because he liked seeing her so worried about him, she gave him a tablet to take with a glass of water.

"This will stop it hurting. It might make you feel a little drowsy, but I promise it won't put you to sleep."

Sure enough, the tablet took effect almost at once. The pain in his leg subsided and he felt extremely relaxed, as if on the verge of sleep. Yet his body did not go numb; on the contrary, his skin tingled slightly, and felt more sensitive than usual.

Lily began examining his leg carefully; he heard her mutter that there might be a sprain in the groin. Her hands gently stroked down the length of his leg to check for problems; she asked if it hurt and he shook his head.

Then Lily slid her hand inside the waistband of his shorts and began touching him on the soft skin between his thighs, as if to see whether he had sustained an injury there. Normally Alex would have squirmed and fidgeted, but now he was too drowsy and comfortable. He enjoyed the feeling of being stroked and remained quiet.

Lily fetched a sponge and a bowl of warm water, and began cleaning the mud and dried blood away from the scratch on his leg. She pulled his shorts off, and then his briefs, and began gently dabbing the damp sponge against his thighs and even around his penis. Alex could feel his penis start to stiffen; lately his penis seemed to have developed a mind of its own and begun getting hard for no reason at all that he could see. Lily smiled down at him, as if she thought he was quite clever for getting an erection all on his own. She started gently stroking his penis in an almost absent-minded way.

"Does that hurt you, sweetheart?" she asked him.

"No, it feels good," Alex murmured back sleepily.

Lily's hand rubbed his penis more and more firmly as he got harder and harder. By now he was so relaxed and drowsy that it almost seemed like something that was happening in a dream - and a dream he was very much enjoying. As Lily caressed him with both hands, she talked to him in a soft voice, telling him he was a gorgeous little boy and she loved touching him all over his body. She said that he had a very nice cock, that he should be proud of it, and that rubbing it made her feel very happy and excited inside.

"I think I should just give it a tiny little kiss to make you all better, don't you think?" she said playfully. She placed her lips against the tip of his penis and touched it quickly with her tongue. Alex felt a shiver of pleasure go right down his body. Lily licked the head of his penis all over as if it were an especially delicious ice cream, then put the entire thing in her mouth and began sucking on it. Alex couldn't believe how good it felt; it was so warm and moist and her tongue moved constantly against his penis as she sucked with more and more certainty. He started moaning gently with delight, waves of pleasure going through him until he thought he was going to burst.

Then it was as if he had burst, because something squirted out of the head of his penis into Lily's mouth. It was the first time he had ever cum, and he wondered vaguely if he might get into trouble for this. Instead she swallowed it all down, and then told him how yummy he tasted.

"You're a very good boy Alex," she said approvingly. He was glad she was so pleased with him. "But," she continued, "You mustn't tell anyone about this, okay? It has to stay our special little secret."

Alex nodded sleepily; he really thought he was about to drop off properly at last. He was barely aware of Lily carrying him upstairs, putting his pajamas on, and then popping him into bed.

"Remember it's a secret," she whispered as she kissed him tenderly on the forehead.

"Am I still dreaming?" said Alex groggily.

"That's right sweetie, it's just a dream. Just a beautiful dream you'll forget all about when you wake up."

Then his eyes closed, and Alex never heard her open the bedroom door and leave.

Afterwards, Alex wasn't sure whether Lily really had touched and kissed him the way he remembered. He was at an age where dreams, fantasy, and reality were still sometimes hard to distinguish from one another; it was only a few years since he stopped believing in Santa Claus, and only a year or two longer since he stopped being frightened of the bogey man.

After that afternoon with Lily, he began having dreams about her where she touched his penis and sucked at it lovingly; sometimes she would run with her breasts bouncing; other times she just petted him and told him he was a good boy. He sometimes woke from these dreams all sticky. After a while, it was hard to tell them apart from his memories, and he wondered whether the afternoon with Lily had just been the first of those dreams.

He thought that Lily herself might give him a clue through her behaviour, but she never referred to it and treated him with her usual cheerful friendliness. If anything, she had grown slightly more distant. Once he had climbed on her lap and put his arms around her neck, and she had gently pushed him off and told him he was getting too big a boy to sit on her lap any more. They hadn't played hide and seek since then, and when he had asked, she just said he was getting too old to play kiddy games now.

It had always been his dearest wish to be big and grown up enough so that Lily would treat him as an equal and take him seriously; now he wondered gloomily if getting older was all it was cracked up to be.

******

When Alex opened the door to let Lily in, the first thing she did was give him a hug and a kiss on the cheek as usual. She looked him over and told him how tall he was growing, and what a handsome boy he was. In fact, Lily privately thought that Alex was the loveliest boy she had ever seen. He had a cute, snub-nosed, urchin face lightly scattered with freckles, hazel eyes rimmed with long dark lashes, and dark blond hair to his collar with a fringe that he was always pushing away distractedly. She loved his slim athletic body that was so beautifully made, everything so perfectly proportioned, and slender and light enough that she could pick him up and carry him around in her arms if she wanted to.

Lily had been careful to back off a little from Alex in the months since she had fulfilled one of her best-loved fantasies and sucked on his sweet little penis; she could still remember how delicious and creamy his cum had tasted, and her mouth watered at the thought. She had seen him looking at her wistfully since then, pleading with her to touch him again and give him the attention he craved. She thought he now seemed almost desperate for her hands to stroke him all over, and would be grateful for even the smallest gesture from her.

If Alex had only known, it had been just as hard for her to refrain from caressing him. She ached to stroke and kiss him; she missed their games where she would playfully lick his nipples and nibble at his thighs; she wanted him to cuddle up to her so she could hold him close and smell his fresh, boyish aroma.

This evening after supper when they were watching television together, she finally decided that she couldn't stand it any more. She drew Alex toward her and stroked his hair, giving him a soft little kiss on the forehead. He snuggled up delightedly, hardly believing his luck; Lily was finally giving him the contact he desired. When her hands slipped inside his shirt and began running along his sides, he shivered with pleasure. Lily marveled at how responsive he was; the lightest touch had an effect on his body.

The program they were watching was a drama for teens set in a high school rather improbably devoted to surf life saving. Alex's mother had declared it to be utter trash, and called it "Baywatch For Kids". They felt a naughty sense of satisfaction in disregarding her wishes, and thoroughly enjoyed giggling together at the ridiculous plotlines and stilted dialogue. Sometimes Lily would tickle Alex's tummy to make him squirm and wriggle against her so that he would laugh even harder.

The television drama revolved around a large group of good-looking teenagers with made-up sounding names who spent their time having angst-ridden conversations dressed in bathing suits or skimpy outfits in between saving random swimmers and each other in dramatic beach rescues. Lily liked watching the younger boys, and she imagined that Alex was getting a good look at the beautiful girls, who all had perfect figures, long hair, tanned skin, and tiny little bikinis.

"Which girl is your favourite?" she asked him when the 'trash' was over.

"Shayna," he confessed, referring to a petite brunette whose full breasts were barely contained by her even-skimpier-than-usual blue bikini. "She's the prettiest. But," he went on confidingly, "none of them are as pretty as you are, Lily."

"You are so sweet to say that," said Lily, genuinely touched. "And you are the cutest boy in the world."

She put her arms around him, and Alex eagerly offered her his lips. She hesitated, and then brushed her lips against his, but Alex opened his soft mouth, inviting her to kiss him properly, the way people did in movies. Lily couldn't resist; he tasted so good and her tongue slid against his seductively for just a few moments.

Then she broke away, and said with a slight tremor in her voice, "Come on Alex, it's time for your bath now."

She led him upstairs and filled the tub with warm water, adding lots of bubble bath at his insistence. Then she unbuttoned his shirt and removed it, then unzipped his denim shorts for him to step out of it, finally pulling down his briefs. She thought to herself that Alex looked beautiful naked, but out loud she just told him to hop into the bath. He hopped on one leg; an old joke that always made her laugh and slap his bare buttocks in mock annoyance.

While Alex lay back in the tub, Lily took the sponge and began slowly soaping him all over his body; down his arms and legs, his chest and stomach, but paying particular attention to the area between his thighs and around his penis. Lily was wearing a short cotton sundress, and as she bent over the tub, Alex could see the tops of her breasts, jiggling slightly with the movement of her arm. To his embarrassment, his penis began to get hard, and he tried to hide it under his hand.

"It's okay, Alex," Lily said. "It's normal for a boy your age to get hard when he sees or thinks of something sexy. It's nothing to be ashamed of; in fact, you should be proud because you've got a lovely cock and I like looking at it. What were you thinking about, anyway?" she asked casually.

"You," said Alex naively. "I can see your boobies when you bend over."

Alex was so young that he blurted out whatever was on his mind, and she thought that was adorable. It was such a welcome contrast to boys her age who were so anxious to look and sound cool. Lily found them tiresome.

"You're full of compliments tonight, aren't you?" she smiled.

She picked up a bottle of lavender-scented baby oil and poured some into the bath, and then a little onto her hand. She began gently massaging the oil into Alex's penis, and then started stroking and rubbing it along the shaft. Alex gave a little sigh of pleasure; Lily knew just when to apply more pressure, and when to make her touch lighter; sometimes just running the tips of her fingers along his penis with a feather-light touch and sometimes gripping him firmly with long, even strokes. She didn't neglect to rub a little oil very softly into his balls, and to cup them in her hand as she continued touching the head of his penis.

She made sure he could see her breasts jiggling while she rubbed him, letting them almost fall out of her dress. It wasn't long before he gave a little moan and his cum spurted out into the water. Lily gave him a quick kiss on the lips, and told him he was very clever for being able to cum like that at such a young age.

Then she helped him out of the bath, wrapped him in a big fluffy towel, and began carefully drying his naked body, gently patting him dry because she knew he was now feeling extra sensitive. She helped him put on his pajamas, and then led him across the hall into his bedroom, pulling back the sheets and tucking him into bed. She kissed him on the cheek and told him she would come and check on him in a while to see if he was asleep, leaving a dim nightlight on in the meantime.

Half an hour later, she tiptoed into the room to find Alex lying on his back, but still apparently wide-awake. Lily went and sat on the edge of the bed, and asked him if anything was wrong.

"No," said Alex. "Sometimes I just have trouble getting to sleep."

Lily thought he looked irresistible, lying there in his little-boy bed. She began stroking his body through his pajamas, and then slipped her hand inside his pants to find he already had another erection.

"I think I can see the problem," she whispered. "You have a hardon, and it's difficult to get to sleep when you're horny, isn't it? Does this happen a lot?"

"Sometimes," admitted Alex, a little reluctantly. He wondered whether Lily would think he was a freak who couldn't control his own penis.

"Do you ever … touch yourself when you get horny at night?" she questioned further.

"Umm, yeah, sometimes. But I don't know how to do it properly; the boys at school said to do it with your hand, but it doesn't feel all that good really. Not like when you did it in the bath."

Lily stroked his hair and gave him a kiss, while gently rubbing his stiff little cock.

"You just need practice, that's all," she reassured him. "You'll get the hang of it one day."

"Could you … could you show me again?" pleaded Alex, looking up at her with big eyes. "Or … you know … could you put it in your mouth like you did before?" He held his breath to see if she would tell him at last that it really happened, that it wasn't all in his imagination.

"Oh, so you know that wasn't a dream," said Lily thoughtfully.

Alex had a moment of panic, thinking that Lily was about to stop touching him, that she would get offended and leave and never come back to touch him again. He didn't think he could bear it. But he had nothing to worry about; Lily loved caressing him far too much for that to happen.

"I'll show you something even better," she whispered back. She quickly pulled her panties down from under her dress and stepped out of them, leaving them on the floor by the bed. Then she got Alex to remove his pajama pants completely, and unable to resist, gave his penis a quick little suck; it tasted very sweet and clean after his bath.

Alex was disappointed that she stopped so soon, but she then climbed into the bed and lay on top of him, kissing him passionately while she did so. Alex kissed her back, excited to have Lily so close to him, lying belly to belly. Lily was already wet and ready for him; she really couldn't have waited another minute for this.

She gently guided his penis inside her; she thrilled at the touch of his smooth cock sliding into her so easily. She rubbed her clit against him and began panting with desire; she had always known she would love being with a young boy, but it was even better than she had imagined. Alex was so amazingly hard, and being on top, she could look down into his boyish face, lit up with innocent pleasure because his beloved babysitter was sitting on his cock. He had the same expression as when he opened his present from her at his birthday party.

As her vaginal muscles began contracting against his penis, Alex got even harder inside her. Having his cock inside a real grown up woman was something he had never dared picture in his wildest dreams, but he was loving every moment of feeling her so warm and moist around his penis; it felt as if she were sucking at him in the same way her mouth did. Her breasts were right near his face, and he could see them bouncing in front of him while she fucked him.

The whole time he was inside her, she was telling him how good and hard he felt, how much she loved his gorgeous cock, how long she had wanted to fuck him. Lily could feel her orgasm building inside her, and she began fucking Alex harder and faster, until he thought he was in heaven. When they came she felt as she had exploded with pleasure, and Alex felt the most wonderful sense of release; this was better than the bath, even better than being sucked off. He was sure it was better than anything the other boys at school had experienced.

"You're the most beautiful fuck, Alex," said Lily, now lying beside him, kissing him, and holding him close in her arms. "Did you like that as well?"

"Can we do it again real soon?" asked Alex hopefully.

Lily gave a little laugh at his eagerness. "Yes we can," she promised. "And I'll show you lots of other fun stuff as well - things you'll really go crazy for."

Alex looked more than satisfied at this suggestion, and snuggled into his blankets ready to sleep.

"Oh yeah - and I know it has to be our special secret and everything," he recited drowsily.

"Good boy, you remembered," Lily said approvingly. She pulled his pajama pants back on, then kissed him good night and switched off the nightlight. Alex was sound asleep before she had left the room.

Lily washed herself carefully in the bathroom and put on her panties before going downstairs, thinking of the illicit pleasure of being with Alex, and wondering how soon before they would get another opportunity for it.

It wasn't long before Alex's mother came home. The first thing she did was check on Alex, and saw he was fast asleep; he didn't stir even when she gave him a peck on the cheek.

"Well you're a miracle worker, Lily," she said when she came downstairs. "He never goes to sleep like that normally; he seems to have trouble settling down lately. What's your secret?"

"Lavender baby oil in the bath water," said Lily promptly. She smiled inwardly when she thought what her real 'secret' was.

"I'll have to try that out," said Alex's mother, and then she paid Lily, thinking she was worth her weight her gold; she was so reliable and Alex seemed to adore her.

"You've got a real knack with children," she said admiringly. "As if you really love them and understand what they need. I guess that comes from your studies though, right?"

"No, I think it just comes naturally to me," replied Lily. "But I'm sure it helps make my training easier. Nature and nurture, you know."

"Well, you're going to make a great child psychologist, I bet."

"Thanks," said Lily. "That means a lot coming from a mother."

The two women waved goodbye as Lily got into her battered little car. She drove away, thinking of the long career she had in front of her working with children; she hoped at least some of them would be as cute and easy to seduce as Alex.