tagMatureMale Babysitter

Male Babysitter


"I'm worried about my boys, Marge," Gina Smith confessed to her best friend after church one day.

"Why?" Marge replied. "You're a great mother, and your boys seem happy and they do ok in school, right?"

"I know... maybe I'm over thinking, but I feel like they need more of a male influence in their lives. Clancy never was around that much right after the divorce, and he rarely calls now than he and Kimmy have moved to California," Gina said, practically spitting out the name of her ex-husband's new, younger wife.

"Have you been dating much?" Marge asked.

"No. A little, but nothing has gone anywhere. It's hard to find a good man at 38. I realize that it may be unfair, being a divorcée myself, but a lot of middle aged divorced men give me the creeps. I feel like a lot of these guys are still on the market for a reason," Gina explained.

Marge nodded. "I'm sure you'll find a diamond in the rough if you're patient."

"That's easy for you to say, still happily married to your high school sweetheart. But, regardless of me and my male needs, I don't want to thrust being a good role model for my boys on a potential boyfriend, at least not right away. I want something a bit more... organic than that."

"What about a male babysitter?"

"I've thought of that, but I see these teenage boys, and I can't imagine them being responsible enough. Hell, sometimes I wonder if the teenage girls I've had are really up to it. I guess I was lucky with Madison, but now that she's a junior she doesn't have much time anymore," Gina said.

Marge thought for a moment. "I think I can kill two birds with one stone. You know my younger son, Keith?"

"The one who just finished college?" Gina asked.

"Yes. He still hasn't found a job yet. It's a really tough economy right now. He's living at home with me. You'd have to ask him yourself, but I'm sure he wouldn't mind helping you out, and making a little money in the process," Marge suggested.

"Do you think he'd do it? I can't pay him anymore than I pay the girls, $15 an hour."

"When you have no income, an extra 40 or 50 dollars a week goes a long way. I'll talk to him, and have him call you, ok?" Marge said. Gina and Marge hugged goodbye and walked to their cars.

Keith called a couple days later. "Hi Mrs. Smith, this is Keith."

"Hello Keith! I was expecting your call. And we're both adults, please call me Gina. Mrs. Smith is my mother-in-law. And technically it's Ms. Smith."

"Oh, well, right," Keith replied. "So, Gina, my mom says you'd like me to watch your kids on Friday night. What time do you want me to come over?"

"The girls plan to meet up around 8, but I'd like the boys to get some time to get used to you before I leave. Is 6 o'clock ok? I'll pay you for the whole time you're here, of course."

"That sounds great," Keith agreed.

Gina was surprised how deep Keith's voice was. She remembered him as a skinny teenager at church with a crackling voice. He'd stopped going with Marge once he started high school, and she didn't recall ever seeing him after that.

Gina was almost stunned by the young man who arrived at her doorstep promptly at 6:00 Friday evening. He was tall and broad shouldered, with a hint of a 5 o'clock shadow on his face. Still, she recognized Keith's dark brown eyes and dimpled smile almost immediately.

"I can't thank you enough. I don't know if Marge told you, but I'm worried my sons don't have enough of a male influence on them ever since, you know, the divorce. BRANDON, PAUL, come in here please!" Gina called out. Two boys appeared one a few years older than the other, but both with red hair that matched their mother's.

"Brandon, Paul, this is Keith. He's going to take care of you tonight while Mommy goes out, ok?" The boys nodded, sizing up their new sitter silently.

"Hey guys," Keith said, bending down on one knee to speak to them at their level. "Are you two glad it's Friday and there's no school tomorrow?"

"No school!" Paul, the younger of the boys cried out with a gleeful laugh. Brandon simply nodded shyly.

Gina, meanwhile, was admiring Keith's fit young body, especially his ass, which was slightly outthrust in his prone position. 'He'd never look at me, but there's nothing wrong with me appreciating him,' she thought to herself.

"Why don't you men go play in the living room? I'm going to go get ready," Gina said. The boys ran off, and Keith smiled at her briefly before trailing after them.

Gina went upstairs and stepped into the shower. She took the time to shave her legs and trim her pubic hair to a close patch. It was a habit Clancy had gotten her started on, and one she'd maintained despite the lack of male attention in her life. 'You should always be prepared, just in case,' she thought to herself.

Gina's outfit was all about "just in case", especially the lacy bra and thong underwear set she wore under her dress. She didn't expect any guy to see it that night, but it still felt nice to dress up sexy, even if just for herself. That, and on the off chance she did meet an eligible man, she didn't want to be caught in tattered old undies.

Gina was done with her make-up before seven, and went downstairs to check on Keith and the boys. She saw that they were engrossed in a Playstation game. She overheard Keith teaching Brandon something about how to beat a certain monster. It was like a foreign language to her, which made her smile all the more at Keith's actions.

"My ride should be here soon," Gina said, announcing her presence to the young men. Her sons remained engrossed in the game, but Keith turned to face her. Gina was flattered when his eyes popped open a little at the sight of her.

"You look great!" he exclaimed. "You're going to have to beat the men off with a stick tonight!"

"You flatter me," Gina replied with a smile. "But thank you. I shouldn't be too late tonight. The boys have already eaten, but help yourself to anything in the fridge or pantry. Don't let the boys eat too many snacks. Their bedtime is ten. It's a Friday, so it's ok if they stay up a little later than that, but they should be in bed with the lights off by 10:30. I should be home a little after midnight."

"10:30. Got it," Keith replied.

"Call your mother if there are any problems. Hell, you're 22 right? You can probably handle any emergency on your own. Sorry, I'm used to dealing with 14 and 15 year old girls."

"It's ok; it's natural to worry about your sons, especially with a new caregiver. I've watched kids before. Not recently, but they'll be fine. Don't worry; we'll have a great time. Just enjoy yourself," he said with a wink.

"Oh, I will. A couple of my friends tend to get a little crazy," she said with a wink. "Boys, you be good and go to bed on time. Have fun, and thanks again Keith," she said. There was a knock on the door, and Gina left for the night with her friend.

Gina had a great time at the wine bar, although there were no unattached men there who caught her eye. Still, she loved chatting with her friends, and after ordering a bottle of wine and drinking half of it by herself, she had a nice buzz going.

The group dispersed around midnight and Gina arrived at her front door shortly thereafter, the unfinished half of her Pino Noir bottle in hand. Most of the lights were off but she heard the sound of the TV in the family room. It turned off a moment after she stepped inside, and Keith appeared shortly thereafter.

"Did you have a good time?" Keith asked, smiling at the bottle in the older woman's hand.

"I did. How were the boys?" Gina asked, sitting down to remove her uncomfortable shoes.

"They were great. I fed them some ice cream, and let them stay up until 10:30. Paul fell asleep on the couch watching Finding Nemo. I had to convince Brandon it was time for bed at the end of the movie. He wanted to wait up for you. Luckily he didn't take too much convincing."

"That's good. What have you done since then? And do you want to help me kill this wine bottle?" she asked with a conspiratorial smile.

"I've just been watching TV, and I could have a glass. But I'm off the clock now. As of this moment I'm on my own time."

"Sounds like a deal," Gina said. She fetched two glasses from the cupboard and divided the remainder of the bottle between them.

Gina told Keith about her friends, and some of the topics they had discussed that night. She enjoyed sharing the salacious details of one of her friend's affairs. It was with a younger man she'd met at a bookstore, and while Gina didn't fully approve, she had to admit a bit of jealousy at her friend's sexual adventure.

"This is nice, you know, just talking to a guy who is more than 10 years old. I love my boys, but we can't exactly discuss the political ramifications of cartoon characters."

"I totally understand. I like talking with you too, Gina."

"God the girls at school must have gone nuts for you. Beautiful eyes, great smile, tall too," Gina gushed.

"Stop, you're embarrassing me," Keith protested.

"It's true. You've probably got a nice package too!" Gina stated, realizing the alcohol was preventing her usual brain-to-mouth filter from working.

Keith laughed nervously. "Well, I don't like to brag, but I do have big hands and feet, you know."

Gina reached out at took one of Keith's hands in her own. "You do! Really nice hands too. They're big, but not too meaty. Nice long fingers. I love them." Gina looked into Keith's eyes for a second. In a sudden moment of boldness, she opened her mouth and took Keith's index finger into her mouth, sliding her lips down it gently. She kept eye contact with the young man the whole time, slowly bringing her lips back up the length of his long finger. As she reached the tip she released it, kissing the tip with her lips then lapping at it with the tip of her tongue.

Gina let go of Keith's hand and there was a moment of silence before both started giggling. "You like that?" Gina asked.

"Um... uh yeah. Very... is it warm in here?" Keith stammered.

"I've got more tricks up my sleeve you know," Gina purred, shocked at her own suggestiveness. Still, what was the harm in flirting? Keith was hot after all.

"I'm sure you do," Keith said. "Still, I'm not sure what your children would say if they walked into their kitchen and found their mommy sucking their babysitter's... finger."

Gina nodded. "Well then, perhaps we should go talk in the spare bedroom. There's a nice sized TV in there. And there's a lock on the door," she added with a wink. Somehow inviting him to the spare bedroom seemed slightly less slutty than bringing him to her bedroom.

Gina stood up, and left the empty wine bottle and glasses on the table. She was almost disappointed that she didn't stagger when she walked to the spare bedroom. She realized that while she was a little tipsy, she wasn't drunk, and the game she was playing with Keith was her own doing.

"This used to be a den," she explained opening the door to a pleasant, uncluttered bedroom dominated by a queen sized bed and large television. "That's why it's at the other end of the hall from the other bedrooms. We converted it when, you know, Clancy and I started having problems."

Keith nodded and sat down on the bed. He fetched the remote from the end table, leaning over so Gina caught a glimpse of his tight ass under his jeans.

"I have no idea what's on TV right now, usually I fall asleep early, exhausted from the kids," Gina explained, sitting down next to Keith.

"I'm happy to watch them for you, and glad you think I'm worth staying up to hang out with," Keith said. He began flipping channels.

"We get a bunch of premium movie channels," Gina suggested. "Clancy insisted on them, and the kids won't let me cancel them.

"I was watching them earlier actually, after the boys were sound asleep."

"Anything good on?" Gina asked, lounging on the bed but keeping her legs in a demure position.

"Well... there was a cheesy movie on one channel. One of those soft-core skin flicks," Keith replied.

"I actually love those sorts of campy movies. Which channel?" she asked. Keith managed to quickly locate the film. An attractive young couple was making out in a hot tub. The woman was in a tiny bikini, and the man had swim trunks on.

"Any idea what the plot is?" Gina asked.

"I believe they are attracted to each other and are going to have intercourse," Keith replied. Gina laughed louder than she intended to.

"Well, I think that there's a scandal here," Gina hypothesized. "The man, he's engaged, but to another woman. Her sister actually."

"Really?" Keith asked, chuckling.

"Yes. He knocked the sister up, which is why he's marrying her. But this woman is the one he really loves." The woman on screen's bikini top came off, revealing very large, very unnatural breasts.

"God, do guys even like tits that fake?" Gina asked Keith.

"Well, I can honestly say that I prefer real ones, regardless of the size. Yours, for example, look very nice under that dress."

Gina blushed. "Should you really be talking that way to an old woman?"

"You're hardly an old woman. If I offended you I apologize. But my statement was true."

"Well I certainly am not offended. So thank you," Gina said. The onscreen man had been licking his partner's breasts and now was simulating terribly fake cunnilingus. "Wow, you can totally tell he's not actually going down on her," Gina observed.

"I told you it was cheesy," Keith replied.

"Is it exciting you?" Gina asked, glancing towards Keith's crotch. There seemed to be a sizable bulge in his jeans.

"A little," Keith replied. "You?"

"I'm a little excited. But I don't think it's the movie," she added.

"Gina... this is fun. I like you. I find you very attractive. But I realize your sons are at the other end of the hall..."

"You want to know where this is headed?" Gina asked, soberly. Keith nodded. "It can go as far as you want," Gina replied slowly. "The kids sleep soundly, and the door is locked anyway..." she trailed off, licking her lips suggestively.

"Ok. This is a little weird for me," Keith stammered. "Sorry, it's just usually things aren't quite so... negotiated."

Gina sighed, slightly crestfallen. Her expression must have betrayed her emotions, because Keith quickly added, "But I want to. You should know that I want you."

Gina beamed. She reached out tentatively to touch Keith's chest. "I don't think either of us planned for anything," she stated, her hand tracing a line down his firm stomach. "We're both adults, even if I'm a bit older. You don't have a girlfriend right?" she suddenly asked, her hand resting just above the waistband of his jeans.

"N-no," he said, his throat obviously dry. "I'm single."

"Good," Gina said, her hand sliding down to touch Keith's package through his pants. "Oh my! Someone is a little excited. Or should I say a BIG excited?" Gina exclaimed, giggling at her own joke. "You weren't lying earlier."

Keith closed the distance between them, climbing on top of Gina and pressing his mouth against hers, kissing her hungrily. Her hand stayed fixed to his package, rubbing his length through his jeans. She moaned involuntarily, it had been too long since she'd been with a man, especially one so virile and sexy.

Keith's mouth remained locked on hers, their tongues dancing together beautifully. Keith maneuvered his hips and Gina released his package, allowing the strong young man to press himself against her pussy. She gasped. She felt his hardness rubbing against her, even through four layers of fabric. Gina smiled to herself involuntarily about deciding to wear sexy panties that night. When she'd gotten dressed she never would have guessed it was the babysitter who was going to see them!

Keith nibbled down her neck and lavished attention up it and her earlobes. She appreciated that he seemed to be taking his time, despite the obvious lust in his pants. Gina moaned loudly as he continued grinding against her and kissing her exposed neck.

She couldn't wait to see his erection, to taste it. She hadn't sucked a cock since Clancy's, and that was several years prior. She hadn't sucked one the size of Keith's since college, and she didn't care to remember how long ago that was.

"I want to suck you," she whispered into his ear, causing him to groan. Gina grabbed his tight ass, pulling him against her even harder.

"Not yet. Later. I want to see you first," he replied.

Gina felt herself blushing as he slowly undid the buttons of her blouse. Her heart was racing a mile a minute. It had been far too long. Years and years had passed since a man had seen her naked, fully exposed, not counting her ex-husband or doctor. She gasped apprehensively as Keith finished unbuttoning her blouse and parted it open, exposing her black lacy bra. She felt relieved when he smiled at her. She still had a womanly figure, but she knew she couldn't compete with the college girls this young stud had unquestionably spent many nights with. She was painfully familiar with how flat their stomachs were, how tiny their waists. Kimmy hadn't been much older than Keith when Clancy began his affair with her.

"Hey," Keith whispered. "You still with me?" He was slowly tracing across the exposed upper swell of her breast along the edge of her bra.

"Yes. Sorry, I just was enjoying your touch so much," Gina replied, resolving to live in the moment and not think about the past. She was in bed with a 22 year old!

Gina undid her pants and slid them off her hips slowly, trying to be sexy as she exposed more of her flesh to Keith. Keith's eyes were glued to her hips as she slipped the pants all the way off and tossed them to the side. Keith grabbed her ass playfully. "Nice thong," he observed. "Very sexy."

"Thank you," Gina beamed, settling upon her back.

Keith leaned over her and kissed her chest then stomach tenderly, savoring every inch of her body. At first Gina felt embarrassed to be put under such scrutiny, but she quickly let herself get lost in the sensations. Her remaining doubts disappeared as Keith slid his hand between her legs, rubbing her through her panties. Gina could feel she was already getting warm down there, and she wasn't even naked yet.

"Lose your shirt!" Gina hissed, then quickly added, "Please?"

Keith flashed her a beautiful grin. "I'll trade it for your bra."

Without hesitation Gina sat up and unhooked her undergarment. She handed it to Keith triumphantly, trying not to think about the slight sag in her tits.

"Wow," Keith whispered. "You are such a Milf!"

"Milf?" Gina asked. She'd heard the term before, but forgot what it meant.

Keith chuckled and shucked off his shirt. He was firm and toned, the very vision of a young stud. "You know, a Mother I'd Love to Fuck?"

Gina giggled. "You should make that a Migf."


"Mother you're GOING to fuck."

Keith laughed. "Well, now that we've decided that and are past the first awkward stage, I gotta ask... do you have a condom?"

Gina's heart sank. "I don't have any." It had been many years since she'd had casual sex, and their encounter was so spontaneous. "I'd be happy to take care of you though, with my mouth."

"No," he replied, to which she frowned, feeling rejected. "I want all of you. It's not every day I see a woman I want to fuck then it becomes a reality. I want to do this right, and I want all of you. I'll run to the gas station and buy a pack."

"Ok," she replied. "I guess someone has to stay with the boys."

"I won't be long," he added, kissing her once more before putting his shirt back on. "Just don't change your mind or fall asleep while I'm gone, ok?"

"I'm WAY too excited to fall asleep," she replied. "And I can't wait to feel you inside me." She reached out to stroke his package through his jeans once more for emphasis.

Gina put her blouse back on to walk Keith to the door, but left off her bra. She kissed him goodbye at the door and watched him run off in the direction of the store. She couldn't help but smile. She didn't imagine a man her age would go to such efforts to have sex, especially with the offer of a blowjob on the table. Gina laughed, realizing how lucky she'd gotten, and was about to get.

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byJamesSD© 14 comments/ 339427 views/ 40 favorites

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