tagMatureThe Babysitter

The Babysitter

byThe Style Guy©

Thanks to MissZ for correcting my 101 errors and making this a more enjoyable story. TSG


"I don't think I'll be able to attend tonight's committee meeting. My damn husband is out of town again and I can't find a babysitter."

I was standing behind two attractive women in the grocery store's express check-out.

"Amy, you have to come. You've done all the work to date and we need the project to remain on track."

"I know . . . I know. I'll make a few more calls and see if I can find a sitter."

My name is Chris. I'm a college sophomore and I'm home for a five week Christmas vacation. My dad has already bugged me about finding some part-time work. 'No son of mine is going to lie around the house for five weeks. Get a job!'

I actually agreed with Dad, but who is going to hire someone for five weeks?

As I exited the grocery store, I saw the mother who needed the babysitter. She was packing her bags in the back of her SUV.

I approached her and started, "Excuse me. I'm Chris. I'm a college student and I'm home on vacation. I didn't mean to eavesdrop, but I'm looking for work and heard you say you needed a babysitter."

I kept a respectable distance, but the woman was looking at me suspiciously, as I continued, "You can call Bob Lewis at the Parks and Recreation Department as a quick reference. I lifeguard at the pool during the summer. Also, Sergeant Jim Parks at the Police Department is a neighbor."

"Anyway," I stuttered, "if you want a babysitter, give me a call." I wrote out my name and cell number, handed her the slip of paper and headed home.

I arrived home after lunch, changed into a tee shirt and sweats. I ran three miles to the gym, lifted weights for an hour and ran home. When I was stripping for my shower, I noticed I had two voicemails.

The first said, "Hi Chris. This is Amy from the grocery store this morning. I talked to Bob Lewis and he says you're a great guy. If you're willing to baby-sit, please give me a call." Amy hung up after leaving her number.

The second message was also from Amy and she sounded a bit more insistent that I call.

I returned her call after my shower. "Hi Amy, its Chris Harrington. Sorry about the delay in returning your call. I was at the gym. Do you still need a babysitter?"

"Oh Chris! Thanks for getting back to me. I'm so desperate."

I teased Amy by saying, "That's the story of my life. The pretty girls call me when their desperate."

I could hear Amy chuckle. "Would you be able to watch my kids from 6:30 until 9:00? Maybe, a little later?"

"Sure Amy." I hung up after she gave me her home address.

I arrived a few minutes early and Amy met me at the door. She's a cute, All-American type. Tonight she's dressed in a red turtle neck, jeans and boots. She's 5'8" and weighs a healthy 150 lbs. Her dark brown hair in permed and shoulder length. I'll bet she has some Asian heritage, as her dark eyes are almond shaped.

Amy's breasts are magnificent. They push her turtle neck out and stretch it to the limit. The cool night air has caused her nipples to become erect. Her waist is slim, but not skinny and the blue jeans she has painted on highlight a truly great looking heart-shaped ass.

As Amy introduced me to the kids, gave me a tour and instructions, she drank from a very full wine glass. I wouldn't consider her drunk, but she was a bit tipsy.

"My meeting is at the Roger's home. Here is their phone number and my cell number. I'll be home around 9 o'clock." She kissed and hugged her kids, waved over her shoulder at me and headed out the door.

Truthfully, I barely saw her wave as my eyes were glued to the twin globes of her ass. They danced as she walked.

Amy's kids were very well behaved. We watched TV until 8:00 and I put them to bed, without any fuss. I checked both children a half hour later and both were asleep.

I was watching ESPN when Amy arrived home just before 9:00.

"Hi, Amy, how was your meeting?"

"Hi, Chris, it was fine. How were the kids?" I noticed a bit of a slur as Amy talked.

"The kids are fine. I checked them a few minutes ago and they're asleep."

"Let me check on them and then I'll pay you."

I watched her ass again as she walked away. Amy is a walking wet dream.

When she returned to the den a few minutes later, Amy was carrying two glasses of wine. "I hope you like Merlot," she said as she handed me a glass.

Amy sat next to me on the small love seat. She rested her back against the arm of the chair, pulled her legs under her bottom and faced me. "I hope you don't mind staying," Amy said, slightly slurring her words. "It gets kind of lonely, with my husband traveling all the time."

"I don't mind at all. I like your company," I flirted.

Amy had a twinkle in her eye. "Oh, you're just being nice. I'm sure you would rather be out with a girl your age."

My heart was beating a million miles an hour. I was far from being a virgin and had great sex with a regular group of college girl friends, but Amy was still a knock-out. More importantly, she was taboo. She's a much older, married mother. My cock was stiffening in my jeans.

"If I tell you a secret, will you promise not to get mad?"

Amy shook her head and said, "Nope." At the same time, she gave me a nice smile.

"I'm sorry then. I can't tell you."

A sexy pout formed on her lips. "Please tell me?"

I scooted closer to her on the love seat. Our hips and legs touched. "I'll tell you, when you promise not to get mad."

In a little girl voice, Amy said, "You're so mean. OK, I promise."

"What do you promise, Amy."

She slapped my thigh and said, "I promise not to get mad, if you tell me your secret."

Nodding, I told her, "This morning at the grocery store, I almost didn't hear you talk about a babysitter. I was to busy checking you out."

Her eyes sparkled with lust as she said, "You're lying."

Taking a sip of wine I waited patiently.

Amy continued, "I doubt you even noticed us."

"Your friend was wearing a white blouse under a blue blazer, blue jeans and black boots. You had on gym clothes. A matching black sweat suit with a white stripe, a cream low-cut top was under the zippered suit jacket and white sneakers." I gave Amy a triumphant smile.

I could tell she was stunned and flattered. Trying to divert my interest, she responded, "I know, Martha is very attractive."

"You're right. Martha is a knock-out and almost as attractive as you."

We starred at each other for a few moments. Her neck and face blushed and began to match the color of her turtle neck.

In an unsure, but lust filled voice, Martha asked, "Would you mind if I changed into something more comfortable?"

"Sure, Amy," I answered equally unsure. "I'll wait here."

I continued to stare as Amy got up from the couch and crossed the room. I couldn't keep my eyes off her jean-encased ass and didn't care when she caught me staring.

Twenty minutes later, I was still waiting in the den. Wondering if she wanted me to follow her to the upstairs bedroom, I had visions of the naked mother laying across her bed and waiting for me.

I was about to follow her upstairs, when my cell phone rang. I answered and heard, "I'm sorry, but I can't do this."

Trying to hide his obvious disappointment, not to mention a raging hard-on, I answered, "Amy, take it easy."

"I don't want you to think I'm a cock-tease, but I've never done this kind of thing before."

My cock twitched when she said "cock-tease," thinking it's sexy when a woman talks dirty. Quickly adapting and trying to get her to forget about her guilt, I told Amy, "I'm going to leave in a few minutes. We can make arrangements for paying me later. But, before I go, can I ask you a question?"

A timid, "Sure," was her answer.

"Have you changed into something more comfortable?"

"Yes," was her answer.

"Something sexy?" I continued.

"I think it's very sexy."

Deciding to push things a bit, I asked, "Is it the emerald green, floor length satin night gown I saw hanging in your closet?"

Amy was quite for an uncomfortably long moment. When she answered, "You're an awfully naughty boy, for looking through my personal things," I knew I'd cleared another hurdle.

"It was my favorite. I was hoping you would put it on."

I could hear Amy breathing, but she didn't respond, so I continued, "I want you to do something for me."

A wary, "What?" Was Amy's answer.

"I want you to lock your bedroom door."

"Why should I do that?" Amy answered.

"Because I asked you too." I continued, "Please Amy, for me."

She didn't answer me directly, but after a few moments, she said, "OK. I've locked the door."

"Stand in front of your dressing mirror. Tell me what you look like."

"I . . . I . . . Jesus, I can't believe I'm doing this.

Amy continued, "If I tell you . . . will you leave?" Her voice was barely above a whisper.

I had returned to the love seat. My legs were slightly spread and my feet were stretched over the far arm. I was playing with my fully hard dick through my pants.

Instead of answering Amy's question, I asked again, "What do you look like?"

"OK. I look . . . oh . . . I look great."

"Is your hair up or is it hanging to your shoulders?"

"I let my hair hang down."

"I'm trying to imagine what your breasts look like. Tell me."

Amy was quite, as if trying to decide if she would continue.

"I'm imagining that they are spectacular. Please. Tell me."

Amy laughed in a sad sort of way. "Spectacular? That's what my husband used to call them."

"Amy, I bet there's a lot of cleavage."

"Yes, more than half my breasts are exposed."

"Do your breasts have freckles? Like you have under your eyes." I was trying to lead Amy.

"Yes, the swell has a lot of freckles."

"And your nipples? Tell me about your nipples?"

Amy was breathing a little harder. "Um . . . um . . . my nipples are hard . . . erect."

"Are they clearly visible through the fabric?"

"They're big and fat and can easily be seen."

"Are your nipples sensitive, Amy?"

Amy tried to regain control and said, "I can't believe you're asking that. I'm married. I have two children. I'm twice your age."

"Amy, your bedroom door is locked. You're safe. I can't touch you. We're having some sexy fun. I just want to know if your nipples are sensitive."

"Oh, God. Yes, they're very sensitive."

"Are you touching them?"

Amy didn't answer.

I continued, "Amy, I'm touching myself. I'm lying on your couch, imagining you standing in front of your mirror and I'm rubbing my dick."

A very quiet, "Yes," was Amy's response.

"Yes? You're touching yourself?"

"MMmmm . . . HHmmm," was Amy's only reply.

"Where are you touching yourself," I asked.

"I'm . . . um . . . lightly pinching and caressing my nipples and . . . um . . ."

I waited patiently.

Amy sobbed, "I can't say it."

I tried to sooth her. "Amy, do you want to know what I'm doing now?"

Amy started, "I'm not sure," but finally admitted, "Oh yes. Tell me what you're doing."

"I will, but first, get into your bed."

I could hear the rustling of the bed coverings and then Amy said, "OK. I'm lying in bed."

"Good girl. I've opened my jeans and pulled them to my knees. As we've been talking I've been stroking my cock and fondling my balls. When pre-cum drips from my piss-hole, I smear it over the head of my cock.

We were quiet for almost a minute. Our heavier than normal breathing was the only sound.

A timid, "I'm touching myself too," Amy admitted.

She continued, "I'm rubbing my . . . my . . . pussy." When she said "pussy", it was barely a whisper.

"Is your pussy wet?"

"Oh my God. I'm drenched."

"As you pinch your nipples . . . imagine I'm sucking them. Would you like that Amy? Having me lick, suck and bite your nipples, while you rub your clit and pussy?"

"Oh yes. That's so nice."

"Imagine Amy, if I kissed over your stomach and between your legs. Can you imagine my tongue working in and out of your pussy?"


"And, over your clit?"

"Oh God, yes!"

"Imagine Amy . . . my tongue is sliding over your pussy lips and to your clit. It's sliding over and over."

Amy didn't answer. But her deep uneven breathing was speaking volumes.



"Can I lick your asshole too?"

"That's sooo dirty. Yes . . . lick me there."

"Are you rubbing your fingers over your asshole now?"

Amy didn't answer, so I continued, "I want you to rub your clit, wet pussy and tight asshole. Will you do that for me?"

A ragged, "I'm doing it . . . now."

"And, your imagining it's my tongue. Aren't you Amy?"

"Oh my God . . . Yes . . . your tongue . . . Yes . . .I'm . . . I'm . . . I'm cuuummminnnggg."

"Keep rubbing yourself Amy. Keep it going."

"So good . . . So fucking good . . . YES . . . AAArrrgggg . . . I'm cuuummminnnggg!"

Amy's orgasm lasted for almost a minute. When she finally settled, she admitted, "That was the best in a long time."

"I'm glad Amy. I'm glad I was able to help you feel good."

"Are you still . . .?"

"Am I what Amy?"

"Are you still . . . playing . . . with yourself?"

"Yes. I'm playing with my dick. Would you like to know what I would do, if I was in your bed and had just finished eating you to orgasm?"

Amy answered, "Yes . . . no . . . Oh God, yes. Tell me."

"I'd slid up your body, kissing and licking you. I'd hold your legs wide and while kissing your lips and tasting your tongue, I'd slid my cock into your pussy. Would you like that Amy?"

Amy sobbed, "I'm so horny."



"Take the vibrator out of your bedside table."

While snooping earlier in the evening, I had found the skinny, five inch penis shaped vibrator.

"I can't believe . . .," Amy tried to sound indignant, but knew she couldn't pull it off.

After a few moments, she continued, "I have it."

"Is it your favorite toy?"

"Yes. It's my favorite."

"Why?" I asked.

"Because . . . um . . . it's about the same size . . . as my husband."

"Put it in your mouth Amy. Get it wet, like you would for your husband."

I could hear the slurping and sucking sounds as Amy put the fake cock into her mouth.

"Can you take the whole toy?"

"MMMmmm. Yes. Easily."

"When it's wet, turn the vibrator on and touch it to your clit."

"Whoa . . . Oh fuck."

"And now Amy, touch it against your asshole."

Amy's tone changed to a high pitched, "AAAAhhhhhh."

"Amy, I'm going to cum soon. I want you to fuck yourself with the toy. Let's cum together."

"It's inside me. Deep inside my . . . my pussy. I'm holding it in."

"Keep going baby. You're so fucking hot."

Amy continued, "I'm rubbing my clit. Circling it . . . with my fingers. I'm so wet. My pussies buzzing. I'm getting . . . I'm getting . . . I'm going to . . . cummmmmmmm."

As Amy babbled and grunted into the phone, I stood over the coffee table and shot my wad. The first shot of jism landed two feet away. The second, only a foot and the rest puddle under at the edge of the table.

We took a few seconds to gather ourselves. "Amy, I'm going to get dressed and leave. Give me a call tomorrow and tell me how you want to get me my money. And, Amy . . . I came all over your coffee table. You'll need to clean it up."

I had a great night sleep and woke early the next morning. It was almost as if the phone sex with Amy had been a dream. My mom and dad left a to-do list that kept me busy until late morning. After completing my chores, I ran to the gym and had a great work-out.

It wasn't until mid afternoon that I noticed I had missed three calls. When I checked voice mail, I listened to a message from a college friend, one from Mom and the last from Amy.

Amy began, "Hi Chris. It's Mrs. Carpenter. You baby sat my children last night." I laughed at Amy's formality, as she continued, "For obvious reasons, I feel uncomfortable having you come to my house or meeting you in person. My children have library school tonight at the town library from 7 p.m, until 8 p.m. My white Ford Explorer will be in the parking lot. I'll leave the door unlocked and your payment on the seat. Thank you."

My goal was still to fuck Amy. I spent the afternoon planning my next step.

I was in my room at 9:30 that night, when my cell phone rang. I saw that it was Amy and decided to let it ring through to voicemail. Amy didn't leave a message, but called every half hour.

I was in bed and finally answered the phone at 11pm. It was immediately obvious that Amy had a few glasses of wine.

In a belligerent tone, she began, "That was a mean thing to do."

"Hi Amy. How was I mean?"

She continued, "That thing . . . that thing . . . well . . . it's just gross."

Earlier in the afternoon, I had visited a local adult toy store. I bought Amy a present, gift-wrap it and left it on her front seat, when I took my babysitting payment.

"I know your other toy was your husband's size. I thought I would get you one that was my size."

Amy was caught totally off guard. She fumbled for words before saying. "You're a liar."

I snickered into the phone. "You're right; it's not exactly my size. My dick is a half inch shorter but much thicker."

"God, you're such a liar. No one's that big."

I was getting annoyed at Amy's tone. "First off, you read Cosmo and that type of magazine. You know from the articles that cocks do get to eight inches. You also have girlfriends who have told you about the big dick's they have fucked. Right?"

"I guess."

"And, you were staring at my cock last night, as we sat on the couch. I was only half hard and you could tell I was big."

Amy didn't say anything, so I remained on the offensive. "Hey, Amy?"


"Are you in bed?"


"You're naked." It was a statement and not a question.

"MMMmm . . . HHHmmm." And then more forcefully, "Yes, I'm naked."

"You have the new toy. Don't you?"

Before she could answer, I continued, "The toy that's the size of my dick?"

"Why are you doing this?"

"Hey, Amy. You called me. Remember?"

Amy didn't respond, so I asked, "Have you tried the toy yet?"

"No," she began. "I'm afraid."

"What are you afraid of Amy?"

"I'm afraid . . . I'm afraid . . .," Amy couldn't finish.

"You're afraid you're going to like it?"

"You must think I'm such a slut."

"I do, Amy. I think you're a slut. I think you're my slut. And Amy, I think you like being my slut."

When she sobbed into the phone, my dick almost exploded.

"Amy, do you think you could swallow this size cock?"

When she didn't answer, I taunted, "I didn't think so."

She quietly spoke up. "You're wrong. I'm . . . um . . . real good at that."

"Then give it a try and tell me."

Amy huffed, grunted and slobbered into the phone. She worked for over two minutes and was out of breath as she quietly answered, "I did it."

I was shocked at her answer, but didn't think she would lie. "You know where to put it next."


"Tell me," I insisted.

"I'm going to slid it into my pussy."

"Use the 'C' word, Amy."

"My cunt. My cunt. I'm going to slide this fat cock into my tight, wet cunt."

And before I could continue, she gasped, "Oh . . . so fucking . . . full. It . . . feels . . ."

I could hear Amy groaning as she worked the fake cock in. Pressing her, I asked, "Are you my slut?"

When she didn't answer, I asked again, "Tell me you're my slut."

"OOOOhhhh! It's all the way in. And I'm your slut."

"Turn on the vibrator."

Amy stiffeled a piercing yell as the vibrator turned on.

"Rub your clit and think of me. I'm pounding my cock into your pussy. It's jack hammering in and out. Your tits are flopping around as I pound you into the mattress.

"Oh, Chris. Fuck me. Fuck me hard. Make me cum."

"Cum for me, Amy. Be my slut and cum for me."

I was rubbing my cock and listening to Amy. "Yes . . . Here it . . . aaagggghhhh . . . cums. So . . . good. So . . . fucking . . . good. I'm . . . cumming . . . aaaagggainnnn.

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