tagMatureNick's Babysitting Adventure

Nick's Babysitting Adventure

byCattoy©

I showed up at the Fisher's house to baby sit in my typical summer outfit of white tennis shorts and a t shirt. Although I had turned eighteen months ago and was about to graduate from high school, I didn't mind babysitting for them. They had a big TV, well-behaved kids, well-stocked fridge and Joanie, their mom, was not only gorgeous, but as I had learned from the occasions when I saw her in a tennis dress and from looking at their vacation beach pictures, she had a great bod!

The door was open so I went inside and heard the shower running upstairs. I yelled up that I was here and Joanie said she'd be right down. I waited at the bottom of the stairs as she walked briskly from her bedroom to the stairs. She was still wrapping a towel around her as she came into view. (What did I just see?) I tried not to stare as she walked down the stairs, her dark tanned skin still glistening with dampness.

"Hi Nick, thanks for coming over. . . Mark is picking up the kids at some friends; they should be here any minute. Let me show you what they're having for dinner." she said as she led me into the kitchen. Her towel was wonderfully too short and I was very happy to follow her.

"Let me get the table set, the glasses are up here," she said as she stood on her tip toes and reached for cups. (Oh my god she's got great legs and I swear I almost saw her ass!) She handed me the cups and I put them on the table as she opened a bottom cabinet to get some plates. I got an even better eyeful but it was over way too quickly. Did she see me looking?

"The kids are just having leftovers. They're in the fridge." I started toward the fridge but she said she'd get everything. She opened the fridge and bent over, looking at the top shelf. "Where are those bowls? Oh, maybe they're down here" and she bent all the way over, legs straight and I could see all the way up those hot legs. I could see that even her ass was tan, smooth and beautiful. Amazing for a 40-year-old!

When she finally brought the food out of the fridge, she turned around but I was still kind of staring, dumbfounded. Ever since I found the pictures of her at the beach I had been jacking off imagining what she looked like naked and there I was staring at her ass!

She gave me a quizzical little look and asked me to get the dinners ready and quickly headed back upstairs to get dressed.

As I got dinner ready, the phone rang. A few minutes later, Joanie called from upstairs, asking me for help. I nervously went upstairs and knocked on her bedroom door. "Come in" she called.

"I'm in the closet. I'll be right there. I need a zip and an opinion."

I could see her in the mirror; at first I was disappointed that there were dark black pantyhose covering her legs. But she moved a little and I was thrilled to see that she was actually wearing stockings to her upper thigh with lace tops! She was bent over, pulling up her dress and her butt looked just as sexy as it did downstairs even though she was wearing black thong panties. As she pulled up the top of her dress, I could see she wasn't wearing a bra, although her back was to me. She was wearing a knee length strapless dress with high slits. As she was looking around for her shoes with her dress unzipped in the back, she told me that Mark was running late and she needed a "man's" opinion about which outfit she should wear that night. I said that I'd be glad to help. When I answered, she looked over and I think I saw her looking at me in the mirror. Our eyes never really met but I think I saw her pause and smile to herself. She put on some 4" inch high heels with straps around the ankles and walked out and sat on a chair in the bedroom. "Don't say anything yet, I need to get these straps on and then you need to zip me up". She crossed her legs and bent down to strap her shoes. Because her strapless dress was unzipped, I could see the top of her breasts. They were perfect! When she crossed her legs to get to the other shoe, I enjoyed the view of her legs. She was having some trouble with the other strap, and more and more of her breasts were in view until I actually saw her nipples. They were perfect too! All the while, she was making small talk and I was having trouble concentrating on the conversation. Especially since I was starting to sport wood. I turned away on the pretense of looking at some artwork she had hanging in her bedroom.

She finally got the other strap fastened and walked over to me and asked me to zip her up. Her eyes dropped momentarily to the bulge in my shorts. Again, she paused and smiled to herself. She stepped closer to me and turned around to be zipped. As she did, her tight ass brushed against the front of my shorts. The zipper was a little stuck and she jiggled a little to help things along. I eventually worked the zipper up even though I hated to seal up the wonderful view of her nipples I had been enjoying. When she was zipped up, the dress looked awesome, form fitting, sexy and elegant. She turned around, stepped back and said "Well what do you think of this one?"

I told her she looked great! She thanked me but she wasn't looking at my face. Rather, she was staring at my crotch. Now she was the one that looks momentarily dumbfounded. She regained her composure, turned around and backed up against me. As I felt her pressing against my cock, she said "well, you're going to have to unzip me if you want something to compare this dress with!" I quickly unzipped the dress, a bit too far, and as she turned toward the closet I could see how erect her nipples had become. I was excited but confused! She was giving me an eyeful and I swore she had just rubbed her ass against me but this was a married 40 year old and I was her baby sitter? Was she coming on to me or was it my imagination?

"This next one's not as formal but we're going to a pretty casual party tonight, I haven't worn it for a while but I think I'm in the mood for it."

She left the closet door open but laughingly said "no peeking!" As she pulled off her first dress, her back to me, I HAD to look. The daily aerobics classes and longs days at the country club pool had done her body good. I loved the look of her dark firm legs and tight ass as she stepped out of the dress. She hung up the dress and looked for the other one. I was treated to a view of her walking around her closet in 4" spike heels, black thong panties, those stockings and nothing on top! Her breasts were small but firm and her nipples were perfect (and still sticking out hard?).

As she reached for the second dress she looked out of the closet and caught me. "I said no peeking!" she mockingly scolded as she held the "dress" in one hand and put her other arm over her breasts. (Was she using her hand to cover up or caress?) The dress was pink lycra and VERY short. In fact, it looked like a cycling jersey! She stood that way until I turned around, smiling (seductively?) the whole time. I waited anxiously as she put on the second dress, taking advantage of turning away from her by readjusting myself so my cock was pointing straight up rather than the more obvious sideways position. The only problem was that I was so excited the head was pushing through the waist band! I untucked my shirt so that it remained safely out of view.

It was a good thing too, because from behind I heard "ready or not, here I come" and I turned around to see her in the skin tight lycra dress that barely came down past her ass. Plus, she had not put a bra on and her nipples were quite noticeable and . . . were those the outlines of her areolas showing through? "What do you think? Too 'young' for an old mom?"

"NO WAY!" I blurted out "I mean, you look terrific in both of them!" As she spun around I could see part of the lace tops of her stockings.

"I might have gained some weight since I wore this, anything showing that shouldn't?" I told her "No but, uh, I can uh, see the top of your, uh pantyhose things".

She laughed and said "Oh, you mean my stockings? I NEVER wear pantyhose, but maybe I have to with this dress. . .What do you think?" "Well, do you need to wear anything?" "Well sweetie, I have to wear underwear! But do you think I have the legs not to wear stockings?"

She sat down on the bed, took off her shoes and slowly rolled off the stockings. She carefully put the shoes back on, crossing and uncrossing her legs in the process. When she was finished, she casually stroked her leg from the ankle to thigh, sat up and said, "Will this work?" "Very well! Uh I think you look really great in that dress too! Uh, if you want to wear it." (I couldn't dare bring myself to say anything about how great her breasts looked or how much you could see)

"Great, there's one more thing I need help with, my purse is on the top shelf in the closet and I don't want to use the step stool in these heels, do you mind?"

Although it felt like half of my seven inch cock was sticking past the waistband of my shorts and only covered by my shirt, nothing looked too obvious as I followed her into the closet. She pointed to where the purse was and I stretched to reach for it. It was behind a few items so it took a minute.

Suddenly I heard "Oh my GOD!" and I realized that my shirt had risen up past my shorts and she could easily see what I had been trying to hide.

"What's wrong?" I ask as I quickly grabbed the purse and handed it to her. "Uh, nothing. . . its, uh just getting late. . . ."

Just then, we heard the front door open and Mark and the kids came in. "We're up here" Joanie yelled.

"I thought you'd be ready!" yelled back Mark, "we're late!!!"

Joanie rolled her eyes and quietly said "thanks for all your help and compliments, that's nice to hear."

Then she looked down at my not so little "problem" and said "I think you better stay up here. I'll just send the kids up. We'll be at a party for one of Mark's old buddies so he'll want to stay forever! Make yourself at home!"

As she walked out, she casually pushed her hand on the lower part of my stomach so that her fingers actually were momentarily on the tip of my cock! She was shaking her head has she walked away. I stood there praying that the kids would be asleep VERY quickly so I could relieve the tremendous pressure Joanie's displays had caused. As the kids came upstairs, I heard Mark yelling: "Do you think you're a teenager wearing that dress?" I'd tell you go back upstairs and put on something more appropriate for your age but we're already too late. Let's just go!"

The kids were a sufficient distraction for things to calm down and by the time they had dinner, stories and were put to bed, about an hour and a half had gone by. I went downstairs to clean up and was startled to hear a car pulling up the driveway. Joanie walked in alone!

"Early night? Where's Mark?" I asked.

"Oh he uh wanted to stay MUCH later than I did, I told him I wasn't having any fun and he told me to go home if I wanted to. So here I am! The only problem is that I have to go pick him up when he's ready to leave and you'll have to stay with the kids when I go. I'm really sorry, I hope it won't be too late. Of course, you'll still be on the clock!"

"You mean I have to hang out with you instead of watching third run movies? AND Mark is still going to pay for my time. I don't think that's anything to be sorry about."

She laughed, "You're so sweet" There was an awkward silence. She still looked so hot. I loved the way her breasts bounced in her dress and her strong tan face with piercing eyes. Plus, I was sure her dress was going to ride past the point of no return at any moment! I started getting hard again. . . But she just thought I was a sweet little geeky high school kid, didn't she?

She quickly glanced up and down my body. . . She paused for another moment, as if in thought. . .and smiled. . . "I'm going to go check on the kids, and then I'll come down and help you finish cleaning up. After that, I think I'm going to need your opinion on some swim suits Mark doesn't think I should wear, since you were so helpful before."

I watched her going up the stairs. It seemed like she was walking slower than usual and I loved the sway in her hips. I also loved the view I got as she headed up the stairs. I could clearly see her thong jiggling between the lower parts of her cheeks. I was in heaven! I continued cleaning and a few minutes later she came back down to the kitchen.

"The kids are totally out! Let me put these things away."

Of course I was treated to more great views as she slowly reached up or bent over to put away the dishes. But I did a massive double take when I saw that she had taken off her panties! Was I dreaming or was she deliberately giving me a show. I was totally hard again but didn't have a chance to adjust and, at that point, didn't want to try!

"Oh do you like that view?" She purred after she had spent a particularly long time bent over, legs straight, supposedly putting away some dishes. Her demeanor had changed. She was more demure and sultry, not friendly and cheerful like she had been earlier.

"What do you mean?" I lied, shaking with nervousness and excitement.

"Oh, nothing I guess. . . here, let me help you rinse those dishes" She reached for the goose neck faucet and started rinsing. It was exciting to be so close to her, our arms and hips were touching. Unfortunately, she misjudged the water pressure and angle of a serving plate and suddenly water was spraying all over, drenching my shirt and shorts and the front of her dress.

"Oh no! We better dry that off!" She grabbed a dish towel and started briskly rubbing my shirt and shorts. . . "I better make sure that gets completely dry!"

Soon, she had her hand around my dick and was practically stroking me with the towel through my shorts! If that wasn't enough, the water had turned the front of her dress practically transparent I was staring at her awesome, erect nipples.

"Oh my god" she softly breathed as she slowed her stroking and hungrily looked in my eyes,"I think we better get these wet clothes off or we'll catch our death!"

She took my hand and led me upstairs. She was in front of me and for the umpteenth time that night, I had that wonderful view. There was a toy car lying on one of the top steps. Still holding my hand, she very slowly bent over and picked up the car. All the while, she was essentially holding me in position so that my face was within a foot of her pussy! It was pink and smooth and though I didn't have experience with these things, it looked swollen and I thought it might even be moist!

Without straightening up, she turned around and whispered "I felt what I'm doing to you, now do you see what you're doing to me?"

I almost came right then. She really was coming on to me! Now I was even more nervous. I didn't know what to say or what I should do. She just led me into her bedroom.

Now her voice was oozing with sexuality: "Why don't you get out of those wet clothes? I was thinking earlier about some swim trunks that don't fit Mark any more that I thought might look very good on you. You can wear them for now while your clothes are drying and you can keep them if you like them." I hesitated. "Are you getting shy now? You can change in the bathroom; I'll get that swim suit and get out of this wet dress myself in the closet. And would you be willing to give me an opinion on those other swim suits I mentioned earlier?"

"Sure" I nodded in amazement.

I went into the bathroom and took off my clothes and waited. A few minutes later Joanie knocked on the door. I opened it just a crack, not wanting her to see me naked! (After all, I was her BABYSITTER) She passed the swim suit to me and I gave her my clothes and quickly closed the door, anxious to have some coverage! When I looked at the suit, I realized that THAT wasn't going to happen. If this was Mark's old suit, it must have been from grade school, it was so small. It was speedo style and had almost no lining left.

I yelled out "are you sure THIS is the swimsuit you thought I would like?"

"Yes!" she answered.

I literally had to stuff myself into the suit. It was so high cut and the waist band was so thin that, with my cock so hard (I'm a thick six inches around) it bulged out obscenely, pushing out the waist so it was visible if you looked down. I was so embarrassed, especially since the suit was very inconsistent with my tan lines!

"Don't you have anything else for me to wear?"

"Well sure! But I really want to see how that suit looks on you and besides, you're still 'on the clock' right? Come on out, I want your opinion on this one piece."

I shyly walked out. She was sitting cross-legged on her bed wearing a fairly conservative looking one piece that was cut very high in the hips. But she still had her heels on! She looked SO hot.

"Well come over closer and I can't see how the suit fits you with your hands covering it!" As I moved my hands away from my crotch, she motioned me closer. For the third time that night, all she said was "oh my god!" and her eyes fluttered a bit.

"Oh that looks fabulous on you! You really, REALLY fill it out. Now, what do you think of mine?"

I was just about to say that I didn't understand why Mark didn't want her to wear it when she slowly lay back on her bed, turned onto her stomach and stuck her ass straight in the air.

It was a thong!

"Are my tan lines okay back there? Are my pussy lips showing? Look carefully" All the while she was slowly rocking her hips. "Well, what's your opinion? Do you like?" I was speechless.

"Well well well, I see that you do!"

Although I had positioned my dick so it was angled toward my hip rather than straight up (it would have been well past the waist band) I was so hard that she could see my cock sticking out both the top and bottom of the narrow waist band on the side.

"So you like Joanie's little swim suit?"

She stepped towards me and brazenly put her hand on my dick through the thin lycra suit. She was rubbing the rest of her body against me and she was whispering hungrily in my ear.

"I've been dreaming of getting my hands on this monster all night. I can't believe how big you are."

She reached inside the suit and started firmly stroking me. Almost angrily she said "Oh I'm going enjoy this cock."

Now my back was to the bed and she grabbed the back of my head with her free hand and pulled me to her mouth in an almost violent kiss, licking and exploring my mouth with her tongue.

She pushed me hard and I fell backwards on her bed. She aggressively crawled up on top of me straddling me with her crotch against mine. She broke another violent kiss, arched her back and quickly pulled the top of her swim suit apart so that her breasts sprang free. As she was arching her back, she firmly grasped her tits and started pinching her own nipples! She also started sliding forward and back on my cock. I could feel her lips parting through the material separating us.

"You like Joanie's titties? Oh please squeeze them" as she pulled my hands up to her breasts. "Yeah, pinch my nipples, hard!" She was rocking her hips faster and harder and her breaths were in time to her rocking. She was moaning. "You're cock's going to feel SO good in my hot little pussy. God I can't wait."

She was moaning and rocking faster and faster. She suddenly grabbed one of my hands and put two of my fingers in her mouth. Her whole head was bobbing up and down on my fingers in time to her rocking and moaning. Suddenly she was shaking violently and I could tell she was cumming, hard.

"Oh my God! I came so hard and you haven't even fucked me yet! Do you want to fuck me Nick?"

"Yes, Please!"

She was still straddling me. She looked down at my cock. The swim suit was now down past my balls.

"Unh! What a beautiful cock, I've got to taste it first! Before it bursts!"

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byCattoy© 15 comments/ 274661 views/ 44 favorites

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