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My Babysitter

My Babysitter

My babysitter came back when she was twenty years old and we had wonderful sex!
Karen started babysitting for us when Brent was born. She was only fourteen, but was the oldest of four kids in her family and, therefore, had a lot of experience with babies. She also lived just three doors down the street, so she was very convenient. She soon became like a member of the family and came around even when she wasn’t required to sit with Brent.

I remember one day when Karen was sixteen she came down to visit, my wife was shopping and I was watching Brent. She looked especially gorgeous that day. She then had beautiful long red hair down to her waist and I must admit that I couldn’t take my eyes off of it. It bounced when she walked and she would throw it back over her shoulders in a very sexy way. She didn’t do it to be sexy, it was just habit; she had no idea it was sexy and driving me crazy!

She liked to sit on the floor and watch TV and I always sat on the sofa. This day she was sitting almost directly in front of me and her gorgeous red hair was almost touching my bare legs.

The TV program wasn’t very interesting so we started to talk about her school and the wrestling class she was taking.

“Wrestling? What made you want to take a wrestling class?”

“Some of my friends were taking it and I figured that sometime it might come in handy. You never know.”

“Show me some of your moves.”

She looked at me inquisitively for a moment then said, “OK.”

She had me stand up and face her and said, “Now I’ll show you how I’ll take you down. Attack me.”

“Attack you? I don’t know.”

“Go ahead. Pretend you’re a bad guy and try to grab me.”

I thought about that for a second, then suddenly reached out and grabbed her by the hair, pulled her toward me, then pushed her backward and down to the floor on her back. I then grabbed her wrists and pinned them to the floor as I sat down on her chest.

“There. How was that? If I was a real bad guy you’d be in a heap of trouble right now.”

“That was pretty good. I guess my hair is not an asset.”

“Oh, your hair is a great asset. Don’t ever cut it. Beautiful hair should always be long.”

“You think my hair is beautiful?”

“Of course I do. It’s gorgeous.”

“You never told me that before.”

“I didn’t think it would be appropriate.”

“Why not?”

“You’re our sixteen year-old babysitter!”

I got off of her and started to get up. She sat up and immediately grabbed my arm and pulled me to the floor and tried to pin me there like in her wrestling class. But I was too strong for her and was able to grab her wrists again and pin her to the floor, my body on top of hers this time; one of my legs between hers, her beautiful hair spread out for over two feet in all directions around her head.

Karen struggled for a few seconds, then just relaxed as we looked into each other’s eyes for a long time. Her eyes were SO green and SO large; a perfect complement to her bright red hair. My head was whirling, my cock was growing, and I knew I should get off of her, but she didn’t seem to mind my being on her.

“Bill, this is a very provocative position you’ve got me in.”

“Sorry. I got carried away with the bad guy thing.”

I quickly got up as she lay there for a few seconds like she was thinking about whether to get up or not. I held out my hand to help her up and said, “I’m a good guy now. Bad guy’s all gone.”

She took my hand and I pulled her to her feet. But she let her momentum carry her toward me and she wrapped her arms around my neck, pressed her young body against me and said, “I think I liked the bad guy.” She was obviously making a pass at me; a good one; a pass that I found very hard to resist.

I took her arms from around my neck and said, “You’re a beautiful girl, Karen, and very irresistible, but you’re too young.”

She stuck out her lower lip in a feigned pout and said, “OK, I guess I understand. But I won’t be sixteen forever.”

Karen continued to babysit for us until she was eighteen, married her boyfriend and moved across town. A year after that my wife and I divorced and she move to a city about an hour away.

That was a year ago and I have started a new life. I’m a weekend warrior and have Brent with me every weekend. I’m still in the same house because my ex-wife married a wealthy man and didn’t want it.

One late afternoon the doorbell rang and it was Karen.

“Well hello stranger! I thought I would take a chance that you’d be home.”

“Hey Karen! Come in. Come in. It’s been a long time. How are you?”

We went into the living room and sat on the sofa.

“Well, my marriage to Carl only lasted about a year, so I’m single again.”

“I’m sorry to hear that.”

“I was shocked to hear about you and Linda. I’m sorry.”

“Well that seems like ancient history now. I’ve moved on.”

We just sat and looked at each other for a long awkward moment as I explored her beautiful face, her gorgeous green eyes, and most of all her long soft red hair.

I don’t know what came over me, but I slowly put my arm on the back of the sofa, which placed my hand behind her head. As I did, Karen turned toward me and laid her head on my arm. This allowed me to run my fingers through her hair.

Her hair was so soft and silky that I thought I would pass out with pleasure. And I was getting an erection like I’d never had before.

Karen moved closer to me and said, “You know Bill that I’m not sixteen anymore.”

“I know.”

With that she moved right next to me, placed her hand on my cheek, and kissed me softly for about five seconds. “I’ve wanted to do that ever since that day we wrestled.”

“I’ve never forgotten that day. It was so hard for me to resist you.”

“You don’t have to resist me anymore.”

She moved from the sofa to the floor, stretched out her arms toward me and said, “Pin me down again.”

I sat there a few seconds looking at the most gorgeous girl I’d ever know, stretched out on the floor inviting me to join her. I got down on the floor on top of her with one leg between her legs the way it was that day four years ago. She had her hands on the floor over her head, waiting for me to grab them like before.

I took her wrists in my hands and lowered my weight onto her. She responded by pushing her pelvis up against my erection, which was obvious since it was pressing against her already.

I looked at her for a long time, studying every detail of her beautiful eyes and gorgeous hair. I wanted Karen so badly that there was no turning back.

“You are so beautiful, Karen. I’ve wanted you ever since that day.”

“Now you can have me for as long as you want.”

We began to kiss passionately, rubbing on each other, breathing heavier all the time. I released her wrist and she placed her arms around my neck.

She began to moan as our kissing became more amorous. I placed one hand on the top of her head and grabbed a handful of hair, then let my other hand wonder down to her nice plump breasts. As I messaged them through her tank top, she moaned and obviously liked it.

I slowly moved my hand down to her leg and moved to the inside of her thigh.

“Bill, can we move to your bed? This floor is kind of hard.”


I stood up and took her by the hand and led her to my bedroom. We embraced and kissed again as she began to pull my T-shirt over my head while I pulled her tank top off. She was not wearing a bra, so once it was off, her very nice breasts were there standing out firmly, the nipples erect, the outline of her bikini standing out against her tanned body.

When my T-shirt was off, she moved to my shorts and pushed them down until they dropped to the floor, leaving only my boxer shorts. My erect cock was clearly visible as it pushed out against my shorts.

I quickly removed her shorts and let them fall to the floor. She was not wearing panties.

Karen then dropped to her knees and rubbed my cock with her hand, then leaned forward and kissed it through my shorts.

I put my hand on the back of her head, grabbed a handful of her red hair, and pulled her face against my engorged cock. She rubbed her face around on it and kissed it until I thought I would cum right there and then.

Then she pulled down my boxer shorts and caught my cock in her mouth when it flipped up toward her face. She then pushed her head forward, taking my full ten inches into her mouth and didn’t gag as it went down her throat.

I now had both of my hands buried in her hair; one on the back of her head and one on the side of her face. God, her mouth felt so good and her hair was so soft and silky! I began to slowly hump her mouth as my climax approached.

Karen pulled my cock out of her mouth and said, “Why don’t we move to the bed?”

I helped her onto the bed where she threw her hair above her head as she lay down, held out her arms, and spread her legs. I lay down on her and kissed her face and lips, then slowly kissed my way down her body until I reached her wet pussy. Karen moaned and pushed her pelvis up to meet my tongue.

“Oh Bill, that’s so good.”

I ran my tongue around her pussy and found her clit at the top. I pushed my tongue hard against it as she moaned loudly, arched her back, and said, “Oh my God! I’m cuming! Don’t stop!”

After her climax I moved up on top of Karen and pushed my ready cock deep into her. She cried out in pleasure as I thrust it all the way in.

“Oh fuck!”

I pumped and pumped on her for three or four minutes as she had another tremendous climax. I then allowed my climax to begin as I made a hard thrust all the way into her and held it there until I started to cum.

“Oh Bill fuck me. Cum in me. Cum in me.”

My load must have been huge because it began to spurt out of her pussy and onto the bedspread as I continued to thrust into her.

After I was finished, I rolled off of her and she used her fingers to catch my cum as it oozed from her pussy. Then she sucked it all off her fingers and swallowed it. Then she went down on me and sucked any remaining cum into her mouth and savored it before swallowing it.

Once she was finished, we cuddled and went to sleep for about an hour.

When we woke up, I said, “I’m starving. Why don’t I take you to dinner?”

“That sounds great, but I’d like to go home and shower first and change into something more appropriate.”

“OK. Is an hour enough time?”


* * *

After a nice dinner we came back to the house and headed straight to the bedroom. We watched each other undress and Karen lay down on the bed. I pulled her up, turned her around and pushed her face down on the bed. She was so short that her feet didn’t quite touch the floor. She kept her chin on the bed with her long hair flowing all the way down her back to the crack of her ass.

I moved to her and pressed my cock against her ass and reached up and grabbed her hair in both hands, then leaned forward and buried my face in it. She began to thrust her ass up at my cock as I placed my hands on her shoulders.

“Bill, do me from behind. I love it that way.”

So I reached down, took my stiff cock in my hand and guided it toward her wet and already quivering pussy and pushed.

“Oh God!” Karen cried out in surprise. “Fuck me!”

I rammed harder into her a second time and she moaned louder, letting me know that she liked it. I kept thrusting into her until she had two climaxes. Then when I was about to cum, I pulled my cock out of her, moved up on the bed, straddled her back, and shot my load into her gorgeous red hair.

“Did you cum in my hair?”

“Yeah,” is all I could manage to get out.

“That is so sexy! You must really like my hair.”

“You could say that.”

* * *

That was twenty years ago and Karen and I are still married. She still has the most beautiful long red hair I’ve ever seen. And we still have great sex two or three times a week. We did some wife swapping with our neighbors a few years ago. That is in the story "Pamela" now available on this web site.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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