The Babysitter

Babysitter Sex Story

It was the summer after my freshman year in college and I was working in a little sandwich shop/bar on the beach. It was a great gig. Between the cash we were paid every day under the table and great tips from our regulars it was the perfect job for a 19 year old girl.

I worked the lunch shift when all the dirty old men came in for their liquid lunch breaks. They loved coming and sitting at the back bar so they could ogle and tease all the cute teenage girls in short shorts and tiny tanks, ponytails bobbing as they hurried to get food and drinks. I loved working there, as I was a huge flirt and saw nothing wrong with giving these guys a little thrill and maybe a little hope that they could get lucky. They were all great guys and a lot of fun.

One day I was refilling a beer for James (my favorite regular) when he asked "Hey Ann, how would you like to make some extra cash?"

I smiled raised my eyebrows and said "What'd you have in mind?"

He smiled back "obviously not what you are thinking, though I wish I would have thought of it myself."

"Ok, so what do I need to do?"

"Well my wife has to go to a conference out of town and I wanted a night out. Can you babysit Friday?"

"Sure I don't see why not."

"Great come by around 7:00"

I placed his beer in front of him, said I would be there then continued down the bar. As I walked away though, I could feel his stare on my ass, barely concealed by my cutoff jeans. I suddenly looked back and winked, he grinned knowing he had been caught staring and winked back. He was as big a flirt as I was. He was really good looking for a man in his late 30s and I found myself becoming very attracted to him.

'Stop it,' I said to myself. 'He's married and you're seeing someone.'

Soon the lunch rush was over and my regulars headed back to their jobs. I headed for the beach after my shift was over. As I bent over to set up my towel, already stripped down to my bikini, I heard a loud whistle. Pulling up I looked around and there was James driving his work van down the beach. I smiled and waved. He stopped and I went to the driver side window to talk to him. He had a clear view down into my cleavage and he licked his lips.

"Damn girl, I knew you had a fine body but wow!"

"Ha ha very funny, aren't you supposed to be at work?"

"Yeah, yeah, I'm going but I was curious where you got off to after you left Sam's Place."

"Well now you know."

"Yes I do and I won't forget either."

"Get going James or you'll get in trouble."

"All right, don't forget Friday 7:00."

"I won't."

He pulled away and I smiled to myself. I lay down on my towel and spent the rest of the day soaking up the sun.

Friday finally arrived and I found myself nervous. What was I nervous about? I was only going over to babysit for Christ sake. So after calming myself down I got in the car and drove over to his home. He greeted me at the door dressed to kill. He was wearing nice fitting jeans and a button down dress shirt. He smelled wonderful too. My pulse quickened from the overload to my senses and I looked away blushing. He grinned as he realized he achieved his desired effect.

Then he looked me over. Once again my long auburn hair in a ponytail. I had worn a short, form fitting floral sundress which enhanced the tan I had been working on all summer. He licked his lips again, as if he wanted to devour me. He came to quickly, saying he was going to be late. He was meeting up with some of his buddies. Then giving me last minute instructions he headed for the door.

The night was pretty uneventful. After I put the kids to bed I sat and turned on his stereo and flipped through a book I had brought. It must of been around 10:30 when he came home. It startled me as I wasn't expecting him for a couple more hours.

"You're home early," I said.

"Um hum," he replied. I could tell he was feeling good from his evening out and he came over and sat right next to me on the couch. "The kids in bed?" he asked.

"Yes," I breathed. He was so close to me I could feel his desire radiating from him. Mine was rising as well.

He gently ran his hand up my thigh and I jumped from his touch. Then his other hand caressed my cheek. "Ann, let me kiss you."

I didn't respond I just tilted my head up to meet his. He leaned in and kissed me gently at first then increased in his fervor. He slid his hand that was on my thigh around my body to cup my ass and his other that was on my cheek slid to my neck and he pulled me to him hard.

I responded too eagerly as he took charge of my body. I tried to relax and let his skillful hands roam my form. I reached out and pulled off his shirt. He lifted my dress off. I wasn't wearing a bra and he moaned at the sight of my naked breasts as they were suddenly revealed to him for the first time. He cupped first one then the other and lowered his head to suckle them one at a time. Then it was my turn to moan.

"Oh god James," I whispered.

"You are so fucking hot Ann. I have wanted you for so long, your sweet ass and your cherry lips were created to tease me. You are such a fucking flirt and you get me worked up every time I see you. And that damn ponytail I just want to grab it and push your mouth onto my cock with it"

"Well why don't you? You've got me now."

He stood up quickly and unbuttoned his jeans. Then he put his hands to the waistband and slid them down revealing his hard 8 inches. I had limited experience even for a 19 year old and had not seen anything so big. But I was anxious to show him exactly what I could do.

I took him in my hand and ever so lightly licked the top of him. First I licked around and around. Then I moved slowly down his throbbing shaft until I reached the smooth soft skin of his sac. This is the part I loved the most.

Taking his balls in my mouth I tongued and sucked and rolled the soft skin in my mouth. Savoring the feel and taste and smell of his masculinity. I looked up and he was looking down at me amazed and in ecstasy. Then I grinned around him and moved lower. My tongue brushed his asshole and he jumped at the feeling. I circled it around, rimming his hole, he groaned "Godddd!"

He grabbed my head and moved me back up his shaft and I lowered my mouth over him. He grabbed my ponytail and started to bob my head up and down pulling my hair lightly. I knew this was turning him on so I let him continue on. After I had sucked him for a good while he was ready to fuck me.

"Stand up," he said.

I did and he stripped off my panties. "I knew that ass was spectacular," he said.

"Thank you," was all I could say before he bent me over the couch. He came up behind me and pressed his cock against my pussy opening. He was wider than I was used to and he started to push in stretching me. I loved the feeling of him opening me wider than I had ever been. He was going slow, too slow for me. I wanted him to fuck me hard so I reached my hands around grabbed his ass and pulled him inside me.

"Yeeesssss!" I moaned.

"Oh fuck" he said.

"James! Fuck me, fuck me hard!"

He responded by pounding his dick inside me. Harder and harder, faster and faster. We were both panting and sweating. I met him thrust for thrust I wanted him so deep inside almost as if I wanted him to come out the other end of me. He fucked me for what seemed like an hour and I loved it. Always before the men I fucked would cum way before I was ready. I don't know if it was his age but he had stamina.

Finally I could feel my body reaching that point, I was ready to explode. "Oh god I'm going to cum," I said.

"Yes baby, cum for me."

"Cum with me James!" I panted.

"Yeah I'm cumming too. Ready, oh yeah that's it, yeah, yeah, yeah! Fuccccckkkk!"

"Oh god!," I yelled.

I felt him squirt his load deep inside and my release came pouring out at the same time. Our cum mixed together and dripped out of me as he continued to thrust. Finally he lay over me and nuzzled my neck.

"I knew you would be fucking awesome!"

"You're not so bad yourself." I smiled.

"Have you ever fucked the babysitter before?" I asked

"No but I'm gonna definitely do it again." he laughed.

"Yes you sure are," I replied.

We continued our affair for 3 months. It was fantastic. He's my neighbor now. It's been 20 years but as we pass each other on the street we still smile knowing the secret we share. He's divorced now, but I'm married. Still you never know.