9 comments/ 134043 views/ 27 favorites Brittany the Babysitter Ch. 01 By: Chucky1902 I had met Brittany shortly after we moved to our new neighborhood two years ago. Our home search had taken over a year as I needed to clean up my credit before we could move up to the larger home we needed. The best deals were across the river in the newer part of town, but that meant we were leaving our daughters elementary school and all our neighborhood friends. My wife, Pamela, had hired a really hot realtor, Mrs. Leah, to help us with our search. She was a great realtor, and had a nice rack. D cups and very cute. She had the neatest little walk as she strutted about in tight blue jeans while wearing high heels. I loved driving around with her. After lots of false starts, we finally found our dream home, on a quiet street, located just between the local elementary and middle schools. We completed the closing process fairly painlessly, and then began the process of getting the home ready for our family. The house was a Mediterranean two story on a local golf course that had been a foreclosure. As it had been in the foreclosure process for nearly two years, it needed work. A lot of work. All the appliances were missing. Several of the walls had fist sized holes punched in them. The carpet was disgusting. It needed a good scrubbing and then needed to be painted. I took two weeks vacation from work, talked my dad into driving down to help with some free labor, and we went to work; throwing out abandoned trash, ripping out the carpet, scrubbing the interior of the house, then started we started painting. All the bedrooms and closets, the family rooms, the kitchen and the hallways got a new coat of paint. The bathrooms all got new paint, as well as new faucets and hardware. The big home center came out and installed a new garage door. By the end of the second week the new appliances had been delivered and installed, the new carpet was laid down, the utilities were on and we were ready to move in. I hired four of my students from the college to help us with the move. With a large rental truck, and one long Saturday, we got moved in during the middle of August. As we met the neighbors on our street, we were always looking for potential sitters for our six year old daughter Kelly. After a couple of months we met Brittany, a skinny 16 year old sophomore who lived three blocks down the street. She was a lean, gangly teenager, very popular with everyone at the high school. She was on the cheerleader squad, and I was struck at just how cute she was. Her mother had been quick to volunteer her as a sitter and we were soon using her on a regular basis. As a cheerleader, she was often busy, so we soon became adept at planning our weekly dates on Wed, Thurs or just whenever she was available. She was great with our daughter, and even when overseeing the occasional sleepover with Kelly's best friend. Soon she was more like a big sister to Kelly. She would stop by and take Kelly to watch cheerleader practice, volunteered to help with her Girl Scouts troop, and spent time teaching Kelly how to put on makeup. Our families became better friends through the last two years. We would go to football games just to see Brittany cheering on the sideline. During her senior year, she was so busy that quiet often we would have to use our older neighbor Ruth instead, but Brittany always was very special to me. The first few times she babysat Kelly, my wife would drive her home afterwards, but after about third time I drove the very short drive to her home, and after that, taking her home would always be my job. When it was cold I would drive her, but as the spring arrived, I would walk her home. Sometimes when the nights were cool I would find her leaning closely against me during the 10 minute walk. Her perfume was always lingering in my mind during the evenings after our walks. I would usually text her to set up when she would baby sit and then eventually we became occasional texting buddies. Not regular, but every couple of weeks or so, I would check in with her to see how things were going in her life. Sometime during her senior year I noticed we were talking more about her future, especially since I happen to be a small college administrator. Of course I steered the conversation to her boyfriend as well. While they had been together for several months, I really wasn't sure if they were sexually active yet. ------------------------------------------------ About a week after her 18th birthday party in March, my wife and I had gone out for a nice dinner for a couple hours, but had hurried back a bit early because Brittany had mentioned that she might be going out with the boyfriend later that night. When we got back, we found they had decided not to go out so we probably shouldn't have rushed, but my wife was tired, so it really didn't matter. During our usual walk home, I had wrapped my arm around her shoulders and pulled her closer. She didn't seem to mind, and even leaned her head closer into me. When we got to her home I walked her to the door as usual and leaned in to give her a hug. I had lately been giving her a nice, but appropriate hug as I dropped her off. But this was a little different. She held me tightly in the hug, but then leaned even closer and I felt her small, warm breasts crush against my chest. I gently ran my fingers through her hair, but soon came to my senses and realized her mom was about 15 feet on the other side of the door so I reluctantly broke the hug. As I did so, she looked up at me with those big brown eyes, and I just couldn't help myself as I leaned over and gently kissed her on the forehead. She was as shocked as I was as she stepped away and then shyly went into her house. I was a bit nervous as I walked home, but soon heard my phone chirp the arrival of a text message. I looked down to see it was from her. "Thanks" I read, "That was very nice." While I am a typical horny, but basically happily married male, I had not really thought I would ever have a real shot at getting in her pants. Now I began to look at our situation a bit more closely and began to think about the possibilities of getting her alone so I could fuck her. A couple of weeks went by, but I really never could think of a reasonable way to get her naked. And believe me, I was putting some serious thought into the matter. The following week, I made an excuse to take my wife out for a Friday dinner. As usual, I texted Brittany to make sure she was available and to set the time. After I had asked her if she would baby sit Kelly, she asked me if I was planning on walking her home. I was a bit nervous as I replied. I said I would be happy to walk her home, but if she preferred, my wife Pam would drive her and I would certainly understand. She quickly replied that she wanted to walk and enjoy the night. My heart soared as I looked forward to Friday night. --------------------------------------------- As usual, Brittany arrived right on time. She was wearing a pair of faded blue jeans, and a yellow, button up short sleeve shirt. She looked absolutely beautiful. She and Pam exchanged greetings as we got ready to go. We went out for dinner, and then stopped off at a sports bar near our home. Pam had a couple of drinks as we joined a large crowd watching the end of season college basketball tournament games on the big screens. She was a bit tipsy as we got home. She is very short and thin and doesn't drink that often, which was what I wanted so she would immediately go to bed, and hopefully pass out and not take note of how long I was gone taking Brittany home. We set out on our walk as usual. As soon as we were out of sight of my house, she slid up beside me and I wrapped my arm around her as we walked home. We didn't talk much, but did admire the stars under the black sky. We both lived on the local golf course, so I wasn't too surprised when as we were getting near her home she cut between two of the neighbor's homes. We stepped over the small wall that divided the homes from the 14th fairway. We walked up to the back of her house, and she guided me over out of sight of the houses, and we sat under a large old cottonwood tree on the edge of the fairway. We leaned back against the tree and sat looking over the quiet golf course under the dark night sky. Again, I wrapped my arm around her and pulled her close. I felt a slight shiver shake her and I looked into her face and saw her eyes open wide as she felt my hard cock pressed against her thigh. I leaned down and kissed her very gently on the lips. I pressed my mouth hard against hers, and then gently slipped my tongue against her lips. I felt her barely part her lips so I let my tongue slide into her mouth and French kissed her there under the moonlight. Her skin felt electric as I ran my hands over her face and through her hair. She looked at me briefly, then closed her eyes and leaned against me. We sat like that for perhaps fifteen minutes before I roused her and we slowly walked around to the front of her house and she shyly kissed me again, then let herself into her house. As I was walking home, I again heard the chirp of my cell phone and looked down to see it was Brittany. "I am glad you had a good time tonight. Let me know when you need me again," read her message. When I got home that night I had to jack off in the shower, then woke up my very drunk wife and fucked her hard, but I still could not get the taste of Brittany out of my mind. Of course I was trying desperately to think of a way to get her alone, but between Spring Break for my daughter and a trip to Florida for Brittany, I had not been able to get her alone. Brittany the Babysitter Ch. 02 About two weeks before graduation, I came home from work on a Monday to get some very bad news when I arrived. My wife's mother had suffered a stroke and was hospitalized in Connecticut. She was in very bad shape. Our daughter still had 2 weeks of school, so it would be impossible for her leave right now. After talking with our babysitters, our neighbors, and my daughter's best friend, we figured between all of us we could get Kelly to school and then picked up from the bus stop without totally wrecking my work schedule. We decided Pam would fly out immediately, and we would fly Kelly out when she finished the school year. We got Pam off early the next morning without incident. On Friday evening I had a fundraiser to attend to support student scholarships. Too many of my coworkers knew my wife for me to risk taking a date, but I was happy that Brittany would be able to baby sit for the evening. Immediately I started thinking about how to make the evening even more enjoyable, but in the end just decided to let it go and see how things turned out. Brittany showed up on time and I prepared to head out. I had her look over my suit and tie to make sure I was presentable and to show off a bit. She adjusted the knot of my tie and then shooed me out the door after reminding me not to drink and drive. "You look great Mr. James, have a nice time," she said. "Thanks, I will try," I replied. I slipped my cell phone in my pocket, picked up my keys, and gave my daughter a kiss on the forehead. "Make sure you behave yourself," I reminded her. "Give me a call if you have any problems, ok Brittany." "Oh don't worry, she will be fine," Brittany replied. "Now get going." I couldn't help but notice how cute she was as I walked into the garage, got in my car, and drove down to my dinner. It was the usual work crowd. Lots of alumni, and some well known donors we were schmoozing for more donations to support our students. The food was decent, there was a silent auction of some artwork, but the biggest fund raiser was probably the cash bar manned by our Athletic Department staffers. I flirted with a few of my single female coworkers, and even a couple of the coeds who were student workers in my department. By 10pm I was ready to get out of there, so I paid my regrets and my goodbyes and headed home. The house was dark as I drove up. I opened the garage door, pulled in and stopped. I closed the garage door and walked into the quiet house. As I neared the stairs that lead up to the second floor, I saw a faint glow coming from down the hall from my bedroom. I quietly walked in a found the girls asleep on my bed watching the DVD of Titanic. I slide my arms under Kelly and carried her to her bedroom and tucked her in. I turned on her night light, turned the ceiling fan on low, and then left, closing the door behind me. I walked back to my bedroom, dropped my suit jacket and tie on the dresser, then went in to my bathroom. I took a leak, washed my hands and face and brushed my teeth. I returned to my bedroom, being careful not to disturb Brittany as she was sleeping. I turned off the bed stand light she had on, letting just the TV light the room. I sat down beside her and ran my hands thru her hair a couple of times. "Hey sleepyhead," I said. "How was Kelly?" "I'm so sorry," she said. "I must have fallen asleep." She sat up, looked around quickly, with a slightly surprised look on her face. "Where is she?" Brittany asked. "Don't worry, I just tucked her into bed," I told her. I was not sure if she realized I was still gently stroking her hair. "Oh thank goodness," she said. "I almost had a heart attack when I woke up and she wasn't here." "She is out like a light," I assured her. I noticed her eyes turn back to the TV as Leo and Kate were in the garage of the great ocean liner. I knew what was coming up. I think she did too. I thought this might be my best chance, so I took a shot. "This is about over," I told her. "Do you want to finish watching it before I take you home?" I asked. She hesitated for several seconds, the said, "I guess so, if that's all right." "Of course it is," I said as I slid up beside her, pushed two pillows against the headboard and lay back beside her. She sat there for a few moments, then pushed her pillows beside mine, then slowly lay back as well. I put my arm around her shoulder, and pulled her close to me in the darkened room, lit only by the glow of the TV. She rested her head on my shoulder as Leo and Kate climbed up in the car to make out. I tried to be cool as I leaned back and looked at her face as the scene where the lovers were going at in the back seat of the car played out. Her breathing got more rapid, but the she caught me staring at her. I turned away as she said, "That is so tacky, being in the back seat of the car.' "Oh stop it," I challenged her. "Don't tell me you never had made out in a car before." Her face got red as she thought about her answer. "Well maybe a little," she admitted. "But not like that. Not all the way in a car." I let her words hang in the air for a few moments, and then I had to ask the question. "Well where do you go to go all way?" I asked. She froze for a moment, then punched me in the arm. "That is none of your business. I can't believe you asked me that." I had to wrap her up in my arms and roll her onto her back to control her. "Well you know I am always nosey. What did you expect me to ask?" She kind of squirmed under me a little, but I was easily able to control her. I lowered my head until my lips were close to her ear and softly repeated the question. "So where do you go to make out Brittany? Did you ever get to relax on a king size bed in complete privacy?" She was still twisting under me, but with less intensity. "Well no. Never in a bed, really," she said. I leaned over her and kissed her on the lips. She quit fighting me and kissed me back very hard, forcing her tongue into my mouth. We forgot the movie as we kissed. I slide my hand to her cheek and gently stroked her face for a moment, then let my hand slide down her shoulder, past her arm, and down to her waist. I slide my hand along her hip and cupped her small, but perfectly formed ass. She moaned in my mouth while we were kissing as I massaged her ass, grinding herself backwards into the palm of my hand. We continued our passionate kissing there occasionally rolling around the bed and changing positions. Eventually I ended up beside her. I sat partly up as I reluctantly pulled my hand away from her ass. I leaned over her and kissed her cheek, her ears, her nose, her neck, and then began working my way down her chest. Even though he room was somewhat dark, I could easily see her nipples were firm and standing out on her small breasts. I paused just for a moment, then leaned back over her and continued kissing my way down across the gentle swell of her breasts. I felt her stiffen as she realized what I was doing. I thought she might be getting ready to stop me, so I had to distract her fast. I took my right hand and rested it on her upper left thigh for a moment, resting it there on her blue jeans, then began to slowly massage her thigh. Her entire body tensed up for a moment and I felt her shaking. I took that moment to let my mouth drift over her nipple, taking it in my mouth through her shirt, and gently blew on it, knowing she was feeling my warm breath directly on her hard little nipple. She moaned a couple of times, and then slowly began to relax, so as I continued to blow and tease her nipple, I gently and slowly began massaging her thigh. My thumb was on her inner thigh, and as I pressed deeply against her skinny jeans, I could feel her pushing back against my hand. I began alternating my attention to her breasts sucking and licking one, finding they were both equally sensitive. I stopped for a moment to see how she was doing. "Is this ok," I asked her. "Do you like this?" "Yes," she replied in her teenage girl voice. I kissed her hard on the mouth again, then wrapped my right arm around her waist and rolled over onto my back, pulling her on top of me. I continued my assault on her mouth, as I massaged her ass. I pulled her down against me. I was looking into her face as she realized my hard cock was pressed against her. He eyes widened, then closed, as she pushed back against me, grinding against my cock. I grabbed her ass again, then cupped the back of her left knee and pulled her leg over me, spreading her legs wider for me. I slid my hand back over her ass, then down between her legs, and gently began rubbing her pussy from behind. Her body quivered as bit as she felt my hand rubbing against her. She soon developed a rhythm, rocking against my cock, then pushing back against my hand, then back to rubbing against my cock. As she pressed up against me, I began to thrust my cock back against her. Her eyes were tightly shut as she focused on the sensations washing over her. Time lost its meaning to me as we continued like this for quite a while. I decided it was time for us to go a bit further. I pulled my hand away from her ass, and then rolled her onto her back, as I ended up next to her on my left side. I kissed her neck several times then rested my hand on her stomach for a bit. I then ran my fingers lightly over the button of her tight jeans, and unsnapped the top button. I slowly ran my fingers over the zipper of her jean and then began easing it down, wondering if she knew what I was doing. When I got her jeans unzipped, I slipped my hand inside the front of her jeans and ran my fingers down over her silky thong and cupped her little pussy through her soaking wet panties. I leaned close to her ear and whispered to her, "Do you like this Brittany? Do you like me touching you like this?" "Yes," she kind of moaned back to me. "Don't stop," she said as she began bucking against my hand. I moved my fingers up just a bit to get over the waistband of her thong, then slipped my hand under the material and pushed back down and slid over her smooth shaved pussy lips. "You're completely smooth," I commented as I rubbed a finger on either of her pussy lips. "Did you shave for me before you came over tonight?" I asked her. Her cheeks reddened as she blushed when she realized I knew. "Yes," she whispered to me. "I usually keep it shaved, but I did shave it tonight for you. Do you like it?" "Yes, Brittany, I like it very much. It feels so nice and smooth. I really like rubbing it. I think I would like licking it too. Would you like that?" "I've never done that," she replied. "How does it feel?" "It feels better than anything you have ever felt in your life," I assured her. "Would you let me try to do it a little and see if you like it?" "Ok" she said. "Maybe a little bit."