4 comments/ 105183 views/ 19 favorites The New Babysitter Ch. 01 By: C_Steel PART 1: Ashley I thought a sunny day was the last thing I needed. The added heat was almost too much. The movers had done a lot of the work before they left but unpacking was taking extra long. I turned around and almost face-planted, "Jason! Please go find something to do for a minute or two." With my young son Jason under my feet the whole time I was considering calling it a day. It's been just Jason and I for over a year and I thought I could handle it. Being 37 didn't deter me from being a good father, my job kept me in shape and I always figured I could land a good woman. That is until I was forced to move and stress took over. Isn't a better job always a good reason to move? Well no, not always. I had two good reasons for moving, my ex-wife and her new husband being in the same city as me was the other. I wasn't happily single, but happier this way than married. I'll spare the details but lets just say my one wish in life is to never see my ex-wife again. Stepping out onto the back deck the sun hit me like a ton of bricks. Wiping the sweat from my brow I glanced under the sun noticing two girls in the next yard. They hadn't noticed me so I took a moment to take them in. "Just great, this is just what I need," I mumbled to myself. My job just got tougher as I felt my cock twitch under my tight and torn work jeans. Two brunettes, they couldn't have been anymore than 19, both stood there in matching sexy bikinis but they had drastically different body types. Their pink bikinis may have matched in colour but not in size. One was thin and tall wearing her hair up in a ponytail, a cute little thing. But it was the other one who really caught my eye. With her back turned all I could admire was an hourglass figure to die for. Her bikini bottom was no match for her. "What an ass," realizing I had said that aloud I took a step back to keep them from noticing me. It was big, but firm. The type of body usually possible only on a teenager. The tall one glanced over and must have seen me. She said something to her friend before they walked inside. The sexpot didn't even glance back to allow me to see her face. Not that I minded the view of her ass cheeks almost clapping together as she walked inside and closed the door behind her. "Sigh, shows over," I contemplated going back to work on the task at hand but decided I could break for a while and meet the parents of those two sweethearts next-door. I motioned to Jason, "Jason, come on we need to go next door," he had been complaining for quite some time which I figured was understandable. "Don't worry buddy ill have your things in your new room in no time," I said as I took his hand and we went next door. I knocked and waited only to be greeted by another gorgeous, more mature, woman. I'll spare the details of my chat with Ms. Lane but it was pleasant to say the least. Both being divorced and single parents was a good opening to our great conversation. I came to find out that Judy had only one daughter, Ashley. Judging by Judy's voluptuous body there was no question which of the bathing beauties Ashley was. Apparently Ashley was in fact 19, recently out of high school and wasn't exactly planning for the future. "I'm so bored!" Jason cut me off mid-sentence. "Jason just a minute!" I was sure to hide any frustration. Judy laughed which immediately cut the tension. She bent down giving me the perfect view of some of the biggest cleavage I'd seen since my ex-wife. "Jason how would you like a playmate for the next little while?" Jason nodded his head while I looked on a little confused. She bent back up to face me, "I'll send Ashley over to look after Jason for a while." Her pleasantness almost made me regret my earlier thoughts about her daughter, almost. "No, no I don't want you to bother her, I think she's with a friend," I tried to sound as unconvincing as possible. "Non-sense, she babysits all the time, and some time away from that Jessica will be good for her." I returned her gorgeous smile and realized my situation had gotten much better very quickly. Two gorgeous women living together and I had already made a great impression on one. "I really appreciate this, I do have a lot more unpacking to do." Ashley was all I could think of as I made my best effort to sound sincere and hide my excitement, turning to make my way back. Once home working was the furthest thing from my mind. I gave Jason a talking to about being nice to Ashley and he seemed relatively happy about the idea of a babysitter for a while, I'm sure my short fuse as of late was a large part of his desire for someone new to give him some attention. I checked the clock as I unpacked it, "damn, she is taking her sweet ass time," I began to ponder whether she would show and went back to work. She had almost left my mind when she walked in without knocking. "Hey I'm Ashley, my mom said you would know I was coming? Mr. Brown right?" Luckily I wasn't holding anything as my jaw hit the floor. She was still in the same bikini and a pair of sandals, her wild shoulder length brown hair was almost identical to her mothers. A great contrast to the usual straight hair that women prefer nowadays. Her breasts matched her gorgeous ass, full and firm, and for a younger woman they were quite big. Her body was voluptuous and firm, it glistened as if she rubbed it down with lotion daily. When my eyes finally made their way to her face I was happy by what I saw. Her face matched her body well, especially her big sexy lips, they seemed to pout as she talked. "Yes come in, I'm glad you came by", I held out my hand and she playfully slapped it. I laughed as I struggled to keep my eyes on hers and stop them from wandering. "And this mush be Jason!" She picked him up as he approached her and his expression immediately changed. I couldn't believe it, he immediately took to her. "Yep that's him, I umm was wondering if you wouldn't mind..." my words slowed and I paced myself, surprised by how much this teenager was having an effect on me, my cock was rock hard and I was sure she knew it. "...Watch him? Ya I know. Sure I will he's such a cutie," her attention to Jason already had me jealous, she bounced him a few times in her arms and put him down, pausing for a moment. "Something wrong?" I asked, tilting my head curiously. "Well, I realize now I should have changed like my mom had asked, I didn't realize this was so umm, you know, revealing," she pushed her breasts together gently and adjusted her top while glancing down at herself, "I'm just going to go change and I'll be right..." "Oh you look fine!" Cutting her off mid-sentence, I realized I had almost yelled that and she blushed. "I uhhhh mean he's much too young to know anything about that and I'm totally fine with it," I was worried I was sounding desperate now. "I mean it's up to you, however you feel comfortable, I mean you look very cute." I quickly shut up, knowing I was babbling. She was a shade of red by now thanks to me and was still glancing down. "I'm sorry Ashley I didn't mean to cut you off," she only hesitated for a moment, but it felt like an hour. "No I feel fine it's just my mom wouldn't like me over here like this, but she went out anyways, so its cool, whatever, so umm can me and Jason go out in your pool?" She was holding his hand now. "Feel free, his things are in that box," pointing it out. Jason and Ashley went looking for his swimsuit while I tried to act natural. I went to work quickly on the final rooms, deciding to take off my shirt and get a drink. I was confident that taking off my shirt could only help my chances with Ashley. Jason's room didn't take long and I was almost done when I glanced out by the pool. Jason was swimming about while Ashley sat on the side of the pool splashing at him playfully. He laughed and carried on while trying to get her to come in which she finally did. It had been so long since he had a woman's presence like this my feelings for Ashley started to mix. From pure lust to being ashamed of my thoughts for her being younger and now I was just grateful that she was here for us both. I walked out to the pool, "Look's like your getting tired Jason, maybe you should head inside for a nap, your room is all finished." My eyes were fixed on the dripping wet teenager emerging from my pool. She ran her fingers through her thick, wet hair pulling it back. "Awwwww," Jason toned in getting my attention. "Ya I'll take him upstairs in a few minutes, ok?" Ashley walked up to me getting a little water on my now naked chest, reaching up and putting her hand there. Her soft touch sent a sense of delight through my veins and I was confident now that she was more than a little interested in me. I nodded. "Sure thanks, I'll only be a few more minutes." I returned the favour by brushing my hand along her hip, slipping a finger under the material on the side of her bikini bottom and giving her bottoms a light snap, while my mind screamed WHAT AM I DOING? Ashley went back to the pool and sat next to Jason on the side as I turned back inside. My spirits had obviously lifted from just over an hour earlier. Was this really happening? I cursed myself for not paying attention to her reaction. Once I had finished I glanced back to the pool to find it empty. I decided to head upstairs and found Ashley in the hall. "Hey," I said, curious to see what she was doing. "He's all ready for bed but said he wants to talk to you," she smiled sweetly at me and stepped from the doorway. "Oh, ok," I smiled back and winked. "Guy stuff," she teased as I walked in. I leaned down to Jason. "You ok buddy?" He nodded and leaned forward which I knew meant he wanted to whisper something. "What is it?" I leaned in to meet him. "I like her," was all he had to say. I smiled and said, "I like her a lot too bud," making sure she could hear me in the hallway. After tucking Jason in, who was obviously in need of some down time I took a moment and admired all Ashley had done. She had a womanly touch with him that I had forgotten all about. I joined Ashley in the hall and closed the door. "Thank you for your help, let me get my wallet." "Nah you can't afford me," she smirked. I had to smile at that. "No, no I want to," pulling out a fifty and handing it to her. "Well it's a start, so I guess I should get going it's been awhile," she turned to walk away. "Wait, I was actually hoping to take a swim as well, I'd hate to go in alone," I grinned when she stopped and turned back to me. She shrugged, "well...ok, but if my mom were to see just us out there she would have me home in a second, maybe we can just hang out inside for a while." My mind started to spin. My god, she wants to hang out here? With me? My emotions twisted and conflicted. Now was the chance of a lifetime, but at what cost? My cock shut my mind off immediately. "Sure babe but I could use a shower, you can take one as well after being in the pool. It's totally up to you" She nodded and I was forced to turn towards my room and adjust my rock hard cock. "It's this way," I said as I lead her into my room. She took a seat on my bed turning on the TV. "I won't be long," I said as I went into the bathroom closing the door behind me. Finally I had a moment to think about what was happening and to make sure I planned this right. At the hot water hit me my emotions fought a never-ending battle. This teenage sexpot seemed willing but how could I? Or was she really willing? My hand reached for my now soapy cock slowly stroking it, deciding that I would end this tension and send her home. I couldn't consider such a thing. She was just being a nice girl, she was innocent, and her mom sent her here for god sakes. Doing this would make a real relationship with her mother impossible. "I thought you would need a towel," I jumped at the sound of her sexy voice. "Ashley? Are you in here?" I called out. My mind frozen, hand gripping my cock hard. "A towel silly, you don't have any in here yet," her voice was sultry. I almost swung the curtain open and pulled her in with me right then but composed myself at the last moment. I was a gentleman wasn't I? "Ummmm yes thank you Ashley, maybe you should be going now, its getting late," my heart wrenched as I said the words. I waited for a response but got nothing, I quickly finished and peeked out, the door was closed...SHE MUST HAVE LEFT! My stomach dropped and I felt sick, I had blown it. "What have I done?" I repeated. Oh god what a mistake, and if she was interested I upset her. Who gives a shit about morals? What an idiot I am. I took a moment and turned the water off, my mind racing, I had to fix this. There was no way I could pass up even the opportunity at sex with that fantasy fuck toy. I was desperate now, my morals had become nothing but a detriment to me and I promised myself to push them aside no matter what. I reached over to where my jeans had been, but nothing...I glanced around for a towel, no towel. This teenager had a hold on me, my heart was pounding and my cock throbbing. I stepped out of the shower and onto something. "What the?"...I glanced down at a pink bikini on the tile floor and paused. My body was damn near convulsing with lust. I looked at my abs, they showed the signs of heavy breathing. This girl was having the time of her life and I was loving her for it. PART 2: Too Far I pushed the door open fast and it banged against the wall. Ashley jumped, I had startled her, "Hi, did you still want me to leave you alone?" She sounded so sexy in her innocent tone. I was beyond words now as my eyes ate up her naked body, it was still moist from her time in the pool, mine dripping wet. Her shaven pussy nothing but perfect, her nipples erect. Her hands rested on the backs of her hips. I tried to speak as I approached her but she was too fucking desirable. "Mr. Brown? Are you ok mister?" She raised her voice playfully while staring at my cock. That set me off. "Sit," was all I could manage as my hands gripped her shoulders and I pushed her back, forcefully making her sit on the side of the bed as she did with a flop. Her tits bounced as she did. My cock pointing her in the face. I stared down at her as I roughly worked my hands into her hair getting a strong grip on the sides of her head. I groaned just from the feeling of such power over her. But now her expression had changed. She didn't look seductive anymore or even excited, she looked honestly afraid. My muscles ached as I paused, looking at her angelic face, her eyes finally leaving my cock and looking up, our eyes locked. "Open!" I demanded in a voice that even sent a chill down my own spine. It was so close now, oral sex being something my wife would have nothing of in years of marriage. Her lip quivered, "I-I-I never..." was all she got out before I stuck my cock forcefully in her mouth. Her mouth was heaven. I rocked my hips towards her pretty face, immediately going to my tip toes as she grabbed at my hips to try and gain some control of her face fucking. "Ohhhhh fuck yes you good little girl," was all I got out before I heard her gag on my cock. I stopped momentarily then let my head fall back and started to pump into her mouth again. Her slurping and gagging filled the room as I pumped with all I had into her warm mouth. I couldn't look down or I knew I would cum right then. Her luscious lips were like nothing I ever imagined. So close already I slowed down enough for her to turn her head, my cock popping with a slurp from the side of her mouth, drool and pre-cum running down her chin and onto her tits as she gagged again. I breathed deep in total ecstasy as I bent my knees and tilted my head to look at her. I turned her head back forcefully seeing her eyes watering and tears begin to run down her cheeks. My emotions had gotten the better of me once again, what the hell had I done to this girl? "Ready for more angel?" I said much less demanding than before. I began to stroke my hands softly through her now soft and dry hair, praying I didn't go too far. Her face was a shade of red and she was still gagging slightly as she continued to catch her breath. "Baby?" I hadn't realized I had gone so rough. I got down on my knees and looked up at her, "Baby, baby are you ok? I'm sorry I just lost control for a minute there." A few moments later she calmed herself and forced a cute giggle, I sighed in much relief. "God you are so gorgeous and I thought you left, I lost it a little bit there. Have you ever even given a blowjob before sweetheart?" I rubbed her thighs lovingly. She finally spoke, "I had sex before but not that, I'm sorry." I slipped my finger under her chin lifting her face, "No, no , no don't be sorry this was my fault I lost control, it was much to rough. What do you say I give you a lesson in the art of cock sucking? Hmmm sweetie?" I surprised myself by how much of a sleazeball I sounded like but it was working. I tickled under her arms and it worked as she smiled and nodded before giving me a kiss, which I embraced. I reached under her arms and helped her get to her feet as we continued kissing. "Are you sure you forgive me? I promise never to be like that ever again to you, ok?" She slowly nodded, "I forgive you," she looked up at me and gave me a hug that I had to smile at. I outstretched my arms and moaned as my cock was pressed to her flat tummy. She continued to hug me for a moment while I stretched my arms and back and enjoyed her warm embrace. Then I instructed her to clean up a bit, as I noticed I had made quite a mess of her lower lip and chin. "And then you will show me how to do it?" She was obviously enthusiastic as her hands caressed my chest and then playfully pulled on my cock. I nodded, I was loving my teenager more every minute. I reached down and gave her a quick slap to the ass that made her jump and squeal as she headed for the bathroom, "And toss that bikini out here bad girl you wont be needing it until you leave." PART 3: Re-do To say my confidence had never been higher would be an understatement. Here I was naked in my basement looking for toys my wife had never let me use on her and I was now going to get to use them on a gorgeous teenager who was ten times more beautiful, loving and caring than she ever was. Yes I had confidence. I grabbed the few unused toys and headed upstairs, of course there weren't many as Melissa would never agree to being 'degraded' by me but more than happy to be by another man. As I returned to my bedroom I promised myself to not lose control again. I realized then that much of my aggressive tactics were likely due to me trying to get back at my ex-wife somehow, but I promised myself never to take that out on Ashley, my angel. With her I only wanted pleasure and fun, and she was the perfect partner for it. "Sweetheart are you almost done in there? Don't be shy", she was awfully quiet once I returned. "Honey I want this but I promise I want you to enjoy it just as much, you can leave anytime if you want I promise." As I tossed the toys to the floor Ashley decided to join me, coming to me quickly and embracing me. We kissed lovingly for a few minutes, my hands exploring her as she did me. Spending most of my time on her gorgeous full ass, playfully slapping it and squeezing. I noticed that she almost completely copied my movements. I reached down and squeezed her ass, and she did mine. I tickled her backside and she tried the same. "Copycat," I teased before tickling under her arms. "Ahhhh! Hey!" She jumped at that and tried to get me back but to no avail. "Come here honey," I reached my arms out and embraced her. Looking into her eyes I spoke between kisses. "Are you sure you want to do this Ashley? I might surprise you a little but I want you to enjoy it and if you really hate anything we wont do it ok?" As I stared down at her, her expression had changed, her eyes widening. The New Babysitter Ch. 01 "I love you Mr. Brown," she kissed my chest. I almost fell over, "No honey you don't, what we are going to do when we get together is just fun, it's fucking and I don't want you to be confused. I'm too old for anything to really work. I love you too Ashley, and will be there for you in any way I can but I want you to know that the age difference is too much for anyone else to know about ok honey? It would be too complicated." She now looked hurt and confused, like a lost puppy. "Oh honey I do love you so much, but I know you will meet someone your own age someday, fall in love and be in an easier situation." I caressed her cheek as I spoke softly into her ear. "Ok but I still love you anyway," she finally looked understanding of the situation so I kissed her deeply. Breaking the kiss I lead her to the center of the bedroom and lowered her to her knees. Stepping back I realized how comfortable we had gotten being naked together, we had real sexual chemistry and my cock was always rock hard thanks to this girl. I reached down and picked up a small, toy leash and chain. A black collar with purple trim, the chain a shiny silver. I dangled it in front of Ashley who was now kneeling with her hands in her lap and watched her get nervous again, her eyes going big with excitement. "You are so sexy when you get nervous angel," getting down on one knee I slipped the toy leash on and pulled it snug. "This is just for me to have a little fun ok? I want to make sure you suck cock well," grinning big as I stood back up. Ashley was very still, just nodding. I stood there and took in the sight of her kneeling, wearing her little collar and chain. She started cracking a smile. I playfully flicked the chain around and her smile turned into a big grin as I sat in a big armchair in the corner of the room. Now totally nude I leaned back in the chair and spread my legs wide. "What are you gonna do?" Her innocence was much more real than I ever imagined. "You're going to be my play toy for now princess," I slowly tugged on the leash forcing her to crawl slowly towards me. Wrapping it around my hand forcing her closer, my cock twitched in anticipation and was met with a giggle from my new suck toy. "You bad girl you," giving her a quick, little tug and drawing another big grin from her. With the chain running under my thigh and wrapped around my hand I slowly pulled her mouth to my balls, her soft lips touching. I leaned forward and gave her thick ass a few well placed smacks, which got a rouse out of her, before leaning back and taking in the beautiful sight. "Ok now use your mouth on my balls," my other hand running through her hair. I was quick to moan as she began mouthing my balls. Licking and taking them into her mouth as the leash kept her right there. "Ohhhhh wonderful, yes really suck on them," my body jerked in pleasure as she obeyed. Her slurping getting louder and louder as I felt saliva run all over and down my balls. "Ok lower now sweetheart, don't be shy," pushing her head down with my free hand and pulling her down from the bottom with the leash. The feeling indescribable as she began to passionately lick under my balls. Her mouth working wonders down on me. I let her stay down there for a few minutes, giving her mouth a good workout, my cock rock hard. Watching and being sure to smile approvingly down at her when her eyes appeared over my balls, giving her a wink. Her smacking lips and moaning getting me so close. Watching her ass sway in the air as I click the chain from her leash. Her head comes popping up, in only her collar now. "Oh honey you are wonderful," quickly leaning forward and kissing her forehead before leaning right back again in my relaxed position. Laughing at the saliva all over her chin and stringing down to my balls. "Ok you earned for me to let you go, I'm letting you free to suck my cock, do your best sweetie." Letting my hands fall to the sides. Watching her close as she takes my cock, sucking the head with enthusiasm, "Like this?" Her eyes glance up at me while she mumbles her words with my cock in her mouth. "First, Don't talk with your mouth full." I waved my finger at her pretending to scold her. "Don't look up at me honey, just listen. Tilt your head forward and hold the base, now slowly try and get it all the way in, yes bob your head, mmmmm perfect baby, now let your throat relax angel." She was learning quickly, and I was in heaven. Watching this girl bobbing her head on my cock was getting me close to cumming and fast. I pulled her hair back and watched the show. "You're a pro now Ashley, you little cock sucker. Now play with yourself, I know you get off on being such a bad girl." The more I teased her and talked dirty the more she moaned and sucked. "Yeah that's it, your lips were made for sucking cock weren't they?" She responded with an approving moan. Her other hand disappeared below while sucking sounds filled the room. I finally shut up, my cock throbbing harder than I could ever remember. I decided to stop her at once. I grasped her head firmly in place stopping her from bobbing her head. "Ok baby now just suck, just suck, I want you to keep trying to swallow until I say", she obeyed and sucked with a passion that had me cumming in seconds. I started shooting load after load in her mouth, "Ohhhhhh fuck yes bitch, take that cum." I could feel her drink the cum straight from my cock as her body shook from her own pleasure. The blood rushed to my head, letting go of her head my arms fell back and I sat slumped in the chair grinning from ear to ear for what seemed like hours. My mind went blank in total pleasure while this nympho continued to suck my limp cock until I finally opened my eyes and remembered to tell her to stop. Caressing her head as she lays it on my thigh. "I love you Ashley," was all I could get out for the moment. Now I could care less about anything else. We stared into one another's eyes for what seemed like forever until I jumped to the sound of a phone ringing next to the chair I was sitting in. I answered it, "Yes, oh yes Judy, Ashley is right here, of course you can," I put the phone up to Ashley. Ashley never broke her eyes from me while she spoke, "Yes mom it did take a while but Mr.Brown is a real busy man and very nice too, yes mom, I'm sorry ill be right home, love ya." I hung the phone up, "thank you Ashley that was the best I have ever gotten, but this was just part one. If you come over tomorrow I promise to show you something you will love in part two, something much more for you than today. Today was simply to train you to obey. What do you say?" Nodding, Ashley began to stand up as did I. "You should call and ask me to baby-sit again," a smile meeting mine for a kiss. "I'll have you blushing tomorrow I promise," as I grabbed Ashley's bikini. Helping her step into it, tying her top up and watching her wash up in the mirror while I adjusted her bikini. Never seeming to be able to get enough of touching her. As we came to the door I stopped her and handed her $1000. "No I don't know about that much money", her eyes were nothing but pure. "Honey that kind of attitude is why I want to give it, it's just for your other help today. Remember that it's not for any of the secret things we did," knowing full well my guilt was most of the reason for such an amount. Slipping the money in the front of her bikini playfully and giving her a soft slap on the ass, we both laughed and embraced once more. "Tomorrow angel?" My eyes widened in anticipation of a response. "Yes, tomorrow," as she turned and began to cross my yard towards her home. Admiring the same gorgeous ass I had admired a few hours earlier. A sunny day was just what I needed. To be continued...