0 comments/ 95383 views/ 6 favorites Kaitlyn By: CalWriter After I split with my drug-addict wife and won custody of my children, life got a little crazy for me. I was just getting started in my investment business and was working twelve-plus hours a day, and now I had two children to care for. So, the only solution I saw was to hire a live-in nanny. I interviewed over twenty girls before settling on Kaitlyn. Strangely, she was the one that I interviewed first, and she was the daughter of some friends of mine from Seattle. She was eighteen, and taking a year off to earn money before starting college. The fact that she was also gorgeous didn't hurt! Five-foot six, with black hair and athletic body (captain of her high-school's soccer and softball teams) and the most beautiful, deep blue eyes. Kaitlyn moved in right before the school year started and my kids loved her immediately. I made a car available to her and she took the kids on outings and to the park. My son started calling her Kay-Kay and the name stuck. The trouble, if you can call it that, started one night after I came home late. The kids were in bed and Kaitlyn was in the family room, watching TV with a bowl of popcorn. She wore a short nightie and was obviously making herself comfortable. Just before she heard me come in I thought I saw her with her hand down her pants, which she pulled out when she heard me. "Hi, Joe. Tough day?" "Not too bad, Kay-Kay. Kids okay?" "Little angels. Bobby's teacher called to say he ought to skip a grade. Janine got an A in finger-painting." I laughed. "With a mother like theirs I am truly lucky they aren't axe-murderers already. Can you fix me a sandwich while I change?" "Sure, Joe." I went up stairs, put away my work and changed into my eveningwear, in this case a college t-shirt and sweats. I thought about a shower and a quick jerk-off, but decided I was hungrier than I was dirty or horny. As promised, Kaitlyn had a sandwich and a glass of milk waiting for me. I wolfed them down quickly then we went into the family room and sat down. I offered her a drink, which she took gladly. I poured us each a brandy. I turned on the TV and was surprised to see the VCR still running. I was greeted with the sight of two people fucking! I guess Kay-Kay had found my stash and was helping herself to it! Quickly she grabbed the remote and shut the movie off. Her face was red with embarrassment, her eyes looking down at her knees. "I'm sorry, Joe." "It's okay. Just make sure the kids don't see any of that." I switched it back on, and saw that Kaitlyn had good taste in porno. The scene she was watching was a very hot encounter between John Holmes and Amber Lynn in a bathtub. "Does it make you uncomfortable watching this with me?" I asked. "No." We kept watching as Amber started sucking on John's huge pole. Her little hand could barely make it around his meat, but good old Amber sure went to work anyway! I glanced over at Kaitlyn and, subconsciously, her hand had returned to her crotch. She gently rubbed her pussy through the material of her nightie. I felt my cock stirring in my sweats, and soon it was very apparent I was aroused. Kaitlyn was stealing glances at my tent pole, each time holding her eyes on it a little longer. Her self-manipulation grew quicker as my cock got harder and bigger. Then, our eyes met, just about the time John started pounding into little Amber. I took her hand in mine and met no resistance. "Joe, is your cock as big as John's?" I laughed. "Sweetie, It's big, but not that big." "Can I see it?" "Kaitlyn, I don't know..." I knew very well she was going to do more than see it! "Joe, I've had a crush on you for a long time. Please?" "Okay." I pulled my sweats down and fished out my penis. It was fully erect, standing up to all nine inches. "You like?" "Yes." "Would you like to touch it?" Not needing to be asked twice, she reached out and gripped my manhood in her hands. She got a good grip and started stroking me. I reached out and pulled her closer to me, my arm around her shoulders. She took my balls in her other hand, gently rubbing my orbs. I kissed the top of her head. "Kay-Kay. Oh, Kay-Kay, that feels great!" "I'm glad, Joe. Do you want to come?" Does the pope shit in the woods? She gripped harder and stroked faster, coaxing the sperm from my balls. I told her to finger my ass while she jacked me off, eliciting a wicked smile. Before long, her fingers found my prostate and I was shooting thick ropes of semen all over my chest. She ran for a towel and cleaned me up. "Are we going to fuck now, Joe?" "I would love to, Kaitlyn. But not with the kids in the house." She looked dejected. I thought for a minute, balancing my desires to stick all nine inches up her little pussy against the thought of my children walking in on us. Then I had a thought. "Kaitlyn, you're off on Thursday. How about I get another babysitter and we can go out?" "That would be great!" I took her head in my hands and kissed her. I had watched this girl grow up and now she was a beautiful woman. "Kaitlyn, thanks for the great hand job. Let me bring you over." With that I reached into her panties, past the thick bush of pubic hair and found her clit. I kissed her again, holding her close and I played with her magic button. She thrust her hips against my hand and practically bit my tongue off as I brought her to orgasm. Her screams were stifled by out joined mouths. Her pussy erupted with cunt oil all over my hand as her insides gripped my fingers. "Thanks, Joe. That was hot!" We put the porn movie away and tidied ourselves up. After checking on the kids we went to our separate rooms and slept quickly. * * * * * It was hard waiting the three days until Thursday. I got a neighbor to watch the kids and picked Kaitlyn up for our "date." She dressed to kill in a clingy black silk dress. I still had on my suit from work. We started with dinner at a nice restaurant, and then I took her dancing. As we both knew, the night was going to end in bed. We pulled into the motel, got a room, and went to it. We started by kissing, our hands roaming over the other. Slowly we undressed each other until we were down to underwear. I had worn my red silk boxers that day, she had on a black push-up bra and black lace panties. I picked her up and put her on the bed, then slowly pulled those panties off. "Do you like to have your pussy eaten?" I asked. She nodded. I started slowly, licking her outer lips. She was already moist with anticipation as I moved my tongue closer to her clit. She let out little moans as I stuck my tongue in her pussy and started fingering her asshole. I looked up and she had taken off the bra and was playing with her nipples, heightening her pleasure. "I'm think I'm going to come....OH YES...YES...Joe! Joe! YEAH...keep...ARGGGHHHH!!!!" Kaitlyn flooded my face with her juices as I brought her over the edge to orgasm. I let her calm down a little as I stood up, removed my boxers and joined her on the bed. She pressed body to mine as I kissed her, sharing her juices with her an an erotic kiss. I started stroking her firm young breasts, now topped with erect nipples. Her hand went for my penis, stroking it. I rose to my knees and guided my erection to her pretty little mouth. She licked the head and took it and my balls in hand. She tried to get as much of it in her mouth as she could, but I could see she didn't have much experience with large dicks. "Is this the biggest cock you've ever sucked?" I asked her. "Oh yeah, Joe. The boys I've fucked were just that. Boys." I chuckled as she continued to bob her head up and down my shaft. Then, as suddenly as she had started, she took my cock out of her mouth and looked me straight in the eye. "I want you to fuck me, Joe, oooh, I want you to fuck me deep, please." I lay down on my back and she climbed on top of me. For the first time I went to work on her small, firm tits. She took my cock in her hand and rubbed it the length of her slit. My hands were all over her back and ass as I sucked on her nipples. Finally, she guides the swollen head of my penis to her opening. Kaitlyn grunted as she sat on my dick, trying desperately to get it inside her. Before long my manhood was enveloped by her tight pussy. "When did you lose your virginity?" I asked. Oblivious to my question she just rocked gently up and down. "Kaitlyn, I'm talking to you, when did you lose your virginity?" "Tenth...grade. AHHHHH!!!" she cried out as the head of my cock penetrated the inner chamber of her womb. Alternating from a quick succession of quick strokes and slow long strokes I began to feel an eruption coming on. Coming up on a long stroke I pulled my cock out of her cunt just enough to maintain the head just outside as I began to rub the slippery knob back and forth between her asshole and her pussy hole. Then I slowly slid it back into her succulent young cunt. "Let me get on top," I said, wanting a little break to keep myself from coming too quickly. As I rolled on top of her little teenage body I wondered how it must have been for the boys who had fucked her before. I got on top and positioned my hands on her ass cheeks. She whispered in his ear, "Don't be afraid, do what you want." I started to fuck her hard. "Oh, oh,oooh, yes, AAHHHHH, that's the way, that's the way, yes, yes, fuck me", she moaned. I pounded her hard letting most of my weight crash into her. "Oh please, fuck me just like that, please don't stop, God it feels so good, break me in half." I grabbed her ass cheeks tighter and with all of my strength I pushed the FULL length of my shaft inside of her. I could feel the rush of sperm beginning to churn up from my testicles, tight in their sac. I started to slow down but the feeling was too incredible. Kaitlyn sensed my impending orgasm and tried to stop me. "Please pull out, Joe. I'm not on..." But it was too late. Nothing on earth could have stopped me then and I released a flood of sperm into her teenage pussy. I pounded so hard as I came that my semen became a froth, leaking out of her cunt and matting our pubic hairs. When I was done I collapsed onto her, exhausted. As my cock began to shrink I rolled off and lit a cigarette. More sperm leaked out of her onto the bed. Kaitlyn came into my arms and I cuddled her. She went to sleep in my arms. After taking a quick catnap I got up, showered and dressed. I took a seat, smoking cigarettes as I watched her. Asleep she looked like a child, at peace and without worry. When she did awaken I kissed her and thanked her for a great time. She told me I was a great lover and asked if we could do it again. I told her Thursday's could be our time and we made plans for the following week. Kaitlyn stayed with me for over two years and every Thursday was our night together. Every bout was better than the last, and I always had a hard time talking to Kaitlyn's parent. Kaitlyn I "met" Katelyn from a social media web site and we had been emailing and texting for about two weeks before we could make arrangements to meet in person. It was a Saturday morning and she had to run to her office early in the morning. Many times she would see clients on the weekend because it was convenient for them. Since I was only working a couple of hours I suggested I meet her at work and we could grab a cup of coffee or something before she started. Her profession is that of a spa like treatment center in the middle of a huge shopping center. There are a few restaurants around in case we wanted to grab a bite to eat, and a nine o'clock time was set to meet. I got there early and was hanging out sitting on the bike when she drove up. DAMN! She looked even better than her pictures. She was wearing a pair of yoga pants and a tight tee shirt like so many girls are wearing now a day. She got out of the car to give me a hug and her tiny waist and slender body looked absolutely amazing. And that initial hug was more of an embrace. No way I would classify it as a "nice to meet you" kind of hug. We decided to sit in her car and talk for a bit since it was our first meeting to get to know each other face to face. The first thing I notice is her hair. It's long, down to her lower back, burnt red in color and I can't think of anything but running my fingers through it. Her smile is bright and genuine which goes along with her blue eyes. Yes, she is nothing less than a smoking hottie. I'd call her a MILF but Jesus; she doesn't even look half of her 48 years in age! We talk and I find out she has had a long string of jobs that are normally stereotyped with the hot women of this world. She was an airline stewardess back in the day when all stewardesses were female and they were all good looking. She was a spokesman, (eye candy) for a leading beer company; you know the ones in the bikinis with the logo across the front? And of course, she was the captain of her cheer leading squad in high school and college, and now coaches cheer in her spare time. And only recently, in the past few years, she has competed in bikini contests with yes, girls half her age and was bringing home hardware. A purely fantasy girl, but here she sat right beside me, and she was interested in me! I couldn't wrap my head around that but... Ok so I don't think I'm a bad looking dude, but no way in hell would I think I would ever have a chance at talking to, let alone hanging with this well documented beauty queen. I guess the saying about charm and personality does go a long way but I'm still pretty cautious as to why this woman doesn't have a hundred good looking men lined up waiting to take her to dinner. She tells me that she gets asked out a lot but most of the guys are phony, and they just don't do anything for her and I was straight up honest with her and didn't try to be someone I wasn't just to impress her. She also told me she was turned on by my "rugged bad boy looks" and the fact I rode a Harley helped my cause as well. She said eventually she hoped to settle back down with a man but wouldn't put her or her daughters at risk if she just settled on some guy, but until then she didn't mind hanging out and having fun with a decent guy she knew wasn't going to hurt her. She also admitted she had a bit of a wild streak still, and again the Harley could bring that out in her. Little did I know at the time how much of a "wild streak" she actually had! So with all this talking and getting to know each other we start to let our guards down and feel comfortable with one another. I ease my hand over on her thigh and she actually scooted over a little closer to me. I took that as my go ahead and leaned over to give her a kiss. She had soft but determined lips. I put my arms around her waist and back and she did the same and we pulled each other in for a long, deep, tongues exploring kiss. This woman knew how to kiss and I told her so. She told me that she really enjoyed my lips and it had been a really long time since she kissed a man who knew how. We talked some more with periodic interruptions to enjoy more of each other's affections. I finally look at my watch and realize we had been sitting in the front seat of her car for a little over two hours. Time really does fly by when you're having fun, so I told her I should let her get on her way to work and I didn't mean to take up so much of her time. She said it wasn't a big deal at all because her office was only about 25 yards away in that same shopping center. Sure enough we were only a few doors away from her office. She asked me if I wanted to come in and see where she worked and I told her sure why not. I really didn't understand the full scope of what she did, or what her office was all about so I figured it would only be one more thing I could learn about her. She grabbed her purse, took out her keys and we walked to the office door. She locked the door behind us and drew down all the shades. Ok now my mind is racing! Why did she draw the shades? Privacy? I called her on it and she tells me that since the office is closed for the day, she didn't want anyone thinking they were open and she keeps everything locked up tight when she was there by herself. She tosses her purse down and begins to give me the personal tour showing me all the different rooms. The waiting area where we walked in was spa like with candles and tropical plants. The back offices were more like well decorated doctors' examining rooms. There were long bed like tables with sheets, pillows and towels to make clients comfortable. Each office having plants and paintings and different decorations to make someone feel comfortable. Each person she worked with had their own specialties and their offices contained equipment that allowed them to do their job. When Katelyn showed me her office it was very welcoming considering it was actually one of the smallest rooms available. Just a bit of mood lighting, the bed and her rolling chair dominated most of the space and it caused us to have to stand really close to one another, which I never complained about. I put my arm around her waist and pulled her in tight. My mouth met hers, lips open for hungry tongues to experience. My fingers combing through her long hair and the kiss deepens. The hand I had around her waist has found itself moving lower, cupping the round soft mound of her ass cheek. I pull her in tighter and she lets out a muffled moan feeling the hardness through my jeans pressing into her belly. I pull her hair back, exposing her long thin neck and my mouth quickly dips down. Kissing, licking and sucking a trail down the base of her neck, down her collar bone and then back up. By this time the moans have grown louder and we can hear each other's breathing getting heavy. I push her back up against the closed office door pinning her in place. My hands move up and down her body taking in every inch I can. Her hips move with mine and we grind our bodies together. My hand lands on one of her small but firm breasts and my fingers find the hard nipple through the cotton material of her tee shirt and give it a little squeeze. She moans louder and does nothing to tell me enough is enough or to stop. And when I dart my hand between her legs and press against her she damn near cries out "PLEASE!" I spin our bodies around and lay her back on the examining bed. I crawl up between her opened legs and our groins dry hump one another while our mouths play havoc on each other. "I want you" I tell her. And she looks at me and nods her head. I quickly remove her tennis shoes and, and in one motion drag both her tight pants and her panties down those long long legs and toss them to the side. Her pussy is gorgeous, bald, slick with wetness, and begging for me. I dive my head between her legs and push my tongue in between the pink folds and get a mouthful of pure honey. Dragging my tongue upward I gather every bit of wetness I can before I swallow and go back for more. When the tip of my tongue hits her clit, her fists clench the sides of the bed and her back arches. Locking my lips around the little nub I begin a full assault. Flicking at it back and forth it takes no time for her muscles to tense and for her to cry out. I ride her through her first orgasm not letting up on the tongue lashing I'm giving her. I only ease up after she cums hard the first time, and then it's only to slow the pace, making small soft circles on the pea shaped bud, occasionally dabbling downward to drink more of the sweetness she has given me. I build her up again and the results are the same. Fists clenching as she locks her legs around my neck and back. Of all the times I had been to a doctor's office, I have never realized but those examining tables are THE perfect height for sex. I'm 6'3" and have a 36 inch inseam, and when I reach down and release my hard shaft from the confines of my jeans, the head is at the perfect level to match her quivering pussy. So with my pants down around my ankles I reach under her ass and pull her toward me. Looking into her eyes, we communicate without words and we both know what's coming next. She takes a deep breath, bites her lower lip and I push forward. The head sinks deep before I pull back a little, allowing her to get used to the intrusion of my eight, very thick inches. She lifts her legs up and around my lower back while I stand between her open and inviting legs. I thrust forward again, sinking a little deeper this time, and by the third time I'm fully inside her and I can feel my balls resting on her ass. I hold there overjoyed at the feeling how incredibly tight she is. I begin a long slow rhythm pulling out to the head waiting just a moment and then I grip my hands on her upper thighs and pull her down as I push my length back inside the cocoon of her sex and again I can't believe how god damn tight she is! In and out I can feel her muscles gripping around me and she was squeezing me with her muscles! I know there is no way in hell I will be able to last long at this pace. I pull her tee shirt up and over her head, release the clasp on the back of her bra, exposing her chest. She has small but pert breasts and the tips are hard and pointy. I bend down to kiss her lips before moving down her chest to suck on the tight hard nipple of one teat. First one then the other and with each movement our moaning gets louder. I prop myself up on my elbows and begin working my hips quicker. She has her ankles on my hips with her legs opened wide, taking everything I can give her. "Holy fuck baby you're tight!" I scream. "It's that big cock of yours working me over" she replies. That about does it! I pull back and out of that lovely tight sheath. I can see her damn near pouting but I reassure her that I'm not done yet. I flip her over and bend her over the table quickly finding my way back inside pure bliss. I reach up and grab a fist full of her long hair pulling her head back. I don't want her face buried in the pillow muffling her screams and I want to find out just how much I can get away with this woman who portrays herself as sweet and innocent. I push hard and deep and she grunts screaming "YES!" Back and forth my hips move thrusting and pounding her from behind. I can feel the wetness dripping down my balls and legs and it fuels my lust even more. I raise my hand and bring it down on her ass. She screams again "OH YES!" And again I slap her ass while fucking her as hard and as deep as I can. The whole scenario is just too damn much for me and I feel my balls tighten. "I'm going to cum" I tell her, not thinking about it before or knowing where she wants me to finish. Is she on the pill? She tells me, no let me rephrase that, she begs me not to stop and that it's ok. "Come on baby, fill me up. Let that big cock cum inside me" and that does it. Dirty talk has always been a weakness of mine in the bedroom, or office as this case may be. With a loud monstrous growl I empty my balls deep inside her. My legs are shaking and my body convulses. I push deeper...she grunts, because I think I hit a spot a little too deep for her. I fall with my chest pressed on her back exhausted and drained. Our bodies sweaty and slick resulting from the incredible workout and fucking we both enjoyed. The pure smell of raw sex permeates the small space. We both are breathing heavy and trying to catch our breaths to talk. I crawl up on the table with her and we curl up into one another. She playful starts to fondle my softening cock, and I tell her I wasn't expecting our first meeting to go quite like this but was damn happy it did. She agreed and told me she was looking forward to our friendship growing and seeing each other more. I told her I didn't know if I could handle how damn tight she was, and her reply? "If you think my pussy is tight you're going to really enjoy how tight my ass is." and gave me a little wink. Holy fuck! Seriously?! Did she just offer her ass up to me? The girl I just met turns out to be a little minx! I know it's getting late and I tell her so and that we both needed to get through the rest of our day. We got up from the table and began getting ourselves together. She showed me where the shower was and I jumped in for a quick wash. When I got out of the shower she was already dressed. I asked her if she was going to jump in the shower and she told me no, she wanted the smell of us fucking to be on her until she went home. Mmmm, Damn I have found me one hot little red head who is a PTA mom in public and a little freak when in private. She walked me to the door and kissed me good bye. I told her I would text her later, and we would figure out the next time we could get together. As I jumped on the bike and was riding home, my thoughts drifted back to what the hell just happened. And then at the end when she told me about how tight her ass was. Riding a Harley with a hard on isn't comfortable at all.