tagFirst TimeDiary of John: The Babysitter Lena

Diary of John: The Babysitter Lena

byJcaboose©

This is not the first story but it is the first published. I usually just write them for myself but I really liked writing this one so I decided to actually publish it. Everything in this story is fabricated to create my own ideal world. All sexual encounters between the characters in the story only happens when both parties of of consentual age, 18+. I hope you enjoy.

*****

The diary of John

Memory 3: the babysitter Lena

John back with another memory. I'm going to skip forward in time a little because I love reminiscing about this one.

First off I now live in Washing DC with my beautiful new born baby girl named Kiera. I say she's a baby but she's 3, hell she will always be a baby to me. My wife was Born and raised in DC so when we got married we decided to buy a small 2 story house outside the city. It took forever to find one I liked cause I demanded it needed to have a large basement.

Three years old already and I can tell she already took after her mother, god rest her soul. Her mother, my wife, passed away due to birth complications leaving me to raise our daughter alone with 2 cats.

Luckily the Death Will of my long late parents stated that I would inherit everything once I had matured turning 22 or if my godparents deemed me fit. They didn't. My 22nd birthday was 4 months before Kiera was born. It was good comfort to have a shitfuckton of money I didn't even know I had suddenly show up, especially since the love of my life passed away. Man was I a wreck my brother in law had to live with me for 6 months to take care of my daughter till I was finally able to leave the house.

My parents were stinking rich and I didn't even know about it. We lived in a small flat in the middle of London City. My parents were humble people, my father being a prominent political figure back home and my mother a successful author. Not only did their life savings set me up for life, plus some, living on just my mother's royalties alone I would never have to work a day in my life. Using that money I tried to provide my daughter the perfect living situation hopefully to guide her down a good path.

Although I had more money than I knew what to do with we didn't live the life of luxury, I wanted my daughter to learn valuable life lessons like I did so that when I passed (knock on wood) and she inherited all my money and the value in held. But that didn't stop me from splurging a little.

Before I quit everything and became a hermit for 6 months I worked in construction. When I was finally ready to be functioning human in society once again I decided to make some changes to the house to pass the time.

Having my brother in law living close by made it easier for me since he worked as a full time nanny. Hiring him for 3 years made it possible for me to install a pool, hot tub then steam room, a downstairs dedicated gaming/movie room, beside that the weight room, also a Japanese style bathing room connecting the master bedroom to the guest room. I went to Japan once, I loved their bathing room set up.

Basically I was jobless for 3 years working only for myself. Nonstop for 3 years renovating the house I installed a new everything. Kitchen, a study, living room, dining room, balcony, a 7 foot tall fence because the neighbors were always poking their nose in my fucking business. You name it. All to avoid facing the death of my wife.

Forcing myself to do all this work helped me keep in shape. I still looked

Working at home made it easier to raise Keira and you'd be surprised how much you can get done when your job is either your bedroom door or right outside it. Eventually I no longer mourned her death I celebrated it hoping that if there was a heaven she would be there.

By the end of those 3 years my brother in law got married moving away to start a family of his own which led me to how my promiscuous sexual deviancy started up again. After my wife died I swore to never merry again, I did that once and look where that went. But sleeping around was still allowed.

After my brother in law moved away I hired 2 local girls to babysit Keira. I hired 2 because I didn't want Keira to get attached to them, I still think it was a good idea and I stand by my word.

The local high school had job programs for kids, apparently kinds needed work experience in order to graduate now. One of the jobs offered was babysitting. Requirements to hire a student was you had to have the school counselors visit your home on multiple unannounced occasions for 2 months and inspect every room making sure it was safe, you also needed to take a drug and background test along with multiple interviews. Once you passed you were added to their 'clientele' list and a babysitter would be assigned to you.

This process took painfully slow, but it allowed myself bonding time with my daughter. It also gave me time to think about what I wanted to do. Reading all my mums old books I was inspired to step into her shadow.

The first babysitter to show up at my door was Lena, she was in 10th grade. Nothing remarkable about her. She was a 5'6 skinny white chick that had short dirty blond hair, big ass glasses, and braces.

The second babysitter was Jane also in 10th grade but we'll talk about her some other time.

Questioning Lena while showing her around the house

"So, Lena right?"

"Yes sir."

"German?"

"Excuse me?" She was a shy one. Talking to her would be difficult.

"Sorry, is your background German?"

"Oh, yes. My mothers from Frankfurt..."

Opting to end the forced small talk I just showed her around impressing her with all the work I did renovating the house myself.

Keira took to Lena instantly which put me at ease so I let Lena do her thing. The first 2 months were getting the feel for things so I didn't mind if she screwed up once or twice after that her and Jane were godsends. I asked them to come work 3-4 times a week, more or less depending but neither of them refused work whenever I asked. Which was good since I was paying them quite a bit.

Weeks turning into months then slowly turning into years and I watched as this seemingly unimpressive girl turn into a fun filled goddess. By age 17 Lena maintained her skinny form by playing on the high school soccer team keeping her fit and lean, she maintained a nice natural looking tan by going twice a month to her parents spa. Her breast had filled in nicely coming to a perky 30-C. I knew this cause I had to do her laundry once.

Over time her shy character slowly became a prominent happy one, a bubbly personality and a delight to be around I can't recall ever seeing her without a smile braces no longer hiding her teeth. Her big thick glasses replaced by a sexy reading pair highlighting her bright hazel eyes and she grew her hair out, wavy dirty blond hair now past her shoulders. I paid no mind to it though, just focused my attention on my work. She was attractive, no doubt having a line of boys following her at school.

Over the years we had grown close. Jane and Lena each year had put together a birthday party for Keira. She would seek me out for advice on subjects she couldn't bring up with her parents or friends and she would always talk about her problems with me no matter the embarrassment.

I asked her why once and she told me 'it was because she could trust me and that I was someone outside her life. Someone who had no ties to her problems.' I totally understood where she was coming from. It was nice to have someone around to talk to every once and a while and not having to worry about gossip, I considered her a good friend of mine and so did she.

It all changed one summer evening when I asked if she could babysit overnight two weeks before her 18th birthday. Texting her around midnight Telling her not to wait up I come home to a dark quiet house from a late night of drinking and gaming with some of my old mates. Tipsy I made my rounds before going off to bed, making sure everything was off and all the windows and doors were closed.

Making my way to Keira's room I was sweaty, it was a hot night and I made a mental note to install an air conditioning unit as soon as possible. Looking at Keira she was fast asleep, giving her a kiss on the head I closed the door behind me making my way down the hall to the guest room. Pressing my ear against the door I could hear light snores, happy knowing Lena was safe and sleeping I dragged my way into my room.

Taking off my shirt I decided it would be a good idea to shower before climbing into bed. Once in the bathing room I noticed light coming through the door joining the guest room to the bath. Lena hadn't closed it properly, sighing I quietly walk over to close the door tripping on a towel, probably left by Lena, trying my hardest not to make any noise as I fell. I reached my hand out grabbing the door handle causing myself to fall into the door swinging it wide open.

If you were watching I must have looked stupid cause I fell with the door swing, but it worked, I didn't make any noise. Scrambling back to my feet as quietly as possible seeing that Lena was passed out with the lights on I started to move my way back into the bathing room when i did a double take.

Lena snoring mouth wide open body twisted so she was sleeping with her upper body facing the ceiling while her lower body twisted facing me. Asleep in a crop top bunched up past her breasts, probably due to a restless sleep in the heat, revealing flawless tanned skin and supple perky breast misted in sweat her nipples a light pink. Wearing no pants donning a white thong showing off a camel toe almost see through with the help of her own sweat I saw she was shaved.

Starring at her in awe for longer than I had intended I shook myself back to reality when I began to feel my cock stir. Slowly turning around when I saw her move. Holding my breath staying perfectly still Thinking she was going to wake up. Readying myself with an explanation I sighed with relief seeing she was just repositioning herself. This time I had a rush of blood brining me to a full erection that was extremely uncomfortable in the jeans I wore.

Lena was now laying flat on her stomach, breast squished against the bed shirt still bunched up, arms folded under her head, with my eyes I slowly traced the curve of her back to beautiful curve of her ass. If my friend Trayvon had to desecribe her ass he would say 'that white girl had an ass that would put a sista to shame.' I couldn't find a better way to describe it. Lena possessed a beautiful flawless bubble butt that stood firm and round on her behind. Continuing to trace her I started to realize how fit and thin she was which made me even more hot.

Snapped back to reality by her releasing a sudden loud snore I realized I was stroking myself through my jeans. Quickly turning around I made my way into the bathing room quietly closing she door behind me.

Bathing myself, I furiously masterbaited to the thought of Lena and her bubbly ass bouncing up and down on my cock. Shooting a load that had waited 6 years just to see the light of day only to be shot against a bathing wall I whispered "Fuck... I forgot to turn off her lights."

Laying in bed that night I thought about how ever since my wife died I never allowed myself the opportunity to go out and meet women. I knew I didn't want to marry again, it would be too hard on me, but having someone to relieve your sexual desires sounded nice. I took this as a sign as the universe saying 'if you're not going to find an opportunity I'll give you one.' That night I had a wonderful dream about Lena.

Waking up early like I usually did I peaked into Lena's room seeing that she was still asleep this time lying on her back legs and arms spread apart like a starfish. Peaking into Keira's room pleased to see she was still curled up with one of the cats. She loved cats just like her mum did. Seeing the house was still asleep I got dressed planning out my clothes, making sure to show of as much muscle as possible without being naked I walked downstairs and cooked breakfast.

Wearing pajama pants that showed off my bulge and a workout tank I wafted the smell of bacon, eggs and freshly brewed tea filling the house soon after followed by the sounds of tiny little foot steps make their way towards the smell.

"Daddy!" Kiera screamed happily as she ran and jumped into my arms.

"Hey love! Did you have a good time with Lena last night?"

"Yeah! We watched a movie!"

"Oh? What movie?"

"Fwozen!"

"Was it good?"

"Yup! I woved it!"

"That's good hunny" little did I know I would end up hating that soundtrack really really quickly. Till this day I still can't seem to 'Let the Lyrics Go.' They were burned deep into my memory. "Here hun go wake up Lena, its breakfast time."

"Kay!" And she was gone in a flash.

Minutes later prancing in was Kiera hand in tow dragging a groggy half asleep Lena. Her her crop top not adjusted falling loosely down hanging midway on her stomach, she was now wearing baggy sweat pants and fuzzy socks. My loins stirred remembering the beautiful scene I had laid my eyes on the night before.

"Guten morgen sleepy head. Did you sleep well?"

"Not really" rubbing her eyes" it was so hot last night I was sweating even without a blanket. You look good, did something nice happen?"

"I bet, last night was a hot one and no, not really." Smiling at her with a a semi hard bulging against my pajamas. Using the island to cover myself I asked "your 18th birthday is in two weeks right?"

Perking up a little "she just smiled, yup! I can't wait!"

"Any plans? Big party? Is your boyfriend going to treat you to something nice?" I asked while handing her and Keira each a plate of food and a warm cup of tea.

"No I don't do parties plus no big plans, probably just gonna hang out with friends. Jack(her boyfriend) said he was going to take me to dinner but he canceled last night to reschedule, new date TBA" poking at her food sounding disappointed

"Why don't you go up to Eastern Canada with some friends?"

"Why Eastern Canada?"

Looking over at Kiera she was slowly eating her food, I taught her not to interrupt grown ups while they talked, she was such a good girl! "I went to school in Canada, turning 18 is a big thing there in the west. Their the legal drinking age is 18 and in the east it's 19"

"Woah really? Not 21? Isn't that a bit young?" she smiled at the thought.

"You think that's young back home in England you can start drinking beer at 16."

"Lucky ducks" sounding jealous.

"We're from Eggland?" Kiera asked curiously

Laughing at the cute question I said "I'm from England, you're from America just like your mum."

"Daddy?"

"Yes hun?"

"Where's Eggland? Wait, where's merica?"

Laughing I explained to her as best I could to a 5th ear old. "Daddy has to clean up the study before I play with you okay? Maybe Lena can stay a little longer so you can play together." Looking up at Lena she nodded with a mouthful of eggs.

Swallowing she said "Sure! I don't have plans today and I have to be home before dinner. Is that okay Mr. Ward?" Lena didn't have a car so I always drove her home after she babysat.

"Of course. Besides Kiera's last week of daycare starts at 3 I can drop you off on the way.

"Sounds perfect." Turning her attention to Kiera "what do you wanna do today little cat?"

Looking outside at the hot summer day Kiera said "Pool!"

Cleaning up after breakfast I let the girls go change making my way to the study. I started making a mess as I unorganized the book shelf scattering books on the floor. Spreading useless documents on the couch and chairs. An hour passed and looking at the job I had just done I was pleased. The library study was a mess.

Turning off lights and sitting back in my desk chair I looked outside the window into the backyard where Kiera was splashing around with her floaties. This room was the only room with a two way mirror, from outside on the pool deck this looked like a mirror but on the inside you could see the entire back yard. I had designed this room to be a safe room if anything were to happen. No one would know you were in here, it would take a truck to open the door if locked from the inside. Looking at Lena now I couldn't believe that I had missed this beautiful body that was in front of me this whole time.

My eyes were glued to Lena, hair tied back she wore a black bikini that showed off her hour glass curves. She looked like she wore her old bikini because her top on one size to small for it was not fully covering her breasts. Knowing full well that no one could see me I pulled out my cock and began to slowly masterbait while undressing Lena with my eyes. Kiera being all playful hooked her finger under Lena's bikini top yanking upwards revealing those beautiful breasts all wet for me to see. Embarrassed she quickly placed it back looking around to see if anyone had seen. Thinking no one saw she continued to play with Kiera.

About 10 mins passed when Lena's phone buzzed. Seeing this she lifted herself out of the pool revealing her round plump bubble but, her bikini bottoms had sunken in between her ass crack making it look like she was wearing a thong. Taking the time to re-adjust this she walked picked up the phone.

I was about to cum when I though against it. I wanted the next time I came to be in her. Putting my cock away I walked outside to the pool deck.

"Hey guys! You having fun?"

Setting down her phone Lena smiled "yup we're having a blast aren't we?"

"Yah! Daddy join us!" She said splashing water on my crotch showing off my bulge.

"I dunno, I have to clean up the rest of the study."

"Daddy please!" Splashing more water. I caught Lena staring intently at my crotch watching the fabric slowly tape itself to my skin the wetter it got, slowly revealing the outline of my semi hard member.

Catching herself staring "Oh come on, spend some time with your daughter." Sounding like she needed help "relax while we still have the sun!"

"I dunno...the mess" trying to sound all innocent feigning ignorance to what she was looking at.

"How bout if you relax with us, I'll help you clean up the mess after?" The look in her eyes were saying 'please, I can't keep up with her.'

Laughing I agreed and went inside to change.

I put on my favorite pair of blue swim trunks. They were tight around the crotch and lose around the thighs making it perfect to tease what I eventually wanted to show her. Making my way downstairs I saw Lena was bent down typing a text on her phone. Walking up behind her I 'accidentally' startled her.

"You promise to help me with the study?" I said jokingly

Pivoting quickly around making her face a foot away from my crotch she just stared at my bulge and breathed "promise..."

Quickly shaking herself out of her gaze she stood up quickly saying "a promise is a promise!"

Smiling at my daughter who waved me over I said "then let's play!" Jumping cannon ball into the pool.

We played for an hour or so till even Kiera was tired and wanted to take a nap which was fine by me. The whole time playing I would "accidentally' brush my arms along her breasts or my crotch against her thigh.

All puckered out we all laid down on lawn chairs and relaxed in the sun. A few minutes later Kiera fell asleep on her chair, getting up patting my shorts seeing that they were still moist but not dripping I thought it safe to walk through the house. Picking up my daughter to put her in bed for her nap I walked over to Lena and said "a promise is a promise, we have an hour and a half before we need to leave so let's get cracking."

Picking herself up and drying her hair with the towel I said while walking through the door "I'll meet you in the study."

Returning to the study Lena was already hard at work picking books up off the floor and placing them back in their respective shelves. Happy seeing she was still wearing her bikini I walked in.

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byJcaboose© 9 comments/ 112547 views/ 85 favorites

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