Diary of John: The Babysitter Lena

"Sorry for making you help me. I can be messy when lost in my work"

"No biggie, I'm the same way. My room is in organized chaos."

We worked on different sides of the room in quiet occasionally stopping for small talk. Every once in a while I would pretend to be cleaning just to steal myself some time to admire the ass that would bend over to pick up books. That bubble but looked amazing. Firm and perky It jiggled a little every time she drop herself from being on her tip toes.

Before greeting them at the pool I had shut off electricity to the chandelier hoping to 'get her help' while I attempted to fix it. Asking her to turn on the main light for a second we took notice that it wasn't turning on. Telling her to wait here for a second I grabbed some tools and a 4 foot step ladder and positioned it under the chandelier.

"Can you hold this steady for me while I take a look?"

"Of course I can."

Climbing my way up till my knees met the top of the ladder I reached up and starting 'tinkering' with the chandelier. It just so happened that my now flaccid member was once again in her face as she held up the ladder.

Glancing down at her Staring intently at my trunks that pressed my cock against my leg by my damp trunks revealing its outline. Interrupting her "So about 2 weeks from now, shall we say Monday the day after your birthday?"

Jerking her head upwards "I think I can do that. I don't have any plans other than soccer practice, so probably."

Still tinkering "sounds like a plan how about around 5? I'll leave some money on the counter for dinner. I don't know when I'll be back again, so do you think you could spend the night once more?"

It took her some time to respond so I looked back down "that should be fine I think." She was back to starring at my crotch.

"Sorry to have to make you do this"

"Oh, not a proble..." I 'slipped' 'falling' backwards. I just jerks my legs making the ladder shake. Quickly reacting Lena reached out and grabbed the back of my thighs in a firm grasp.

"Oh my god! Are you okay!!" Scared half to death.

Holding onto the chandelier taking shaky breaths "yea, I'm fine. Thanks for the save" Then proceeded to 'go back to work.'

"No problem. Wouldn't want my boss dead or hospitalized or I'd get no work." Her words sarcastic

"Thanks? I think.."

Laughing she said "no problem Mr. Ward."

"Please call me John, all my friends do."

"No problem Mr. John!" We laughed

With her soft hands now holding onto the back of my thighs I felt her grip tighten slightly. Continuing to tinker I looked down and watch as Lena was tightening my trunks around my thighs trying to get a better understanding of how big my cock really was. Flaccid I would say it was about 7 inches hanging, it grew a little in my early 20's now putting me at a nice thick 10 1/2 inches hard. Pretending not to notice I forced some small talk.

"You and Jane are friends in school right?"

"More like aquatints. We know each other but we hang out in different friend groups."

"Oh really?"

"Yea, shes into science and I'm into sports"

"Right sciences, I knew that. Makes sense, no wonder you're always so fit. Did your boyfriend ever get back to you on that date?"

"No, he hasn't t replied to me since last night. I want to plan something special for him but he isn't responding."

"Something special?" I hinted, "special like a secret sexy night alone?" I had always been the flirtatious type so over the years Jane and Lena came to understand that I loved sexual and racist jokes, breaking conversational barriers and that I wasn't 'flirting' that's just who I was. And after almost 3 years of showing almost no interest in them they came to trust me.

"Really mr... really John?"

"What? I'm just asking." I said playfully

"Well if you must know, we haven't done it yet. I'm still a virgin" she said with pride.

"Really? But you guys have been dating for almost 2 years now right? I was genuinely surprised.

"We are coming up on our year and a half next month. He's been trying but I want to wait till I'm ready. All we've done is just touch." Her words were shy

"Good for you, waiting for the right guy!"

"I'm not waiting for the 'right guy' per say. I'm just waiting till I'm ready."

"So this special day you wanted to have with Jack, you think you're ready?" I asked changing the tone of the conversation

"Honestly, I don't know. And I don't think I will know till I'm in the moment." She was saying thinking her words through "I think it's just something that should happen you know, naturally."

"I understand that. Besides depending on your first, it can either really hurt or not hurt at all. So take it slow. I'm proud of you."

"Thanks, if I'm going to have sex with Jack it will be at my pace, not his. If in the moment I'm ready then I'm ready." She said assuring herself. Thinking about having sex with Lena lit a warm fire in my loins giving me an 8 inch chubby almost as thick as a small red bull can but not quite yet.

"Oh my god." Lena whispered quietly to herself.

"Huh?" Pretending not to know what was going on "did you say something Lena?"

"What?" Lena sounded like I just scared her "nope, nothing is wrong. Just take your time, I don't want you to, um, get hurt." Yah right.

She released her grip on my leg not presenting my cock, peeking down at her she was hovering her hand outstretched and flat above my shaft trying to measure how big it was. Quickly looking up at me hoping I was focusing on my work at hand. Seeing I was 'occupied' she began to mold her fingers to hover around the curve or my cock to see how thick it was no doubt finding she wouldn't be able to wrap her fingers around it. "Oh my god" shocked whisper left her lips.

Thinking that this was enough teasing "THERE!" That should do it. Beginning my descent down the ladder thanking her on the way down. When I was now standing in front of her averting her gaze from my eyes cheeks flushed. "Shit! Look at the time we have to get going soon."

I rushed her out of the study telling her to pack her things while I woke up my daughter to get her ready for daycare. Rushing out of the house I threw on my comfy workout clothes, got both girls in the car and drove off.

Dropping Lena off Kiera stuck her head out the window and yelled "bye bye! See you soon Lena!" With Lena gone, the next two weeks were agonizing. A: because the week after Jane who had turned 18 last month accidentally showed off just how sexy she really was and B: my cock was now always hard for both Jane and Lena I couldn't stop thinking about how Lena was going to spend the night again in 2 weeks and in 3 weeks Jane was going to spend the night taking care of not just Kiera but myself included.

But that's for a different story.

2 weeks had passed and in those two week I prepared everything all the props I would need to make her mine tonight. Tonight, I was going to give her the biggest and best gift she would ever receive on her 18th birthday.

4:30 pm Monday and the doorbell rang. Running to the door was Kiera saying "Lena's here! Lena's here! Hurry up daddy!" I had taken Kiera out all day, ran her ragged but she still had this much energy. I prayed to god she would be fast asleep by the time I had planned to return.

Opening the door "Lena! Please, come in. Did you just come from practice?"

I asked as she walked in to take off her shoes. She was wearing runners with tight grey leggings that were see through when she bent over. I didn't see an underwear outline so I assumed she wore a thong, or even better nothing at all. She wore a loose yellow tank top with a purple sports bra underneath and her hair was tied back in a purple scrunchie.

"Yup"

"By all means take a shower."

"Thanks but I already took one before leaving the gym, what's with the suit?"

"This? I'm going to a company dinner for my friend." I lied, I was just gonna watch a movie to pass the time and come home early at 8.

"Fancy, have fun!"

"Thanks!" Giving her a wink and a smile, "btw happy birthday!" Handing her a flat box big enough to hold a text book wrapped in red.

"Really? You shouldn't have!" She began to open it when I stopped her

"Uhh... it's a very inappropriate gift..." she looked at me puzzled, "let's just say it's something for you to share with Jack on your 'special night.' I know it's a little inappropriate but in my sick twisted head I believe you deserve it."

Genuinely laughing she said "only you... thanks, I'll open it when I have some private time" Giving me a hug to express her gratitude, "what is it though?"

Accepting her hug arms around her waist I pulled her hips closer into mine making sure our groins met. knowing she could feel my cock slowly rise while pressed against her mound through the fabrics that separated us I pressed my body up against hers whispering in her ear as softly as I could "lingerie."

"Oh." hips now pressed tightly into mine most definitely feeling my cock straining to meet her pussy. Leaning back one arm draped around my neck the other hand pressed against my chest keeping us connected at the groin she looked me in the eyes and asked "really?"

Pulling her in for another hug keeping one hand pressing firmly on the small of her back I slid my other hand up pulling her closer till my hand was under her arm wrapped softly around her back. Her arms now draped around my neck I held her there releasing some of the pressure I was putting on her waist making her think the hug was over when instead through the fabric of our clothes I just lightly rubbed my cock against her pussy, whispering my answering in her ear.

"Yes, I took great care in picking one I thought you would good in." Now rubbing her upper back, "I hope he likes it cause I know you'll look sexy in it." hands slowly rubbed my way down to her ass lightly caressing both ass cheeks. Lightly squeezing them in my hands, squishing them together and pulling them apart. We held that hug for a while. Neither her or I pulling away or stopping my hands from fondling her buttox.

"Thank you." A faint whisper into my ear. "I know he'll love it." Releasing my grip allowing her to move away I saw she was flushed red.

I went up to my room to finish 'getting ready'. Looking at myself in the bathroom I looked good. Tall muscular build at 28 I looked like I was 20. No wrinkles or blemish I kept myself clean. The suit was just making me look hotter. Wow... I'm a narcissist.

Going back down readying to leave for my 'event' I said goodbye to Lena and Kiera at the door.

"Bye hun take care of Lena okay?"

"You got it"

"Thank you so much Lena, you're a lifesaver!" I leaned in to give her a light kiss on her cheek as a thank you.

Responding in kind Lena "any time John. I'm always here"

With that I left.

I watched some shitty movie in theaters unable to pay attention wearing a suit like a jackass. Sitting in the theater I wondered how my night would play out. I imagined her stripping herself naked for me or catching her swimming naked and joining. The possibilities were endless and I couldn't wait. With the movie over I grabbed a bite and headed home arriving by 8.

Opening the door trying my best to look worn and beat I walked into a quiet house. Walking upstairs to check the on Kiera seeing she was fast asleep in her bed. Making my way back downstairs I hear noise coming from the game room, when the game room door was closed it was sound proof. No sound in or out which meant someone had left the door open.

Lena was sitting down comfortably on the couch watching a movie. Making my entrance she paused the movie.

"John? what are you doing home so early? What happened? She asked genuinely worried

"Oh nothing I just left cause it was getting extremely awkward." Slumping down next to her, "My mates boss got super drunk right away and yelled at everyone."

"Sounds rough."

"It was."

"What are you watching anyway?"

"This show called Stranger Things, it's really good!"

"Maybe I'll give it a shot later." Getting myself comfortable "how was Kiera tonight?"

"Surprisingly good." Sounding surprised herself "after dinner she hit the hay."

"Happy birthday again by the way!" Happily changing the subject, "we should celebrate!" Getting up I walked to the bar grabbing a case of Stella's, two shot glasses, a mikey of vodka and a small box of chocolates. Popping open 2 Stella's i handed her one and poured us each a shot.

"James, you know I don't drink." She said picking up the Stella giving it a sniff, "I've never even had alcohol before."

"I think tonight calls for a drink. You don't have to be a drinker to have some alcohol." Offering up my beer to her "besides in my house we live by British Law. You're 2 years to old to not have tasted beer before. Shall we toast?"

"Toast to what?"

"To your 18th!"

"To my 18th!"

After toasting we continued to talk passing the time enjoying each other's company. After her first beer I pulled out some vitamin pills I usually took before having a drink because they really helped with a hangover. Telling her this I offered her some and she took them. The only difference between the pills that I just took vs the pills she just took was there was one extra pill in there. A pill I picked up at the local sex shop, made for women it was guaranteed to make any woman horny and soaking wet.

Her first ever shot of vodka was funny to witness and to mask the taste I offered her the box of chocolates. Truth be told it was a normal box of chocolates that I had filled with sex chocolates from the same store. One was suppose to get you horny with enough energy to go all night. We ate 5. Each. After her first shot the next 2 came easy. At this point we had finished 3 Stella's and 4 shots. The more she drank the more she was happy, bubbly and more willing to talk and try new things.

Walking around the game room she started rummaging through some old boxes I never bothered to unpack pulling out 2 boxes labeled 'costumes.'

"What kind of costumes?" She asked curiously eyeing the boxes

"The sexy kind." Saying bluntly, "one box contains costumes guaranteed to make any male sexy and the other for women, guaranteed to make any woman irresistible."

"Really?"

"Yup."

"Can I look through them?"

"Only if you promise to model them for me" I said jokingly

"Deal!" Probably hoping to find something she could borrow for Halloween. Opening the males box she found a cowboy outfit, half of a fireman's uniform and a police officers outfit.

"These aren't sexy!" Sounding disappointed

"They are if I wear them. I guarantee it!" Knowing full well they were costumes for male strippers.

Opening she one marked 'female costumes' she gasped when she picked up the first one. "You tricked me!"

"No, you just never asked." Smiling "I don't think that one would look that great on you, try the next one." Picking up the DreamGirl Lingerie costume called 'Maid to tease.'

"What! No way!" She said laughing, "I can't wear this in front of you!"

"Why not?"

"Cause it's weird!" Happily protesting

"You promised!" I whined

"I know but." Contemplating if she should wear it

"No buts!" I said playfully. "We can do it upstairs in my room where you can change in private." Gathering up all the things, "and if it'll make you feel more comfortable I'll wear a costume too!" I said picking up the fireman costume.

"Fine. But no touching!" Giggling to herself.

"Deal!"

Hurrying up to the master bedroom closing the door behind us we were giggling like school girls. Well, she was a school girl but in any case. I handed her a royal purple satin robe and told her to put it on after she changed. I held a black on in my hands and told her we would reveal ourselves at the same time. Agreeing to that I made my way into the bathing room to change and I she changed in the comfort of my room.

The fireman outfit only consisted of a golden man thong big enough to suppress my cock if chubby but not hard, a pair of fireman pants, red suspenders and a fireman cap, that was it. Changed I looked myself in the mirror to admire my muscular physique. Toned defined 6 pack, bulky chest and amazing arms. I looked like a Greek god ready to strip.

Wrapping myself up in the robe knocking on the door I asked if Lena was ready she responded "in a minute." It was a long minute, "okay. Ready."

Opening the door I saw Lena standing there the Purple satin robe that barely covered her thigh. Black garters ran up her slender legs just meeting the end of her robe giving them the illusion they were hidden in shadow, she was even holding the feather tickler that came with it.

"So who goes first I asked." Not knowing what to do next.

Knowing she was not yet affected by the pill or the chocolate, that was suppose to kick in an hour after taking it and it had only been 30 minutes. Swayed lightly on her feet I knew she had to be tipsy because she said in a seductive tone "your house your rules."

"Then you first." I said sitting back on the bed.

Now standing in front of me reaching her hand to the knot of the robe she paused and still keeping that seductive tone "remember John, no touching." Giving me a wink as she opened and dropped the robe to the ground.

"Woah." Gasping as the robe fell. There was Lena, hot Lena, a virgin 18 year old showing her body to me through sexy see through lingerie. She was wearing a white lace apron with ruffle details that fell and bunched in such a way to hide her mound and peaking through were her puffy pink erect nipples. Noticing her breasts I saw that the apron was barely wide enough to even cover her breasts. Wrapping around her slender waist was a black ribbon bow tied at the front to keep it from moving. Looking closer I saw that she was also wearing the matching black G-string and neck ribbon while holding the feather lightly running it across her cheek.

"So you like what you see?" She asked rocking her hips side to side.

Nodding my head slowly I motioned her to turn around. Turning around she showed me that the back was completely bare, nothing covered her from behind. Only the back ribbon was present telling you 'that if you untied me I would be naked.' Her tight bubbly round ass swaying back and forth as she rocked her hips almost hypnotically. I stood up and she stopped me from moving by saying sweetly "uh uh, no touching only looking remember?"

Moving aside I just pointed at the bed and said "bend over." Now bent over, hands on the bed ass in the air I was able to see the G-string barely cover her puckered asshole. Following her string down I noticed that her ass was a bit too big for the G-String because from the front it looked like she was fully covered but when she bent over the fabric meant to cover her pussy slid forward showing off her bare meaty pussy. The only piece of fabric that 'covered' her pussy was the G-string running up and down the middle of her slit leaving nothing to the imagination.

"Does it look good?" She asked "I can make it look better." Spreading her legs apart she started to bounce her ass up and down. It was beautiful, a bouncing white bubble butt, tight and flawless bouncing in rhythm to a song not heard.

"Give me the feather." Reaching back she handed it to me and I lightly ran it around the sides of her butt.

"I thought we agreed no touching!" Saying in barely a protest

"I'm not touching you." Running the feather down the middle of her ass, "The father is."

"You tricked me again." sounding more turned on then angry

"You can always stop me." Now grazing the feather against her pussy. Pulling it back I saw the feather was soaked in her juices.

"I could." Taking a shaky deep breath, "But you're not touching me so you're not breaking any rules." Interrupted by her phone she reached over to read her text. Falling to her knees on the floor she started crying.