Diary of John: The Babysitter Lena

Confused what the fuck just happened I took her phone and the text reading.

7:30 pm Sarah P.

I didn't know how to tell you I told jack if he wasn't going to tell you I would. I'm sorry babe, I walked into the bedroom and this is what I found. I had to tell you right away. The party that you didn't want to come to tonight just ended. I was looking for Rosie so we could go home when I walked in on this. That's Christy btw.

Click here to view .jpeg file

I'm so sorry honey. Do you want me to kill him? Call me right away if you need to talk.

Clicking the link her phone loaded a picture of Jack passed out naked with another girl in bed. Reading that my heart sank. I mean, I was in the middle of seducing her into cheating on her boyfriend but the fucker beat me to it. Watching this beautiful girl crying on my bedroom floor I reached without thinking.

Kneeling down next to her I grabbed her phone sliding it away finding its new home under the bed. Grabbing her I pulled her into me my robe slid open revealing my bare chest.

"Oh baby! It's okay it's okay!"

Lena gave way. Her quiet sobs became torrents of heaving screams into my chest. I could feel her broken heart. Half of my thoughts forcing to comfort her the other half screaming 'this is perfect! We can use this. She'll be yours!' I hate to admit it but I was going to be to be the nicest prick in her life tonight.

Minutes passed while I rubbed my hand up and down her bare back rocking her back and forth into my chest letting her cry all her tears away. Every once and a while my hands would rub and caress her soft and firm bubble butt. Soon she was just kneeling leaning into me trying to compose herself through quick shaky breaths.

"Why? Why did he have to do this to me?"

"I know, I know" I said while squeezing and spreading her ass cheeks

"I was going to give myself to him and instead he fucked that whore Christy Dawn! She isn't even pretty!"

"I know, he's an asshole all boys are assholes. Besides you're much hotter and sexier than the girl in the picture." I said delivering a light slap to her right cheek

"I know, I have an amazing bubble ass!" She started going on a tangent saying things she probably would never say to me. "I may not have as big big tits as that whore but at least mine are good to look at!" Pulling away she looked me in the eyes cupping her breast under the apron squishing them together pushing them upwards "SEE! Mine are nice to look at and they aren't saggy unlike hers."

Snuggling her face into my chest she continued "I bet you could fit a fist up her pussy that's how many guys she's slept with. I can barely even fit 3 fingers! Why are guys such assholes!" She asked tears welling up in her eyes again.

Barely 3 fingers?...

Siding down leaning against the bed legs spread I placed her sitting in between me so her bare back was pushing into my bare chest. Giving her a small square pillow she could cry into she curled herself hugging the pillow into her face, her knees to her chest. Asking herself "why are guys such assholes?"

I my placed my hand on her knee saying softly "Sweetie. Guys aren't assholes. Boys are assholes. Guys are stupid and men are kind." my other hand sliding up and down her leg.

"Boys are fucking stupid. You know he threatened to break up with me if I didn't have sex with him eventually. To think! I was 'in love' with someone like him!" My hand on her knee slowly coaxing her legs apart while feeling up her inner thigh.

"Baby, you weren't in love. You were scared no one else would love you if he left you. It's okay." Both hands rubbing up and down her inner thighs now. With each down stroke towards her pussy lightly pushing her legs apart. "It happens to the best of us. But you're young and you have years ahead of you." Left hand now rubbing her stomach under the apron, "and a lot more things to experience."

Getting her to talk about her relationship with Jack she slowly began to realize how much of an ass he was. Speaking into the pillow that she should have dumped him a long time ago. While she was assuring herself my left hand made its to her chest rubbing the under side of her breasts. The other hand now rubbing along the full length of her inner thigh every once and a while quickly cupping her mound to push aside her G-string to expose her pussy.

Resting my open palm on her pussy the other palm massaging her nipple, curious as to why I felt the need to stop her mid personal argument to whisper in her ear.

"Lena, do you want to get back at Jack?" While slowly massaging her clit with my open palm

Screaming into the pillow "How? He slept with the biggest slut in school!" Turning her head so her eyes met mine her voice stating rather than asking, "How would I get back at that."

Moving my hand slowly away from her pussy and back to her inner thigh "just wondering, I'm sure we can think of something. What were you saying again about jack?"

Pressing her face back into the pillow picking up where she left off she continued her rant about Jack and his terrible qualities. I'm pretty sure I heard something along the lines of "when I get a car I'm gonna fucking run him over." Hearing that I laughed causing her to laugh. Snaking my way slowly back to massaging her pussy occasionally sneaking my middle into her vagina.

For a good long while she was bitching and ranting about Jack and how all boys were pigs. Massaging and fingering her pussy for a good long while hand soaked in her juices. The pill and chocolate clearly doing its job she because she was in an angry horny rage. Feeling her take a deep breath in no longer shaky I pulled my hand away from her pussy started rubbing her legs closed. Knowing she was finally grounded to reality I didn't want to touch her pussy or breast just in case.

Looking around the room I saw a small purple dildo peaking its head out of the squashed lingerie box and a camera sitting on the desk. Reaching over grabbing the dildo I said softly in her ear.

"Lena baby, I know how we can get back at Jack."

"Really?" Lifting her head so see what I was doing I waived a small 4inch dildo in her face.

"How can I get back at Jack with that?"

Lowering it between her legs to press against her clit "we take pictures of you in various costumes, in different poses doing different 'things' to yourself." She closed her eyes as I started to stimulate her clit , "then we pick and choose which ones to send to him."

Moaning to her self "but what if he shows his buddies?"

"Don't worry." I mused massaging her breasts with my other hand, "we will just send the sexy pictures showing him what he is missing out on and we will keep the more risqué photos to ourselves."

"I don't know..." she moaned into the pillow while I slipped the head of the dildo into her pussy.

"If he shows his mates they will see how sexy you are. They will think he's stupid for cheating on you." Pulling out to massage her clit again, "Have you used a dildo before?"

"Yes. I have."

"Then lets show him the chances he's missing out on." Pushing the whole dildo into her

A small squeak muffled by the pillow "okay, lets show that bastard what he passed on."

Keeping the dildo in her pussy I lifted her to her feet. Telling her to go to the bathroom to wash her face she did. Setting up a tripod at the foot of the bed picking 2 more costumes she could change into. I also picked out 2 more dildos each bigger than the next and hid them under the blanket.

Coming out of the bathroom face washed with no signs that she was ever crying I grabbed the camera "let's get started."

We started out with some simple pictures, click*. Her standing there making various Maid poses facing the camera.

"How do I look?" Voice small and face flushed, click*.

"Beautiful baby, (click)* beautiful." She smiled, "now turn around and place your hands high on the wall."

Taking pictures of her tight ass turned me on, I had to control my urges so I didn't get a hard on. Click* "Bend over a little and spread your legs." Click*

She complied, noticing that her wetness was slowly running down her leg, click*. I spotted the purple dildo still in her pussy, setting the camera on the tripod "you know, it would probably make him more jealous if there was a guy in the picture with you." Tripod now facing her I picked up the flash button and moved my way into the frame.

Hands still on the wall ass still in the air I placed my hands on her spreading her cheeks so her puckered little asshole said hi to the camera, click* Firmly slapping her ass cheeks till red, click*. Now sliding the dildo in an out of her pussy taking pictures as it entered and exited her.

"Does it feel good to get back at Jack baby?" Now fucking her quickly with the dildo, click* click*

"Oh yes." Cocking her head back moaning, "he could have been the one doing this." Click*

"But he's not." I said pulling out the dildo and making her face me, "how do you feel about that?" I questioned pressing the wet head of the dildo onto her lips, click*

Taking the dildo in her mouth, click*, "I'm happy it's you helping me get back at him." Giving me a hug.

"I'd never hurt you baby." Hugging her back facing her away from the camera then spreading her ass, click*

"I don't think I want to have sex ever because of him." Tears welling in her eyes once again

"It's okay baby, you'll find someone." My fingers spreading her pussy for the camera, click*

"I doubt it." Sniffling away her tears

"You will." One hand wiping her eyes the other in between her thighs fingering her "like you said, it'll happen in the moment."

"I guess. I'm glad it's you taking these pictures." She said smiling at me, "I know you won't hurt me." She moaned, "all of the guys my age or men I know would have tried to fuck me a long time ago or would have suggested getting back at Jack by having sex with them."

"Well, you can trust me." I said jamming 2 fingers into her gripping hard to her walls holding her in place, "you know you can trust me."

Moaning loudly then whispering in pleasure "yeah."

"Now let's get you into another costume."

Giving her another costume to change into she walked into the bathroom to change. Secretly replacing the dildo with the next size up, one almost as thick as me but this time 6 inches. I also pulled out another one of those horny pill for good measure, dissolved it into a cup of water, knocking of the bathroom door to hand to her. Watching her walk out of the bathroom dressed in the DreamsGirl's Triage Trixies Nurse set was jaw dropping.

"Thanks for the water."

Her body fit it like a glove. Unlike the Maid to Please set this one had see through white garters that rested half way up her toned thighs. Red straps connected the garters to a stretched opaque white jersey that arched around her naval hip to hip, showing off a camel toe covered by translucent white G-string with red outlines leaving just enough imagination to the mind. A red ribbon stitched erotically up the length of her stomach bowed up nicely just below her breasts molding the jersey to her slim toned hourglass body pushing up and accentuating her breasts magnificently.

Spinning around happily showing off her new costume, the back was unlike the front. Transparent white fabric covered her back showing off toned muscles. Draped tightly over the rise of her ass barely covering a white tight bubble butt was a frilly red skirt that stopped less the halfway down her ass, held in place by red straps that connected to her garter from the back. To top it all off she was wearing the nurses cap, its when I saw her that my cock stood full mast. Thankfully I was covered completely by the thick baggy fireman pants that left no hint that I had an erection.

"Perfect." I gawked pulling her in by her hand bending her body over my left arm while the right hand explored her ass, "Lena baby, if I'm ever sick in bed could you babysit me while wearing this?" Click*

"Maybe, if you ask nicely." She giggled as I landed a nice firm palm on her ass, click* "if I didn't know any better I'd say you'd want to fuck me." Sounding almost concerned

"What makes you say that" reaching both hands around to spread her meaty pussy in my hands bending down to lick her asshole, click*

A surprised shriek "maybe it's just me."

"Yea, I think it's just you." Lightly slapping her mound, "sit on the bed."

Sitting on the bed legs bent under her leaning on her right arm to one side. Her breasts threatening to pop free but were held down by thin fabric fabric, hard nipples popping though. Taking more pictures in various poses getting her in the mood she eventually was kneeling face pressed to the bed ass in the air facing the camera, click*.

"Lena hun, can you play with yourself while I take some pictures?" Positioning the tripod behind her.

No response left her but she reached up between her legs and started massaging herself through the fabric.

"Perfect baby." Click*, I said stroking my cock through my pants, "just like that, now move the G-string to one side."

Playing with her meaty pussy, her exploring hand now massaging fiercely as she tried to bring herself to an orgasm, click* "Lena, have you tried sticking a finger in your ass?"

Pausing her hand for a moment "no, I've never tried." Raising her other hand to her anus

"Give it a try, it'll look really sexy." Hand down my pants stroking my cock watching the live show, "then I'll give you back the dildo."

Moaning to the idea of the dildo she pressed her index finger slowly into her virgin asshole. Her other hand now quickly fucking her pussy.

"Just stay like that for a while, if you feel you're about to cum slow down." Switching the camera to video. "Remember we have one more costume to try." Pressing record

"Mmmm, you still have to wear another costume for me" she said between her moans.

"Okay hun, I'll pick one that will go well with your next one." Secretly unzipping my pants to pull out my cock so I can freely masterbait behind the camer, "we'll match and put on a play for the camera"

"Okay. I can't wait." Fingers plunging in and out of both ass and pussy! "Jack will be so jealous seeing me with someone else."

"You think so?" Moving into frame with my cock in hand I bent down angling her so her pussy was still in frame as I spread her pussy getting ready to eat

"Oh god yes." Voice high pitched pulling her fingers out "especially when it's with someone like you."

"Someone like me?" Licking my tongue up and down her pussy

"Whatever you're doing feels so good." She said pressing her ass deeper in my face

"Has anyone eaten you out before?" I asked in between licks

"No, jack never ate me I never let him, but I gave him head a couple of times."

"Do you want me to stop?" I said flicking her clit with my tongue.

"Please no." She moaned sticking her finger further deeper into her asshole "this feels so good."

Eating her pussy was fun, to say the least. Her virgin pussy had never been through any good experience and I was going to let her experience everything. Her pussy tasted sweet with a light ting of sour. Stimulating her clit with one hand while fucking her pussy with my tongue I pulled out the dildo.

"Do you want to use the dildo now?" Rubbing the new dildo up and down her slit

"Yes." Sounding desperate to keep the pleasure going

"Lena, I'm curious." Pressing the thick dildo against her pussy "how big was jacks dick?"

"He wasn't that big he was below average. Probably around 5 inches or less and not that tick."

Penetrating her with the new dildo she gasped deeply, shocked at the new girth pushing its way into her "that sucks. You never got to experience a real mans cock."

"Oh my god it's so thick"

"But with how sexy you look I bet that will change soon." Pushing the full length of dildo into her.

"If a dick actually feels this good!" She moaned trying to keep her voice down "I hope so oh my god"

Fucking her hard with the dildo I replaced her thin finger in her asshole with my thick finger and she screamed loudly in pleasure as I started to massage her anal walls. I didn't do this for long I wanted to fuck her soon so I pulled out the dildo and stood slapping my cock across her ass, placing the head of my cock against her entrance making sure the camera got a good view.

"You still think I don't want to fuck you?" I said rubbing up and down her slit

"I think you're just having some fun." She said pressing herself into me, thinking she was still pressing herself into the dildo

"After we get back at Jack," spreading her pussy with my thumbs getting ready to penetrate her, "would you want to do this again?"

"Maybe." Desperately trying to get the dildo back in pussy, "I think this is a one time thing but I know you won't force me to do anything I wouldn't want to."

Hearing her say those words I responded "lets change into the final costume" putting my cock away thinking 'she's not ready. Just a little more.'

Moving the tripod to side wall of the room satisfied that when the camera was mounted Lena could be seen standing in front to the bed. Taking the camera with me to the bathroom to change I told her to call for me when she was ready.

Wearing the police stripper outfit was uncomfortable. Wearing tight pants was never something I did because of how they squished my family stones. The good thing about it was there was a hole where the cock would be, like front assless chaps. You would wear special shorts underneath that covered your junk, when you put the pants on together they looked like one piece, but undo one button on the waistband of the shorts and your cock would flop free.

The two things I liked about this outfit. The first being that the front of the shirt was a 'V' that started at the belt line angling upwards showing off some abs and bare chest just covering the nipple. With my body I looked good. The second thing was that when you had on both the shorts and the pants the padding on shorts made it look like you had stuffed your crotch with a towel, making it look like you were wearing a baseball cup underneath. I took out the padding so that it was just the shape my cock pressed up behind the stretchy blue fabric. I was flaccid now but when I had an erection... man I couldn't wait for the surprised look on her face.

"John? Im ready."

What I saw when opening the door was beautiful. Standing there in the middle of the room was 18 year old Lena in just a skin tight collared white translucent mesh halter crop top that covered a little more than half her breasts showing off the bottom half. A short green plaid tie fell the length of the shirt and on either side poking through the fabric were pink nipples. Her glasses went well with this sexy school girl look.

There was nothing between her chest and hips, she was just showing off her slim hourglass form and a toned stomach. Hugging her hips was an extremely short miniskirt that matched her tie, it was just long enough to keep her pussy hidden from view. Cut down the side only tree snap buttons kept it from falling down her bare legs. Turning around to see a thin pice of mesh fabric wrapped across her back giving the illusion she was wearing a bra. The skirt fell snugg across her ass falling just enough to cover the majority of her, all you could see was her thigh gap. She was definitely Dreamgirls Extra Curricular Cutie and I was going to teach her all sorts of new things tonight.

"It was a two piece so it was easy to put on." She said shyly like this costume was the one that made her uncomfortable

"That's fine sweety. You look like any mans dream." I said soaking her in "young, hot, sexy, tight ass, beautiful breasts, perfect." She blushed at the last word

"You really think so?"

"Baby, I know so." Pulling her in for s long sensual hug that she didn't shy away from. Leaning into me more I ran my hands up and down body getting familiar with the curves of her hips, the small of her back, the rise of her ass. Turning her around I held her against me while my hands continued to explore her body, her firm breasts fit perfectly in my hands, running my hands down her stomach I could feel the hint of abs but looking at her I would never have noticed.