Adventures in Babysitting Ch. 03: Ava

My name is Greg. I am a widowed single father to my 5 year old daughter Leia. You might know my parents Gary and Cassidy Newman. I know that in High School all the staff seemed to know me before I ever stepped foot in the building. My wife Maria died during childbirth and I have raised Leia, for better or worse on my own.

My parents helped out a lot in the beginning but made it known that in a crisis they would always be there but it was up to me to raise Leia. It was a good thing before we married I had finished college and had a decent job. Also Maria and I set up wills and life insurance so while Leia and I would rather have her mother with us, the benefits we received from her mother’s death paid off our small home and set up a college fund for our daughter and provided small monthly payments to subsidize my income.

We were doing well on paper and Leia and I loved each other dearly. But after 5 years of lacking adult female companionship let alone physical intimacy I was more then ready get back into the dating game again. My aunt Vanessa, who is an Assistant Principal at Edgewood High School, had the in on students looking to earn extra money baby sitting.

That was how Ava Miller came to us. Ava is just over 18 years old. Stands maybe 5’1″ and hides her full feminine figure under baggy hoodies and sweat shirts. Her chest has to be at least a DD, but on her small frame looked like she would fall over if pushed from behind. Her ass is curvy, and like her breasts, looks almost too large on her small frame. Ava has long brown hair that hangs loose in front of her eyes, like Violet from The Incredibles. Shes very very quiet and is a spitting image of a live in person Belle from “Beauty and the Beast” and mainly reads books or comics for fun.

Ava came to us six months ago. I started going out playing D&D once a week and tried dating here and there which turned out to be an absolute disaster. I am very up front about my daughter and a lot of these woman on tinder and plenty of fish are just down right crazy and more child like then my five year old. No way was I sleeping with any of them. And even if all I wanted was a “piece of ass” I kept my raging hard-ons to myself and watched Porn Hub or read Literotica to relieve myself later.

Needless to say Ava became a regular at our house. Our small home was big enough to give Ava a bedroom to use if I was out too late or went away on business for her use only. In all of my life dealing with the stresses of work and parenthood I guess I just put my love life on the back burner and hoped no one would notice my loneliness. Well of all people other then my parent’s and my sister, Ava, noticed me beyond being just a thirty year old parent and employer. One evening she showed me how much she loved me and helped me find myself again.

It all started when I got home late from a bad date. I sulked into the house dejected and defeated. The gal was decent looking and not crazy about kids or any sort of responsibility in life. “Where the hell are the normal and nice girls,” I said aloud as I took off my coat and shoes by the door.

Ava came out of the kitchen, drinking a glass of milk. “Have a bad time?,” she asked.

“You said it…” I said as I related the failings of work ethic and common sense in woman today who look to The Kardashians and Real Housewives for the way they should act.

Ava just laughed softly and nodded as I half jokingly wished her and I could date, as next to my mother, I could think of no other woman but her and my dead wife who were left that were true woman of character anymore.

For some reason Ava blushed a deep red as I looked at her for the first time not as a kid but as a real live woman. She had just turned 19 the week before.

Ava was wearing a summer weight yellow silk jammies. They had a sleeveless top that showed a good bit of cleavage between the lacy part of the top and the top hugged her in such a way that she was all woman underneath. The shorts ended at her thighs a good six inches from her knees showing the slight curve of her small bubble butt ass cheeks. Ava’s hair was loose as always and freshly brushed. Her small brown eyes peaked through her long loose hair in a sexy manner that I was sure she didn’t even mean to be doing. She was holding a well worn copy of “Les Miserable s” by Victor Hugo against her breasts.

Ava held my hand and we walked upstairs into my master bedroom. We laid down around 11:30pm that night and just talked plutonically for hours. By this time I had changed into gym shorts and a t shirt and didn’t care of Ava saw me change or not. As I was getting sleepy I told her she could stay or go bedroom wise. I was closing my eyes and rolling over on my back when I thought I heard her say,”I thought you would never ask.”

Next thing I know I feel her small arm drape over my chest as her small body wiggles close to me. I hear her call me her, “teddy bear” before I drift off to some well needed sleep.

I regained consciousness a few hours later because I could have sworn Leia had crawled into bed with me, as she was prone to do but then I realized that the person next to me didn’t have a bubble gum smell to her hair. I opened my eyes to find Ava snuggled up to as tight as she could go. Now I will admit that like my parents I carry a few extra pounds on my 5’7″ frame and I’m just as bearded and hairy as my father.

I roll over towards her and watch as her full chest moves up and down with her soft breathing. The bedroom is a little cold, as i like it, and I can see her erect nipples hard through her silk top. I reach over and hold one of her breasts in my hand. My hand barely covers it and her nipple pushes against my palm. Her large lips part with a sigh. I continue to softly caress her as she sleeps on her back.

I go from one breast to the other. I massage her breasts and pinch her nipples lightly. Ava begins to squirm a bit and I move my hand away. Ava lets out an exasperated moan and I put my hands back on her breasts. A shy smile comes to her face as I continue exploring.

I move my hand on downwards over her stomach stopping at the waistband of her bottoms. I run a finger along the band and then slide my hand down her quad and caress her legs. Her legs are smooth and freshly shaved judging by the lotion I smell on them. I tickle the inside of her knee and she wiggles and closes her legs. I run my hand along the inside of her leg nearest me and stop at the bottom of her silk shorts and feel her quad tense up as she slowly parts her legs for me.

I’m beginning to think Ava is not as asleep as I thought she was. I continue rubbing her upper thighs and as I head upwards I keep going and open hand her pubis lightly outside her panties. My hand came away slightly wet.

I smelled my hand and tasted her sweet sex. My cock began to grow in my shorts. I brought myself up on my elbow and lean in and kiss her on the lips. Her lips part as she sticks her small tongue in my mouth as I play with it with my own. I hold her face and look into her eyes as I pull away from kissing her. She sees me smile as I embrace her and continue kissing her all over.

Her hands begin to wander all over my body as we embrace. Her small delicate hands run through my hair on the top of my head and feel the sides of my face across my short beard. She touches me because I am the first man who has ever let her touch him. Her hands wander down the muscles of my arms and across my hairy chest under my shirt. Her hands pause at my shorts. I tell her, “it’s ok, go ahead,” as she reaches into my shorts and takes hold of my half erect cock.

Her hands are cold but warm quickly as she feels me harden in her grasp.

“Do you trust me Ava? You know I would never hurt you. But if you would let me I can show you a whole new world.”

Ava nods slowly and says, “Greg, I want you. I’ve wanted you for a long time.” Ava says, with tears of happiness in her eyes. “I want you to be my first.”

I tell her that “I’ve wanted her too,” as I slowly take off my clothes.

Ava looks at my dad bod in awe. I can tell she likes what she sees.

“Your turn,” I said as she slowly pulls off her top releasing her young firm DD breasts which drop and settle with a slight wiggle. She raises up her butt and I help her slide off her bottoms and panties to reveal her pale skin and little brown haired pussy.

Thoughts of that meme that goes something like “Prince in the streets, Beast in the sheets,” crosses my absurd mind as I smile and chuckle at my own joke. Ava try’s to cover her nakedness. I ask her, “Are you ashamed of your body?”

She nods yes. I ask her why? She crosses her arms over her breasts and keeps her knees closed. “Because from 6th grade onwards I have had these, she holds up her very ample breasts and covers them again, and I never heard the end of it at school from jealous girls and horny boys!” Ava is near tears. “It was easier to hide, than be open. So I hid.”

I kiss her softly on the brow and look deep into her eyes and say to her. “Ava. You are more woman than any of those “girls” will ever be and more woman then those “boys” ever deserve.” I continue. “You are all woman where it counts, which is a whole hell of a lot! You are desirable to men as well as woman.”

Ava perks up at this in surprise. “Maria appreciated other woman from time to time. if I was a good boy I got to watch. If I was really good I got to play too!” Ava’s eyes went wide.

“Anyway, what I mean is you are truly offering yourself to me but really I am honored that you are even here with me in my bed. I swear I may be a little out of practice but I promise to show you everything you desire and hopefully much more.” Ava looks at me in silence but she holds me to her and we kiss deeply. She holds my face in her hands. Her happy tears drop across her chest and mine. I just hold her tightly.

We break our embrace and I look at her with love in my eyes. I am really worried because I can see she trusts me. I desperately do not want to let her down. “If you are ever uncomfortable please tell me and I will stop?”