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?"

Ava tells me, "If I was uncomfortable silly, I would not be in your room next to you and also have all my clothes off." She says with a sweet laugh. I look her in the eyes and laugh too. Now its time to see what I remember.

I inhale and let out a large breath. I can tell Ava is a little scared, despite how much she trusts me. To be honest I am almost as scared as she is. The last person I made love to was Maria towards the end of her pregnancy. So it had been a while. The other thing is I wondered what Maria would think about this? As I gazed on the young nubile female laying beside me I think if Maria was here she would have been munching on that small pussy already and enjoying me watch her do it!

I whisper to myself..."For Maria"...as I I begin to kiss Ava behind and on her ears and down her soft tiny neck. My hands wander to her breasts and massage them. Ava's mouth is agape with breathy sighs as I feel my skills slowly come back to me.

Ava holds my arm and rubs my ticklish side. I tell her, "touch me, I don't care where. Show you are interested in me, just don't lay there."

Ava complies and uses her small hands to explore me. Our bodies are so different that my hair covered flesh is all new to her. I make my way south and feast upon her breasts. Let me tell you, "like my father before me," I am a breast man through and through. I hold each in my hands and I can barely hold them. My fingers are spread out all the way and still more breast flesh escapes me.

Her breasts are pale from lack of light and there is not a blemish on them. Round large areolas surround pencil eraser nipples that are hard, and as I find very sensitive to the touch of my mouth. I suck in most of one breast and lick the nipple at the same time and then do the other. Ava arches her back up and presses them against my face. I pull away and make my way further sound on her body.

I lick and suck down from her breasts and continue over her stomach and navel. As my mouth goes towards her sex between her legs, Ava tries to close her legs in embarrassment. I look up at her flush face, she's hold her breasts in her hands and pulling on her own nipples, as she nods yes and whimpers through closed lips. I gently push her legs back open and finally reach the prize.

Ava has no hair around her small pussy except a sparse growth of brown hair that barely grows on her pubis above her moist opening. Her feminine flower is open and glistening. It's as small and delicate as she is. Small lips surround her labia and the hood of her clit sticks between them. Looking downwards her pussy goes to her taint and her puckered anus winks at me all pink and rosy. My god! Her glistening womanhood it takes my breath away. Ava looks at me with worry. I look to her face and say as I go in for my first taste of her sex, "you have no idea how lovely you are! Let me now show you!" I ran my tongue up from her asshole and over her clit. Ava grasps me by my hair as she cries out and holds on tight. She knows shes in for a ride.

Ava tastes of sweet honey and I don't want to miss a drop. I slowly tongue her opening as I insert one finger inside her. I move it in and out in times with my mouth on her clit. Shes oozing girl goo and becoming extremely wet. My solo finger is joined by another as she eagerly accepts my fingers by humping back into them, crushing my nose into her clit.

I move my fingers in a "come here motion" against her g spot as I suck on her very hardened clit. Ava cries out and muffles her scream in a pillow so as not to waken Leia. I pull away and have her get on her hands and knees in front of me. My 7" cock is very hard. And its pointing at her fore head. I ask her if she knows what to do? "A little," she answers. "My best friend Yasmin told me how."

Trusting in the faith of her unknown BFF Yasmin, Ava takes my cock in her cold hands and begins to jerk it off slowly in front of her face. She looks at my swollen purple cock head and licks it up the front of my slit. She tastes my musk of sweat and body soap and likes what she tastes. Pre-cum has leaked out and as she sticks the whole head between her lips she sucks it away. The look of her small mouth taking in my cock almost had me blow my load right then and there. Some how I held back.

Ava sucked in and out on my cock head and as she gained my confidence she took more and more into her mouth. I was quite impressed by her amateur skills already, I had my hand on a tuff of her hair as she went down on me. I called her my "sweet belle who is taming the beast!" When all of the sudden Ava pulls back, looks at me, directly in the eyes with a devilish look on her face. She then preceeds to deep throat me until her tiny nose tickled my pubic hair. I let out a cry of shock of my own and groan happily as she takes all of me in and out of her mouth. Shes caressing my balls now and I can feel them in her small hands be gently juggled like she's done this before.

With a cry of frustration I with draw mu hard slick cock from my sweet cocksucker. She looks at me with hurt in her eyes. I stand her up and lay her on the bed. I come between her legs and line my cock at her moist opening. "Ava," I ask. "Are you ready for what happens next?" Ava nods her head eagerly.

"This might hurt a bit, but will feel real good soon." Ava nods her head again and laying on her back, spreads her small legs wide, exposing herself fully to me. I almost cum right there seeing her body spread eagle and waiting on me. I get between her legs and insert my cock head between her pussy lips.

"My god!" I say to myself. Her moist opening hugs tightly around my cock head. I slowly ease forward and come back. Ava grimaces, but like a trooper urges me on with her eyes. Her mouth wide open, breathing heavily. I go in further and get my 7" cock halfway in before I feel her barrier. Ava cries out in frustration and pain. Mid way in I look down at her, "Are you sure, Ava?"

"Yes Greg, break it, I am not afraid. I am with you! Fuck me Greg!"

I pull back and then slowly push my way through. Ava cried out in half pain that turned to pleasure as I bottomed out inside her with 5" in. Slowly I saw into her. Ava's breasts begin bounce against her chest, which makes my cock get harder. I increase speed and Ava spreads herself open so I can go deeper. Her pussy is so tight but so wet I am gliding in and out fairly well. Ava is a natural. I surprise her by pulling out. My cock makes a popping sound coming out of her. Ava looks at me like I betrayed her.

I laugh at her innocence and pull her up on her hands and knees. "Ava, trust me you will like this," I say as I enter her pussy from behind. I hold on to her small waist and watch as her breasts sway with each of my thrusts. Ava finds she can have some control and pushes back against me as I thrust into her. The first time she did this I felt the head of my cock tap her into cervix (I could never do that with Maria). Ava was breathing heavier and I felt her pussy contract around the girth of my cock. I was feeling my balls tickle and knew this would be a big one.

I slow my thrusts and tell her I am going to cum. I feel her start to release as my cock and crotch gets soaked with her juices when she tells me, Don't you dare pull out! Pump your seed in me! I want your baby in me!" I hesitate and then figure, "what the hell!" I slam back into her as she pushes back against me and I feel my balls get ticklish as I cum inside her for what feels like forever. I groan as her pussy squeezes every ounce of semen out of me. We collapse on the bed all sweaty and covered in sex juice.

I hold her to me and kiss her all over. "I love you Ava!"

"I know," she says as we lay entwined on a very wet bed.

We awake before dawn and I show her how to 69 and and find she loves the reverse cowgirl. We crawl out of bed sore and satisfied and have enough time to strip the bed and take a shower together before Leia comes downstairs in her Elsa PJs and hugs both of us before taking her Captain Crunch over to the TV to watch Frozen for the 1,000th time. Ava and I kiss on the lips and join Leia on the couch in each others arms. Leia looks back at us like its no big deal and watches her movie.