tagFirst TimeAshley is Babysitting

Ashley is Babysitting

bystllrnng47©

Ashley:

Another night of baby-sitting. I love this kid but it's always on the nights my friends are doing something fun! Tonight my roommate is throwing a party. Oh well it's easy money and his dad is super sweet and handsome. Besides parties are only fun to look forward to anymore.

Charlie is asleep and I'm just trying my darnedest to stay awake. His dad is later than usual. I already tidied up the house and kitchen to keep myself busy. Now I need to rely on a book to keep me up. My eyes feel so heavy...hmm I'll just close them for a few seconds. Mmmh that feels nice.

Pete:

Ahh can't wait to get home and go to bed. This work dinner went way too late. Fatigue is a powerful feeling. It's hard to think of anything else when it gets extreme like this.

I park my car and head inside. I don't hear anything. Maybe Ashley fell asleep? I look in the living room and sure enough there she is on the couch with a book on the floor next to her. She must have dropped it. Her spaghetti strap has fallen to the side and I know it's immature but I feel something other than my fatigue when I see her bare shoulder leading to the top of her breast. I guess that's what happens when I go this long without sex. She is very beautiful with soft curves, pale skin and curly dark hair surrounding the sweetest face with glasses. I regain my composure before waking her up but than stop myself. It is so late and I just can't bear to wake her up to go home at this hour. It feels wrong. I gently remove her glasses, cover her with a. Blanket And melt into my bed without another thought.

Ashley:

"Morning Ashley!" Charlie's smiling face is next to me on the couch.

"Morning? What? Whoa!" I slowly sit up.

Charlie gives me a hug and I put on my glasses. Pete walks in with a shy smile. He's in a robe and I can't help but look his large body up and down real quick. I really like how that robe looks on him. I blush and look down.

"Morning Ashley. I'm sorry I didn't wake you up last night. It felt wrong at such a late hour. I hope that's ok."

"Oh yeah it's fine. I'm just sorry I fell asleep and put you in that position."

"Oh no don't be. I got home so late last night. I truly don't mind at all."

I smile as I stand up. "Well I guess I'll get going now."

He handed me my money. "I did make enough coffee for 2 if you would like some. "

I smile appreciatively. That sounds really nice but I really don't want to intrude.

"Oh yeah if you really don't mind"

"Of course not" he pats my shoulder before going to the kitchen.

"Can I play outside now?" Charlie asks.

"Sure thing!" Pete replies from the kitchen.

Their backyard is totally childproof and Charlie is old enough that we don't really need to watch him out there.

Pete comes in with 2 coffees and Sits roughly a foot away from me on the couch.

I do find him attractive and so sweet and besides him being a father at the daycare, there's really no reason we couldn't be romantic. I guess I just don't really know how to go about it. I speak up.

"Charlie had a great night."

He chuckles then looks at me, "I'm happy you stayed"

I feel heat in my cheeks and look at the ground, smiling. We both sip some coffee.

"This is so good." I say.

He puts his arm around my shoulder and squeezes.

I tell him "I like you, you know". I've learned from experience that it's so much better to say what you feel.

He looks a little surprised but happy. "I like you too, very much."

"Daddy I saw a lizard!" Charlie yells as he rushes into the living room.

Pete removes his arm from my shoulder.

"I'm gonna go find another one!" he adds with a jump in the air and runs back outside.

Pete and I look back at each other and giggle.

"Continue?" He asks me.

I hesitate a second before nodding my head eagerly. I scoot closer. He leans his head down and softly caresses my cheek. When he kisses my lips, I feel a rush of warmth between my legs and I melt. I lose track of time. He rubs my thigh all the way up to my bottom as he gently kisses me. I can see he has a boner.

"Oh" I pull back without thinking.

"Sorry"...he chuckles, his face all flushed... "We should probably stop now".

"Charlie could walk in." I look toward the yard nervously.

"You're right. That was inappropriate." He shakes his head shamefully as we sit back up.

"Hey it's ok." I rub his shoulder, "I really like...doing that with you."

He looks down at me and smiles, "me too..."

Pete:

I want nothing more right now than to take Ashley to my bed. And she actually likes me. I still could mess things up though. If I move too fast, I might scare her off. She seemed a little unsure when she felt my erection on her leg. Yes I will take things a little slow.

"Ashley will you have dinner here tonight?" She takes my hand in hers and smiles.

"Sure. I would love that." She rises to give me a soft sweet kiss. I wrap my arms around her waist and hold her to me, feeling her soft feminine form, kissing her neck and ear lobes. I feel her melt into me a little. I wonder if she's not very experienced because it doesn't seem to take much to get her excited. I move back to her sweet lips.

Charlie walks in and sees us. He gasps.

"Are you kissing?"

I answer frankly. "Yes Charlie. We were kissing."

"Why?"

Ashley answers. "I like your dad in a romantic way and that's how I show it."

I adjust my pants when I think of all the ways Ashley can show me she likes me.

Charlie giggles and runs up into his room.

We kiss some more...and some more. She's a really good kisser. So sweet and loving. She's moved up to my lap now and I slowly disengage from the rest of the world around me as I let my hand explore under her top. Her breasts are so soft and squishy with perky nipples. It is very hard to stop at this point.

Ashley:

Pete and I are getting pretty close on the couch until my phone rings.

My mom...

"Omg whoa." I take a deep breath before answering. I'm still straddling Petes lap and I get off as if my mom can see.

"Hi mom"

"Hi lovey, just checking in...making sure you are still taking Henry to his game"

"Oh yeah of course" I say as my hand smacks my forehead in frustration. I had completely forgotten. "I'll be there to get him in 15."

I get up from the couch, feeling a little ashamed but then reminding myself there's no reason to be. There's nothing wrong with being sexual with someone I like. I'm just not used to it.

"Pete, I Have to go drive my brother to his soccer game. I completely forgot. But i would still like to come for dinner. "

Pete laughs. "Oh Sure. Dinner will be at seven. Lasagna!"

"Oh my life is good" I beam as I get my stuff together. Pete walks me to the door. We hug and I stand on my tip toes to give him a kiss on the lips.

Pete:

As soon as I shut the door, I go finish myself off in the bathroom. I want to be able to relax a little and hopefully last longer if we do have sex tonight.

I check my bed side drawer for condoms. I feel like a teenager again. Yes that's how long it's been. I've just been a little deflated since my wife left me and Charlie. I find it easier to fully focus on work and parenting. Those are both full time jobs anyway. Then just rub myself off when the mood strikes and time allows.

But Ashley has been baby sitting for over a year since Charlie started attending the daycare she works at. I've liked her from the start but simply didn't see it as a possibility. I'm no hunk, just average face with large build. She has always seemed very friendly but a little distant. I'm alright looking but she's a very cute girl and at least 10 years younger. Who would have thought all I had to do was offer her coffee to win her affections?

I turn on the shower as I get ready for a typical Saturday with Charlie. Have breakfast, Go to the pool, have lunch, read stories, nap, snack, then he can help me with this dinner, maybe.

Ashley:

"Hey Henry. Hop in. We're running late!" I say as Henry makes his way to my car, dragging his gear behind him.

"I don't want to go!" He whines.

Henry is 7 years old, 15 years younger Than me. I have traits of an only child as well as an older sister. I love the kid to death and it's clear he looks up to me. I like that.

"Part of growing up is doing things even when you don't feel like it. If you only do things when you feel like it, nothing gets done and skills aren't built. The happiness you feel as you get better and better is so worth the frustration of having to get off your butt and do something you don't feel like."

"I still don't want to go" he moaned, crossing his arms.

"But?"

"But I'm doing it anyway"

"That's right Henry. You got this."

"Are you gonna watch my game?"

I hesitate. I had planned on only dropping him off and picking him up and just hanging around the house but after that pep talk, I feel like I should stay and watch.

"Sure Henry. I won't be able to stay every time. But today works for me."

Pete:

"Charlie what kind of feet are we using here?"

"Walking feet!" He quickly switches his pace.

We swim for a while. He came.

As soon as we put the lasagna in the oven, the doorbell rings.

I open the door and see Ashley with her gorgeous curls Ina half pony tail, her glasses framing her gorgeous full cheeks, yellow halter top dress that stops mid thigh. I'm still a little dazed at the idea of this beauty being interested in me.

"Hi Pete. Can I come in?" She asked. I didn't realize I'd been staring.

"Oh yes...sorry." I chuckle as I open the door wider for her entrance.

"Are you guys gonna kiss again?" Charlie asks.

I answer, "not in front of you, don't worry" I see that Ashley is blushing.

"Ashley would you like some wine?"

"Yes that sounds perfect!" She smiles big.

I guess we're both a little nervous.

As we wait for the lasagna, we play chutes and ladders with Charlie and have a blast. Charlie clearly loves Ashley. I feel pretty awestruck myself. We eat dinner and Charlie does a good job not making a mess and Ashley is on her second glass of wine.

"Charlie time to brush your teeth and go to bed." I say, feeling a bit antsy, ready to be alone with my date.

Amazingly enough, Charlie listens and when he's all tucked in bed and we've closed his door behind us, Ashley takes my hand and leads me to my bedroom and I follow willingly. I close the door. She wraps her arms around me and kisses me so sweet and lovingly as she stands on her tiptoes. I gently pick her up and lay her down on the bed. She seems more relaxed now and eagerly wraps her young curvy legs around me as we kiss. I remove her dress and underwear but leave the sexy heels on. I can't believe how much I want her. Her naked body is gorgeous and she wants me of all people. Her cheeks are so red. I remove my clothes and we start kissing again. I lower my head and softly suck and kiss her breasts.

"Mhh I like that." She coos as her hand reaches my balls. She squeezes them real nice. My pre-cum is wetting her thighs at this point.

I feel her sopping wet sex and touch her gently, having figured out she's not very experienced. I gently spread her wetness around making gentle circles around her clit.

Ashley: I think I'm in heaven and I don't ever want to leave. Pete is touching me and I think I'm gonna cum if he keeps going. He does and I do. Hard. I hope I wasn't too loud. I take a moment to catch my breath, tears streaming down my face. I had done that to myself before but never had it done to me. It was at least 10x better with Pete. He embraces me while I calm down.

We kiss some more on our sides and Pete's proportionally large penis swiftly slides into me. He exhales sharply.

Pete:

I can't believe how hard she came. Her gorgeous tits bouncing with her heavy breathing. Her pussy is so gorgeous. It just seems too good to be true but once I enter her, it's even better than I thought. Her slick walls thoroughly massage the length of my shaft as I pump her slowly. By the time I realize I forgot a condom, My cum is oozing out of her pussy.

I don't say anything though. She seems so blissful. Her soft young body embracing me as she drifts off to sleep. I really like having her in my bed with me. Having sex or just sleeping. It feels right. I've been lonely too long and she is an angel. I wrap my arm around her and kiss her shoulder softly, then turn out the light.

The next morning, Charlie bursts into the room. He always gets up earlier than me. Ashley's bare back is exposed and I automatically cover her.

"Whys she in your bed? Are you gonna get married?" He whispers.

I am sick of trying to explain something like this to him and order him out of the room. He puts his head down and obliges.

I feel a little bad but also really want to be alone with Ashley. I want to be intimate with her again, very badly. But also don't want to be pushy.

I gently stroke her back as she stirs awake. She lifts her head, her rosy cheeks so sweet. She smiles at me and kisses me ever so softly. She does it again. Hmm. She seems in the mood. I take her face in my large hand and kiss her a little more firmly, pulling her closer, her warm breasts pressing against my chest.

She breaks the kiss and looks a little crestfallen.

"Pete...I'm having feelings...and I don't want to get hurt." She begins to cover her chest. I put my hand on her arm trying to comfort her. "I'd be lying if I said I wasn't too."

She looks up, "really?"

"Yes...I mean I've known you for a year. You're an all around lovely young woman. I just didn't think there was a chance. I mean look at me. And look at you."

She seems to get more comfortable, Cuddling up to me. "But I always felt attracted to you. I like how big you are. And sweet and smart and funny." She giggles.

"Mhh my ego is loving this." I chuckle and bring my face down to hers, kissing her tenderly. She responds warmly, climbing on top of me, kissing my lips eagerly. She slowly makes her way down to between my legs taking it in her soft full mouth, her warm tongue exploring me. She tenderly squeezes my balls as she loves me with her mouth. I don't think there's anything that could break me out of the hypnosis of such loving fellatio.

I release into her mouth and she eagerly swallows.

Report Story

bystllrnng47© 9 comments/ 60380 views/ 22 favorites
1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartitalktomyselfyesido, excon8974 and 20 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous08/25/17
by stllrnng4712/12/16

Thanks for feedback

Thanks for the feedback. I will definitely take the 'more details' into account with the next story. I tend to like leaving some things to the imagination as mine is very strong when it comes to sexualmore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by clitlicker4u12/03/16

Makes every older guy want a baby sitter

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous11/30/16

Heep going

Good use of dual POV, and plenty of background details. But, where is this going?

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous11/29/16

Where's The Story?

Sketchy. More like a story line/outline than a story. You need to flesh this out, no pun intended.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 9 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel