Chy, the Shy Babysitter

Chy, she was my son's babysitter. 

She's about 5'5" and 120 pounds, with blonde hair and a few freckles. She has beautiful blue-green eyes. 

Really a sweet girl. Her 18th birthday was just three weeks ago. She was rather sheltered as a kid and didn't get to experience things like I did growing up. She spent most of her time as a young teen taking care of her siblings. She's now enrolled in an online college full time and works from home as a transcriptionist..

Chy was also my new neighbor. Only a driveway separated her house from mine. Her bedroom sat facing mine, and the perfectly placed window in my room allowed me to occasionally meet her eyes as we both looked out.

I would always acknowledge her whenever I saw her outside, coming and going. She would smile, but not too much, as I think she was embarrassed of her braces. Though I hadn't mentioned it, I thought they were cute on her.

Whenever I was outside with my son, she would make it a point to come out and play with him for a little while. She always grabbed his attention, and he just adored her. How could he not, as she often brought him over a snack or some toys for him to play with. 

As the weeks and months passed on, Chy had become familiar with my daily routines. When I left and came home from work, when my son was at his mom's; heck, she knew when I went to check my mail.. When I would return home from work, I occasionally noticed her peeking through her window as if I didn't notice.

It became apparent to me that she was attracted to me, and not just because the neighbor across the road may have mentioned something of the sort. It was the constant run ins with each other during my normal day to day. She always found an excuse to come over and talk about anything she could or ask me some simple question that she probably knew the answer to. Honestly, I didn't mind because I really enjoyed seeing Chy. She always wore clothes that would catch my attention but still leave enough for the mind to imagine. From her perspective, she could probably see that I found her attractive as my eyes traced her body from her pretty painted toes all the way up to her cute little nose.

I was sitting on my porch swing as Chy got home, she sat down right next to me, and we started chatting. The conversation got much more personal compared to most of our interactions. We talked about her family, friends, travel, and of course, my son. 

I briefly mentioned that I didn't really like the day care in which my boy was enrolled and that I was considering hiring someone to babysit while I was working. 

Chy immediately volunteered for the job. In fact, she not only offered but insisted that she watch him, citing things such as being right next door, her flexible work schedule, etc...

I was receptive but also hesitant about accepting such an offer. If things didn't work out, I didn't want her to feel obligated or awkward if she decided she couldn't after some time.

The conversation ended shortly after. Upon going our separate ways, Chy once again reminded me that she was looking forward to watching my son. 

In the following weeks, Chy did start babysitting. 

At first, Chy would come over right before I left and leave shortly after I got home as if to keep things professional. Though at this point it didn't need to be. That soon changed when I offered to make dinner and invited her to join. This led to a short conversation about her not wanting to intrude or inconvenience me. In response, I let some of my emotions and my attraction toward her escape. I told her that she was always welcome to be here and how much I really enjoyed her company. Without any hesitation, she quickly agreed and offered to help as well.

In the coming weeks, a really good relationship developed. Chy started staying for more dinners and often let me shower before she mosied home. We often talked for an hour or two every evening. She would ask for advice or vent to me about a girlfriend and occasionally complain about school or work. I learned a lot about Chy. Things really progressed the night we talked about relationships. Chy told me that she never really had a serious relationship and volunteered to tell me she had only had sex once. Details started flowing out when she caught herself and turned bright red, embarrassed that she was saying all of this as if I were one of her girlfriends. It didn't bother me at all, though. It actually caused me to fantasize a bit. I could really make her appreciate a real man with experience. After all, I was six years her senior and had a very sexual past stemming from my early teens. 

I reassured her that she could talk to me about anything and I wouldn't judge her or make it uncomfortable. Maybe I even passively encouraged it. We all have feelings and emotions. I was willing to listen to anything she wanted to talk about.

I reiterated my fondness for her and casually expressed my physical and growing emotional attraction for her. 

We texted back and forth that night as well. She thanked me for showing so much compassion and being so easy to talk to. Chy went on about the way her ex treated her and how I was so much different. It was almost as if she put me in the boyfriend category. We said our goodnights and went to bed. 

Some major changes in my job required me to be on call from 5 a.m.--7 a.m. and continue my regular shifts as well, 7 a.m.--4 p.m. This caused a problem, and Chy recommended I just give her a key to my house so she can just come every morning at 4, even if I didn't have to work. She can sleep in the spare room and will get up as usual to babysit. A week or so later, Chy came to my room to wake me up. It was approaching 7, and she knew that I don't typically oversleep, let alone be late to work. I wake up to Chy's gentle voice from the foot of my bed while she nudges my leg.

"Sorry to come in here, but It's 6:35. You're going to be late.

As Chy walked out, I realized that my cock had been clearly visible, and instead of worrying about being late, I was more concerned about what Chy had to have seen. I was worried that things could be awkward, but either way, I can't change it, so I got up and headed to work without saying much.

A few hours into work, I got a text from Chy,

"Sorry for just coming into your room, I didn't want you to be late. Have a great day!"

I replied, "There's no need to be sorry; if anything, I should be apologizing to you." 

"Why's that?" 

"For you having to see my, uh, you know," shaking my head as I press send. 

45 minutes go by and still no response.... This had me worried. Did I just make it weird? Maybe she didn't see me, and now I seem like a perv.... she had to have seen me naked; there is no way she couldn't have. 

Finally, my phone goes off. It's Chy. "Lol, it wasn't like you intentionally whipped it out. I wasn't trying to look, but it did catch me off guard. For all you know, maybe I liked it."

Now my heart is racing. I'm excited and nervous at the same time. This could go in any direction, so I took a shot in the dark.

"Well, if you liked it, maybe you should have done something about it." 

She messaged right back, "I didn't want to cross a line or do something unwanted. Plus I'm not that experienced in that way. It probably would have been terrible."

"Well, I can tell you that it isn't unwanted. If you only knew.... Im sure you have seen enough porn to have an idea on what to do." 

"If I only knew what?" she asked.

"Just how I feel about you, and some of the thoughts that have run through my mind since we met."

Quickly, she responded, "Well, tell me! I want to know!"

"I would, but... maybe someday I'll show you what my thoughts have been, if I told you now, it would take away from the excitement," I explained.

"Is that so? Well, maybe you'll need to be woken up tomorrow! You still didn't tell me how you felt about me either."

"How about this? If you wake me up tomorrow, maybe I'll tell you how I feel." 

"THAT'S SO UNFAIR!" Chy demanded.

That evening, when I came home, I packed up my son and met his mom for her weeklong vacation with him. I didn't get much time to talk with Chy before I left, and I kind of missed the interaction with her. With my son gone, Chy won't be coming over at 4 a.m. I wondered if she'd come wake me up. My mind is racing, fantasizing about all the possibilities.

Being impatient, I almost texted her. I decided against it as I didn't want to seem pushy. I wanted to know if she was going to come or not, though. I was becoming anxious and impatient. 

This has been a fantasy for a long time. I just never wanted to rush the relationship and ruin it before it started. 

I was so horny; my mind was thinking about what her body would look like naked. How it would feel to touch her soft skin and rub her body... I began to masterbate. Imagining her taking off her clothes... I came in minutes.

I didn't sleep well, and around 4 a.m. I heard my front door open and close. She was coming! My heart was racing from the anticipation of it all. My TV was on, but you could barely hear it. I decided to pretend I was sound asleep with my naked body underneath. About 5 minutes passed, and I started to think that I was overtired and just heard shit because she's not in here yet. My mind is playing tricks on me. Then, I hear soft footsteps coming from down the hallway. Just peeping through the crack of my eye, I see her walk in. There she was, my sexy, petite, horny babysitter, and she was already completely naked, her hair pulled back into a ponytail. I wanted to open my eyes and really take it in, but I wanted to see what she was going to do, thinking I was asleep. I know she doesn't have much background in these situations, but it's going to be enjoyable. Her innocence was such a turn on. 

Unaware that I was awake, she slowly got closer to the bed. She pulled my blanket off just enough to expose my rock hard cock. 

She whispered to herself, "Oh fuck!" 

She wrapped her small hand around my dick while simultaneously grabbing her nipple with the other. Her breathing intensified noticeably.

Stroking my dick ever so lightly, she crawls into bed and straddles my legs, resting her firm ass on my thighs. She leans over, and her soft lips start kissing my neck. Slowly working her way down. Her tongue soon grazes my nipple before her little kisses continue all the way down my abs.

 She gets down to my cock and hesitates. I can feel her warm breath teasing my cock as she decides how to proceed. I feel her lips slide over the tip. Soon she was gagging as half my cock disappeared into her mouth. I chuckled at this and waited for her to continue. She sucks it slowly, deeper and deeper into her throat.

At this point, I'm staring down at her. Her ass is propped up in the air. I slowly reach down and grab her ponytail. Her eyes met mine. 

"You're so fucking sexy." 

"And your cock is so, it's so thick," she mumbled with it still in her mouth.

I can't wait to see the rest of her naked body. I pull her up so her perky c-cups are perched over me. They were proportioned perfectly. Lite pink nipples no bigger than a quarter. I grabbed her tight and flipped her onto her back. 

"You don't know how many times I've cum thinking of this happening," as my cock pulsed.

I ran my hand along the side of her face and leaned in for our lips to meet. It was so passionate. 

I moved to her neck, nibbled her ear, and little moans would escape.

I worked my way down her body, sucking her nipples and admiring the small freckles and her toned body. I got to her inner thighs, where I finally got to see her beautiful pussy. Her labia was perfect. They lay there spread out on either side, begging to be pulled on and sucked. I imagined how they would look gripping my cock as she rode me. This feeling of... so many things, directly impacted the sensuality that followed.

I kissed her inner thighs slowly, not missing an inch. With each movement, my tongue became closer and closer until I dragged it right over her clit, barely touching it. She tensed up and begged me to keep going, but I made her wait in agony, refusing to go all in for a good five minutes. The foreplay was appreciated, judging by how wet she had become in such a short time. A trail of her juices had made its way to her shaved, pink butthole and made a noticable spot on my sheets. I started to suck on her pussy lips and gently rubbing her clit.  I had to eat every last bit of the juices she expelled, so I began thrusting my tongue into her as far as I could. She tasted amazing. As my one hand reached up, teasing her breasts and pinching her nipples, with the other, I inserted one finger, then two, and pushed my luck as I shoved three into her. She pulled away and painfully moaned. I apologized, feeling stupid for even trying. 

"No, keep going, but slow," she insisted, "it hurts so good!"

I worked my fingers back into her tight hole. She began spreading her legs as wide as she could by putting her feet on the sides of my shoulders. I grabbed her sexy little feet and her toes began to curl tight. Chy was about to cum for the first time with a man. Her legs squeezed my head so tight that it was impossible to pull away. After she relaxed, I worked my way back up, staring into her eyes. She looked so satisfied and dazed. I ran my cock back and forth over her pussy. Chy grabbed me and pulled us closer. 

She whispered in my ear, "Please put it in me, I want it so bad."

And so I did. Inch by inch, teasing her until she couldn't take it anymore. She thrust her hips into me and fully inserted my cock into her tight little pussy. We sat for a few moments just staring at each other, bit of us equally enjoying the intimacy.

I took my time going in and out, feeling every inch of her pussy. I began moving faster, her moans got louder. She was saying things that I never thought would come out of her mouth. 

Her pussy began to tighten as she said, "I'm gonna cum again for you, don't stop this pussy is yours, baby."

Within a few moments, I told her I was going to cum that I couldn't hold it much longer. 

She demanded I come inside her.

"Please don't pull out, I wanna know what it feels like to have cum inside me." 

I didn't even hesitate. My cock exploded more than it ever had before. I felt each pump deliver another shot into her until it gushed out and made a mess all over the sheets.

I instantly collapsed onto her chest, then rolled over onto my side, facing her. Shaking from the orgasms, she took her hand and wiped my cum from inside her and fed it into her mouth. 

"Mmmm, I want more," she moaned, "can we do it again?" 

"Soon but for now let's just cuddle."

I got her a towel to clean herself up with. I called off for work for the day knowing I wouldn't wanna be anywhere else.

We sat there and held each other close, her butt cheeks nuzzled tight against my cock. Her boob cupped in my hand and her hand on top of mine. Before long we both were asleep...