New Babysitter [F19/M35]

Sharon was away two months for work, and I was left to deal with our toddler. Since I was also working full time, we frequently relied on babysitters. At this point, we had a decent rolodex of nannies to call, and this weekend I was getting some long-overdue time with the boys. Friday through Sunday we'd be hitting bars, going to the beach, working out, and eating. It was about the only thing I was looking forward to while my wife was away.

I had booked Celine, a lovely, heavy-set middle-aged woman to live here all weekend with Caleb, our toddler. She was kind, nurturing, commanded respect, and could cook like a champ. Her bill was well worth it.

The week leading up to Boys Weekend was dragging. I couldn't stop thinking about Friday afternoon when I'd be free to party. I was also thinking about how much I missed Sharon. She'd been gone a little over a month and I was lonely. We made a great team raising Caleb, and I discovered how much I had taken physical contact for granted. Going a few days without ever being hugged someone is...strange. I missed it. Thank god for Caleb. We shared a lot of quality time when I got home from work and he made missing Sharon a little easier.

Thursday finally rolled around and my cellphone rang during lunch. It was Celine.

"Hi, Celine, what's up?"

"Hello, Bill. I have some bad news. I've got a family emergency and I need to leave town for a week. I'm so sorry to have to cancel on you last minute."

I paused for a moment to take this in. First, I felt frustration, but I knew I needed to respond without a hint of it.

"Celine, it's ok. Please go take care of your family and don't give it another thought. I'll find someone else. Family is more important."

"Bill, you're a good man. Listen, I made some calls this morning to try and find a replacement this weekend and I have someone--if you want the referral."

"That would save me a lot of trouble, actually. Who is it?"

"It's my niece, Sasha. She's young but very responsible. She can stay the whole weekend, just like I was going to, and I taught her to cook, so you can only imagine how well-fed Caleb will be."

"But if she's family, wont you need her to stay with you this weekend?"

"Different side of the family. So she's ok."

"Oh. Well, ok. That would be great. Just text me her contact info. I hope everything with your family resolves well."

And with that, plans had begun to shift. Celine, always the professional, had set me up in spite of her situation and my anxiety was lifting slightly.

I asked Sasha to come to the house at 5pm on Friday so I could show her around the house, introduce her to Caleb, and get a read on her character.

Sure enough, I heard a car pull up a few minutes before 5pm and when I opened the door a minute later, a young woman was walking up to the front door.

She was about 5'4", with wavy brown hair, blue eyes, and an athletic build. She was stunning actually. I usually don't lose my composure around anyone but I felt a slight need to have her think I was cool. It was a very uncool feeling, but it amused me to feel that way.

"Are you Sasha?"

She never broke eye contact with me.

"Yeah, hi. Bill, right?"

"Yes. Come on in. I'll show you around and you can meet Caleb."

She stepped in and looked around, considering. I showed her around the house before showing her to her bedroom, which was on the left up the stairs.

"It's not huge, but we've got a queen in here, so hopefully it's comfortable."

"It's great, thank you. I like your house."

This was the first time she expressed any approval.

"You can thank my wife for that. She's the decorator. Oh, before I forget, you have your own bathroom through this door here," I said, indicating a door to the right once you enter the bedroom. "The only thing is, the shower is broken. Toilet and sink work fine, but if you want to shower or anything you'll have to use the master. I'll be gone until pretty late every evening so it's yours all day!"

"That's fine, thanks."

"My wife buys loads of bath bombs and never uses them so you're free to take a couple if you want. If you forgot a toothbrush or anything, we've got extra. Just let me know what you need.

"Thanks, Bill."

I was a little nervous making sure everything was set for Sasha but she seemed totally unfazed. At first that made me even more nervous, but I just realized she was smart, confident, and cool-headed, so I didn't need to worry. She carried herself with maturity. It put me at ease.

I introduced her to Caleb next and her demeanor changed. She started smiling a lot more and her voice pitched up a bit. She got down on his level to introduce herself. Caleb seemed uninterested at first, but after a few minutes of engagement, he got the idea. Phew.

"Ok, do you need anything else before I head out?" I asked.

"Nope, you go have fun."

"What a relief. Ok, my Uber is here. I'll be back pretty late so don't get freaked out if you hear the door open. You have my cell if you need anything. Don't hesitate to call!"

"I don't think I'll need to, but ok. Thanks."

She was good to go.

I hugged Caleb goodbye and left for a night of bar hopping.

It was around 1am when I caught an Uber back to the house, not wasted, but drunk. I had an amazing night and was so relieved I had another two days to look forward to. I opened the door slowly and tried to be as quiet as I could, but my feet were a little heavy and a little clumsy. It was quiet. The lights were out on the first floor and it seemed Sasha and Caleb were fast asleep.

I took my shoes off and crept upstairs after grabbing a tall glass of water from the kitchen. I was parched. A lot of beer, sweat, and laughter had dried me out.

Up I went and on the left I could see that Sasha's room light was still on. "Ok, glad she's comfortable." I thought to myself, and continued to my room. When I got to Caleb's door, I opened it very slowly and in the soft glow of the moonlight, I could see him fast asleep. Perfect.

I closed the door slowly, let out a long sigh of relief, and finally went to my room. I opened the door and the darkness felt so good on my eyes. I pulled off my shirt and pants, sloppily throwing them on the floor to leave for sober Bill to deal with, and flopped onto the king size bed. The sheets were cool, soft, and clean. I took a big inhale and smelled the detergent, glad I had washed the sheets last night.

I was trying to sleep when a nagging voice in the back of my head said I should pee and brush my teeth first. I ignored it for a few minutes, but I wasn't going to be able to sleep without these evening rituals, no matter how tired I was. So I slowly lifted myself off the mattress to shuffle to the bathroom. I adjusted the wedgie in my boxer briefs and felt myself start to get hard. Damn I missed my wife. Maybe it would go away before it became too distracting to sleep.

I got to the door and noticed for the first time that the bathroom light was on. I left it on all the time and it drove Sharon crazy. It was a bad habit, I'll admit. I opened the door and made my way to the sink. I turned on the cold tap and splashed my face with water, wiping a layer of sweat and bar smog off my skin. I grabbed my toothbrush and paste and brushed as with as much energy as I could muster. While I brushed, my left hand made it down to my erection which was straining a bit now, especially since I had to pee. It felt good to apply some pressure to it.

I looked at myself in the mirror, a little older than last time I really looked: hair still brown, but speckled with gray, some more wrinkles on the forehead, around the mouth, the eyes. Did I mind? Not too much, but it was surprising to see. I was a dad now. That man is a dad. I spit out my toothpaste and looked up again when I heard a noise behind me. My head bolted up thinking Caleb had made his way into the bathroom, but the door was still closed. I scanned the bathroom through the reflection in the mirror and saw nothing. It was just the house creaking. We had renovated an older victorian house, but some of the original foundation was kept for charm...and it creaked.

I was fully hard at this point and thought it might be easier to sleep if I came as quickly as I could. My mind went to the young woman down the hallway and how naughty it was to be touching myself with a guest like her in the house. It made me even harder.

I pulled my cock out from the fly of my boxer briefs and slowly jerked myself in the mirror. I wanted to blow my load all over the sink for some reason. It felt ever so slightly public to do. I thought of how sexy Sasha was and how cool she was. If I were her age, I'd have been intimidated by her, wanting her terribly. From the few minutes we spent together, I thought of what her body might look like: what she looked like under her biker shorts and bra. It was driving me crazy. I was in it now, trying to edge myself slightly before letting myself go. I was entering middle age, but working out 5 times a week kept me looking pretty good. And the freedom to play with myself so unabashedly was turning me on even more.

I felt myself approaching the end, my posture more hunched, pelvis thrust forward with my cock out and rock hard. Just as I was about there, something in the mirror caught my eye and I saw in the bathtub behind me that I was being watched.

"Fuck." I said as I tried to get my dick away and somehow somehow act like I wasn't just about to cum. But my cock had already opened up and I felt a wet spot growing as a ruined orgasm filled my boxer briefs.

"Jesus, who's there?" I said, out of breath and mortified.

"I'm so so so sorry. I fell asleep in the tub and woke up when I heard you come in the bedroom. I was hoping you'd go right to sleep so I didn't say anything. And the longer I stayed silent, the more awkward it would have been to say anything."

It was Sasha. I was beet red, completely unsure of what to say. I was facing away from her with wet, sticky underwear and a still-hard cock that wanted a real orgasm.

"I'm so sorry you had to..." I didn't want to say out loud what we both already knew.

"It's ok. It's my fault. I didn't mean to ruin it." She replied

"You didn't ruin anything. I should have been more perceptive. I'm a little tipsy. Let me get out of here so you can get out."

"Wait, Bill. I--I need a towel. I left mine in my room by accident."

"I"ll get it for you." I said, before bolting for the door to grab her towel from her room.

I entered my bedroom and felt the cooler, dryer air. "Holy shit." I said to myself. "That was bad. If Sharon finds out about that...there's just no way anyone would believe it went down how it actually went down."

I went into her room and saw the towel neatly folded on the bed where I had put it. I grabbed it and tiptoed back to the master bath. I opened the door.

"Here you go." I said, bringing it over to Sasha in the bath, trying not to look. But my impulses got the better of me and I saw a little bit of her: her naked shoulders and collarbones, a chest of small handfuls with hard nippled from the wet and the cold, her skin so smooth. I was still half-hard, the mess visible in my boxer briefs.

"Thank you. Again, I'm so sorry." She said.

"It's ok. I really need to pee though, if you wouldn't mind, and I turned away so she could get out of the tub."

"I'm really sorry I ruined your umm...I'm sorry for watching."

Now I was getting fully hard again.

"It's ok."

"No, I feel bad. You should try again. I wont tell anyone."

"What do you mean?" I couldn't believe my ears and my heart started racing.

"I want to watch you...finish. If you do it, I wont tell anyone."

She wanted to watch me cum? I turned around towards her, my cock fully straining now, and looked at her.

She had the towel loosely wrapped around her and she was watching me intently.

"You sure?" I asked.

"Please."

And with slight hesitation I reached into my fly and pulled out my hard shaft and began pumping.

She stared at it, a little slack-jawed with drool starting to pool in her mouth. The look was intoxicating and I took a step closer to her, so she could get a better look and I could be closer to her.

Without taking her eyes off me, her right hand crept up the towel around her and found her pussy and she began fingering herself. I wanted so badly to see what was happening underneath and I took another step closer, the tip of my cock beginning to glisten.

Sasha bit her lip as a quiet moan came out her voice dropping into a deeper alto. I took one more step until I was close enough to touch her. Our height difference had my cock closer to the bottom of her tits as I brought one hand to her towel and slowly encouraged it to the floor. It fell down her chest first, her free hand keeping it just above her nipples at first, but as I pulled down a little bit more, she let it drop, her beautiful body free. She was fingering herself vigorously moving her index and middle finger in and out of her pussy before playing with her clit, my cock pumping only a foot away. Her pussy was beautiful with a small landing strip of hair neatly running up.

We drank up the sight of each other, our vocalizations growing slightly louder. I was rubbing precum over the tip of my cock and she watched as it became shiny, wet, and sticky. I could tell she wanted to reach out and grab it, but that wasn't the game. She just got to watch me finish.

"I'm gonna cum when you cum." She said to me through frantic breath.

Her anticipating me blowing my load all over her beautiful body was enough to bring me to the edge.

"You're gonna make me cum, Sasha."

"Please, please cum." She begged. She needed to cum so badly and needed me to do that.

Though I didn't want this to end, the temptation of the finish was too strong and I felt the dam breaking. I let out a loud grunt before my cock started spurting its initial juice all over her belly, hand and pussy and Sasha started buckling at the knee as her orgasm was beginning. After the first breach, my cock started shooting jets at her belly and up to her tits before dripping down to her hands and fingers which were working in and out of her pussy. I could see my cum disappear from her fingers up her pussy as she came which made me keep cumming harder. I wanted so badly to fuck her brains out, but knew this was the limit. Sasha almost fell over but caught herself on the rim of the tub as she came down, one hand still lightly massaging her clit.

We stood there, panting ever so slightly, before I went to the sink and turned on the warm water. I grabbed a washcloth and ran it under the water to bring to Sasha. I handed it to her.

"Thanks." She said. "Like I said, I wont tell anyone."

"I wont either."

The magnitude of this moment was hitting as my mind and body sobered up a bit. It started as an accident, but this had gone too far. I knew this intellectually, but my body had no regrets.

Sasha quietly grabbed her towel, wrapped it around herself and made for the door. I almost stopped her to say something, but realized I had nothing to say. The door closed.

I went over to the tub to drain the water when it finally hit me that I hadn't peed yet. I made my way over to the toilet to relieve myself, my cock red and sensitive after an orgasm and a half. Now I was really tired.

I finished up, washed my hands quickly, and headed to bed, turning the light off on my way out. Part of me hoped to find Sasha in the bed waiting for me, but she was gone. I flopped on the bed once again just before I fell asleep, I could feel my cock twitch again and I knew I wanted more.