Bailey was our very vivacious seventeen-year-old babysitter and from the moment I first laid eyes on her, I knew I wanted to experience a little private one-on-one time with her. Bailey was an elusive catch, but one that was worth pursuing.
Our relationship was very casual at first and very businesslike, but the more she took on babysitting duties for Ally and me, the more desirous I became. I loved Ally, but our marriage had become a little rocky. I was pretty sure Ally was seeing someone on the side, even if she denied it when I confronted her. So, I had no guilty feelings in pursuing our babysitter.
Bailey had a habit of wearing the cutest cut-off shorts that were barely street legal. I don’t know how her parents let her out of the house wearing what she often wore: T-shirts that were always way too small and tight and those damn cut-off shorts with the pockets hanging down, and flip-flops.
Ally didn’t much care for the Bailey look, but didn’t say anything until one day she caught me in a stare-down as I was admiring Bailey’s very cute ass from our kitchen.
“If you want her,” Ally said in disgust, “just don’t be so obvious about it in front of me.”
I played stupid and like I didn’t know what she meant, but Ally was not falling for my stupidity trick. I decided to cool it for a while, just to have some peace in the family. I decided to work on my relationship with Ally while keeping my most secret fantasy in check. We decided to have date nights on a regular basis, in addition to our regular nights out: an evening with me and some of my guy friends playing poker, and Ally with her friends doing whatever girls do when they get together.
One evening, Ally decided to go out with her friends. She wasn’t gone five minutes when Sam, one of my friends called and asked me to come and play a game of poker. It was my night to babysit our kids, but then I thought about Bailey. I punched in Bailey’s number on my cell phone. Bailey was very congenial.
I was shirtless when the doorbell rang. I didn’t think to put on a shirt as I swung the door open and welcomed Bailey into the house. Her eyes widened when she saw me shirtless.
I quickly apologized and explained that I was getting ready to head out to play poker.
“You’ll have to teach me how to play poker one day,” Bailey replied as she stepped past me and into the living room. “I hear it’s fun.”
I casually joked, in response, “Only if it's strip poker.”
Bailey quickly shot back, hand-flipping her very long blonde hair back over her shoulder, “Then, by all means, count me in.”
I was shocked. While flirty and dressing whore-like, I had never known Bailey to be outright mischievous. I dismissed her comment as just a passing comment, and I didn’t take her seriously.
Then a few days later, she texted me and asked: When’s the next poker game?
I had forgotten about her comment and figured she was looking for another opportunity to babysit, since we paid extremely well.
Let me check with the guys, I replied.
I texted Sam and asked when we were planning our next poker game, and he quickly texted back and told me it was a week from that very same day.
I texted Bailey and told her the date and she replied, Can you pick me up?
It was an unusual request since she lived four houses down from us and I figured she could just walk to our house.
Sure, I said, confirming whether seven o'clock was a good time. I had no reason at that point to think anything else about the request. I texted Ally and let her know about the plans, just in case she was going out as well. I told her that Bailey had agreed to babysit for us.
Friday was a hectic day at work. I was more than happy to get out of there. At five, Ally called me and said she was miffed at Bailey. I was totally clueless.
Ally had called Bailey and Bailey had told Ally she was tied up for the evening and couldn’t babysit. She asked if I could skip the poker game and babysit while she went out with the girls.
“You’re always out with those bitches,” I groaned, and then the fight was on.
Ally ended up hanging up on me and for that, I was happy. I hadn’t been out with the guys in weeks and she had spent every other night out with her girlfriends. I needed a night out. I called Bailey and texted her to see what was going on, but she didn’t answer either my text or my phone call.
Ally didn’t say a word to me when I got to the house. She was miffed. I quickly showered and changed clothes. Ally was still miffed. No “Hello,” no “How was your day?” not even a “What time are you coming home?”
“Should I get a hotel room for the night?” I asked.
“Maybe you should,” Ally angrily replied. I hated it when she got this mad. I really did.
“Maybe I will,” I told her. Her anger at me was way misplaced. I left the house without saying another word.
I called Bailey to ask what was going on.
“Are you picking me up?” she asked.
“Yes,” I replied, “but Ally told me you’re not babysitting.”
“I’m not,” Bailey replied matter-of-factly.
I didn’t understand.
“How far away are you?” Bailey asked.
“I’m sitting outside your house right now,” I replied.
“Hold up and I’m on my way out,” Bailey said, and then the call disconnected.
A few seconds later and Bailey darted out of her house and into the passenger side of my truck. Instead of her trademark cut-off shorts and tight t-shirt, she wore a cute, very short mini-skirt and a button-down, untucked white cotton shirt with the top three buttons unfastened and a good deal of her all-natural 36D-cup cleavage showing. Her long blonde hair was pulled back into a ponytail, and she sported bangs, something that gave her a schoolgirl look.