Bailey Our Baby Sitter and a Friend
- 3 years ago
- 16
- 0
Bailey, Our Babysitter free porn video
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.
“I’m ready,” Bailey declared as she put on her seatbelt.
“For what?” I asked. I was totally confused.
“To learn to play poker,” Bailey declared.
I don’t know how long I sat there in stunned silence, trying to process her words.
“Uhmmm, “I stuttered, “This- this- this is just me and some of my friends.”
Bailey looked surprised and disappointed at the same time.
I reached across the bench seat of my truck and patted her bare thigh with my right hand.
“I’ll teach you to play poker, one-on-one,” I replied, hoping that she would understand.
Bailey stared straight ahead, processing my words.
“Well fuck,” Bailey declared. It was the first time I had ever heard her curse.
“Fuck, fuck, fuck,” she added. It was an awkward moment for both of us.
“Well,” I replied, “If it makes any difference, you look pretty hot in that outfit.”
Bailey chuckled and then brought her hand up to her mouth. I could see her thinking. She dropped her hands to her lap and looked out the passenger side window and back at her house.
“Do you have time for us to go for a short drive?” she asked, still looking out the passenger-side window. I looked at the clock on the dash and it read 7:05. The poker game wasn’t due to start until 8 pm and the drive to Sam’s place only took about three minutes.
I placed my truck in gear, and as we drove away from Bailey’s parents' house, I asked where she wanted to go.
“Anywhere,” she declared. “Just drive.”
I steered out onto one of the neighborhood streets and punched on the radio. Bailey slipped out of her flats and stuck her bare feet up on the dashboard in front of her, her mini-skirt bunching up in her lap and giving me an unintended view of a lot of leg.
I had only driven about a block when Bailey asked, “Would you like to fuck me?”
I damn near drove off the road.
I looked over at her in silence to make sure I had heard what I thought I had heard.
“I’m serious,” Bailey declared.
“I’m married,” I replied.
“I didn’t ask you to marry me, just to fuck me,” Bailey shot back.
Whoa. Full stop. I pulled into the parking lot of a Taco Bell and parked.
I turned and looked at Bailey.
“What makes you think,” I began slowly, “that I’d want to have sex with you?”
“I can tell,” Bailey replied. “You’re always looking at me.”
As she spoke, she shifted in the seat, arching her back and then buttocks from off the seat, slipping the edge of her miniskirt out from under her very cute ass that she promptly replanted on the bench seat.
I took in a deep breath and forcefully exhaled.
“You are hot as fuck,” I said. “You deserve more time than I could possibly donate to you.”
“I’ve got the time,” Bailey replied. “My parents think I am spending the night with a friend.”
I was trying to figure out a way out of the hole, but another part of me was also trying to rationalize fucking the shit out of her.
I looked across the street at a Holiday Inn. Oh, how fortuitous.
I silently placed the truck into gear and steered across the divided roadway and into the parking lot of the hotel. Bailey didn’t say a word.
“Wait here,” I instructed, as I exited my truck and sauntered into the hotel lobby.
The clerk was a middle-aged woman and she asked if she could help me.
“One room, king-size,” I said, surrendering my driver’s license and a credit card for her to use and register me. I signed the guest registration form, and she handed me back a card key access, my license and my credit card.
“Enjoy your stay,” she politely proffered. I assured her I would.
I stepped back out to my truck and asked Bailey if she was sure about going in. She smiled and slipped her black lace panties onto my rearview mirror.
Holy cow!
As soon as the room door closed and clicked, Bailey attacked me with a ferociousness and fury, unlike anything I had ever experienced before, thrusting her hands onto the front of my pants, groping me as she pushed me up against the back of the room door.
I had her shirt completely unbuttoned in very short order, as she fumbled with the belt to my pants. Oh my God! She had the body of a porn star nymphet and was every bit what I had hoped for and expected and then some.
We then spent the next hour and a half pleasuring each other. My phone buzzed and buzzed and buzzed. I simply ignored it.
Finally, after doing the deed and expending all my energies, I reached over and grabbed my phone as Bailey lay naked and spent next to me.
There were fifteen “Where are you?” messages from my friends. I typed out a quick text message apologizing and saying that I had found a cute teenage nymphet to fuck and wouldn’t be able to make the poker game. I got several laughing emojis in response. Is there nothing worse than being truthful and then being laughed at by friends? Sheesh.
And no, I didn’t go home that night. Ally was fine with my decision, to my great surprise and relief. We eventually worked things out and everything was great.
Bailey and I hooked up several more times, until she had to leave for college, which I hated. We managed to stay in contact, but over time, she stopped texting and I knew at that point, a good thing had come to an end.
It was super depressing.
Then just a week before the Christmas break, Bailey sent me a text, apologizing for not staying in contact. She had made straight A’s and was looking forward to being home for the holidays. She appended the text message with a photo of herself with another stunner of a friend, named Rachel, and then she texted not-so-indiscreetly: Rachel is a Holiday Inn lover.
Damn.
Louise
- 14.07.2020
- 10
- 0
- Category:
- Cheating
