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Got back from a family vacation to Hawaii a week ago. We took our kids babysitter, Leah with us on the trip. It was my wife’s idea, even though I told her I was a bit concerned her swimsuits may be more revealing than they should be around our two boys. She used to watch the kids a lot before going to college, and she has always been a beautiful young lady.

My wife said she wasn’t worried about it, all the girls today were wearing tiny swimsuits. So we brought her with to have some opportunity to go do things just the two of us.

Was a great trip, and I would be lying if I said I didn’t enjoy watching Leah prance around almost naked all week. She’d become quite the gym girl in college with thick thighs and a shapely round ass to compliment her perky tits and sweet smile. She made me horny as fuck, and became very playful with me as the week went on. Touching me as she would walk by, playing with her hair while we talked, and slapping me playfully when I’d tease her about something.

I directed my arousal to my wife, finding opportunities to release my sexual tension inside of her frequently. She wasn’t sure what had gotten in to me and wasn’t complaining about it either. We even fucked outside while taking a walk which hadn’t happened in forever, like 20 years. As aware of the babysitter as I was, my wife just shrugged off her attentions saying it was cute, unaware of my carnal desires and fantasies of fucking her.

We took a redeye home. My youngest insisted on sitting next to my wife across the aisle and I ended up sitting by the window with Leah next to me in the middle and our other boy on the aisle.

Everyone started to doze off, my mind wondered and I though about what Leah’s pussy was like, remembering it’s soft outline pressing against her tiny bikini bottom. I fantasized about rubbing her through the fabric and how soft it must feel. My dick pressed against my shorts, I’d given myself a boner. Leah was dozing next to me, her head leaning forward and snapping back as she woke herself up with the uncomfortable position.

She opened her eyes briefly, and caught mine watching her. Her lips formed a sweet smile as her eyes shut again. She shifted in the seat and leaned her head against my shoulder. Strands of her long soft brown hair pressed lightly on the skin of my cheek. She smelled like flowers. It was nice.

I fell asleep too. I woke up feeling my cock being pressed against. Leah had slid down and laid her head in my lap, one hand under her cheek and the other resting on my inner thigh, under my shorts, pressed against my balls. I adjusted a blanket to cover her up, knowing if my son woke up he’d have a gorgeous ass, tiny shorts riding up right in his face. Not having anywhere to place my arm, I decided it wouldn’t be inappropriate if I placed it across her body, my hand resting on the elastic band of the tiny cloth shirts she wore.

I closed my eyes and focused on anything but the young woman whose head was in my lap, but I was betrayed by my dick, which became hard as Leah’s head moved gently against it as she adjusted in her sleep. It was in an uncomfortable position so I gently lifted her head while adjusting my hard on, tucking it under the waistband of my shorts, the tip pressing against my belly button.

I prayed she stayed asleep. That prayer wasn’t answered. She stirred, and pressed herself up, her hand gripping my cock firmly. Pausing she turned sleepily towards me, and realized what she was holding on to. Her eyes widened a bit, she sat all the way up releasing her grip, and muttered a quiet apology as she looked down and stared at my dick, throbbing against my shorts.

Pretending nothing happened, and that I didn’t have a monster erection I just leaned back and closed my eyes. I could feel her eyes still watching my cock, my boner the most fascinating thing on the plane at that moment. That certainly wasn’t helping me calm down. Without opening my eyes I adjusted myself again, sliding my dick back inside my shorts and boxers, allowing it to twitch a bounce, and hopefully calm down, which after what seemed an eternity it did. Pre cum leaked from the tip as the flow of blood retreated.

We landed and managed to get back to our house. I thought I was in the clear. Leah needed a ride to go pick up her car that she had left in the shop, and my wife had said she would take her when we were making the plans for the trip.

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7 months ago