Hailey's Sexcapades: I Got Caught Skinny Dipping

Chapter 1: Hailey's Sexcapades: I Got Caught Skinny Dipping
  • Chapter 1: Hailey's Sexcapades: I Got Caught Skinny Dipping
  • Chapter 2: Cleaning Off By Getting Dirty
  • 1 month ago
  • 82 min read
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“Have either of you ever been with a black guy?” my friend Jasmine asked.

“Well, we all know Hailey hasn’t, but I have,” Courtney said.

I rolled my eyes. “Thanks Courtney.” She was always bagging on me for not being as ‘free spirited’ as her.

“Was he big?” Jasmine asked.

“Yeah. He was like six-two and played football. So, y’know, fit.”

“No, I mean was he big,” Jasmine insisted.

Courtney smiled. “Ohhhh… No he was pretty average.”

“Have you ever been with someone super big?” Jasmine asked.

“No, not really. I’m pretty sure all guys are around the same size and they just pretend to be larger than average to tickle their egos.”

“You know all about tickling egos,” I said, taking a bite of popcorn from the bowl between us. The three of us sat in our PJ’s on the floor of my bedroom. I still lived with my parents to save money during college, and often invited my friends over on weekends so we could help each other with homework, eat non-cafeteria food, and have girl talk.

We jokingly referred to ourselves as Charlie’s Angels because we were attached at the hip and thought we were bad ass. Courtney was a tall, skinny blonde, Jasmine was a petite Filipino, and I was a curvy redhead. We all found each other on orientation day of freshman year of college and had been partners in crime ever since.

“Should we get started on our chem homework?” Jasmine asked. We looked back and forth at each other. No one wanted to. Without speaking, we all agreed that homework would wait.

“Wanna play truth or dare or something?” Courtney asked.

“So you have an excuse to feel my boobs again?” I asked, a playful jab at the last time we did it.

“Not my fault you have nice boobs. I genuinely thought you had them done,” Courtney said.

“An E cup isn’t even an outrageous size,” I said. Both of them looked down at their own, much more modest chests.

“A perky one on a waist like yours is. You’ve got a porn star body and don’t seem to realize it,” Jasmine said.

“Yeah, I would kill for your rack,” Courtney added.

“You would die with my rack. Do you have any idea how much my back hurts every day?”

“You don’t even use them to their full potential!” Courtney said.

“Full potential? What do you mean full potential?” I asked, not offended but sassy.

“You’re still a virgin, right?” she asked me.

“I’ve masturbated and stuff,” I said.

“That doesn’t count.”

“What’s wrong with being a virgin?” Jasmine asked, defending me.

“There’s nothing wrong with it. I’m not saying it’s bad, but with a rack like that you could get a lot of action is all I’m saying.”

“You get a lot of action and you’re what, a B cup?” I said.

“Exactly! I bet you have guys drooling over you all the time and don’t even realize it,” Courtney said.

“Maybe she’s just not interested in guys right now,” Jasmine said, coming to my defense again.

“Fine, whatever. You guys are so prude that truth or dare is never fun anyway,” Courtney said, grabbing a handful of popcorn and tossing it at us. A kernel fell between my cleavage. I dug it out and ate it.

“You’re the one that always wants to play that stupid game. How old are we, thirteen?” Jasmine said, tossing a handful of popcorn back at her.

Courtney blocked the incoming volley with both hands. “It’s supposed to be fun! Boundary pushing, a little risque, but you two never go there. The most fun I ever had was when we got to touch Hailey’s boobs, and that was pretty tame compared to some games I’ve played.”

“What if we just play dare then?” I suggested. The both looked at me in unison.

“There’s no way you guys would be any fun,” Courtney said.

“Let’s just do one round, with reasonable dares. Then when we’re done we knock out our homework,” I said.

“You would chicken out immediately,” Courtney said.

Honestly, I wasn’t super thrilled of the idea because I knew they would cook up something excruciatingly embarrassing for me, but I was also kinda tired of them making fun of me for not being adventurous. I didn’t drink, didn’t smoke, didn’t have sex. I didn’t cheat on my homework, I didn’t use my generous figure to my advantage, and they both reminded me of these things constantly. Courtney more so than Jasmine, but still.

“Fine, I’ll go first,” I said, folding my arms confidently.

“You? You’re gonna take the first dare?” Courtney asked.

I nodded. Both Courtney and Jasmine looked at each other. I kept my arms folded and looked them both in the eye, letting them know I was serious. They leaned in close, whispering for a while. One would suggest and idea, then the other would shake their head and suggest something else. They went back and forth a few times before Jasmine stood up and walked over to my window. She pulled the curtain back and looked outside. She squinted into the darkness, then turned and gave Courtney a thumbs up. What exactly were they planning for me?

“We dare you to skinny dip in your neighbor’s pool,” Courtney said with a smug grin.

I swallowed hard and my heart fluttered. Butterflies flapped in my stomach. I was anxious, but I didn’t want to back down and give them one more reason to make fun of me. “Is he home?” I asked.

“No, we just checked. We knew you’d chicken out if he was home,” Jasmine said. I stood up and looked out the window anyway. His driveway was empty. The lights were off. It certainly looked like he was gone, which wasn’t unusual. I didn’t know him very well, but I gathered that he was a young entrepreneur of some kind because he was gone for days at a time.

“Well?” Courtney asked.

As far as dares went, this one wasn’t so bad. It wasn’t like I’d have to text nudes to someone or do anything else that would leave evidence. I heard that Courtney was dared into a blowjob contest before with some random guys, so this wasn’t nearly as bad as that. I just had to put on my birthday suit and take a dip. It was dark, he was gone, I live in a quiet neighborhood. What could go

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Written by Vivica Snow
Uploaded March 11, 2021
Notes Hailey is an average girl, but somewhat prude. When her friends dare her to skinny dip in her neighbor's pool, she sees and opportunity to explore her wild side.

Her plan goes off the rails when her hunky black neighbor comes home and catches her in his pool naked and vulnerable. Before that night, Hailey
was basically a virgin.

She most certainly isn't now.
AddTo content hare