Hailey's Sexcapades Ch. 01: Caught Skinny Dipping

"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 ego's," 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 while I was in 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 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 and 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 felt my heart flutter. 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 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 wrong?

"Fine, I'll do it," I said, "Get naked, jump in, jump out?"

"Get naked, jump in, do a lap, then jump out," Jasmine said.

"Fine," I agreed, standing up and grabbing a towel from out of my closet. It was white with pink and red hearts, a Valentine's day beach towel. Why they sold Valentine themed beach towels was a mystery, but I had one and I planned to use it. I shut my closet door, got out of my PJ's and wrapped myself in the towel before going back out into my room. Courtney and Jasmine looked giddy in anticipation and disbelief. Their goody two-shoes prude of a friend was about to go skinny dipping on a dare. "Are you two coming too?" I asked as I made my way to the door.

"Are you kidding? I wouldn't miss this for the world," Courtney said as she stood up.

"Yeah, I kinda think you're gonna chicken out still," Jasmine said.

"You guys better fricken' do whatever dares I come up with," I said, leading the way downstairs and outside. They quickly followed behind me, voicing their disbelief. Luckily my parents weren't home, so I didn't have to worry about any uncomfortable questions. We plodded our way through the kitchen and out onto the back patio. My dog Rufus wagged his tail at us as we walked by, then went back to sleeping on the couch. There was a tall wooden fence along the perimeter of our property, separating it from the neighbors, but one board was loose because Rufus enjoyed sneaking into the neighbor's pool much like I was about to do. We pushed the board to the side and ducked our way through, entering my neighbor's yard amongst some of his tall bushes.

He had a great house. It was basically brand new, heavily remodeled after he bought it from the previous owner. It was large and had lots of windows with a very boxy, geometric feel to it. It was the type of house you see on every modern home catalog. His pool was completely redone too, with an attached hot tub that poured into the actual pool like a waterfall. It was well lit and well tended to. We crept along the fence, using his tall bushes to hide until we were closer to the pool. I turned around and looked at Jasmine and Courtney. They both looked more nervous than I was.

"You ready?" Courtney asked. In response, I unraveled my towel and handed it to her. The air was cool on my naked body, exhilaratingly so. Both of my friends covered their mouths in surprise and did their best to stay quiet. They were shocked I was about to go through with it.

"If you two don't do my dares, I'll kill you both," I said with a stern finger. Then they watched in awe as I stepped out from the cover of the bushes and made my way over to the pool. I jogged to move faster and was reminded of my exceptional bust as my breasts bounced, unsupported by any bra. I reached up and grabbed them, one in each hand, to steady the bouncing. A motion sensing light switched on as I crossed the yard and put my feet at the edge of the pool. I looked over, startled that the light came on, but realized I wasn't in any danger of being caught. I looked down the length of the pool and thought the fastest, most discrete way to swim the length of it and get back was to dive and spend as much time underwater as I could. I let go of my breasts, put my hands together and did the best dive I could to minimize splash.

Just as I was about to hit the water I thought I heard my name but it was too late. My dive was clean, and I felt like it made barely any noise, which I was proud of. Thankfully, the water was warm, heavenly in fact. I held my breath and kicked with my legs, using my arms to help propel myself to the other side of the pool while staying under water so I could stay as hidden as possible for as long as possible. It was surprising how good it felt. Obviously I'd swam in pools before, but never naked. Feeling the water flow passed my body with no fabric felt different somehow, in a way I can't describe. Maybe it was just the satisfaction of going through with the dare or the excitement of doing something naughty for once in my life.

My hands touched the opposite side of the pool. I was almost out of air but I turned around underwater anyway and pushed myself off the wall with my legs. I got a few more strokes in before I came up to the surface. Smiling big, triumphant, I surfaced and took in some air. My hair clumped over my face so I used both hands to collect it and push it behind my ears before clearing the water from my eyes. I looked over at the bushes, expecting to see Courtney and Jasmine shaking their heads in disbelief at me.

They were gone.

I looked around and noticed a light was on in the house. Through the big windows I saw my neighbor putting down his keys on the kitchen table as he unbuttoned his shirt. "Oh, shit!" I whispered, quickly swimming to the edge of the pool closest to the house so I could hopefully hide behind the raised hot tub area. As I reached the edge of the hot tub, I saw my neighbor glance out toward me. I ducked my head under the little waterfall created by the hot tub and lowered myself so that just the top of my head and to my nose was sticking out of the water. A moment later I heard one of his massive sliding glass doors open.

"Hello?" he said. I looked around, trying to think of an escape plan. "Is anybody out here?"

A series of ripples displacing the water from when I dove no doubt looked suspicious. I glanced over to where I had dove into the pool and saw that though my dive was pretty good, I splashed water onto the pool deck that he easily could have seen.

"Rufus, did you sneak in again?" he asked in good humor. I heard his dress shoes clicking on the concrete toward me. If he walked over and looked in the pool he would no doubt see me naked and I'd have a bunch of questions to answer. I had to think fast.

"It's just me Mr. Chapman," I said, poking my head above the edge of the pool and sticking my arms out so that my elbows rested on the pool deck. I pressed the rest of my body against the wall of the pool, keeping it hidden from view even if he were to come closer. My plan was to try and convince him to leave so I could sneak out before he knew I was naked and then never speak of this again. He stopped maybe fifteen feet away. His eyes bulged in surprise as he saw me. "You're that girl next door. Hailey, right?" he asked.

"That's me!" I said, trying to act as normal as possible. I looked him up and down. He was tall, over six feet, and very dark-skinned. He had a tight fade, and a well-kept goatee. His dress shirt was unbuttoned and showed the white tee shirt underneath, the fabric of which was strained around his torso. That was because of his brawny chest and shoulders from lifting weights regularly, a habit I knew he had because I watched him do it from my window occasionally. Like many black men, he had features chiseled from marble. High cheek bones, a strong jaw and piercing blue eyes that made him look like a darker-skinned version of the guy on Almost Human.

"Uhh, what are you doing here?" he asked.

"Just taking a dip," I said, still trying to sound normal.

"Are you aware that's trespassing?" he said. He didn't sound upset, but rather confused.

"I, uh... wanted to see what Rufus was so crazy about. Your pool is lovely," I said.

"Thanks, but I kinda want to go to bed. I had a long day. Let me help you out so you can go home," he said, taking a few steps toward me.

"No!" I said, pushing my hands out to make him stop, "I, uh... I can let myself out, why don't you go to bed?" I said.

He continued forward. "It's no trouble, I'm just tired." He held out his hand to help me out of the pool and stepped up to the edge, looking down at me. "Oh my," he said as he stared down at my pale, naked body in the water. All he could see was my back and probably my booty, but he certainly could tell I had no suit on. "Ah shit," he laughed, covering his face in embarrassment and turning away from me.

"Sorry," I said, turning bright red. I didn't know what else to say.

"Why are you naked in my pool?" he asked, his back facing me.

"I sorta did it on a dare because I didn't think you were home," I admitted. I was deeply embarrassed, but he was being polite about the situation, which somehow helped.

"I just got home," he said, still shaking his head.

"Yup. I see that," I replied.

We both started laughing.

"Well, this is a first for me," he said.

"Me too!" I laughed.

He took off his blue button-up shirt and tossed it to the edge of the pool, averting his eyes. "Put that on and let's get you inside," he said.

I looked at his shirt, which would easily be big enough to cover all the important parts, but it would be soaking wet after.

"If you wanna run inside and get me a towel that's fine, I can wait," I said.

"Nah, don't worry about the shirt, just cover yourself up," he said. I looked back toward the bushes to see if my friends were there. They weren't. I moved over a few feet so that the water running off my body when I got out wouldn't immediately soak his shirt, then climbed out of the pool. He still had his back to me, so I took the opportunity to try and wipe some of the water off with my hands and wring out my hair before I bent over and picked up his shirt. I slipped my arm into one side and wrapped it around my body to slip my other arm in, then looked forward.

"You all good?" he asked.

"Yeah, thanks. Listen, I don't want to take up any more of your time, I can just leave and return your shirt in the morning," I said.

"Nah, don't be silly. Let me make you a cup of coffee or something," he said.

"I couldn't."

"I insist. If you and Rufus are gonna be using my pool, I should at least get to know you a bit."

I was surprised at how cool he was being about all of this. It was a ridiculous situation, to be sure. Maybe he was extremely amused by the whole ordeal. Maybe he liked the fact that I was so vulnerable. I had never really talked to him before, just watched him work out and admired his body like a creeper. Getting to know him, even under such strange circumstances, might be fun.

"All right, if you insist," I said, following him inside. As we walked toward his house I realized that the large glass doors reflected the pool area with astounding clarity. I wondered if he had gotten an eyeful while I was wiping water off myself. If he had, oh well, there was nothing I could do about it now. The inside of his house was as beautiful as the outside. Because of the large glass windows I had a good idea of which his kitchen looked like since I could see some of it from my bedroom window, but his living room was just as large and opulent. He had a large black leather couch and a glass coffee table. Interesting cityscape photography adorned his walls, lit up by a crystal chandelier above the foyer area and recessed lighting along the ceiling. Music played from hidden speakers and a giant TV dominated one wall. Total bachelor pad.

I stood in the kitchen, drip drying and soaking his blue shirt as he pulled one of those single serve coffee containers out of a drawer and put it into his Keurig machine. "How do you take it?" he asked.

"Black," I said. He paused for a moment, then continued making my coffee.

"What about you?" I asked, more to make conversation than anything.

"Extra cream, extra sugar," he said, "You can go sit down if you want."

I considered protesting. I didn't want to get his nice furniture wet, but he obviously didn't care. I walked into his living room and sat down on the big leather couch. It squeaked as I got comfy. By now water had soaked through his shirt pretty thoroughly and it clung to my curvy frame. While standing his shirt was long enough to cover passed my booty, but as I sat down, it didn't quite make it. Sitting down and crossing my legs covered my bits, but my bare, milky thighs were exposed. I'd make due.

"Bit of a thrill seeker, huh?" he asked from the kitchen.

"I'm really not. This is very out of character for me."

He came out into the living room a few minutes later with two mugs of coffee. He handed me mine, and I took it, blowing on the top to cool it off. He sat in a black leather lazy boy across from me.

"So do you skinny dip at night because otherwise you'll burn?" he asked, a coy smirk on his face.

As a natural redhead my skin was beyond fair. I was white as snow except for the few freckles dusting my cheeks and shoulders. I let out a snort as he said it. "I swear I've never skinny dipped before, tonight was a fluke and has obviously gone horribly wrong," I said.

"How come?" he asked.

"Because my neighbor caught me naked in his pool?" I said with an awkward chuckle, taking a sip of my coffee. It was the darkest, richest coffee I'd ever tasted. Delectable.

"No, I mean how come you've never been skinny dipping before?"

He was looking me in the eyes, as if nothing were out of the ordinary. I looked away, still embarrassed by the situation. "I dunno, I've just never been that adventurous. My friends always make fun of me and I kinda just wanted to shut them up, so I decided I'd try it. The fear of getting caught is the exact reason I never do stuff like this, and now look where I am. Why, how many times have you been skinny dipping?" I asked, trying to put him in the hot seat a little.

"Plenty of times," he said, sitting back in his chair.

"Plenty of times? Really?" I asked.

"Yeah. Where I grew up we had a lake. A bunch of us would go out there in the middle of the night sometimes. I loved it," he said.

"How come you don't skinny dip any more?" I asked, sipping my coffee.

"How do you know I don't?" he said with a smirk. For some reason that flustered me. My heart was thumping fast, and those butterflies were back. How could he be so cool and collected in a situation like this? Maybe because he wasn't mostly naked. "Do you mind if I change into my PJs? I'm sick of this suit," he said, putting his coffee on the glass table between us and getting up from his chair.