Hailey's Sexcapades Ch. 01: Caught Skinny Dipping

"It's your house, get comfy," I said.

I watched as he walked away and I'm not ashamed to admit I stared at his butt until it was out of sight. The way the fabric of his slacks tugged around it was mesmerizing. Not because his slacks were too small, but because his butt was so muscular. Get a hold of yourself! I thought. He caught you trespassing in his backyard and you just told him you're not very adventurous, he's not going to be interested in you. He's probably dating two or three different super models right now, he doesn't want a petite, curvy white girl like you. Besides, you have basically no experience. You would only embarrass yourself. I heard his footsteps come down the stairs a few minutes later.

"I've seen you watching me work out you know," he said. My heartbeat quickened again.

"I mean, I've seen you out there from time to time but I don't watch you," I said.

"It's OK, I don't mind. I'm flattered actually, I'm not calling you out. If you ever wanna work out sometime you just have to ask," he said. For some reason, thinking of his brawny body working out, lifting those weights out in the sun, I considered some other workouts we might have together. Then when he rounded the corner of the couch, I had another mini heart attack. He was naked except for a pair of tight gray boxer briefs that outlined what looked like three pairs of socks smooshed down his thigh.

"I'll keep that in mind," I said, sipping my coffee again to keep myself busy, trying not to look at his crotch.

"What's the matter?" he asked, sensing my tension.

"Nothing."

"C'mon, tell me," he insisted.

"Nothing, I'm just surprised how... comfy you are," I said. He laughed.

"I hate wearing pants, so this is usually what I wear around the house. I figured given the circumstances it might make you more comfortable if we were, y'know, even," he said.

"And stuffing your briefs was supposed to make me laugh? Be an ice breaker?" I asked. I must have looked like a strawberry to him with my red hair and my blushing cheeks.

"What do you mean?" he asked, taking his coffee from the table between us.

"Don't play coy, it's not like you didn't want me to notice," I said, still averting my eyes. He looked down between his legs and let out a loud belly laugh.

"No, that's just me. I forget about it sometimes, sorry," he said.

I rolled my eyes. "Don't think I'm that naïve."

"I assure you, I don't."

I looked him straight in the eyes. "You're trying to tell me that that is 100% natural?" I asked, pointing to the anaconda hiding under his boxer briefs.

"Sure am," he said. I still wasn't buying it.

"You must have girls lined up around the block waiting for it then."

"Nope. A lot want to see it when they find out, but few will let it go anywhere near them. Too intimidated," he said, sipping his coffee. I kept looking him in the eye, trying to find a crack in his armor.

"So someone finds out, they want to see it, you show it to them and then what? They tell you to put it away?" I asked.

"Pretty much," he said.

"And you're totally fine with it?"

"Hell no, I've been left blue so many times. It's more of a curse than a blessing."

I let out a little laugh at the thought of an Adonis like him being left with blue balls. "So you just let them go?" I asked.

"Well, I'm not gonna force anyone. And if I don't show it off to any woman brave enough to see it, there's no chance I'll have it tended to, so... I take my chances and hope it all works out."

I thought about this for a moment, still staring him in the eyes to try to make him break. Were women really intimidated by his size, or was this a line he fed to make them want it more? I had to admit it intimidated me. My experience with dicks was pretty limited, but that was easily the largest I had ever seen. If it was even real. He seemed to be shooting straight though, and his honesty was only making more curious. Curious to see if he was bluffing, and curious if I could handle such a monster. I took a deep breath and another sip of coffee. There wasn't much left in the mug, so I downed the rest of it like a shot. Then I put the mug down on the table between us and looked him in the eyes again, gathering up my courage.

"Can I see it?" I asked feeling both brave and foolish at the same time. He smiled.

"Are you sure?" he asked.

I nodded.

He paused for a moment, as if giving me a chance to back out. Then he used one hand to lift the band of his boxer briefs and the other to manhandle himself out into fresh air, where he rested the whole kit and caboodle over his waistband for me to see. I let out a breath and covered my mouth in surprise. It was real. 100% black Angus, USDA choice. My eyes widened, and I stared at it for what felt like a long time.

"Told you," he said after a while. My eyes traced over the thick veins from base to tip. I looked at his large balls pushed to either side of his shaft and acting like a pillow for his shaft. I felt my face and chest flush with warmth and thought I probably looked mortified and embarrassed, because I was, but also desperately curious.

"Wanna touch it?" he asked. He seemed much more calm than I was. He was probably used to reactions like this, maybe even amused by it. I'm sure it added to his confidence. Or maybe his confidence was his way of making his dick less scary to potential suitors. I had never seen anything like it before. I had given precisely two hand jobs in my life and one failed blowjob. Failed because his brother walked in, not because I was bad at it. My nerves always got the best of me in situations like this and I often became so self conscious it was hard for me to enjoy things. Looking at his monster of a cock I wondered what it was capable of, if that was its full size or if it could somehow grow larger. As far as I knew, a man like this was extremely rare and kind of a freak of nature. I probably wouldn't have an opportunity like this again.

"Yes," I nodded.

He stood up and walked over to me, his heavy cock swinging like a pendulum over his waistband. He stopped a little less than an arm's length away from me and waited. He was so tall that his hips were almost perfectly at my head level when I sat up. I looked at his cock in greater detail now that it was up close. It had fabric creases on it like when you've been sitting on a seam in your pants for too long. I thought how uncomfortable it must be for him to have to contain that thing in dress slacks every day. Then I thought about how uncomfortable it must have been for any woman he'd been with to try to take his length. And girth.

I looked up into his eyes from my seated position, as if asking for permission once more. He nodded down at me. I looked down to his cock again and lifted my hand to touch it. First, I cradled his large, heavy balls. They were each about the size of a kiwi and my milky white hands contrasted sharply against them. I squeezed them a little, pulling softly to and lifting to get a sense of their weight. They were heavy. While holding his balls the tip of his penis could almost rest in the crook of my elbow, meaning even soft he was about the length of my forearm. His shaft was about the width of my wrist. I prayed for all his prior girlfriends that he was a shower instead of a grower. Even then he was insanely hung.

"What do you think?" he asked as my other hand lifted his cock from the tip, watching his shaft dip down from the weight.

"I think you've got quite the dick here, Mr. Chapman," I said, still holding it and examining the monstrous thing curiously, like it were some detailed relic in a museum. This time he paused, as if weighing something in his head. I realized he was gathering courage much like I had recently. I gently pulled his tip toward me, measuring its true length.

"Think you could handle it, miss Hailey?" he asked.

I looked up at him, his dick in both my hands. The short answer was no. I didn't have a cherry to pop, but I was still basically a virgin. A cock like his would leave me walking funny for days. I didn't know the first thing about pleasuring a man apart from what I'd seen in porn, and I was smart enough to know not everything you see in porn works or is fun in real life. To have a cock like this as my first time was like vagina suicide. Then I thought about how much Jasmine and Courtney would make fun of me if I chickened out on an opportunity like this. I thought about all the women he'd met over the years who got one look at the thing I held in my hands and went running for the hills, leaving poor Mr. Chapman with a hell of an arm workout to end the night satisfied. They say when life gives you lemons you make lemonade. Well life had given me vanilla ice cream and chocolate sauce and I was going to make the best damn chocolate shake the world had ever seen.

"Only one way to find out," I said.

He grinned and took another half step toward me so I wouldn't have to reach out to touch him. I suspected when he became fully hard he would have crossed the distance without having to step forward. When I released his tip from my other hand it fell and thumped against my forearm with an audible smack. Impressive. I started by gently massaging his balls with both hands. I explored his swollen sack and felt the thin tubes that piped his sperm. Because everything about him was so large it was easy to feel the otherwise overlooked parts of a man's body and for some reason I wanted to explore every inch. I cupped his heavy balls in both hands, squeezing and gently lifting and pulling them, playing with them a little as I gained confidence.

He ran his hand through my bright red hair, sliding his fingers down my cheek and caressing my lower lip with his thumb. I instinctually opened my mouth and reached out with my tongue to feel the pad of his thumb. It just felt right. He gently pushed his thumb up my tongue and let me close my lips around it to suck gingerly. I saw his cock twitch when I did. My hands slowly slid from his balls to his shaft, caressing its length like you'd pet a puppy, watching it stir and thicken under my attentions. His other hand went down to the damp shirt I was wearing, pulling it aside to reveal one of my large breasts, the bright pink nipple already hard because of this electrifying situation. He pushed the other side of his shirt over as well, revealing my other breast. I sucked a little harder on his thumb, looking up at him as he looked down at my milky white chest. He slid his thumb from my mouth and trailed his fingers down my neck, cupping one of my breasts in each of his hands and curling his fingers underneath them for a firm squeeze.

"They are real," he said, as if the thought had been killing him this whole time.

"As real as you are, baby," I said. Baby? As soon as the word left my mouth I felt stupid, but he smiled down at me and pushed my breasts together, staring wide eyed at the resulting valley of cleavage he created. E cups are large, I'll admit, but I suppose when it's on a five foot nothing frame like mine they looked as comically large as his cock did on him. He was pleased with them. He towered over me, well over six feet tall, but my chest was still a hefty handful for him. As soon as he got a good grip on my breasts, his cock started to stand up. Apparently he was a boob guy. As it inflated, it pointed directly at me, perfectly straight, and that small perfection was enticing.

I kept stroking his shaft with my fingers as he took his time squeezing and kneading my breasts like they were stress balls. I thought about how he said he was tried from a long day at work and wondered if my breasts were literally becoming stress balls for him, a way to relax and unwind. It felt nice, I didn't mind one bit. After a while I wrapped my fingers around his girth and wasn't surprised that my fingers couldn't wrap around him fully and touch together. I used the slackness in his skin to keep a decent pressure with both hands without causing any friction. As he got harder though, that slackness disappeared and soon my hands were sticking to him if I squeezed too hard. I knew that if this would go any further, we'd need some kind of lube. He pinched my pink nipples between his forefinger and thumb, twisting them just enough so I could feel it but not enough to be uncomfortable.

As his cock swelled up to full size. I was relieved that the length didn't increase that much, just the girth. He was a shower after all. Thank god. I noted with some amusement that he was bent over slightly, pulling his hips away from me because if he didn't his cock would have pushed right into my face. He was being patient, letting me take steps as I was ready for them instead of manhandling me. With both hands he jiggled my breasts, almost slapping them together a few times, and watched with wide-eyed glee. "You like those, huh?" I asked, chuckling.

"Baby these might be the best I've ever seen," he said. I rolled my eyes. I highly doubted it, but I was flattered nonetheless. He continued to play with my chest like it was the first time he'd ever seen boobs and I finally felt bad for him having to bend over. I reached forward and cupped his heavy balls, lightly pulling them toward me to coax him forward. To his credit, he didn't shove his meat straight into my mouth but let me guide him where I wanted him. I pulled him forward so he was standing normally again and let the tip of his cock rest on my shoulder while I turned my head and kissed down the length of his shaft. I used one of his thick, throbbing veins as a road map and even let my tongue flick out of my mouth every so often to taste him. He was salty, but in a good way.

I kept kissing my way down him, massaging his balls with my hands and letting him play with my breasts, slowly working up the courage to get further but doing my best to show him I was eager and willing. As I approached his balls, I got a little more liberal with my tongue. They were much too large to fit inside my mouth, but I held them to my face and licked at them as if they were one of those mega sized jaw breakers. He moaned. It as a hungry, desperate moan like that of a starving man who just had a bite of New York strip. For some reason that made up my mind. One way or another, I would empty this stupidly hung black man's balls. As his cock head rested on my shoulder, I lovingly nuzzled in to his shaft, pulling on the skin of his balls with my lips and licking the base of his shaft like I was worshiping it instead of merely teasing.

He noticed the difference in my enthusiasm and rubbed my nipples to say thank you. I used one of my hands to grasp the tip of his cock from my shoulder, holding him steady as I licked up his length with more passion than before. My tongue slid over his veins and massaged the thick muscular bulge on the belly of his shaft. I used my grip on his cock head to lift his meat over my face back and forth so I could give both sides equal love. As I worked my way up to the tip, his hands continued to play with my chest, something it seemed he would never tire of. He pushed them together, squeezed them, jiggled them, played with my nipples, anything that he felt like in the moment and I enjoyed every second.

I wrapped my lips around the swollen tip of his shaft and it was like trying to suck on a Coke can. I let go of his cock with both my hands and explored his body. My right hand went up to his toned six pack while my left hand drifted toward his powerful and muscular thighs. He was in fantastic shape, much better shape than me, but I tried not to be self conscious about it. Obviously he wasn't bothered by a curvy little white girl because he was practically drooling over my hefty bosom. I appreciated the fact that while he was very muscular, there was still a thin layer of fat that softened the edges of his physique, making him look less ripped but more comfortable. Nothing turns me off faster than guys with bulging veiny muscles that scream of steroid use. Bulging veiny cocks on the other hand...

I relaxed my jaw and tried to take more of my Adonis into my mouth. He didn't once attempt to push. Having plenty of experience he probably knew it wouldn't help. I had to take my time, warm up to him and get there on my own, which he was more than happy to let me do. My hands slid from his abs and thighs around to his butt, which was as chiseled from marble as the rest of him. I used it as a handle to pull myself forward, relaxing my mouth and making some slow but steady progress. "That's it baby. Take your time, you can do it," he said, patient but hungry.

His hands continued to play with my chest, occasionally running through my bright red hair, but never pulling my head toward him. After a few more minutes of me sucking on his tip like a lollipop, slowly accepting more and more into my mouth, one of his hands slid from my breasts and down my stomach. His warm fingers slipped passed my belly button and wiggled between my thighs. Without a second thought I opened them for him. I was surprised at my own eagerness. I was the timid goody two-shoes, not a vixen like Courtney. Letting a man fondle me like this was not my MO. A thick finger massaged over the skin of my clit for a moment before slowly sliding down further until he found my vagina. His finger slipped in almost effortlessly. I moaned onto his cock head.

"My god, Miss Hailey," he moaned back. For some reason when he called me 'Miss Hailey' I felt prestigious or honorable somehow, like he had given me a title of immense respect. To my surprise, he pulled his hips back and removed his cock from my mouth. I looked up at him, disappointed, and watched as he laid down on the couch next to me. "Straddle my face and let me taste you, but keep doing what you're doing," he said. My first thought was Thank god I shaved this morning! followed by Oh god, I've never had a guy down there before. I had never had a dick the size of my forearm inside my mouth before either, so tonight would be full of firsts. I didn't know what to expect, but I was determined to do what many women before me could not. If he wanted to sixty-nine, then damn it I would figure it out.

I crawled on top of him and turned around, self conscious that he was looking directly into my booty but I figured I would have to shake that pretty fast if I was going to enjoy this. He made it a little easier when I reached up with both hands and pulled my hips toward his face, adjusting us both effortlessly until he was in a spot he liked. He was eager to start, he wanted to taste me. I felt his warm tongue glide across my lips and my concerns melted away. It felt so damn good. His big hands squeezed by thighs as he worked magic with his mouth. I let out a few moans and relaxed on top of him, enjoying the feeling of his tongue sliding between my vagina lips and tasting me like he was trying to get the ice cream out of the bottom of the cone.

Lost in the pleasure, I had completely forgot about his cock until he flexed and it lifted to bump against my hanging breast. I noticed that my nipple immediately grew cold. I looked down and saw a clear, sticky liquid coating my nipple where his cock head bumped it. I thought it was my own saliva until I lifted his shaft with one hand and watched as more of the viscous fluid oozed from the tip with my grip. Curious, I bent down and licked it. It was sweet and a little sticky, like watered down honey. I wondered if this was the fabled precum I had read about in my dirty stories. Whatever it was, I liked it.

He moaned as he licked my vagina and the sensation of vibrations from his deep voice almost made me shiver in excitement. I relaxed my thighs and fully embraced his oral pleasures, relishing the feeling as he probed and explored with his tongue, sucked and pulled gently with his lips, dug his fingers into my thighs. I wondered if vibrations from my throat would make him feel good too, so I took him into my mouth as far as I could manage and let out a moan. My moan came out muffled thanks to the throbbing python in my mouth, but I felt him twitch and heard him moan again as I did. With my jaw warmed up and my body relaxed I could slowly bob my head up and down the first few inches of his cock without bumping my teeth. As I did, I felt a certain erotic energy forming beneath me.