Hailey's Sexcapades: I Got Caught Skinny Dipping
- 3 months 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 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 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 what 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.
“No, I mean how come you’ve never been skinny dipping before?”
He looked 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.
“It’s your house, get comfy.”
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.
“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.
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% 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 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 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 instinctively 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.
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. I figured I would have to shake that insecurity pretty fast if I was going to enjoy this. He made it a little easier when he 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.
Every so often his hips would come up, pushing his meat a little further into my mouth, but then he’d let out a quick breath and return himself back to the leather couch. Each time his tongue would venture inside me as compensation, like he craved to go hog wild on my mouth but knew he couldn’t and instead focused his passions on me.
The moans and panting grew. I kept up my bobbing motion, taking him into my mouth as far as I could each time and letting my nipples brush his thighs as I lowered myself down. He seemed to like that, even going so far as to release my thighs so he could get a quick handful of breast before returning to my thighs to keep licking me.
Before long the sexual energy and tension was reaching a tipping point. I felt how eager he was to cum, how excited he was to have a curvy redhead who wasn’t afraid of his admittedly intimidating manhood. A switch flipped. He stopped licking and exploring my nethers and instead focused all his attention on my clit with remarkable agility. I did my best to keep bobbing my head up and down his shaft, but waves of pleasure coursed through me and it became hard to focus.
I instead sucked on the tip and used my hand to keep working his shaft, but even that became too complicated for my brain as his stimulation escalated. His tongue danced across my clit and I felt myself approaching an orgasm. I removed him from my mouth entirely so I wouldn’t choke on him, but I didn’t want to leave him without stimulation so I leaned over and licked his swollen kiwi-sized balls as my thighs shuddered.
My eyes shut tight and the shudder from my thighs spread to the rest of my body. I instinctively started grinding my hips into his face as my orgasm took hold. Part of me was worried he wouldn’t be able to breathe, part of me didn’t care. I felt more than heard him moan, because my moan was too loud to hear anything else.
I sucked desperately on his balls, trying to ride out the waves of pleasure and let him know I hadn’t forgotten about him too. As my hips shifted and squirmed on his face, it became difficult for him to be precise with his pleasures so he opted to lick anywhere his mouth could reach, even going so far as to pull my hips down toward him for a better angle.
The sensations built up, bordering on too intense. Once my voice cracked and my thighs stopped shaking, he leaned his head back onto the couch and gave me a break from my own intense orgasm. I felt his lips and tongue gingerly touching me, like he was giving dainty kisses instead of the lustful licks moments prior. It took a few moments for my body to come down from the high he had bestowed upon me. I caught my breath as my cheek rested on his thigh and my lips played with his balls. It was lazy, but it was all I could muster after the euphoria he brought me to.
He let me catch my breath for a moment and patted my booty, gently pushing my hips away from his face. I took the hint and dismounted him, but kept playing with his balls as I wedged myself between him and the back of the couch. He pulled his hips away from my affections and sat up, facing me. “Lay back,” he said. My heart skipped a beat. Was he going to try to fit that thing inside me? I wasn’t sure if my vagina could handle it. I flipped over onto my back and scooted myself so that my head could lie on the armrest.
“Let me try to suck it again,” I said, trying to spare my vagina.
“I have another plan,” he said, and I was all but certain he was going to impale me with his cock. My anxiety waned as he crawled on top of me and straddled my chest, plopping his heavy meat between my creamy white breasts. Man, he loved those things. I guess I was glad he was getting some joy out of them, all they ever brought me was back pain and a lack of eye contact. He pushed my heavy breasts together, wrapping them around his thick black cock like he were a hot dog and I was the bun. He started to pump.
“You having fun, baby?” he asked, looking down at me with a smile as he humped my chest.
I grinned up at him, my face still flushed from my orgasm. “This night has certainly been full of surprises,” I said. Because of his length I felt the tip of his cock slide under my chin with each of his pumps. I tucked my chin to my chest and stuck out my tongue, letting his tip slide up it like a ramp each time he pushed forward. He gave me a big toothy grin when I did that.
“Not many women can handle this thing,” he said, lifting his shaft and lightly bouncing it against my chest, staring down at the resulting boob jiggle before he resumed his pumping.
“Not many are as… well equipped as I am,” I said, giving him a coy wink.
“You’re the perfect size to handle a man like me,” he said, pushing his hips harder now so I could feel his heavy balls sliding along my ribs.
“Maybe you’re the perfect size for a woman like me?” I asked, sticking my tongue out again and sucking on his tip as it slid in my mouth. I wasn’t sure where my sexy confidence was coming from, but I could tell he liked it. His pace quickened. With his large, warm hands he pressed my breasts tight around his cock, trying to create more friction as he pumped into them.
I kept my chin down, accepting his tip into my mouth while staring up at him with my big green eyes. He stared down at me first with joy, amused by our banter, but the joy turned to lust. I could tell he wanted to finish, and he was going to use my chest and mouth to do it.
I reached up with both hands, lacing my fingers over my nipples and using my palms to put extra pressure around his cock. With my hands in place, he braced himself with one hand on the back of the couch while the other slid through my hair and held the back of my head. He didn’t pull my face toward him, but I could tell he planned to.
I kept staring up at him, squeezing his shaft with my hefty breasts and flicking my tongue along his swollen tip until his breath turned to hungry gasps and his hips pumped harder. His face twisted into a funny shape as he tried to hold on for as long as he could. I would have laughed at the face he made if a torrent of warm sperm hadn’t shot directly into my mouth and practically flooded it with the first burst.
His hand pulled my head toward his cock and he shoved his hips forward so that his sperm emptied directly into my mouth, load after load like a fire hose. To avoid choking I quickly swallowed what I could, but it just kept coming, overflowing out my mouth and down my chin. He looked down at me with a face of pure rapture and I looked up at him with an understanding that he needed to be emptied. I felt his sperm oozing down my chin and pooling in my cleavage, but after the orgasm he gave me I was willing to let him ride it out and fill my mouth as he pleased.
With a heavy sigh, his orgasm subsided. I felt the weight of his butt relax onto my stomach while he caught his breath. With the threat of drowning gone, I swallowed what was still in my mouth and moaned. It tasted good. Salty and sweet at the same time, like a dark chocolate pretzel. Not at all what I expected.
He released his grip on my head and slowly pulled his cock out of my mouth. More of his seed dripped out from the tip and I leaned forward to lick it off. I then gripped the base of his cock with both hands and slowly slid up the length of his shaft, milking out every last bit I could get onto my tongue. He smiled down at me and laughed.
“Ah shit, you’re too much,” he said, watching me swallow a dollop of his milk. I licked my lips and blew him a kiss.
“Just enjoying my reward,” I said, a line I remembered from a porn video.
I looked down at the mess we made. His black shaft rested between my soaking wet breasts. It was actually kind of hard to see how much cum was on me. I was almost the same color. I smiled up at him. I did it. I did what many women before me could not. I released the carnal pleasures inside him and left him satisfied. I stared up at him, basking in my accomplishment, kissing the tip of his cock as if thanking it for its service.
“That was one hell of a warm up,” he said. I raised an eyebrow.
“Yeah, I usually need two or three of those to really feel empty. Especially since it’s been so long. But boy am I glad I found you,” he said, rubbing circles over one of my cum covered nipples with his thumb.
“You’re not empty yet?” I asked in shock, looking at the layer of sperm already covering me and thinking about the massive amount I was digesting.
“Not quite. But don’t worry, with you I think round two will be quick.”
I swallowed hard. I wasn’t expecting a round two. If I wanted to truly set myself apart from those other women, truly satisfy his needs the way no one else could, I would have to go along with it. Fortunately for me, he seemed pretty obsessed with my chest. I also liked - no, loved - the way he tasted so it would just be another fifteen or twenty minutes of fun and I’d have another protein shake. “Whatever you need baby,” I said, already wrapping my breasts around his shaft, which was still surprisingly hard.
“Whatever I need?” he asked. Something about the way he said it made me suspicious. I nodded up at him anyway.
“Anything,” I said.
He chewed on his lower lip for a second and then dismounted me. He put his hands on my hips and flipped me over so I was on my belly. I immediately thought all the sperm on my body would get on his nice leather couch, but he didn’t seem to care and I wasn’t going to ruin the mood by bringing it up.
I propped myself up on my elbows and looked back at him as his hands slid over my booty and between my legs. He slid a finger inside me, probing gently at first, then pushed himself deeper. I moaned. Watching him over my shoulder, I saw him slide his hand up and down his slick shaft a few times, then use the resulting layer of sperm coating his hand to lube up my thighs. I could see where this was going.
“I don’t know if you’ll fit,” I said as he crawled on top of me, already lining himself up. What I meant to say was That thing will split me in half.
“It’s ok baby, I’ll go slow,” he said. Nervous as I was, I believed him. The entire time he’d taken care of me and took my considerations to heart first. Terrified as I was of his monster dick, I somehow knew he would be gentle with it and that made me want to let him have me. His thick, swollen head pushed between my thighs and probed for my vagina. I felt him slip and slide over my lips, then push nice and easy between them.
My jaw dropped as he entered me.
To his credit, he went slow. Thankfully, I was wet from when he went down on me and we had a generous amount of his sperm to act as lube. Both of those things helped. But he still had to work it in slow, let my body get used to his size, then pull back to give me a rest before pushing in a little further.
Every few pushes he’d ask if I was doing OK, and even though I felt like I was being split open, I wanted to be there for him where no one else could, so I endured. As my body grew comfortable with his size, I got a handful of his sperm from my breasts and slid my hand down underneath me to re-apply the only lubricant we had. Then I remembered I had forgot to take my birth control that afternoon.
“How’s your pull out game?” I asked. I couldn’t do much about our ‘lube’, but I could try to prevent a flood of little swimmers trying to earn their gold medals.
“Don’t worry baby,” he said.
I don’t know what kind of power he had over me to make me be so reckless and irresponsible. Maybe it was because I wanted it as bad as he did. He had brought me to places I never knew existed, I was willing to go out on a limb and chance it happening again. He pushed in, this time deeper and deeper until he found the furthest depth he could go.
This man was basically a stranger to me, but I was letting him push his bare, cum-covered cock inside me as far as my body would allow it. He pushed against the barrier of my cervix and backed off, adjusting his hips a little and positioning his knees.
He gave me a few short pumps and asked me if everything felt OK. When he didn’t go too far to where it hurt, I nodded back at him. This whole process, getting my body used to his, took probably ten or fifteen minutes but he stayed patient and hard as a rock the whole time. With my body prepared and his adjustments made, he was ready to go.
I felt his big balls press down between my thighs and his hard shaft follow. I realized he picked this prone position because he could get extra friction from my thighs along the length of his shaft, since he knew I couldn’t accept his whole length inside me. That consideration for my comfort made me swoon.
Then he started to pump.
To him it was only the first five or six inches, but to me it was a bus. I relaxed my body, accepting his length and girth as he got his rhythm. Once he hit his stride, he laid his body down on top of me, pressing his muscular chest against my back and slipping his thick arms underneath me to cup my breasts. He really loved those things. His chin rested on my shoulder and he playfully licked my ear, sending a tickle down my spine.
I laughed, then moaned as he continued to pump his thick, black cock inside me bareback. He kissed my neck, sending another ticklish wave down my spine. “You feel so good, Miss Hailey,” he said, once again making me feel regal somehow. Despite his size he was tender, almost loving. It was a sensation I never expected.
“Yeah, do I feel good baby? Is my pussy gonna make you cum again?” I asked, inviting a little dirty talk. Again I surprised myself. It wasn’t even that vulgar, but I felt nasty for it and wondered if he’d judge me. What the hell was this man doing to my emotions?
“That tight little pussy is gonna make me cum so hard,” he said, and his pace quickened. I turned my face to nuzzle into his. He smiled and pulled at my ear with his lips. I felt my breasts jiggle in his hands with each of his powerful thrusts and ripples of pleasure coursed up from between my legs.
I was getting used to him, it was becoming more comfortable, and I was really starting to enjoy it. Not that I wasn’t before, mind you. He lifted his hips and changed angles slightly, which made his swollen cock head push against a part of me I didn’t know existed until that moment. My eyes bulged and my jaw dropped as he pumped against this magical spot inside my vagina, sliding his thick head over it with every hump.
“Oh my god,” I groaned out. A barrage of previously undiscovered sensations overtook me. If his oral pleasures were a Fourth of July fireworks display, this was a nuclear bomb. He kept his pace up, rubbing against this new spot and rapidly bringing my libido to it’s fullest and most hungry. His large muscular body was on top of me and wrapped around me like a cocoon, but I used what little movement I had to work my hips back into him and help him keep finding that spot over and over. He could tell I was working my hips against him, as if helping him to have his way with me. He liked that.
His pace quickened further, and I could not contain myself. I practically hyperventilated as another orgasm, this one ten times more powerful, wracked my body with pleasure. My thighs shook and my toes curled. My fingers balled to fists and my eyes rolled back in my head. I felt my vagina twitch and convulse around his thick, black cock and I let out a long, high-pitched moan and turned to a squeal by the end.
He kept pounding.
I felt his breath quicken and his body tense up. He shifted his position, ready to dismount.
“Don’t stop!” I ordered with a raspy voice. I wanted to keep riding this wave of ecstasy.
“But I’m -”
“It’s OK, cum inside me!” I demanded.
And he did.
He became harder than diamond and erupted like a volcano between my milky white thighs, flooding my vagina with his seed. My mouth was open as if I were shouting, but only a hoarse whisper came out. His hips fired like a piston, pumping load after load of his thick, hot sperm inside me and I didn’t care one iota.
For some reason I actually relished it. I laid underneath this charming, handsome black man who was basically a stranger not even an hour ago and accepted his seed without complaint.
He gripped my breasts hard and squeezed me tight against his body, like a hug from a long-lost lover. Perhaps we were long lost lovers in another time. It felt like my brain was transcending this plane of reality, so I was just about willing to accept anything.
My entire body quivered with aftershocks from his performance. His hips slowed down until he let out a long, satisfied sigh and pushed his length inside me as far as it would go to rest. As his cock deflated, he wriggled his hips to make sure as much of him stayed inside me as possible. We laid like that for what seemed like a long time.
“What just happened?” he asked. I could still feel his heart beat as he throbbed inside me and I imagine he felt mine through my breast.
“I think we just became friends.”