Disclaimer: This story is a Chris Jackson fanfiction and is not to shared, posted, downloaded or distributed without my permission or credit given to me. This content is for mature audiences only. All characters are over the age of 18. These are completely fictional events and are for entertainment only.
Life’s been good to me so far, I guess. It hasn’t been horrible. Not since it became my own life, and not someone else’s. Once I had the tools to strike out on my own, things got good. Not fantastic. Not a dream life. But it’s better than where I came from.
Things got even better for me when my estranged father passed and left me enough money to leave my hometown and restart in my dream place; Ibiza. Ibiza had been my dream location since I read about it on a travel blog. I had never even been there before, but once I saw the egg I inherited from my dear old dad, I took the leap.
When I landed from said leap, I was able to use my work experience to land a bartending gig at one of the many resorts in the area since the last bartender there had retired. I understood why the man (or woman, I wasn’t sure) would want to stay here till retirement.
The resort was right on the crystal-blue ocean, and the bar was an outdoor attachment on the main resort. We served beach patrons of all makes, models, and appearances as they hung out on the beach, swam, sunbathed, and played volleyball or frisbee.
Speaking of models, there was a woman who looked like she should be one walking right towards me. I pretended to wipe an already spotless piece of the cherry wood counter—I think it was cherry wood. It was dark and beautiful, but I’m not a tree doctor.
“Hey there,” the woman said calmly. She leaned onto her elbows on the bar, looking at me from under a curtain of chestnut, wavy hair.
I looked up from my polishing cloth and smiled. “Hey.” I replied, trying to keep my voice as relaxed as hers. “Need to see a drink menu?” This girl was hot and she knew it. She didn’t need me to trip all over myself to tell her.
“How are your mojitos?” the mysterious bikini babe asked. I met her almond-shaped brown eyes and had to remind myself how to speak.
“They’re a pain in the ass to make. Which means they’re good.”
The woman didn’t laugh, but her smile was bright and genuine, clearly entertained, and not put off. “Sorry to do this to you, but I’ll have one of those.”
“I was afraid of that.” I sighed dramatically as I grabbed a small fishbowl. I made her drink in silence, and she watched me the whole time.
“Not much of a talker?” Did she want me to keep talking? She was so far out of my league.
“I can be if I feel like the customer wants me to talk. Unfortunately, I don’t always pick up the vibe right.” I shrugged apologetically.
“Yeah. I can tell.”
I lifted my head from the glass that I had just put soda water into. She was smirking, having made a joke I had just caught onto. “I’m going to warn you right now that I am abysmal at small talk.”
Her smile widened again, back to where it was when I told her I hated making mojitos. “Is there anything you are good at?”
I tilted my head to the side, trying to figure out if that was a loaded question. “Making mojitos,” I settled on as a safe answer, handing her the drink.
“I’ll be the judge of that,” she said softly, her fingers grazing mine as she took the cold glass. As she took her first sip, her dark eyebrows rose. “The jury is already in. You are good at making mojitos. I’m sorry.”
I laughed this time. “Is that to say this won’t be the only one you’re getting from me?”
She laughed this time, dazzling white teeth looking even brighter as they contrasted the deep caramel skin around them. “You’re starting to get my humor.” The mystery woman twirled her curly light-brown hair around a finger. “You don’t have a name tag. Do you have a name?”
“Of course I have a name. Who doesn’t?” I scoffed as I used a microfiber towel to get water spots off a freshly cleaned glass.
She blinked before shaking her head. “Your name, dude. What’s your name.”
I smiled, and she face-palmed, her cheeks becoming a cute rusty shade. She was learning that I had a sense of humor, too. “I’m Finn. And you?”
“Ashley,” she said with an easy smile, her hand held out. I shook it, and inwardly marveled at how perfectly soft it was. Vastly different from my chemical and hot water abused hands.
I kept actively trying not to look at the crazy-hot woman and did what I could to focus on working. It was only two p.m. and not quite rush hour. There wasn’t much to do. Ashley kept taking little sips through the blue swizzle straw. And looking at me.
“You don’t know who I am, do you?” she finally asked.
I met her warm, brown eyes and shook my head. Apparently, the anonymity she found with me was enough to make her smile raise to her eyes and her shoulders relax. “You’re a musician?” I guessed.
“Ashley Moore. Actress. Model,” she corrected me with a lowered voice. Apparently, I was the only one she wanted the attention of at that moment. “TV roles. Commercials. A B-movie or two. I’ve done Sports Illustrated and Victoria Secret modeling.” Her grin, her posture as she leaned on the bar, challenged me not to look down at the cleavage displayed in her blue bikini top.
“I believe it. You’re in fantastic shape, and that curly hair of yours? I dig it.” I leaned back against a beer cooler and crossed my arms over my chest. I continued, “The model part makes sense. You’re what… five-eight? Five-nine? Perfect model height.”
Ashley leaned back to sit up fully. “Wow. You’re good. I gave you the chance to perv all over me and say anything you wanted. But you stayed perfectly tame. Compliments, not deep-end objectification our construction guy talk.”
I tilted my head curiously. “Were you fishing for that, or were you hoping to throw half a mojito in my face?”
Ashley took a long, drawn-out sip through the narrow straw, dramatically slurping as she did so. It made me smile. “It’s too good to waste by throwing in your face. But… now that I have a feeling of what kind of guy you are….”
“And just what kind of guy am I?” I asked, popping up an eyebrow.
“The kind of guy that doesn’t understand how hot he is,” she told me as she reached for a cocktail napkin. “Got a pen nearby?”
I looked around for half a minute before finding one by the till. “Sure.” I handed her the simple Bic.
“You can call me Ashley. But we already covered that. And this is the number you can call me at,” she said with a wink as she handed me the napkin.
—
Once my shift ended, I had a hot girl’s phone number burning a hole in my pocket. But for some reason, my dumb ass wasn’t smart enough to give her mine.
I took the cocktail napkin out of my back pocket and punched the number into my phone.
Hey. It’s Finn. Forgot to give you my number too. Was going to let you text first so no pressure, but…. I was never a fan of the three-day rule. Also, she was either here on vacation or for work, so I figured there was no time to waste.
Her reply was immediate.
Rm 304. Don’t change. Don’t shower.
Well, that was straight forward. I wasn’t going to argue against it, though I would have liked to freshen up.
Instead of heading to the bus stop, I went into the luxurious resort. It was out of my price range, but a job perk was one free night a month, or I could save them for a longer stay. PTO was also unheard of for a barkeep where I came from, which made this gig better yet.
I found her room easily, following the clearly marked hall signs. After only working here for three weeks, I had never even seen the inside of a resort room.
On my second knock, Ashley opened the door. When she did, my fist was frozen in the air. My mouth went dry but felt like it wanted to water.
“Uh… hi,” I said lamely. “Don’t take this as disappointment, but this isn’t what I imagined.”
Ashley smiled and leaned against the doorway, twirling the cord of her open, satin burgundy bathrobe. “You like it, don’t you?” Her pout was teasing and cock-hardening.
“Do you want me to say what I would if you were a bar patron, or what I’m really thinking right now?” I asked, my eyes glued to her impossibly tight body.
The model and actress smiled and stood up fully. She grabbed the panels of her robe and slowly opened it, showing me more of her. “I’m in my suite and you’re off the clock. I’m wearing garters, a demi-cup bra, and crotchless panties. Of course I want to know what you’re really thinking.”
“What I’m thinking about is why a girl like you is going through this kind of trouble for a guy like me,” I said, stepping into her suite and closing the door behind me. She didn’t back away.
“Maybe I like the thrill of sleeping with guys that shouldn’t realistically have a shot.” Ashley quirked a perfectly tweezed brow. “Is that a problem for you?”
I shook my head as I stood there. Watching her. She was maybe a half foot shorter than me, but I could feel the attitude, the fire in her, from where I stood. She’d be leading the charge tonight. And I liked that.
“Not a problem,” I said flatly. Her pushing my back to the solid wooden door wasn’t an issue either.
“Don’t worry. I’m clean. I also don’t do this as often as my last few words may have suggested.” Ashley cupped my jaw and looked up at me. “It’s not very often I find someone I want to go all the way with.”
Ashley leaned in and kissed the exposed skin of my neck as she reached down to undo my black leather belt. “Most guys get over-confident or can’t find their tongues. But you?” She pulled my belt out and cracked it like a whip. The smile on her face was utterly sinful when I didn’t flinch.
I leaned down and kissed her, showing her I was in. I didn’t try to push my tongue into her mouth, though. This was her rodeo, and I was glad it was my cock she was choosing to ride.
Her tongue darted out and traced my lips before I opened for her. Ashley undid my pants and pushed them down as we kissed. She didn’t need me to let her dominate the kiss. She did it all by herself.
I had never been the kind of guy to follow a lead. But I usually initiated. I usually had a way of attracting shy girls. Not inexperienced girls, but girls that let me take the lead because I was bigger.
But Ashley wasn’t here to play games. She made that very clear when she let her dark red robe fall to the floor. Her bronzed skin positively glowed in the soft yellow wall-lamps. She didn’t fall to her knees, but gracefully lowered herself into a deep squat, dragging her nails down my work polo as she went.
“I need to feel what I’m doing to you.” She made a low, rumbling hum like a stalking predator as she undid the front of my slacks and pulled the fly apart.
I wasn’t fully hard yet, but seeing this powerful, seductive Aphrodite of a woman in lingerie for a mortal like me left me with quite the bulge in my black briefs.
She scraped her long, crimson nails over the left leg of my pants while the nails of her other hand dragged over the pushed out micro modal of my underwear. “I can have some fun with this,” she said huskily, appraising me.
I never measured my own dick. I didn’t spend time with other naked dudes. I had absolutely no idea how I’d compared to other guys. But watching Ashley put her nose right to the soft black material and inhale my scent removed any self-confidence issues I could have had.
“You smell like a fucking man,” she groaned before wrapping her full lips around my covered bulge. She ran her tongue over it before leaning back. “You smell like work, but you smell like a man who keeps himself clean. Let me see it properly. I need to taste it.”
I put my hands in her silky, curly hair, running my fingers through it as she pulled my underwear down.
“Fuck,” she groaned. “Look. At. This.” I didn’t think I was anything special, but she either did, or she just liked dirty talk. I couldn’t tell which it was, and it didn’t matter. It was fucking hot.
I watched as she pressed her nose into the soft skin between my sac and my cock. She inhaled again and then licked. She was dirty, insatiable, and her body was fucking insane. I didn’t deserve this.
“Remember I said these were crotchless panties?” Ashley asked before spitting right on my dick. “That wasn’t a lie. I love sucking cock, and I love touching myself while I do it.”
I watched her sharp brown eyes as she licked up and down my rigid shaft as her hand went over her panties and between her legs. If I had called her bluff, I would have been a fool because I could see, could hear her fingers disappear.
She moaned as she started to move her arm. I was torn between watching her hand move between her legs and watching her lick up and down my hard cock. It was the hottest thing I have ever seen.
Ashley used her free hand to tilt my cock down, and she took it between her puffy, glossy lips. The sounds of her slurping paired perfectly with the wet sounds of her fingers fucking her cunt.
“Jesus, Ashley. You’re filthy. I fucking loved it,” I told her, a growl in my own voice.
She popped off my cock and licked a running string of spit. “Yeah? It usually turns guys off. They me, the perfect skin, the toned body and my hair. They want a delicate model.”
I shook my head as I pulled her hair into a ponytail. “Not me. I want to watch you do whatever you want to me.”
Ashley looked up at me like I gave her the keys to her dream car. “I want you to use that ponytail as a handle, Finn. I want you to fuck my pretty face.”
The hottest woman I had ever seen opened her mouth wide, and I pushed my hips forward. She stuck her tongue out, letting the length of my cock slide across it as I moved into the moist and warm cavern.
Her hand started moving between her legs again, and she began to mewl as I used my hips. I slid in and out, letting her hot tongue feel the veins, let her throat get accustomed to the big, soft crown.
She nodded at me, and I took it to mean she was ready. I drew back, leaving just the tip on her tongue, and then I surged forward. I didn’t stop until I felt the back of her throat. Ashley pushed her head forward, demanding the press of my head against the spongy back of her head. Her eyes watered before she slid back.
She wanted it rough. She wanted her makeup ruined. I was happy to oblige.
I wrapped her hair around my fist, and I saw her eyes smiling at me as I pulled, tilting her head back to hit a new angle. The excitement in her eyes was unlike anyone’s I have ever seen just having a heavy cock in her mouth.
I pulled back and rushed back in, feeling her saliva rush around my length until I felt the muscles of her throat squeeze my head. Jesus Robert Christ. This insatiable woman didn’t just want me deep. She wanted to wrap her throat around my dick and choke it.
The gurgling noise she made around me as she produced more saliva was unlike anything I had ever heard. Ashley was so fucking hot, so luxury, but such a dirty thing!
As I continued to fuck her face like she so eloquently asked, spittle and glossy precum escaped the corners of her elegant mouth, defiling her gorgeous face in a primaly beautiful way.
Here was the most perfect woman I had ever seen, squatting low, letting me ram into her throat and not wiping away the tears she let me squeeze out of her. The sounds of her fingers plunging deep into her soaked pussy was every bit as, loud as my cock digging into her throat.
I usually wasn’t a deep oral guy since the majority of head bliss comes from my tip, but with Ashley, watching her willingly take everything I had to offer was too good to turn down.
She tapped my leg three times; a pretty universal sign that she needed me to stop at once. I quickly pulled out and she coughed and spluttered.
I dropped down to my knees and put my hands on her shoulders. “Are you okay? Did I go too deep? Did I hurt you?”
Ashley smiled and shook her head. “I’m fine, Finn. Just needed air.” She giggled and gasped. I looked down and saw her wet, creamy fingers reappearing. Sucking dick really did turn her on.
She raised her hand, about to bring them to her lips, but I took her by the wrist and changed the direction, bringing them to mine. Ashley’s eyes hooded over as I sucked her warm and tangy fingers, cleaning them off with my tongue. She tasted so fucking good.
“Bend over the bed. It’s my turn to taste you.”
She smiled devilishly and I helped her to stand. Her legs were shaking, and I put two and two together; she brought herself to orgasm while sucking my cock. I was more than willing to clean her up.
“Don’t tell me to bend over the bed, Finn. Make me bend over the bed.” Ashley showed me exactly what she wanted by taking my wrist and putting my hand on her own throat.
I squeezed my fingers around her neck, not too hard, and making sure not to constrict her airway. A smile took over and her eyes glowed at the safe but possessive hold.
“Yes,” she hissed as I steadily but forcefully walked her across the spacious suite. The hardwood floor under my shoes, under her bare feet, squeaked softly as we moved in our dark tango. Her hand was on my wrist as her knees hit the bed. She wasn’t pushing me, but holding.
I let go, and she let me spin her, putting her ass against my spit-soaked, erect cock. I moved my hips, flexing my abdominals to fuck her ass cleavage. The silk of her panties between her ass felt amazing. Then I remembered again that her panties were crotchless.
Bending my knees just a bit, I slid by cock between her fit thighs and stood back up, nestling the top of my cock between her soaked pussy lips. I wasn’t inside her, but I moved back and forth, sliding between her lips, making her gasp.
“Oh my God,” she moaned, reaching behind to thread her fingers through my short, dark hair at the nape of my neck. “Angle a little higher. Yes! Right there! Yes! The head of your prick is bumping my clit! That feels so good! Fuck!”
Ashley began bucking her hips, riding my cock between her legs like a horse, and I didn’t care she was still partially dressed. I didn’t care if I was still fully dressed with just my pants open. This was some of the most spontaneous action I ever had.
With a wildcard like Ashley, I figured it best to keep things moving. To keep things fresh. I pushed her down, crushing her chest to the bed. I unclasped the back of her bra but left it there. There was something hot and rushed about seeing the clasp open, her back fully exposed, but the straps still on her shoulders. A kind of vulnerability and promise while her tits were still covered and hiding from me.
I held her down with a hand between her shoulder blades.
“Do it! Fuck me hard. Don’t you dare hold back because you’re afraid of hurting me.” Ashley was seething, and I had a feeling I was catching some buried resentment built from a string of lovers that didn’t trust her to know what she wanted.
Well fuck them. I was going to give Ashley the hard dicking she deserved. With my hand not holding her down, I took my throbbing cock and lined up. No teasing. That’s not what she wanted. I surged straight in, not stopping until I was all the way in with one measured thrust.
“Fuck!” Ashley yelled, and I was afraid I hurt her. “Just like that! Don’t try to make love. Fuck me!” The moans that left her lips as I pushed and pulled my hips while I held her still would be enough to get myself off a week after she’d left.
Again, the spice of fucking Ashley Moore was variety. I let go of her upper back and grabbed her arm. Placing it on her lower back, I grabbed the other and pinned her wrists together.
“Yes! Fuck yes! Own me for the night, Finn! Make me feel like this fucking pussy is yours!”
“It is mine. It’s mine as long as you want it to be.” I pushed into her hard three more times, my thighs slapping hers, and then I stopped.
“Nuh-uh!” Ashley shouted worryingly. “You didn’t cum inside me already, did you?”
“No.” I shook my head from behind her with a chuckle. “I just realized that I said it was my turn to taste you, and I skipped right past that.”
“Oh. This is good. Don’t even-” Ashley’s words were cut off by a low moan as I slid my hard cock out of her. It was then replaced with a sharp gasp as I spat on her pussy and moved it around with my tongue. “Oh! Shit!”
Ashley’s fingers, and then my cock, her overall arousal, had opened her pussy, and made it good and wet for me. Her flavor was heady and tangy, intoxicating, and copious. There was plenty of it to lap up and collect with my broad tongue.
My lover for the evening pushed her ass back into my face, but she didn’t try to break my hold on her wrists. She was loving being held down, loved letting me explore her hole with my mouth.
And I loved doing it. I fucking love eating pussy. My timing couldn’t have been better because as my nose pressed against Ashley’s brown little asshole, and my tongue slipped between her flared lips, she came with a sharp cry.
Ashley’s liquid joy flushed into my mouth, and I hummed contentedly as I tried to slurp as much up a I could. It ran all over my mouth, chin, and I could feel it dribbling down my neck. I had never felt a woman cum on my face like that before, but I wanted to feel it again.
To get what I wanted, I pushed three fingers into her pussy with my free hand, and I felt her inner walls grip onto my digits as her orgasm slowly faded. I wanted to bring another one right back, so I started sawing my fingers in and out, shallow but rapidly.
“Tell you when you’re about to cum, okay?” I shifted on my knees and buried my face between her light brown ass cheeks. I licked her asshole with a quick, flickering tongue.
She hissed at the unexpected sensation, but she managed to ask her question. “Why should I tell you? So you can ruin my orgasm? So you can deny it?”
I lifted my head briefly. “No. Fuck no. Not unless you told me you wanted that. I won’t deny you anything.” I spat on her asshole and let go of her wrists so I could press against her rosebud with the tip of my thumb.
“You’re going to tell me when you cum so I can put my face right in it. You’re going to cum all over my face, and I’m going to drink it down.” I bit her ass cheek hard enough to leave marks, and she buried her stunning features into the white duvet.
“Fuck!” She screamed into the soft material as I plunged my fingers deeper into her, stretching her more. “I’m so close again! H-how?” Ashley was shuddering, quaking, and squeezing my fingers.
A kind of heavy pride swelled in my chest as I realized that telling Ashley just what I was going to do to her helped push her to the edge.
“How are you so close already? Is it because you’re a needy slut that loves hearing what men want to do to you?” Her cunt crushed down on my fingers again and I grinned as I pushed and released, pushed and released, on her asshole. “After your next orgasm, I’m going to rip my fingers from this warmed-up pussy. I’m going to slam my fucking cock back into it, and I’m going to breed you.”
Ashley grabbed the duvet with both hands and bit the cotton covering as she tried not to scream. She was hot and so fucking wet around me. The squelching sound was so fucking loud. I bet if anyone walked by the door, they’d hear it.
“You are so fucking wet for me.” I growled and spat on her asshole again and pushed again with my thumb. Her asshole relaxed, and I popped the tip in. “Good girl. Taking my thumb like that. If I had lube, would you want me to take your ass?”
“Yes! God yes!” Ashley moaned, pushing her hips up to take more of my thumb. My shoulder was starting to burn from finger fucking her so hard, but I knew she was damn close again. “I want you to ruin all my holes, Finn!” She gasped and her body bucked uncontrollably.
She didn’t have to tell me. I didn’t think she could. Ashley was convulsing around my hand. I pulled my fingers out and she bit the duvet again as I plunged my tongue into her widened entrance.
“Oh! Ah!” Just sounds. She couldn’t form words as I forced another orgasm out of her system and right into my mouth. Just like I wanted. It gushed in, and I let it wash right into me.
I covered as much of her cunt as I could with my open mouth and drank down the waves as she came. I didn’t care how soaked my face was. She was fucking delicious, and she was trusting me with her needs, trusting me with seeing her like this.
When she came down from her third orgasm, she was breathing hard. She was glistening with sweat and looking so fucking sexy in the warm glow of the wall lamps.
I gave her time to recover. I licked the salty sweat off of her ass, and from her back. The tired little mewls were so fucking cute after having wrecked her with a third O.
“Finn, I’m not sure I can….”
“Too sensitive?” I asked softly, playing with her hair. She nodded and looked at me with tired, apologetic eyes. “It’s okay,” I assured her softly.
Ashley managed to roll herself over, and her demi-cup bra slid down, finally showing me her perfect tits capped with dark brown nipples. Her pussy was trickling, hairless, and practically shimmering in the golden light.
“You are so fucking perfect,” I breathed, cradling her cheek in my hand.
“You’re not upset you can’t cum in me right now?” Ashley asked, pouting.
“No ma’am,” I said, shaking my head. “Even this was incredible.” My cock was still rock-hard, in case she needed proof.
Ashley adjusted herself on the bed and wrapped a hand around my dick. She pumped it slowly and looked up at me. “I still want you to cum. You’re not leaving until I see this cock toss ropes out of it like Popeye.”
I couldn’t help but laugh. One of the hottest women on the planet was jacking me off, refusing to admit defeat, and making old cartoon references. A cynical part of me was glad she was just passing by the resort, because I was too damn good at falling fast and hard.
“I’m going to suck you until you cum, but I want it on my face, okay?”
How could I do anything but nod and happily feed my cock into her open, waiting mouth?
Her lips closed around me, and her eyes closed. Ashley started to lazily suck, her tongue swishing over my sensitive tip bottom.
I didn’t feel the need to fuck her face again, but I did use a hand to massage her pubic mound as she kept paying sweet attention to my frenulum.
Ashley knew exactly how to give sleepy head, and I had a feeling this wasn’t her first time. I hoped she was doing it on account of being so thoroughly used, as opposed to doing it for other guys out of lack of interest.
The way she looked content and sated made me think it was the former. She said she loved sucking dick, and the way her tongue knew just how to target my frenulum, had me believing she was as happy doing this as she was getting skull fucked.
“Ash, we’re close. We’re really fucking close,” I panted.
A new fire lit in her eyes, my need being a second wind to her. She sealed her lips a little tighter and she sucked my cock head like she was trying to get the last drops from a juice box.
“Ashley! Ashley! Fuck!” At the last second, when I thought she was going to have me cum in her mouth, she popped me out.
With her tongue out, my balls felt like they shattered, and I painted her face with the pearly ropes she so sweetly demanded.
I groaned with the force, the straining pulling sensation of my balls evacuating. It felt like they were trying to leave my body and not just empty themselves. My head wanted to fall backwards. My eyes wanted to roll back. But I kept focused on her face even as my vision threatened to swim.
The sight of Ashley Moore catching my cum with her cheeks, forehead, tongue, and right into her mouth was so fucking worth it. Her hand that picked up speed to make sure she had wrung out every fucking drop was worth it.
I just kneeled there, heavy breathing like a savage because the prettiest girl I had seen with my own two eyes had just worked my brain out of my dick.
Once I could see and speak again, I asked, “So you want to hang tight while I get you a towel?”
She smiled prettily like she was having her photo taken in a field of flowers. “No,” Ashley cooed. “I want you still on my face when I open the door for room service. And I hope you’ll be ready to breed me once I’ve had some time to cool down.”
If Ashley was only here for a day or two, I had a feeling she was going to get good mileage out of me.