Scott was enjoying his first day at the resort. It was offseason and the summer crowds were long gone. He'd spent the day on the beach and there couldn't have been more than twenty people in all; and most importantly, they were keeping to themselves. It was just what he needed to get away from the recent events in his life.
After four years of dating his hometown girl, and eventually getting engaged, she broke it off to go out of state to pursue a college degree. It was a devastating blow to Scott's confidence and self-esteem. At least he wasn't being ditched for another man, just for what he considered foolish aspirations on her part.
At the age of 29 he'd already established himself as a commercial pilot, recently upgrading to Captain. He was making good money, enough for them to live comfortably on. She could have pursued a degree in a more leisurely fashion while enjoying married life. He sighed as he thought about what he considered her foolish decision, however what he really missed was her killer body and fantastic smile. He also missed sinking his thick, nine-inch cock deep into her three lovely holes.
As he stared down at his drink feeling a bit sorry for himself, he looked up in time to see a pretty, short-haired blonde with nice set of tits amble into the bar. She looked to be just a little over 5' tall, maybe 5' 2". She was in a swimsuit and had a cover-all on that barely conformed to the resort's indoor attire rules.
As she leaned on the bar ordering a drink, Scott was able to get a good look at her tight ass which was perfect for her smallish frame. The bartender motioned her to move down the bar for more convenient serving; in doing so, Scott got an eyeful of her hip sway as she walked. The cover-all couldn't quite "cover it all" as her lovely ass moved rhythmically up and down as she walked. As he watched her butt do its thing, he felt the familiar stirring in his groin as his cock began its ascent.
All he could think was, "Man would I like to tap that beautiful ass!"
As the blonde repositioned herself nearer to the bartender, she glanced around eyeing Scott sitting in the bar's semi-darkness. Her eyes lingered briefly on him then she turned back around waiting for her drink to arrive.
His initial thought was, "Oh well, she'll probably grab it and head out to meet some guy she's with. She's got to be spoken for. She's too beautiful to be flying solo." Scott chuckled at the irony of using an airplane metaphor to describe this blonde hottie.
Much to his surprise, when her drink came, she got up and started walking over to Scott's table and introduced herself as Sarah and asked, "Would you like some company in this empty bar?"
Scott motioned her to sit down, and she surprisingly took a seat on his side of the table. They struck up a light conversation trying to get to know one another a bit. As Scott got a close up look at Sarah, he realized she was what he'd always considered a deceptively pretty woman. The kind of girl who, the more you looked at her, the prettier she got. Her looks, coupled with a friendly and bubbly personality, were a perfect blend of beauty and charm.
Sarah's tits, now up close in the light, looked to be at least 36-38C, maybe even a D or DD cup. His cock bulged, and he was glad his pants caught the hard-on before it could fully tent pole within her view. A boner at this stage of their conversation would have been quite an embarrassment to him.
As they talked, Scott found Sarah's story of relational pain as interesting as his own. In her case, she'd been married to her high school sweetheart for seven years and they had a young daughter. He was the only man she'd ever been with, a fact Scott found hard to believe given her good looks and great figure, but apparently all true... "Well may be true," he mused.
Her husband had been, of all things, a youth pastor in a large church, where he'd served for four years after both of them had graduated from a Chrisitan college. Scott chuckled silently to himself when Sarah related the story of her husband having run off with one of his former youth group girls after the young woman had turned 18; a classic church world trope if there ever was one.
Sarah had struggled deeply with the betrayal, and for a long time during and after the divorce, her self-esteem and confidence took a major hit. However, with help from friends and parents, she had slowly pulled herself back together and was starting to feel good about life again. In fact, this trip had been a gift from her parents as they were folks of some financial means. They'd also agreed to watch Sarah's daughter, their only granddaughter, while she had time to get away and enjoy her first holiday since divorcing "that bastard," as her family referred to the Ex.
Before Sarah left, she'd even got the idea from her devout mom that now might be a good time to, "Learn that all men were not like her Ex. Some men really know how to treat a lady right...in EVERY way imaginable," as her mother put it. Sarah giggled as her mom finished saying that while slipping a package of Trojan Magnum XL Condoms into her palm and mouthing the words, "Use them." She remembered that her mom had some pretty wild years in her early twenties prior to getting married and "getting religion".
As Sarah talked, Scott got the distinct idea she was yearning to explore her sexuality during the vacation, sooner rather than later, and that's why she'd come over to his table in the first place. But Scott wasn't in a big hurry. In fact, he was enjoying the conversation with Sarah so much that he didn't want to push this into some "dash off to the bedroom" so she could experience intercourse once again.
Scott was having too much fun subtly steering the conversation with increasing innuendo, building her anticipation, and hopefully making her wet with anticipation. If all went well, he planned on introducing Sarah to his huge cock before the evening was over, drilling it deep into her man-needy cunt.
After polishing off their drinks, Scott suggested a walk on the beach since it was a nice, warm, moonlit night. Sarah readily agreed, thinking, "He's a romantic type of guy, how nice is that!" So off they went to stroll along the water's edge.
Scott kept the conversational innuendo going as they walked, and he could tell it was having the desired effect on Sarah. She kept giggling and laughing at just about every little joke he cracked, touching him lightly on the forearm every now and then. He'd learned from experience this was one good sign a female was probably raring to go, even to the point of "dropping her panties" before the night was over.
As they left the beach, Scott suggested they stop at his bungalow for a drink. Sarah was all for it. As they entered his room, she expected him to just start ripping her clothes off, engaging in some quick foreplay, then getting her in bed for some good old-fashioned fucking, which would have been just fine with her.
However, Scott surprised Sarah by taking a different approach to getting things started. He first mixed drinks for both of them then sat down in a large chair in the corner of the room. His hard-on was evident by the huge bulge in his pants, the classic tent pole effect, and now it didn't bother him for her to see it.
Sarah looked at him quizzically when he suggested they should have some fun first, thinking to herself, "Wasn't fucking me supposed to be our fun?" She was already feeling very aroused and wanted to get his cock inside of her as soon as possible.
Scott suggested she do a strip tease so that he could enjoy her seductive figure in motion. He wanted her to dance and slowly discard her coverall and bathing suit. Erotic dancing was not what she thought she'd be doing in his bedroom, but hey, "Whatever."
Sarah giggled and said, "Okay, I can do that for you, if that's what you'd really like me to do," all the while intrigued by his unusual request.
Scott queued some music, Sarah set her drink on the nightstand and started to sway back and forth. A bit shy at first, she quickly warmed up, increasingly getting into the flow of her sexy routine. She remembered how much she really enjoyed dancing and how long it had been since she had done any; years in fact.
"Maybe he'll take me dancing before the week is out?" she mused to herself.
After dancing for a while in front of him, bending over a few times so he could view her ample cleavage straining against her slinky bikini top, she sexily let her cover-all drop to the floor. She grinned at him, then resumed dancing, and finally bent over to get up in his face, displaying her cleavage to the point of a hint of areola and playfully shaking her breasts from side-to-side for maximum visual effect.
It was now time for the top to come off, so her "girls" could come out for some much-needed playtime with "the boys," or in this case, the man. Sliding the straps down her shoulders, Sarah stopped just before the cups slid off her breasts. She teased Scott, pulling at her nipples through the thin material, then dropped the bikini top off to the side giving Scott his first look at her bare breasts with their large, half-dollar sized, pink areolae. Scott's cock massively tent poled in his pants.
Sarah grinned, spun around and sexily swayed her ass back and forth in time with the music. She was really getting into it now, feeling really slutty. This was more fun than she thought it would be!
Next came the main event; time for Sarah to "cross the Rubicon," as the saying goes, and lose her bikini bottoms. He knew it, she knew it, and after a momentary pause, as if making one final contemplation of what she was about to do, Sarah went for it. She turned around with her round ass facing Scott, then slid her bikini panties down her butt, pausing mid-way for effect. She then slid them the rest of the way down her butt and sexily stepped out of them, kicking the bikini panties off to the side.
Sarah turned around and looked at Scott anxiously wanting to see his expression, and to also see if he was pleasantly surprised with the natural blonde bush between her pretty legs. She could tell from his reaction that he most certainly was!
He sputtered simply, "Oh man, I" as looked her naked beauty over. Scott had never fucked a blonde pussy before.
For Sarah, it just felt good to be naked in front of a man again. It had been quite a while since she'd bared it all for a guy, and it felt really good to have Scott looking her over with admiration and lust for her hot body. Without having yet touched her own pussy, Sarah could tell she was getting very wet.
Scott grinned his approval while simultaneously gripping the huge bulge inside his pants. Sarah "oohed" at how large it looked and couldn't wait to unleash "that manly thing" from its confining trousers. She licked her finger and ran it along her wet slit, shuddering as the tip of her finger met her swollen clit. All Sarah could think was, "I need his cock in me right now!"
Scott proceeded to unbuckle his pants and release his throbbing manhood from the confines of his Calvin Kleins. His thick, nine inches had never been more erect, resembling a rocket ready for launching with Sarah's cunt as the intended landing pad. He moaned as he gave his shaft a couple of strong strokes, followed by a few lighter tugs feeling his shaft swollen with his semen. He playfully wagged his prick up and down for her to take in the fullness of its size.
Sarah slid a finger into her now very wet pussy as she watched Scott play with his big cock. She moaned and rubbed her clitoris for a moment or two.
Then she remembered the condom, blurting out to Scott, "Hold on a moment!"
Sarah spun around and went over to nightstand as her lovely behind swayed up and down. She grabbed the package of condoms, removed the XL condom wondering, "How many penises did my mom sheath with these things back-in-her-day?" Surprisingly, the thought of her mom wrapping a big dick in latex so she could insert it in her young pussy, turned her on even more.
It was now Sarah's turn to "follow in mom's footsteps" and do some wrapping of her own to avoid any possibility of Scott impregnating her. She needed a hard cock, not another baby, from getting her pussy fucked. She said a silent prayer that the condom would do its job well tonight.
She turned around and headed back toward Scott. As she came close to him, he motioned for her to set the condom aside so she could suck his cock. His big prick was already twitching with anticipation of disappearing into her pretty mouth.
Sarah smiled, dropped to her knees, and set the condom on the floor, then took Scott's huge cock in her fingertips, bending it from side-to-side, giving it the once over to get present to how big this thing really was, so much bigger than her Ex's relatively small penis. She concluded that Scott compared favorably to those well-hung men she'd seen in the porn videos. Without realizing it, her finger had automatically found its way to her pussy, and she was fingering herself.
Sarah decided to stroke his big cock for a bit to heighten his pleasure before putting it in her mouth. She liked how much Scott seemed to enjoy her hands' efforts as she skillfully worked them up and down his shaft. Finally, Sarah took the tip of his cock into her mouth and sucked it as she looked up at Scott for his approval. She then swirled her tongue around his head while looking up at him with her eyes for pure visual effect, just like all the girls in porn did. That little trick worked for her, just like it did for them as Scott closed his eyes and groaned in approval.
Sarah returned back to sucking his thick head and then gradually worked her way down his shaft. She tried deep throating him but gagged about halfway down. She realized she needed more practice before she could go further down on a man this size, and even more practice before reaching all the way down to his balls. Sarah figured she'd get plenty of practice the next few days, the thought of which made her smile.
Scott closed his eyes and moaned again, "Oh, fuck yes, baby!" He was getting pleasurably lost in all her cock sucking and it made her feel really good that he liked it so much!
Sarah then switched to sliding her tongue up and down his shaft like she'd seen also seen the girls do in the porn videos. She'd been watching porn since the divorce and masturbating to it with her vibrator. At first, she felt guilty using porn—good Christian girl and all that_but eventually got into watching the sexy girls do what she wanted to try really badly. She watched in amazement when they took it up their asses; and surprisingly to her, she really wanted to give it a try. The look of momentary pain on the girl's faces before it turned into pleasure, made Sarah wet just watching.
It made Sarah think, "Would I really allow a man with a large cock to fuck me in the ass like that if I was given the chance?" She wasn't sure, but it would sure be fun to see what she would do in real life if given an opportunity. It looked like tonight might be that opportunity!
Sarah eventually worked her way down to Scott's swollen ball sack and licked it all over, popping each ball in her mouth one at a time, then continued sucking hard as Scott moaned with pleasure. He groaned as he looked down seeing his huge penis bobbing over Sarah's face and forehead as she diligently mouthed his sack. She surprised Scott by licking his anus for a bit while still gently stroking his cock. It all felt really, really good to him.
Sarah now felt like a complete whore, but surprisingly, she was absolutely loving it. This is just what she needed for her confidence, making a man so hot for her that he didn't know what he was doing. Judging by the constant twitching of Scott's cock and his moans, she was doing just that with her mouth work. She was really proud of herself!
As Sarah completed her first round of fellatio, Scott raised her up to her feet and pulled her close to his body and gave her a big kiss on the lips. Sarah melted into the proceeding tongue-on-tongue action while gently squeezing his cock with the palm of her hand.
She thought, "Time to put this thing inside me, stud!"
Scott led Sarah over to the edge of the bed, gave her a playful swat on the ass, and then laid her down spreading her legs. He paused momentarily to gaze at her beautiful blonde bush and glistening lips. His cock bobbed up and down in appreciation as if to say, "Time to get inside her, big boy!"
But first, his fingers and tongue had some work to do to get her ready to be fucked hard by his dick. Scott bent down and slowly ran his finger along Sarah's slick slit caressing her labia with the tip of his fingers; then sliding up to her clit, circling it gently until she closed her eyes and moaned heavily.
After fingering her close to the point of orgasm, he backed his two fingers out of her vagina so he could get down on his knees and eat her swollen pussy. Inserting his tongue in between her pink labia, he skillfully worked the entire vagina from top to bottom. Sarah groaned her approval.
Finally, unable to control herself anymore, Sarah came with a shriek. Her pelvis and hips bucked up and down as she convulsed with wave after wave of orgasmic pleasure. She let out a huge moan as her ass bounced up and down on the bed and at the same time she grabbed the back of his head, pushing his face in hard against her swollen slit.
During all the attention given to Sarah's beautiful cunt, Scott had been keeping his dick fully erect with occasional strokes to his thick shaft. He thought to himself, "Can't wait to get this cock of mine deep inside my beautiful new slut!" He stopped just short of blowing his entire load right then and there as he thought about how he was turning this good Christian woman into a cock whore.
As Scott brought his cock up to Sarah's slit for its grand entry, Sarah remembered the Trojan and shouted, "Oh wait! Condom! It's over there on the floor. Please get it."
Scott grinned as he thought, "Okay this time baby, but in the future, and there should be plenty of future the rest of this week, you're riding my rod bareback, no 'saddle' from now on, girlfriend!"
Scott retrieved the condom and handed it to Sarah. "Sheath me, baby!" Sarah took the Trojan XL, playfully stretched it out, and giggled as she let it snap back to its original just out of the packet size. She then stretched the condom back out and wrapped his bone quickly and expertly making him think, "She's done this before." It made him even harder thinking about the possibility of her sheathing other men in her past.
After she had gotten his condom on snugly, Scott spread Sarah wide and laid his now encased schlong squarely along the entirety of her swollen slit. He teased her pussy a little by slapping his cock against her lips, then gently glided it in her, stopping about halfway down his shaft as Sarah's eye's widened at the feeling of his girth stretching her. She moaned as he began his rhythmic back-and-forth fucking motion with his thick shaft filling her cunt to the full.
Scott had learned with the many girls over the years he'd fucked, that with a cock as big as his, he needed to take it slowly instead of just inserting and pounding away. He let Sarah adjust to the full feeling of his penis as he gently reached her cervix, his cockhead tapping against it. As her moans picked up, Scott gradually upped his speed until his cock was hammering Sarah's cunt as his big balls slapped against her pussy lips. Her body heaved lustfully with each ramming as she lost herself to his powerful, dominating thrusts.
After a good ten minutes fucking her in missionary, and now that she was getting used to being dominated, Scott turned her over and repositioned her into doggy position. He paused briefly to admire the beauty of her slit and perky rosebud. Pushing her face gently down into the mattress and raising her tight ass high in the air, Scott made his rear entry into her cunt. She was so wet that he just slid straight in, no resistance whatsoever, until his balls rested flat against her pussy lips. Sarah groaned with delight.
He then proceeded to pound her slit ferociously as her hanging tits swung rhythmically back-and-forth in perfect timing with his thrusting cock. He reached around front and gave both of them a good squeeze now and then, letting her know he hadn't forgotten about her titties. He added the occasional slap to her pretty round butt cheeks, making her yelp with even further with delight.
Scott then pulled out of Sarah's pussy and did something she wasn't at all expecting. He had a tube of lube, Sarah wasn't sure where it had come from, and he generously applied the liquid to her tightest hole, her beautiful rosebud.
Sarah thought, "Okay now, where's this going to go?"
Next, he gently worked a finger in her tight anus, then inserted his thumb along with the finger. Sarah moaned as he slowly worked his thumb deeper into her butthole. She grimaced with her first feelings of anal pain as Scott's finger joined his thumb inside her tight anus, however the pain quickly gave way to feelings of pleasure, just like she'd seen happen to the girls in the porn videos.
"I don't think I'm quite ready for your cock in there yet, Scott!" Sarah pleaded as more pain hit her as his thumb and finger probed deeper. "I've never done anal before!"
"Don't worry, baby, consider this butt training 101. I'm going to lube this butt plug up for you and gently work it into your ass so you can be used to having something up in there. Then I'm going to fuck your pussy while you're plugged up, okay?"
"Okay, whatever you say," grimaced Sarah, not sure what having something in her anus and a cock in her pussy simultaneously would be like, but she was game to try.
Sarah realized Scott had planned all this "butt fun," because besides the lube, he'd already had the butt plug ready to stick in her ass. She groaned heavily as he gently slid the lubed plug in, going all the way until just the base was visible in her anus. Scott admired the look of her beautiful, plugged up ass, then positioned his cock to re-enter her still soaking wet pussy. Scott slid into her cunt and began slowly fucking her again letting Sarah get used to having both of her holes filled at the same time.
As Scott fucked Sarah from behind, the fapping sound of her wet cunt grew louder and louder until it was the dominating sound in the room, even louder than her moans and groans. Sarah bit her lip to maintain a tiny semblance of control as Scott's big cock rocked her world all over again.
She thought, "This is even better than I thought it would be. I feel so taken by this man!" Sarah jokingly wondered if she'd even be able to walk afterwards but she didn't really care because it all felt so good to get banged good and hard with her butt plugged up.
The doggy show went on for a solid ten minutes until Scott was ready to cum. The room now smelled of Sarah's womanly pussy juices. He pulled out of her, spun her around and commanded her to, "Take the latex off me, baby!" He then reached behind Sarah's head and pulled her mouth down to his cock head and growled two words, "Suck it!"
Sarah gobbled his cock up and sucked it furiously as a monstrous orgasm engulfed Scott. He came like never before, pulsing ribbon after ribbon of semen until he completely coated Sarah's mouth. She gurgled as it filled up with a large amount of cum. She looked up at Scott with most of the big load still on top of her tongue, then smiled with her eyes, and swallowed it all. He then bent over and kissed her mouth with the cum residue still in it.
Afterwards, they both laid down next to each other and held one another tightly, kissing over and over. As they kissed, Sarah gently stroked Scott's flaccid manhood back to erection.
"Look, baby, you did so well, my rod is saluting you ready to go at it all over again!" With that, Sarah leaned down and started sucking his big schlong once more. Scott closed his eyes and readied himself for round two. Sarah smiled to herself as she sucked his now stiff boner, thinking, "Thanks mom for the condoms, but I think I'm done with them for now. I want his huge manhood in all my holes au natural from now on!"
