Chapter 6: Beach House

Jasmine

Will is a perfect gentleman, easygoing, easy to talk to, and very easy on the eyes. My evening was very well worth it. What an honor to spend time with such a polite young man who knows how to please a lady.

What a rare treat to find such a young stallion who is very well-mannered and mature. And ladies, his attributes are delightful. Sample his ‘offerings’ to your heart’s content, he does not disappoint! I’ll be requesting more from him soon!

Hey, bitches, this kid can fuck!

Seasoned ladies, how often have we wished to bed an eager young stud, but one with patience and maturity? Will is all your expectations and more. What a wonderful way to unwind after a busy day on the convention floor. Having Will made me feel like a giddy teenager exploring the joys of sex.

Will is outstanding, I thoroughly enjoyed him. He’s a very sweet guy – Literally! Hey, Will, our lunch was fantastic, I’d love to eat [with] you again sometime!

It’s about damn time! LOL! Thank you SW Swim Club for finally offering an option for us traveling businesswomen, the road gets lonely. Seriously, you have a great escort in Will. If I could, I would pack him into my travel bag to take with me from city to city! Can’t wait to get back to Grand Rapids. P.S. Do you travel? I’ll be in Chicago in a month and Detroit in two!

The subject of such glowing praise is standing in front of me with one foot lifted on the couch armrest and his pelvis pushed in my face. His fluffy patch of pubic hair is dominating my field of view, it’s all I can see. His soft blond curly hairs envelop my nose and tickle the insides of my nostrils. This is the perfect way to enjoy his body’s most private scents in his most private places; he’s very appealing, I would dare say exquisite!

My mouth is stuffed full, stuffed full of what defines him as male. For being so sexually excited right now, I must exercise a practiced mental calm that allows my esophagus to relax and accept his glans even deeper. I want every millimeter of this young man’s cock; I want to savor it as well as please it. Anything pushed past a certain limit will trigger my built-in anti-choke defense mechanism of gagging. I’ve honed my skills to bypass that reflex so I can perform this effectively.

With him pushed in my gullet and his tight balls pressed to my chin, I feel his body quiver and hear his moans of unmistakable pleasure. The super smooth surfaces inside my throat welcoming his sex will always be a special treat – for him, and me! Long ago I learned that the act of swallowing creates an undulating, gripping, releasing, and caressing that stimulates a man’s most sensitive spots from his tip, inside the surrounding indent, and below with an unparalleled uniqueness. Couple that with my lips tightly wrapped around his base and feeling my tongue licking, lashing, flicking, and dancing along his shaft - it’s a wonder any guy can last more than a few short minutes.

Not forgetting that I need to breathe, I can only host him so deep like this for short periods of time. Periodically I must pull back, let my throat relax, and release its grasp to inhale. This action of slipping back, then re-welcoming him has the bonus of even more stimulation; a win-win for both of us.

It’s never a question that pussies will always feel great for a man to sink himself into, but a mouth has so many working facets that act independently and in unison to pleasure a penis like nothing else. Pleasing him this way is a pleasure for me as well; I’m the one in control of metering his euphoria. Not that I wish to torment and tease (well, maybe tease a little bit), but giving great oral sex is very empowering in its own way.

For as much control as I have in my life, including me being such a cougar right now greedily sucking my newest employee’s cock, I also want him to feel he’s in control as well. I like how he holds my head to his pubis while whispering naughty musings of, “Ohh-yeeahh, feels so good. You really like sucking that, don’t you?” And, for the record - Yes, I really do like sucking you, Will!

In professional circles, I’m a highly respected business-savvy woman, even feared by some. What a hoot if they could see me right now with my face smothered in the sweaty groin of an eighteen-year-old who’s using my mouth to satisfy his primal lusts.

Many mouths have been enjoying Will’s cock, and for good reason, he has a great cock to suck! Not only is it attractive, but it’s the perfect shape and size.

Above me, he moans, “Get ready, I think I’m gonna cum ... like, really quick here.”

You think? I already knew this well before his vocalization by his fidgeting and twitching. Like a lot of guys, he has bouts of vertigo when ejaculating while standing up so the last thing I want is for him to lose balance at his crucial moment - his giving moment of deliverance. I tightly grip his ass cheeks to hold him steady. I love his ass, such firm round twin globes. I can see why Daisy likes to give him special kisses on his rosebud in between; I may need to do so as well.

Letting him shoot straight down my throat would be one thing, but I want a good taste of him. Pulling back a bit, I position his pee slit directly on my tongue. Just in time too, it’s happening!

With a telltale grunt, his shaft swells fat for a fraction of a second before my taste buds are awash in a powerful jet of his plentiful essence. Before the velocity of the initial stream diminishes, the next volley explodes, spraying more of his warm and creamy to coat an additional thick topping over the first. Over, and over, and over, this happens. My god, this kid, his ridiculous release is comparable to that of a herd of raging bulls stampeding down a narrow corridor! It’s not just my tongue, but the interior of my mouth is now immersed in the stuff. His delicious cum quickly fills all available spaces; I would dare guess he’s spurting at least a dozen times! Healthy-sized spurts too! That’s okay, give it to me boy, give me all of it!

After that day in my office when I first sampled how truly delectable he is, I’ve been craving more. I was growing so perturbed with each passing day that our schedules didn’t match up. Finally, we now have a couple of days off together. Listen to me, I sound like a silly schoolgirl amid a puppy-love crush!

Climax subsiding, he collapses on the couch to regain his senses. As I’ve mentioned, he’s been receiving a lot of blowjobs lately, but if there’s one steadfast fact of life, no man, young or old, will ever grow tired of having his cock sucked.

Legs apart with one foot up on the cushions and the other on the floor, Will is beautifully showing off everything, specially that amazingly still erect cock - what a wonderful and erotic display. It’s like he’s the subject of a naughty Norman Rockwell painting that could be titled Naked Young Man Enjoying Post-Ejaculation Bliss.

Rather proud of how spent and satisfied he is because I just blew his mind by way of his pussy-pleaser, I grab my camera to snap a few impromptu pics of him splayed out like this. Assuring him that they’re for my private collection, I take several at various angles including some nice zoomed-in close ups. He has fun posing with a big goofy grin, grabbing his pecker, and giving me a big thumbs-up. Next, he makes a spectacle of rubbing his balls and spreading his ass cheeks - he’s such a clown, and a great sport at the same time.

The couch is large, so I edge him inward to lie next to him and play with his tool. Feeling his hot meat throbbing in my hand, something tells me it won’t take long for him to recharge and be ready for more.

“Jasmine, that felt so good! Wow! Talk about beyond awesome! Thank you!” he gushes letting his own hands roam, they quickly find my nipples to pinch, and boobs to caress.

“My pleasure. I fancy myself a fellatio expert ... if you haven’t noticed.”

“Oh, I noticed! You and Daisy are both incomparable.”

“Really?” I act startled. “So, who’s better at it, her or me?”

“You just had to ask that, didn’t you?” he laughs. “Honestly, you’re both fantastic and I don’t think there’s any way I could pick one ... without getting myself in trouble, that is.”

“Smart kid,” I snicker and pinch his balls. “Best answer for staying in our good graces. Kudos to you!”.

“Well, not only you and Daisy, but my cock would also kill me if I fucked that up,” he smirks.

“You’re probably right about that!”

We’re at my beach house on Lake Michigan just north of Benton Harbor. It’s a beautiful September day, all the windows are open wide to the gentle breezes and sounds of the surf hitting the sand, what a sweet and relaxing ambiance. Will told me that he was here once before when I let a work associate of my sister use the place for a group sex party; he was part of that group. “Well now,” I say, “I can only imagine what an impression such a party made on you being so fresh and sexually inexperienced.”

“Well, I wasn’t that inexperienced, I had sex two times before that.”

“Two times!” I playfully tease. “A true master of all things carnal.”

“No, I just meant that I wasn’t a virgin.”

“I know, Will,” I squeeze his shaft, “I’m just playing with you. In all seriousness, look at how far you’ve come in these last couple of months compared to who you were.”

“Yeah, putting it that way, you’re right.”

“So, how are you liking this line of work? And be honest, there’s nothing you can say to offend me.”

“I’m liking it, I really am. I always knew sex was popular, but I never imagined it was such a huge part of so many people’s lives.”

“And that’s exactly why this business thrives.”

“You aren’t kidding about that...”

“I’ve noticed you’re getting a few requests from men. How do you feel about that?”

“Well,” he chuckle-laughs. “I’m okay with it, but it definitely takes getting used to. I hope this doesn’t sound one-sided or selfish, but if a dude wants to suck me, fine, I just can’t bring myself to reciprocate the favor.”

“And that’s perfectly okay. Believe it or not, it’s not uncommon. There’s a fair amount of gay and bi men wanting to suck a straight guy, especially a hot younger straight guy, and not expecting, or even wanting, a return. A gay friend once told me that having a straight guy is considered a real treat like the sweetest of desserts, along with earning a badge of honor. I don’t fully understand it all, but it is what it is,” I shrug. “Look at it this way, it’s a nifty option that’s mega-easy on your part.”

“Yeah, it is! I just sit back and spread my legs. Speaking of which, I had this exact scenario just a few days ago. The guy sucked the hell out of it, made me cum, he was happy, it felt good, my nuts were empty, and that was that. I spent more time driving to and from the hotel than I did with my pants off,” he laughs. “I was thinking that maybe we should make a check-off option for these clients on my menu called Sausage and White Gravy Lunch or something.”

“Sure!” I laugh with him, “I can have my tech guy add that if you want.” White gravy, not just gravy, or hot gravy, but specifically white gravy, that’s my silly Will.

“Cool!” Then in a goofy voice, he mimics a fictitious customer like he’s in a diner. “Pardon me, but I’ll take the Sausage and White Gravy Lunch Special please.” In many ways, Will is an old soul with a calm demeanor and maturity, but I like it when he shows his youthful side too. It lets me know he’s relaxed and being himself; another quality that makes him so attractive in his own special way.

“Do any of the guys ever get pushy, or ask for more?”

“No, they’ve all been really nice. I did have one that wanted to check out my ass.”

“But I thought you didn’t do anal?”

“I don’t. He just wanted to kiss and lick my asshole; I was fine with it. Should I not be letting clients do that?”

“No, it’s fine. If you’re okay with the fun, then all’s well. But remember, Anal Play is technically an extra they should be paying for.”

“Gotcha.”

“Are there any aspects you find more difficult than others?”

He thinks for a moment, then says, “Keeping my ego in check. Three months ago, girls barely knew I existed ... and, yeah, I know part of it is my fault for being so introverted. But going from my only sexual activity being jacking off and self-sucking to now having all kinds of—”

“Wait, what?” I interrupt him. “Did you just say self-sucking?”

“Yeah,” he grins, “it’s kind of a hidden talent I have.”

“Really! I’m intrigued. I would love to see you do that.”

“Okay, but how about later? I’m still recovering from...” he waves his hand over his parts, “ ... you know.”

“Absolutely! I’ve heard about guys that can do that, even watched videos online, but I’ve never actually seen it for real.” This kid is full of surprises - fun surprises as I’m continually discovering. “Anyhow, go on with what you were saying.”

“For me, going from a nonexistent sex life to now having all kinds of people wanting to touch me, suck me, and have me fuck them is surreal. I feel like an overnight mega-rockstar or something. Daisy and you both warned me about not letting it go to my head and I completely understand that, but, damn, it’s harder than I thought. It’s like I’m walking around with a magically charmed penis in my pants that suddenly everyone wants.”

“And, that’s exactly how it is for escorts,” I concur. “For the girls, it’s their charmed pussies, asses, and boobs. This profession definitely has its own unique traits; once you put yourself out there in this manner, it seems like everyone wants you. So, yes, your ego must be kept in constant check. I’m not saying don’t enjoy the special attention, but always stay professional about what you do.” With that, I give him another squeeze. He’s still rock-solid if you can believe it! I’m sure my hand never letting go has something to do with it. “Trust me, Will, you’re on the right track and have nothing to worry about. Just the fact that you’re aware of potential ego issues tells me you’re being smart about it.”

“Thanks,” he grins, “but please tell me if I ever start getting a fat head and going off the rails.”

“No worries, that’s my job.”

In the real world, a forty-some-year-old superior having her newest, and much younger, employee at her house alone would no doubt be a strong case for raised eyebrows. And this is not even taking into consideration that we’re naked and what I just swallowed! The good thing is my other employees won’t be jealous because I’ve done these same things with every one of them, and will continue to do so. I deeply love all my girls, and now my one guy.

This service we provide thrives in its own reality and flies completely under the radar of what’s deemed normal, or conventional in the real world. Not to mention moral. My company provides companionship specializing in sexual interaction and satisfaction - for a price, of course. Being chief executive of such a business means I must ensure the services we offer are everything we advertise; in other words, I make it my duty to sample our product. You could say I’m not only the CEO, but also the head of Quality Control.

Maintaining this type of employer/employee relationship like no other company would dare definitely has its rewards and benefits. I make it a point to have every one of my escorts come here and have the time of their lives because they more than earn it. This beach house may be in my name but it’s for all of us, we built this. Every morning I’m amazed at this crazy life I find myself in, but I wouldn’t trade a second of it for anything.

Am I nothing more than a high-class pimp disguised as a professional businesswoman? In some people’s eyes, perhaps, but we operate at a professional level of discretion well above such a street-thug mark. Our escorts are qualified, healthy, clean of STDs, drug-free, and hold no criminal records. It happens that we live in a time and location where the world’s oldest profession is deemed illegal; I am not here to debate morality and laws, just do my best to quietly skirt around them without detection.

How does the old line go? Loose lips sink ships. Every day we run the risk of a client or an escort saying the wrong thing to the wrong person. As touchy as this sounds, it’s not as bad as one would think. We have many state and federal-level law-making politicians in our customer base, thus making them benefactors of the club. Needless to say, remaining discreet is in their best interest as well. See how well all things work together?

“Would you like me to eat your pussy?”

Ah, yes, such sweet music to my ears; what a perfect segue to break from my narrative. “Absolutely, Will. How would you like me? Over your face, laid out on the bed, or I could bring over one of the tall chairs from the breakfast nook bar?”

“I like the chair idea.”

Setting it up so it’s facing the couch works perfectly to sit while conveniently putting my pussy at face-level for him on the couch. I’ve used this technique before and found that it works very well. I like how the back of the chair is strong enough for me to push against it while jutting my crotch outward. The armrests are great to hook my legs over leaving my feet dangling on each side for a nice wide open and inviting spread.

For being in my mid-forties, I’ve taken good care of myself and work hard at keeping in shape. My legs are long, my ass is tight, my belly flat, pussy waxed, and my tits are still perky – for the most part. They aren’t quite as firm as when I was eighteen, but that’s to be expected. Without meaning to sound full of myself, I could give any mid-twenties or early-thirties chickee-poo a good run for their money in the body department. I’m also a big fan of maintaining a nice tan; this large property allows enough outdoor privacy for many hours of carefree nude sunbathing – no tan lines.

Still faintly tasting Will’s semen on my breath has my excited pussy absolutely soaked. His timing could not be more perfect; I’m so craving his face between my thighs with his mouth and tongue massaging my mound. In position, Will is licking his lips studying my flower. Reaching down, I part my labia to give him a peek inside my succulent inner folds. His eyes grow wide and his hand drops between his legs to stroke his hard cock.

“Hey, don’t be shooting that thing off, I want that cum in my pussy or in my mouth.”

“But I just gave you a great big load,” he snickers.

“Yes, you did! And you’re going to give me plenty more, now get in there, and let’s see what you can do.”

The buildup, the anticipation is such an important ingredient of stellar sex. Will is honing his skills and becoming a true master at this. He moves in closer, not touching, but allowing his hot breath to gently breeze across my wet lips. It’s contact, but not contact at the same time - it’s driving me crazy! I’m pushing my pussy at him, trying to force a physical connection but he’s staying just far enough away to deny me. If I push out farther, I’ll slip off this damn chair and fall in his lap. Hmmm. If I do fall in his lap, my pussy will impale itself on that erection he keeps stroking – maybe it wouldn’t be such a bad thing after all.

Making eye contact, he sticks out his tongue, wiggles it and waits – and waits. Now, this motherfucker is just taunting me! I’m so gonna—

GASP!

As fast as lightning the tip of his tongue darts in to lap my supercharged pussy. I swear the very air just buzz-zapped with crackles from the sexual energy sparking like an exposed power line. My muscles instantly tense as a sudden jolt of overjoy rips through my body. Dammit, Will! You’re too good at this!

He starts off slow by tenderly licking my slit from the bottom up to the top, and everyone knows how special the top is, it’s where my hooded little nub is. At my clit, his lips slide over like he’s seductively suckling on a pencil eraser. I can feel a slight tugging as he’s pulling it into his mouth to gently drag his teeth over. Oh, gawd, this feels so good!

I have a quandary and it’s that I only have two hands when I need four. My fingers are spreading myself open so he can feast on everything. But I desperately need two additional hands to place on his head and hold him to me. Like he did with me earlier when our roles were reversed, it’s such a form of lovingly communicating how ecstatic I am over what he’s doing. This is an easy fix as I tell him, “Will, spread me open.” Without missing a beat, he maneuvers his fingers to join the action happening in my pussy.

Ah, this is better, now I can comb my fingers through his beautiful thick dark blond hair and massage his scalp. He has such nice hair; I like how it’s a little on the longish side and matches his summer boy appeal.

Scalp massaging soon leads to holding his head to me. Keeping him secure between my spread thighs with his face pressed to my wet and wanting womanhood seems like such a sexually nurturing gesture (if there is such a thing); all I know is it feels good and warms my very being. Or it’s just that I’m all done with his teasing, and he needs to keep pleasing. Unconsciously I moan, “Lick my pussy ... ohh, that feels so good ... Eat me...”

Earlier I compared how men will always love to put themselves into pussies, whereas mouths offer unique and different forms of stimulation. The same can be said for a woman. It will always feel good to have a man push his cock up in me, but, damn, Will is executing so many alternating stimuli right now, my conscious pussy doesn’t know where to focus – and that’s a good problem to have!

His open mouth is covering my mound while his tongue is strumming on everything from my clit to my urethra, and down into my slippery hole. His jaw is working up and down and left and right to further jostle my vulva creating additional levels of beautiful euphoria. Feeling his lips, tongue, and mouth working is igniting an explosion of mental jubilation that’s blooming and overlapping bright colorful displays in my mind’s eye. And this kid is only eighteen? I can only marvel at what he did in a former life to know his way around a vagina with the expertise he’s exhibiting.

It’s been described that an approaching orgasm is like a rising tide, each wave hitting the beach reaching farther up than the one before. Eventually, a wave will not only hit but wash over and trigger every pleasure synapse. But that’s not the end of it, the next wave will further immerse setting off even more synapses that you weren’t aware of!

“OH! OH! OH! Ohhh!” I shout out as my calves clamp inward on the chair’s armrests - god, I hope it doesn’t break! At the same time, my pelvis pushes outward as my hands smash my young lothario’s face against my orgasming and squirting pussy. I can feel myself making a ridiculous slippery wet mess of Will’s face and the seat cushion below, but this is also amazing because I haven’t squirted this heavy in a long time. Maybe it’s because I’ve been so anxious to have him here, anxious to have his cock, anxious to have him licking my pussy, and this is my big lascivious release. Maybe it was his annoying but perfectly timed anticipation buildup, probably all these things rolled into one fantastic sexual planetary lineup that I’ve been needing for one fuck-of-a long time.

He’s giving me that big goofy grin of his again, this time his face is glazed, covered in my juices from that sloppy climax.

“Oh, I am so sorry, I can’t believe I did that. Normally I don’t squirt much at all, but—”

He puts a finger to my lips. “It’s okay, I actually love when a woman does that.”

“You do?”

“Sure! If I can make a big mess when I cum, a woman should be able to as well. Plus, it’s a sweet bonus for me.”

“If you say so, kid. I gotta hand it to you, I love your spirit.”

Will and I rinse off in the shower before fixing ourselves some big fruity summer drinks. It’s time to go outside and sit on the deck to bask in the late summer sunshine. In a few weeks, it’ll become too cold to do this naked.

Don’t get me wrong, I absolutely adore all my girls and love having them here; I especially lust for their sexy naked bodies, but something about seeing Will freely walking around nude really gets my juices flowing. Freshly rinsed off, and here I am with my pussy all wet and slick again.

I’m starting to wonder why I waited so long to bring a hot young guy like him into the club. Ah, well, better now than never, and no sense in berating myself over it. As for Will, he’ll always be special, the first male sex machine I turned loose on the horny women of the world – well, of southwest Michigan and the surrounding areas to be specific.

Getting ready to lounge in the sun, I notice Will’s farmer’s tan, but it’s not the typical farmer’s tan of having a pale chest and shoulders, his whiter skin is all of his private areas normally covered by a swimsuit. Lord knows I wouldn’t want him to get any kind of uncomfortable sunburn on those parts, especially his money maker.

“Make sure you slather plenty of the highest SPF sunscreen on your body that isn’t used to being out in the sun.”

“Yeah, I will.”

“Or, better yet, let me help you with that,” I flash a sly grin. Another chance to have my hands all over him works for me!

“Sure!” he moves to stand in front of me. Like Pavlovian Conditioning, his dangler presented inches from my face brings out the strongest urge to lean forward and stuff it into my wanting mouth. I mean why not? I could easily push my face to his body and indulge on a quick little suck. Who am I kidding, for me, there’s no such thing as a quick little suck, I’d better wait until later. With his frontside is all lotioned up, he now has a nice precum-leaking hard-on from all my massaging. Waste not, want not, I carefully save those precious drops of his clear slippery sweet stuff with my fingertip to slip into my mouth – mmmm!

Turning him around to rub each of his ass cheeks, I playfully smack them to watch their tight jiggle while working the sunscreen into his tender pale skin. My lotion-lubed fingers easily slide into his warm space in between to explore the length of his crack from top to bottom several times. At his puckered opening, I tickle to feel it contract and respond before slowly easing my index finger inside.

He turns, looks back, and grins, “Isn’t that supposed to be my place where the sun never shines? You know how people say, stick it where the sun doesn’t shine. Do you really think I’ll get a sunburn in there?”

“Smartass!” I push all the way in to the last knuckle. “You can never be too sure, so it’s best to take every precaution,” I laugh, working my finger in and out. His hole is hot, smooth, and tight. Flexing his sphincter, it’s extremely strong as it firmly grips and releases; my unexpected intrusion must feel good to him. While I’m in deep, I’m tempted to tickle his prostate, but that can be a surefire ejaculation trigger and I don’t want to waste his cum by making him shoot it out here on the deck.

Once Will is completely UV-protected inside and out, I lay out to have him lather me up as well. Even though I have one hell of a great base tan and am not too worried about sunburn, I still want his hands rubbing lotion and roaming every inch of my body, including where sunlight rarely reaches. Will takes care of this with very arousing expertise, not just poking and jamming his fingers into my orifices. He warms me up in my special places by centering attention first on the surrounding areas of my boobs, nipples, clit, and pussy before zeroing in on my pleasure buttons; he has such a wonderful sense of patience.

When the front side is done, he has me turn over to take care of my backside. Working from my neck and shoulders all the way down to my ankles, he doubles back to finish the job by tickling and wiggling his finger deep inside my anus - I could get used to suntan lotion being applied like this!

As his hands work my body, I have a good laugh when he tells me some of his random thoughts. I especially like the one about his cum jetting off to new and interesting destinations around the world in the bellies and pussies of his many dates at the Banking and Financial Investments (BFI) Convention a couple of weeks ago. This kid’s naughty mind works a lot like mine in many ways.

There’s something I’ve been wanting to ask if he’ll share. It’s about Vicky and how things went with her; that date had a profoundly positive effect on my friend. Her grouchy grumpy self seems to have vanished, literally evaporating into thin air. She even asked when I’ll take her for that makeover I’ve been begging to do for her for the last ten years. Will did say he feels like he’s walking around with an enchanted penis in his pants, he may very well be onto something.