Genie's Wish Ch. 03

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All Jack's seduction skills tempt unsure girl to try anal.
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Part 4 of the 5 part series

Updated 12/28/2022
Created 11/23/2022
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Twenty on the outside, fifty on the inside, Jack had his clock rolled back by a genie. Follow along: Jack puts his seductive powers to the test, persuading an uncertain nineteen-year-old college student to try anal and more for the first time.

I use the expression "woman-child" in this story to indicate a very young woman, but all acts depicted involve legal-age, over-18, consenting individuals.

There is female-on-male ass-play in this story. If this is not your cup of tea, don't pretend you weren't warned.

TAGS: Seduction, anal play, anal sex, younger woman, older man (sort of), coed, oral sex, curvy, toys, fingering, voyeurism

Nine Chapters:
Tris
Six Hours Earlier
The Midnight Hour
Act One
Act Two
Dawn
Act Three
Nap Time
Happy Hour

TRIS

"If it's supposed to be so good, let's see you do it!"

The voluptuous, corn-fed girl's hazel eyes challenged me. Boy, did those go nicely with her glossy-dyed, wine-red double French-braided pigtails. We lay together nude, in between a round of mutual oral 69 position and whatever was to follow. Some kind of intercourse, I had no doubt at all.

Would it get as far as anal? I was damn well going to try. I had never before applied myself to convincing young hotties to try any major kinks. I wasn't even super into anal, myself. Nor do I consider it particularly kinky. But the challenge was a thrill. I knew that Tris's experience so far strictly extended to the vanilla and no further. Yet.

I wasn't in any pressing rush, though. I had been asking Tris about her sex life. I mean, I had only been part of the picture for less than a day, here. What did I know? Plus, she sort of started it.

I only appear about a year, two at most, older than her, in physical appearance at least. But there was no disguising the maturity behind my manner, confidence and sexual patience and skill. Nobody in their right mind would suspect me of having lost my virginity more than three decades earlier, but something was clearly going on with me which college-age boys weren't supposed to have. Tris was trying to get to the bottom of how I had rocked her world so hard.

The truth at best wouldn't be believable, given the way I look. At worst, I might be taken for a dirty old man, working a subterfuge, behind a pretense. I mean, that isn't wrong, I'll admit it, but... It's complicated? Soon, I would have new ID's to prove my calendar age, if necessary,* but even then, I can't go around telling people I was born in the early 1970s without a damn good reason.

* See Genie's Wish Ch. 01.

Anyway, what I was doing instead was putting on an act of putting on an act. I wanted her not sure whether to believe me or not. Yes, I was trotting out stories for her about sexual experiences which seemed a little far-fetched for a guy apparently not even of drinking age.

Well, hell, maybe not - we are well into the 21st century. Kids these days were raised on the Internet. Naturally they'd have seen porn of, and fantasized about, things I never even heard of and weren't even legal in some states ('Murica!) when I was well into my twenties the first time around. For all I knew, lots of young people were acting them out, too, before they even left the nest.

Wild times we live in.

I didn't think Tris had done so, though, and what I was finding out was confirming my hunches. She really seemed wholesome. Squeaky clean, literally farm raised, away from her God-fearing home for the first time in her life, a college sophomore. Boyfriends here and there, but no long-term relationships. Her burbly personality was uncontrived and genuine. She had been bold enough to make the first move and hit on me, apparently un-hung-up about things like that. She seemed to still be trying on her big-girl pants as far as partnered sex went. She was still using terminology like "the bases" and "going all the way" to talk about her past. How adorable! But she was eager to get down, and easily orgasmic, but wide-eyed and innocent in the acts we had shared so far.

She was perfect.

I chewed my tongue a moment, and eyed Tris sideways across my pillows.

"What if I do?" I mused thoughtfully to her.

She stared at me, not having expected me to be game for that at all. She squealed amusedly, "Ho-lee shit, Jack! That would be..." She didn't know what. I shrugged, and held my tongue.

She finally came up with, "Fucking hot."

We were in the aft double berth aboard my 42-foot sailboat, out of the water and up on jackstands in a Saint Augustine, Florida, boatyard. It was just a few days away from splashing her into the water again. What I had been calling the "skipper's cabin" was designed to be marketed as a "stateroom," though that label was a little pretentious, in my opinion. Still, many a couple had lived aboard vessels like this in berths even smaller than mine, some for years and years at a time. A six foot tall person could (luckily!) stand up on the floor without banging their head on the cabintop, but the berth itself, roughly queen sized, didn't have a lot of headroom, compared to a traditional dwelling.

I teased Tris, "If you say so!"

SIX HOURS EARLIER*

* This picks up right where Genie's Wish Ch. 02 left off.

I got myself real good all over with the soap, wanting no trace of Livia's pussy cream or my own come to be detected, even subliminally, when I went to meet Tris in two hours, when she would be closing up at the yoga studio.

I finished my shower, dried off and stepped into some boat shorts and flip-flops. switched the laundry from the coin-op washer into the dryer machine, and made my way down the path from the marina facilities to the boatyard next door, where my boat was on the hard until next week. I had projects to finish and it would be a marathon, but I had blown off this afternoon to play with Livia, the hot Latina milf who worked in the boatyard's office, and then I had been instructed to pick up the nubile and brassy Tris at the end of her shift at the yoga studio.

It occurred to me to question whether she had been sincere about warning me to leave the yoga students alone. She worked at the front desk, and I didn't think she was a practitioner. That morning, she had told me the yoga teacher whose beginner classes I was taking, Madison, would strongly disapprove of me picking up any of the other students in the class. Then Tris had let me know that she herself was available as alternative - this very same evening, in fact!

When it rains, it seems to pour, I mused, remembering the romp in the boatyard office's staff room just an hour or so ago. I was confident all evidence of it was gone. I set a timer for an hour and went aboard to nap while the newly tailored, and broken-in-with-secretions, clothes dried.

I also thought about the abundance of extremely cute women in the yoga class. I mean, that was half the reason I was there, besides my resolution to take damn good care of this youthful body while I had the miraculous gift of time. I didn't want to make it to fifty again in as poor shape as the first time around.

My brain fuzzily noodled over such things while I dozed. The yoga teacher was undressed in my mind, too. Was she really going to have a problem with her students hooking up with each other? For all I knew, Tris had stone cold made that up for her own reasons. She had seen me flirting with the blonde and bodacious Becka in the yoga studio lobby, and could very well have decided it would be herself instead of the other, enjoying my company.

I woke from a light sleep, unconcerned. If Tris were to turn out to be a manipulator of that caliber, I'd make it work out. I felt a little guilty projecting the suspicion onto her, but with this many years' experience, one sees things and learns from them. It's better to be prepared for anything than to not see things coming at all. Anyway, she really did seem genuine and guileless to me. My instincts had to count for something, right? I climbed down the ladder from the deck of my boat to the ground and went to fetch my dry shit from the laundry room.

I had bought these shirts and slacks when I had been at least fifteen pounds heavier, and the bulk in different places, before my baffling transformation.* As of about a month earlier, at this point I was now a six-foot-even, maybe buck-seventy-five strapping laddie of twenty again, dark haired, fair skinned, and sunscreening religiously under the subtropical Florida sun. One doesn't get a second second-chance, when it comes to preserving one's skin. That I had been bestowed a first second chance at all was a miracle and a mystery.

* See Genie's Wish Ch. 00.

Livia in the office had received the clothes when the tailor had dropped them off for me. This was her chance, after weeks of mild flirting on her part and coy stand-off on mine, to bait me into "modeling" the alterations for her. I was going to wash them anyway, as standard procedure, but they had gotten a bit messy on the catwalk, you might say.

Back on my boat, I changed into the tan slacks, colored a rich and saturated khaki, along with the light-blue dress shirt. I thought the Salvatore Ferragamo shoes would be a bit overkill for a date with a nineteen-year-old, so I put on my topsiders.

I reflected that besides having been a really nice, spontaneous surprise and a howling good time, the aftereffects of the recent lay with Livia were for the meantime easing the pressure of the roiling late-adolescent hormones I was enduring all over again. I've never been one to make a point of getting myself off before trying to get lucky. In my youth I barely considered the benefits, and in my later years I didn't need to.

Since I now have that experience, maturity and control under my belt, even though the belt is suddenly two notches shorter, I really still don't need to prepare for dates like that. But I imagined it would make it that much easier with Tris tonight, taking things as deliberately as she might want, and showing her a patience and stamina which she would have never known with guys her own age before.

And I was willing to bet, guys her own age were all she had known.

I turned the wrong way on my way to the yoga studio. By the time I finally got there, I was borderline late, or I would be if I looked for scarce street parking. It was a Friday night and the district was full-bore dinner-rush crowds, so I took a chance and pulled my car into one of the staff spaces in the studio's tiny, non-public staff lot alongside the old brick building.

I sat there a moment, settling myself down, wanting to appear collected and unperturbed when I rang for Tris to meet me at the door. It would have been locked from the inside since eight, and she was due to clock out and leave right about... Now. I took just a minute to catch my breath, and remember what I wanted.

Since the change, I had been moving through a series of challenges, cultivating my sexual strength and seductive craft. My first lay since the fountain of youth had showered down on me was my first with anyone at all in a long time, and my first with someone other than my ex-wife since before the divorce. I had seduced a married woman, and discovered how deadly my barely-legal looks and fitness combined with my middle-aged experience and maturity were. Convincing her to let me scratch her itch had been a royal treat and a half.*

* Genie's Wish Ch. 00

Tonight would be different, as far as casual sex went. I had no doubt whatsoever I'd be laying with Tris this night, but I wasn't coming off a demoralizing, divorce-punctuated dry spell and an earth-shattering physiological overhaul this time. I briefly reflected on the contrast with my other recent dates too.

I had struck a deal with a cosmetic doctor and her associate-slash-partner, whose business turned out to be procuring professional male company for rich plastic-surgery clients. In return for a paper trail explaining why the portraits on my replacement driver's license and passport would look so wildly different from my original ones, I had provided my services as an in-kind trade, and took ten mature ladies around the world, honing my craft and exercising my skills.*

* Genie's Wish Ch. 01

That commitment was over now and I would have my new IDs soon, mission accomplished, knock on wood. I made a mental note to ensure Tris wouldn't have occasion to ask to see, or look for herself, at the driver's license in my wallet, with some fat old guy's picture. I mean, I really hadn't been that unattractive at fifty, but I was quite sure it wasn't what Tris was signing up for, if she even were to believe that I had shed thirty years somehow.

Thinking about her freckles, curves, hazel eyes and double French braids made a bolus of testosterone or something charge my blood up. I thought it was just about time to go knock, and meet "Pigtails." I took a deep inhale and exhale to smooth out the butterflies, and gave a silent thanks to my other new fuckbuddy (not to count chickens, here, but I guess I was) who had just provided me with a pressure release.

When Livia had surprised me with sex at her work just hours earlier, the challenge to restrain my barely-adult body's hair-trigger tendencies had been ramped up exponentially. The enormous age differences, the unnaturally altered appearances, the total absence of uncertainty regarding the outcome, and my own sheer professionalism had bestowed ample powers of control on me during those gigolo dates. By contrast, my encounter with Livia was long anticipated, spontaneous, raw, and thrilling on a purely organic level. She was extremely enticing and my inhibitions had been unfettered. She had thrown herself at me and was beyond generous sexually, and I had at last completely let myself go in a way I hadn't since before my marriage, decades earlier.

What I was interested in next - tonight - was to work on seeing how far I could go with my powers of seduction. I already had extreme confidence in my ability to score. In general, but particularly with Tris. She had made the moves on me. I already knew I could go whatever distance any lady needed or cared to. And attentively, sensitively show her an extremely good time all along the way. I was sure I could steer clear of various complications and pitfalls, enhancing the carefree approach and easy manner which I find puts women's inhibitions at ease and allows their desires to blossom.

Just how much, exactly? I wondered about that, and planned to practice finding out. Of course there's no single answer, I'm not ignorant. Everybody's different. But everyone has the potential to cross lines, to dare to explore certain uncharted kinks, to take a chance at a novel shared experience, overcoming apprehension and a certain level of taboo. I sensed that enticing women to act on these dares would be a valuable skill for me to develop.

I wanted to find Tris's tentative, imagined boundaries and take her beyond them.

I got out of the car. Nobody would be pulling in, wanting the staff parking space, so I walked away from it and knocked at the front of the building. It was eight twenty two, and Tris opened up immediately. We stood there, eyeing and smiling at each other through the doorway. I waited to see what she would do, and she didn't come out. She asked me to come in "real quick" instead.

She closed the door behind me as I stepped in to the lobby. I faced her so I could see if she needed to finish some last thing up, or what, and she just stood in front of me, diminutive but curvy, cheerful and curious. "You showed up!" she chirped.

My dark eyes crinkled, and I promised, "Wouldn't miss it for anything, Tris!" Her eyelashes lowered, fluttering over her hazel eyes, half a performance, half genuinely pleased. Knowing she was doing it half-on-purpose for my sake, I watched, like she was a superstar whose tickets I had paid big money for to hear her sing my favorite songs.

The attention actually made her crack up slightly. "You're a pushover, you silly!"

I grinned good-naturedly and let my own eyes twinkle. I pitched my voice low, and breathed, "You're just cuu-uute. I love your hair, by the way."

It was a really well-done color job. Fresh, too, as there were no roots discernable beneath the deep-crimson gloss. She hadn't had the eyebrows done to match, though, and they betrayed a not-too-dark, rich brown natural color. I expected the carpet, if any, to match, and my eyes drifted down as if I could x-ray-vision a peek at it.

Of course I couldn't. Nor could I conceal my look.

"Down, boy!" Tris giggled, but she stepped forward and stood close to me. She put her hands up on the front of my shoulders, a decent reach for her below-average stature, as my own is on the tall side.

I joked, "Hey, you're blockin' the view!" But looked into her eyes.

I shouldn't call it a trick, but there's a thing I've learned to do, to help women feel seen and appreciated. I pushed everything out of my mind except for the mindful present. What was happening right here, right now. The unfiltered senses filled my awareness and I made myself with-her. I'm pretty sure my eyes were dilating as I was looking into hers, and I know that warm blood was flowing to my shoulders where I felt the soft pressure of her hands. She would feel it, subliminally or otherwise.

My breath was beginning to mirror hers after a couple of moments. I was sure I wasn't imagining it, and I knew our ribs were moving at the same time. I felt her presence and attention as she responded, consciously or unconsciously, I don't even know.

Once I knew I had it, it was time to diffuse the intensity, keeping the situation light. I didn't know what she had in mind, getting me into the studio instead of coming outside with me, so I asked, "Can I look around?"

I cupped her elbows in my palms and stayed standing before her, enjoying her hands on my chest and shoulders, while I turned my head to check out the difference between how the lobby looked now, after hours, compared to when I had been here in daylight during business.

Almost all the lights were off. Through the doorway at the back of the lobby, the practice room's brick walls and hardwood floor were softly illuminated by an LED string in the timber rafter-beams, and a single low-wattage spotlight shone diffusely on the obligatory altar table with a modest terra-cotta figure on it of some Hindu god or goddess, with the head of an elephant.

The lobby itself was only lit by the dusk coming in the front windows and a desk lamp illuminating the area by the retail terminal. There was plenty of light to see by, but the low level begged for either a prompt departure to let the studio rest for the night, or else the immediate commencement of carnal activity, oh yeah. I would let Tris direct the show in that regard.

"I'd rather just get going," she replied, petting my chest casually. "It's just that I don't want to turn the lights back on, people might see it from outside and think we're open."

I reassured her, "Hey, no trouble, then. I can look for a carry bag for my new yoga mat next time I'm at class. Doesn't have to be now! I know you wouldn't ring it up right now anyway."

She looked thoughtfully into the practice room, and teased, "Have you seen all the blankets, gym mats and bolsters we have? It's quite a collection!"

I could picture what she was suggesting. "Not really! Just the blankets!"

"We can't go in there anyway," Tris shrugged. "After the last class, the teachers clean it up so it's saaa-creeed or some shit, and they'd get pissed if we harshed the karma in there." She sighed dismissively, apparently not thinking much of this protocol, or of the teachers' anality over it.

"Who taught the last class today?" I casually asked. I wondered if it was Madison.