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.