Chapter 6: Jill the Gambler

On a warm summer’s eve
On a train bound for nowhere
I met up with the gambler
We were both too tired to sleep
So we took turns a-starin’
Out the window at the darkness
The boredom overtook us, he began to speak

He said, “Son, I’ve made a life
Out of readin’ people’s faces
Knowin’ what the cards were
By the way they held their eyes
So if you don’t mind me sayin’
I can see you’re out of aces
For a taste of your whiskey
I’ll give you some advice”

So I handed him my bottle
And he drank down my last swallow
Then he bummed a cigarette
And asked me for a light
And the night got deathly quiet
And his faced lost all expression
He said, “If you’re gonna play the game, boy
You gotta learn to play it right

You’ve got to know when to hold ‘em
Know when to fold ‘em
Know when to walk away
Know when to run
You never count your money
When you’re sittin’ at the table
There’ll be time enough for countin’
When the dealin’s done

Every gambler knows
That the secret to survivin’
Is knowin’ what to throw away
And knowin’ what to keep
‘Cause every hand’s a winner
And every hand’s a loser
And the best that you can hope for
Is to die in your sleep”

And when he finished speakin’
He turned back toward the window
Crushed out his cigarette
And faded off to sleep
And somewhere in the darkness
The gambler he broke even
And in his final words
I found an ace that I could keep

You’ve got to know when to hold ‘em
Know when to fold ‘em
Know when to walk away
And know when to run
You never count your money
When you’re sittin’ at the table
There’ll be time enough for countin’
When the dealin’s done

You’ve got to know when to hold ‘em
(When to hold ‘em)
Know when to fold ‘em
(When to fold ‘em)
Know when to walk away
And know when to run
You never count your money
When you’re sittin’ at the table
There’ll be time enough for countin’
When the dealin’s done

You’ve got to know when to hold ‘em
Know when to fold ‘em
Know when to walk away
And know when to run
You never count your money
When you’re sittin’ at the table
There’ll be time enough for countin’
When the dealin’s done

{r}Kenny Rogers

For reasons both of resources and personality, Lucy fell into a leadership role. “I’ve been thinking about the male-female ratio here if everyone buys in. If everyone were het, we’d have a problem with three men and eight women. Given, though, that three of the women are primarily oriented to women, it’s not as bad. Maybe we could use a bit more ... er ... manpower, unless we have some with very fast recovery.

“I like the way that skills and interests come together. To run the household if nothing else, we have Gigi and Jill. On the parental side, I know that Gigi, Tana, and Jill all like the role. Yes, Art?”

“Lucy, while it’s never worked out for me to be a parent, it appeals to me. I like kids a lot.”

“Great! For the health and fitness side, we have Marilyn, Tony, Diane, Zelda, and Gigi. Tana is our lead stylist, but perhaps Diane will join there?” Diane nodded. “In addition to Marilyn’s nursing degree, I know that Howard has a background in medical research.”

Jill spoke up. “This may take me a bit to explain, but I have some thoughts about additional guys. It’s something that I’m still trying to understand.

“I do have a teaching license, but I decided it was unwise for me to do so. You see, I am attracted to teenage men. Somewhere in that is that they may be androgynous. Before I started birth control pills, I was completely flat-chested.” She cupped her breasts, covered by a lightweight tube top, a light blue that accented her eyes. The top clung to her chest, which was now perky B-cup. With a naughty grin, she pulled at the neckline to offer a brief flash of pretty nipples.

“With my hair bound up, and wearing the right sort of clothes, I could be taken as a boy. What I still don’t really understand is that I can be attracted both to women of all ages, to the boys I mention, and, very selectively, to adult men that I trust, like Howard and Art.

“The legal age in this state is 16. I wonder if we might find a mature 16-year-old or two, who obviously would have very fast recovery times. In no way do I want to do the slightest harm to an immature man, but I think I do know some teenagers, of legal age, that would be safe for thoughtful play. Let’s put it this way -- I don’t want to risk my rationalizing something dangerous. I’m going to tell people what I plan, and I absolutely, positively, want you to warn me away if it feels bad. Definitely talk to him. If it doesn’t feel right, I can be a good friend to someone playing with women of his own age.

“If it does feel safe, for me, that would be a great way to explore my heterosexual side.” She looked around at the women. “Do any of you like cute teenagers?” There were various nods.

“Generally not, unless the kid is really smart and I make an intellectual connection. I’ve been turned on by a couple of sophisticated girls who just didn’t act their age, but it sounds like you are thinking of people who are mature enough, but clearly young. Do your thing, but not with me. Sorry.”

Marilyn was among the nodders. “I like men of all ages, but I have to confess that I really get turned on by initiating boys or helping them develop. I hope that’s different than the idea of despoiling virgins. Virginity, I think, is a correctable deficiency.

“I have to mention something, I think. which Gigi knows about, and could well address some of what Jill wants. For the moment, let me defer to Lucy, who I think wants to talk about other things.

Lucy continued talking about logistics. “In any event, I’d like us to move forward. As I’ve mentioned, I own this building, and money isn’t particularly a concern. Germaine, Tana, Diane, and I already have apartments in it. Are some of you not especially tied to where you live, as on a month-to-month lease?” Gigi, Jill, Zelda, Art, and Marilyn raised their hands.

“I do work from home, Lucy, although Art, who works for a government contractor, goes to a conventional, if secure, office.”

Art looked thankful. “I’ve got a warehouse where I have work facilities for my surplus electronics business, as well as storage. I’m living month to month since I broke up with Ann.” I looked sympathetically at him. Art was a friend for decades, but I had played with Art and Ann. She and I found one another quite hot, although she turned out to be too kinky for Art -- something that I wouldn’t have thought possible.

“So it’s Howard and Tony, that have established places. Actually, Diane and Tana are still moving in. We are arranging subleases for them, as well as moving help. I have no problem in setting up furnished apartments for you guys here, so you have flexibility.”

Tony mentioned “Maybe it’s simpler for me than I suggested. I have an exercise and weight studio at my place. If you’re setting up such a facility here, then I might be fine with taking an apartment here.”

Lucy agreed with Tony. “Tell us what you need, and then let’s circulate it to see if it meets the strength training goals of everyone else. There will also be a dance studio, which can have mats for martial arts.”

Marilyn took the floor again. “What I wanted to mention is that Gigi and I have been talking about our young male family members. You want to start?”

“Yeah, Marilyn. In addition to my son, who’s still not thinking about sex, I have a younger brother, George, who is 16. We share the same miserable parents. George sometimes stays with me to get away from them, which bothers them not in the least. George is a gentleman about it, but I think he knows what I do. I see his eyes follow me when I dress to go out. I don’t think he’s a virgin, but I haven’t asked. I wish I had the courage to do that, and to tell him that mine is a safe place if he wanted to bring a girlfriend -- which would be safe for her as well.”

“Gigi and I have similar situations. In my case, it’s my nephew, Mike, who also is 16. Nice kid with bad parents, who sometimes hangs out with me. Yes, he also finds me sexy. Neither Gigi nor I are ready to take on family members quite yet, but we have talked a little about trading the boys between us. We think it would be much better for everyone to have their first adult contacts be here, without extended family ties. We’re not philosophically opposed to incest, if it’s psychologically safe, and we could get good advice here.

“Jill, I’m a little unclear about what excites you, as well as your experience. My understanding is that now, you’re mostly interested in women, with limited exceptions for very trusted men like Art and Howard. What isn’t clear to me is how much total experience you have with men, and if you would feel comfortable as a what ... mentor?”

Jill smiled. “I can see how you might get that impression, but don’t worry. When I was in college and early twenties, I did date men, or, as it too often turned out, immature men who didn’t have the relative innocence of the boys I’ve mentioned. Especially before I realized that I don’t handle alcohol well, I got into some bad situations, and maybe some that were not all that unpleasant. I avoided men, although Art and I, for a while, would sometimes play, often short of intercourse. Still, I got a diaphragm, and both for convenience and to help some menstrual pains, got on birth control pills. They delighted me by suddenly growing out my flat chest, so I’ve stayed on them for various reasons.

“I am wondering how to present myself to them. I could do teacher they’d like to fuck, or I can still come off as college girl. Maybe having a second woman there is a good idea, unless they’d find it overwhelming. If the other woman is bi, I wouldn’t immediately do anything with her in their presence, so I don’t mess with their minds. In fact, I’ve heard it’s unwise to be particularly wild in choice of clothes and such, so I don’t imprint them, say, with stocking fetishes.”

At that, I coughed. “Um, yes. When I was 16, I played some with a 23-year-old. We didn’t have a safe place besides her car, but I think she would have taught me a lot of good things. Marilyn, as an aside, she was also a RN and resembled you somewhat, except she was a redhead. Anyway, I wasn’t getting it when she was trying to seduce me. At one point, I asked if she was cold, it being winter and her wearing a fairly short skirt, although not as short as current ones. She invited me to explore under her skirt, and feel how warm she was under and above her stockings. Well, I explored and said ‘yup, you’re warm’ and didn’t do anything else ... dammit. That was my start of stocking and heel fetish. Minis were coming popular as I was advancing in puberty, and lots of classmates weren’t quite sure how to wear them, or that conventional stockings would reveal a lot.”

Marilyn turned toward me and pulled up at her hem. “Well, dear, you get to explore those fantasies with me, if you like. Play with my legs, but I’ve also heard that you have a fantastic mouth for something that’s at the top of my legs. Real soon, I hope.”

As I went by, Jill rubbed my back, and stage-whispered, “If you do anything that I wouldn’t do, either show me how to do it, or do it to me.” She smiled “Yes, love. We’re going to do some things sooner rather than later. This is a very, very, safe place.”

Lucy called us over and handed me some keys. “Apartment 310 is set up for guests. We’re getting crowded here; feel free to grab a bedroom there. Marilyn, look at it when you have a chance and see if you’d like to live there.”

Marilyn and I went to Apartment 310, and, after letting ourselves in, embraced while our tongues dueled. She slid a leg between mine and humped my thigh. In a husky voice, she urged me, “Just go right to the fantasy. We can be gentle and romantic later.” With that, I guided her to sit on a couch.