I woke up the next morning with a solid woody, no cage. It felt awesome for a change. Jen must have released me in the night, but she was nowhere in sight to thank. Odd for a leisurely Sunday morning. She’d have been much more likely to be stroking and teasing me. But now, all by myself, I’m seriously ready to get some hand-exercise in, if you know what I mean. It’s been so long! And Jen has been less than available. Not to mention her radical behavior last night; but I don’t even want to think about that for another week.

My mind races to Karla. I know I shouldn’t, but she is so Hot and so intentionally trying to lure me in, for whatever reasons. But now, at least in my mind’s eye I can safely envision her… edging that candy dish farther & farther away, baiting me to fall face-first across her desk.

“Why you naughty, naughty boss. You clearly need another reminder of my Disciplinary Policy. These pants must come down, and this belt is now mine. Perhaps it can teach you how to keep your pants up in the future. Count out loud.” Whapp! Whapp! Whapp!

The bedroom door opened and I snapped out of it, quickly scrambling to recover a sense of decency in the here & now. Jen may have been suspicious, but seemed more intent on her agenda: Getting this off her chest. She sheepishly looked down at her feet as she explained…

“Honey, I am so so sorry about last night. I had no idea the trial period would be so intense. And I just got carried away in the moment. I had wanted to join high society so badly. But I have taken steps to reverse course. I went to your office and left a note on Karla’s desk for her early Monday, thanking her for inviting me, but declining. This club is apparently more than a man of your stature should have to endure. It was so demeaning of Mr. Owner to encourage me to treat you like that. And then to journal all the lurid details, and make you sign it. And the way he treated you and me last night was unconscionable. He virtually raped me, at least raped my mouth with his tongue and my body with his hands. So I need to quit. And I wrote Karla that I am so sorry if it causes her, or her boyfriend, any punishments as a result.”

And then she looked up, straight into my eyes with a mischievous expression…

“And as for you, Mister, being so sweet as to endure what you did last evening, come over here. I want to make it up to you.”

SLAP! SLAP! Her new signal that I could fuck her.

And the race was on, to shed my pj’s and pull her into our bed. Having just been mentally belt-whipped by Karla with 12 hard strokes, I would now take my hardon’s revenge on Jen, the one who really DID finger my asshole last night and passionately kiss Mr.Owner as he painfully juggled my balls in his grip. You’ll pay for that, Jen. And I raped her roughly for ever daring to put my dick in her little cage. In & out, in & out, and… dang… prematurely shooting a load 3 inches deep into her Vagina.

But no matter… Score! Finally!

I was so happy to have cum, that I didn’t mind going down on Jen afterward when she reminded me. And yeah, even knowing what’s coming, ie, her new habit of forcing my face into it — a Pussy filled with my load of cum. And of course, very close to the surface. So it was a lot to eat. Dang. But we laughed, and then showered together. She made a point of soaping my face two or three times, and scrubbing it with the bath-brush each time, to symbolize how nasty that was. And afterward, she made me go down on her again, as she re-conjured the thoughts of my predicament last night, standing dick-to-butt, and butt-to-dick, with other men, obeying Mr. Owner’s commands — competing to gain favor for our wives’ chances at joining the town’s Chastity Club. She had fully enjoyed seeing those other (caged) dicks in the room, even a couple of apparently well-endowed cocks. Their cages would have slipped right off of my dick & balls. It was embarrassing. She hadn’t let on, but she was fully staring at the guy who was after me in line, whose jailed cock had been snuggled up tightly against my asshole. And he would follow after my inspection; so he was pretty much laughing and winking at her, while I was terrified, watching the guy on the other side of me getting berated, kneed and dismissed. And apparently her guy nodded toward me, effectively challenging her to make my inspection equally terrifying. Her thoughts now drifted back again to fingering my Ass last night, pushing me forward toward Mr.Owner, presenting me to him chin to chin. Meanwhile she watched her neighboring cock dance in its ballroom-sized cage. Tremendous fun for her, not for me.

My dick withered after getting Jen off yet again. And she sent me to the kitchen to boil some eggs & cook some sausages for us.

“Use the big sausages, Honey. And the large eggs, please.”

***

My phone buzzed at the arrival of a new text-message.

“I haven’t heard from you lately. Let me guess: You’ve had your penis in Jen’s Pussy; am I right? Well don’t forget me. Remember your commitment to *carry* the cage even if you’re not wearing it. Are you remaining faithful to me in that respect?”

I lied. “Absolutely, Reesa.”

“Ok, I’ll take your word for it, but if you were to ever lie to me about that, you would break my heart. You’re my ultimate friend and now lover, in my mind & heart. I’ve had quite a number of lovers, some very powerful sexual magnetism, a couple with really magnificent cocks pounding me all night long at times. But never you, of course. I never thought I could get off with a small dicked boy, but now, Honey, things have changed and I see you in a whole new light. And, well, I woke up Horny this morning, longing to just be cuddled by someone who truly loves me for who I am, the real me, not just the sexual animal I am at times. Yes, to just be cuddled and have my hair stroked. And even if only penetrated by a small hardon working its way into me a little. Or even if only in a symbolic way, from a thousand miles away. Have you ever wished you could have held me like that? Make out? Maybe unbutton my blouse? I would so Love to have you right here right now doing exactly that. Ever imagine slipping my bra off, Harold? My panties? I wish I had let you come on to me. And now it’s too late for those very real things. You’ll never be able to finger my warm wet Pussy. Nibble at my now-pierced nipple. Or run your tongue through my rose petals. Will you ever forgive me? How could I ever possibly make that up to you? Would you like to sink your dicky into me right now? Into my tight, little, pink Pussy? Oh please say yes, and ask me politely.”

I’m still plenty Horny enough to say yes to such a proposition, even knowing what it would mean…

“Please Reesa, may I slide my penis into your tight little pink Pussy?”

“Permission granted.”

I ran and quickly rifled through my garage workbench to locate the Holy Trainer and attach it to my genitals.

Whirr click.

I had to make excuses then for the rest of the day as Jen continued reliving her only chance at belonging to the Chastity Club — the one she is now giving up. Sigh. And our sexual encounter this morning, the Pussy-eating, the Shower, the punishing face-brushing, and the thoughts of cocks she would never again get to see… well, it made her wonder if she did the right thing by giving it all up. After all, what’s a little humiliation in fun, Harold?

But she written the note, and she would stick by her word. Still though, it wouldn’t necessarily mean my dick would escape scott-Free. Maybe she should still require a cage from time to time.

“Honey, now that I’ve given up on the Chastity Club, would you agree it’s only right that you should still be caged from time to time?”

“If I must.”

“You must.”

***

After our Sunday afternoon of me avoiding her horniness, she doubled down:

“And now I’m remembering how your dick is just not available enough to me — I need more. It’s why I thought the Chastity Club would be perfect for you. Oh and for me. In fact, since I’ve given up what could have been a steady diet of seeing lots of other cocks each week, isn’t it only fair that I get to see maybe a cock or two every once in a while? Is that too much to ask?”

“Hey! What exactly are you driving at, Jen?”

“It’s only fair, Harold. What say you escort me to the Adult Store from time to time?”

“No! Now let’s drop this and get some sleep. No self-respecting Wife of mine should be seen out there at that store — except for the Club Room. Too many perverts, video-booths, guys shopping for whips & chains, or dildoes… and whatever other kinds of booths and activities. Now get that out of your mind and go to sleep.”

And yet, I myself wouldn’t be able to sleep a wink, knowing she always gets her way.

***

Monday morning was tense. When I walked in, Karla was flushed and visibly shaken. Holding my Wife‘s note in her hand, she started to cry.

“Please Mr. Harold. Please talk to her. Please reconsider. Did you even try it for a week?”

“Uh, er.”

“You did, didn’t you! You went to the first Reporting Night and it scared you off, didn’t it? That’s the worst one; I promise you it gets better — that one is just to scare off the ones who will fail anyway. You’ll see, I promise you it’s pretty much a breeze from here on in. Just a few chastity nights, and a Voting Night, and you’re a shoe-in. Please don’t give up now, Mr. Harold. The penalty for a failed Sponsor is severe — more than you even know. Please don’t make us endure that. We’ve seen other failed Sponsors punished in front of the whole club membership and it’s horrid to even watch. I beg you: Reconsider. Please? Even just try one more week?”

“I’ll talk to Jen. We’ll see. Now dry those tears and hand me a candy. With your teeth.”

***

Sweet! Karla’s lips were so sexy. Her brief kiss made my dick immediately hard. Painfully so. I had to hurry to the Mens Room, fumbling with my phone, texting, hoping to get release.

“Reesa, Sweetheart. It’s time for me to pull out, don’t you think? I’ve been in your pink Pussy for almost 20 hours already. Time for a break, ok? Whattaya say?”

“Oh Harold, Honey. That’s not even a full day with me. Why do you want out of my Pussy already? Don’t you like dipping your penis in my Pussy? What’s going on with you? You’re not just wanting to jack off, are you? I hardly even know what’s going on in your life, what you’re doing, what you like and don’t like. Missionary or Cowgirl, Doggie, or what? Please share more of your life with me. Every detail. That’s what lovers do. So how about this? Like every Wife asks about her husband’s day. And if he shares these mundane details — which are very interesting to wives, then (and only then) does he get to later push his thing into us. So let’s do that. I’ll let you slide out now, so you can concentrate on your work, but I want you to promise to log all your activities of the day, so we can review your day together… tonight. And if you’ve been a good boy (of course), then I’ll let you slide into me. But it has to be *all* your activities, including hardons, Sex-talk and of course intercourse.”

“You promise not to be jealous?”

“I promise. If you agree, I’ll release you so you can get started on a log, and we can review it tonight. Deal?”

“Deal.”

“See you then, Harold, Honey.”

Whirr Clack.

My pants were down immediately, and I pocketed the cage. My hand took over, whacking off at a bruising pace. The thought of Karla’s lips are driving me crazy. I had never gone that far with her except in my dreams. But the brief encounter was very real. And shortly, real cum was flying.

***

Returning to my office, I opened a new google-doc as a log, to be shared with Reesa… later.

Hmmm. Lets see.

1.) Woke up with this cage bruising my woody.

2.) Cold Shower.

3.). Sticky conversation with Karla.

And the candy-kiss.

No, wait, I dare not tell Reesa about Jen’s new club application and trial-period experience. Make that just…

3.) Karla fed me a candy, mouth to mouth, and it turned into a brief but sexy kiss — maybe not meaningfully, but just a flirtatious gesture. Probably just wanted to see me get hard in the office.

4.) Begged you to release me — sorry I didn’t tell you the real reason I needed out.

6.) And jacked off in the stall of the Mens Room, thinking of Karla’s kiss. (Reminder, Reesa, you promised not to get jealous if I was honest with you, sharing intimate details.)

7.) Cleaned off the stall wall, and went back to my office.

8.) Worked all day, uneventfully really, except remembering that candy-kiss. Karla tried to be very professional for the rest of the day.

9.) Drove home… with a hardon, mindful of sharing these intimate confessions with you, Reesa. And remembering well, way back in the day when we used to work together, I used to fantasize about your sexy mannerisms. And it always felt like, at just the very moment I might try to see if you had any feelings for me — for instance, after we had played a prank on the Administrator — remember, your boyfriend would stop in and sweep you off your feet. Your dreamy brown eyes would suddenly turn to him. You had always been pining and telling me about Richard, for instance. And remember that first time he stopped in and I was the only other person around? We were friends, so you didn’t even hide your lust for him that day. You ran to see him and jumped up on him in a most unladylike way, wrapping your arms around his neck to passionately kiss him as your beautiful panty-hosed legs wrapped around him. Your short skirt rode up nearly to your waist. And after what seemed like an eternity to me, with your floral panties quite obvious still, you turned to me and winked. You knew I was watching, as you continued kissing, making him tent his suit pants. And then, and then only, having demonstrated your obvious sexual attraction to him and he to you, you introduced me, while still pressing your clothed Vagina to his hardened cock. Your boyfriend whom you had so often been telling me about — at times almost baiting my dick to get hard. Admit it.

10.). So yes, I was as hard as a rock when I walked in the house, with my briefcase covering my situation.

11.). Worse yet, now I need to tell Jen about Karla’s begging. (And not about the candy-kiss, much less the Masturbation session.)

So here goes…

“Jen… Maybe we should reconsider. Karla was in tears this morning, mortified as she anticipated the punishment of failed Sponsors. And she swears it gets easier in future sessions. Should we give it another week and then decide?”

“Oh how sweet of you, Harold! You big softy. After all you went through Saturday night, you’re willing to forgive & forget, to save a couple of young people some pain… and make a valiant effort to gain Chastity Club membership for me, your sweetie. I am so flattered. Well if she’s that afraid of failure, maybe we should test the waters and negotiate a little further. I think I’ll give her a call at work tomorrow.”

***

Later, the text from Reesa came…

“Well? Share the log with me?”

I complied, sending her the link and waiting anxiously to know her reaction.

“Oh Harold, you naughty naughty naughty boy! I had no idea that a penis your size could have so many sexual thoughts & ideas and predicaments. I just assumed the sexual side of your brain was no larger than your penis. Well! Now you’re really in trouble, Mister! You’ve been holding out on me all this time, with thoughts of such jealousy, even monitoring Richard’s hardons. And looking up my skirt. Even remembering which panties I had on. You really really need to be disciplined, Mister! I can’t even consider letting you slide your dicky into my pink Pussy tonight. Maybe you need a few whacks. I know you must think I can’t do it from here. But you’re wrong, Mister. So here’s what I want you to do…”

She continued with another long text…

“Tonight when you go to bed, change into your pajamas while you wait for Jen to finish in the bathroom and brushing her hair. And when she approaches the bed, I want you to stop her, telling her that first you need to confess something. Stand by her side of the bed, bend over it and take down your jammies. And confess that you had thoughts, just thoughts, of kissing your secretary — the truth would kill her — and then you went and jacked off in the Men’s Room. Tell her to do whatever seems right to her. “

***

(to be continued)