Katelyn S Locktober Dilemma

Chapter 1

Harold, can we not talk about the weather & sports & politics today as we walk? I need to talk to someone about something kind of important. And in this case, I need to talk to a man friend -- but someone who won't judge me for not already knowing about stuff like this. Promise you won't laugh, though. Ok?. Anyway, it's about something that my daughter Cyndi was all chatty about to me when I went to visit her at the University this past weekend, and I am totally confused. And don't know who else I could ask but you.

No problem, Katelyn. I wouldn't laugh at you, no matter. I promise.

Thanks, Harold. I appreciate you always being such a good listener -- not to mention coaxing me to speed-walk regularly!

Ok, so here's the thing... To be honest, I had never even heard of this thing, but (as always), she was like: Oh Mom, you're so old-school! C'mon, get with the times! Women are making great strides these days. It's not like the 80's (or whenever it was you grew up in back in the day before Women's Lib, no offense intended toward Dad, or now Peter).

So what was it, Katelyn? I'm curious?

It's pretty embarrassing, Harold, to have to learn about things from my daughter for gosh sake. So I just played along as best I could, saying yeah, uh-huh, and so on -- not wanting to ask questions. I went online to research it, but my browser's safety settings wouldn't even allow me access to this thing. So I'm still terribly confused. And I really need a guy's opinion before I mention the topic to Peter. From the way Cyndi let on, boyfriends & husbands can be pretty defensive about this sort of thing...

So... here it is... My question to you, Harold: Dare I ask Peter... to, uh, well, hmm, wow, how do I say this?

Katelyn! Stop. You're driving me crazy. I can't very well give you friendly advice if I don't have any idea what the heck you're all worried about. Besides, your pace is way too fast when you're all worked up like this. Slow down, take a breath...

Now... start back at the beginning. What happened when you went down to see Cyndi over the weekend?

Oh. I'm sorry, Harold. You're right. I am pretty worked up about this. I'm such a dork-mom I guess. Ok, here it is. And I promise to slow down a step or two. Whew. Ok, where to begin? Ok, it was like this...

...When I arrived, we had barely got to talking, when her doorbell rang and she received a delivery. One that she was all excited about. "Mom, you are going to be so proud of me when you see thing. It's a present (sort of). For this guy who asked me out for next Friday. I don't believe in re-using these gizmos, so I always get a new one for each new boyfriend. Besides, I really think ex-boyfriends need to keep theirs anyway. No point in girls being stingy about such things. Right, Mom?

But, Harold, I had no idea what she was talking about, so like I said, I just played along. Anyway...

So she opens up the package, and it's something in a nice velvet bag. And... Hey wait, do you already know what she's talking about? I don't want to have to say it outloud, if you already know. I'm such a dork. And it's embarrassing. Besides, I'll bet you DO know already. Yes?

No idea. (I lied.)

Ok, if you're sure. Ok, so it's probably just a college dating thing. Maybe even provided by the universities these days -- college life is a whole lot different than when I went, not so long ago even. You know, when I was in college, girls were considered tramps if they weren't virgins. So no way did we even think about buying such items for our boyfriends, much less, even for a first date!

(I couldn't argue with her there. And I sure wasn't going to introduce myself into this conversation. So I continued playing dumb.)

Ok, so keep going, Katelyn. Are you going to tell me what it was, or not?

Well... I suppose we're supposed to think of these things as more of a safety device than as something sexual. In fact, it's kind of an anti-sexual contraption. You see, when a guy fastens this thing -- they call it a Chastey, I think -- onto his privates, and locks it, it makes it hard for a boyfriend to get the device off quickly in a moment of passion. And that gives the girl time to make her getaway and run. Or I suppose if a girl was a super skittish type, she might even ask to hold onto the key during the whole date, until the date was over. But like I said, I don't know how it all works. That's why I need your advice.

Uh, advice about what? Why can't you just forget about it, and chalk it up to a college girl safety program of the University?

Yeah, I would, Harold. Except Cyndi said that since it's Fall now, all the women are getting ready for October, and said if Peter hasn't already asked me to, I should ask him to wear one of these devices. She said at college, it's like an invitation to go steady. A loyalty pledge of a sort. And any guys who wouldn't ask a girl to hold their key for the month aren't to be trusted, she said. And certainly not marriageable material. So she could hardly believe Peter hadn't already asked me. "After all, Mom, you are going steady with him since your divorce from Dad. Right?"

Wow, Katelyn. Uh, yeah it sounds like just a college thing. So don't worry about what Cyndi said. Btw, can we change the subject. How is your job going these days?

No, wait, Harold. Help me out here. I really need your advice. Should I order one for Peter and ask him to wear it? Or do you think he's already ordered one and will pop the question just in time, on Saturday night? Time is running out.

Btw Harold, have you already got one and asked Jen to be your 'steady girl' for October? haha. I know, I know, you two are old fuddi-duddies. Probably have long ago given up all your sexual games. Don't answer that -- I do NOT want to know about how or how often you make love to your wife. (Of course, you'll probably tell me in due time anyway, right? ^wink^)

Anyway, so help me: Yes order him one? Or No, wait for him to order one for Saturday night?

(In a brilliant moment, Solomon-like wisdom came to me, not a second too soon...)

Hmm. I guess you could order one just in case. Have it wrapped, with a little bow & all, and keep it in your purse Saturday night, just in case Peter hasn't heard of all this, or thought it just isn't the sort of thing for him. But if he has planned it all out to offer it up on Saturday night, he would never need to know you didn't have confidence in him.

That's a wonderful solution, Harold! (And she stopped fast-walking long enough to grab me and give me a peck on the lips!)

Could you help me find somewhere to go buy one or order one, Harold? You're a worldly man, right? You'd know where to begin looking, right? And you have male 'equipment' to get some approximate measurements, right Harold? Tell you what, if you help me and it turns out to be all for naught, I'll let you keep it free of charge. Ok?

Uh, I'll help you, Katelyn, but I don't think I'd want one of those. Ok? I mean, I'm not a chauvinist or anything, but 'that' doesn't sound like anything I'd want to do, or have hanging around my house for Jen to run across.

(Again, that was a big lie, since I own one already. I bought it at one of those super-truckstops one time when I was away from home and horny as fuck, passing all the Adult Stores along the way til I came to this place: The little college girl running the pop-up concession at the truckstop had several guys gathered around listening as she was making her sales pitch, swearing that it would keep us awake at the wheel, as well as being an absolute guaranty of fidelity. Something we could proudly show our wives that we were all good boys when we got home. She said from a woman's point of view, this will absolutely endear her to you all forever! So when the other guys jumped at the chance to buy one from her, so did I. And it turns out she mails the keys and special note to our loved ones as a One-Time Special Overnight Delivery, free. Dang. And she was absolutely right. I couldn't have fallen asleep at the wheel that night if I had wanted to. I drove straight through, being sure to arrive just in time before the girl's note & the keys arrived. But then I totally chickened out about letting my wife in on it!)

Oh Harold, you aren't too old to enjoy a little fun time in one of those things are you? And besides, what a great message it would send to the women in your life, as at least one small way you support us in our battle for equality, right? It sounds like a great token gesture of support, from what Cyndi said. Anyway, no matter, it may not even come to that; so let's sit down here and skip the rest of our walk. Let's see where & how to get one! You have your phone, right, Harold? And dare I guess you already can hit the porn sites just fine. So do a search for "where to buy a chastey?" C'mon, sit down here Harold and get to it. I want us to read and learn all about these things... and then buy one, ok?

(Dang.)

So I did as Katelyn asked. And pretty much ended up having to explain the designs and features to her. It was embarrassing. Worse yet, she was enjoying laughing at all the caption pages, and seeing men's dick's locked down. And then quizzing me about how that must feel. You know, since she didn't have a dick or could possibly know the feeling for herself. It was getting downright annoying to see how much she was enjoying these men's anguish. I had always thought of Katelyn as such a perfect friend, confidant and caring woman -- in contrast to how Jen could be at times. Yet, here was Kate, laughing at small dicks (not unlike my own, if she only knew), trapped in these devices for hours, days, and even a whole month each year.

One caption that made her burst out laughing each time it showed up, was one depicting the wife saying: "Ok, our weekend start into October was fun, but now OFF YOU GO, Mister Big Executive! Say hello to your Boss Lady for me! ^wink^

And only finally, when Katelyn realized how late it was getting, she had me move on to the online stores that sell chastity cages. So then she was having me explain the technical side of things... You know, about the base ring size (50mm, I suggested, based on how tight my 48mm is on me. but I didn't mention that.) And I tried to talk her into a manly looking black device, but she insisted on pink. And she was adamant that Peter was probably smaller than guys like me, although noting my small package didn't even register through my running shorts. Ultimately so she decided the Nano should work, and "just too bad anyway, since I'll only need it in case he's too insensitive to remember Loctober!"

So, Harold, hit the 'Buy Now' button and let's get this thing coming. Time's wasting. Besides, you know I'll pay you back, right? I'm good for it. Or it'll probably end up being yours anyway, since I'm hoping that Peter will come through for me just fine Saturday night, right? So come on, hit the button. There, thattaboy, done! Perfect.

Gotta run now. See ya tomorrow, buddy. And if it ships overnight, bring it with you tomorrow, ok?

Sure, Kate. (sigh)

Oh, and Harold. You can open it to check for shipping damage, but no playing with it. Ok? Peter won't be wanting to be wearing something another man's dick has been in. Trust me. He was all sorts of bent-outta-shape when he learned about my previous boyfriends, if ya get my drift. ^wink^ LOLLLLL.

Me: ^rollingeyes^

***

Sure enough, a delivery guy came to our door the next morning (and I had to RUSH to be first, and sign for it -- not to mention having to come up with excuses to Jen why I didn't open it right away.

So I was glad to get it out of my house when it was time to go power-walking on the trail again.

***

Did it come yet, Harold? Did it come?

Katelyn had arrived early and was anxiously awaiting me to pull in and park.

Yeah. Here, Katelyn. Good riddance. Go put it in your car and let's hit the trail.

Don't you even want to see it, Harold? I mean, you didn't even check for shipping damage like I asked you. Come on, slow down; we're not in any big hurry. In fact, I could hardly sleep a wink last night, thinking about you bringing it today. Aren't you excited too? I mean, you'd never heard of one or seen one either -- much less, worn one. So surely you're as curious as I am. Aren't you, Harold?

Uh, sure; curious, but it can wait. You can tell me all about it after Saturday night, ok?

Oh Harold, I can't wait that long, ya goof! I want to know everything there is to know about it, before I ask my guy to wear it. I mean, if he's as oblivious as you are, Harold, won't the shock to his male ego be a bit overwhelming to him? And what about the risk of it breaking as we put it on him? Or what if his small penis can't handle it for whole days at a time? Didn't some of those captions joke about not even giving their guys a "break-in period" -- so it kind of sounds like the device really should be tested and tried before Locktober, don't you think?

Locktober? Is that what you just called it?

Yeah, I guess I did. Maybe I saw that in a caption somewhere. Anyway, yeah Harold, I think that's the fun name for it. After all, it is supposed to be fun -- not some kind of cruel punishment. Didn't the sales site say that?

Yeah. I guess.

Ok, so open it, Harold. I'm too excited to do it. (And she covered her eyes -- I had little choice but play along in 'ignorance'.)

(Dang! A Nano. Shit that's tiny. My dick started moving and pulsing at the very thought. I could scarcely touch it. Fuck that's small.)

Ok you can open your eyes, Kate. And here, take it. Maybe I'll go stretch and get ready to go while you look it over and stow it away in your car. Then let's walk, heh?

Ok Hun. Go on. Go stretch. Gimme a moment with it. I'll be right there.

(Good deal. Finally. Anyway, so I stretched while keeping one eye on her as she was gleefully examining it, even holding it to her crotch as if she were a male with a caged dick. And laughing to herself.)

Finally she closed her car door and caught up with me as I started down the trail.

Thanks again so much, Harold, for helping me understand all this and get one. I owe you, buddy. So...

...how do you think Peter will take it, when I present him with it Saturday night? Or I should say IF I need to present it Saturday night? I mean, try to help me think through it, Harold...

What if he really is that insensitive and doesn't offer me the keys to one he bought for the month? Why wouldn't he think I was that important to him, anyway? We're more than steady, you know. We may not be living together yet, but the man has seen all there is to see about me, and touched places that only a husband should be touching. Or maybe I should just say it out loud -- you're a big boy, Harold. He fucked me last Saturday, and stayed the night. That's how I know the size of his penis -- are you ready for this? I sucked him off the next morning when I felt his woody in his sleep. Can you believe I did that? Can you imagine, Harold? I'm guessing you can. Right?

Uh, er, ah...

Wait Harold! Stop right there. Stop. Nobody's looking. So look at me. Stop playing dumb. Look me in the eye. Can you imagine me sucking a penis in my bed on a Sunday morning... or not? Or don't you think I'm sexy enough to get a guy's penis hard? Yes or no? Are do I need to prove it right here on the trail?

Damn Katelyn! Stop. Of course I can imagine that. Now let's move on before someone hears you.

Or someone sees that hardon in your shorts, heh, Harold? ^wink^ Oh, ok. I was just messin' with you, buddy. You know I wasn't really going to do that, right? Anyway, glad to see you like me though. Thanks. ^smile^

Geez, Kate. You're a giant tease today. What's got into you? You're not normally like this. Cut it out. I don't want Jen to find a big stain down there when I come home.

Oh ok, you ol' fuddie-duddie. You're no fun. ^wink^. It's just kind of exciting handling that cage and thinking about something a little different (finally) on the womanhood front for a change. Nice to see some movement. And if it causes some 'movement' on a man's front ^wink^, isn't that also a little fun? You know it is, Harold. And I know movement when I see it, my friend. ^smile^

Anyway...

So of course I'll be upset if we get to midnight and he just goes to kiss me at the door and leave. Or worse yet, if he tries to, you know, slip a hand down in my clothes, or try to wrangle an invitation inside. I'm tellin' ya, I've made up my mind, Harold: If that man doesn't have a chastey on by the stroke of midnight I will be so insulted! So how should I handle it, Harold?

Uh, oh I don't know, Katelyn. Just take a Sadie Hawkins approach and ask him yourself. Just pull the gift out of your purse and hand it to him. Tell him it's just for October and if he's not interested, to just move on; you don't want to waste anymore energy on him. He's not worth it if he can't at least sacrifice a little of his privilege.

Good stuff, Harold!!! Perfect! That's exactly what I'll tell him. And then I'll bring your chastey right back over to you Saturday night!

(I didn't respond. I don't want to get into a tif or anything right now. She and I are on great terms, and I don't want to spoil it over something that might never happen anyway. So instead, I just picked up the pace and it pretty much left her breathless and unable to talk any further as we made our way back toward the cars.)

(Panting), Katelyn was exhausted, leaning over, hands on knees, breathing hard but still wanting badly to ask me something apparently:

So Harold.... aren't you... the least bit curious... about how... a chastey feels... when you're... wearing it? Btw, are you SURE... you've never tried one on? Why else... would you NOT be the least bit inquisitive? You didn't even look it over... closely...

...And here I am, just the opposite! I cannot imagine what it must feel like on a man's genitals -- holding them snuggly in check, with your penis shoved down a little pink tube. C'mon, that's gotta be a strange feeling. And you're not even curious? I'm not buyin' it. You've either tried a chastey on before, or you don't trust me to let you take it back off again. Which is it, Harold?

Neither. I'm just a little too tired for games right now, Kate.

Oh come on, Harold. I walked as far as you did today, and I'm still excited about this. Besides, back there on the trail YOU got pretty excited yourself. I saw that myself!

Uh, er, I gotta go, Katelyn.

Harold, if you leave me hangin' here like this, I'm not going to be very happy with you, Mister! I need help. Now help me, damn it.

Reaching into her car and pulling the velvet bag out and putting it firmly into my hand, she was not to be denied.

Harold, now stop being a little baby, and go over there behind your car and at least try this on. You don't have to even show me. And you can take the key with you if you want, But if you won't do it, I'm going to ask the very next guy who comes down this trail to do it. SOME GUY IS GOING TO TELL ME... TODAY... WHAT IT FUCKIN' FEELS LIKE!!! I need to know! And a man is the only one who can answer that! Now are you going to help me, Harold? Or not?

Ok. Geez.

Resigned to the task, I took the velvet bag & key over behind my car, and after looking both ways, I pulled my running shorts down far enough to get the ring on, and then reluctantly, spit into the small pink tube and wiggle it onto my dick, and locking it up (but clutching the key in my fist) I hardened immediately. Well, as far as it would allow anyway, which was pretty much no allowance at all. My dick was going stir-crazy in that little nano tube! Shit! Fuck!

Harold! She called over to me to hurry up.

Come on, you chicken. Come talk to me! You can stand on the other side of my car if you like, but don't you dare take it back off til you come over here and tell me exactly how it feels! You men don't realize how lucky you are to know the apparently great feeling of getting a hardon. We women go our whole lives never knowing that feeling. So Buster, you had better start talking, and talking quick! How does it feel to **NOT** be able to get fully hard, Harold????