Katelyn’s Locktober Dilemma

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Chapter 1

Harold, can we not talk about the weather so let’s sit down here and skip the rest of our walk. Let’s see where 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 ardahan escort 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 adıyaman escort 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 karabük escort 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????

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