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Chapter 21 by caitlynmasked caitlynmasked

How is the flight for Sadie?

Sadie is nervous at the airport

The morning of the trip I get up extra early. It cuts into my sleep but I’m hoping that a relaxing three-hour flight will help take care of that. In the shower I’m happy to feel the chastity cage unlock as I wanted to make sure everything was clean and fresh down there for the trip. When I finished cleaning myself and the cage I put it back on but noted it didn’t lock back into place.

After the shower I get into my room and lay out my clothes, a comfy pale pink pair of athletic short shorts along with an adorable matching hoody, and a pair of white heeled tennies. Normally dressing so casually I’d wear a normal pair of black bikini briefs or maybe some colored boy shorts, but to help save time when I change into my dress I go ahead and slip into my white lace panties and matching bra. I take an extra few minutes in front of the mirror dressed just in the bra and panties, as I hadn’t worn something so simple and elegant and feminine before. Everything to date had either been more overtly colored, been more ‘in your face’ sexy or had been almost stripperesque in style. This? This looked like something a woman would wear to impress a lover.

And it would be completely wasted under the shorts and hoody. Hell, I wouldn’t even be wearing the bra with the dress as it couldn’t hide a bra away.

I take extra time to style my hair up into a crown braid. It certainly wasn’t part of my normal ‘Princess BabyDoll’ style book, but it was something that would hold up for the whole day with minimal work and would look good in casual wear and even better in the dress. My makeup on the other hand was put on quickly. I’d grown to be such a quick hand with it that, like Sarah, I barely needed the full vanity any longer. In this case, the makeup was just for the flight as I’d completely re-do my cosmetics for the meeting.

When I was all dressed and ready, I packed up two extra sets of clothes, the dress, a spare workout outfit, two sets of heels, and an extra pair of comfortable shoes. I took a small clutch that would work for the dress, as well as a regular purse for the rest of the time. I packed my cosmetics case with everything I’d need for tonight’s special look and the next day’s relaxed return flight look. I added a pack with all my personal bathroom items, and finally slipped Sarah’s little pill bottle into my carry on that had my laptop, my Nintendo switch, a couple snacks, and a magazine.

After double-checking everything I grabbed all the bags and put them next to the door. When I saw Sarah at the table, I had to do a double take as she was sitting there earlier than she normally woke up, sipping at a cup of coffee, reading something on her phone, while she twirled around a white plastic chastity cage in her other hand. Tilting my head to the side I say slowly, “Ummm, Sarah? What’s with the cage?”

Sara doesn’t even look up from her phone when she replies, “It’s for you stupid. Or did you want to walk through airport security with an electronic computer-controlled metal chastity cage around your clitty that will set off every alarm and have the TSA pulling you into a back room for a ‘very special’ search?”

Sarah calling my penis a ‘clitty’ aside, she paints a very vivid picture. Taking the white cage from her I see that it has an included lock, but it’s all made of plastic. With my current cage, I’d have to see a locksmith to get out of it. This one, being all plastic, would only take some basic tools and very special care to break free of. Holding it up I ask, “Are you sure this one won’t set off any alarms?”

Sarah finally looks up at me with a deadpan look, “I wouldn’t give it to you otherwise. Go ahead and change. I’m pretty sure Marley will be here soon.”

I wanted to talk more about it, maybe even ask about using the clip, but the thought of Marley coming and having him wait while I slipped into something to hide away my… well, it got me to shift gears and going quickly. In the bathroom I knew the routine. As I’d already cleaned, it should be a simple matter of pulling myself free of the first cage, setting it aside, and pushing myself into the new cage before the blood started to flow. If I hesitated or slipped up outside of the cage, I’d start to grow and then would need the ice.

After a deep breath to steady myself, I pulled myself free of the old cage, set it in the sink, and started working myself into the new cage. It took a lot more effort than I thought, and I had to squeeze quite a bit more than I had to with my old cage, but as I got it into position it ratcheted into place, locking itself automatically. When it was in place I looked at it as close as I could, and realized it was smaller than the previous cage. Significantly smaller. I had no room to grow in it and even fully soft was stuffed into its confines.

After double checking to make sure Marley wasn’t here, I rushed out to the dining room, pulled down my shorts and panties and pointed at the new cage. “Sarah? What the hell, we can’t use this one. It’s too small!”

Sarah looked down at the cage, looked up into my eyes, looked back down to the cage, then looked back up at my face with a big smile. “No, it’s not too small. It’s just smaller than you were used to. The hormones and constantly being soft has made you shrink. I’m not sure if it’s changed your size when erect, and we might look into that before we see Dr. Lacy, but you’re definitely smaller. I noticed it a week ago when you first let me use the new toy on your back pussy.”

I couldn’t help but blush as she called my asshole my ‘back pussy’. She continued as if that were just the natural name for that part of my body. “I saw that it took you a good minute and a half from your fully soft state to the cage stopping you from growing. And you groaned when it stopped you, as if that hurt more than being held back at all. I found a site online that talks about it, and they say you should be in as small of a cage as you can tolerate. And look at that…” she reaches forward and tickles her fingers under my scrotum, bouncing my caged penis around “…this one fits you perfectly.”

I need to tell her that I already feel as uncomfortable as I do when I’m aroused in the previous cage. I need to tell her that I’m worried about being held this tight for days when I won’t have a key for release. I need to tell her that this is just flat out wrong to do without letting me know. But at that very moment Marley’s knock at the door is accompanied by his loud voice “Sadie, come on, we have a flight to catch!”

As Sarah jumps up to get the door, I pull my panties and shorts back up and just try to get used to the tight crushing feeling. It’s not that it outright hurts, it’s just not comfortable. I’d grown used to my old cage and at times I could forget it was there. But this… this I wouldn’t ever forget about. Having Sarah touch me down there would normally have me swelling in my cage, but there literally wasn’t any room for swelling. The arousal just mixed with a new low-level ache where the swelling used to be.

Marley seems a little nervous himself as he helps get all of my bags in the car. I have to laugh as it all ends up fitting, but he has to take his one bag out and re-arrange all the bags three times before he can get the hatch to close. Even then, I still have to put my carry on in my footwell. I do my best to calm Marley down as I’m sure he’s nervous about meeting the investor. Thankfully he doesn’t take his nervousness out on the road and we calmly make it to the airport where he parks in the long term parking ramp. We’re hours early but we still move quickly to get checked in, check in our luggage and get to the security line. It’s in that line that I start to get nervous myself. I hadn’t even considered what would happen with my cage before Sarah mentioned it and now it’s all I can think aboutg. Not only that, but what if I get pulled out for a random screening? What if I have something else metallic on and they need to do a search? What if they are using one of those new full body scanners? Would it show up on that?

I was near shaking when we got up to the security area and felt a lot better when I saw they had two lines, one with a full body scanner and one with the older metal detectors. I made sure I went to the metal detector and walked through happy that…

The loud beeping detector scared me so bad that I actually jumped and let out a little yelp of surprise. The bored looking security officer looked at me and asked me to step outside of the line so he could use a wand. I turned to look for Marley, but he’d stepped over to the body scanning line and was out of earshot. Feeling like all the blood in my body was collecting in my face I nodded and stepped aside with the officer.

He had me step wide, hold my arms out, and then started wanding me from the head on down. When it beeped as he was going down my torso he asked casually “Miss, do you have any body jewelry on?”

It took me a moment to realize what he was asking but practically shouted out, “Yes! I have a belly button ring!” when it hit me. I didn’t even wait for him to ask and pulled up my hoody, showing my smooth belly and the cute pink jeweled belly button ring. The security officer was still unimpressed, asked me to lower my shirt, and continued to wand down my legs. When he let me go, he simply reminded me to remove any jewelry before taking a flight or to at least inform them before the scan.

When I caught up with Marley on the other side of security we were in the exact opposite positions, and he was actively trying to get me calm down because I was a mad mix of distress and relief.

Marley took us to the lounge near the gate, which is how I learned that we were going to be flying first class. We had a little snack, got some bottled water for the flight, and just relaxed. About a half hour before we headed to the gate, I got my pills out and swallowed them down with some water. By the time we were boarding, I could feel them kicking in and was relaxing already. When we sat down, I snapped a quick pic, sent out some social media posts about the trip, and then turned my phone into airplane mode as well as turning it off to save the battery. When I looked up I saw that the last passengers were milling past and the stewardesses were delivering drinks to the first class passengers. Marley had ordered us a couple glasses of champagne. Holding his glass up he says, “To ambition!”

I clink glasses with him and down most of the bubbly in one go. When I set the glass down, I catch Marley watching me closely and turn toward him, “What? Did I spill something? I’m a little nervous about flying and…”

Marley takes my hand and laughs. “Yeah, I noticed you getting more and more nervous. I get it too. Don’t worry about it, I take a couple Ducenes before I fly and they keep me from freaking out. I cut one in half because you’re so tiny and I put it in your champagne. You should start feeling better in about twenty minutes.”

I continue to stare at Marley as I do the math in my head. Since Ducene is the same as Valium, I’ve now taken a dose and a half of it. As well as two other meds that will all make me relaxed and sleepy. And as I think about it, I do feel them kicking in as my body starts to feel heavy and my eyelids start to feel like they’re sliding shut. Leaning the seat back I put my phone in my carry on, put the carry on under the seat, and buckle up my seat belt. With my eyes closed, hearing him already chuckling at me, I tell Marley, “I’m just going to go to sleep. I’ll guess I’ll see you in Vegas.”

The meds work amazingly well slip right into a dream where I’m kneeling and jacking off Marley, nervously waiting for him to cum right in my face. In the dream I have to keep looking at the tip of his cock as I hear him murmuring my name above me over and over.

“Sadie. Sadie. SADIE!”

I feel my shoulder being shaken and it takes me a second to realize that it’s not pre-ejaculating Marley calling out to me, it’s just Marley. Fellow passenger Marley, waking me up on the airplane. When I open my eyes, I feel awfully refreshed. And then I notice how I’m sleeping. I have my head resting on Marley’s shoulder. More than that, I’m leaning over on him with both my arms wrapped around his big arm, and my fingers interweaved with his fingers. Turning my head up to look at him, I see him smiling almost apologetically. “Hey, I tried to move you, but you’re really insistent when you’re sleeping!”

Clearing my throat, I pull my arms from Marley and move back into my seat. I see that people are already disembarking and remind myself to tell Sarah that her meds are perfect. Those, plus an extra half Valium made me miss take off, the entire flight, landing, and taxying in. Pulling my bag out from under the seat I get my phone out and see that I hadn’t actually turned it off. Unlocking it, I use the camera to check my makeup and then turn the airplane mode off. As it dings away, catching up on all the social media and other app notifications, I slip it into my bag and follow Marley out of the plane and down to get our luggage.

On our way to the luggage pickup Marley leans over to me and says, “Hey, before you get out of airplane mode on your phone, check out your Instygram and TokTic. I got some cute pics of you that I thought you’d like to use on your social media but didn’t want them to go out before you saw them.”

Stopping, I pull my phone out and quickly bring it up, knowing I can delete any social media posts if I get to them quickly enough. If I don’t delete them, then they go live and even if I delete them, people will have already seen them, reposted them, and they’ll be everywhere. I have maybe a few seconds before that’s whats going to happen. When I get the phone out though, I see the dead battery signal flash on the screen a couple times before it turns off.

Fuck.

How does the meeting with the investor go?

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