Sailing Away Ch 23

Lacy, done with her recollection of the trio of BBC, asks, "what do you think?"

"I think it went spectacularly well, and I'm glad you enjoyed so much."

"Oh, I surely did my bitchboi. And I've got just the way to reward you. In a sense."

I knew you had something afoot.

"Let me see your cock, sweetie, I want to unlock you so you can shower."

Doing as told, I pull back the luxurious covers of the master's bed, and you remove your key from between your breasts. Unlocking me, you pull off the shaft of my cage, and I remove the base ring. You hand it all back to me with the instructions to wash myself, my cage, and to shave. Everything.

Everything, by your standards, is from the neck down.

It's a good thing the boat has efficient desalinators, a shower like this takes a while. I settle into the lighted shower stall, and get to work as required, shaving everything I can reach, and rinsing off after soaping twice to remove any leftover hair fragments.

When I get out, I see a note next to a new cage.

"Put this on, and leave your other one on the counter."

This one is different. A plastic material, but with a fine mesh to the cage, so it's easy to rinse through, but I can't touch any portion of my cock. It's also a fair bit smaller than my prior one, in a neutral gray color. It also has a different locking mechanism.

Many chastity cages use a similar lock, a brass cylindrical lock that goes into a hole on the cage, locks in place, and the key is extracted. Very low profile, and secure.

This one is different. This has a plastic piece to fit into the lock bore instead of the usual brass lock, and a plastic numbered tag to go through it. This locks the cage in place, and requires no key to take it off - but if the plastic tag is damaged, it will look like I was trying to take the cage off without permission. It is even more devious than the original, since I COULD get out on my own, but I can't fix the lock, so it's obvious I did so.

You bitch.

(I love it).

Shaved, showered, my nails still fuchsia from our trip to Avalon, I come out from the lav to find you and Elsa waiting. You've picked clothes for me, t-shirt, shorts, Victoria's Secret boyshorts, and a pair of Keen sandals. Pretty much everyday fare for me, and we are all dressed similarly. You and Elsa had showered together in her room, knowing it would take me a while since I was shaving my whole body.

You've switched your purse for a backpack and put a couple of bottles of water in it. "Elsa and I want to reward you for arranging our evening last night, but with a twist. If you keep up with our shopping spree, we'll reward you with unlocking you tonight. If not, then you stay locked in your new cage."

"Mistress, I thought I was supposed to unlock today, since I'd completed my required time."

"Well sweetie," you start...usually a way to chastise me further, "you were unlocked for your shower."

I knew you had something cooking in your devious Mistress mind. Of course, I accepted my fate, and we headed topside for the dock.

Getting coffee at the cart just off the pier, we all begin walking to the east together.

"I wanted to do a little shopping today, and reward you for getting Elsa and I so completely fucked last night. My pussy will be sore for days, and my ass will be too. So," you take a sip, "I wanted to get you a treat, and play a little game with it."

Walking on the sidewalk, we have to change our sequence and cadence periodically for the sake of other pedestrians. I feel like everyone is watching my nail polish, but I try to keep an impassive look behind my Oakleys. At one point you end up out in front of Elsa and I, so she whispers in my ear "play along, it'll be worth it, and I'll help you where I can."

This should be interesting.

We lazily walk about a mile east, finishing our coffee, recycling our cups, and getting into a touristy area of Astoria.

"Oh, this looks nice, let's go in here."

Four Seasons Clothing. A women's clothing store.

We enter, and are greeted by a woman of indeterminate age, somewhere between 30 and 50, and looking great whatever that number may be. "Thank you for coming, I'm Celeste." Celeste had cleavage encouraged with a push up bra, behind a white pinstriped shirt, unbuttoned one more than probably appropriate, but who's counting? That and a black leather skirt which ended well above the knee, sheer black stockings, and heels round out her clothes; immaculately styled blond hair pulled up high, deep red lip gloss, titanium wire framed glasses finish her look. "Is there anything you're looking for specially?"

You respond with a smile and a "not for the moment, we'll just start by looking." The store has a selection of seemingly every style, casual, weekend, business.

"Of course." Celeste withdraws.

You and Elsa ooo and aah at a few things, point out how cute some skirts are (why do women say they're cute when clearly they're HOT?), holding them up to yourselves, each other, and, occasionally, me.

Elsa picks out some yoga pants, and a smart looking button down with a waist tailored just for her shape. You look at a couple of bras you like, and add a pair of hiking shorts similar to what you're wearing. You also hold up a nightie to me, comparing its shape to mine, and add it to the growing stack I'm carrying. Item after item, you hold up to you, or to me; the ones compared to me always lingerie. With a particularly gauzy bra, you comment "I'd love this shape on you, sweetie, but the cups are too big."

Celeste wasn't far away, and sidles up to you, heels clicking on her wooden floor, "We have some other options that might fit better."

I can feel my cheeks turning red.

"Oh, do you? What else do you have?"

With a wink and a finger beckoning us, Celeste says "follow me." She walks past the front door, locks it and puts up the 'closed' sign, then takes us to a side room.

Everything looks similar here. Maybe a bit more elegant, less in the way of shorts and yoga pants. I'm still trying to figure out what's different when Celeste holds up a bra, similar in color and style to what you had, and puts it up to my chest.

It's an A cup.

This room is all for crossdressing men. The shoes along one wall are gorgeous and tall, but sizes are a little bigger than most women wear. The changing rooms have no gender icon on them at all.

"We do have a discerning clientele, some who like a little more personalized service than a chain or department store. We also have some beautiful breast forms that will fill out up to a double D if you'd like to really impress the boys." She winks at me, puts the bra into the stack I'm carrying for you, Elsa, and for myself.

You and Elsa come up behind me and squeeze my ass cheeks. "Sweetie," you start, "I wanted to reward you for having those men take such good care of Elsa and I last night."

I can feel Celeste's expression, a knowing smile crossing her lips. She seems to know what I arranged, asking "did he arrange a visit for you? Did he get to watch?"

You stroke a hand across my shoulder lightly, and move up to speak to Celeste more directly, "Oh, he had an ex-boyfriend of mine, and two of his exceedingly well hung friends, come fuck the two of us silly last night. He was back on board our boat, so he was not allowed to watch."

"Yours is the yacht tied up by the Cannery Pier? Very nice."

"Yes, that's us. We'll be leaving this evening, we're waiting on a crew member change here in town. So we have a few hours before we're due back on board, and I wanted to get him something...fashionable, before we go back."

"We have a variety of options. Was there anything specific you'd like?"

While Elsa and I share a bottle of water on a nearby love seat, the two of you talk through various clothing options for me, discussing varying lengths of skirts, pulling out a variety of shoes in a variety of heel heights, and a similar variety of shirts, minidresses, and stockings with garters. You finally settle on a couple of specific items, but then stand back and gaze at Celeste, "I want him in what you're wearing."

"Oh, that's not hard. We have plenty of options. And with him already being smooth skinned, everything can be tried on nicely."

Celeste moves through the store briskly, taking items matching hers in different sizes, and bringing them to a table for us to see. You approve.

"What do you have in wigs? Anything like your style?"

Smiling again, Celeste opens a closet near the back of this very special room, and selects a styrofoam head, adorned with a blond wig, much like her appearance. The color and texture are quite similar, though the look is down, not up.

"Let's try it on him."

Motioning me to a chair in front of side-lighted mirrors, you have me sit and apply the wig to my scalp. A few movements, plucking here, smoothing there, and it's in place. Celeste asks, "What do you think?"

She slides away from in front of me, and I'm struck by how much I've changed in just a moment. I've not worn wigs in the past, and this is a tremendous change. I look far more...female... than I'd ever considered.

Smiling broadly you say, "I love it. We'll take that, but let's take it off for a few minutes, I'd like to do something."

"Of course, take your time." I think Celeste was running sales numbers in her head.

With me still seated, you come up behind me and wrap your arms around my neck, "Now, bitchboi, I'd like to play a little game. If you lose, you get these lovely clothes to add to your wardrobe, but your poor little cock will stay locked until we get to Juneau. If you win, you get them, and you get to be unlocked tonight, and fuck me any way you like."

Either way I feel like I win...but my cock stirs at the second option, and I'd especially like to win that!

"Well, Mistress, what do you have in mind?"

"Elsa, Celeste and I dress you up, and we walk back to the boat. That's it."

Walk back to the boat. In all girl clothes? That sends my heart to racing, I've never done that before. Yes, in the last several days you've had me run around San Francisco getting made-up, and I've still got the bright fuchsia polish from Avalon which brings looks... but fully dressed up? Getting away with it in San Francisco is one thing... But this is Oregon!

"Remember... You do this and you get whatever you want from me tonight. Any. Thing. You. Want. But if not, your poor little clit can stay locked until we get to Juneau. It's up to you of course. Sweetie." The last word accentuated to chastise me further. With a smile, of course.

Can I pull it off?

Even if I can't, should I try? Because if I do...I get whatever I want from you. And I know just what I want.

With nervous desire and a dry mouth thinking of the idea, I say "let's try it."

You nearly squeal with delight, and call Celeste back in.

"Celeste, we'll take the outfit like yours for sure, but we don't want it in bags...if you understand my meaning."

"Of course I do. I can take the tags off right away."

Elsa is looking for stockings near you as you pick a pair of shoes, asking "Do you have these in a women's 11? That's what he wears." You brandish a pair of super tall black heels, with silver buckles, five inch, peep toe, strappy and oh so sexy.

"Sadly we just sold our last pair of that style in five inch heels this morning, the only thing left like that is three inch."

Didn't I see a pair of 5" as we came in? I thought I had.

"Three inch should do if there's no fives."

With my ensemble assembled, you converge on me. Celeste and Elsa organize clothes, and you bring over your backpack, from which you produce a makeup bag.

You'd had this planned all along.

It's time to get me out of my boy clothes. I stand and begin to walk toward a changing room to strip them off, but you stop me. "Here is fine, sweetie, you can change in front of us. And what a change it will be."

Celeste is the first to comment once I'm down to panties, with a "wow, you do keep him under control don't you? That cage is gorgeous, and so snug."

"Oh yes, I keep his little cock under control all the time," and you pull the key from your cleavage as a demonstration. I may have a plastic tag lock in place, but the key proves your point.

Having me sit back down, you begin instructing me to close eyes, raise forehead, pout and purse lips, as you apply a variety of eye shadow, eye liner, mascara, tone evening cream, and lip gloss with a finishing coat to keep it from wearing. Celeste follows this with the blond wig, then Elsa has me extend a leg for stockings, and then the other. Collectively you stand me up and buckle on my garter, slip on my bra with a pair of convincing C cup breast forms, and finish off the skirt and pinstripe shirt combo.

I'm jittery as hell, but in the mirror I might be able to pull it off.

"How do you feel?" asks Elsa.

"I think I look pretty good, but I'm super nervous."

"Nervous hm? Well, that makes sense. But that gives me an idea, let's give you a girl's name. I vote for Jenny."

You and Celeste second this, and I am dubbed Jenny. Seems to go with my outfit at least.

"Okay, Jenny, let's see you walk," cues Celeste.

Having been used to heels in your presence for some time, I strut a little bit, with a little hip motion thrown in. The woohoos and whoops signal your collective approval.

"I think we're about ready. Just one more thing, Jenny, time to pick out a purse."

I'd never considered this option, so had no idea what to pick. Useful bag big enough to haul a day's worth of stuff? Something that could double as an overnight bag? Something to keep boy clothes in too? Maybe something a little smaller, more stylish?

We look at several options, and I finally settle on a matte-black leather Kate Spade bag with a narrow strap. I tuck my wallet into the purse, my last vestige of 'maleness' in my possession, as you put my boy clothes in your backpack. Celeste puts the other clothes in a couple of bags, my lingerie, stockings, another pair of shoes, minidress, skirt and two shirts in one, your selections and Elsa's in another. I extract my wallet from my purse, and produce a credit card to cover the tab, my bright pink nails contrasting with my black purse. I love the look.

"Thank you for coming in, ladies, and I hope you enjoy the rest of your stay here in Astoria. Please, come back again." Celeste gives each of us girls a peck on the cheek, unlocks the door and opens it for us, turning the sign back to 'open'.

Heart beating quickly, I step out onto the front step, and then to the sidewalk. You two follow.

Elsa comes up beside me with a demure smile, "you look fabulous, and you can totally make it back to the boat. Only the three of us know what's under your skirt...Jenny."

The only way I can pull this off is to look the part. I have to calm down, even if my heart wants to do laps.

With me in the middle, Elsa on my left, and you on my right, we begin walking west, back toward the pier. It's after lunch, and there are more people on the sidewalk.

This is going to be the longest mile of my life.

I keep glancing toward people, but I'm getting fewer looks. A guy with bright pink nails draws some attention, a blond woman in a skirt doesn't. This may be working.

We get a couple of blocks away from the women's clothing store, when you bring up what I'd been too nervous to discuss.

"Are you girls hungry? I'm famished."

Elsa and I agree, and she pulls out her phone. "There's an Indian place about a block away from here on the right." It's already on our side of the street, so I won't have to cross. Well, I'm already crossing, just in a different context.

We enter the restaurant, the pungent scent of curry delicious on our palates as soon as we open the door. It's also, thankfully, dark. I can get away with this I think.

A waitress shows us to a booth, the dining room about ¼ full, and you usher me in first. You sit next to me, and Elsa across from us, backpack, purses and shopping bags next to her. We peruse our menus and come up with selections. I try to sit upright, avoiding the hunch that might give away my true genetics. She returns with water and leaves us for a few minutes to finalize our choice.

Our waitress returns, and Elsa orders for me while I sip my water. She orders a batch of naan for us to snack upon while our various dishes are prepared.

I tear off a piece of the flatbread and take a bite. I realize how awkward I feel as I do so.

Elsa gives me a smile and quietly gives advice, "open your mouth a little wider, and be dainty when you put it in your mouth, that way it won't smear your lipstick." I could swear she had a double meaning to her phrase.

Soon enough I'm getting the hang of it, and I think I'm not so painfully obvious in appearance as I feel inside. Part way through lunch you excuse yourself to the restroom.

Elsa waits until you're out of earshot to tell me "I stashed the size 11 five inch heels. I couldn't see you trying to make it back to the boat on those for a whole mile. I don't think you'd have made it."

I let out a low whistle, and agree. "Thank you for doing that. I don't think I could have without a lot of pain. I can do these three-inch heels, and they're gorgeous too, but five would have been a stretch."

"Besides," Elsa begins, "I want to have some fun with you tonight, and the only way for that to happen is for you to win the bet and make it back to the boat. I didn't get you the other night when Lacy was fucking Brian, and I. Want. You. Tonight."

I had to make it back to the boat. We were halfway there, and had a rest for lunch on the way.

We see you returning, and switch the conversation to the coconut curry Elsa is having, and I take a small taste on her extended fork, carefully so as to avoid smearing my lip gloss.

You sit and eat with us, all of us sharing quiet knowing smiles. Then you ask for Elsa to pass you over your backpack, where you dig in to it, and remove something in the relative darkness of the booth.

"Jenny, I'd like you to go to the bathroom and put this to use." You hand me something in a small cardboard box, long and narrow. You rise from your seat, so I may slide over and stand. I smooth my skirt as I do.

Whispering in my ear, you remind me to use the right bathroom so I don't draw attention. I probably would have made that mistake, having used the men's bathroom my whole life.

The direct path to the dining room has people in it. They're focused on their meals and conversation, but I'm the cock-caged sissy in a skirt walking past them. They're sure to notice, aren't they?

But they don't. I stroll past our dining room companions right to the women's room and push the door to enter.

It strikes me as strange, but makes complete sense - everything is stalls. I'd never considered that, only thinking about men's rooms.

I entered a stall, closed the door and pulled up my skirt. I was used to peeing sitting down since you've had me locked for so long, that was almost normal.

I opened the box. A firm silicone butt plug, brand new, the price tag still covering the opening tab. Sticking a nail through it, I withdrew the plug and inspected it. Not big at all, totally doable...but I had a half mile to get to the pier. At least I was wearing boyshorts and not a thong.

Giving it a healthy dose of saliva, I pull up my skirt a bit further, and, following directions, push the virgin silicone against my ass. With the fucking you've given me on this trip, it slides in without trouble. I relax to the new sensation, then pull up my panties and pull down my skirt. Looking down I make sure my shirt is straight, and then head out of the stall.

That's when I catch the giveaway. Despite my boyshorts' shape, a lump is visible in my crotch. It's my cage, and anyone who takes a look knows I'm not a woman. My best bet is to try to position myself so it's not so prominent, but with a skirt this short my options are limited. I depart the ladies room, back to our table.