Sailing Away Ch. 17

The Lady Jane pulls into pier 43 on the north side of San Francisco. We're in an interesting area, tourist central with ferries, stores, and vendors, but also with active working ships and shipping activity. We tie up with the assistance of longshoremen, and Brian and Gus idle down the diesels, leaving one generator running.

Knowing we have just a couple of hours, we head for the walkway when you stop me.

"Sweetie, I have a game for us to play today."

"Yes, Mistress?" Elsa's used to it by now, and smiles rather than show surprise.

"We're going to play hide and seek, of sorts. Well, more like capture the flag...but the flag is in motion."

This sounds interesting.

"Elsa and I are going to leave in a moment. We get a 15-minute head start. We will take pictures around San Francisco, and you will try to track us down. We will only stay in each spot a short time after the picture is taken. If you catch us, you can fuck either or both of us any way you want this evening. If not, you get tied to a chair and watch us fuck however we want. But there's a catch - if you don't get us at a location, you'll have to follow directions in the message I send you."

Yep...this sounds... interesting, to say the least.

"Yes ma'am. I'm ready."

"Then the clock starts now. You have no restrictions on how you get around the city. We'll see you later", and you both kiss me before heading down the dock.

I look at my watch and start the 15 minutes. I head into the galley, get a cup of coffee in a to go cup, and back to the deck.

Time to go.

The first picture comes in. The two of you smiling, under the Ghirardelli sign. Okay, that's easy, just a few blocks away from the pier. I head down the walkway, up the dock, and west, headed for the famous chocolatier. I sip my coffee along the way, walking steadily - not racing, nor lagging.

But by the time I get there...you're gone. You had a 15 minute head start. I didn't take more than 10 minutes to get there. But you're gone.

My phone dings, a message arriving.

"Take a picture of your nail polish under the Ghirardelli sign."

Another message follows - "hands and feet both"

It's San Francisco, so I won't get too many stares I bet...but I am in the tourist district on the wharf. But, I dutifully pull my foot out of my Keen sandals, and take a picture of hand and foot, fuchsia nail polish on brilliant display, under the Ghirardelli sign - and press send.

"Good boy."

Another picture comes in. You're standing in front of a fire station, and a pier is in the background. You're posing with a pair of firefighters, quite cute studs of course, in station uniforms. Each of you has a hand on their chest and is making kissing faces toward the camera; someone else is operating it.

I quickly pull open a map app on my phone, and search for a fire station. You're just a few blocks away, Fort Mason fire station. I start walking, and pick up the pace to get there compared to my walk to Ghirardelli.

My phone dings as I walk up in front of the station. You're not on the tarmac. But the message tells me that. "picture of nail polish with fire station behind."

This one's easy...but I'm still falling behind time wise. I send the requisite picture, and wait.

"Good boy. Head west."

I start walking, and soon the next pic comes in. The two of you holding hands, seated on a bench, beige colored pillars behind you.

It's the Palace of Fine Arts dome, right on the lake. That's a few blocks, I better get moving like I mean it.

I arrive, and, as seems to be the pattern, you're not there.

Ding.

"Looks like you just missed us. Go out to the lake at the edge of the dome."

"Take a picture of your panties. Doesn't matter how, but they must be in the picture."

There are tourists around. Great.

I ponder for a moment, and the next picture comes in.

Both of you tongue kissing at the bottom of the Golden Gate, San Francisco side, Elsa's arm holding your phone for the picture.

Only one real place for tourists to go, the park, so I know where you are. But I have to get a move on. I pull the band of my shorts away, set the flash on my iphone, and take a picture down my shorts.

It's not enough, the flash catches my panties, but not enough background. I turn, try again from the side, and have enough to prove I was at the Palace. I rearrange my clothing and head for the street.

A cab. I immediately hail them, and tell them "Golden Gate park, quick as we can!"

It takes us just a few minutes to get there, and he parks as close as he can. I throw $10 to him for a $5 fare, and start looking.

Ding. My shoulders drop.

"Oh, too bad. Just missed us." This text accompanied by a picture. You're on one of the Muni busses, no identifier. Now I'm screwed.

Ding. "Down to the water's edge. Picture of your cage with the golden gate in the background. If you're not hard, it doesn't count, the cage must be full. We're going to stop for lunch...maybe you'll catch up to us."

She's getting serious now.

I briskly walk down to the water's edge. Thankfully it's a weekday, not so many tourists as a weekend. But there are still a few people around. I have to be careful with this one... seeing how it's federal property especially.

I undo my belt, and sit down on a rock to wait and watch... Hopefully undoing the belt gives me some speed in getting my picture. I stroke my cage back and forth, trying to maintain an erection for the picture.

Finally there's a break. I move closer to the water's edge, with nobody around. Unless you count the ships passing under the bridge, but they won't see anything and won't care. I position my phone just right, drop the front of my shorts and tug down my undies, and snap the picture.

I hurriedly put my shorts and belt back into place. As I'm hustling back toward the visitor's center, I get another image on my phone.

Isobune. It's a sushi place in Japan Town, and it's a long way off. I have no idea how to get there by Muni, and no hope of getting there before you leave if I do, so I look for cabs.

No luck. Because it's a weekday, and fewer tourists.

So Uber it is. I put in a request, and in a few minutes, a gray Honda Accord rolls up, with Gwen driving. Gwen gets out to greet me. She's very local - brilliant crimson hair, pierced nose, and gauged ears. A local band adorns her t-shirt. We both hop in.

"Isobune, please - sushi place on the north edge of Japan Town."

"I know right where it is. It's fabulous." She puts the car in gear. "Take us about 15 minutes in this traffic. What brings you to San Francisco?"

"It's a long story, but right now I'm on a bit of a scavenger hunt. Trying to track down my girlfriend and, well her girlfriend."

"Oh that sounds interesting. How are you doing?"

"Well, haven't caught up to them yet. But you're my best bet so far."

Gwen runs the edge of a yellow light. Soon enough we are arriving at Japan Town. I give her 5 stars on the Uber app, and run inside.

Aaaaand...you're not there. Either of you. There's Japanese pop music from the speakers overhead, and 6 Japanese people inside - three of them inside the bar, clearly staff.

One motions over to me, and hands me a message.

It's in your handwriting. "I told them to give the message to the cute boy with the bright pink nail polish. Lunch is attached. Let me know when you get this."

I send a confirmation I'm there, and the chef hands me a pair of sushi rolls on a tiny plate. I eat them quickly with the oh-so American soy sauce and wasabi. I'm about 2/3 through the second one when the next pic comes in.

You're in front of a DSW shoe store. You kissing Elsa's cheek.

How many DSW stores are there in San Francisco? I search and find a handful, then try to narrow down by background. There's also a bookstore behind you, so I search that and find out you're down at Union Square. I take a quick look at a mass transit map, and see I can get a Muni bus down to Union Square with just a few stops. I tip the chef and head out, carrying the last slice of my roll.

Even though it's only a few stops, the Muni seems to take forever. At least it's just $2 to get there, cheapest thing all day besides walking. The stop is just a block south, so I hop off and hustle north.

Of course, as to be expected, you're not there.

Ding. Hooray.

"Go inside, ask for Sarah."

I do as told, entering the store, and asking for Sarah, who comes to the front counter after being paged.

"Hi, I was told to ask for you by Lacy."

"Oh yes. She said the cute boy with bright pink nails would come by. Send her a message that you're here. The confirmation word is 'manolo'."

I text the word to you, and a message returns quickly. "Size 11 women's. 4 inch heel minimum. Peep toe. Sarah takes the picture of you trying them on. Nothing off the sale rack. Hand Sarah your phone, you can have it back after you ring up your purchase."

I just shake my head and hand her my iPhone. She chuckles, reads the message, "come right this way."

I follow along nervously. Ringing up shoes in a small island town is one thing... trying them on in a major metropolitan city is totally amping things up.

She takes me to the appropriate place. I find a pair I like - genuinely - and pick up the box. 4.5", a denim blue color in a lightly textured leather, step in peep toe shoes. Tall, narrow heel.

She has my phone, and I have no way to know the next step without it. I sit down, and open the box up. I look around, a little dejected, and slip them on. The store is not busy, but not barren. Takes a moment to wiggle my feet in, but they do look good. I look up at her to take the picture, hopefully quickly.

"She sent a message. Start walking, she wants a ten second movie recorded."

I'm appalled. Yet have no choice but to comply. I begin my walk, counting slowly, while Sarah films. I give it 5 seconds down the aisle, then turn on my toes, and 5 seconds back. She stops filming and smiles. "Perfect."

I sit, and hurriedly switch shoes back to my sandals. I go to the front of the store, and another message comes in to my phone. I blush.

"He looks so cute in these. Please apply my manager's discount for him."

I read the message and see that this was your request of Sarah, to tell the cashier the same. She hands me back the phone with a smile, and whisper - "she's going to have so much fun with you. And the nails suit you."

I smile back at her, sign the charge on the credit card reader, and take my bag toward the stairs and the street.

Big smiles on your faces, and you point to an icon of American cooking - Williams-Sonoma, home of the copper Kitchen Aid mixer. One of my favorites. The picture has a message attached, "demo kitchen, 3rd floor. Send proof you're there."

Williams-Sonoma is just a half block away! I have a chance! I get down the stairs to ground level quickly, dodge some traffic, and head onto the north side of Union Square. I take the elevator to the third floor, where the huge demonstration kitchens are - both for cooking classes, and designed to inspire equivalent purchases.

I message my confirmation, showing a picture of the huge cooktop facing the main room, backed by a wall of picture windows.

"Go to the picture window and look into Union Square. You must stay at the window until allowed to leave." I play along, and go behind the huge cooktop. Nobody in the room this time of day, no classes running.

I look down. And see the pair of you looking back up at me from the center of Union Square, waving.

I almost want to head for the elevator, but your message was specific. Another one comes in.

"Show us the heels"

Dutifully, I open the bag, dig into the box, and hold them up to the window.

You both make approving gestures, and I see you typing a message into your phone.

"Prove you have on your panties from this morning."

I look behind me, still nobody there. I tug up the edge of my lace thong, so it's visible outside my shorts, and can be seen from the ground.

More approving gestures. Another message.

"Come downstairs to where we are."

I quickly put the box back together and head for the elevator. Three floors never seemed so far away. Leaving the front door, I cross into Union Square...to find you gone.

Ding.

I can't believe this.

It's a picture of you two in front of the MAC cosmetics store. I quickly google a location, and it's just around the corner. I may still have a chance!

I head southeast, then down the block, I can see the store as I clear the square.

I enter. You're not there. How the fuck did you go so fast?

Ding.

"Ask for Michelle."

Doing as I'm told, I ask at the front. The girl at the desk calls for Michelle. She's gorgeous. Long black hair, very straight, perhaps half Japanese and about 5'4"...before the black stiletto heels at 4". Her heels click as she comes to the front. She shakes my hand. Confidence emanates from her. Or is that dominance?

"She said you'd be here in a few minutes. Your phone please." She smiles, but is clearly comfortable with this role.

I hand it over, and she sends a message confirming my arrival. A return message comes in saying "follow her." She shows it to me, I shrug my shoulders, and follow her to a back counter.

Another message comes in. "Pick two lip glosses, two eyeliners, two eye shadows. Nothing random, they must go together and be approved by Michelle."

I'm still wondering how you got here in the couple of minutes it took me from Williams Sonoma AND then got away. But I follow directions, picking a subdued look (brown eyeliner, a subtle pink gloss, and a subtle brown eye shadow), and a bolder look (purplish shadow, contrasting deep red gloss, and a dark eyeliner).

Michelle types a message on my phone, and takes a picture of what I've picked. A return message arrives, and she nods her head, then hands me the phone.

"One of each. Your choice. Applied by Michelle. Send proof, then you may leave."

I quickly take the subtle set, and hand them over. She sits me in a chair and quite expertly applies everything. I'm glad it's subtle. It looks good, I actually quite like the look, and it won't draw too much attention when I leave. Michelle sets my phone for a picture, "smile for the camera." I do so, she snaps a picture, and sends it to you. The message comes back quickly, "pay your bill, and go outside."

I do as told, and as I'm leaving, get a message.

Wow.

Elsa is naked standing behind you. Your tits look miraculously good. That's because she's lacing you into a blue and white leather corset. You're already wearing knee high leather boots, black. No panties, you're naked from corset to boots. A woman is in the background giving Elsa some guidance, she's in a blood red corset and matching flowing skirt, dark hair pulled back, not too tightly. This also means someone else is taking the picture, and I can see the window in the background.

Stormy Leather. One of the best leather clothing stores in the US.

The only text - "ask for Hannah"

Traffic is too dense on this street, so I head south to Market Street, just a block and a half, and hail a cab.

"Stormy Leather, please."

The guy behind the wheel nods, pushes a button switching to a Spanish language channel, and trips the meter.

I'm not obvious. Oh no, not me. DSW shoes bag, MAC Cosmetics bag, lip gloss, eyeliner, and bright fuchsia nail polish. I'd be more subdued as a local pro football player.

I wait. No messages. It's about 15 minutes, and I drop a $5 tip onto the fare, and hop out to the curb side.

I enter, and as I'm about to ask, the woman in red comes to me with a big smile and extends her hand, "Hi, I'm Hannah."

"Hello, Hannah. Did she tell you what's going on?"

"In a manner of speaking. Your phone please."

I hand it over as I have before, and she types a message, presumably confirming my arrival. A message comes in, "pick one of her collection, then check in."

This sounds easy enough. One of the easier parts today. But the bags are getting a little bulky.

Hannah shows me a handful of cock rings, all leather. I select one, small snaps, smooth surface, no studs. I send the message as required.

"Hannah puts it on, and I get a picture of it. Then pay the tab and await the next picture."

Okay, now I'm a little more nervous. This means Hannah sees my panties, and my cage.

I hand her the phone for proof. "Oh, I knew that was coming, honey. Come in back."

I follow along, until she stops me. "Okay, drop your shorts. Let me see."

I'm blushing, I know I am. But my polished fingers work my belt, button, and zipper, and I let my shorts fall to the floor.

"Oh, it's a holy trainer. Those cages are great. Two of my boys are in them right now. Let's just add to this, so you can be on your way, shall we? Pull your panties down."

I do as I'm instructed, and she hands the phone back for a picture. I'm shaky, but manage to get my phone steady enough for the requisite picture. I close up on her hands snapping the strap around the base of my cock and cage. I show it to her for approval, as I'm not sure she wants her face in it.

"Sweetie, take another, I can use this for marketing."

I snap another, with her calmly adding further restraint to the cock straining against its cage. I show it to her, she nods with approval, "get dressed."

Pulling everything up, I feel the extra pressure of the leather on my cage. It's like a hand grasping and holding on but not moving. Almost like you're trying to ruin an orgasm for me.

Heavenly.

I go to the front and pull out my credit card. She adds the price of my cage to a tally on another sheet, and hands me a receipt.

It's a little surprising, so I gulp, then sign it. Apparently I just bought you the boots and corset in the picture, PLUS my cockring.

I send a picture of the receipt to prove I'm done, and you immediately reply with a picture of a massive, inexplicably large dildo. You're holding it in your hands, making a faux gasping expression. Mr. S is in the background.

It's not far. I walk. I haven't won yet. I probably won't. And I'm already about as obvious as I can get with leather, cosmetics, shoes, and the like in bags. You're not there either.

As soon as I walk in, it's obvious I was expected. A cute, but very butch girl is behind the counter, and chuckles. "Oh, she has done you in today hasn't she? Come over here, I'll help." She's about 5'6", small tits, one arm a full tattoo sleeve. Hair buzzed to almost nothing. I approach the counter, and she reaches to take my bags.

My phone dings. Again.

"Hand her the phone."

I frustratedly do so. She sends a message, and another one replies. She sends another, and a back and forth starts. "By the way, I'm Ashley." Her short black nails contrast her smile, and suit her perfectly.

"I think we've worked something out."

"I don't understand."

"Honey, I think you've had enough today. You look frustrated, tired, and run ragged - even with the nails and makeup, which look great on you I must add. Your mistress had plans for you here, but I think I've talked her out of them. She seems to understand."

"What did she have in mind," I query.

"That's not necessarily important. And probably best to leave that way. Just leave your bags here, and come with me, I'll show you what she wants." She reaches a hand out for me, clasping mine in hers, and I follow. She looks tough, but is very gentle.

"She was going to want you to try something on for size here, so to speak. But you've had enough. Instead, you just get to pick something out." She shows me the butt plug selection.

It's somewhat astonishing what gay men will play with. Some of these are mindbogglingly large, some big enough to be downright scary. Much like the one in your picture. Ashley points to a range, saying "she wants something in this size, but you can pick." They are all larger than any plug I currently have...but the smaller end of that range is nearly the same, so it's not eye watering. I select a matte blue silicone one with lumps on it, almost like beads.