Rick's Embarrassing Adventures Ch. 04

Chapter Four--A Humiliating Shopping Trip

It took about half an hour to drive to the mall Rachel had selected. As with my trip to her house, no one seemed to notice me sitting in the car wearing a bra under my t-shirt. Initially, there was no conversation between us. The car was quiet, and Rachel was busy navigating the roads to the outer loop interstate she wanted. This took only about ten minutes of the trip.

Once we were on the highway, she asked, "Are you excited?"

I thought about it. "Yes, ma'am. I'm excited. I'm also scared. I'm realizing that you're going to parade me through this mall and into shops." It was true. I was thinking about that and feeling very uneasy about what could happen: the stares, the smirks, the laughter, and even the ridicule I might be in for.

"That's absolutely right, Rick. And you are going to act like this is a normal part of your life. For the next month, it will be a normal part of your life to be exposed in this fashion to the reactions of others. I don't want any holding back on your part. This is what you asked for. I'm looking forward to taking you to some stores that should be able to fit you in some decent, or indecent, clothes.

"When I park, you are to get out and follow me into the mall and into any shops I choose to enter. You will stay with me at all times unless I turn you over to one of the shop assistants. If one of them will see you alone, you will go with her for your fitting, and you will do whatever she tells you to do as if I were telling you. If anyone doesn't want to work with us on your clothes, we will leave together and find another store. But you will always smile and be polite and courteous."

"Yes, ma'am. Thank you, ma'am." This was going to be awful. I just knew it would be. Just as I knew that I was rock hard with no foreseeable way to calm myself down. I just hoped any of the helpers I was given over to would not scream at the sight of a hard cock.

Rachel parked at a center door of one of the largest malls in the area, one that had three huge anchor stores and dozens of smaller establishments in between. We got out, and she locked the car while I scanned around to see who was noticing.

"Come along, boy," she said as she started for the door. I scurried to catch up. We made a disparate pair: she was dressed like a respectable woman in light blouse, beige skirt, hose, and sensible but fashionable shoes. I looked like ... I'm not sure; I think an aging dyke, at least from a distance. Up close, I'm sure I looked like a poor excuse for a transvestite. No self-respecting cross-dressing man would look like so incompletely transformed.

She stopped at the door, and I knew it was for me to open for her, which I did. She breezed past me to stop at one of those large information maps, which she proceeded to study as if looking intently for the way to her destination. I suspected she was just showing me off, and I fully expected to be slow-walked the length of this place and back, as well as stopping at as many places as she wanted to stop.

Meanwhile, I had to stand by her side as if everything was normal. There were people around, walking to and from their cars or going in or out of the small shops in this entrance area of the mall. There was a games arcade with younger people congregating around it, and across the way there was an ice cream shop that sold cones and shakes and such. Many people of various ages and no one seemed to have noticed me at all.

Wait, there was a woman of about thirty. I saw her casual glance, then I saw the double-take look. Our eyes met, and she looked away as if ashamed for looking. That was a surprise. Was she embarrassed for me? Or was she embarrassed that I saw her looking?

Yet aside from her momentary reaction, I was getting nothing. From a distance, no one seemed to see anything out of the ordinary. I was relieved.

Then, to my surprise, I felt disappointed. I had feared just this situation of being out in public and being ridiculed for my attire. Now I wasn't getting more than the occasional, well rare actually, second glance. It felt like a come down, a big time downer.

"Rick, come with me." Rachel's voice brought me out of my reverie and back to the reality that Rachel was going to embarrass me here, and it had been my idea.

I moved to catch up with her. "Yes, ma'am. Thank you, ma'am." She surprised me with her walking speed. I had expected a long drawn out leisurely stroll, but Rachel was moving with purpose toward a specific destination.

About halfway down the center corridor of the mall, we came to the place Rachel was looking for, a fair sized women's clothing store advertising "Fashions For the Full Figured Woman." At 6' 1" and 210 lbs., I think I'm an average size American male, but I guess that would make me more of a large woman than otherwise. So the choice made sense. I would soon find out how people here would feel about me being here. I didn't even have to guess that this would be embarrassing.

Rachel made straight for the lingerie desk. We had to pass most of the displays for bras, panties, slips, and such. Mostly I saw light shades: white, beige, light blue, but there were some bright colors, too.

"Anna," Rachel said to the plump woman behind the counter, "How's business?"

Anna had been watching us approach, and I thought I saw the hint of a smile on a rather pleasant face. She was wearing a nicely styled blue business suit, no doubt from the store's stock, and she had an ample bosom to hold up her nameplate that identified her. But it was obvious to me that Rachel knew her.

"I can't complain, Rachel honey." Anna had a rather brassy voice that carried easily. "Well, I could complain, but who would listen?" Then in a louder voice, "Is this the gentleman you were telling me about this morning?"

Uh oh. They had this setup already. I felt myself blush and my cock stir.

"Yes. Anna, this is Rick. He needs some bras and panties that fit him appropriately. As you can see, he fancies himself well-endowed in the rack."

Anna looked me up and down slowly. "Yes, I can see that." She pointed at her own bosom. "I'm sure we can find some items that will work. And you say he wants to be embarrassed as we do this?" The way her voice carried, I wished I could just melt into the floor. There were other customers in the store on this Saturday afternoon, and I was sure they were looking our way now even though I dared not look. I tried to smile sheepishly through my increasing blush. I was feeling hot, blushing so much.

Rachel smiled at both of us. "Yes, that would add to his enjoyment..and mine. I'm finding I like his coloring."

Anna came around the counter chuckling to herself. "Rachel, you wouldn't believe the men who come in here 'shopping for their wives'," she added air quotes. They blush so nicely. Funny that all of them have 'wives' who are about their size in the chest." She turned me to face her directly, staring into my eyes. I tried to stare back, but broke easily. "Does he have a special name for this excursion?"

"Special name?" Rachel asked. I stayed silent.

"Yes, many of our male clients have female names for when they're playing dress up. Oh, and I forgot to ask, are we doing a full outfit or just the under garments?"

Rachel thought for a bit. "No, Rick is a different case, I believe. He doesn't want to dress as a woman completely. He just wants to look like a guy wearing a bra in public. It turns him on. I suppose we could call him 'boy' while he's here so there's no confusion about what he is."

Anna nodded. "Okay, boy it is." Then to me, "So, boy, what are you?"

"Ma'am?" I wasn't sure what she wanted me to say.

"Well, are you a slut boy who can't say no? A queen? A tease? How do you see yourself at this moment? It makes a difference how I dress you."

How did I want to describe myself? I hadn't considered that. After thinking for a bit, I turned to Rachel. "Ma'am, how would you describe me? I think that would be most appropriate, if you agree." Rachel smiled. "Very good answer, Rick. Anna, he's a slut boy who can't say no."

"Oooh, good," Anna said, clapping her hands. "I like slut boys who can't say no." She turned to Rachel with her own version of the wicked smile. "Does that apply to me?"

"Of course, dear Anna. I can't expect special service without offering an appropriate gratuity."

Oh shit, I thought. I was going to be servicing Anna, at least. And here in the store, no doubt. But before that, I was going to be very embarrassed. Oh, God, what have I gotten myself into?

Anna turned back to me. "Okay, slut boy Rick, let's see what I have to work with. Take off your shirt."

I was aghast. I thought I would do that in a fitting room. "Here?" I said, in a most unsubmissive way.

Anna took a step back, surprised by the loudness of my voice. Rachel stepped in. "Who are you to question anything? You agreed to do whatever I or anyone else said. You will NOT embarrass me. You WILL do as you are told, or else, and you know what that means."

I hung my head in shame and embarrassment. It didn't seem possible, but I had just made my situation worse. Just how much worse I didn't yet know.

"I'm sorry, ma'am. I lost my head."

"You don't HAVE a head," Rachel said. She was righteously furious with me. "Now get on your knees and apologize to my friend here. Then do as you are told."

"Yes, ma'am. Thank you, ma'am." I knelt before Anna and looked up at the woman towering above me.

"I'm sorry, ma'am." I started to take off my t-shirt. Anna stopped me.

"Stand up, slut boy. Now sit up on this counter facing out at the store."

I climbed up on the counter and faced out toward the store. Damn, I had attracted a crowd or curious onlookers.

"Now take off your shirt."

All eyes were on me as I pulled my shirt over my head, revealing my stuffed blue bra for all to see. Even before I got the shirt all the way over my head, I heard the applause and the laughter. I was mortified. I didn't think it could get any worse, when it did.

Rachel stepped forward. "For being disrespectful, you will now stand on the counter and take off your shorts."

I could feel my jaw drop. I thought I might pass out, but I got myself together quickly and said, "Yes, ma'am. Thank you, ma'am. I'm sorry, ma'am," as I scrambled to my feet on top of the counter for all to see.

The applause rose once again. I turned and began tugging my bike shorts down, stopping a couple of times to keep the panties from coming down with them. The applause turned to cheers and raucous comments from the various women in the shop. I could also see people coming in from the mall to see what all the shouting was about. There I stood in my deep blue bra and matching panties with my shorts around my feet. Oh, and of course my cock was poking my panties out obscenely. Everything was in play.

Rachel hollered at me above the crowd noise. "Smile and wave to the crowd, slut boy. Enjoy your humiliation."

I did as I was told. That's when I saw the camera flashes from all around as everyone wanted to be the first to post my shame to the Internet. Well, I may have just screwed myself over royally, and I had no one to blame but myself. As I stood there waving like a idiot, I resolved to keep my mouth shut unless it was required to be open.

Somewhere between two minutes and a week later, I was allowed to climb down from my perch. Anna turned to the crowd and said, "Show's over, folks. Hope you enjoyed it. Feel free to look around, but no more picture, okay?" She turned to Rachel. "I hadn't expected all of that. I hope it doesn't screw up your plans."

Rachel hugged the larger woman. "Oh, Anna, I couldn't have asked for more. He tried to embarrass both of us. He deserved what he got."

I stood silently as the women embraced. Women were wandering the racks close by, actually sneaking a look at me, but there were no more pictures. Well, I don't know that, but I didn't see any more flashes.

"Now," said Anna turning back to me, "Let's take a look at what we have to work with. Stand up straight and proud, slut boy. We should always be proud of how we look." I straightened my shoulders. "That's better."

She began examining my bra, turning me this way and that and away from her, slipping her fingers between the fabric and my skin. All the while, she was either tsking or shaking her head.

Finally, she turned me back to face her and Rachel. "Typical male. Even though it's a C-cup, it's too tight, both around the torso and in the shoulders. The shoulders are easy to fix, but it takes an extender to fix the other problem, and I hate to waste good extenders on such crummy fabric. I do like the color, though. It shows a little more imagination than the average male, whose tastes seem to run only to red or occasionally black. And the socks! Goodness men are so unimaginative." Of course, the socks were Rachel's doing, but I couldn't have done better. Besides, I knew this was a good time to be quiet and take it.

"But you can take care of him?" Rachel asked. She didn't really seem to doubt it, though.

"You know I can, dear. One question: Are you going to get him breast forms? You really should. Nothing fills cups out better if you don't really have the goods."

"That's why I came to you, Anna. I knew you'd know the best approach. I suppose I can get them on the Internet?"

"Yes, you can do that, if you want. But I sell them, you know. Come, let me show you."

They went behind the counter. Anna said, "I keep this section back here mostly for our ladies who have had mastectomies. It's so hard for them to get fitted properly after their surgeries, and even though the medical people will give them something I find I can help many of them with something of a higher quality than they might otherwise get.

"That's especially true of us fuller figured types." Anna turned her head to look at me, then turned back to Rachel. "Honey, I've got a set that will be perfect for what you want to do to your slut boy, here." She moved to whisper in Rachel's ear. I saw Rachel's eyes go wide, and I knew I didn't like it (and would no doubt love the humiliation of it).

"Yes!" cried Rachel. "That's perfect. I'll need six bras and matching panties. He'll try on each to make sure you're satisfied with fit and finish."

Anna smiled. "Take him to the room behind this wall. I'll bring your stuff to you, shortly." Before she left, she handed Rachel a rather large box. Rachel walked along the wall, and I followed, grabbing my shirt and shorts. I followed her through a curtain into a small room with a bench and a hanger for clothes along one wall and full-length wall mirrors on the other two wall, so one could see oneself front and side without doing more than turning the head. Despite the mirrors, in which I could not avoid seeing myself, I felt relieved to be out of the public eye.

"Toss your clothes over there and strip." As I did what she wanted, quickly being completely nude except for shoes (somehow that felt more humiliating than being barefoot. Meanwhile, Rachel opened the box, took out two large breast forms and what had to be an instruction sheet. As I stood near one of the mirrored walls, she read the sheet front and back. Then she looked back into the box and took out a tube of something.

"I think you're going to want to shave after we get back to the house. This adhesive will take some hair off when these come off for the night."

"Yes, ma'am. Thank you, ma'am," I said, automatically. I was looking at the forms. They were huge! Double D's at least. Geez but I was going to have a rack on me.

Rachel came over and applied the adhesive liberally. "With all that hair, I need to make sure your tits will stick." Then she very carefully lined up a breast form and pressed it on my left breast, holding it firmly and counting silently. she stepped back to look. Apparently satisfied, she did the same on the right, and stepped back again to admire her handiwork.

"Face the mirror," she indicated the one to my left, "And look at your new boobs."

I was amazed. If you didn't pay attention to the hair around the rest of my chest, they looked real; they even had nipples with brown aureola. Despite my predicament, I was impressed. And they were still huge!

"Anna thought that since you liked having a large pair, you should have an obscenely large pair." She looked down. "I can see that little ricki likes them, too." She grinned up at me. "Now somebody could fuck your tits and cum on your face." That thought made me burn with humiliation.

"You've really gotten into this."

"Rick, I'm having more fun than I thought I would. Those stories really got me going, and I realized you wanted to be the 'slut boy who couldn't say no.' So I thought I'd go for it and see how much I liked it. And I'm loving it!" Her face turned serious. "I'm having so much fun, I have to ask if this is meeting your expectations. This is a serious question. You've had an awful lot. Is it too much?"

"Ma'am, is this a trick question?"

"No, Rick. But your answer might modify some of my wilder thinking. Do you want it toned down, or am I meeting your needs."

"Gawd, I've never been so embarrassed in my life. Not even in my wildest dreams. But...but...no, dammit. I want your full treatment. Look at little ricki. I've been hard all day, well mostly. And I'm so horny I could probably shoot a quart!" I paused to take a breath. I knew I was speaking the truth. I am a slut who craves this, and I didn't want it to stop. "Thank you, ma'am."

Anna came bustling in at that moment and stopped dead in the curtain. "Well done, Rachel. That's one impressive set you got there. That should have him blushing for a long time. And that's not a bad looking pecker there, If I may say so. Is he any good with it?"

"He's quite good," Rachel assured her. "In fact, for a man with this sort of hang up, he's surprisingly good." (What the hell did that mean? I wondered, as my cock bobbed and my blush colored my neck and the top of my chest.)

Anna dumped her load of lingerie on the bench. "Well, there's no accounting for taste, I always say. Now, where shall we start?"

They spent the next half hour trying on every set of lingerie, Anna brought, all six of them. All of the bras fit, and even though I was now much better endowed than I could ever have imagined, I had to admit that the bras felt more comfortable than what I had bought on the Internet.

The panties were not so much fun because I kept poking out. Rachel made crude comments about how I would be arrested for indecent exposure if I walked around with my dick sticking out, which only served to further embarrass, and harden, me. I was remembering my instructions for when I came to her house for the next month. Anna thought it was all hilarious, which further embarrassed me.

Eventually, they had worked their way through all six sets. I ended up wearing a hot pink set that look ridiculous on a man in his fifties with a slight paunch. Looking at myself in the mirror, I watched my cock shrivel. Perhaps I had gotten used to the situation and was no longer turned on by it. Perhaps I was used to them and their comments. Whatever the case, I tucked that once proud bit of flesh into my panties.

"Well, Anna, I guess my slut boy is getting tired. Would you like your gratuity now?" We all knew what she meant.

"Rachel, I do admit I'm more than a bit keyed up, but I've been away from the store proper just about as long as I dare. Can I take a rain check?"

"Of course you can. Maybe you can swing by the house tonight?"

"I don't know, Rachel. I'm usually dog tired by the end of the day, and I have to open tomorrow. No rest for the wicked."

"Well, anytime you want to get some relief, I'll make Rick available." I felt numb to this talk by now. Rachel turned to me. "Get your shirt and shorts, but don't put them on till we pay." She grabbed the other new sets while I got dressed and picked up my blue bra and panties and Rachel's socks. Then we followed Anna back out into the main store and to the desk where we first met her.