Waiter For A Day

Her voice behind me in line at Starbucks was totally unexpected. "Charley? Charley Botswan, is that you?"

I turned around. The coffee shop was busy. It was situated on the corner of two of the busiest streets in downtown Washington, with streams of pedestrians on both sides of each street, pouring across the intersection on the diagonal then the lights turned green. Large electronic billboards flashed on all sides, this was like our little Times Square. There were a dozen people behind me but it only took a second to spot Christina's smiling face, her hand waving to catch my eye.

It had been a long time. Years. We were quite the hot secret for a few months, and then kids and jobs and other duties intervened, and I moved to another part of town. My career took off, both our marriages took all our attention, and we lost touch. But here she was and man, she still looked good. She was a tiny thing with horn-rimmed glasses, a V-neck sweater, your basic middle-class mom but I knew better. "Wow, Christina," I said, "Let's order and then why don't you come sit with me, we can catch up a little."

I got my latte and found a seat in my favorite corner. There were a couple of thick wooden beams behind the row of chairs, and big picture windows on both sides that looked out over the bustling urban scene. I pulled into a seat and watched some young guys on the sidewalk beating on buckets, a sort of percussion orchestra -- it might be a DC thing. Government guys in ties and jackets, government ladies in heels and fashionable work suits, scraggly-ass hustlers, Chinese chefs, kids ditching school floated past the windows, a sort of aquarium view of the city I live in.

Christina settled in beside me and looked me over. "My god," she said, "Look at you. I wasn't sure it was you at first."

I laughed. "A lot of people say that."

"How much have you lost? That's got to be fifty pounds," she said, with her usual blunt approach.

"Fifty-five, actually," I said.

"Wow," she said again, looking me up and down. She had that same sparkly-eyed quality; life was overflowing in her. Sometimes it got her into trouble but she was so innocently vivacious that she could always talk her way out of things. I had met her husband a few times, and he was, obviously, the most patient man in the world. "How did you do it?" she asked me.

"Huh, what do you think?" I joked. "I didn't eat for a year."

She laughed heartily. "Yeah, that'll do it. No, I mean really. You can't just 'not eat.'"

"A lot of it was attitude, fantasy, picturing myself in a better body."

"I see," she said. "So you pictured yourself like this?"

I was dressed for the office, slacks, dress shirt, tie. I looked down at myself and laughed. "No, not really." See, that's how she is, she gets you off-balance and pretty soon you are partners in some adventure. I knew she wouldn't miss her cue.

"So how did you picture yourself?"

I paused, took a sip of coffee, looked out at the urban aquarium. Christina and I had had a few wild weeks and I know we parted with deep fondness for one another. I knew I could talk to her but honestly I had never discussed this with anyone. Usually it was enough just to explain how I had changed my diet, nobody really wanted to know more.

"Hmm, I don't know if I can explain this," I said. "It's actually kind of embarrassing."

"Oh boy," Christina said cheerfully. "Tell me. I want to hear it all."

"It's not much," I said. "But ... I don't know if I can explain this. A few years ago I read a story, a dumb story. It was about a guy who was skinny-dipping in the ocean and the tide took him out and, wouldn't you know, given the kind of story it was, he was rescued by a yacht full of beautiful women."

Christina rolled her eyes. "God, you haven't changed a bit, have you. Once a pervert, always a pervert."

We sipped our coffee and laughed. It was nice. Christina was firm and petite and friendly, and I felt I could share my secret with her.

"Yeah, right, huh? Well in this story the guy doesn't want to spend all day on the yacht naked, so one of the ladies gives him a little pair of pink panties to wear. And so that's what he wears on the yacht. Of course the women take turns taking advantage of him, you can guess the rest."

"Sure, very imaginative story," she laughed, her eyes sparkling. "Guy rescued by a boatload of horny women. It took a lot to think of that."

"Yes, well," I said, and paused. "It was a dumb story."

"Yeah, so you decided to lose weight because you read a story?"

"Yes, actually, it had a lot to do with it," I said, looking around. Our corner looked out at the street but was private within the bustling coffee shop, blocked by those beams. "The thing was, I pictured myself in some pink panties and, I don't know what to say, it disgusted me. You want to be a sexy kinda paradoxical pervert, attracting all these hot chicks, and when I pictured it I just saw a fat guy, looking ridiculous and pitiful."

"So you decided to change."

"Yes. I bookmarked that story and re-read it every couple of weeks, and I cut down on breakfast and lunch, took one serving for dinner, quit drinking."

"Quit drinking? Wow," she said. "That must have been hard."

"Well I didn't really quit-quit, I just cut back a whole lot. I'd go weeks at a time with no booze. It was not a big deal, nobody even noticed."

She was still looking me up and down. Christina, since you don't know her I'll tell you, was the embodiment of mischief. People live by the rules, they do what they are supposed to do, but for Christina, as long as I'd known her, this just provided a sort of stage-set or background for her, she could dodge in and out of their conformist landscape. People saw her as one of them, a normal little wife and mother, but when they weren't looking she had no boundaries. And a vivid, very active imagination.

"So," she asked. "How did it feel when you finally tried on those panties?"

"Huh?" She had me there. "Oh the panties, I guess I wouldn't even know where to get some. I didn't really want to wear them, that was just a kind of target for me."

"Sure" she said. "I'll tell you what." She pointed out at the row of shops across the street. "Victoria's Secret, lets go, my treat."

"No, no," I insisted. "I don't need anything."

"Well it can be like a trophy for you, an award for losing all this weight. I mean, look at you. You can frame 'em and hang 'em on the wall as a reminder. This is amazing. Come on."

Christina picked up her empty cup and slid off her stool. She held her hand out to me and I took it. Now it was my turn to roll my eyes.

It was stupid, but I had an erection the whole time we were in Victoria's Secret. And let me tell you a secret about fat guys. When I weighed two-twenty-five my dick was about three inches long. Most of it was buried in layers of fat. It would sometimes do this thing where it turns inside out, and I would have to dig it out again with my fingers. When I peed it would splatter all over the floor because the blubber pushed everything into the wrong place. But now I was actually slender, lean, and not exceptionally hung but a little bit on the bigger side of normal. The way I used to be in my twenties. So when I got a hard-on in the lingerie store there was some real pressure in my slacks.

Christina walked me through the bins. My waist was thirty inches now, which is large for a lady. I could not believe all the styles they had. We kept coming back to these little "boyshorts," that were not too tiny, but there was not much fabric there. They were slick silk. Christina, remembering my story, found a pink pair with little ruffles around the edges and a little bow in the front. She told the salesgirl they were for her sister but held them up to me to see how they would fit. She clerk smirked and Christina said, "He's about the same size as her."

"Sure," the salesgirl said, not believing a word of it.

We left the store with a paper bag with the Victoria's Secret logo all over it. I had to go back to work so I threw away the bag and stuffed the panties into my pocket.

"I can hardly wait to see these on you," Christina said.

"I don't see how that will happen," I said. Our affair had been at least six years earlier, and I did not see either one of us trying to start it up again.

"You're not going to come over and model them for me?" she teased.

"No, I don't think that is a good idea."

She took my arm as we walked, just like in the old days. It was fun looking in the shop windows, watching the crazy people of the city. "I've got an idea," she said. "You remember my sisters. Well these days, since mom died and Joey died -- did I tell you my husband died? -- the three sisters have been getting together once a month, we take turns hosting a little lunch. Just the three of us. Sometimes we watch a movie, or play scrabble. Oh and we usually get pretty stoned." She giggled happily.

She continued. "It's at my house this time, next week. And those girls could use a little excitement. Well, I could too. How would like to come over and serve as the waiter for our lunch?"

I looked at her. "Waiter? I don't know anything about waiting tables."

"Well there's only three of us. And you could wear your new panties."

"That's crazy," I said. "I told you, I didn't have a real fantasy about wearing these. I just let you buy them because you were being so nice about it."

She reached up and grabbed my face by the cheeks and turned my face toward her. She gave me a faux-stern look. "Do not lie to me, young man," she said. "I know you. You're a pervert. You'd fucking love this."

"I don't think so."

We were walking past a park with worn-down grass and tired-looking tourists. Christina looked around. "I'll make a deal. If you don't have a hard-on right now then we'll forget it." She reached over nonchalantly with people crowding past us on the sidewalk and took the front of my slacks in her hand and gave my junk a squeeze. Then she smiled up at me. "Okay, good. We'll be at my house Wednesday at eleven. You remember where I live. I think if you get there by a quarter till we'll be okay."

So that is why I ended up taking some time off work and driving to Christina's little brick house in one of the older, cozier neighborhoods of the suburbs. I parked on the street and walked up to the door, wearing my normal-looking work clothes with the pink panties under them. I had worn my regular tighty-whities out of the house and changed in my office, and I would change back later. These panties had been in a bottom drawer of my desk behind some office supplies for the past week.

The door was open and I hollered and Christina called out to come in. She was in jeans and a peasant blouse and the house smelled like good food cooking. The dining room table had places set. Christina was in the kitchen putting together some little sandwiches, with a pot of soup simmering on the stove. "All right, hi," she said, when she saw me. She looked me up and down. "You wearing your new outfit?"

"I am wearing those panties, if that's what you mean."

"Oh yes, that's what I mean," she said. "Come on, let's have a look at them."

I unsnapped my slacks and pulled them down, holding my shirt-tail up. Christina looked at me and laughed. "That's not what I mean," she said. "You know where my room is, you can leave your clothes on the bed."

I went into the bedroom. The fragrance was the same as I remembered, feminine but earthy. I kicked off my shoes, pulled off my socks, and was unbuttoning my shirt when Christina came in. "I want to see," she said.

"Well, can you tell me what is going on here?" I said. "What are you expecting to happen?"

"Oh, sorry. Here's what. You will wear your panties and be our waiter. That's about it."

"Just the panties?"

"Yes," she said as I pulled off my shirt. "I thought about offering you a frilly blouse but actually, seeing you now, I don't think so. Still got that hairy chest huh?"

"Yeah, I'm afraid I'd make a terrible transvestite."

She laughed. "That's fine, you're not a transvestite today, you are a sexy man in pink panties." I unsnapped my pants and pulled them down, standing beside the bed. I could see her eyes widen from across the room. She clapped her hands like a little girl. "Oh, my sisters are going to love this."

"Do they know what you're up to?" I asked her.

"Not really. Well actually, no. Not a clue." I stood here naked, except for some dainty little boyshorts with a neat little bow in front. "Turn around, let me see you." I turned slowly. "That is great. This is beautiful. They will love this." She studied me for a minute. "Tell you what. You stay in here until I call you. They'll be here in a minute. You will be serving drinks and then lunch. It's almost all ready, you will just have to bring it out to us."

"I am getting a bit of a hard-on," I said.

"Excellent." She looked at it. "That's not the way I remember it," she said. "What, did it grow or something?"

"I guess that's part of losing weight," I said.

"Excellent." She came across the room to me and touched my cock with her fingertips. It sprang out against the silky fabric. "Excellent," she said again. "They will love this. Okay, just hang out in here till I call you. Maybe five minutes."

I sat on the bed. My heart was pounding. Only someone like Christina could talk me into something like this. It was innocent enough, really, I am in some little underwear and I bring them their lunch. I had met her sisters years ago but did not know them well. Christina was a redhead, Joan was brunette, and Marcie was blond; their mom had told them that their fathers were the milkman, the postman, and the garbage man. Christina was the youngest and got "garbage man." None of the sisters were bad-looking. Not models or anything, regular middle-class white women who took care of themselves. Actually each one was quite pretty in her way.

Five minutes dragged out, each second being like a day of its own, until finally I heard some voices and the squeak of the door. Then a minute later, more voices. I heard someone say, "So what have you got up your sleeve for us today, Christina?" And the reply, "I engaged a waiter for us." Christina giggled and they all giggled. "A waiter! What is that about?" "He is just going to bring us our drinks and sandwiches and stuff, like a regular waiter," Christina said. "It will be fun." "Fun?" There was suspicion in that voice. "Yeah, it will be fun. It's just a guy I know who offered to help us out. You might remember him, Charley. You might remember we were friends when Joey was still alive." The sisters seemed to vaguely remember. Christina called out, "Charley, come on out here and say hi to my sisters, will you?"

I stood up from the bed. My penis was now soft, my physical state was fear. I was shaking. I saw myself in the mirror and it was even worse, big hairy me in those tiny panties. Well at least I was nice and slender. I turned and looked critically; maybe I looked okay now. It had been a long transition for me, and I was not at the end of the path yet. I still felt like a fat man but the mirror showed a pretty good-looking guy. In little pink panties.

I pushed open the door and stepped into the hallway facing the living room. The three women were standing there. I put a smile on my face and said, "Hello, ladies."

A pin-drop would have been deafening. They froze, except for their eyeballs, which were racing up and down my body, taking in every inch. The brunette one spoke: "That's Charley?"

"Yes," said Christina, with a smile. "Well, he's lost some weight."

The sisters stood there frozen. The blond one said, "And he is our waiter?"

I took the opportunity: "Is there something I can bring you?"

Christina said, "Charley, there is a bottle of chilled white wine on the kitchen counter, and three glasses. Please bring us each a glass of wine." As I turned she was saying, "Come on into the dining room, let's get comfortable."

I didn't trust myself with the tray she had provided so I brought the two sisters' glasses out and then Christina's. They thanked me. "Is there anything else you'd like, Christina?" I asked.

"Oh, today you're the waiter. Call us 'ma'am,' please, if you have to speak. But the less you speak, the better. And no, we don't need anything. How about you stand in that corner right there where we won't have to yell for you."

The drapes were open onto a beautiful sunny day. I stood in the corner next to the window with my hands at my sides. The women sipped their wine but did not talk very much. All three of them sat there staring at me. My cock began to shift a little. The silky fabric only stimulated it more.

"So Christina, you never said much about Charley. I am sure I wouldn't have recognized him," said the blond sister.

"Well it has been a long time. And of course he looks a lot different now."

The brunette asked, "So are you two a, you know?"

"No. I just happened to run into him at Starbucks. Just coincidence. He volunteered to do this, how could I say no?"

"So he's not, like, yours?" a sister asked.

"Oh no," Christina responded. "Today he's all of ours."

"Really?" You could see their minds whirring.

The women began chatting about ordinary things, their kids, neighbors, politics, completely ignoring me while they sipped their wine. When glasses were getting low, the brunette sister Joan -- always the more outgoing one -- said, "Christina, why is Charley all the way over there? Do you think he could sit in my lap for a while?"

The other sisters laughed. Christina said, "Soon enough. First we have to have some lunch. Charley, bring the soup." I yes-ma'amed and complied. And a few minutes later, "Charley, bring the sandwiches." "Yes ma'am." Another round of wine. Then back to my corner. The women ate the dainty little quartered sandwiches and then Joan pulled a big fat joint out of her purse and they passed it around, filling the room with a haze of smoke. They did not offer it to me.

They were chatting among themselves with their eyes consuming me in my corner, when Marcie sort of whispered, "Christina, wasn't he the, uh, 'little' one?"

The women all roared with laughter, especially since Marcie's whisper would have been audible out to the street. When Christina finished laughing she said, "Yes, he was. But you remember he was also the 'heavy' one." The ladies nodded. "Well it looks like his body has changed in more ways than one. Charley, come over here."

I came over with a "Yes, ma'am" and stood in front of Christine. She placed the palm of her hand under my cock and balls and lifted gently. "Didn't this used to be quite a bit smaller?" she asked.

"I guess."

As she touched it, it grew, stretching the panties out. "It wasn't like this, I know," Christina said. "I would have remembered this."

"Let me see," Joan, the brunette, said. "Come here, we've had lunch, come sit on my lap."

Joan was a somewhat plump one with big tits, and I had to scoot up tight against her body so I wouldn't slip off her legs. I put my arm around her shoulders and smiled at her. "There."

"That's better," she said. She took another sip of wine and the conversation resumed as it had been, three sisters catching up on family news after a month. Almost as if she was not thinking about it, Joan's hand dropped to my thigh and rested there. I could feel myself hardening. Then during a round of belly-laughter, her hand settled palm-up under my balls, holding me gently. I grew stiffer. "This is nice," she said to the others. "We ought to have a waiter all the time."

Marcie giggled, "Why didn't I think of that?"

Christina said, "Because you're a big prude, that's why."

"I am not."

"Are too."

Joan in the meantime had begun stroking me, jacking me off gently through the smooth material. "Girls," she said. "Quit it." The oldest sister.