The Luncheon

This place was no ordinary restaurant anyhow, I realized as we walked in. It was snugged in among the town's upscale boutiques and featured an obsequious host, white linen tablecloths and napkins, bone china, and a clientele of elegantly dressed women who had paused to chat and refresh themselves while Saturday shopping.

Maureen's long blonde hair was pulled back as always into an impeccable no-nonsense bun, suave as always, as straightforward and simple as her tall, thin body in its free-fall, clinging dress. Just as I'd seen her at occasional receptions also attended by my wife's circle of best friends. The intricate curls in Claudia's short auburn hair betrayed a hairdresser's hand at work perhaps even this morning, a formality that went well with her silk suit and businesslike temper. I was glad Nicole had insisted I re-set my hair carefully this morning before we left the house. "If you want to be accepted as one of us, you've got to look acceptable, it's that simple," Nicole had told me when I'd thought brushing it out would be adequate. "This weekly luncheon is where we all display who we are at our best and catch up on whatever we've been doing. When it's your turn expect to show and tell everything, honey. No shyness, no regrets. Confidently, proudly!"

Maureen looked up as we approached, her eyes flicking over me but settling on Nicole. "Ah, Nicole, there you are! Lauren and Ashley are due any minute, then I guess our little group will be all gathered and we can order. I see you did bring ... is this really you, Courtney? Oh, my, you have changed! What a difference from ... when was it, a month ago at the Bartram's, when you were still ...? I'd never .... I'd heard, but whoever would have thought you'd end up looking so ... so pretty! You really are, Courtney!"

I smiled self-deprecatingly and shrugged and rolled my hips slightly, a gesture of shy denial Nicole had taught me for receiving compliments -- "Pretend you don't believe it but your pussy does and is grateful."

Maureen saw. "And so very ... sexy! Nicole, does this mean that she's been ... has she ... I mean, can we expect ...?"

"Oh yes," my wife replied. "He has quite a story to tell us, I'd say."

"Really!" she said, her eyes fascinated, now looking me up and down much more carefully. I felt comfortable under scrutiny, even a bit smug. I was wearing my lovely Claudia Jones two piece purple confection, a matching skirt and bolero over a ruffled blouse gathered at the neck. Nicole had assured me that with the gold chain she'd loaned me and my large gold ear hoops I looked perfect, sophisticated and smart. And sassy, too, the bolero open to display my beautifully proportioned and somewhat protrusive breasts. The luncheon group had heard all about them but not yet seen them, Nicole reminded me. "Your face may be your fortune from now on," she'd said. "If it's properly made up. But your breasts are any woman's certificate of authenticity, so don't hide them."

"Really!" Maureen repeated as she completed her inspection and flashed me a welcoming smile. "Well, I'm dying to hear all about it! Courtney, I am so delighted you're here at last. We all are. We've heard so much ... you do look lovely. Is that your own hair? Wonderful, you do it yourself? It's very flattering! I love the highlights."

"Thank you," I said in the mellifluous voice Nicole had me using exclusively now. I dipped my head slightly as I spoke, this time to suggest modesty even while again accepting her compliment as my due. Another of the many small gestures I'd learned from my reading in Cosmo and Vogue and even Seventeen, and rehearsed endlessly with Nicole. "Actually, yes to both questions. Nicole had her hairdresser style it for me for easy maintenance -- just a few rollers at night and a comb-out in the morning and here I am!"

"Imagine!" Maureen said thoughtfully, her eyes drifting back to Nicole. "You've done wonders with her, Nicole. I never would have thought .... Do sit down, both of you."

The Maitre d' held out our chairs successively and we sat, me remembering first to set my purse on the table, then to smooth my skirt as I lowered my bottom into the chair. When I looked up I saw Lauren and Ashley entering the restaurant at the far end, the last of our group today, smiling at the manager and gesturing toward us while he nodded. Ashley was wearing the wide-eyed, curly-topped, ditzy blonde look she cultivated these days despite her laid-back smarts, and Lauren's look was like her temperament straight, dark, and truculent. They came toward us holding hands. Nicole had mentioned they'd gotten very close even though they both had husbands.

"If fact they'd love it if their husbands felt for each other what they feel for each other," Nicole told me confidentially one day during one of the many sessions when we'd practiced trading gossip. "Not that they're lesbians or bisexual, more like omnisexual. But they do prefer their own kind, and they don't understand why their husbands don't feel the same way about their kind."

"Really!" I'd responded with an expectant smirk, leaning forward, encouraging Nicole to go on.
Nicole had nodded approvingly. What I'd said and done was just right. Then continued. "On a camping trip not long ago they tricked their guys into sharing the same sleeping bag all night, because that's what they intended to do and what they did, too. By morning theirs was so soaked with their secretions you wouldn't believe it, and they were too. But the boys in their sleeping bag were still as dry and chaste as ever. They'd both had boners half the night and didn't even once reach for their own much less the other's! Didn't even sleep spooned cock into rear end -- they were back to back when Ashley came to wake them. What a waste! Guys simply aren't as affectionate as we are."

I'd agreed that guys were unaccountable. And now I looked forward to hearing more provocative gossip like that. I felt overjoyed. This was Nicole's noon-every-Saturday luncheon, a gathering of her very best friends. I'd envied them that companionability for years, and now I belonged! Or anyhow, would by the time it was over.

It hadn't been easy. After several years of marriage and furtive dressing up I'd finally come out to Nicole. One evening only a few months ago I'd confessed to her that I'd been a crossdresser since boyhood and then sat back terrified, expecting the worst. But the worst never came -- she was far more fascinated than appalled. It seems she understood that kind of thing. She'd had friends with brothers or boyfriends or husbands like me who wanted to be occasional girlfriends. So she was much calmer than I'd anticipated as she questioned me.

I told her no, I hadn't spent a girlhood in the wrong body, only a boyhood, I was a crossdresser not a transsexual. Also, no, I wasn't at all interested in sex with men, I desired women, one in particular, her, and that was why I wanted to look like one, to feel as desirable to myself. No, I didn't want to live as a woman full time, only to dress up and look like one now and then, for the novelty and the excitement of it.

Nicole had nodded, but expressed bafflement. She'd never understood that part of it. Why nibble and not dine? Why not full time? She herself wouldn't want to be a girl any other way. The greatest single pleasure of girlhood, she said, was waking up every morning as a girl and looking forward to doing all the things girls love to do, knowing she'll be doing them every day for weeks and months, her whole lifetime. She couldn't understand 'now and then.' "It's like a quick kiss instead of a whole evening making love and anticipating more evenings into the indefinite future. Like a one night stand instead of a marriage that lasts."

I explained that my ambitions were modest. I enjoyed looking at myself, that was all. I hesitated, then I shamefacedly confessed to her that really, my fondest dream, the height of my ambition as a crossdresser, was merely some day to sit and have lunch in a nice restaurant while dressed as a woman, seated with other women, accepted as a woman by them, looking like one of them and talking with them about whatever it was women talk about when they meet for lunch. To feel that I'm one of the girls. That was all I aspired toward. And even that was only a wish, not a hope or an expectation.

Nicole had been frankly uncomprehending. "You mean like my Saturday luncheon group? You'd actually want to get all gussied and made up just to sit with us for a couple of hours and gossip? For you, that's being a woman?" She'd shaken her head and stared at me.

"Incredible!"

I looked back at her, feeling a little hurt. "It's just a matter of looking the way I love to look and feeling accepted," I said. "Sort of authenticated, maybe. I mean, when people look at you they know who and what you are. Obviously a woman, so that's how they treat you, and so that's how you regard yourself. I'd like the same when that's who I am. Now and then. Not that it'll ever happen."

"I see," she'd said. I wasn't sure she did. "When you're a woman," she added. I couldn't tell if she knew I meant not really.

She nodded her acquiescence when I told her I wanted to try dressing up and looking feminine more often. "No problem," she said. "If that's what pleases you." Though only at home, I stipulated. "Only at home? My husband the wallflower?" she asked in an agreeably teasing tone. "Are you afraid to go into the big, bold, bad world to be seen as a woman? You might feel you'd lowered yourself?"

"I'm afraid to be seen as only a man who wants to look like a woman, that's all. That's a disgrace for a man."

"Why?" she quipped. "Every man should strive to better himself."

Then she looked me over more carefully, intently, almost as if evaluating a candidate for a loan. She may have been doing just that. Then she assured me, "No fear, honey, no one would dream you're a man if you did it right. You have a wonderful bone structure, a small face, a moderate build, and a head full of hair. Why should there ever be a problem?"
I was glad to hear she thought so. But I'd never been able to persuade myself. "We'll see," she said.

The very next Saturday, she saw. She was getting ready to leave the house to join her friends for the weekly luncheon. I happened to enter the bedroom while she was seated at her vanity and bending over to pull up her pantyhose. I loved seeing her do that. It was such a very feminine act. She was wearing the most delicate, frothy slip, and her long straight hair with its gracefully turned ends had fallen over her face. Then as she straightened up she tossed it back, and it fell in perfect order behind her as she looked up at me.

"Now you!" she told me. Was that a twinkle in her eye?

"Now me what, Nicole?" I had no idea what she meant. Toss my hair?

"Now you put on pantyhose. Here's a pair that should fit. Let's see how well you handle something as delicate and sheer as pantyhose. You've done it before, surely."

And she handed me an unopened package, Queen size. Bought for me to test me -- hers were a size smaller. I knew better than to argue.

In fact I welcomed the chance to show her -- years ago I'd passed beyond ruining pantyhose by pulling them up roughly or poking toes through them. Deftly I stripped off my shoes, socks, pants, and shorts, slipped a hand into each pantyhose leg down to the toe, pulled it up, pulled them both onto my legs, and carefully tugged the waist band to its proper place on my midriff.
"You have done that before, haven't you?" she said, looking me over.

I nodded, pleased with myself.

"Though there's poor dickiebird and his two friends squashed against your leg, with no proper place of his own in there and no place to hide."

Without a word I reached down and tucked my cock and balls in between my legs, leaving in view a clear, V shaped crotch like any woman's. Nicole's eyes widened.

"My my," was all she said. Then, "You know, you do have lovely legs, sweetheart. Really! Let's see the rest of this woman you like to resemble. Into the spare room with you, that closet where you keep your stash of clothes, I've seen it, and come out looking feminine while I finish doing my things here. No more than ten minutes, I really have to go!"

This was unexpected, frightening but exhilarating. Without a word I did as she said, raced to the other room, stripped and put on a bra and breast forms, selected a blue-striped stretchy blouse and a plain black pencil skirt and put them on, brushed my hair into fringe bangs, and took just time enough to pencil on eyeliner, smudge shadow on my eyelids, and swipe on a dark lipstick. I slipped into wedgie sandals and clipped on simple button earrings, then returned to our bedroom.

Nicole was now finishing her own make-up, seated at her vanity and applying it with painstaking art. She put down her blush brush and looked at me closely. Analytically this time, as if measuring something.

"This is the best I can do in ten minutes, Nicole," I said in modest apology. "I know I'm not beautiful, but....".

She raised one eyebrow in disbelief and faintly smiled approval -- I'd passed muster somehow, I didn't look like a fool. Then she said, "That's not an issue, honey. You look nice, quite like a girl, not at all manly. You do have a talent. Don't worry about it. But now I am running a little late. Be a pet and get me my black heels out of the closet, would you? I've got to leave this minute."

She finished dusting her cheeks and I did as she asked. But instead of taking the shoes from me, she twisted in her seat, leaned back, and wordlessly put one leg forward. Then the other. I realized what she wanted, knelt down, and slipped each shoe onto her feet.

"Thank you sweetie," she said, standing up and adjusting her skirt. "We'll talk. Bye now!" She waggled her fingers in farewell and left me still kneeling, watching her go out the door.
And that seemed to be that.

Weeks passed. but we didn't really talk. Now and then I'd get home from work first and meet her at the door wearing tight jeans, my cock and balls tucked way under and my smooth crotch declaring that here, unquestionably, was a female vulva. Maybe I'd also wear a T shirt with breastforms for a show of breasts along with light, casual make-up. Now and then I'd wear a skirt and blouse, tailored or pleated, and sometimes a dressy dress with full eye shadow, my hair teased into a semblance of something formal, as if I expected to go out later.
She'd give me her usual happy-to-be-home kiss and then we'd chat and dine, read or watch the tube, as always. She'd always try to compliment me when she thought I'd done something especially nice

-- "Is that a new perfume? I love it!" Or she'd wrinkle her nose when she didn't approve, and sometimes tell me why -- "Never wear a print skirt with a print blouse, honey. One or the other, and then the other plain!" Or "If you don't have a lipstick to match your nails, do please borrow one of mine!" Or "'In' or not, I think visible bra straps are tacky." Otherwise my dressing seemed to be no big deal for her. She gave me two nearly-new dresses culled from her closet as too unfashionable to wear to work. "They're yours if you want them," she said. "If you wore them to work, no one would notice they weren't the latest." I managed a crooked thank you grin, and found that they actually fit me well.

Then three weeks ago everything changed. Three weeks ago she herself raised the subject. It was a Friday evening, and it happened to be an evening when I'd come home from work tired and changed from my suit into men's slacks instead of a skirt. For once I was being myself, a man. It had been a tough week and I was exhausted and didn't have it in me to put on even the minimal make-up I needed to resemble a woman.

Nicole knew I'd been heading a difficult project and that only today I'd brought it in successfully. I met her at the door with a kiss and told her the bosses had been congratulating me all afternoon. She was so pleased for me. "Good!" she said. "I'm so glad! Congratulations, honey. I know it's been an ordeal. Now that it's done, you deserve a real change." Then she'd paused and just stared at me silently for a moment, so I'd know she was serious. Her next words were, "Honey, let's go sit down."

I got worried and quickly moved to the living room couch and sat there on edge. Then instead of sitting next to me she pulled over a straight chair and sat herself facing me. She continued, "It's time. You deserve it. I want you to reward yourself."

"Oh?"

"Yes, oh. You once mentioned that your highest ambition as a crossdresser was to be part of something like my Saturday luncheon circle. To sit with Maureen and Ashley and the rest of us and dish the dirt. Praise whatever one of us has bought recently, and sympathize with whoever's having the usual problems with her husband. Discuss whether to have dessert and decide not to, then spend twenty minutes dividing the check."

"Yes," I said. "I'd love it. But not as a man. Looking like a woman, so I can imagine that's what I am." I had no hope it would ever happen.

"You wouldn't mind all my friends knowing about this ... peculiar habit of yours? Being seen by them in a dress? Sitting there like a lady and gossiping with us all about yourself and all the while they know who you are underneath?"

That was a problem. But there was no way to evade it. I wanted it. "Not if you don't mind," I said, swallowing hard. In fact would I feel embarrassed? Yes. Humiliated? Maybe, certainly if they laughed at me. Could I leave the house and walk the public streets and enter a restaurant pretending to be a proper woman? I'd have to. Was I getting in over my head? Probably.

"That's good. Because last Saturday I told them that's what you want, and we've discussed it, and they see no problem accepting you if you can meet the conditions we've all met. We don't want a man sitting with us, not even an effeminate man. You'd have to look the way we look and share our interests and concerns. Know how women feel about things, some things especially. You'll need to blend in and contribute. And plan to be a regular with us, week after week, not some table-hopper or day-tripper or visitor. Can you do that, do you think? Do you want to?"
I was stunned. Tears came into my eyes. For a moment I couldn't say anything. Then, "Nicole, with all my heart!" was all I could say. "Yes!" I suppressed a sob, then managed to gasp out, "Tomorrow?"

She was moved by my reaction, and took my hand and spoke very gently. "Oh, no, not tomorrow," she said. "You aren't ready. It won't be that easy, baby. But it'll happen just as soon as we can get you ready. I'll tell the girls you've agreed and we'll aim at three weeks from tomorrow."

"Oh!" was all I could say. "Oh, Nicole." I was overwhelmed.

She saw, and finally came over and settled into my lap and kissed me. Then kissed me again, her soft lips on my lips and on each of my eyes. I closed them blissfully. "It'll be hard work, Courtney darling," she said in a low voice. "You'll have to do everything I say, and I mean do it over and over until it's done perfectly, until it's just part of what you are. Everything. No exceptions. And some things I'll ask of you may seem strange, not at all what you want. Difficult. But you'll have to do them anyhow, because I want you to. You have to agree to that right now. I mean it. No exceptions. Everything."

I stared wide-eyed at her, a pang of fear suddenly clutching my stomach, what could she have in mind? But I also felt hope! And mainly I felt transported, elated! Euphoric!

"You'll do everything I ask and be everything I want you to be, and I assure you that three weeks from tomorrow we'll both be seated with the Saturday club, chattering away with the other girls like two old hens."

A distant daydream had suddenly become a reality within reach! I couldn't even speak. "All right," I croaked. "Yes, yes!"