Girls' Night Out - Cover

Girls' Night Out

Copyright© 1999 by Vickie Tern

Chapter 1

Erotica Sex Story: Chapter 1 - A man dresses as a woman for his wife.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/Ma   Consensual   TransGender  

"So, I see she did talk you into it! My God, look at you! You're gorgeous!"

There at the door was Pearl, my wife's best friend, looking at me as I figured she would when she saw me, amused but also contemptuous. She stepped back and gave me that same relentless look of appraisal women use on themselves when they look into mirrors. Then she said, "Not bad! Not too bad! But how in the world did she get you to do it?"

I was embarrassed, but tried to hide it. So I looked Pearl over equally deliberately. What I saw was the usual bright and brassy middle aged woman, dressed up for a big night out on the town. Packed into a green silk dress much too short for her, I thought. Matching strappy high heels and a clutch purse. Lacy black stockings. Pinned somewhere back of her blonde curls was some kind of small felt hat with a wisp of black veil. So she was green and black and lacy and sassy, and busy making me feel uncomfortable.

"C'mon in, Pearl," I said. "Bea's almost ready. You look good too, you really do!"

I was sincere -- for Pearl, she looked terrific. But especially I wanted to steer our conversation into compliments right away. I couldn't take her usual mockery, her sardonic put-downs. Not dressed the way I was when I came to the door. I was trying not to be too self-conscious about it. I wanted to be a good sport for this one night, to play it straight. To be a proper lady, one of the girls, the way I'd promised Bea. But with Pearl nothing ever comes easy.

She overreacted like a Disney cartoon character. Her eyes flicked over my coiffure and then down my dress, Bea's choice for me for the evening, a little basic black with satin trim, and a cute peplum to hide my lack of hips, and a wide satin-trimmed collar to cover my now-noticeable breasts. Then she eyeballed my legs -- in plain sheer black stockings, nothing fancy -- and my high heeled black pumps. "Wow!" she said, wiping an imaginary haze from in front of her eyes. Her skirt flipped and she wriggled her hips, then planted her hands on them. "Hoo boy!" she said. "Aren't you something!" She squared her body and then gave me her ultimate once-over. I'd seen it before. Insolent and amused. Absolutely intimidating. In that posture she looked like a tart naming her price, take it or leave it, but managed to imply that I was the tart. "Henry, I don't know what to say. You're such a stunner! You'll knock 'em dead! How can you stand yourself?"

Her irony was too heavy, and I began to wilt. But Pearl sensed it and immediately reversed field. She said, "No, really, I mean it! I'm impressed! That makeover is fabulous! You're really convincing! They must have spent the whole day working on you!"

"Thanks," I said, "If that was a compliment. Come in and sit down."

She stepped into the hallway like a dainty horse imprinting the ground, glanced at me again, and then let her high heels throw her hips into a seductive swish as she proceeded ahead of me into the living room. I got her message. I had to admit it, I couldn't have looked more swishy. "Yes," she said, "It was a compliment. A pretty girl should learn to accept compliments graciously. Just dimple, and curtsy, and say 'Thank you.' You know, when a girl spends hours or days getting ready for a big date, she should appreciate it when her efforts are noticed."

"Bea told me you'd agreed to be one of the girls tonight, but I just didn't believe her." Pearl went on. She sat down, and carefully arranged her legs on our living room couch, skirt smooth, arms draped possessively across the back cushions, at her ease. "Frankly, Henry, I didn't think you had the guts. No offense. But how many men do you know would do this for their wives?"

I followed Pearl into the living room, rocking a bit on my own high heels, and stood looking down at her. She arched her neck up and said, "Get me a drink, would you, Honey? I'd better start calling you 'Honey' I think, not 'Henry.' A 'Henry' who looks the way you do will start people talking, and I'm not sure you'd want to hear what they were saying."

"Or am I looking at 'Henrietta, ' Henry's longtime girly other self? Have I at last found out your guilty secret? Have you always liked dressing up in frilly things? Do you really want to be a girl? Have a stiff drink yourself, hon. You're going to need it before tonight's through!"

I took her advice, belted down a quick one, poured Pearl her usual whiskey on rocks and myself another, handed it to her, then sat down across from her. I clasped my drink in my lap with both hands, and crossed my ankles primly, just as Bea had shown me. Shoulders back, bust out, chin high, shake my curls to get her attention, then speak in a high but sweet voice, if I could manage it.

"Don't, Pearl," I said. There was just a touch of pleading in my voice, for Pearl usually a signal to lunge in for the kill. I had better be more aggressive. "You know perfectly well that Bea has been getting me ready for tonight for months. In fact, what with her planning and shopping and rehearsing me, she's had very little else on her mind for some time. I've never seen her like this, not in all our twenty years of marriage. She's been so happy and busy. So don't mock me, because when you do, you're mocking Bea. And that's not friendly." My voice quavered just a little. Maybe it was pitched too high.

"All right, Honey," Pearl said, her voice softened but not subdued. "I'll be gentle. You're one of the girls tonight, and that's that. Don't cry, you'll ruin your beautiful eyes." This time she looked at my face seriously. "They really are beautiful, in a way. Who would have thought it?"

I felt a little mollified. "Well, Bea always did. Even before I was involved in this."

Pearl's look was unwavering. "All right, Bea thinks you're beautiful. But tell me, my Honey, my lamb led to the slaughter. Whatever possessed you? Why are you involved, as you see it? I know, but I'm curious what you know. Tell me what you think is going on."

Pearl didn't seem to be taking this night seriously enough, so I opened up. It was a chance for me to practice my voice some more, anyhow.

"You know full well how come I'm involved. Bea's had her heart set on tonight since last year. You know that. In fact, it was your own idea originally. You remember, Bea's thirty-ninth birthday? How it hit her? Like a house collapsing on her? All that weeping, she was getting old and ugly, life was passing her by. Every day more depressed, popping more pills, then feeling even more miserable. Some days she didn't even bother to get dressed, and I was really worried. Then when I'd try to talk to her, to cheer her up, she'd just look at me and withdraw even further, run into the bedroom or the bathroom and then cry her heart out."

"I remember that time," Pearl said, looking me levelly in the eyes. "It was exactly a year ago."

"So I offered to organize a big party for her to help her celebrate her fortieth when it came around. Invite everyone we knew. Well, that was certainly a mistake! She absolutely forbade it! She ran into the bedroom and slammed the door, and then she really started wailing! I mean loud, agonized, despairing, just terrible! I felt awful! I still don't understand it."

"I know about that time too," Pearl said, still looking at me steadily, and taking little sips from her glass. I remembered to do the same -- sips, not swallows, it's much more ladylike, Bea had told me. It felt more delicate. I wondered if my lipstick was smeared. "You missed the point, Honey dear!," Pearl went on. "A forty year old woman doesn't feel like celebrating. It isn't like a man turning forty."

She set her glass down. "Look! A forty year old man is just coming into his prime, even if he isn't quite the stud he was at twenty. He still believes that 'You aren't getting older, just better' crap. Well, if he's any good at business he's starting to get into heavy money just about then. All those years of hard work begin to pay off. His kids are gone, or they don't need him, so he's free of his family. But his wife is no longer a bombshell, if she ever was one. So when a man turns forty he often decides he deserves better from life. And for once he can afford it. So he begins screwing around. Or, he dumps his wife of twenty years in order to award himself a trophy wife. Isn't that right?"

In fact, that's just what Pearl's husband had done. He'd left her well-fixed enough, payment for their years of struggle together, and had gone off to do the Palm Beach and Palm Springs circuits with a new slim long-haired Princess of a wife, calling his broker now and then to ask how fast the money was coming in.

I was forty last year, and I have to admit it now, I was thinking about doing the same thing. Life with Bea had gotten really dull. The sex was as predictable and boring as her cooking, and she seemed to approach both the same way. We shared lots of interests, but there was nothing new to explore. Evenings, she read her romantic novels and I watched television. But I still cared for her, in a way, and I didn't want to hurt her, so I never said anything about it. I wondered if Bea had sensed something anyhow, and had mentioned it to Pearl.

"Well," Pearl went on, "With a woman turning forty it's different. She's nearly past it. Her kids are gone or don't need her. Raising kids has been her life, and now it's over. She finds it's harder to stay in shape, and she lets herself go a little. Her dresses don't fit her any more, so she spends more of her husband's money to buy more of them, and they still don't fit just right. She logs more time at the beauty parlor. Her husband logs more time at the office, and less with her. There're still things she hasn't yet done with her life, and she knows time is running out, and she knows she's beginning to forget what those things were. That's why Bea didn't want your party. I'm sure she told you that right off when you proposed it to her. There's nothing to celebrate when a woman turns forty."

"She did say that," I said. "I thought she was just depressed."

Pearl looked steadily at me again, and then took another sip.

I went on. "But I really am grateful to you and Kay. When the two of you cooked up these plans for tonight, her mood changed. Almost immediately! It was miraculous! I still don't understand it. My idea for a birthday bash depressed her, but yours gave her a new lease on life! I'd never have guessed it, that what she really wanted was an intimate night out on the town with just her two dearest friends. A fabulous girls' night out. Something she'd never done before. But that was what she wanted! Immediately she started humming around the house, telephoning and planning and talking and preparing. Weeks spent shopping for the very outfit she's putting on right now. All of today spent in the beauty parlor, sitting next to me the whole time, getting her hair and face and hands and nails and body worked over by any number of the women there."

"Anyhow, for months she's been so excited! I'm not sure why. What does she expect? Dinner, a show, some drinks afterward, and talk, lots of hot gossip she's never heard, she says. Do things she hasn't done for years, she says, maybe never done. Bea said that you planned to stay up till morning, the three of you, making girl talk, telling each other racy stories, doing girl things, away from husbands or other such depressing people. If she liked the way it worked out, she said, then she'd do the same things with you girls more often. They'd become her things too. And that's what cheered her up! I suppose, for Bea it's a change. We don't go out much together any more, hardly at all. Not for years. I'm pretty much satisfied to watch television."

"So I've heard," Pearl said. "Well, you've got the drift of it. Turning forty is a serious thing for a woman. Bea wanted to know how we've handled it, me and Kay. What we've really been doing since the big four oh. You're right. A year ago she was way down, and you weren't the only person worried about her. So we told her that on her fortieth birthday, tonight, we'd show her that life begins at forty. We'd tell her all our secrets."

"I'm forty-two now, you know. That rat of a husband of mine left me four years ago. Well, for a year I mourned like a schoolgirl, which is what I still was despite everything, I suppose. Then for another year I thought about the rest of my life, how to take charge of it. Well, since then I've been doing OK. Got me a job to keep busy, started to meet new people -- you don't know the half of it. So I've got lots of good advice to give Bea. I've given her lots already."

"Kay too. Kay told her some things right off that surprised even me, about that husband she still lives with. That Tomcat stud, what's his name, Steve. I've known for years that he's been sticking his prick into anything in skirts the way other people shake hands. But I didn't know he went for anything in pants too. He swings both ways. Did you know that? The man is an animal."

I didn't know that. I'd never met him, but he was a legend around town. I'd heard about his women. We were all maybe a little jealous. That may be why wives and ex-wives always seemed to be so protective of Kay, always inviting her to parties and dinners and sleepovers when her husband was out of town. But he was bisexual? That I hadn't known! "Why does Kay stay with him?" I asked. "She's a doctor. She's got her own practice. She's been our family doctor for years, and she's a good one. Bea trusts her. Kay doesn't need Steve."

"You really are an innocent!" Pearl said. "Because Kay's got her own men too. And her own women. They swing together. They're swingers. That's how they first met, at some swingers' convention, from what I hear." Pearl leaned forward. "But Honeybuns, you haven't told me yet how Bea talked you into joining us for this fabulous night. To do whatever we do. Especially looking the way you do, like one of the... uh... girls. What happened? Does Bea have something on you? Did she catch you slipping into her little silky nothings, and then shame you into wearing more of them? Do you have your own panty collection? Are you also a secret swinger?" Pearl lifted her face toward me, waiting for some dishy confessions.

"Well..." I began. But Pearl was on a roll!

"And how'd she get you into that beauty salon? Marge did a fabulous job, really, Honey! Those are long fingernails, longer than mine! And that is a perm they gave you, isn't it? I suppose it really took guts! Or was it blackmail, or a bribe? Though I must say, you do look terrific. You look... well, feminine. I don't think there's any doubt you'll pass."

"You know, don't you, that this night has cost you your manhood, as far as I'm concerned, and probably Kay. Maybe even Bea. I don't know how feminized you are inside, but you are certainly emasculated up front. In my eyes certainly. That's quite a sacrifice! You must have known that would happen. So why did you do it? We are never again going to be able to think of you as Bea's dullard husband! You're just too cute-looking! Now we'll spend all our time thinking about fixing you up with cute guys! Maybe even other cute guys in skirts! How in the world did Bea ever get you to agree to this?"

Finally, Pearl leaned back, looking at me cooly. She'd spoken her piece. She handed me her empty glass, and gestured toward mine, and pointed to the bar. I stood up.

"Pearl, the way Bea did it was, she asked me, and that's all there was to it," I said, a little too grandly. Pearl had finallly gotten to me.

And then Bea's voice came from the doorway. "That's right, I asked him!" Suddenly, there was Bea. "I decided early on that I wanted Henry with me tonight, but not as Henry. And that's why he's here. I have my own reasons, Pearl."

We both turned to look at her. Bea had really gotten herself ready for this special girls' night out, there was no doubt about it! She looked awesome! My God, what a costume! Short tight black leather miniskirt, and thigh-high boots with incredibly long, thin spike heels. A short stretch of exposed thigh, between her boot tops and her skirt, encased in black nylon. Those thighs looked like dark tubes, inviolable, strong enough to crush any man who dared put his head between them. A black silk blouse thrust forward by bare, jutting nipples, apparently she wore no bra, and then it flowed down and over her arms to be gathered at her wrists, and to billow down to her waist. A collar of red necklaces surrounding her neck like chain mail, and large red drop earrings dangling under her black hair, which was teased way up around her head as big as I could ever imagine it. Eyes outlined in black, and a slash of red across her mouth. Absolutely sensational!

I swallowed hard, and almost sat down again. Next to Bea I was a sweet, shy wallflower, in my pretty black cocktail dress. If there were any feelings of manhood left in me, that I was a guy wearing a skirt because his wife had asked him to, they were gone. There could be no men in the vicinity of Bea's outfit. Only varying kinds of submissives, until she gave one of them permission to try to service her like a man, if he could. I suddenly felt utterly helpless. I tried to compliment Bea, but my hands only waved in the air, and nothing came out of my throat but some high-pitched squeals. She saw at once what she had done to me, and smiled delighted. Her eyes sparkled.

"My God, Bea," said Pearl. "Talk about taking charge of your own life starting tonight!"

"That's what I'm doing, Pearl."

Then she turned to me, still standing and staring anxiously at her. "Don't worry, dear, this isn't for you. It's partly for me, and partly to help me keep some other people in line tonight, maybe. You'll do only what you want to do, no matter what I may ask you to do. I wouldn't want it any other way. Did I tell you upstairs that you look just lovely? Really, that dress is adorable! I knew that satin collar would be flattering once your breasts were large enough to hold it away from your body a teeny bit."

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