A Woman's Wager

byandtheend©

A man who lost a bet must dress as a woman and discovers he likes it.

"Pardon me, Madam," said Ed trying to hustle his shopping cart down the aisle by a very large woman. With her carriage blocking one side of the aisle, she was hunched over a shelf with her big ass blocking the other side of the aisle. When the woman turned to move her carriage out of the way and faced him, they recognized one another.

"Jake? This is a surprise," said Ed. "What the Hell are you doing food shopping here, so far away from home?"

"Oh, hi Ed. I never figured I'd see you or anyone, for that matter, out here in the boonies. I could ask you the same question. Why are you shopping way over here? Don't you usually grocery shop closer to home?"

"I do, but I had to see a client out here and I finished with him earlier than expected. Not knowing what else to do with myself, when I saw the market, I figured I'd stop and buy what I needed before getting back on the highway to go home. Besides, Carol is home hanging around in her nightgown smoking cigarettes, drinking coffee, and watching the Price Is Right. I'm not eager to go home to that. I'd rather be here than there, even if it means food shopping, if you know what I mean," he said with a laugh.

"I like this grocery store," said Jake looking around it. "It's much smaller than the superstores, but it's not nearly as crowded than the grocery stores we have back home. I can get used to shopping here. It's more enjoyable. I can actually think, while shopping."

"Yeah, I know what you mean, this place is empty. I'm enjoying food shopping for once and there was no line at the deli counter and their prices aren't bad either," said Ed. "Without being surrounded by wall-to-wall people, I feel as though I have the time to around and to look at things without being rushed, pressured and jostled."

"Yeah, the reason why I hate food shopping is the crowds and the small aisles, but this place is nice. The aisles feel so much bigger without the crowd," said Jake. "I'm not big on crowds."

"Now that I see what my life would be like and how much easier it would be living someplace like this, it makes me want to move away from the big city and out more to the boondocks, where I can breathe and stretch out without bumping into someone." He looked at his friend and neighbor with a face full of confusion. "Only, a better question than why are you shopping way out here is why are you dressed as a woman, if you don't mind me asking you that, Jake," said Ed with a nervous laugh and a tentative smile. "Are you attending a masquerade party?"

"Oh, that. I forgot. Sometimes, I'm so comfortable wearing women's clothes that I don't even realize I'm in drag," said Jake looking down at himself, fixing his dress, and pulling at his pantyhose beneath his dress. "It's because of Linda. We had a little Valentine's Day bet. She won and I lost," said Jake with a little laugh.

"A Valentine's Day bet? What about? I can only imagine what she'd have to do if you had won. She'd be giving you hot sex every night, right?"

"Oh, it was nothing like that, I can assure you. It was all very innocent. It all started after I had been complaining that she doesn't dress up anymore."

"You and me both. My wife is the same way."

"It all came to a head on Valentine's Day when she came downstairs in her usual attire, nightgown, robe, and slippers. Her hair wasn't done, she wasn't wearing any makeup, and had no intention of taking a shower. In the way she looked, I almost didn't want to give her the flowers, candy, and card that I bought her, but I did anyway. She hardly looked like my little Valentine," said Jake with a laugh.

"She could have at least got cleaned up for Valentine's Day and looked pretty," said Ed with an understanding shrug.

"If you ask me, I think she stayed like that in her bathrobe and nightgown, just to spite me and to prove her point because she won the bet and I lost."

"Yeah, but, maybe you need to cut her some slack. Maybe it was too early to be all dolled up and looking nice for you. Women can't dress up all the time. Sometimes, like we men, they just want to kick back and relax."

"Dress up all the time? She never gets dressed anymore. Besides, it was two in the afternoon, Ed. She had been up for hours already. To be honest, I'm tired of seeing her walking around the house like that. She never dresses up anymore. Not to mention that it was a special day, Valentine's Day. C'mon, she could have, at least, put a brush through her hair and put on some lipstick."

"She sounds like my wife," said Jake. "My wife has taken to being a slob, when hanging around the house, too. I guess the honeymoon and the romance is over."

"Most days she just looks sloppy, but after a while I tire of looking at her from across the kitchen table or from my easy chair in the living room. I don't know if you've ever seen my wife without her makeup, but it's not a pretty site," he said with a chuckle. "Some days she doesn't even shower," said Jake.

"What about when she goes out? Doesn't she dress up then?"

"No, even when she leaves the house to go out somewhere, to run an errand, to go food shopping, to go to the mall, or for a doctor's appointment, all she ever wears are sweatshirts, jeans, sneakers, and her dark glasses. You'd think she was movie star in the way she always wears her dark glasses. I was hoping by winning the bet with her that she'd have to dress better and take more pride in her appearance. I realize we've been married for a long time, but that's still no reason and no excuse for her to stop caring about what she looks like in front of the me."

"I know exactly what you mean, Jake, I do. I know exactly what you mean. My wife is the same way. Sometimes she's in her nightgown all day long and I hate coming home from work to that and going to bed with that. The hot, young women at work fill my nose with their lingering perfume and my brain with a memory of their coiffed and made up loveliness, while dressed in their best clothes," said Ed giving Jake a knowing look. "Do you know what I mean? After a while, you can't help yourself from looking, then before you know it, you want to touch, too, and do more."

"Yeah, tell me about it. I've been tempted more than once by other women, women who take more pride in their appearance than my Linda," said Jake.

"If my wife only knew the thoughts I had for the women at work, she'd divorce me. If the women at work only knew the thoughts I had for them, I wonder what would happen," said Ed suddenly drifting away with his thoughts of extramarital affairs, no doubt.

"Exactly, my point, Ed, exactly my point. Listen, I don't want to start cheating on my wife, again, been there and done that. I'm too old to be lying, cheating, and sneaking around. I'd rather stay home for a home cooked meal, instead of having fast food outside, if you know what I mean. Yet, when the supper is not even out of the freezer and defrosted, then you begin to succumb to the temptation and give in to your hunger for a quickie," said Jake.

"Very well put, Jake. Suddenly, I'm hungry but not for food," said Ed with a laugh.

"I can't help but feel that the lack of pride she takes in her appearance is a direct reflection on how she feels or no longer feels about me," said Jake. "By making a friendly wager with her, a woman's wager, if you will, I was just hoping to stimulate her to realize and appreciate the fact that we're still a sexual couple and young enough that the romance isn't or doesn't have to be over yet, at least not for me. I still want her. I still love her. I still want to have sexual relations with her, but not when she's looking like that, so much like wrinkled, smelly bed clothes."

"I know what you mean, buddy. My wife and I, well, I can't remember the last time we did it," said Ed with a look of sadness on his face. "If it wasn't for my right hand, I'd have no sex at all," he said with a laugh.

"Join the club," said Jake. "I've never masturbated as much as I do now, since I was a teenager."

"I miss those seemingly spontaneous days, when she'd get all dolled up and I'd take her somewhere nice. Then, after we got back to the house, we'd put on some light music and open a bottle of wine. She'd put on a little sexy number at night and we'd do things behind our closed bedroom door that would embarrass most people. Now, it's her flannel nightgown, terry cloth bathrobe, and fuzzy, dirty, pink slippers twenty-four seven," said Ed with sudden sadness.

"Maybe they both need an injection of hormones. Maybe their estrogen levels are out of whack and the reason why they stopped being feminine," said Jake. "Yet, whatever the reason, I miss the way my wife used to be."

"Yeah, that could be," said Ed. "Maybe they're going through the change of life and God help us if they are because I heard that women get really mean, bitchy, and hysterical during that time. Now that I think more about it, I wonder if I still have my old college football helmet. Maybe, for my own personal safety, I should start wearing that around the house with earplugs. That way I can't hear her when she starts yelling, crying, and screaming, and I won't get hurt when she throws dishes at me."

"Maybe, I should do the same," said Jake pausing to reflect on what his friend just said, while wondering if the reason why he suddenly dressed as a woman was because his wife was dressing more like a man. "Ever since my wife stopped working, ever since she no longer had reason to leave the house, ever since I made enough money to keep her home, she doesn't take pride in her appearance anymore," said Jake. "Her hair is always a mess and she doesn't even wear makeup, not even so much as lipstick. I like lipstick. Gees, I wonder if she's depressed."

"Your lipstick looks nice, by the way. It's a nice color on you."

"Thank you," said Jake giving his friend a smile. "With the bet that I made with her, I was just hoping to get her to look more presentable is all. I never really expected her to win, but she did.

"What was the bet about?"

"We bet on the Super Bowl. I figured I had a lock on that bet. What does she know about football? Nothing. I even let her pick first, which was dumb and my downfall, and was shocked as shit when she picked the team that I wanted."

"That's too bad. Beginners luck, I guess," said Ed.

I never seriously thought in a million years that I'd have to dress as a woman, yet, here I am dressed as Jacqueline instead of as Jake."

"Jacqueline? Who's Jacqueline?"

"Oh, that's just the name I gave myself and use. The illusion doesn't work if someone asks me my name and I tell them it's Jake."

"Illusion? What illusion?"

"The illusion that I present of myself pretending to be a woman."

"Ah, I see," said Ed taking a step back from his friend and looking impatient to leave, flee actually, suddenly.

"Actually, I always liked that name, Jacqueline. President Kennedy's wife was named Jacqueline and then there's that Jaclyn Smith from Charlie's Angels, only she spells her name differently. God, I'd give anything to look more like her. She was so very beautiful. I've been buying her clothing line at K-Mart. Only, most of her things don't fit me, but then there are some items in the plus sizes that fit."

"Okay, but it's still a stretch as to why she'd want you dressed as a woman if she won the Valentine's Day bet. You'd think she'd ask you to take her out to dinner or to a nice hotel or buy her a new pair of shoes or something like that instead of this," he said looking down at his friends feet. "Nice shoes, by the way, Jake, but where did you find shoes to fit your feet? Don't you take a size 13?"

"Let me tell you, it wasn't easy. I searched high and low," said Jake looking down at his pumps. "I found these on sale and they are so very comfortable. That's the thing about taking a size 13, actually it's a size 15 in a woman's shoe, no one has any, but when they do, they are drastically marked down. Anyway, my wife said that she's tired of doing her hair and makeup and prancing around in uncomfortable clothes with high heel shoes. She even said that if she has to wear another pair of pantyhose and put on another binding bra, she'd kill herself. Can you imagine?"

"Speaking of bras, where'd you find a bra to fit your 48" chest?"

"Let me tell you, again, I had to search high and low. I even went Online and when I finally found my size, I bought all they had, a white one, a black one and this beige one that I'm wearing now. I'm still looking for a red one for those sexy nights, if you know what I mean," said Jake noticing his friend staring at his boobs.

"They look so real," said Ed.

"Wanna feel? Go ahead. Take a handful of my boob. I don't mind, really. Go ahead," said Jake sticking out his chest just as an elderly woman entered the aisle and turned her carriage around to go the other way.

"No thanks, that's okay," said Ed. "I'll wait until I go home and grab my wife's boob, if you don't mind. Thanks anyway."

"They feel real. I have those gel implants in my bra and they feel like the real thing. Go ahead, feel my tit. Sometimes, when I'm horny and alone in the car, I feel myself," said Jake with a laugh. "It makes me horny to feel my own phony tits."

"Wow, they do feel like the real thing," said Ed finally succumbing to the temptation of feeling Jake's fake boobs and squeezing a handful.

"So anyway, she said she's been dressing up for 40 years and she bet me that I couldn't even do it for a week. It was her way of trying to make me understand what she must go through to get dressed and to make me understand in a small measure of what it feels like to be a woman. She didn't think that I could do it, but I did and I have, as you can see," said Jake moving his hands out from his sides and looking more like a fashion model.

"Okay, I understand that part of the bet but Valentine's Day was last month. Your week of having to dress like a woman was over three weeks ago. Why are you still dressing as a woman? Did you lose another bet?"

"I can explain that, too," said Jake looking a little nervous. "Once I started dressing as a woman, it released the inner woman in me and I liked it. I was free from neckties, business suits, white shirts, and wingtips on weekdays and flannel shirts, jeans, baseball caps, and construction boots on the weekends. Suddenly, for the first time, I felt pretty in pumps, pantyhose, pearls, and pillbox hats and I liked it."

"I don't really know what to say to that, Jake," said Ed. "If you don't mind me saying so, and I mean no offense to your inner beauty, but it's all a bit bizarre to me seeing you in drag. There's just no way I'd ever dress up as a woman. Now that I recall, though, there was that Halloween party I attended so long ago where I dressed as Marilyn Monroe and if I say so myself, I looked pretty hot."

"I bet you did," said Jake. "You'd make for a pretty woman. You have a nice figure," said Jake looking around at Ed's ass. "Say, speaking of Marilyn Monroe, don't you just love this flared dress that I'm wearing? Doesn't it make me look skinny, in the way it pinches in at the waist and flares out at the hips. You think that it wouldn't but it hides my hips," said Jake looking down at himself before twirling around. "Dressing like a woman makes me feel so sexy and I like the way men look at me."

"Don't do that, Jake."

"What? Don't do what?"

"Don't twirl around like that. People are starting to stare and I think that elderly lady, the one who left our aisle a moment ago, is calling for the manager," said Ed taking another step away from his effeminate friend. "Listen, Jake, let me give you a newsflash," said Ed with a laugh. "Men don't look at you because they think you look pretty or that you look sexy. They look at you because they've never seen a 6'5" man in 2" pumps dressed as a woman before. To be honest with you, you don't look anything like any women I've ever seen in my life."

"Oh, well, okay, that's good to know," said Jake suddenly looking sad, embarrassed almost. "I don't care. I still feel pretty and that's all that matters, how I feel."

"I'm sorry, Jake, but you look ridiculous," said Ed. "You're as tall as the shelving in this place. Maybe if you shaved your mustache, you could at least fool the toll booth attendant on the parkway, but unless you're in a room full of sightless people, everyone knows you're a man, a cross dressing man. Trust me."

"Yeah, well, I suppose they do, but that part of it doesn't really matter. It matters more to me how I feel. If you tried dressing as a woman yourself, you'd understand how I feel. It's how it makes me feel inside, bringing out the real woman in me, and no matter how you think I look, I feel pretty and sexy," he said twirling around again and again.

"Hey, look at the time," said Ed. "I'm late for, uhm, something. I'm sure I have an appointment with someone, somewhere. Listen, it was nice to run into you. Give my regards to Linda. Let's have a beer sometime to catch up. Okay? I gotta go. I got to run."

"We can have a beer now. I'm done shopping. I can just head up to checkout, put the stuff in my car and there's a bar across the street. We can talk football. Hey, how 'bout that Super Bowl last month, huh? That was some game, wasn't it?"

"Now? No, I have to go. I don't have the time to grab a beer. Sorry. I have to go now. Sorry. Bye. See ya," said Ed leaving his carriage of food and practically running out of the store.

"Ed, you forgot your carriage. Don't you want this food? Hey, these are nice brussel sprouts he picked out. Ed? Ed!"

Gees, was it something I said, thought Jake. Maybe he didn't like my outfit, he thought looking down at himself. I knew I should have worn the other handbag. This pocketbook just doesn't go with these shoes. They clash. I'm so embarrassed that I'm not as coordinated as I should have been. Maybe, before heading home, I should hit the mall and pick up another outfit, something for the spring.

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