onyourtoes

An Easy Fifty, by OnYourToes

"Lose a bet?"

It was Saturday morning and I was sitting alone in the coffee shop reading the morning paper.

I was dressed casually: jeans, pullover sweater, and black Mary Janes with 4 inch block heels and dark socks.

"Hey buddy."

Realizing he was talking to me I looked up and saw a 20 something male who was dressed similarly to me, except he was wearing dirty white athletic shoes.

"Huh?"

He pointed to my shoes and carefully enunciated, "I said, did you lose a bet?"

I looked down at my shoes, compared them to his (and every other man I had seen that day), and realized what he was trying to say.

"No, no. I don't need a bet. I wear what I want to." I pointedly looked back down at my paper, hoping to end the conversation.

"I'm sorry, I'm not trying to be a jerk. I'm really curious as to why you're wearing high heels."

I sighed and motioned him to sit down at the seat across the table from me.

He smiled and reached his hand out, "Bob Weaver."

"Nick Foller."

"You see Nick, I walks into this here restaurant and I was in line waiting. I looks over and sees this nice pair of shoes when everybody else is wearin' sneakers. I'm wondering if the rest of her is as classy as her feet and follow the legs up. Well, what to my surprise, but she's got a flat chest, short hair, and a mustache. I says to myself, 'Robert, this guy don't look at all like a fag. Maybe he gotta wear them lady's shoes 'cause of a bet.'"

I mentally counted to 10 while thinking up lost bet paybacks that should be enforced upon him. "Ok, first of all two things you should know."

"Uh, huh."

Knowing the redundancy would go over his head, I explained, "First of all, men who are regular heel wearers are almost 100% straight, heterosexual, and not gay. Second, they're not a lady's shoes, their mine."

Starting to get into the redundancy, I finished up, "Bought, purchased, remunerated, and paid for."

Sounding like he really meant it, Weaver said, "Sorry, I should of known. But why do you wear them, then? I mean you don't have to 'cause you're not one of them, and, I didn't mean it like it sounded. I mean don't they hurt your feet?"

Letting his fixation on sexuality go, I explained, "Did you ever wonder why men's shoes are all so the same? Black, brown, or white, with maybe a pair of navy blue socks to liven things up. I once wondered too and decided to find out.

"Well, since there's nothing in our genetic makeup or bodily mechanics that controls compatibility with shoe color, I decided to try some other colors."

Apparently the compatibility thing was confusing him, but I continued forward. "A couple years ago, I went into a shoe store and started looking around and decided to try a pair of shoes just like what I'm wearing today."

"Didn't they think you were weird or something?"

"I thought of that, too," I smiled and went on, "You'll like this -- I told the clerk I had lost a bet."

He laughed out loud at this, and I couldn't help chuckling myself.

"When I tried them on, I really felt different. Tall, cool, ready to take on the world, then when a nice looking lady came up to me and said she thought I looked great in heels, I was hooked."

He said, "Like a drug?"

"Uh, no. Just a figure of speech. You know, like, well I just liked how they looked and felt. I bought them, and now most of my shoes have heels. As long as they fit right, they don't hurt."

I looked down, sizing up his feet. "Looks like you're about size 10 like me."

"Nine and a half. What about it."

I slipped off one of my shoes and motioned towards it. "Here, go ahead and try it."

"Naw, them's lady's shoes."

"No, remember I told you, they're mine. Look, nobody will see or care, the place is practically empty."

He said, "Not on a bet," but didn't sound very resolved.

Smiling, I said, "You sure about a bet? Ten bucks says you won't put it on."

As I laid a ten on the table, he slipped off his sneaker and nervously shoved his foot into the mary jane on the floor.

This time I held up fifteen dollars and motioned to the other, now vacant, shoe on the floor. "Five more says you won't put on the other one and another ten to stand up and take a couple steps."

Well, you could have fooled me. Not only did he put the other shoe on, but he stood up and walked completely around the table. I was impressed, he really walked well, too.

He sat down, didn't immediately take the shoes off, but scooped up the money. "Uh, what was your name, Nick? I can't believe it, but I like them. You were right, tall, cool, and tough. Where'd you get..."

Before he could finish asking where I bought them, A female voice interrupted us, "Robert?"

He looked up very surprised with his face rapidly turning white said, "Hi Peg. Nick, meet my girlfriend, Peg. Uh Peggy, this is Nick who I was just talkin' to. We were, uh..."

Peggy pointed to his feet. "Bob, those shoes look great on you! Why haven't I seen them before? You really ought to wear them more often."

Looking very confused he started to stammer, "P-p-peg. I, uh, well, you see..."

Peg motioned her head towards the counter. "Wait, let me get my coffee."

As soon as she left, Bob pulled out his wallet and quietly, but urgently said, "How much? How about fifty?"

"For the shoes? And my twenty-five back?"

Peggy was starting back to the table.

Bob dug into his wallet, "Ok, ok. Seventy-five. And keep the sneakers."

He handed me a wad of bills under the table as she settled back into her chair. Before she could say anything, I said to her, "Bob here was telling me how he always thought men's shoes were boring and one day decided to try those as an experiment. He probably didn't know how to tell you because you might think him strange."

Peggy looked at Bob and said, "No, I don't think you're strange at all. Any man masculine enough to wear heels in public is OK by me."

I stood up in Bob's hideous sneakers. "Peggy, Bob, I've got to go. Maybe I'll stop across the way at Snazzy Feet and pick up a pair, too."

As I was walking out, I heard Peggy say, "I didn't think you'd ever wear heels, even on a bet. Let's see how you walk."

The End.

DallasHeels

I think that was a great story. Would have been better if it was "based on a true story" lol...:academic:

wood&metal

Great story. Top notch!

ilovepumps!

This paragraph made me laugh LOL

"You see Nick, I walks into this here restaurant and I was in line waiting. I looks over and sees this nice pair of shoes when everybody else is wearin' sneakers. I'm wondering if the rest of her is as classy as her feet and follow the legs up. Well, what to my surprise, but she's got a flat chest, short hair, and a mustache. I says to myself, 'Robert, this guy don't look at all like a fag. Maybe he gotta wear them lady's shoes 'cause of a bet.'"

sevenup

Great story , nice twist!

chris100575

Nice story! I liked the twist at the end too!

Chris

ShockQueen

GREAT story, onyourtoes! Loved it all the way through, and I agree....would have been EVEN better if it was based on a true story.

We CAN dream...and then make them reality!

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