A mile in her shoes

Hey!  Hitching is cheating, and cheaters never win!

When my girlfriend Emma’s car broke down and needed a new engine, we got into a big fight.  I tried telling her that it just wasn’t a financial good time to spend the thousands of dollars to get her car fixed and that she had plenty of other options.  But every option I put up she’d knock down with some flimsy excuse. 

Take the subway.  She complained that taking the train alone meant some guy pressing up against her when the car was full and practically getting dry humped. 

Take the bus.  She complained that taking the bus meant getting felt up by the skeezy guy that inevitably sat next to her.

Take an Uber.  She complained that having some dude oogle her through his rearview mirror was just begging for a crash. 

Walk.  She got really pissed at this one and said if I’d ever walked in heels I’d know that walking just wasn’t ever going to be on the table. 

We were at an impasse with me unwilling to pay for her repair and her unwilling to take any other form of transportation.  That’s when she made the offer.  If I could demonstrate that any of those forms of transportation were acceptable as a woman, she’d not only give up her car but give me a thank you BJ.  If I couldn’t honestly say that I wanted her to take these forms of transportation after experiencing them as she would, I’d not only pay to repair her car, we’d swap my new Mustang for her ’97 Corolla. 

I’d dressed up as a girl at last year’s Halloween party so I thought I could convincingly go as a woman and agreed.  I had no idea how far she’d go though.  I had to take Monday off just to get ready for the rest of the week.  We got extensions put into my hair and even dyed it that popular silver some girls have.  I got my entire body waxed.  I spent two hours at her nail salon getting my nails and toenails done up.  And the final piece was the shoe store where she got me a pair of 3 inch heels.  I tried to complain and say that she could always wear sneakers like everybody else, but she just pointed down and made me realize she’d been wearing the exact same pair all day.  Without complaint. 

Tuesday came and I thought I’d just take the subway into the city and check out some books at the library.  Emma put me in a corset and a dress that made me look like I had real curves.  With the makeup she put on me and the heels, I was ready.  Sadly, she was right.  I took the train during the same rush-hour she’d have to use it through and some guy ended up behind me.  The space between us dwindled to nothing and then I felt him pressing against my ass.  It wasn’t too bad and I was ready to claim victory until I noticed him getting hard.  Even with me glaring angrily over my shoulder at him you couldn’t wipe the mile-wide smile off his face. 

I wouldn’t want my girl to have to experience that, so I focused on the next day.    The bus is never as crowded, but it does take a little longer.  When I got on it was nearly empty so I almost claimed victory then and there.  But each stop filled the bus up a little more, and just as Emma predicted some guy ended up sitting next to me.  He wouldn’t take my silence as a sign I didn’t want to speak with him and kept trying to make small talk.  When his hand landed on my knee and stayed there I had to fight the urge to punch him.  Sadly, I had to tell Emma she was right about the bus. 

Before calling for the uber the next day, I made the comment that maybe it was the dress and not me.  Even though I was passable, I wasn’t nearly as pretty as Emma and yes… she wore heels to work most days but she also wore simpler clothes a lot of the time too.  So, she put me in a green crop top that I’d seen her wear plenty of times along with the matching skirt.  I had to admit that it wasn’t quite the affect I was going for.  It wasn’t as overtly sexual as the dress was, but this outfit showed off a lot more flesh. 

Later that afternoon I had Emma pick me up in my ‘Stang from the ER.  It turns out she was right.  The Uber driver kept looking at me in the rearview mirror.  When I finally couldn’t take it anymore and shouted at him he actually turned around and leered directly at me… and rear-ended the car in front of him. 

I tried to beg off the walking day as my ankle was still sore from the car accident, but Emma wouldn’t have any of it saying she’s walked on sore ankles plenty of times.  Halfway to downtown I was ready to throw in the towel.  I was hot and sweaty.  My ankle was throbbing.  I was getting wolf-whistled at from seedy construction workers and I wouldn’t ever accept my girlfriend having to go through this.  But at the same time I didn’t want to admit defeat and trade over my tried and true blue Mustang for her POS Toyota.  That’s when I stuck my bright red thumbnail out and started hitching.  I figured I could get a ride into the city, hang out a bit, hitch a ride to a few blocks from home, and walk in and declare myself the winner.  I’d take the celebratory BJ and then offer to just buy her a new car anyway as I wouldn’t want her to even break down and have to go through what I’d done this week.

I refused the first couple people that stopped as they just looked unsavory.  One was driving a classic ‘child molester’ van with no windows and the other was talking to my pushed up cleavage when I leaned down to look through his window.  The next guy though seemed honest enough.  He looked like the classic new dad type with a newish teeshirt and baseball cap, and his Caddy said loud and clear he had enough money to not be trolling for girls.  It turns out I’m a pretty good judge of character… except for the fact that he was an undercover cop and I was trying to hitch in a known prostitute hangout.  Going to jail was a humiliation to horrid to contemplate whether or not he found out I wasn’t a woman.  So when he said I could do him a favor and get out of this without being taken in, I jumped at the chance. 

Admittedly, I probably wouldn’t have offered the favor if I knew what it was, but by the time he had me miles away in a private place it was too late.  It was either preform as he asked and earn a ride home or go to jail.  At the very least, as he guided my lips up and down his thick shaft, it gave me an idea of how Emma could give me my own blow job!

Image source:  50 Shades of Impregnation Tumblr