The Shoe Store

Story Info
Guy finds a great new shoe store to buy heels at.
1.1k words
12.3k
7
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I have always enjoyed the feel of pantyhose on my legs, ever since I was a little boy. My name is John and I love to wear women's clothes underneath my work clothes. I am 5'8", have a slender build and keep my legs shaved all the time. When my friends ask why, I explain that it helps when I swim. Today, after work I had decided to go and check out the new shoe store that had just opened a couple of months ago.

I have probably a dozen pairs of women's shoes and am always on the look out for more, especially at a bargain. This new place, The Shoe Palace, bragged that the majority of people wore the wrong size shoes, so I thought I could possible get my feet measured and then figure out what that would translate to women's sizes. After work while wearing tan pantyhose and my loafers I walked into The Shoe Palace and began to peruse their selections. Initially, I acted like I was looking at men's shoes, but then wandered over to the women's.

I was so engrossed in the different heels that they had, that I didn't hear the salesman, Karl, walk up behind me. He asked me several times if I needed any help and finally tapped me on the shoulder to get my attention. I nearly jumped out of my skin. I am embarrassed to have been caught in the women's section, but played it off by being startled.

I tell Karl that I don't need any help that I am just looking, he then goes into his pitch about people wearing the wrong size shoe. The next thing I know he has me sitting down in a chair and has removed my shoe so he can measure my foot. My pantyhose covered foot is quite obvious, especially since he is holding it in his hands. As he runs his hands up my pants he realizes that I am not just wearing knee highs, but more than likely pantyhose.

As he gently holds my foot, he brings it closer to his crotch and I can start to feel his excitement. He tells me that he would love to help me find some special shoes while he rubs my foot against his growing hard on and that he would be willing to give me his employee discount in exchange for a favor. As I visibly swallow I slowly nod my head yes.

He takes me into the back of the store to the office, tells me to find some more appropriate clothes to wear from an old box containing things past employees left behind and that he will be right back. As he leaves the office he locks the door. I can't believe what is happening as I begin to rummage around in the box. Surprisingly I find a black skirt and a pink t-shirt with Hello Kitty on it. As I strip off my clothes my own excite is evident and I hurry to put on the skirt and t-shirt.

The t-shirt proves to be a bit small so I tie a knot in the bottom to make it look more provocative and the skirt just barely covers my ass. I decide to sit on the edge of the desk and await my new friend. As I hear the door being unlocked I get a flutter of butterflies in my stomach, not sure what all is going to happen.

As Karl enters the office he tells me that he has locked the front doors and that we will have as much time as we need. As his eyes take in my new look he tells me that I look quite cute. He then asks what size shoe I wear and I quickly tell him my size in women's shoes. He says he has a couple of pairs I think I will like and disappears. He returns shortly carrying several pairs of high heels.

The first pair he has me try on is a pair of 3" Mary Jane's. After putting them on my feet for me he helps me stand up. He has me walk back and forth asking how they fit. They fit rather nicely, however, I prefer heels with an open toe as I usually keep my toe nails painted and today is no exception. As I turn to tell him this, I see that he is rubbing his hard on through his pants.

Since I feel like I am dressed as a slutty school girl I take some rubber bands and put my shoulder length hair up in pig tails and say in my best girl voice that I would love to help him out. He just stares at me and stops rubbing his crotch. I then sashay over to him, drop to my knees and reach up and grab his pants. As I unbuckle them and slid them down his legs I see that he is actually wearing silky red panties.

As I gasp he just looks down at me and smiles. He tells me that once he saw I was wearing pantyhose he figured he had found a mutual cross dresser. As I hook my thumbs into the waistband of his panties and pull them down, his rock hard cock springs free and bounces down and hits me on the nose, leaving a trail of precum from my nose to his cock. Without missing a beat, I reach up, grab his cock and guide it to my lips, swirling my tongue around the tip cleaning it of the rest of his precum.

As I play with his balls while sliding back and forth on his cock with my mouth I hear him moan with enjoyment. It doesn't take very long before he starts to tense up and grabs my head and he forces all of his cock into my mouth and down my throat and begins to shoot rope after rope of cum down my throat.

As he softens and slips out of my mouth he tells me that that was the best blow job he has ever had. I tell him it couldn't have been that good as it was only my second one I've ever given. As I stand he says that he would love to repay the service and I just smile and wink at him. I try on several other pairs of heels and Karl actually puts on a garter belt and some nylons along with a sun dress he has stashed in his backpack.

After Karl returns the favor and goes down on me I decide upon 2 new pairs of open toed wedges with 5" heels. I pay for my purchases and Karl gives me his card with his cell phone number on the back and tells me that if I ever want to play dress up again I should give him a call and he would love to cum over and play. As I leave the store I know for certain that I will be back often to see what new shoes they have in stock.

The End

  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousalmost 5 years ago
Great

I need to find a shoe shop just like that one

AnonymousAnonymousabout 5 years ago
Good Story!

Now that you have our attention,keep after it with chapters 2,3,&4!

63lsmith63lsmithabout 5 years ago
OK

Not bad, I liked it.

Share this Story

Similar Stories

Backseat Introduction Girlfriend's dad and boyfriend share the back seat.in Gay Male
Beautiful Black Dress He finds a gift sent by his ex-girlfriend's father.in Gay Male
Friend's Father During a long weekend at a friend's, his father takes me.in Gay Male
The Birth of a Sissy How a graduation present turned into a lifelong gift.in Gay Male
Girlfriend's Dad He has an encounter with his girlfriend's father.in Gay Male
More Stories