Shopping for High Heels

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Positions I put myself in.
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This is a short true story which although has no overt sexual content is one which many cross dressers may relate to.

I began cross dressing many many years ago and found that I enjoyed the sluttier side of dressing - which you may be able to tell from my stories! I adore high heels (the higher the better!) and love the look and feel of both PVC and leather and how wearing it makes me feel.

I doubt that many people who know me would guess this and this is how I would like it to stay as I think that very few, if any, of my friends would understand the sexual thrill which I got from dressing....although there are one or two who I could picture dressing up like a little bitch for!

I know that I am not gay but when dressed I always got urges to act as the slut that I was dressed like and would very often end up with dildo or vibrator in my mouth, ass or both!

I have been in a loving relationship with a girl for the last few years and she does not know about my little fetish. I would also never wish for her to find out as I know that it is not something which she would like and perhaps not even accept.

Some time ago I got rid of all of my clothes but recently I have been getting the desire to wear high heels again - my stories were supposed to be a release from dressing not a catalyst to do so!

In addition to my dressing I also discovered the excitement of putting myself into compromising positions where there was a chance that I might get caught or humiliated in front of a stranger.

I discovered this thrill after having been out drinking one night with friends. On getting home I was feeling horny and so put on one of my slutty outfits before going outside and taking a walk around the area where I used to live.

It was not something which I planned but it felt so exciting to be outside dressed and being night time hearing nothing but the clicking of my high heels on the pavement wondering if at any time a stranger may walk around a corner and see me.

As I say though - I gave that all up and am now in a loving relationship. My urges though recently returned and I felt the need to be humiliated in a way that only a cross dresser knows -

I was away for the weekend without my girlfriend and on the drive back home I stopped at a shopping centre (a mall to those across the Atlantic!). Looking around I saw a women's clothes shop which had some very slutty high heels in the window so I went in and headed straight to the shoe section.

The shop was quite quiet but there was a girl restocking the shoes and tidying the area up.

After looking for a few minutes I got her attention and pointed out a pair of 6" black patent heels with a 2" platform. I asked the girl if they had any larger sizes out the back. She asked me which colour (they had light pink as well) and so I asked her to check for both. She came back a minute or so later and said that they only had small sizes before she walked away.

The largest size which they had in that shoe were a UK 7 and I knew that they were too small for me. I also know that a UK 8 are too small but longing for a moment of humiliation I picked up a pair of very high sexy tan wedges and walked towards the till with them.

The girl who I had asked about the shoes was stood there talking to the girl behind the till (I think that they were the only two people working) and as I got close the girl serving went to take the shoes from me. Instead of giving them to her though I asked if it would be OK for me to try them on, looking towards the changing rooms as I asked.

She hesitated for a split second but then said that that was fine so I turned and walked towards what were in effect the women's changing rooms (remember that this shop only sells women's clothes).

As I walked in I was really hoping that a woman would be walking out and would see me with the shoes but as I said the shop was really quiet so this did not happen. I went into a booth and pulled the curtain across before slipping one of my trainers off and hoping that the shoe would fit.

As expected the sexy wedge was just a little too small for me but really I knew that anyway. Putting my trainer back on I walked out of the changing rooms still holding the shoes and put them back on the shelf.

At this point I could easily have left the shop but wanting to prolong my agony for a little longer I went back to the till and told the girl serving that they had been too small and that I had put them back on the shelf. In reply she told me that she had found that those ones pinched a little and asked if I had found the same!

I said that they were a little too small and that I couldn't get in them but that I had asked about larger sizes - turning to the other girl who was still stood there.

The girl serving said that they only went up to a size 8 but that they may soon be starting to get size 9's as some other women's shops were starting to do so. Then to both my embarrassment and pleasure the two girls started suggesting other women's shops that might have larger sizes!

They suggested a shop which I knew carried some larger sizes and I said that I had already looked there but that the shoes were not exactly sexy (flat shoes!). The girl behind the till agreed and asked me what I was looking for.

I told her that I was looking for a shoe with a high heel and that I thought anything below 4" should be classed as flats! As I said this I could feel myself going red and the girl simply smiled and suggested a couple more shops that I could try.

I thanked the two girls for their help, turned and walked out of the shop knowing that my face was still red as I left and wishing that I could have overheard what the girls were now saying.

The next day I was on the outskirts of London for a work meeting and as I drove down the busy high street I saw what looked like an independent shoe shop which had all sorts of high heels in the window.

My meeting finished early and so with the thrill that I had experienced the previous day still in my mind I tried to remember where I had seen the shop.

My heart skipped as I saw the shop and I knew what I had to do. Pulling into a supermarket car park a little further on I parked up and began to walk back.

As I entered the shop I could see that it was very small and only sold women's shoes. In the shop I could see an Asian girl and another lady who I assumed was her mother. There was also a girl (maybe 19 or 20) serving them.

With the girl serving the women I looked around and saw a section on the wall where there were all sorts of sexy high heels.

Whilst looking at the shoes and picking a few pairs up I noticed the Asian girl looking at me as she was paying at the till. As she and her mother left the phone rang and it was answered by a man who came from out of the back. He gave the phone to the girl and seeing me came over and asked if I needed any help.

I pointed to the sexy heels and asked what the largest sizes were which they stocked. He said that they only went to 8 and asked if there were any that I liked! I pointed to some sexy 6" heels which had spikes on them and he said that they were very popular.

Knowing that they wouldn't fit I picked up some 6" slingbacks in a black velvet like material and asked if he had any size 8's. The man said that he would go and check and very shortly came back with a box. The shoes again had a 2" platform and as I took them from the box I could see that they were a very small looking size 8.

After looking at them for a little bit I said that I thought that they may be a bit small and handed them back to him.

As he took the box and turned away though the urge to put myself in a humiliating position again came over me and I asked if it would be OK for me to try them on!

He turned and smiled and said that that was fine and handed me the box. Being a shoe shop there was obviously no changing room and so I took box from him and took a seat on one of the chairs in the middle of the shop.

When I had been talking to the man I had had my back to the rest of the shop and when I turned to take a seat I saw that there was now a woman picking up some of the sexy shoes that I had been doing the same too just a few minutes ago.

Wearing a suit, shirt and tie I sat down and slipped my shoe off before trying to put my foot into the sexy sling back shoe.

Looking up I could see that the woman had now turned her head slightly and was looking at me from the corner of her eye. The man was also looking and it gave me a huge thrill to know that these two strangers were watching a well dressed man (me!) trying on skyscraper heels in the middle of a women's shoe shop.

Even though the shoes were slingbacks they would not fit and so I put the shoes back into the box and gave them back to the man after putting my shoe back on. I thanked him and walked from the shop feeling so turned on by what I had just put myself through and imagining how I could push it further.

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GuyWearsLingerieGuyWearsLingerie2 months ago

Love it! I have tried on high heels two times at a store (now out of business called Payless) that carried larger sizes. The first time I was looking for some 5+" stilettos with ankle straps. I told the sales girl the truth, that I needed them to go with a red lace baby doll I had just purchased. She measured me and brought a pair suggesting I try them on. I was wearing shorts and flip-flops and agreed. She gave me two of the little footies to put on and helped me put the heels on. I stood and walked up and down the aisle as she watched with a big grin on her face. She told me I definitely have the legs to wear heels. lol They fit fine and I bought them. As I was taking them off sitting on the stool my shorts slipped down and she saw my bright pink lace panties and told me she liked my panties.

About a month later I went back to the same store and she was working. She recognized me and asked what I was looking for. I wanted a similar pair of high heels but in silver. She had them and I tried them on again and bought them. She asked how the pink heels worked out and I showed her a pic of me in the red lace baby doll with the heels on. She loved it and had me send her a copy of the pic.

1WiseSage1WiseSageover 6 years ago
Girl Heels

You can't have a serious heel fetish! A 6-inch heel with a 2-inch platform is only a 4-inch heeled shoe - that's a young girl/old woman's shoe height. Strictly speaking that's barely a "fashionable" or workplace shoe, but definitely not in the "sexy" category.

A sexy heel has to be at least 4-5/8 inches in height, net (without platform). CFM (come-fuck-me) heels start at 5 inches, net; and sky-scrapers really apply to 6, 6-1/2 and 7 inch heels, net. Fetish heels begin at 7-1/8 inch heel, net and through ballet heels to minimum 10-inch heel and no more than 4-inch platform (net 6-inch heel height). And it should go without saying, that the heel itself has to at least be stiletto or pin!

A real high heels lover would know this...

AnonymousAnonymousover 7 years ago
Totally relate to it!

Been there, done that quite a few times! It's good to know you're not the only one with the same fetish and the same urges...

AnonymousAnonymousover 11 years ago

wow that sounds like me

desireethtttvdesireethtttvover 11 years ago
Right out of the life of Desiree...........

although I take it further and wear my spikes as a male in the butchest of places. I applaude you for your courage and daring.

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