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killer heels

Rich kid in cowboy boots

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Posh Josh Harrington and  his girlfriend  had just come back from a  2 week holiday in Barbados, so  the cloudy but mild London weather was a shock after the 30 degree heat, as was the need to wear jumpers and coats.

With some unpacking still to be done his luxury riverside apartment, owned by his parents was a little more untidy than normal.



The couple had just finished in bed and all the passion and energy expended between the sheets had made them hungry. 

The 20 year old ex public school boy and his attractive 19 year old blonde girlfriend  Lucy had enjoyed padding around in flip flops and barefeet most the time on holiday, so for Josh preparing to go out for lunch, putting on a buttoned up shirt and his favourite pair of cowboy boots felt a bit of a culture shock.


'Babe's,  are we going far,.just wondering if you want me in  heels to or not ?" Lucy enquired of her boyfriend, as she grasped a pair of louboutin clos  noued high heeled sandals in her hands. She wanted to look hot for him of course but didn't want to wear these sandals if she was going to be standing around or walking too much. 


"Yah, of course babe. ...I want you to look hot hey!?" Josh responded. 

'Was just thinking of somewhere here by  the marina for lunch sweetie? "  Josh replied in his refined accent. The couple had only been dating for a couple of weeks before the holiday and weren't yet totally exclusive.

 Lucy teeteted into the master bedroom where her boyfriend was getting dressed.He had already put on a black roll neck sweater,  a pair of designer jeans with a thick belt and was now slipping his feet into a pair of tan, western boots with high heels. 


(Tan,  cowboy boots with 3.5 inch heels)

Lucy noticed they were calf high cowboy styled ones. Josh had several pairs like these. This particular pair had been bought for him by an ex girlfriend from R Soles store in the kings Road, London for his 20th birthday. 

'Hey ...I havent seen you in those before baby.They  look cool......heels really  suit you! " She said

Josh enjoyed wearing cuban heels when around  girls,  as they made him seem taller and more confident. He enjoyed his reputation as a ladies man and in his immature mind successful men of that type usually wore boots with a heel. 

This particular pair had  subtle 4 inch heels,  usually partly hidden by boot cut jeans. This meant his feet were angled down sharply when wearing them, making him strut and swagger a bit like a girl in stilettos when walking. 

"How are they to walk in?" Lucy teased.


(A picture of Joshs patent leather cowboy boots with 4 inch heels)

"Oh... fine baby. Just a pair of normal boots hey ?" The 20 year old replied evasively, being vain and proud.

'Your heels are as high as a girls stiletto though......don't your feet ache in them on a night out? " Lucy asked.

"Umm...A bit . I tend to wear these when dating or going to a restaurant. The tan...cowboy boots i wear for clubbing. " he clarified helpfully.

Lucy being from a wealthy family didn't mind that and was used to arrogant lovers and family members alike. She didnt mind boyfriends wearing cowboy boots providing done fashionably.

"I love a man in those actually...They look so hot!" She continued.  

Encouraged, Josh asked " Oh, what do you like about them honey?" 

"The smell of the patent leather, the way they make a guy walk with a kind of swagger...its also usually  a guy that's good in bed in my experience.

Josh was nodding appreciatively, he definitely saw himself as a ladies man and was proud of his sexual prowess. 

Lucy continued. "Right so walk in those now for me now baby.........on you go!"  she pestered.

Doing as he was told, Josh angled  and clicked one of his stacked cuban heels on the bedroom flooring and strutted back and forth . The 4 inch heels had the effect of tighteningh his thighs as he moved, and as Lucy had said making his walk bit sexier


"Hmm. ..cool!" Purred Lucy seductivley. 'You need to straighten those though honey' she pointed out, pulling the bottoms of his boot cut jeans over her boyfriend's heels.

Since his late teens, Josh had often worn a pair of cowboy or western boots when dating or socialising. He was of the view that the girls he dated loved them.

 As he put on his herring bone coat and  made his way to the doorway of his flat, it was with more of a strut than the average guy in flat boots or shoes. 

Some said this made him look arrogant but Lucy knew that any guy wearing similar heels do make you strut and swagger a bit more. 

As the good looking, young couple left to go to the wine bar, both their heels click clacked on the pavements, although at a different rhythm.  Lucys 5 inch louboutin sandals made a light sound as  she teetered in small steps. Her boyfriend's thick Cuban soles a sturdier sound.

Edited by killer heels
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Since Lucy and Josh started dating 3 weeks ago, everything had been going well.  They were a very attractive couple, got on well, enjoyed a drink and a laugh, in bed they were both very physical and compatible.  Both liked the other looking hot, Lucy had been quite controlling however as to what her previous boyfriends should wear, and had started applying this principle to Josh. She also didn't like him mixing with friends who were uncouth or ribald as some of his ex public school mates could be.  On the sartorial front, although Josh as an Alpha male was mainly in charge, Lucy made a point of letting him know to be seen with her he had to look good.  Therefore, in practice, she liked the 20 year old in crisp, cream shirts, smart jackets and sometimes even leather trousers.  Jeans were also fine, providing smart and top branded. Josh was himself, vain and narcissistic, enjoying dressing up and admiring himself,  especially when it pleased his partner and meant more fun in bed.

Josh, for his part liked Lucy in nice lingerie, heels and full make up, having been used to escorting glamorous young ladies, he expected this in a partner.

Lucy had taken a shine to her boyfriend wearing boots as we saw last time, the 2 pairs of cowboy boots he already owned were in constant use. Having been used to woo many a pretty blonde over the past year or so, as a result he was used to having a bit of extra height in his Cuban heels when dating girls.

The fact was Lucy was used to sporty, hunky rugby types, both to escort her and please her in bed. She certainly liked her men to be a bit taller than her. Vain and image conscious the 5'5 inch blonde often wore heels herself, favouring in particular racy, over the knee suede boots, meaning she was often the same height as her 5'6 inch boyfriend if even in a modest pair of 2 inch stilettoes.

Josh Harrington didn't quite measure up in the height  department, an issue he'd had with other girlfriends, which had lead to him favouring wearing high heels when dating.  Lucy encpuraged him in this, as a result much like a vain girl, the handsome, arrogant playboy often had sore,  swollen feet after strutting around for a few hours in the nightspots of West London.


'Baby I was thinking, you wear your boots so much these days...maybe you could do with a new pair, why don't we go to that specialist store in the Kings Road? What do you think?'

'Sure, I guess  these tan ones are getting a bit tatty' he replied.


Edited by killer heels
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Wish I had a provocative story like that to tell, oh well...

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OK, well my story isn't quite as interesting, but it sure felt great to me.....

Several years ago, I met a boot guy online that lived on the west coast of the US.  After a few emails, and phone calls, he agreed to meet me when I had a long layover in his city.  "Joe" met me at my hotel, he was a good looking tall fellow with nice long legs, and he wore great knee high black boots with 5" heels, over his jeans.  This particular city is a fairly progressive place, so I was not worried about being heckled or attacked.  In any event, we walked all around the city, from bar to bar in our boots.  This fellow had no problem walking a quite a good clip in 5" heels, I had trouble keeping up.  It was so cool, because most of the time, I was not even focusing (worrying) about wearing boots, I can honestly say I forgot about it a few times.  I remember going into one bar, it was full of rugby players that must have been celebrating a victory.  Needless to say, I was quite self conscious being around these rough characters wearing 5" boots, even if mine were under my levis.  We chatted with a few of the players, none even mentioned our boots, I was able to quit obsessing about it after a half hour or so....

I can honestly say, this was one of the best times I have ever had...And yeah, we were wearing stiletto boots, not cowboy boots, but this is the only story I can come up with. 

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Hey...Thanks for sharing.  I can tell it really was important to you 

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