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2.
Stiletto Heels is the plural of Stiletto Heel. The term is used to describe a pair of stiletto heeled shoes or boots or stiletto heels when discussing them as a general phenomenon or as a fashion item(s).

See Stiletto Heel for definition.
She put on a pair of high stiletto heels which accentuated her calves... Stiletto heels show no sign of going out of fashion despite the efforts of fashion designers and writers.... Stiletto heels caused so much damage to floors, tarmac surfaces and even aircraft floors, that there was a call for them to be banned when they were introduced in the mid 1950's.
by Mike Martlet June 29, 2006
 
1.
A type of heel on a woman's shoe that is less than 1 cm wide at the tip. The original stiletto heels in 1953 were about 4 inches high and were made of hardwood sheathed in steel or were solid aluminium with screw in steel tips. Though some of today's stiletto heels have exposed steel or brass heels, since 1958 up to present they have been mostly made from hard plastic with a steel tube inside to strengthen them; the steel tips have a thin metal rod that fits very tightly into this tube.

Today's stiletto heels can be as thin as 0.5 cm and as low as 1.5 inches or as high as 5 inches; any higher generally requires a thick platform sole as in the modern pole dancer shoes where the often transparent moulded plastic platform unit has a 6 inch heel and a 2 inch platform sole. Such shoes are also quite popular for “ballbusting”

They were once seen as dainty and fragile, but both the damage that they caused to floors and being named after a thin lethal dagger, means that nowadays most people see them as being dangerous. They have thus taken on sado-masochistic connotations and though most people would never admit it, they fascinate both men and women because of their lethal power. The stiletto heeled leather boot (kinky boot) has always been the symbol of the dominatrix and this item has passed into the mainstream to become a standard fashion item for the modern woman.

High heeled shoes have always been regarded as sexy, not just for their body altering and leg lengthening effect, but in themselves; the heel is a phallic symbol and the arch under the heel is a vaginal symbol. But the stiletto has this extra lethal dimension in that they are capable of piercing things such as testicles for instance. Team them with pointed toes, particularly the new long pointed toes (a phallic symbol in itself!), and you have an incredible instrument of either pleasure or castration! Stiletto heels whether boots, sandals, slippers or pumps are sometimes used in sexual foreplay. The thinnest heels are thin enough to insert into the end of the male penis and push down a good 3 inches or so and the heels can also be used along with pointed toes to playfully kick and tease the testicles. During the sex act the heels can be used as spurs to urge the male on or slow him down and for the male, the combination pain and pleasure of heels in the thighs and calves together with nails in the back and the sexual orgasm can give a tremendous endorphin rush!

Contrary to popular belief amongst many men and women who don't wear them, with practice they are not difficult to walk in and today's career women can be seen running for trains, hopping on and off subways and buses and hurrying up and down stairs. Some will tell you that they feel confident and even invincible in business meetings and presentations; their distractive 'erection getting' qualities means that while the men are busy trying to wrestle with thoughts of sex, they can take advantage of them and win the argument or the deal.

Much to the disgust of many 40 and 50 something feminists, it is the stiletto clad post-feminist modern 'have it all' career woman of today who is reaping the hard earned benefits of the feminist era and she is using her sexuality to get ahead even further, - but on her own terms not the men's. It's not for nothing that those successful and ruthless women on Wall Street and in the City district of London were and are called "Spike-Heeled Power Bitches"!

The pointed toe stiletto-heeled pump (or court shoe) once the symbol of female oppression, has become the long pointed toed stiletto heeled ankle boot that is now the symbol of the get ahead career woman!
His manhood grew stiff in anticipation as the stacatto click of approaching stiletto heels grew nearer.....
by Mike Martlet May 14, 2005
 
3.
fetish shoes, boots, or sandals with an extreme narrow heel of 5 inches or higher up to an 8 inch heel without a platform sole
A Dominatrix who would wear a pair of black patent shoes with six inch stiletto heels to trample a male slave leaving her heel mark on his body as a symbol of her power
by Karlos B January 18, 2009