Men, What Made You Want To Wear Heels

[pebblesf]

On ‎11‎/‎8‎/‎2015 at 10:52 PM, maninpumps said:

BbigEed ,

 Your beginnings sound a lot like mine . I had a sister with a pair of leather and wooden soled sandals much like you described . She caught me in them and said if you are going to wear them ...learn to walk in them so she put on a pair of heels and taught me . Then to my surprise she gave me the pair I was wearing . They finally after miles of wear started to wear out and she made sure I had another pair about two sizes up as my feet were still growing . 

 I was in middle school back then and to this day she still has to show me her new heels and has to check out mine . Funny how we have been doing this for 30 years . I have moved more to platform wedges and she has moved to the lower 2-3 inch heels . We both like the peep toe style . 

 My family all know about my heels and crossdressing . I have been lucky about my folks and the fact they never judged me . My children have figured it out . My daughter asked once "Mom why do you have so many large high heels ?" and she told her they are daddy's . My daughter said can I wear them dad ? I said if you an walk in them . We don't make a big thing of it . The children see it  as no big deal either. I do hear about it if she thinks the style is wrong for me . I will say, when I am wearing heels or crossdressed I am not with the children unless they want to . 

very cool family indeed!

[Bubba136]

I cannot remember a time that I did not wear "girls shoes."  I can remember playing in my mothers closet and wearing her shoes as far back as two or three years old.  Although my parents tried their best to make me stop, when they took them away from me I'd pitch a grand fit until they gave them back -- which was the only way they could shut me up.

One morning, when I was around ten, I was wearing a pair of my mothers best dress heels while getting ready for school.  Thinking that I would just put them back on when I got home, I took them off and put them in my closet. 

My mother was not at home when I returned that afternoon and when I went to change my clothes, I noticed her heels were not there (my mother was wearing them at a function that she was attending.)  Later that evening, when I was getting ready for bed, I noticed that they were back in my closet.

One day several days later, I found a pair of classic black patent pumps with 4" heels in my closet. She had bought them for me, put them in my closet and reclaimed her own shoes to her closet.  From that point on, I openly wore my heels around the house.  

Not long after she had given me my own pumps, we had a long open discussion about the reasons why I liked to wear girls shoes and high heels. Although I could not really explain or give any satisfactory reason why, I knew I could (would) never stop. I also knew that while both she and my father weren't overly thrilled by my choice of footwear, they both realized that I was not about to stop wearing them on my own and they could not convince me to (make me) quit.

It wasn't long after that I got my second pair of my own heels.  A pair or red leather pumps of the same style as my black patent pumps.

I turned 61 on my last birthday,this past January.  In hindsight, over the years my life would have been much less complicated if I didn't have this "thing for heels." That being said however, with all honestly I can say that I have truly enjoyed each and every moment that I've spent in high heels and am eagerly looking forward to many more.

 

Edited March 19, 2017 by Bubba136

[Shyheels]

Sounds like you had wise and loving parents

[Thighbootguy]

10 hours ago, Bubba136 said:

with all honestly I can say that I have truly enjoyed each and every moment that I've spent in high heels and am eagerly looking forward to many more.

Wonderful story and thank you for sharing.

I am continually amazed that we survive our youth.

[Steve63130]

Great story, Bubba! Very inspiring. You are fortunate to have (had) wonderful parents. Thanks for sharing with us!

Steve

[swedeheeler]

For me it started with more kinky purposes. But when I realized it was more than so it took some more heels and a insight that this is very enjoyable. But I'm still stuck in closet with the most except for my cowboy boots.

[pebblesf]

6 hours ago, swedeheeler said:

For me it started with more kinky purposes. But when I realized it was more than so it took some more heels and a insight that this is very enjoyable. But I'm still stuck in closet with the most except for my cowboy boots.

My situation sounds quite similar buddy....I have made a bit of progress over the past few years, mostly due to the encouragement I have received here....

[hernaezjames]

For me it started out when i was a kid about 5 or 6 years old. Watching the cartoon "gem and the holograms" made me appreciate the the look of pointy toe heels since the main character gem always wears pink stiletto pumps. Then i saw my mom wearing the same type of stiletto just in color dark brown when going to work. The time comes when mom needed to go overseas because of work and i was left with my grandma. I was alone in the house when started checking things around like storage closet and found out a pink pointed stiletto pumpa exactly like the one gem is wearing.  I got really excited then slip my feet in the shoe, it was so smooth and the feel of the leather on my foot is really awesome (though the shoes were a bit big for that time). I stuff in some papers inside the shoes to make it fit so that i can walk in them. That same time there was also this tingling sensation all over my body which really feels good. Walk around the house wearing those heels and have done that ever since every time i get the chance alone in the house. Also discovered the brown pumps of mom and other pairs like strappy heels (keep on another storage closet) which ive worn all of those as i grow up until they wont fit me anymore. From there as i get older, my interest in womens shoes progress to all kind and type of shoes, pumps, strappy, mules, flats, slippers, sandals and womens sneakers. Up to now i dont own a pair of mens shoes. 

[pebblesf]

1 hour ago, hernaezjames said:

For me it started out when i was a kid about 5 or 6 years old. Watching the cartoon "gem and the holograms" made me appreciate the the look of pointy toe heels since the main character gem always wears pink stiletto pumps. Then i saw my mom wearing the same type of stiletto just in color dark brown when going to work. The time comes when mom needed to go overseas because of work and i was left with my grandma. I was alone in the house when started checking things around like storage closet and found out a pink pointed stiletto pumpa exactly like the one gem is wearing.  I got really excited then slip my feet in the shoe, it was so smooth and the feel of the leather on my foot is really awesome (though the shoes were a bit big for that time). I stuff in some papers inside the shoes to make it fit so that i can walk in them. That same time there was also this tingling sensation all over my body which really feels good. Walk around the house wearing those heels and have done that ever since every time i get the chance alone in the house. Also discovered the brown pumps of mom and other pairs like strappy heels (keep on another storage closet) which ive worn all of those as i grow up until they wont fit me anymore. From there as i get older, my interest in womens shoes progress to all kind and type of shoes, pumps, strappy, mules, flats, slippers, sandals and womens sneakers. Up to now i dont own a pair of mens shoes. 

I too remember that "tingling sensation" while wearing my sister's red go go boots

[hernaezjames]

Yes, its hard to explain that sensation during that time when i was kid but it was all over my body especially on my private part, its the best feeling ever. I got addicted to it and its the same feeling i get every time i wear womens shoes especially heels.

[robbiehhw]

This is a neat thread to see everyone's motivations and how things started. The human mind is a splendid thing.

When i first started to try on and then buy women's shoes it was to feel more feminine and from that feeling comes a "centered" feeling that i later learned was me dealing in the right way with gender dysphoria. It never excited me in any sort of intimate or fetish way. Learning to walk in higher heels to me seemed elegant and it forced me to adopt a more girlish walk as well. 

Lots of men have attraction to feet, so it would make sense that footwear fits into that also. I never saw feet as anything more than another lovely part of the wondrous human body, worthy of massage or a kiss or two (men and women included) but nothing more than that. To some people footwear, stockings and just clothes in general seem to stimulate a sort of primal area of the brain that generates pretty intense feelings. Totally interesting.

[Pumped]

Tingles? Yep, still get them with the right heels!

[Gudulitooo]

8 hours ago, hernaezjames said:

Watching the cartoon "gem and the holograms" made me appreciate the the look

Wait wait. For me it could have been "City hunter".

[dww]

Cannot tell you why, just liked girls shoes since I first went to school, in my first class was a girl in a pair of red sandals, wondered why can't I wear a pair like that, I was 4or 5 years old been into girls shoes since then, wish I knew why. 60 years later still wearing them.

[hernaezjames]

5 hours ago, Gudulitooo said:

Wait wait. For me it could have been "City hunter".

I rember that, also an old anime where the female characters usually wears a nice pair of heels.

[JeffB]

Speaking of anime characters who wear nice heels, I give you Sailor Mars from Sailor Moon with her gorgeous red pumps:

[hernaezjames]

8 hours ago, JeffB said:

Speaking of anime characters who wear nice heels, I give you Sailor Mars from Sailor Moon with her gorgeous red pumps:

Oh yes, sailor moon series is part of my childhood days. Ive watched it as i grow up. Those lovely red pumps that she wears, damn really nice and sexy. I remember that most of the male antagonist in the anime wear heels and make ups to which they do look like a woman. 

[bailey]

I always liked to look at high heels even as a kid. I can remember looking at the Sears catalogues and admiring the high heels. I never actually owned my first pair of heels until after my divorce from my first wife who never knew about my admiration for heels. Being by myself I decided to buy my first pair and see what it finally felt like to wear a pair of heels. They were a closed toe sandle, black with a heel cup and ankle strap. They were about 4.5" with a 1/2" platform. They felt fabulous and definitely thrilled me. My collection grew until I felt awkward and shameful, thus the collection was purged. I am very glad that I was honest and upfront with my present wife. Now we both have marvelous heel collections and we enjoy shoe shopping.

[jeremy1986]

10 hours ago, bnchmrk said:

 I always liked to look at high heels even as a kid. I can remember looking at the Sears catalogues and admiring the high heels. I never actually owned my first pair of heels until after my divorce from my first wife who never knew about my admiration for heels. Being by myself I decided to buy my first pair and see what it finally felt like to wear a pair of heels. They were a closed toe sandle, black with a heel cup and ankle strap. They were about 4.5" with a 1/2" platform. They felt fabulous and definitely thrilled me. My collection grew until I felt awkward and shameful, thus the collection was purged. I am very glad that I was honest and upfront with my present wife. Now we both have marvelous heel collections and we enjoy shoe shopping.

So happy the story has a happy end :-)

 

Edited March 23, 2017 by jeremy1986

[Shyheels]

Hopefully that's not the end!

 

 

[caultron]

On March 18, 2017 at 8:04 PM, Bubba136 said:

I cannot remember a time that I did not wear "girls shoes."  I can remember playing in my mothers closet and wearing her shoes as far back as two or three years old.  Although my parents tried their best to make me stop, when they took them away from me I'd pitch a grand fit until they gave them back -- which was the only way they could shut me up.

One morning, when I was around ten, I was wearing a pair of my mothers best dress heels while getting ready for school.  Thinking that I would just put them back on when I got home, I took them off and put them in my closet. 

My mother was not at home when I returned that afternoon and when I went to change my clothes, I noticed her heels were not there (my mother was wearing them at a function that she was attending.)  Later that evening, when I was getting ready for bed, I noticed that they were back in my closet.

One day several days later, I found a pair of classic black patent pumps with 4" heels in my closet. She had bought them for me, put them in my closet and reclaimed her own shoes to her closet.  From that point on, I openly wore my heels around the house.  

Not long after she had given me my own pumps, we had a long open discussion about the reasons why I liked to wear girls shoes and high heels. Although I could not really explain or give any satisfactory reason why, I knew I could (would) never stop. I also knew that while both she and my father weren't overly thrilled by my choice of footwear, they both realized that I was not about to stop wearing them on my own and they could not convince me to (make me) quit.

It wasn't long after that I got my second pair of my own heels.  A pair or red leather pumps of the same style as my black patent pumps.

I turned 61 on my last birthday,this past January.  In hindsight, over the years my life would have been much less complicated if I didn't have this "thing for heels." That being said however, with all honestly I can say that I have truly enjoyed each and every moment that I've spent in high heels and am eagerly looking forward to many more.

 

So, how old were you when you first wore heels out of the house? And what was the occasion? And how often did you wear them in the weeks or months after?

[Logjam]

I wish I knew why! I doubt the insight would change anything but I often wonder. Maybe the engineer native curiosity about how and why things work and work the way they do. I have the same curiosity about a few other interests.

Logjam

[w6ish]

24 minutes ago, Logjam said:

I wish I knew why! 

same here!  i would love to know "why".

[aussieheels9]

For me i think it was more the fact that i am/was sick of men's shoes as they are all the same. I love the wide variety that you can choose from with high heels and women's shoes in general. Also love how heels make you feel a lot more confident

[CAT]

Always loved the sexiness of stiletto heels. Thanks to me my ex hand 100 plus pairs of shoes and boots but didn't like heels as much as I did.  When she would complain about wanting her to wear heels when we would go out or when she would wear them how they hurt her feet or they were uncomfortable I would say it can't be that bad.  She then said if you like them so much then you wear them,,,,,,,,, OK!!!   I bought some and some more and some more after that only to come home   One day to find she threw everything out including my Little Shobox boots.  I could have killed.   200 plus pairs of boots and shoes gone.    How can you be mad at me when you told me to wear them?    Needless to say she is my ex and my gf is awesome and is completely ok with me wearing heels out within and without her. 

[Cali]

I always liked boots and booties.  In the 70's-90's I had a pair of shoeties with a 3 inch heel my first wife gave me. Wore those shoes until they finally fell apart.

Then 10 years ago by chance I found out I could fit women's size ten. I needed water shoes for a tropical vacation. The sporting goods store was out of the men's water shoe in my size, so I tried a women's version (better choice of colors too). They fit better that the men's version one size above my size.

I have had many ankle problems over my lifetime, sprained both ankles over 100 times each, multiple major surgeries. I was looking for new running shoes and search the internet for what might fit my feet. I decided that women's shoes had a better chance to fit, so I purchased some cheap running shoes to try out the concept. They fit better than any shoes I had ever had.  I have not purchase any men's shoes since then.  I started to buy booties with a 1.5 to 3 inch heel. Several years ago I had the need to raise both heels 4 inch.  I have been wearing 4+ inch heels ever since.  I hardly ever wear my short heels any more.

[Bubba136]

On 4/15/2017 at 0:34 PM, caultron said:

So, how old were you when you first wore heels out of the house? And what was the occasion? And how often did you wear them in the weeks or months after?

 Wearing my "girls shoes" outside in public was never a big deal for me.  They were "my"shoes"' weren't' they?    Wearing heels was a different story however.  I was older and social obligations during middle school and high school limited my opportunities.  I still wore them to the movies and such other occasions where they were less noticeable.   College, a wife and three little children, along with a 10 years as a pilot in our Air Force (which ended on medical disability) really put a damper on heels activity.  But, over the years, opportunities to which I took full advantage, presented themselves.  Over the years that I've been a member here, I've posted many comments outlining my life in heels.  Search my posts and comments in the archives if you are interested in finding out more.  It is a long story.  

[spikesmike]

carherine  and other heelers.  My interest in high heels started at an age from the crib. As far back as memory goes I loved/liked looking at any and all kinds of high heels.

As a child I wore my moms high heel shoes when no one was around, until I grew to where those shoes would no longer fit. Never wore heels while in the military.

 My first pair of good stiletto high heels were 5" heels that I had custom made at Ableman Trading Co out of Hong Cong, China. in 1969. I still have them, they are still in

good condition. I first started wearing heels in public ( full time ) around 45 years ago. I always wanted to wear heels in public but was to afraid to do it. One day a friend,

who knew of my high heel interest, said go ahead and wear them out. So what, What is anyone going to do ? So now at age 76 years old I am wearing stiletto high heels

every day all day long.     spikesmike

 

[CAT]

Looking pretty dam good too!!

[Thighbootguy]

On 5/10/2017 at 2:04 PM, spikesmike said:

 

21 hours ago, CAT said:

Looking pretty dam good too!!

Yep, blue and gray with a winning smile is a great combination.  Well done.