Didn’t have my first pair of heels until I was 26

[Roberta Lane]

Looking back on my long crossdressing journey it’s hard to believe that I didn’t get my first pair of ladies shoes until I was twenty six years old.Up until then I dressed in private in my bedroom at my parents house from the age of twelve.I had my own pantyhose/ tights and wore my mother’s skirts and dresses but I had no shoes of my own as I didn’t know my shoe size.One day, I just took the bit between my teeth and went to buy a pair of four inch patent pumps from a shoe shop whilst in boy mode.My male shoe size was a seven so I bought a pair in a ladies size seven.Luckily,when I took them home the shoes fitted me and looked great when teamed with tights.But sadly,one day my mother found my stash of feminine garments including the hose.I had to make up a story and tell them I bought them for my girlfriend for a present but bought the wrong size.As my girlfriend was a dainty size four my mum must have thought it was a likely story.However,she hit on the idea of giving them to 18 year old daughter of a family friend who happened to be the same shoe size.So off they went to her.Nothing was ever said but I often wondered if our family friend had any indication that the shoes had been worn.I really missed those shoes.

 

• This topic was modified 1 year ago by Roberta Lane.

[Stephanie Bass]

Hi Roberta such a shame girl wish i was a size 7 ha ha more like a womens 11 works well and have plenty there as wife is a very supportive and we love shopping together .. We look every time we go to thrift stores for the correct size and usually find at least 1 pair to add to the collection  good luck girlfriend ..

Stephanie Bass

[Sandra Lasco]

Hi Roberta, I can only imagine how tough this must have been on you as a 26 years old loosing your clothes and shoes you identify with as a young woman at heart.

[Patty Phose]

I’ve been wearing pantyhose, heels and bra since I was 4. They were borrowed or hand me downs. At 13 I bought my own pantyhose, at 17 my first heels, short shorts, bra, panties and wigs. At 18 I got my own place and got everything girly. I dressed at home every day and went out often.

I guess after you mother gave your heels away, you had to get another pair.

[Anonymous]

So sorry you lost your first pair of heels and I know that made you want heels so much more.

When I was about 5 I got into my aunts closet and put on a pair of her heels and walked out in front of the adults to show them off. It did not go well and I was told boys don’t wear girls shoes. So I guess I “borrowed” my first pair.

Being closeted most of my life and having big male feet, I didn’t buy my first pair until I was in my 50’s. Now I can walk pretty well in 4 inch pumps. Having a large foot makes selection very limited.

[Camryn Occasionnel]

I bought my very first pair of heels from Amazon in August, 2019. I was 72.

It took me a full year of practice to get comfortable walking in them. It’s hard to teach an old dog new tricks, but not impossible.

[Donna Ceedee]

I got my first pair of heels that actually fit me when I was in my forties . I ordered a pair of patent red four inch pumps. I had some what of an idea on size. Maybe it was a bit of luck but they fit perfectly. Before that I had worn a pair of four inch open back heels of my first wife’s. They were a bit tight and my heel hung off the back bit but they were workable. I love being in heels. Now I have several pair.

[Natalie Jones]

Roberta,

I think we all can remember our first pair of heels, or women’s shoes of any type. To bad you had to lose your pair in that manner. Did you ever see that women wearing your shoes ?
I didn’t purchase my first pair until I was in my later 30’s. Actually I ordered through a catalog two pair of 2 inch heels one in white and one in black. I used to have all my purchase sent to a Post Office box. I kept stopping every day Hoping they had arrived. When they did I couldn’t wait to try them on, oh what a feeling it was having my own women’s shoes that fit. I realized that day why women enjoy buying and owning many pair. If I had the ability I would probably own dozens and dozens

Natalie 💋💋💋

 

[Roberta Lane]

Hi Natalie,no I didn’t see that girl wearing my shoes.I met her on just a few occasions after that.My family was very friendly with the girl’s mother for a while but we lost touch with both ladies.

[Lara Muir]

Hi Roberta,

What a shame to have to give up your stash!
That must have been awful. If mine ever gets discovered, I guess I’ll have to come clean at this point in life.

I got my first pair of heels at 59. I always wondered why a lot of women loved them, and “needed” so many.
It’s no longer a mystery. Now they are my favorite part of dressing! 3 years later I have 8 pair, and I doubt I will ever stop wanting more!

Lara 👠

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