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@HighHeelsAreFun

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Following
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Lil’ 30 something y/o crossdresser πŸ’ƒπŸ»who loves to dress up in high heels & anything sissy πŸ’… Please leave a tip if you really like my stuff

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Joined December 2018
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
Red lingerie. πŸ”₯ My favorite!
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
6 years
I’ll smile when I feel like it. 😝
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
6 years
I kinda have a thing for swimsuits. πŸ€·β€β™€οΈ #crossdresser #transvestite
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
3 years
Fourth time I ever went out dressed as a girl. This was on a Carnival cruise ship. My wife did my make up and it was super fun!! Didn’t get laid but my wife might have pegged me. I can’t remember. πŸ˜‚
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
3 years
This was me the first time I ever went out dressed. It was for Halloween!! πŸ˜‚πŸ˜‚ Everybody lost their shit when they saw me. πŸ˜‚
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
6 years
These pants are a little hot. Lemme take β€˜em off. Besides, pants are a bit too boyish for me anyway. 😝 Gotta be careful though. Don’t wanna show my boi goods. 😡😘 Not yet anyway. πŸ˜‰
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
Red dress, red heels, red toes.
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
6 years
I swear I’m not a bitch. Well, maybe a little bit. You like it... 😘
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
More...
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
I’m missing my little 19 year old cross-dressing self. Know of any young sexy cross dressers I should be following? Let me know please!!
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
5 years
Mmmmmm.
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
6 years
I love lingerie and slutty clothes!! 😜 I’d wear it all day if I could.
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
2 years
So this was me the other night when we went out. It felt so awesome to shave everything off and get prissed up all girly. Can’t wait to do it again.
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
6 years
This is pretty much my go-to picture when I tell someone about my #crossdressing πŸ™‚
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
6 years
So... this is me. I’m a few years younger in this particular picture. I like lingerie, short dresses and heels. Really high heels. It was really hard for me to tweet this so please be nice.
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
6 years
Tryin’ to look like a fierce bitch. πŸ’‹πŸ’‹ #crossdresser
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
It’s been awhile since I’ve done my makeup so here’s some older pics where I went full femme mode. Rare photo of me smiling. I don’t do that in pictures often. πŸ˜‚
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
🎼 β€œBut when you smile at the ground, it ain't hard to tell You don't know, oh-oh You don't know you're beautiful” 🎼 You’re beautiful! Don’t forget it!!
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
5 years
This is probably my favorite picture of me. It’s pretty much my β€œgo to” whenever I tell somebody about my crossdressing. Tbh, whenever I see this all I can think about is how I wanna fuck the shit outta me. 😝 Or into me, depending on how you look at it.
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
5 years
How about some side cheek? πŸ˜šπŸ’‹
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
If you want me to follow you just like, retweet or comment on this tweet. ✌️
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
5 years
I haven’t tweeted in awhile. I figured I might as well start with one of my favorite things: My black β€˜Fuck Me!’ heels.
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
6 years
As a guy I’m very confident and extroverted. As a girl, not so much. I’m gonna work on that. #crossdresser
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
10 months
Lovin’ this romper! So cute!! ❀️
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
10 months
My feet! 😝
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
Hi there! πŸ‘‹
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
3 years
Playing around in my hotel at Universal Studios. Got my Harry Potter mask and everything. πŸ˜‚
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
3 years
I’m about to go shave my legs and I’m super excited about that. Need to take some new heels pictures for you guys. I have so many heels you haven’t seen yet. 😝 Here’s some you have for now:
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
I feel like such a sissy in this. It’s great! πŸ˜‚
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
Just tryin’ to look cute with my β€œpackage”. #crossdressing #crossdresser #transvestite #tranny
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
3 years
Shakin’ that booty in my sexy red/pink teddy and heels.
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
It’s fun making videos of my feet. πŸ˜‚
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
6 years
@Eddie38377038 Omg that really means a lot to me to read that. Thank you! I have a whole set from that night and other pic sets too. πŸ™‚ I will try to share them as I get more comfortable here. πŸ€·β€β™€οΈ I also have a lot of leg shots. πŸ˜‚ Here’s one:
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
3 years
Love painting my nails. πŸ’… So sexy!!
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
3 years
More of dem feets and toesies. Can you tell I love heels?
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
10 months
More feet in heels! πŸ™‚
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
4 years
I really like this dress but it had to come off sooner or later.
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
10 months
New heels.πŸ‘ 
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@HighHeelsAreFun
Classless πŸ’‹
@HighHeelsAreFun
3 years
Red lingerie kind of day.
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