Rebecca Crossdressa

I’m a guy who enjoys classically feminine clothing and high heeled pumps, both on a woman and especially on me 😉. I love the contrast; menswear Is designed to be practical whereas womenswear is designed to be sensual and alluring. It simply feels so sexy, stimulating, enjoyable, and just plain fun to wear. I think being a woman involves a lot more than what’s between a person’s legs, so I’m attracted to pretty CDs and trans girls. I don’t want to live as a woman full time but enjoy dressing like one when I get the chance.

[vinnyboy48624]

[rebeccacrossdressa]

Why yes, thank you. As a matter of fact I would like to try on your pumps!

[snuglyrapidveil]

[jonnyq212]

A young beautiful woman out on the town be free baby do it!

[rebeccacrossdressa]

She looks like she’d be a lot of fun! Very pretty and sexy in her black bra and heels.

[rebeccacrossdressa]

Who wouldn’t love that view? Especially as she slowly lowers herself…

[rebeccacrossdressa]

Do women have any idea of the amount of power and control they can have over a man just by slipping their nylon covered feet into a pair of black stiletto high heeled pumps?

[rebeccacrossdressa]

She won’t need to ask me twice! Hopefully she’ll have a dress or skirt available too, I’ll provide the pumps.

[rebeccacrossdressa]

So many pairs of panties, so many years, so many happy memories. I really can’t remember who my first pair belonged to, must have been a girlfriend’s, but now the panties are all mine and I must have over a hundred pairs in all styles and colors. But black satin or nylon full back bikinis, hipsters, and briefs are still my favorite to wear with my stockings or under my pantyhose. It’s so great when I get aroused and my little head pokes himself out above the panty waistband, like he’s saying “hello, look at me. I need some attention now!” And he always gets it 😏.

[rebeccacrossdressa]

Every once in a while someone will ask why a man would want to wear stockings or pantyhose? My question is, why WOULDN’T a man want to wear stockings or pantyhose? They feel so awesome on bare legs, and I just love it when I run my hands over my stockings or when I rub my legs together, I know I’ll never stop wearing them. Then pairing them with a bra & panties, high heeled pumps, and a flowing skirt or dress- fantastic!

[rebeccacrossdressa]

Please tell me about your journey and how it began. Mine started when I was 10.

In elementary school, maybe second or third grade (7 or 8 years old) I remember looking at the girls and wondering what it felt like to wear a blouse, skirt, and shoes. Their silky blouses, loose, free flowing skirts, and heeled shoes just intrigued me and held my attention. And when I thought like that my little man would feel like it was filled with concrete. But I didn’t have any sisters, and my mom’s clothes and shoes weren’t all that sexy so it remained pretty much dormant until a girlfriend moved in with me and I had access to her clothes. Her shoes were too small, but Frederick’s of Hollywood catalogs were out by then and I was able to order my first pair of black 4” stiletto pumps. So then I was able to put together some blouse / skirt and dresses outfits with her bras, panties, and pantyhose; plus my new heels. After that Amazon and eBay came on the scene and I went to town buying all sorts of feminine apparel.

How about you, what did you start off wearing?

[rebeccacrossdressa]

What boy doesn’t have that dream soon after puberty hits? It’s one they’ll have regularly for the rest of their lives.

I remember my first time, it happened the night after I spent the day out shopping with my mom in some department store. She was busy in the dress area and I wandered around and came across the “intimates” section. I couldn’t stop myself, I had to walk around in it, mesmerized and enthralled by all of the soft, silky things I I saw. I imagined what it would be like putting them on and wearing them, and of course my little man was at full attention the whole time. It wasn’t until some time later I got my head together and left to find my mom. I guess I must have been blushing, because she asked where I had been. I mumbled some nonsense, and we left.

But later that night I had the greatest dream of being back in that intimates section, picking out and trying on various items, with the sales girls helping me and saying how pretty I looked. Then waking up in the morning and realizing that I needed to change my underwear 🙂.

Anybody else have crossdressing dreams? It was my first of many.

[rebeccacrossdressa]

I was thinking about this today. I realized that an early girlfriend was my crossdressing “muse”. She frequently wore form-fitting dresses, matching bras & panties, pantyhose, and heels when we would go out. Today I wear the same style of dresses, bras, panties, pantyhose, and heels as she wore. I learned a lot about the various styles of feminine clothing from her, and that inspired me when creating my own personal feminine style (although she wasn’t as big of a fan of garter belts and stockings as I am 🙂).

Who was your feminine muse that inspired your crossdressing style? I’d love to know!

[rebeccacrossdressa]

This was so true for me. An old girlfriend arrived for our first date at a coffee shop directly from work. She was wearing a form-fitting dress, pantyhose, and heels. HUGE turn on, I stayed with her way longer than I should have but she frequently wore that combination of form-fitting dresses, pantyhose, and heels (especially black stiletto pumps, my favorite) so it was REAL hard to breakup with her.

[rebeccacrossdressa]

As a young boy, as early as second grade, I remember seeing women and older girls wearing all different kinds of heels, and they always caught my attention. I couldn’t help but wonder what it would be like to wear them, and as I was wondering could feel my little man getting hard. Mom’s were OK but not all that sexy, and this was way before eBay and Amazon were around, but I remember going into thrift stores looking for any that were at least close to my size. Never really found any, but when I moved out I finally ordered my first pair of 4” black stiletto pumps from Frederick’s of Hollywood.

When those arrived of course I needed stockings. Which of course meant I needed panties, and bras, and dresses, etc. Then my girlfriend moved in and expanded my available wardrobe, and now 30 years later I have maybe 60 pairs of heels. Anything 4” and below I can rock like an expert. Higher than that is a bit more challenging, but I just can’t crossdress without heels. I think high heels, especially pumps, are essential to the crossdressing experience. And oh so much fun.

[rebeccacrossdressa]

You have to be careful when you’re admiring yourself in a full length mirror wearing your black bra and matching panties, garter belt & stockings, and favorite pair of black high heeled stiletto pumps.

Accidents happen 😏.

[rebeccacrossdressa]

All boys remember doing that growing up, whether it was after school when you knew mom wouldn’t be home for a few hours or on the weekends when mom & dad were both out. Then it was playtime! Exploring all of her lingerie drawers, trying to decide which panties, bras, pantyhose, and slips to try on, then to the closet and looking through all of the dresses before selecting two or three. Then choosing a few pairs of heels, and finally modeling each outfit in front of the mirror and marveling at the pretty, sexy, girl looking back at me!

I continued the tradition with live-in girlfriends, and it grew to include clothing and shoes I bought for myself. So much fun! Even in boy mode I’m usually wearing panties and pantyhose underneath, and in cold weather I’ll add a bralette or bustier for a bit more fun.

[rebeccacrossdressa]

….hmmmmm. Maybe that’s why the ladies always leave them lying around the house? On the shower rod, on top of the dresser, in the laundry room, etc. They know a guy can’t help but pick them up and put them on. After grabbing a pair of their panties to put on first, of course. Which then leads to a bra, dress, and heels😏.

[staciecd]

[rebeccacrossdressa]

I thought this was cute; what a wonderful surprise it would be if you asked a girl to dance and as you were pulling her toward you both of your little men had risen to say “Hello!” to each other. What followed would be a really great dance, and just the first of many more intimate moments

[likealayerednylon]

[nylonsissy]

Sweet video!!!🥰❤️💕!!!…Totally LOVE slipping into a pair of nylon stockings, connecting garters and stepping into a pair of sexy heels!!! I’m certain she knows just how lucky she is too!!! I know I’ll never be as hot as she is but it sure is fun trying!!!😘

[lindacdsissy]

Always so excited when I slip some stockings on

[rebeccacrossdressa]

I just love this video, it really shows the joy I experience when crossdressing. Rolling the stockings up my legs, fastening the garters, then slipping into a dress or skirt. I always save the absolute best part for last too- slipping my silky, stockinged feet into my high heeled pumps! Then of course walking over to look at myself in a full length mirror and marvel in the finished product.