Crossdressing journey

[Danskos44]

I say buy it, wear it, enjoy it! I am older (70) and I know I would never pass for a woman. But that’s not what wearing lingerie is for me. I love the feeling of satin or nylon against my skin. It makes me feel feminine and submissive…I have never been with another man (married too long) . But my wife begrudgingly accepted my fetish and I am okay with that.

Like PinkOanties4me, At 69 and recently remarried, I have aged out as well, and purged everything for the last time, but I do have some fond memories, reflections and observations on my years as a closet bisexual crossdresser:

Prep time for dressing to host vs. dressing for self-pleasure varies by about an hour…
Your heart pounding when you first reveal yourself dressed to someone for the first time…
The secret satisfaction of seeing your partners arousal as he looks you up and down, from your wig to your boots….
Waterproof lipstick lasts longer, but it’s a turn on to see your lipstick on the cock you are pleasuring orally…
Pulling my wig into a ponytail to keep the hair out of my mouth when going down - and the “Oh crap!” moment when the guy you’re blowing inadvertently grabs your wig off your head…
Getting the cum stains out of that nice black turtleneck before they get crusty!
The fake eyelashes that end up down on your cheek during sex….
Thigh highs are the better choice than pantyhose if you are bottoming while dressed…
Reaching back to hold on to your 4” heels while performing a “hands free” blow job…
The cool breeze on your back side as the skirt gets flipped up and the panties come down…
Becoming so comfortable wearing heels that you forget you’re wearing them... until you take them off...
Although I have moved on from all of this, I still have years of memories and experiences to masturbate to when the mood hits me….! It was all a lot of fun, and I have no regrets!

 

[Cumpup39]

I’m not passable, but love being the obvious guy in a skirt and bra that gets to serve Men!

 

[Lez13]

I’m not passable, but love being the obvious guy in a skirt and bra that gets to serve Men!

A person after my own heart I couldn't pass as a girl but it don't stop me from wanting to be one

 

[wifes_fag]

Done it a little for another boy in school. I would also get dressed and go to this area at the city lake. Got braver and braver and would walk around. Nobody really seemed to notice. It felt great. After I got married my wife loved sex. We got to doing threesomes. One guy made me his sissy and I had to start wearing dresses. Wife loved the kink. We would go places on the weekend sometimes with me in a dress. We would go to Dallas or Tulsa to meet our guy with others and I would go dressed. He required it. We went to Dallas and I didn't take a single boy clothes. It was good for the mind though knowing I had no way out. I dressed as a girl a lot through my twenties and thirties. A few local people even knew about me.

 

[cureustoo]

I wore the inevitable marks from the bra strap with pride when I looked in the mirror.

 

[eaee]

Reading through the posts brings me to understand a friend, well, ex-friend, who'd had surgery, wore a wig, but could not pass.
"She" sorted offered me the use of her pussy. I declined as the appearance was much too masculine. I felt badly for "her".

 

[BillyWalrus]

Reading through the posts brings me to understand a friend, well, ex-friend, who'd had surgery, wore a wig, but could not pass.
"She" sorted offered me the use of her pussy. I declined as the appearance was much too masculine. I felt badly for "her".

Have you been to your local Wal-Mart? A lot of women don't pass. My Filipina trans gf is more feminine than about 80 to 90% of the women here.

 

[cureustoo]

Fresh out of the shower. Put on a pair of brazilin back bikini panties, thigh highs with a garter belt, bra under my sleep shirt.

 

[kimjohnsoncd]

I think we all know the path. Obtain clothes, makeup, heels etc., toys too. Life happens. Purge. Repeat. And then somehow the years go by. I may have passed for a bit of time. No longer. I may have been able to handle 4 and sometimes higher heels, but now I don't want to often. I still appreciate and want to dress in sexy lingere and clothes but who am I kidding. And I'd love to be loved, to make love and have someone make love to me, but that gets less likely with each passing year. Memories are still there. Great memories.

 

[Aleisterwolfe]

I’m just starting down the road of being a cross dresser. Honestly I’m excited and scared to death. Love hearing all of your experiences.

 

[OpenRoad_71]

I’m just starting down the road of being a cross dresser. Honestly I’m excited and scared to death. Love hearing all of your experiences.

Hiya! Just accept yourself is all I have to offer, don't berate or belittle yourself cos you have an interesting quirk! Love who you are.

 

[Flyover3]

I’m just starting down the road of being a cross dresser. Honestly I’m excited and scared to death. Love hearing all of your experiences.

Honestly I’m excited and scared to death. Me too, I want to look like a woman and I want to feel like a woman.

 

[cureustoo]

I bought a couple bras, garter belt and a pair of 1.5' heels. It will be awhile before they are delivered since I got them online.

 

[Shaglus_Ziegler]

Are you a crossdresser, or maybe 'crossdresser curious', or even just a chap who likes to wear woman's clothing?
The journey is different for all of us, although there is a common moment: that first time we put on a garment of woman's clothing. Some of us felt guilty, some didn't, but for all of us who went on to accept the label "crossdresser", it felt right.
My journey was one of guilt and longing: guilt when I acted on my desire to crossdress and longing when I didn't. I threw away so many lovely garments: dresses, panties, body stockings. And dildos too of course
But now I don't mind saying: I am a crossdresser. I am Alison. And my male side too of course. We coexist comfortably.
I am at the point in the journey where the guilt is gone and I am accepting and enjoying my kink: i recently went to a men's suana in full makeup and dressed to kill. I flirted and flashed, and I loved it, can't wait to go back.
I have no idea where my journey is leading, I am excited and a bit nervous to find out.
Some of you are further along than me - what happened next? Where might I go from here?
And for those of you earlier on in the journey - how are you doing? What is your next step? Are you comfortable or still feeling guilty?

I think it can be very sexy and I am attracted to certain crossdressers. Sexiest part is when the person fully embraces it. Go for it!!

 

[Nadinet]

started v young with my older sisters bras, quickly progressed to her panties and tights and eventually dresses and makeup... soo exciting...
love to dress, especially in something borrowed, sadly not convincing but love to be en femme

 

[gurlsynthia]

I love to cross dress. Started in my mid twenties with my wife’s panties.

 

[cureustoo]

I woke up this morning wearing the beige lace cheekies, half slip and a teddie that I slept in...........

 

[Oshkosh60]

I love slips

 

[gurlsynthia]

I love slips too, both full and half. I remember Elizabeth in “Cat on a hot tin roof” spent most of the movie in a slip. Very very sexy.

 

[CDsuzie69]

I’m just starting down the road of being a cross dresser. Honestly I’m excited and scared to death. Love hearing all of your experiences.

Enjoy the journey, it's great sexy fun, but you're not sure where you're going which makes it exciting. Whatever enjoy the ride xx

 

[CharlieBoker]

I wouldn't call myself a cross dresser, but way back in my teens I had a much older lover in his sixties who liked me to dress in ladies panties for our meetings.

I would often already be wearing a pair of my girlfriend's panties under my jeans when I knocked his door.

Knowing I was going to suck his cock and probably get fucked was enough to get me shaking with anticipation, but the extra kink of wearing the underwear for him upped the arousal level for me.

On one occasion he had me wear silk hold up stockings while he fucked me missionary on a chair. We both came super hard that day!

It's not really my thing, I haven't worn anything like that for many years, but I can really appreciate how sexy dressing up would make CD's feel.

 

[RedBear644]

I've always been fascinated by clothes, and a little scared of them. I get so anxious deciding what to wear in the mornings that, over time, I've reduced my closet to just a few outfits that consist of the same pants, shirts, socks, etc just in different colors. The idea of getting a slightly different fabric on a favored pair of jeans makes me legitimately sad.

But...

I was in a theatrical performance a few years ago that had me in women's clothes for more than half the runtime, with lots of quick changes, and I needed to know that I wouldn't flash the public accidentally, so I bought my first set of thongs. Cheaply made, 100% cotton, shrank like the dickens in the dryer, but gee wiz, they're a lot of fun. I started wearing them for the entire day leading up to performances. It wasnt even a sexual thing, I kept telling myself, just be the method actor to get the show right, right?

I kept the thongs at the back of my underwear drawer for the next few years. The multi-pack came in lots of colors, but I gravitate toward the black and pink.

My job started offering remote days, and I found myself lounging around the house in the thong and a tee, no pants. I bought a floor-length skirt (with pockets!) to have some place to hold my phone while moving around the house.

Recently I gave myself permission to go full-bore and I went on a bit of a spree at the big box store around the block from my house. I bought panties, bras, a bikini, flouncy blouses with long sleeves for yard work, nylons, fishnets, knee-hugh socks. I learned the difference between mini- and micro-skirts lol! I even turned a pair of old jeans that I've been saving for a time that my waistline will probably never see again into a pair of cute cut-offs. I like that the pockets are visible, and of course I cuff the hem because bi millennial

Now when I get home, I rush to put on a bra while my wife rushes to get hers off. I sleep in mine, and I miss the feeling of it during the day. I wear fishnets under my pants every other day, just to remind myself of the sensation.

Cross-dressing has allowed me to put my hair down, so to speak. I now look forward to crafting new looks using the wardrobe pieces I have, and I think about what to buy next. Something that used to paralyze me with fear is now something that I embrace and love about myself. I'm not sure where this is going yet, but I do know that it feels RIGHT.

 

[Crios]

I've always been fascinated by clothes, and a little scared of them. I get so anxious deciding what to wear in the mornings that, over time, I've reduced my closet to just a few outfits that consist of the same pants, shirts, socks, etc just in different colors. The idea of getting a slightly different fabric on a favored pair of jeans makes me legitimately sad.

But...

I was in a theatrical performance a few years ago that had me in women's clothes for more than half the runtime, with lots of quick changes, and I needed to know that I wouldn't flash the public accidentally, so I bought my first set of thongs. Cheaply made, 100% cotton, shrank like the dickens in the dryer, but gee wiz, they're a lot of fun. I started wearing them for the entire day leading up to performances. It wasnt even a sexual thing, I kept telling myself, just be the method actor to get the show right, right?

I kept the thongs at the back of my underwear drawer for the next few years. The multi-pack came in lots of colors, but I gravitate toward the black and pink.

My job started offering remote days, and I found myself lounging around the house in the thong and a tee, no pants. I bought a floor-length skirt (with pockets!) to have some place to hold my phone while moving around the house.

Recently I gave myself permission to go full-bore and I went on a bit of a spree at the big box store around the block from my house. I bought panties, bras, a bikini, flouncy blouses with long sleeves for yard work, nylons, fishnets, knee-hugh socks. I learned the difference between mini- and micro-skirts lol! I even turned a pair of old jeans that I've been saving for a time that my waistline will probably never see again into a pair of cute cut-offs. I like that the pockets are visible, and of course I cuff the hem because bi millennial

Now when I get home, I rush to put on a bra while my wife rushes to get hers off. I sleep in mine, and I miss the feeling of it during the day. I wear fishnets under my pants every other day, just to remind myself of the sensation.

Cross-dressing has allowed me to put my hair down, so to speak. I now look forward to crafting new looks using the wardrobe pieces I have, and I think about what to buy next. Something that used to paralyze me with fear is now something that I embrace and love about myself. I'm not sure where this is going yet, but I do know that it feels RIGHT.

How does your wife feel about your cross-dressing? Sounds like she might be very accommodating and non-threatened.

 

[stargame]

I've had a fun journey. I started wearing my twin sister's panties when I was very young. Over the years, i've always loved wearing cute panties. Now, I don't even own yucky guy underwear. I absolutely love all the fabrics, and cute styles. I guess you could call it cross dressing.but I also love being dressed totally feminine. Nothing is so fun as wearing a cute matching bra and panty set. I regularly wear a bra and panty set under my yucky guy clothes when I go out. However, I'd much rather be wearing a dress.

 

[RedBear644]

How does your wife feel about your cross-dressing? Sounds like she might be very accommodating and non-threatened.

So far it's early days, but she's definitely accepting if not outright curious/supportive yet. I tend to move through interests at a somewhat alarming rate, but this feels different. Time will tell.