Biggest guilty pleasure of Crossdressing

[Sabine Janus]

What is your biggest guilty pleasure in crossdressing?

SJ

[Pixie_94]

Simply wanting to do it.

[kimdl93]

I really, really have been trying to set-aside the guilty part :). As far as pleasures go, what I enjoy most is comfortably being out in the real world

[Kris Burton]

Simply wanting to do it.

That, and the erotic pleasure I would experience while dressing. I thought it so wrong so taboo. I have successfully put those things aside, and it feels even better. Now however, the outside world beckons...

[franlee]

I haven't felt guilt in years. And I can't even remember exactly what is was based in other than using my wife and female friends or family's clothes and that really didn't bother me that much back then. Now if anything it's for not indulging more.

[Janine cd]

I used to feel guilty wearing feminine dresses and wigs and makeup because I thought that was unnatural. I have since accepted the reality that my desire to dress totally as a woman is only a necessary part of my being.

[Sporco]

Breast forms and painted nails...

[Karren H]

The simple pleasure of wearing D cup bras and not needing breast forms!

[GenevieveF]

The feeling I get when I slip on a pair of stilettos.

[Debs]

Walking into my favourite bar, all looking at me and they smile, I know I'm safe dressed and feel a million dollars

[CamillaH]

Talking to my wife on the phone while dressed

[MonicaPVD]

Wearing a very tight and sexy outfit in public that is completely out of place for the occasion. Not something I do much at all, but a wonderfully guilty pleasure.

[Paula_56]

Getting dressed to the nines in a business suit, and then slipping my stocking clad feet into a pair of pumps.

The feeling you get when you put a dress on over your head and falls down around your breats and lingerie,

[Stephanie47]

Well, it is definitely a thing in the past and definitely off the shelf in the future. When our daughter lived out of state my wife would visit her for seven to ten days. Now our daughter lives forty miles away. She would also visit her cousin in Arizona for a week. Now, her cousin lives in a care facility. No more trips. When she traveled I was able to hang a nice selection of dresses and slips in the walk-in closet; line up heels at the foot of the bed; stock panties and bras in my armoire. It was 24/7 and evening drives and strolls. Pre-Covid my wife did babysit overnight at our daughter's apartment. Covid has killed even that opportunity.

[StaceyJane]

Putting on a bra that fits without forms or stuffing.

[Debs]

Stacey, Ive got one of them, amazing, and where the hell do i get another one ?

[WillowHanna]

The fact the my wife seeing me in panties turns her on a much as she turns me on. We lounged around the house all weekend, just us , in our panties. It was splendid!

[Lori Ann Westlake]

I fortunately succeeded in dumping the "guilt"--or rather, the shame--decades ago. But... greatest pleasure? Today I'd say it's fantasizing while dressed as a woman.

In years long past, especially in my teens when my dressing was more fetish-oriented than it is today, there was one supreme pleasure I remember. I would get completely dressed in a bra, garters, nylons and heels, slip, skirt and blouse--everything, in short, except the panties. Then, feeling "almost" dressed, I would delight in slipping the cool, silky panties up my nylon-clad legs, drawing them up underneath me and settling them around my waist. fully dressed now in women's clothing and women's underwear. I was "saving the best until last," as it were. It was always a delicious moment.

[docrobbysherry]

It USED to be the sex!:o

But, since I'm 78 now? I consider ANY sex to be a good thing!:devil:

[mbmeen12]

What is your biggest guilty pleasure in crossdressing?

Impure thoughts.....

[Kelli_cd]

It would be that I just feel "good" or "better" when I'm in bra and panties.
Self confidence has never been an issue, but I seem to have more when I'm wearing.
In earlier years, the sexual desires were a driving factor. Now, well, this is just me, and I'm happy with me.

[alwayshave]

I have not felt guilty about my dressing in a long time. But my guilty pleasure would be open bottom girdles.

[Monique65]

Standing in front of a full length mirror admiring the reflection of a beautiful woman.

[josie_S]

I feel a little sheepish saying this, but the way my butt POPS when I put on heels, especially in skirts

[NancySue]

I?ve been dressing for so long, I have absolutely no guilt feelings. Even after all this time, like Stacey Jane, I experience pleasure daily when I put on my bra that fits perfectly with no forms or padding. Slipping on my panties and thigh highs is very nice, too.

[JaclynL61]

As others have stated, I've tried to get over the guilt / shame of the crossing. Now I would say the guilty pleasure would be shopping and spending too much money on some nice clothes.

[Charlotte Haynes]

Mine is ABBA

[Monique65]

Shaving my face while wearing matching bra and panties.

[XemmaX]

learning to really not care what strangers think!

[Alana Westenra]

Mine is ABBA

:) Same! My biggest GP is the music I put on while dressed; stuff I'd never listen to otherwise!

[Raychel]

Biggest guilt pleasure for me would be the fact that I truly enjoy to be dressed in a dress and forms.
And When I look in the mirror, I think I look better in a dress, then dressed as Ray

[Denice]

learning to really not care what strangers think!

^^^^^^This!!^^^^^^^^

[falcongts]

meeting a guy while dressed was wearing this had a great time but he moved away would like to try again sometime
323745

[April Rose]

Even though I dress practically every day at home I am not out to more than a few people. If there weren't a degree of embarrassment or shame still surrounding it, why am I not out to everyone? So I think my guilty pleasure is crossdressing itself.

[KatieV]

Being hit on by Black men. It happens quite often, I do not know why. Walking down the street, driving in my car. They compliment me, ask me if I?d like to join them for a drink, try to pick me up. I have always said no ? but I am flattered!

[Just Dana]

Mirrors. :o

[Tirzah]

Having way too many options of cute clothes to shop and spend money on. Guy's clothes are so boring in comparison.

[AnelineM]

I'm not out to my wife, so everything crossdressing is a guilty pleasure for me. That said, my greatest guilty pleasure is shopping for womens clothing and makeup and CD accessories online. I love looking at all the options and colors and styles.

[DanielleDubois]

My guilty pleasure is looking into the mirror on one my Danielle boudoir/lingerie days and seeing a woman staring back at me... well, if I squint my eyes a lot:heehee:

[MiniRock]

I have not felt guilty about my dressing in a long time. But my guilty pleasure would be open bottom girdles.

Ooh yes please!

[SaraLin]

Probably my biggest GUILTY pleasure - is this forum.
My wife doesn't want me "talking" to others about this part of me, but I know that if I don't vent somehow, I'll have a melt down.

Being among friends - even if only virtually - really helps me maintain balance.

[Davina2833]

Hi Minirock and alwayshave,

We could always start a club...

Davina

[Erin Lafleur]

Ooh yes please!

Just ordered my first vintage open bottomed girdle today, can't wait! I love pretty, lacey garter belts but they're just not up to the task (even with stayups).
Lace top nylons are one of my favorite items to wear but also my nemesis and I refuse to give up without a fight!

[JustJennifer]

Mine is ABBA

Their new single "Don't Shut Me Down" has been playing in a loop in my head for weeks now...

And now you see another me, I've been reloaded!
I'm fired up, don't shut me down!

[MonicaPVD]

Happens a lot. I have a theory, and it is a combination of two factors. First, the fact that crossdressers and transwomen are endlessly fetishized in the media and degraded by porn tropes. Second, the fact that urban black men tend to be a lot more at ease with exploring their sexuality ON THE DOWN LOW. What does this mean? Many guys see a crossdresser and instantly think, "easy sex". Black men, in my experience, are more likely to verbalize that thought than white men.


Being hit on by Black men. It happens quite often, I do not know why. Walking down the street, driving in my car. They compliment me, ask me if I?d like to join them for a drink, try to pick me up. I have always said no ? but I am flattered!

[CarlaWestin]

Being in the company of a sexy hot woman that know's what I'm thinking.
And she's within reach and doesn't mind.

[Genifer Teal]

I do not believe the title is meant to suggest the same kind of guilt we often associate with dressing. For me an answer might be regular mani - pedi appointments.

[Alexis00]

Biggest? Big (D) boobs!

And obsessed with bras. First bought unwired bras. Then padded cup bras. Then sports bras. Then underwire lace bras. Then lace cup bras without wires with small cups for underdressing. Then lace cup bras with wires with small cups to try and give me some shape without forms for underdressing.

Now Obsessed with matching bra and panty sets.

[MiniRock]

Hi Minirock and alwayshave,

We could always start a club...

Davina

Let's start a picture thread Davina. Erin can be first because she already has one. And of course Jamie. I'll have to get one and it'll have to wait until I get back to Vienna at Christmas where all my things are. But I'll definitely post in due course.

[Vintage4sarah]

There are so many guilty pleasures that all of you wonderful ladies are sharing that so many of us can relate to while enfemme. I certainly can share with many of you. But, my greatest pleasures are based around doing my best to create my female image and then be out and about in public settings or other venues with other Tgirls, real woman or those special gentlemen admirers. Having dinner with a special gentleman, chatting, strolling arm and arm, and having the sensation of being treated like a woman would be at the top of the list.

[Maria 60]

I believe mine would be sitting on the couch and watching TV with my wife. Turning to her and give her a smile and she smiles back and then I look down and see that I'm wearing a full slip nighty with thigh highs bra and breast forms and a silk pink robe. Still after all these years in great disbelief and guilty pleasures.

[Rhonda Darling]

Inhaling that fresh air of heady expectation . . . and
Exhaling that sweet sweet breath of sublime joy and satisfaction.
There?s nothing else like it.

[prene]

My breast forms?
I have some but not big enough.

Prene

[Jane G]

Switching from plain Jane to sexy Jane. I'm very comfortable with my dressing it's just part of life, but every now and again there are special moments that still are guilty pleasures.

[Abbyru1]

seeing toe nails with polish; shaved legs in nylon under a skirt or dress or shorts ; a nice top or blouse and know that I'm viewing MYSELF not somebody else.

[Natalie5004]

Your avatar shows that you are well endowed, Prene.

[Jessica Secret]

Beautiful/romantic/bridal lingerie & sleepwear. Nothing like it.

[Visitor]

The simple pleasure of wearing D cup bras and not needing breast forms!

The brassiere I'm wearing at the moment has C cups that hold and shape very real breasts and the pleasure you feel is one I enjoy immensely. I love the look and the feel. I always thought of myself as a breast man... only half aware that I enjoyed putting on my own brassiere as much as I enjoyed taking my partner's brassiere off. What a strange world this is.

[Linda K.]

Being able to stay dressed for hours. I am most comfortable and relaxed when I am dressed. :daydreaming:

[Christina89]

Being able to come home after a long g work day or regular work day and just putting on a look or pj's and feeling nice and relaxed. Feeling my issues and anxiety go away

[DianeT]

Watching my legs with heels on the table while lounging and watching TV. So superficial, and yet it entertains me to no end.

[Chloe from Colorado]

Seeing the woman staring back at me in the mirror, the care and time my wife puts into making sure every part of my makeup, hair and outfit is just right, and the feeling when she makes me "feel like a woman"!

[denese]

would love to message or email . i am in copperas cove

[Veronica Lacey]

The term "guilty pleasure" I read as not actually feeling guilty for doing so but more that if my wife or anyone else (hypothetically) said hey, you really like this I'd respond Yes, guilty as charged.

So such guilty pleasures include when I have opportunity to put out all my wardrobe in the closet, armoire, dresser, heels on display; I really love that. Having a chat on the phone with people while fully dressed. Forgetting to change out of panties when going out in male mode.

These are just everyday things that remind me that my dressing is normal and unnoticed.

[Beverley Sims]

There is no guilt in my dressing just pleasure.

[kellyanne]

No guilt in my pleasures - I am what I am so I never feel guilt about dressing in panties or in full en femme.

We had boozer's for parents so if I imbibe which I rarely do - that makes me feel very guilty.

[jamienoir]

Happens a lot. I have a theory, and it is a combination of two factors. First, the fact that crossdressers and transwomen are endlessly fetishized in the media and degraded by porn tropes. Second, the fact that urban black men tend to be a lot more at ease with exploring their sexuality ON THE DOWN LOW. What does this mean? Many guys see a crossdresser and instantly think, "easy sex". Black men, in my experience, are more likely to verbalize that thought than white men.


Hey! Never had a black dude hit a me! What gives...

It's usually white dudes lol.

[SarahLynn]

Jamienoir, "Hey! Never had a black dude hit a me! What gives... It's usually white dudes lol."

Must be the reverse effect. White men thinking you are a loose woman. Not sure if that is a compliment. Have to admit, if I saw you out and about, and all by yourself, there is a very good chance I'd hit on you too.


If I looked as good as many of you do in your avatars, that would be a pleasure for me. Not being the case, my guilt is my envy of your great looks.

[Iris Tse]

Being propositioned by a hot bi-couple for a night of debauchery after a few drinks at my fave bar!

[MonicaPVD]

Hey! Never had a black dude hit a me! What gives...

It's usually white dudes lol.

Maybe you need to hang out in more diverse areas. 😂

[jamienoir]

Monica:

I know right lol.

[Patience]

1) Getting a makeover (had 3 so far),
2) Shopping for a wig enfemme while made over, perhaps with the help of a friend,
3) Walking around unapologetically, perhaps enjoying a public event, not giving a toss to what people may think.

...in that order.

[Mackem Sue]

Just the pure contentment I get from it.

A specific pleasure?

Taking a fresh pair of stocking out of their packaging, rolling them up to slide onto my legs, then slowly pulling them on, over my toes and ankles, up my calves, over my knees and finally up my thighs until they can go no further, followed by fastening to the clips of my suspenders and knowing that slight pleasant feeling as the suspenders occasionally tug on the stocking tops as I walk around in my heels.

Sorry, couldn't resist being a tease. 😀

Sue

[Sometimes Steffi]

Sleeping in a bra with forms.

[KymG]

Checking myself out in the mirror, and looking down to see the girls on display.