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Different dressing scenarios - what would you wear?

26 Posts
17 Users
42 Reactions
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Posts: 749
Lady
Topic starter
(@jess92)
Prominent Member     Florida, United States of America
Joined: 4 years ago

I thought this would be a neat topic. I decided to come up with 3 random scenarios and based on your wardrobe and whatever your heart desired to wear, what would you wear in each scenario? Assume there are no restrictions, you won't be recognized, you're not closeted, you'll pass, and no one in your personal life will know it's you. You can wear anything from your current wardrobe plus add anything to your wardrobe you'd like if need be. The goal is to really showcase your dressing talents and individuality for the occasion. You have freedom and are in complete control.

Scenario 1: Formal dinner party   

Scenario 2: A walk on the boardwalk at the beach on a warm summer's day

Scenario 3: A romantic lingerie/sexy pj's sleepover 

My choices:

Scenario 1: A slinky red dress, one of the two I already own, with forms, a wig and heels.

Scenario 2: A bikini top, cutoff shorts, sandals, plus wig and forms

Scenario 3: (my personal favorite!!) A gorgeous lacy/satin/chiffon bridal negligee/robe set with forms, a wig and satin slippers. 

How about everyone else?

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25 Replies
13 Replies
(@lauren114)
Joined: 2 years ago

Noble Member     Delaware, United States of America
Posts: 1209

@jess92 Here's my choices:

1 - An above the knee length black sequin sheath dress with silver metallic strappy sandals.  Since It's formal, I would have my hair, makeup (dramatic smoky eye) and nails done, and I would carry a black beaded clutch purse.   Matching panty and bra set with a thong panty and balconette bra.

2 - A floral print sundress with a pair of platform espadrilles.  Again hair, makeup and nails done but the makeup would be more subtle.  For this one, I'd skip the pra and just wear a thong panty.

3 - A baby doll nightgown with a g-string panty.   I'm feeling this as the afterparty for the formal occasion!

That was fun....I'm going to be thinking about this all day now!

 

 

 

 

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Lady
(@jess92)
Joined: 4 years ago

Prominent Member     Florida, United States of America
Posts: 749

@lauren114 Great choices Lauren!! Heart

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Duchess
(@jennconn)
Joined: 2 years ago

Noble Member     Florida, United States of America
Posts: 768

@jess92 

1, I have a very sexy body con red dress with my 5” heels and my red necklace and earrings.

2.I’d wear the pink sundress that I just bought with my hoop earrings and a pretty pearl necklace.  I’m not sure heels would walk well on a boardwalk though, so I’d have to look for some wedges.

3. I actually have a short lacy red baby doll that I’d wear, but it would depend who was coming to the sleep over! 

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Lady
(@cherylt)
Joined: 7 months ago

Prominent Member     Honesdale, Pennsylvania, United States of America
Posts: 485

@jess92 1: Formal : An off the shoulder A-line cocktail dress. Just below the knee with a full skirt. Red of course, sheer nude hose with lace tops supported by my bustier with 6 garters over my matching bikini panties. Red 4" stiletto sling back open toe heels. Carrying a black patent leather clutch. My hair swept up and off to one side. Red lipstick matching my dress of course.

2: Boardwalk : My hair down and loose, subtle makeup. Wearing a midi length, tank top style summer dress in a pink floral, closely fitted at the bodice and with a full flowing skirt. Wedge sandals and carrying a mid-sized canvas style purse in white.

3: Sleepover : You didn't say with whom but you did say romantic so ...A vintage satin nightgown in soft peach, floor length, fitted bodice with wide lace straps and sleeveless. Subtle lace touches throughout. Matching satin panties and peignoir and white kitten heel slides on my feet. Makeup would be subtle yet intriguing. My scent White Diamonds. 

Now were it a sleepover with the girlfriends ... An emerald green chemise with matching panties and robe. Soft fuzzy slippers, simple basic makeup and loose messy hair. 

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Lady
(@jess92)
Joined: 4 years ago

Prominent Member     Florida, United States of America
Posts: 749

@cherylt Great choices Cheryl, especially the lingerie! I was thinking girlfriends for the sleepover but both scenarios are relevant!

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Lady
(@raven188)
Joined: 6 years ago

Prominent Member     Idaho, United States of America
Posts: 507

@jess92 

1. probably my leather skirt, with my long sleeve semi sheer lace top, all black

2. a swimming suit under a sun dress

3. long satin nightgown in pale blue

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Duchess
(@lizzy89)
Joined: 5 months ago

Reputable Member     GreaterManchester, United Kingdom
Posts: 162

@jess92 1.Has to be a little black dress, sheer tights and high heels. Also red lip stick for a nice glam look.

2. A nice summery floral maxi dress and sandles

3. A nice black nighy and robe.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 4018

@jess92 Scenario 1: an LBD. I have two.

Scenario 2: comfortable walking shoes and a flowy mini dress. I have two.

Scenario 3: won't ever happen. I sleep naked.

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Duchess
(@liza4you)
Joined: 2 months ago

Estimable Member     MICHIGAN CITY, Indiana, United States of America
Posts: 73

@harriette Oh Harrtette, I think your missing the point and the fun of this, Is that really what you would want to do if no one or a special someone where around? if you were free to let go and in a perfect world of no fear of rejection or discrimination no worry of anyone knowing what you may not want them to know. Jess is setting the stage for you to express what we all feel and you are among people who from what I have seen won't judge you if anything they will encourage you to dream your dreams because that's what were here for I know I am new to the board and I'm only picking on you for #3 I'm dying to hear what you would really wear because I think you have a naughty side there and just afraid to show it psychology teaches naked is just the ultimate state of vulnerability begging to get out. just needs a little encouragement..  Probably a few others I read that really want to let it out too if I am overstepping just say so, sometimes just a nudge can open a floodgate of trapped woman and the whole center spills out with such a release of feeling and self acceptance that at least for a time we feel happy to be and it spreads if I put just a little smile on your face and sent that little twinge I did my duty today ....

 

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 4018

@liza4you Maybe I am just a conservative girl at heart (Hardly, I crossdress, right?).

I haven't worn anything to bed since I was ~15 and, if I started now, my wife would call the white coats on me. 🤣

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Duchess
(@liza4you)
Joined: 2 months ago

Estimable Member     MICHIGAN CITY, Indiana, United States of America
Posts: 73

@harriette Ya, I really do know what you mean, support can mean so much and it really doesn't take a lot of effort, at least I feel that way. I am not able to put myself in her emotional shoes (however I could put myself in her shoes but she really doesn't like that so I just got a pair for myself..she still looks better in them than me but doesn't believe me when I tell her that)

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Duchess
(@liza4you)
Joined: 2 months ago

Estimable Member     MICHIGAN CITY, Indiana, United States of America
Posts: 73

@jess92 1- Formal,A nice 2 pc leather Skirt Suit, corset, depending on the occasion light brown for a day function, medium length light brown hair modest but memorable makeup nothing too flashy. probably heels or open toe short boots to match the outfit.2-3 ". maybe a necklace smaller ear rings and a minimalist watch and small leather clutch. for a pm function it would be a dark brown or burgundy but a little longer and darker hair, same for the makeup it would be deeper and capture the night more , probably accent the eye line a little more, some cats eye lashes done with taste but just verging on the daring i would want to leave a little more of a lasting impression, the necklace would be a bit heavier maybe even a classy choker and definitely knee length or higher matching boots nothing less than 4 1/2" or more.  much longer earrings maybe even pearls if the mood was right, my makeup would be bolder, lipstick deeper red maybe a little plumping. Just a hint of pout but fully in control.  and sunglasses for the added touch.

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(@Anonymous 100087)
Joined: 2 months ago

Reputable Member
Posts: 304

@jess92 

dinner party: my nice dark green dress with a slit to show off you leg. my snake skin open toe sandals with heels, painted toes and finger nails, probably pink or red color. blond wig, fake dd breast. star earrings, pink anklet, black choker.

for the beach: bare foot, painted toes and fingernails, blond wig, anklet, fake breast and a thong bikini

sleep over: nothing. i don't have any night wear. i sleep naked Smile  

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Posts: 2111
Hostess
(@cdsue)
Famed Member     Delaware, United States of America
Joined: 5 years ago

Jess -

What a fun idea - here are my thoughts:

1- formal dinner party - starting form the inside out - lace panties, high waist open bottom girdle with garters, black stockings, push up bra with lace trim, black sequined empire waist gown with knee high slits on each side, black 3" sling back heels, choker necklace, cameo broach, faux diamond drop earrings, bob wig (salt and pepper), faded black eye shadow and red lipstick (along with the other usual make up). Oh I forgot a Pandora bracelet with charms appropriate for the time of year or function (I love those) and a couple of different rings. Needless to say both fingers and toes would have red nail polish.

2- a walk on the boardwalk at the beach on a warm day - a one piece bathing suit with a sheer sarong knotted over one shoulder and draped over me, a pair of sandals with a slight heel, wife brimmed hat and large frame sunglasses, carrying a straw bag, dangling dolphin earrings and a necklace with a dolphin charm, a beach themed ankle bracelet, toe nails painted in an aqua glitter color  and fingers the same.

3- a romantic lingerie/pj sleepover - this one is tough - my black lace baby doll with embroidered flowers and lace trim with the sheer black panties with embroidered flowers and ruffles on the butt, wig, hoop earrings, lipstick ( a red or pink), red mule slippers with a slight heel and a knee length sheer black cover up.

That was fun. I look forward ot seeing what others have to share.

XOXO
Suzanne

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1 Reply
Lady
(@jess92)
Joined: 4 years ago

Prominent Member     Florida, United States of America
Posts: 749

@cdsue Excellent choices Suzanne!! And that baby doll nightie sounds very sexy!

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Posts: 79
Lady
(@wendye47)
Estimable Member     Clwyd, United Kingdom
Joined: 9 months ago

Great topic! Here are my choices…

Scenario 1 - Dinner Party

6 inch black high heels with ankle straps, black shiny stockings, ankle bracelet, black girdle with 8 suspenders, red panties, red knee length sparkly dress, black choker necklace, drop earrings, blonde shoulder length wig, red shiny lipstick, velvet eye shadow & red nail polish in hand and toe nails.

 

Scenario 2 - Boardwalk: One piece red bathing suit, Silky dark green sarong, 2 inch heeled sandals, black wig, red lipstick, floppy hat & large sunglasses.

 

Scenario 3 - Romantic Sleepover: Black negligee, 4 inch heels, sheer black stockings, choker bracelet, black lipstick and red wig.

Wendy xx

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Posts: 255
Lady
(@helenmariehayley)
Reputable Member     Kent, United Kingdom
Joined: 7 years ago

Hello Jess,

What a good idea, love the scenarios.

1st the formal wear,

Black bra/knickers & black suspenders with black stockings, my blue lacey evening dress with my black 2" heels. Full make up with my blonde hair.

2nd the Boardwalk,

White lacey bra/knickers & a lovely flowery summer dress, no tights & some white pump shoes.

3rd romantic sleepover,

My sexy pink/frilly baby doll nightie with matching frilly pink knickers & not much else, well so red lipstick.

 

love   Helenmarie

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Posts: 2172
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 5 years ago

I am kind of cheating since I have already fulfilled all three senareios.

1) Black just below the kness dress, a classic LBD. Black stockings with matching set of black lace bra, thong and garters. Breast forms to swell my boobs and a pearl necklace to lay against and accentuate my boobs. Wig and lip stick ro finsh off. I did not, but would add a make over to fulfill the challange.

2) walk on the beach/boardwalk. I wore a long black floral skirrt with tropical flower print, black top with a large keyhole cut out, white sandals, a wig with a large brim hat and red lipstick and nails. Underneath it all was a brown and black bikini with a tiger print and of course a lovely set of breast forms, my larger set to get noticed.

3) Here I have so many choices as this is my go to en femme look that I enjoy with my wife often. My favorite is all black lace bra, thong, garters and stockings covered by a sheer black see-through robe. Of coirse breast forms wig and make up. Oh, I almost forgot, three inch black stelletto pumps and red lips and nails.

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1 Reply
Lady
(@jess92)
Joined: 4 years ago

Prominent Member     Florida, United States of America
Posts: 749

@jjandme Great choices JJ! So feminine!

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Posts: 1742
Duchess
(@alison-anderson)
Noble Member     Middlesex county, New Jersey, United States of America
Joined: 6 years ago

You might as well tell me I'm a kid in a candy store, and can only pick out 1 piece. I have about 7 or 8 long formal dresses (several "inherited" from my mom or ex), one of which is actually a skirt, a shell, and a jacket, and another 6 or so cocktail length dresses. I'd probably pick either the purple mother-of-the-bride dress my ex wore to my daughter's wedding, or a similar dress that I took from my mom.

As for the boardwalk, I have about 10 short skirts, another couple of summer skirts, over a dozen tank tops, some sleeveless tops, and 4 sundresses (either tank top or spaghetti strap, all with pockets!), two of which can be seen in my public photos here. I have a g-string gender bending nylon panties that can keep me in place down there yet still be very airy. I could wear a thong over it, and I have even worn it under a bathing suit. Makeup is usually just some beard cover, occasionally adding some concealer or bronzer. I go out like this often in the summer to walk around my block. Whether I wear sneakers, sandals, or wedges would depend on how far I plan to walk and what plans I have later in the day. I probably couldn't decide until the spur of the moment when I say, "I feel like wearing ..." and then find something matching. If I were also going in the water, I would have on a bathing suit underneath and wear my clip-on bangs instead of my wig. Don't forget plenty of sunscreen.

The lingerie party is probably the easiest. I have a white satin empire waist baby doll chemise. The chemise has lace cups that would hold the forms. I'd wear the g-string gender bending panties (I originally bought them for just such a party but it had to be cancelled), and depending on the audience, I might wear a thong over top.

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2 Replies
Duchess
(@liza4you)
Joined: 2 months ago

Estimable Member     MICHIGAN CITY, Indiana, United States of America
Posts: 73

@alison-anderson Now that's what I call a plan and backup, I love it..

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Duchess
(@alison-anderson)
Joined: 6 years ago

Noble Member     Middlesex county, New Jersey, United States of America
Posts: 1742

@liza4you Or a large wardrobe. 😀 

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Posts: 289
Lady
(@rosiebeth)
Reputable Member     New York, United States of America
Joined: 5 years ago

1 a tee length off the shoulder white gown with sling back heels with a short dirty blonde wig.  

2 a Hawaiian style apricot dress with sling back cork wedges with a curly blonde wig and a sun hat with scarf.  

3. Love a bridal corset with garder belt and hosiery with sling back stilettos.  

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Posts: 162
Duchess
(@sophie85)
Estimable Member     New Jersey, United States of America
Joined: 2 years ago

1 - A long sparkly black figure hugging long sleeve gown with a plunging neckline, low back, and a front slit that goes above the knee.  Would wear 4 or 5" silver sparkly heels.

2 - An above the knee halter dress in teal, fushia, or a floral print with 3" wedge sandals.  Would consider having a two piece swimsuit on underneath with a triangle swim top and bikini bottom.

3 - A long black gown with a low v neckline, lace bodice, long side slit, and matching robe.

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Posts: 1839
Baroness
(@annaredhead)
Famed Member     Cornwall, United Kingdom
Joined: 11 months ago

1. one of my evening dresses

2. a swing dress

3. long satin nightie

 

Each with sheer stockings and matching lingerie

Hugs,

Anna xx

 

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