Advice On How To Dress For Meeting

[Mahogany]

Hi,

I’d never thought much of dressing like a woman, not even as a goof on Halloween.

But my wife cheated on me last year and I felt humbled (cuckolded), and in a reaction I’d not have imagined, I wound up acting up on my new-found curiosity and gave my first BJ (three months ago).

I showed the guy a slide-show of my wife during it, and he talked dirty about her, and I basically experienced submitting to a more dominant man.

The whole thing messed with my head but has definitely resonated since, and he’s recently emailed me that he’s going to be back in town, and wants to do it again.

But in his emails, he talks about bringing more of the woman out in me…how he wants to call me by my wife’s name etc and asked if I've ever dressed like a woman.

And while I’m not turned on by dressing like a woman per se, it’s just an added out-there-ness, like a new level of submission, that in an inexplicable way, turns me on.

I’ve also wondered if it would allow me in a weird way, to be less self-conscious, like it’s not me being a slut, but this pretend alter ego.

And the more I thought about it, I think I could actually make a passable decent looking girl. I get characterized more-pretty boy than handsome and 6 feet tall but thin & small frame.

I already bought a brunette wig online, matching my wife’s hair style and some lipstick, and get turned on, looking at myself in the mirror, imagining this.

My wife has big breasts so I’m looking at fake tits, without breaking the bank on getting ultra realistic.

But I’m kind of clueless when it comes to shoes, dress, (stockings), and make-up that I might not have considered.

I’m not going to be waxing anything, but I'm definitely less hairy than the average guy and will definitely shave right beforehand. And I kind of feel like if I’m going to do this, I want to look as sexy for him as I can, so any advice/feedback would be appreciated.

 

[MysteryBi]

Hi,

I’d never thought much of dressing like a woman, not even as a goof on Halloween.

But my wife cheated on me last year and I felt humbled (cuckolded), and in a reaction I’d not have imagined, I wound up acting up on my new-found curiosity and gave my first BJ (three months ago).

I showed the guy a slide-show of my wife during it, and he talked dirty about her, and I basically experienced submitting to a more dominant man.

The whole thing messed with my head but has definitely resonated since, and he’s recently emailed me that he’s going to be back in town, and wants to do it again.

But in his emails, he talks about bringing more of the woman out in me…how he wants to call me by my wife’s name etc and asked if I've ever dressed like a woman.

And while I’m not turned on by dressing like a woman per se, it’s just an added out-there-ness, like a new level of submission, that in an inexplicable way, turns me on.

I’ve also wondered if it would allow me in a weird way, to be less self-conscious, like it’s not me being a slut, but this pretend alter ego.

And the more I thought about it, I think I could actually make a passable decent looking girl. I get characterized more-pretty boy than handsome and 6 feet tall but thin & small frame.

I already bought a brunette wig online, matching my wife’s hair style and some lipstick, and get turned on, looking at myself in the mirror, imagining this.

My wife has big breasts so I’m looking at fake tits, without breaking the bank on getting ultra realistic.

But I’m kind of clueless when it comes to shoes, dress, (stockings), and make-up that I might not have considered.

I’m not going to be waxing anything, but I'm definitely less hairy than the average guy and will definitely shave right beforehand. And I kind of feel like if I’m going to do this, I want to look as sexy for him as I can, so any advice/feedback would be appreciated.

I think this is a wonderful thing you are doing. He's gonna love having his cock in your mouth again. If you were a real man what would you like to see your woman look like? There are lots of shoe stores with larger sized women's shoes and its not uncommon for a male to buy female clothes and shoes. Why not go out and make a day of it? Does your wife know? Would she like to come along and have a girls shopping day? Flats might be best since you are tall. Is your bf tall?

 

[Mahogany]

Thanks Mystery,

I don’t have some weird psychologic thing going on of wanting to be my wife, but I figured if I’m going to do this, and since I can semi-pull it off, why not try and look like my wife while doing this.

My ideal BJ to get would be from my wife, on her knees, in just lingerie, but I'm afraid I would look more ridiculous than sexy that way, so I’m debating either a summer dress/cocktail dress or skirt/top.

Either way, I was thinking pink as that’s what the guy suggested, and there’s no arguing that pink’s not girly, which punctuates it I guess.

I also just got fake silicone breast forms that I’ll wear as a vest, and was impressed, cause from a distance, they look quite realistic.

But while the top of the vest is skin color, it doesn’t match my own skin color close enough, so I can’t have something with a lot of neckline.

So I was thinking either a long-sleeve pink top (my nipples protruding through) and a white or black skirt...OR a pink sleeved crochet lace dress…it’s kind of mesh on the neckline and sleeves so the breast vest would look normal & no arm hair would be showing (not that I'm that hairy).

I think you’re right about wearing flats and I'm looking at pink flats with a bow…and also thinking pink tights just to complete the look.

He also wants me wearing my wife’s lipstick and perfume, and I did just order a bottle. But my wife doesn’t wear much makeup in general, and I haven’t a clue about eye liner, so probably going to just make sure to be ultra clean-shaven.

Anyway, I’m not brave enough for stores & shopping for everything online, so certainly not making a special outing of it. And if I were, the very last person I’d go with would be my wife. I know I probably act less confident around her ever since I learned what happened, but she certainly still thinks of me as a man – and wouldn’t able to process me dressed up like that, let alone, doing what I was doing.

But it’s also that craziness, like how insanely at odds it would be with her perceptions, that adds mentally to the turn-on, like I’m being more out there, and a bigger slut than she was.

Anyway, I don’t want to ramble too much, and do have time to think about still, and appreciate your feedback Mystery, and going to just dress in a way my gut tells me would look most sexy for him.

PS - ive never done nail polish, and just wondering, if there's any that remove very easily afterwards.

 

[indiana hubby]

Your bf will love it. Be prepared to totally submit to him

 

[jbalk20]

Thanks Mystery,

I don’t have some weird psychologic thing going on of wanting to be my wife, but I figured if I’m going to do this, and since I can semi-pull it off, why not try and look like my wife while doing this.

My ideal BJ to get would be from my wife, on her knees, in just lingerie, but I'm afraid I would look more ridiculous than sexy that way, so I’m debating either a summer dress/cocktail dress or skirt/top.

Either way, I was thinking pink as that’s what the guy suggested, and there’s no arguing that pink’s not girly, which punctuates it I guess.

I also just got fake silicone breast forms that I’ll wear as a vest, and was impressed, cause from a distance, they look quite realistic.

But while the top of the vest is skin color, it doesn’t match my own skin color close enough, so I can’t have something with a lot of neckline.

So I was thinking either a long-sleeve pink top (my nipples protruding through) and a white or black skirt...OR a pink sleeved crochet lace dress…it’s kind of mesh on the neckline and sleeves so the breast vest would look normal & no arm hair would be showing (not that I'm that hairy).

I think you’re right about wearing flats and I'm looking at pink flats with a bow…and also thinking pink tights just to complete the look.

He also wants me wearing my wife’s lipstick and perfume, and I did just order a bottle. But my wife doesn’t wear much makeup in general, and I haven’t a clue about eye liner, so probably going to just make sure to be ultra clean-shaven.

Anyway, I’m not brave enough for stores & shopping for everything online, so certainly not making a special outing of it. And if I were, the very last person I’d go with would be my wife. I know I probably act less confident around her ever since I learned what happened, but she certainly still thinks of me as a man – and wouldn’t able to process me dressed up like that, let alone, doing what I was doing.

But it’s also that craziness, like how insanely at odds it would be with her perceptions, that adds mentally to the turn-on, like I’m being more out there, and a bigger slut than she was.

Anyway, I don’t want to ramble too much, and do have time to think about still, and appreciate your feedback Mystery, and going to just dress in a way my gut tells me would look most sexy for him.

PS - ive never done nail polish, and just wondering, if there's any that remove very easily afterwards.

There is nail polish remover that you can use to remove the nail polish after your meeting.

 

[Sissyjohn]

The same sort of thing happened to me the more my wife went with other men the less of a man I felt like. Started off with just wearing panties and within a year I was wearing a corset, stocking and suspenders 24/7 even wearing them to bed

 

[BigdaddyToronto]

dont over do it.
trannies look ridiculous when they try too hard to look like garish cheap prostitutes.

 

[sissymaidcherie]

He wants you to be his sissymaid. There are a few websites to buy the outfit.

 

[MysteryBi]

i hope this is progressing...

 

[fuckmywifeinnj]

You don't say if your BF is bi or gay? I suggest you ask him directly; if he is bi he may want to have sex with your wife. If he is gay, he probably wants you to be his gurl friend, his "woman" or his "wife"; and satisfy his sexual needs as a CD partner. In any event, being a "sissy", cuckolded husband is all about you being submissive and accepting humiliation. It sounds like you are not going to be having sex with your wife in the foreseeable future; therefore, I suggest you get used to your new life status. Sooner or later, he is not going to be satisfied with just using your "forward facing" hole and will want to fuck your "male" pussy.

You cannot, and should not try to be a perfect "woman" when it comes to dressing up or wearing a wig or make-up. Try to satisfy your BF's desires without being to concerned about achieving perfection. Be open to experimenting with kissing, hugging, petting, etc. To be a successful CD, you must remember that all your future BFs will want to see male sex organs when you ****** your crotch area.

As far as dressing like a woman, here are some photos of me in my "alternate" identity. To my way of thinking, to achieve success as a slutty CD, nothing beats a pair of black thigh-high nylon stockings.

 

[Sandy Row]

Thanks Mystery,

I don’t have some weird psychologic thing going on of wanting to be my wife, but I figured if I’m going to do this, and since I can semi-pull it off, why not try and look like my wife while doing this.

My ideal BJ to get would be from my wife, on her knees, in just lingerie, but I'm afraid I would look more ridiculous than sexy that way, so I’m debating either a summer dress/cocktail dress or skirt/top.

Either way, I was thinking pink as that’s what the guy suggested, and there’s no arguing that pink’s not girly, which punctuates it I guess.

I also just got fake silicone breast forms that I’ll wear as a vest, and was impressed, cause from a distance, they look quite realistic.

But while the top of the vest is skin color, it doesn’t match my own skin color close enough, so I can’t have something with a lot of neckline.

So I was thinking either a long-sleeve pink top (my nipples protruding through) and a white or black skirt...OR a pink sleeved crochet lace dress…it’s kind of mesh on the neckline and sleeves so the breast vest would look normal & no arm hair would be showing (not that I'm that hairy).

I think you’re right about wearing flats and I'm looking at pink flats with a bow…and also thinking pink tights just to complete the look.

He also wants me wearing my wife’s lipstick and perfume, and I did just order a bottle. But my wife doesn’t wear much makeup in general, and I haven’t a clue about eye liner, so probably going to just make sure to be ultra clean-shaven.

Anyway, I’m not brave enough for stores & shopping for everything online, so certainly not making a special outing of it. And if I were, the very last person I’d go with would be my wife. I know I probably act less confident around her ever since I learned what happened, but she certainly still thinks of me as a man – and wouldn’t able to process me dressed up like that, let alone, doing what I was doing.

But it’s also that craziness, like how insanely at odds it would be with her perceptions, that adds mentally to the turn-on, like I’m being more out there, and a bigger slut than she was.

Anyway, I don’t want to ramble too much, and do have time to think about still, and appreciate your feedback Mystery, and going to just dress in a way my gut tells me would look most sexy for him.

PS - ive never done nail polish, and just wondering, if there's any that remove very easily afterwards.

If you're going to do it you must look your absolute best for him,that's my philososphy anyway,personally I go to a makeoever artist and it would be foundation,blusher,eyeliner,,lipstick and gloss, with false eyelashes but it's easy enough to put mascara on, polish is easy too but as stated in the replies you'll get nail polish remover from any drug store,and you will need it.

I understand you don't want to go to all that effort just saying what I would do,I would also wear heels,guys love heels it's a big turn on for them ,hold ups are a must too,with me the heels and the hold ups stay on at all times,I want them to walk into the room and think 'WOW'

Good luck and please report back with the juicy details,I'm sure he'll love it.

 

[Mahogany]

Hi all,

I saw some more recent replies, and figured during this slow quiet time, I’d give a belated hello & update on how things went with the guy who I dressed up for last summer.

He’s married and lives on the West Coast, but we met up last Summer, a few months after my post.

He’s in his 40s, a decade-plus older than me, and essentially hetero…like he was specifically looking for another guy to blow him while showing off their gf/wife’s photos.

I’d always been 100% hetero (never been remotely attracted to other guys), and had my wife not cheated, I’d never have gone down this weird trippy path.

It started a few months after learning she cheated, with this weird fantasy of having to suck off the guy who screwed my wife.

And meeting the West Coast guy seemed like a way to experience submitting to a dominant man without any real-world f’d up consequences.

The 1st time we met (last Spring), there’d been no talk of me dressing up (I wore reg biz-casual work clothes), but was surreal enough just getting on my knees, showing him photos, and giving my 1st BJ.

I was like “never again” right afterward and paranoid about my wife sensing something in me, like an even greater lack of confidence around her.

But after a couple months, when he emailed that he’d be back in town, I was back to masturbating, imaging myself on my knees again.

It was in those convos, where he started pushing the idea of me dressing up like a woman. He said how I had kind of feminine features and that he’d bet I’d make a cute-looking girl. My initial reaction was “no effin way” but pretty soon I started mentally flirting with the idea.

Like it began with me just trying on my wife’s lipstick. And then pretty soon, I was ordering a brunette wig that matched my wife’s hair length. My wife has nice tits, so I secretly ordered some strap on fake ones.

There was no way I could shave my arms/legs (though not very hairy), so I bought some white stockings, a long sleeve pink top and a pleated white skirt, that looked to me like a cheerleader skirt. I didn’t want to try walking in high-heels, but found some low-heeled once that still were girly.

I would get hard looking at myself at home in the mirror, on a few occasions when my wife was out. But it wasn’t like the clothes themselves, or me in them that had me aroused…had it not been for new plans to meet up…I’d be like get this effin crap off me.

But I’d look at myself getting on my knees in front of the mirror, seeing how I’d submissive I’d look for him, and be rock-hard with anxiousness.

He also wanted more revealing pics of my wife beyond the bikini-vacation photos I’d shown him last time. My wife had some artistic nudes taken last year with a private photographer, so I included some topless ones that I’ve repeatedly jerked off to.

They were personal, and she had them taken more to look back at when she was older, so I definitely felt a little guilt in sharing them. But I also thought how brazenly she’d betrayed me hooking up with the guy at the wedding, with her friends knowing, and me feeling publicly cuckolded.

But the truth was, showing him more of my wife, and the semi-taboo out-there-ness of it, added to the turn-on. And just like weirdly wanting to look like a sexy girl for him, I wanted to show him more, surrender more, and add to the mental dizzying-ness of it.

I guess because dressing up like a girl was his idea (made it less embarrassing), and because I had a better idea of what to expect, I was actually slightly less nervous than the first time we met up. Like I could actually look up and make eye contact with him as we made small-talk beforehand at the bar.

He had me go up to the room to get changed and to text him when I was ready. He’d suggested I wear some clip-on earrings, so I wore a pair of silver (or fake-silver) ones, and wore a fake wedding ring, that vaguely resembled the one I gave my wife.

I was definitely nervous about his reaction, and was kind of grateful, and even happy when he smiled and was complementary, when he said he said I made a cute girl, or that I looked like my wife.

He would call me by my wife’s name or tell me to show him how she sucks, and in a weird way, it made me less self-conscious and less inhibited. Like it wasn’t me on my knees letting my face get slapped, but rather, the character I was playing, like just a submissive role I was acting in.

Unlike the first time, with the wig on, I’d risk making eye contact by looking up. Most of the time he was scrolling thru my wife’s photos and telling me how he was going to fuck her. I think for him, the turn-on wasn’t me or how I looked as a girl per se, but from the power of getting me to dress like a girl and to get me to show my wife for him.

Anyway, I don’t want to get too friggin long-winded and apologize for going on as much as I have.

I definitely had some moments of angst & WTF afterwards, and threw the outfit & shoes away that first week.

He’d also lost his job shortly afterward, was no longer coming East, and there’s also a whole big part of me saying “it’s for the best” and to move the f on with my reg life, and in larger part I have.

But I did keep the wig, and have tried on her lipstick a few times, and can’t say there’s not been times when remembering the experience still gets me hard.

 

[sissy.natalie]

Throwing all your stuff out is called "purging" and we've all done it, and probably more than once.

If you are meeting guys I think the hook is set deeper than you might want to admit to yourself. Is your wife still cheating? It could be time for a really uncomfortable conversation, one that might go better than you expect.

 

[SquirmingSub]

@Mahogany - Thank you for the update. It is always good to have adventures, it has allowed you to learn something about yourself.

As @sissy.natalie indicated, what you did was the simple "purging" that we have all done.

As to your current marriage and what could be a future chapter in life:

• You seem to have had mixed feelings about the specific cross-dressing for another man. Are you able or willing to elaborate more on what those feelings that you have experienced through the year since you initially began down this path?
• I would agree with 'sissy.natalie' in that if your meeting guys that the hook is set deeper than you may have realized or willing to admit to yourself. I know from personal experience, it took me a while before I truly accepted what I truly enjoyed.
• Assuming that your still married, has your wife continued to cheat or have you two had the conversation?
• As mentioned, if you have not had the conversation, it could be time for what you both may consider a really uncomfortable discusion which could allow for each of you to take that next step.

Throwing all your stuff out is called "purging" and we've all done it, and probably more than once.

If you are meeting guys I think the hook is set deeper than you might want to admit to yourself. Is your wife still cheating? It could be time for a really uncomfortable conversation, one that might go better than you expect.

 

[Mahogany]

Thanks Squirm & Natalie, I appreciated your replies & to try and answer your questions...

The purging of it right afterwards, was just a back-to-reality panic and fear of my wife finding out or suspecting. Plus, a kind of disgust at just how embarrassingly slutty I’d been.

Like part of the excitement was in being completely out there – at total odds with the regular me, or how my wife/friends perceive me – but it's also what can make it crazy, freaky frightening.

Like the same hard-on thrill thinking, “if she could see me now” is also the absolute last thing I’d want in reality. Which is why having any conversation about this with my wife would seem exceedingly impossible.

After I learned she’d cheated on me (at a wedding I wasn’t at), one of my first reactions (also unexpected) was to masturbate imagining my wife with the guy. Her friends also knew, I felt humiliated, and developed cuckold feelings (but didn’t want that reality either).

I’d never have imagined I would have ever given a BJ before this, but out of nowhere, developed a curiosity. I tried to mentally shoo it away to no avail. Eventually, I got a little obsessed, thinking I’d at least try it once, so why not act. I wasn’t really looking for gay guys, so much as a hetero guy, like the older man my wife was with, and when the WC guy talked about me showing photos, it became a hybrid-safe-semi-cuckold-type situation, where it was as much about my wife, as it was about me.

The idea of dressing like a woman never occurred to me until he brought it up and saying he wanted to bring out the female in me. I took it as an added level of submission & crazy surreal, and that’s what kind of drove my curiosity.

And dressing up to give him the second BJ, did add to the whole experience (more surreal, made me & him less inhibited) and is the BJ I recall when I masturbate.

But as for telling my wife, I just don't see how she could be remotely understanding. It would be one thing to tell her, I’ve had this long-held secret, I like women’s clothing, I feel more myself in female clothes, I feel trapped as a man etc.

She’d have to be understanding to that, in a Caitlyn Jenner kind of way.

But I have no real affinity for women’s clothes and completely identify as male.

So I feel like I’m in this freaky “other” category…not really a crossdresser at all…except when giving a BJ and showing off the wife.

Like there’s zero applaudable about my reasons for dressing up, and a lot for her to be disgusted by.

I could say, “none of this wouldn’t have happened had she not cheated” but that would sound incredibly weak and lame, I know.

And while she hasn’t cheated since as far as I know, I’ve had suspicions, particularly lately with her doing zoom calls to her friends (back where we grew up and where she hooked up at the wedding).

The past two months, my wife’s had me say hello to her friends on a number of calls - girls who were at the wedding & know my wife cuckolded me, was incredibly freaking awkward for me, but also had me hard afterwards.

I realize at some point I do have to have a real heart-to-heart with my wife and really find out where her head is at. She still talks about starting a family in a few years, like it’s still in our future. But if she does cheat again, I realize it’s a total wild card, and I certainly couldn’t say I wouldn’t do it again. And even now, if the WC guy said he was visiting, I’d probably start looking online.

But it’s been a while now, and there’d been a couple months where I wasn’t even thinking about it much. Like it can go in waves, and having to make small talk with her friends, just had me thinking more about it again.

I don’t think I could ever tell her about the WC guy, but at some point, I do agree, I have to figure out if my marriage truly has a long-term future.

 

[sissy.natalie]

Just my two cents, but the 'wife cheated' conversation and your crossdressing are somewhat decoupled, if you'll pardon the pun. It sounds like to me you are aroused by the submission/humiliation of both situations. The fact that your wife kinda rubbed your nose in it by having you say hello to all her pals is really making you wear the horns. That would humiliate me, and arouse me as well. Your crossdressing/seeing a guy (it was just one, right?) is a form of acting out in my opinion.

Deal with that, then move on to the other stuff. One war at a time, I think someone once said.

 

[SquirmingSub]

@Mahogany - Thank you for the update.

As mentioned by @sissy.natalie a conversation about the 'wife cheating' and you 'cross-dressing' would be two very separate issues and should be treated as such. I would also agree that your post would suggest that you are indeed aroused by the submission and associated erotic humiliation of each of the situations.

It would seem that your wife had no issues with being out in the open with her friends about her cheating on you. If you would like her to be a hotwife, for her to explore those freedoms, let me her know, talk to her about your respective desires and accept what she has to say without judgment. You might actually be surprised at the outcome. I have had a positive response in most of my relationships over the prior 30-years when it come to alternative lifestyle choices. The reality is, your wife cheated once, she will do it again, so you might as well have a truly open-minded honest and judgment free conversation with her. Enjoy the her being a hotwife together as a couple as opposed to being a cuckold with a cheating wife.

As to your one-time cross dressing with the one man; as @sissy.natalie suggested, maybe it was simply a form of acting out and you have since found it was not for you. If that was truly the case, put it behind you and move on. As far as being of service to another man without the cross-dressing, you may find that it will have been a positive experience in helping you ready yourself in the event you wife does open up and be a hotwife with your support.

 

[INBull]

The fact that your wife kinda rubbed your nose in it by having you say hello to all her pals is really making you wear the horns.

It might be wise to consider the possibility that this could have been an inept or negligent "error" on her part;

I'm an engineer, so causal analysis (ie. equipment, material, or design failures, or whatever) is something I'm always thinking about. I even apply it to people to find the "why" behind various relational "breakdowns" and I'd get tied up in knots pretty bad coming to conclusions like 'it had to be ___' or 'is she really fucking with me?' so on and so forth... And yet, whenever my last GF would get all tied up in knots doing the same thing and coming to WILDLY off-base attributions of why I did something that hurt her feelings or whatever, I was often using the 'well sh**, sorry honey--I really didn't mean to do that' response.... (which didnt really work very well)

So somewhere in the midst of my last LTR, it occurred to me that machines tend to be easy to troubleshoot because what they 'do' tends to be governed by physics more so than 'malicious intent' or 'if it feels like it'. People, on the other hand, do have malice and whimsy, but they also have these whole "negligence and/or ineptitude" aspects besides "intent" that can also drive negative outcomes that may be unintended. Yet I had (as had my last GF, I would contend) been totally ignoring these aspects when trying to gauge the intent behind something objectionable she may have done, And it should be easy to validate--just have to ask them (probably when they're NOT wound up over something) and then if they're authentic in their response, let it go.

Anyhow, it may hurt less if you also consider those other possibilities when people do fu**ed up shit.
(I wasn't there, so this concept may or may not apply there. YMMV)

Anyway, I hope this thought helps somebody, somewhere.. on something.