Post-Halloween Recap

[sweetdreams]

Hi all.

I haven't posted anything since about a year ago, mainly because with Covid very little is happening.

In my past posts there have been details of my various outings. I fully dress and go out in public for various functions. I present a reasonable female persona, not great but OK (passable most times - walked through crowded malls without anyone clocking me, no strange looks). I've posted these in the past. I do my own makeup (lessons from makeup artists), have a modest but complete wardrobe, wife knows and tries to participate when the right opportunities arrive - Halloween is one such event.

Plans were made a few weeks ago. Checked out the local bar scene to see if there was anything interesting going on (Covid). There was. At this one Blues club called Blues on Whyte, they were having a Halloween show of dueling pianos followed by a pretty good blues band. Checked it out with the wife and booked the tickets.

This isn't my first rodeo so there wasn't too much to plan. We had done previous Halloween parties and our costumes were the same. She goes as a witch (somewhat sexy one) and I'm dressed as (yep you know) a girl. No prep work, just waited for the day to arrive.

One of the rules for the wife is I can't be made up too good. It has to be obvious I'm I guy in drag trying to look pretty. That said I have a wig that isn't my favorite that makes it pretty obvious what I am. I wear a dress with short sleeves (I don't shave my arms). The jewelry is big and clunky, almost comical. Big bow in my hair. Other than these obvious give aways I go all in. Some favorite boots with 3 inch heels, stockings, garter belt, bra, full makeup, etc.

Past years things have been fun. I take no prisoners. I'm out, I'm proud, the world has to deal with me and it does. As in previous years we go through the evening as if we are just in costume. I get cute looks from some girls, big smiles from others. The occasional two thumbs up from a few guys (probably closet CDs - who knows). Overall never been a problem. I go where I need to go (men's' bathroom of course), chatted with a few people sitting close to us. Mingling was minimized due to Covid, but still a good time. Really not a negative response from anyone.

Wife was a little cold initially (it's been a year since the last time), so it felt a little strange to her again. This changed over the evening. Conversation opened up, she started to relate to me a lot better, it got to be quite normal. She started to realize no one really cared. They think I'm a guy in a Halloween costume. All is OK. No hassles from anyone. Smiles from people in the street. Never was concerned about anything. Overall a great evening. Wouldn't miss it for the world. Can hardly wait for next year.

[susanmichelle]

Great post and it?s great that your wife allows you to dress and participate?s. Also glad you all had fun at least. I wasn?t able to dress this year I?m in the process of moving not my idea my slumlord my water and hot water heater went out due to the sump pump going out and flooding the basement. He blamed me and tried to evict me but can?t due to covid19. Anyway I?m almost out and next year will make up for everything that?s happened. Sorry didn?t mean to go on about my events, just glad you were able to fulfill your Halloween night.

[Krisi]

You make the point I often make about crossdressers dressed as a woman on Halloween; You can't do a really good job or people will assume that this isn't a once a year thing.

I would love to go out in public with my wife, dressed as Krisi, but I would have to give it the full effort to enjoy it. I would have to try my best to present as an actual female.

I'm glad you had a good time.

[sweetdreams]

If you've ever been tempted to go out dressed up, Halloween is the best time to do it. If people clock you it's just not a big deal, in fact getting clocked as a guy in drag is part of the game so there just isn't a downside.

The first time I went out the front door was to a makeover and then on the way home I thought I looked so good I headed to the mall. That was nerve racking. Getting clocked in a mall is a little more upsetting. It did happen with a couple of people giving me odd looks, but overall everything was fine. I mingled with the masses and no one really noticed or cared.

For me Halloween is a no-brainer. I've done this for about four years now. Never a bad experience. Lot's of interaction with girls thinking I'm cute and novel. Just do it. Get out there, own it, relax and enjoy. So much fun.

Past years we usually went out for dinner at a restaurant and then to a bar. Again I never worried about where we went. It's obvious we are both dressed up in costume for Halloween. I get a kick out of the interaction with the waitress. Very often they have a great big grin on their faces, they blush, and say something like "what can I get you girls this evening". Ha!

As far as how far to go, it depends on your ability and experience. I'm pretty good at passing as a female so I dummy it down a bit to ensure I can be clocked fairly easily. If you don't have the experience you can go all out and it will allow you to hone your skills a bit. Practice, practice, practice. Remember to have fun with this.

[cindylouho]

Like most closeted CDs, it was always a fantasy in my earlier years, but ultimately I have never done it before, you've got my wheels turning Sweetdreams. Unfortunately its a year away...

[docrobbysherry]

I'm glad u enjoyed your outing, SDreams. But, I realized 20 years ago that only guys dress up sloppily as partial women on Halloween. I have no desire to present as a sloppy, half way woman, period!

Women and trans dress up as women in costumes on Halloween. And, we can do it to the 9's. Because Halloween is the only time some of us can actually pass!

It's a shame many of us, like u, live under conditions that will never allow u to experience what that feels like!

[sweetdreams]

I'm glad u enjoyed your outing, SDreams. But, I realized 20 years ago that only guys dress up sloppily as partial women on Halloween. I have no desire to present as a sloppy, half way woman, period!

Women and trans dress up as women in costumes on Halloween. And, we can do it to the 9's. Because Halloween is the only time some of us can actually pass!

It's a shame many of us, like u, live under conditions that will never allow u to experience what that feels like!

Sorry doc couldn't disagree with you more. You truly don't understand my situation. I do the full pull-out-all-the-stops dressup. I've walked the malls several times as a girl and not been clocked. I go out at times other than Halloween when I do go all out. I've had full makeovers by the pros where they've done convincing jobs of making me pretty. I've taken this look out in public and for the most part passed. I know perfectly well what it feels like to do the full glam look and own it.

At Halloween it just seems to be a little more easy and fun loving. You can let your hair down a bit (pardon the pun) and not be quite so worried about it. Especially if you haven't gone out before or haven't mastered your look. It's also fine to pull out all the stops. Personally at Halloween I get a kick out of the waitresses and GGs when they realize I'm a guy in a dress. It's not that I look like a $25 hooker. It's nothing crude. Still trying to look pretty, or maybe the best term is cute. I still look fairly convincing (and many don't even notice) but there are enough tells (more than normal) where they can clock me if they look closely enough. I enjoy the smiles, and blushes, and the attention I get from the GGs. They usually get a kick out of it. Too much fun. Talking with them is even better like complimenting a waitress on her Halloween costume (they usually will have one). The waitress will often compliment you on your costume. You can have a nice chat on a girly level with them, GGs like being complimented on their outfits - even Halloween costumes. Good conversation starter. I really enjoy the interaction.

Bottom line is we all need to do our own thing based on our personal situations. Main point I'm trying to make is Halloween is a time when acceptable behavior is much broader. If someone hasn't been out before and is nervous, you can get away with a lot more at Halloween. Just have some fun and enjoy it.

[bridget thronton]

Great Halloween post

[Taylor186]

. . . you've got my wheels turning Sweetdreams. Unfortunately its a year away...

Start planning now! Halloween 2021 will be here before you know it. (Spoken from experience. I've been out each Halloween for 15+ years, except this year.)

I get many of the same reactions SD does though, as Sherry suggests, I always wear a costume a woman might wear. I just feel more comfortable doing it that way. And no purposeful half way measures for me, I go all out, 100%. I have been mistaken for a woman at night on the street walking to a club or in the club, from 30 feet away. At 6' and 190 lbs plus 4" heels, that mistake never happens up close.

[Stephanie47]

Thanks for sharing about your Halloween adventure. My wife and I are in a deep "Don't Ask, Don't Tell" marriage. The last time we had a conversation, "The Talk," was about 1983. If you and your wife are going to go out together to a venue I would suggest asking her whether you could try to do your best to totally look like a woman. That's especially true if you're going to a venue where the chances of an encounter with someone who knows you or your wife is minimal or non-existent. Your wife could take the credit for making you up to the woman you envision; no hairy arms or unshaven face, great makeup and nice wig. The giveaway is probably a man being able to walk womanly in a pair of high heels. When I have gone out on Halloween which unfortunately was too long ago I did everything possible to emulate a woman. I solve the high heel giveaway with a nice pair of wedges with a two inch rise. No issues with stability. If I was able to have gone out with my wife on Halloween I always envisioned the outing with the exact outfit down to the nail polish and wig; sort of the "Double Mint Twins" of years ago.

I understand your wife's point, but maybe she would be agreeable to being a little more adventurous. Anyway, thanks for sharing.

[sweetdreams]

Hi Steph.

I actually have a couple of looks that I can use as needed. Makeup is ALWAYS well done (well shaven of course - its a good look). Clothes are a little different depending on the look I'm after, but always tasteful and feminine (girly). ALWAYS nice shoes (feminine with three inch heels - I do OK with these). Wigs will vary, but these are high quality wigs and both a pretty good look for me/my face, one a little better than the other but both very girly and suitable.

I do have an all-out full-glam look (refer to my other posts) where I'm aiming to blend in and not be noticed (in other words pass). I've taken this look to the mall several times as well as other venues. Wife knows about it and has seen it. When I'm on my game everything is good, no intentional give-aways. Long sleeve blouses to hide the hairy arms. Makeup is well done. Wig is in place, properly brushed, and compliments (frames) my face well. It's a pretty good look that I'm proud of and it took a concerted effort to achieve. Several visits to makeup artists to learn how to do that. For the wig I went to a local wig shop and tried on at least a dozen styles and lengths to get a sense of what worked for me. For the wigs I took tons of pictures and even posted about a half a dozen on this site for opinions. A cute little Bob style is what works the best. I very often pass without notice (i.e. my mall walks - zero odd looks). I'm just a few feet away in the middle of a crowded mall and watching peoples eyes and don't see any stares/odd looks of any kind. I do go out, own it, and carry it off pretty well in this mode.

Halloween is different and I actually like dummying it up a little. Not much but a little. Other than a few tells I'm still full-on. Actually it's fun cause I still try to look pretty (lets say cute). I am still very girly. I have my longer length wig (shoulder length - my second favorite). I find it quite a hoot to get clocked by GGs and see their reactions when they do realize I'm a guy. I get to be girly, cute and interact with them. Typical reaction - big smile, blush, and then we chat. Always enjoyed the interaction. When out for Halloween, I actually encourage the clocking/interaction aspect. I'm still full-on makeup, clothes (other than short sleeves), boots (really cute pink ones - 3 inch heels), underwear, etc. A lot of times when I walk to the bathroom I don't think a lot of people even notice what I am. Every once in a while a couple of GGs pick up on it and that's when they beam. That's when the fun starts - yep you caught me, I'm a guy in drag looking really girly and fairly pretty and you caught me, what do you think? Usually compliments and suggestions (try this, try that, I really like this or that). Too much fun, and girls just want to have fun right?

[SIZE=1]- - - Updated - - -[/SIZE]

Thought I would add a couple of pictures to show my two looks with my wigs. The top one (shoulder length) is my Halloween wig. The Bob is my favorite:


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