Time for a fun post to cheer myself up. Going back and looking at the vast archive of pictures of Sarah/Julie I have on my ‘Sarah’ laptop there are certain looks I did that I love to go back and look at. And the reason I love to look at them is that they have a fun story behind them, created by the look and whatever was going through my head at the time.
See, I love the idea of role-playing. Of not only taking on the appearance of the woman, but also the mindset. It’s a chance to experience something from a perspective that I could never really have in real life. Some are stereotypes of women, some are creations from deep inside my imagination, but all of them are just a lot of fun to be.
So, as I’ve been feeling down for a while, I thought I’d dip into the archives and generate some double pictures of fun looks that jump out at me, along with what I see when I look at the pictures. It’s very cathartic and therapeutic, plus it makes me smile and, being honest, it gives me that fuzzy little tingle of fetish enjoyment.
Some have appeared before; that’s because I love the look so much. So bear with me; enjoy the pictures and, if it’s your kind of thing, enjoy the little histories of the characters.
And just to put it in context; I’m a 50+ year old man who is only just, in the last five years or so, exploring and discovering this side of me. I talk a lot about it in this blog but at its core it’s just the joy that these pictures give me. So please indulge my little bit of fun……
1: The Girl out of Time….
Yeah, I wear a lot of 1940s style dresses. There’s a reason for that; the style and femininity of these kind of dresses is, for me, almost perfection when it comes to being a period 1940s woman.
I did a couple of videos with this outfit as well, which are up on Instagram, and the combination of heels and frock just made it easy to become, momentarily, a 1940s girl.
I see her as one of those frustrated, stuck-in-England during the war girls that only has style as a way of showing her femininity. The Victory Roll hairstyle, the authentic shoes, jewellery and that pretty print dress are all things that she is very particular about.
I get the feeling that when the war finished she had a period of letting her hair down, relationship wise, before settling down finally to become the family woman.
If you are into the subject of this blog I highly recommend trying a tea dress, if only once. The way it hangs, the way it sways when you walk, it just feels so wonderful.
2: The Prairie School Teacher
I loved the feel of this dress; it’s a costume from a firm that does a lot of these kind of American styled historical costumes (I have a number I haven’t used in sessions yet which are adorably fun), and felt delightfully restrictive in that fun fetish-y way.
The roleplay idea behind this was the young schoolteacher, prim and proper during the day when teaching her students, and then, when they have all gone home to their farms, she can let her hair down. You can see from my smile in the second picture how much fun this outfit was.
I keep forgetting that you, dear reader, don’t know me in the ‘real world’. I’m grumpy, I wear t-shirts and jeans, I don’t care how I look, never brush my hair. Sarah/Julie is the absolute opposite, and this outfit and roleplay highlights that entirely. In fact it was hard to pose in the ‘tied back’ hair schoolteacher mode because I felt so severe, in a fun way.
The long skirt combined with the blouse (all one dress) was delightfully ‘covering’. It was easy to project the buttoned-down schoolteacher. And very hard to get the urge to take the outfit off.
3: The Happy Housewife
I’ve covered this look before but wow, I keep coming back to it. Partly because, especially in the second shot above, it looks absolutely nothing like me, and completely like a retro-obsessed woman working in her kitchen.
See, even typing that sentence gave me a thrill. I have absolutely no idea why I am so obsessed with the idea of the house-proud, fashion conscious woman who has decided to not have a career of her own, but instead commit herself to the family, the cooking, the cleaning, all of those tasks that don’t sit well with the post-modern feminist.
But it’s not a sexist thing. It’s a callback to the way women used to be, and the idea of changing from a privileged white male to a repressed 1950s housewife is delightfully BDSM. And the fashions of then, again, wow, they blow me away.
And the thing is, when I put on the dress, put on the apron and see myself in the mirror something clicks inside and become the wife. It’s just so much fun to adopt that role and you can see from the pictures how much it means to me.
It’s fantasy that can never really be. I know I’d be bored within a day with housework (even though I actually enjoy doing it at home). But still, the idea of surrendering to that role is one of those kinky little fantasies that really, really works for me.
I’m going to honest; this and other housewife looks are the ones I go back to when I want a thrill. If I won the lottery I’d buy Sarah a house, have it decorated 1950s style, and then go there whenever I wanted to let my hair down and be repressed for a while. Might even get brave enough to invite a like-minded admirer to be the waited-on husband. And yes, that’s a goto fantasy for me when I want to cheer myself up. The idea of having a man as a counterpoint to the prim and proper housewife is gloriously fun.
4: Her Special Day…..
I haven’t done a lot of wedding dress looks, partly because they don’t make those glorious 1980’s puffball sleeve OTT dresses that I really crave (again, if I win the lottery I’d hire a dressmaker and commission them to make all the dresses I craved while growing up in the 80s and hiding my urges), and partly because they always feel like crossing a certain line.
But when I have, wow, it’s been a lovely thrill. There’s a lot of hidden meanings behind the outfit; the pairing of a woman and a man, the acceptance of the concept of marriage (women still, in most cases, relinquish their own names in favour of their husband’s) the idea of, cough, the night of the wedding.
Plus it’s actually the woman’s day; a chance for her to look glorious (and hopefully put the bridesmaids to shame) and a moment when she is the absolute centre of attention.
Again, the one thing that would make this roleplay just perfect would be a willing husband to hang off of; that’s not going to happen for me because, being realistic, I’m about a foot taller than most admirers. Still, a girl can dream.
5: The Church Dress
Confession time, given the church nature of this dress; I bought this dress from Unique Vintage when I saw a customer picture on the website. The woman was wearing this dress, with a lovely white hat, whilst holding the hand of her young daughter who was wearing a white communion dress. The whole framing of the picture, the proud mother heading to church in a conservative yet stylish floral 1940’s style dress just clicked for me, so I had to have one.
It’s slightly too big for me; it was too big even when I had a little extra weight on me, but I love the style, the sleeves, the inner lining (you can’t see it but it is white satin and feels like you’ve been wrapped in a piece of heaven). I keep trying it with different hairstyles but haven’t completely nailed it yet.
So, on the roleplay side this one is easy. It feels so conservative that you can’t help but switch into a Christian lady mindset. Again, completely diametrically opposed to the drab me; in fact I’m pretty sure she would cross the road rather than walk past drab me, and that in itself is another of those wonderful thrills. She would completely look down her nose at me.
Fantasies wise I’d love to go out about in this outfit but I’d need to find the right time and place. It feels like a ‘village fete’ outfit and I’m not sure a glamorous retro Queen would be openly welcome to a wholesome church fete…..
6: The Middle Aged Trophy Wife
Pure wonderful roleplaying, this outfit. It’s one of those lovely dresses that older women tend to pick, along with a sensible ‘Jane Fonda’ style hairstyle. Stylish without being overtly sexual.
The mindset I use for these kind of looks is to imagine myself as a frustrated middle aged woman in a relationship with a husband who wants her to be on his arm, nodding at the right points, smiling on demand. Basically a fashion accessory for him. So she has a bit of frosty attitude, she flirts openly with the waiters and can be somewhat of a cold bitch, if you’ll pardon my language.
She knows she is getting older and her husband has eyes for the younger women, but she won’t stoop to his level and sticks to the sensible outfits.
It is way too easy to slip into that mindset which is eye-opening for a middle-aged hippy. Eye-opening and oddly exciting.
7: The Stereotypical Black Widow/Femme Fatale
Ever since I first saw ‘Rachel’ walk out of the shadows in Blade Runner in her tight 1940’s suit I have wanted to try the femme fatale look. A dear friend of mine bought me this dress, from Collectif, and when we tried it at the session it just felt like one that would make an adorable femme fatale look come to life.
So Cindy darkened the eyes, darkened the lipstick and we did this look. In terms of roleplay it was easy; I fired up my surprisingly good ‘resting bitch’ face (who would have thought I even had one of those) and just thought about how ineffectual the police were, how they’d never pin the death of my rich, older husband on me. Worked a treat.
8: The Shy, Ordinary wife
This dress sat in my cupboard for way too long. I bought it from Joanie Clothing in one of those post-midnight shopping sessions as an afterthought; I’d bought a couple of pretty ‘middle aged trophy wife’ dresses and saw it in the ‘you might also like’ pictures.
I didn’t think the colour would work, but during a session last year I was short of outfits and added it, not thinking it would be special but we could do it as a ‘warmup’ dress.
I was so wrong. We went for a mumsy style hairstyle and it all clicked. I looked like the shy housewife going out for the first time in a long time for a romantic meal with her husband. She is used to eating at home so putting on the glam and going out is somewhat of a treat, but makes her nervous.
She holds her handbag close like a life-preserver, a gentle half smile when her husband asks her if she’s OK. The restaurant owner walks her and her husband to their table, holding the chair so she can sit, and she orders a glass of red wine (she never drinks normally). Her husband gently holds her hand and she blushes slightly as she reads the menu, not knowing what the meals are but pretending she does.
And that’s the kind of lovely little story that jumps into my mind when I see these pictures.
9: The 1950s Housewife questioning her choices….
I fell in love with this dress when I saw it on the Unique Vintage website. They pitched it as a ‘I Love Lucy’ memorial frock but it’s wonderfully 1950s; the collar, the frilled shirt front, the cuffs, the flowing skirt with a petticoat. Add a red head look and some pearl jewellery and it was perfect.
We did a lot of pictures but I wanted some showing the angst of an unhappy housewife. She had thoughts of a career, maybe a nurse, but married early and, as was the fashion in the 1950s, it was expected she would start a family. Two children followed, who are now at the difficult early teenager period, and her husband spends way too much time at the office and drinking afterwards.
She’s convinced he’s having an affair and, even though it pains her, she makes a serious effort with her makeup and choices of dresses to appeal to his need for a ‘proper housewife’. She’s thought of leaving him but it’s the 1950’s in America and that’s just not done. So she is stuck and sometimes it shows on her made-up face.
10: The Lady Golfer
Amusingly this was inspired by playing a golf game on the PS4. Lately I’ve been picking a female avatar for everything (in the old days I used to just create an avatar that looked kinda like me in real life – I discovered it’s actually quite thrilling to create a female avatar and dress her appropriately) and some of the pink golf wear made me smile and wonder whether I could pull it off.
So I sourced a pink polo shirt, a pink tutu style golfing skirt, white lace socks and a pink sunshade hat and et voila, golf-girl was born.
Yes, the heels aren’t regulation, but I always go back to this look because, well, it’s so damn pink. It’s that hot pink you know some women go for because it’s quite attractive to the opposite sex, and it makes a statement about the femininity of the woman even when doing sport.
Not my usual look but exactly the kind of female golfer I’d love to have seen back when I played golf. But again, if I had seen one, I’d be fantasising about wearing her outfit as opposed to having a relationship with her.
11: The 1980s Mother
Every once in a while you find a dress that clicks for you, whereas other people go ‘what do you see in that?’. This dress does it for me. It’s a 1980s style fashion that a lot of the mums used to wear; it was a ‘Lady Diana’ style, the severe shirt style of the dress top countered by the lines of flowers, the collar done all the way up to maintain modesty.
Yeah, it’s hard to describe, but this frock always gives me a thrill. It ticks my love of the 80s look and it’s not a dress women would wear today, even though it is a modern design. I love it because it lets me channel my inner repressed 1980’s woman. The kind of woman who idolised Princess Di and went out of her way to dress in a similar way.
Plus, in an odd twist, I look exactly like my mother in these photos. I don’t talk to her any more, a long life of dealing with her issues left a scar. Being honest she kinda made me a crossdresser, so it feels like a little bit of justice to steal her identity. Sort that one, shrink…
12: As far from my drab self as it is possible to go….
Straying seriously into fetish territory here but when I did I thought ‘what the hell, let’s go for it’. So Cindy massively upped the makeup look, extreme lip size, lots of glitter and red eyeshadow.
The mindset was simple; if you’re going to do the sissy look you need to embrace the inner sissy. The costume was from Birchplace, a proper sissy maid uniform (with a great little starched petticoat), huge pink bow for her hair and, if you’ll pardon the pseudo pun, f*ck-me pink heels.
I’m not usually a submissive person (ignore the obsession with being a controlled housewife if you can) but the idea of just letting go was so much fun. It’s an OTT look but when I feel like some naughty fun I go to these photos.
And there you go, a quick fun interlude to cheer me up. And it has. I’m hopefully doing a session next week (I may need a lot of foundation on my chest as the waxing has really messed it up) and I’m in the mood for some more housewife looks…..
Stay beautiful and remember that your fantasies are your fantasies. As long as you don’t hurt anyone else, you can do and be whatever you want, and don’t feel guilty. Unless guilt is part of your fantasy, of course….
3 thoughts on “[Fashion] Dungeons and Dragqueens”
Superb photos of vintage fantasy.
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Sarah you are an absolutely amazing woman! 😍
I certainly understand where lots of your fantasies can come from sweetie. 😊 I used to enjoy playing a modern housewife back when I could dress for a day at a time. I’d do the hoovering and dusting and washing the pots, etc, in skirt, blouse heels and full make-up. It didn’t make the housework any less hard but it was certainly more fun and interesting! 😉
I’ve often wondered if these different looks we show of our feminine selves are reflections of the multiple aspects of our feminine personalities too? 🤔
I’m so pleased to hear that you are doing another session soon. 🙂 I hope that you have an absolutely wonderful time sweetie! 😘💋❤️
Take care of yourself my wonderful friend!
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I said I wasn’t going to spray comments, but this makes me a liar.
I love the histories that you have written, little vignettes and insights, and your evocative style does so much with few words. I was going to comment on a number of them and then I got to your 80s mother look and… I don’t have the words at all. But that one really spoke to me.
For context, I’m early 40s so don’t really remember all of the 80s and from the UK. But the north, proper north, so I guess women were a bit behind the times fashion-wise? – I saw this look well after its prime on most women I knew and looked up to (not my mother though). I think it’s the hair as much as the dress and the colours. Your facial expression seems to capture something of that period in the 80s as well. I can’t quite put my finger on it (maybe the belt? I don’t know) but it just… It spoke to me.
Anyway, that all these photos are of you; that you have them at all… All power to you.
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