Favorite types of sissy clothing

I have only worn a medium length pleated skirt, which my wife put on me...once. I loved it and would like to explore cross-dressing some more. But, my wife likes to see me as masculine, so she hasn't done it since

Today I'm wearing fishnet stockings, suspenders, frilly black thong and a pleated skirt. No heels yet unfortunately.

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I Like to be but on pink baby clothes

My everyday clothing is a dress with a petticoat underneath with 3" pumps. I wear this everyday over all my satin lingerie. When I'm out in public I wear skinny jeans with a printed cotton top and flats over my silky lingerie.

My favorite is g-string / c-string with strapless bras

I think of myself as a Sissy, but not a baby. I love to wear latex outfits; latex pantyhose or catsuits under other latex outfits or night wear. I also like to wear nylon pantyhose and slick and shiny nylon outfits. The best is a sheer nylon body stocking, like a catsuit. The nylons over my whole body feels sooo sexy sliding against a slick dress or nightie.

I also love it when my boyfriend wears nylon pantyhose when we have sex. Our hardons and legs feel so sexy rubbing together. I make a small hole in the front of his and a small hole in the rear of mine so we can keep our hose pulled up while he breeds my sissy hole.

Going out tonight wearing geometric mixed print maxi skirt, grey and white panties,whute bra and a white v neck top. For shoes i am wearing brown wedges.

I guess look at it from two different perspectives. One being dressed all sissy and slutty without much regard for pulling off a nice clean female look. I can dress as slutty as I like but still not look like a girl. Having a girl or two as a would guide me into more fem with the clothes and the makeup, then take me out to show me off. Sounds like it would be great fun.

Not sure if this counts but I really want a pair of cork soled wedges. I think my feet and toes look hot in my wife's, which are 2 sizes too small. I want my own pair in my size.

My favorite types of sissy dress are shiny silky golden or white tights and leggings, long white socks, high heels or white running shoes, and body swimming suit. It would be Naughty Lesbian role play in the Gym.

I forgot that I own 1 skirt. I have tried on most of my wife's and like some but I wanted my own so I bought one off Etsy, a tight, knee-high, made of hemp cute thing. For my age I still have very nice, but short, legs and I know I have nice feet but my wife thinks I might turn into the Danish Girl so I put it away. It makes me feel SEXY, I don't know why, but I know I look ridiculous.

My Mistress thought was a sissy should look like a male dressed as a sissy not look like a fem dressed as a sissy.

Ever since my surgery, I like nice, tight, pink "boy shorts", that leave no doubt that I'm not a male anymore.

My favorite is stockings and garters with panties over top. You girls knew why panties over top?❤️❤️❤️❤️???

I like to wear lace top stockings and suspenders and frilly knickers/ panties , I love the pull of the suspenders on the stocking tops as I walk to work ,with them on under my work clothes, I love to wear pink sissy clothes if and when possible .

I like to wear my wife's panties and bras. I like to be feminine for a man who likes to give me anal sex.

I love lace panties and thongs. They make me feel naughty and submissive.

It depends...i have my pink sissy frock that i wear with white stockings with pink bows on them. I also have my sissy heels--pink and blue. I also have plenty of the usual women's clothes--suspenders, stockings, panties etc.... The difference for me and my Mistress is that i am a 180cm tall 53 year old male and the sissy look is an over-the-top look that accentuates the fact that i am not a woman. i am not a cross-dresser nor a transvestite. These are very real distinctions i think. In a sense, there is a theatrical aspect to what i wear and why. i play a role, so does she.

I have always admired my aunt's nylon full brief panties. They were white, pink, pale blue, pale yellow. As a young boy of ten they were the first panties I wore. I was always afraid of getting caught so I did not wear them for long...but even in hat short time, I felt a certain special feeling, I think between feeling a bit scared, and feeling a bit like a girl. I did experience a pre-cum leaking, and looking down, saw a damp spot forming on the front of my panties. I was too young to know how to get rid of the spot, so just put them back as is. I don't know if my aunt ever know, but either my imagination or something else, when ever I saw her, she seemed to give me an understanding smile, which always made me feel uneasy....like , did she know (?) From that time on, I was always feeling like I was a sissy....but loving every minute of it .

My favorite sissy clothes would be white nylon full brief panties, more snug then loose fitting, more to remind me that I am a sissy, garter belt, and stockings, a bra and half slip. I'd be completely happy to be able to sit and watch TV....perhaps with a close friend.

I would love to be an eleven year old boy, in my aunt's bedroom, a warm breezy day, lace curtains blowing gentle in the breeze...the scent of her perfume and bath powder, lingers in the air. I have the house to myself and have slipped on a pair of her pink nylon panties. They are snug fitting and I can clearly see the outline of my erect penis pushing my panties outward. I feel clean and fresh, for just taking a warm bath. I have lightly dusted myself with her scented bath powder. Standing before her vanity mirror, I cannot help allowing my hand to drift down and gentle touch my pantie covered penis. I know if I don't stop, I will surely ejaculate, then what will I do, Auntie will surely find out. My hands travel to my bottom, the smooth feeling of nylon covering my bottom, my hand travels to the crack pushing inward, then across the silky cheeks....Ohhhhhh, I just can't stop, my hand once again to my pantie covered penis...rubbing slowly, then faster....breath coming faster, Ohhhhh, I'm going to, I can't stop.....Ohhhhhhhhhh, Ohhhhhhhh, feels so good!!! "A warm Spring Day"

Good lord, the options. I can give many scenarios of what I'd like done to me via dressing or forced dressing in sissy-ish clothing. Favorite types...

Well I personally love my diapers and I love the idea of feminization by a female but in truth I've never had it done to me yet. The types of clothing I prefer from online role playing so far would have to be any dress or skirt that gives subtle hints to full on exposure of my padded bum. I have a huge fascination for maid outfits seeing or wearing. I have far to many fantasies involving that combo. I enjoy my ruffles and frills like some do but I prefer they aren't an over kill of frill or ruffle. I mean I can see the appeal but really, it's not like we're blind to how much of a sissy you are with or without the frills. I've thought about my cross dressing/sissy fantasies to many times to count. If I was given the option to pursue any of my many fantasies I'd need more information as to what can and will happen by those or whom ever it is that wants to full fill this fantasy. I don't think I'll ever wear panties as I don't enjoy them in the sexual way that most seem to. That being said panties over my diaper I can do. Sure I won't wear them without a diaper on first but that doesn't make it any less humiliating! I mean seriously if you're wearing a diaper with women's panties on over that is quite the scene. Throw in being seen by someone else and there is vary little chance that person will see you as a man for much longer! So back to the types of clothing, I'll wear petticoats, pinafores, body shaping wear, bras and all those other underthings women wear. I like pantyhose, stockings, thigh high socks, tights, and pretty much anything that hugs my legs like those do. Something about a diaper stockings and suspender/garter belt under a maid's uniform that turns me on like there is no tomorrow. As for dresses I'll wear anything that is comfortable and is soft. I love satin, nylon, spandex and silks. Picking up on the tight and comfortable theme yet?

I prefer dresses that can be worn for lounging and ones that can be worn to parties or special events. Though I'm not sure I'd want to go to one that isn't private. Put me in a soft flowing skirt leggings and a cute blouse any day. Well now that I think about it I might wear women's panties but they'd have to hold and hug me just right. I won't wear skimpy undies for any reason unless they are over my diaper then it's just another means to embarrass me. Oh but ruffle panties and other such panties that cover my diapers are a must! I just love those to death! Oh come on who doesn't like a ruffle butt? For me though that butt has to be diapered first but to each their own. I love cute diaper covers that are pink or pastel colors anything that makes you think that person has a feminine side. For example; hearts, rainbows, unicorns, girly shows or movie characters on your plastic panties! Don't even get me started on the baby clothing... or do! My ideal outfit would be a nice thick disposable or cloth (doesn't matter), plastic pants (clear, transparent, print design of some type), cute matching tights over my bulky bottom, ruffle panties(optional) and finally my cute baby dress which either shows off my cute bum or just barely hints at it! There are way to many ways to dress this diaper butt and some of them I enjoy more then others! In my mind when it comes to being a sissy it;s to be more of a baby girl then an adult woman. Sure there are clothes for it but I see myself as a baby sissy then an adult one if I have to pick. Now am I leaving anything out? Oh yes sissy baby girl clothing isn't just dresses there are rompers, skirt-alls, onesies, footed sleepers, and many other sorts of sleep wear. I'd even wear some baby-dolls and teddies to as long as I'm diapered under them. Huh, I guess I do have a strong fascination with lingerie and diapers in a sissy and non-sissy sort of context. Well I think that about does it for me as I can't think of other types of sissy clothing I'm comfortable with.

I hope you all enjoy the read! I didn't mean for it to be that much!

I adore pink frilly rhumba panties and my frilly ankle socks,anything ultra frilly and girlie

I am a bisexual who loves wearing women’s leather clothing and women’s boots.

I love angora sweaters and dresses. They are so warf, soft ,cuddly and nice 😃

I just love to wear them. Makes me feel so feminine.

Off course, fluffy mohair sweaters are ice too.

I love to wear nylon full cut briefs. Thoes are what I use to take out of the dirty cloths hamper and try on, my Moms . I have worn lots of bikinis, but love the briefs.. i hate thongs.

My favorite is stockings thigh hi give me a special feel,,I also love Garter belts hi waist girdles and the feeling of my bra ,,,I have been wearing my breast forms most of the day now ,,,the weight of my full DD in my bra is very special,,,,walking around the have a bouncy feeling which is wonderful

I'm inexperienced in wearing sissy clothes; but, I have started to wear panties. To date I have purchased 1 pair in a boy short style, 2 pair of hipster style panties and 4 pair of thongs. My take so far is the front material on the thongs isn't really enough to contain my cock and balls completely and all day. I may start out with them contained; but, they like to sneak out the sides. The hipsters work really nice. The boy shorts were the 1st panties I purchased and they are 1 size to large. They hold everything in; but, they don't like to stay up in back. However, I wear them all under my diapers so none of this is really a problem. I think I enjoy the thong panties most as I am 1,000% anally fixated and I like having the crack of my ass and my hole constantly being reminded something is trying to excite them.

Today was the first day I looked for something else. I was at CVS and Walgreen's. While in both stores I looked for thigh high stockings with lace tops. The only size in both stores was S/M which would not fit. I would need a L/XL for certain. I look forward to getting a pair or 2 of these and think I will enjoy wearing them and panties around the house when my wife isn't home. She would faint.

Well so far all i have worn and experimented with is panties and I love stocking

I really like stockings and panties. You can see on my albums.