Small things that make you feel more like a sissy?

[cuteandfun99]

What are the small or subtle ways you feel like a sissy?  To me it's things like

- girly PJs (cute cotton types)

- early bedtimes

- my wife does all of the driving

- only buying from ladies clothing sections (even if more androgynous clothes)

[Rachael-Little]

Wearing a bra everyday and just a bit of makeup 

[jesse78]

Wearing panties, thigh high socks and of course any cute pink diapers

[Squishy69]

For me it’s just wearing a loaded pink diaper 

[SparklyPrincess]

I used to love wearing Fantasie 20 denier white hold-ups but they were so fine, they'd break or ladder after one night. I decided to cut off the lace top and pull it over my tights for extra girliness.  

[foreverdl]

I wear tights women's underwear and if I can get my wife to except maybe a skirt?? Maybe some day, I have teased her in a few stores when I have felt them and smiled at her,, she didn't respond wrong,,, there's hope yet, she has come a long way with my diapers she has even bought me some diaper stuff,, and carried things out of the store, and 10 yrs ago I wouldn't have even considered asking her... We have gotten used to a lot over the last 31 yrs ....I would Love to dress in completely girly cloths.....I got some silky woman's underwear today and silky gym type shorts, and she helped me pick them out...

[SparklyPrincess]

I've two straight good quality wigs, one blonde and one auburn. I brushed both of them, split them into bunches and tied them with pieces of white and pink satin ribbon into bows. Simple but very effective. 

[TammyG]

Given my difficulties fastening anything these days cute socks such as long ones with patterns and bows usually sold to lolita fashion followers but hey they work well for us too or those frilly top ankle socks.

The best thing is actually wearing them in a public setting like ordering coffee and a slice of cake.

[backdoorlarry]

I'm a sissy because: - I have a small penis - I wear a cage - I wear women's panties - I wear a bra - I wear garters and stockings - I wear sissy socks - I wear dresses - I wear pink diapers and rhumba pants - I dress like a sissy baby for bed - I perform oral on toys - I clean out behind and insert things that are shaped like a man - I dream about being taken by men - I want a mommy to breast feed me - I love shopping for panties, and so much more.

[Joanne_chan]

Good for you although it's not my thing. Just be your authentic self.

[foreverdl]

On 8/2/2026 at 8:09 PM, backdoorlarry said:

I'm a sissy because: - I have a small penis - I wear a cage - I wear women's panties - I wear a bra - I wear garters and stockings - I wear sissy socks - I wear dresses - I wear pink diapers and rhumba pants - I dress like a sissy baby for bed - I perform oral on toys - I clean out behind and insert things that are shaped like a man - I dream about being taken by men - I want a mommy to breast feed me - I love shopping for panties, and so much more.

You sound in ways like me, I can't wear the nice girly stuff that I want, being married for so many yrs I have been adding a item at a time, I now wear women's leggings in the evening I have silky underwear, I have had some yard sale one piece swim suits but they didn't fit, I keep teasing my wife when we are shopping as I handle the women's skirts?? and she just laughs so I may get there,, but I do enemas every night 4 qt warm water, and then play with a silicone dildo in both ends at the same time, and wishing I had it for real, but cheating is not right, so I haven't pursued it, my wife and I get along mostly real good I mean 30 plus yrs you get used to each other, and we both gave up on sex back in 2010 ish after we were both done with our cancer...so we have our toys and move on....

[backdoorlarry]

Sounds great. Glad you're both over the cancer thing. I hope she soon let's you dress around the house so you can be you. I'm a widower and my son and I live together. He works 40 per week so I have time to be me. I love wearing diapers at night and whenever I can during the day. I'm a sissy and love cross dressing. All kinds of toys are fun for me. Wife was mostly vanilla although a couple of times in 32 year she opened up a little. Here's a quick story about what happened one day.

.

For most of my life I've loved wearing women's panties and lingerie. I hid this from my wife for over 20 years when I finally got caught. I had some panties hidden under my briefs when she found them while putting laundry away. There was a big fight over it needless to say. Over the next 10 years she found my stash a few more times and the arguing seemed to lessen a bit.

One afternoon we were both feeling a bit frisky and I asked her if she wanted to go into the bedroom with me and masturbate each other. "Sure why not" she said, "I'll be there in a few minutes." I came back out a couple of minutes later wearing only a jock strap. I took her by the hand and led her into the bedroom. I closed the door as she undressed by the bed leaving only her red stretchy lace panties on. 

We slipped under the covers and began to cuddle while playing with ourselves and each other. Slipping out of my jock and slipping off her panties I thought I'd try something bold. I took her panties and put them on under the covers without her noticing followed by pulling my jock strap up on her. I took her hand and moved it down to her area to help her massage herself. She began breathing heavily and really started to like it. She lifted the covers to see herself and saw that I was wearing her panties. With her other hand she rubbed my bulge on the outside of her panties and got very excited.

I reached inside the cup of her jock as she reached inside my panties and we both began to vigorously masturbate each other. In a few short minutes she was climaxing and I was filling my panties. We lay back catching our breath and she rolled over to give me a kiss. "I'm ganna go have a cigarette and you can keep those on." To my surprise she was loosening up a little bit. She left the room wearing the jock and had it on for the rest of the day. I reached into my panties and made sure my emission covered me all over down there.

Going out to the living area in just her panties she got a look at me in them and said "Those look good on you, you can keep them." "Really?" I asked. She gave me a cute smile and said "Yes, and the others you have hidden in the closet."

.

Sure made me feel great that day.

[foreverdl]

17 hours ago, backdoorlarry said:

Sounds great. Glad you're both over the cancer thing. I hope she soon let's you dress around the house so you can be you. I'm a widower and my son and I live together. He works 40 per week so I have time to be me. I love wearing diapers at night and whenever I can during the day. I'm a sissy and love cross dressing. All kinds of toys are fun for me. Wife was mostly vanilla although a couple of times in 32 year she opened up a little. Here's a quick story about what happened one day.

.

For most of my life I've loved wearing women's panties and lingerie. I hid this from my wife for over 20 years when I finally got caught. I had some panties hidden under my briefs when she found them while putting laundry away. There was a big fight over it needless to say. Over the next 10 years she found my stash a few more times and the arguing seemed to lessen a bit.

One afternoon we were both feeling a bit frisky and I asked her if she wanted to go into the bedroom with me and masturbate each other. "Sure why not" she said, "I'll be there in a few minutes." I came back out a couple of minutes later wearing only a jock strap. I took her by the hand and led her into the bedroom. I closed the door as she undressed by the bed leaving only her red stretchy lace panties on. 

We slipped under the covers and began to cuddle while playing with ourselves and each other. Slipping out of my jock and slipping off her panties I thought I'd try something bold. I took her panties and put them on under the covers without her noticing followed by pulling my jock strap up on her. I took her hand and moved it down to her area to help her massage herself. She began breathing heavily and really started to like it. She lifted the covers to see herself and saw that I was wearing her panties. With her other hand she rubbed my bulge on the outside of her panties and got very excited.

I reached inside the cup of her jock as she reached inside my panties and we both began to vigorously masturbate each other. In a few short minutes she was climaxing and I was filling my panties. We lay back catching our breath and she rolled over to give me a kiss. "I'm ganna go have a cigarette and you can keep those on." To my surprise she was loosening up a little bit. She left the room wearing the jock and had it on for the rest of the day. I reached into my panties and made sure my emission covered me all over down there.

Going out to the living area in just her panties she got a look at me in them and said "Those look good on you, you can keep them." "Really?" I asked. She gave me a cute smile and said "Yes, and the others you have hidden in the closet."

.

Sure made me feel great that day.

My first wife passed away when my son was 6 yrs old, and I re married because it's the thing to do ? I guess, I do Love my wife, and she was very good with all my emotional issues I know many women would not have the patience for me having tears when things popped up like holiday or her birthday etc. So I do know the being widowed , I do hope you have someone to talk to if needed? and you can MM me as I have been disabled or over 10 yrs and have time to message, I have a couple guys here that we have talked for yrs.. about life and what we do that we don't want on the regular stuff..

[Sissypleasure]

Wearing pink

[sissytommie]

On 7/28/2026 at 8:13 PM, jesse78 said:

Wearing panties, thigh high socks and of course any cute pink diapers

You like really cute 

 

[Sasha_Nicole]

I love being in frilly panties 

[TammyG]

Oh frills, can we be without them? I don't think so!

[Mommy Wendy Marie]

Aside from having "sissy baby playtime" the thing that I find most reinforcing of my sissy self is laundering and hang-drying all my panties. I wear only the granny panty style and only in pastels, and once they're all up on the little white nursery hangers I use I stand back and look at the array and marvel at the colors, so sweet, so feminine and innocent.