How did the 'Sissy' experience develop for you?

Have you ever forgot you were wearing it or forget to wipe it off and go somewhere where you shouldn't. I once forgot to take off my earrings one time.
Well my wife keeps me right but yes almost clocked in at work with lipstick on lol . Have actually worn very subtle eyeshadow all day at work - not sure whether you could see it or not - important thing was I knew I had it on and the women were the real threat - I was certain one would notice but no or at least never said , I used to take a pic on my phone with eyes closed to make sure you couldn’t easily see it , one guy mentioned that I had glitter on my cheek but I laughed it off as something to do with my wife - that was close call too - thrilling but dangerous
 
Well my wife keeps me right but yes almost clocked in at work with lipstick on lol . Have actually worn very subtle eyeshadow all day at work - not sure whether you could see it or not - important thing was I knew I had it on and the women were the real threat - I was certain one would notice but no or at least never said , I used to take a pic on my phone with eyes closed to make sure you couldn’t easily see it , one guy mentioned that I had glitter on my cheek but I laughed it off as something to do with my wife - that was close call too - thrilling but dangerous
Some of that eye shadow is hard to get off. I found that very light residues seemed to enhance my appearance as a guy. Kind of making me closer to a "pretty boy". One time I got carded and I was well over 40. And yes women will pick up on everything, kids too. They are so tuned in. If you don't get all the lipstick off at least you can say it rubbed off kissing your wife but eyeshadow and mascara are a different story.
 
Some of that eye shadow is hard to get off. I found that very light residues seemed to enhance my appearance as a guy. Kind of making me closer to a "pretty boy". One time I got carded and I was well over 40. And yes women will pick up on everything, kids too. They are so tuned in. If you don't get all the lipstick off at least you can say it rubbed off kissing your wife but eyeshadow and mascara are a different story.
Yes for sure , me and my wife used to dress fully and go for a drive at nighttime - that was amazing to be outside fully dressed and driving in heels was ok too lol . Then for some reason possibly the car being recognised by someone we knew or whatever she went off the idea . I just wish I had started many many years ago sometimes .
 
It was gradual. We met an ex-college black football player who made suck his cock in front of my wife. That changed her attitude towards me. She enjoyed the idea of me submissive to a man with a much larger cock. While we were spending the winter in Florida, she had a black personal trainer. He was dominant over both of us. He introduced to a friend of his that had a 10inch long and 6 1/2 around cock. He insisted that I wear a chastity cage and panties in his presence. I had to fluff and clean him whenever he wanted.DVR___2026-12-01_22.52.34_Moment (3).jpg
 
It was gradual. We met an ex-college black football player who made suck his cock in front of my wife. That changed her attitude towards me. She enjoyed the idea of me submissive to a man with a much larger cock. While we were spending the winter in Florida, she had a black personal trainer. He was dominant over both of us. He introduced to a friend of his that had a 10inch long and 6 1/2 around cock. He insisted that I wear a chastity cage and panties in his presence. I had to fluff and clean him whenever he wanted.View attachment 1907601
That doesn't sound gradual to me. It sounds like it happened pretty fast. You seemed to be quite eager like as if the sissy in you was just dying to break out. How did it make you feel to suck cock in front of your wife?
 
We sometimes tend

We sometimes mince words. I'm considered a sissy but I'm not gay, yet if I'm ordered to give my wifes lover a blowjob I will. I do it not because I have a genuine attraction to men, I don't have that particular drive. I do it to show my obedience to my wife and to demonstrate my lack of manhood. Thats different than being gay. To me, being a sissy means surrendering all my manhood,(if I ever had any) and being totally obedient to my wife and submissive to her lovers. I will take him in my ass because I'm too weak and submissive to stop him. She enjoys seeing my weak effeminate nature and comparing this to her lovers desireable manly traits. She enjoys her experiences with him more this way. My humiliation is her aphrodisiac. Some uses of the word sissy might refer to homosexuality but again my brand of it refers to femininity, obedience and lack of manliness( a small ineffectual penis).
I don't have your experience,sadly. When I was younger I was too shy to admit my deepest desires. I relate to your feelings about sex with males. I don't like males and have rarelybeen attracted to them. Only feminine males/transgenders. I do want a woman who would let me worship her by doing things with men she supervises. I've sucked she males cock, but never til they came. I've only tasted my cum, and other mens cum when I ate a woman's pussy, which I love eating cream pies.
 
I don't have your experience,sadly. When I was younger I was too shy to admit my deepest desires. I relate to your feelings about sex with males. I don't like males and have rarelybeen attracted to them. Only feminine males/transgenders. I do want a woman who would let me worship her by doing things with men she supervises. I've sucked she males cock, but never til they came. I've only tasted my cum, and other mens cum when I ate a woman's pussy, which I love eating cream pies.
Me too. My wife tells me eating her cream pie is one of my sissy duties.