When did you first start participating in sissy activities.

Rahrah1

I’m a sissy boy who loves to use her diapers
Est. Contributor
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100
Age
24
Role
  1. Adult Baby
  2. Diaper Lover
  3. Sissy
I first stated in the 7th grade. I would sneak some of my mother’s bras and panties out of her room and wear them and play around. That lasted a couple months till I forgot to take them off before I fell a sleep and my dad woke me up and started yelling at me. After my parents split though I started doing it again when I would go stay at my moms house.
 
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I used to wear my mothers panties when I was home alone.
 
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Seasonedcitizen said:
I used to wear my mothers panties when I was home alone.
The felt so good and comfortable and I did look super cute and girly
 
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I first put on panties in my early teens (I think, not sure of the exact date, it was a long time ago). I had a sister but she was 5 years younger than me so I used my mother's.

Eventually I dressed fully: panties, bra, girdle, slip and dress.

I didn't do this too often as I didn't really feel a compulsion to do it too often. I then stopped while in the Army and started again after I got out.
 
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BabyDenise said:
I first put on panties in my early teens (I think, not sure of the exact date, it was a long time ago). I had a sister but she was 5 years younger than me so I used my mother's.

Eventually I dressed fully: panties, bra, girdle, slip and dress.

I didn't do this too often as I didn't really feel a compulsion to do it too often. I then stopped while in the Army and started again after I got out.
I’m probably gonna do it more often when I get my own place or get out of the service
 
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These days, I suppose I'd call myself a "diaper sissy," in that my diaper preferences are girly when possible and neutral otherwise. That started when I was 12 or 13 years old and finally got up the courage to hike to the store with my allowance and buy Pampers. For years, I'd been playing with the old cloth baby diapers that were still around the house, but the disposable diaper ads on TV were too much. I had to get some. This was 1989 or 1990, and baby diapers came in girl and boy versions. I bought the girl ones, initially because I wanted to make it clear to the store employees that I wasn't buying them for myself. Talk about goofy! :rolleyes: But, I was a kid, and those kinds of countermeasures seemed important.

It turned out, though, that wearing the girl diapers made me feel especially naughty and little, so I kept buying them--and, fortunately, was never caught! (Unfortunately, the gender-specific Pampers and Huggies were only around for a few years. 😢)

Later, in my mid-teens, I went through a phase similar to what others have described: I borrowed bras and panties and other articles of female clothing from both my mom and my sister, and played with dressing as a girl. It never left my bedroom, but it went on for several years and was almost as captivating as the diaper thing. It wasn't until my late teens that, very suddenly, my interest in wearing girls' things disappeared, and was replaced with an interest in see girls' things on girls. :) By that time, there were no girl/boy diapers, so my sissy was fully backburnered.

(I could relate some humorous anecdotes about digging around for things that would be good to stuff bras with. Tissue paper was never satisfying. But, I digress.)

Over the last eight years, since joining ADISC, I've gotten back into wearing cloth diapers, and though most of these are prefolds and thus gender-neutral, I've indulged my trace remaining sissy-ness with some cloth training pants in girly prints, and (recently) some My Little Pony cloth diapers and diaper covers. Love 'em. (I don't count myself a "brony," by the way. I just find the MLP stuff cute. {{blush}})
 
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I would say I started participating in sissy activities back in my early 20's. When my mom was helping me create Link's tunic from the Legend of Zelda. I first put on a green women's dress from Goodwill that we purchased and I got the awkward "why boner". I think that's what really kicked the feeling off for me. Than after that I discovered my love for Girl's underwear and switched from boxers to panties (going on 2 years since my switch). I've been happy ever since.
 
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Halloween is a great time to dress up and go out. I used to dress as a witch and do my errands for the day. I would kid women that I had better legs and raise my dress just enough to show the bottom of the pink ruffled panties.
 
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I am 'π' boy, born 3-14. I was born with a full head of hair and on 3/17,* the nurses brought me to my mother with a green ribbon in my hair.

*in those days new mothers stayed in the hospital a week or more.

My hair grew and my mother was often told what a pretty girl I was.
When I was 2 my mother had my long curly hair off. Obviously I don't remember the specifics but I was present and heard them.

When I was 6 we spent we spent a summer at my grandparents cottage in upstate NY. My grandmother had a closet full of clothes I was encountered to dress up in. I still remember the feeling of putting on her slip. It was cool and silky smooth and made me feel a kind of excitement. I also remember coming downstairs wearing one of her dresses and everyone clapping and telling me how cute I was.

About the same age give or take s toy maker was advertising a doll & bath set. You could bathe you babydoll in a toy tub with water. I was fascinated by the bathtub with water and wanted one for Christmas. I was discouraged from wanting it and despite continuing to ask for it, come Christmas, instead of the doll and tub I got an Erector Set, funny, ironic and sad all at the same time. Did that disappointment factor into my latent feelings? I don't know, but that was 55 years ago and that was the only present I remember not getting, and the only gift replacement I ever got that I remember. I don't think I wanted the doll because I was 'a girl', the year before, or after I wanted a garbage truck and didn't want another doll, or to wear a bra or panties, or a diaper until much much later.

In high school I found a young girl's bikini top and I pinned it to a T-shirt and would hold it up in front of my reflection and say that I was s pretty little girl.

During college I found a frilly, nightie in the mobile home I lived in and used to wear it sometimes.

Decades have passed and I occasionally toyed with adult diapers, baby play and bra and panty wearing but it was always for a short period and limited in scope. It is only recently that the two have intersected, escalated and feel natural as opposed to naughty.

Once again, I have never shared any of this before this post.
 
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Only recently have i started exploring my girl side. And only as a diapered girl.... not interested in big or adult lady clothing..... started innocently enough. Unisex style clothing like onesies and footed pjs...first pink ones. Then girl theamed cartoon prints..... then i got a pair of vinal pants with laces around the legs and waist...... just recently i pickup up my first baby doll dress.
 
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Is it pink and frilly?
 
I remember asking my nanny when I was 7 years old to treat me like a baby again. She didn't hesitate at all and the next day when I was being picked up from school she had a purple over shield car seat for me to sit in. But what I didn't know, was she'd put me into a sissy dress, w/ girly diapers. I didn't really approve of the sissy stuff.
 
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TexasToast11 said:
I remember asking my nanny when I was 7 years old to treat me like a baby again. She didn't hesitate at all and the next day when I was being picked up from school she had a purple over shield car seat for me to sit in. But what I didn't know, was she'd put me into a sissy dress, w/ girly diapers. I didn't really approve of the sissy stuff.
I wish I was in that situation
 
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was 3rd or 4th grade wearing 1 piece swimsuits
 
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TexasToast11 said:
I remember asking my nanny when I was 7 years old to treat me like a baby again. She didn't hesitate at all and the next day when I was being picked up from school she had a purple over shield car seat for me to sit in. But what I didn't know, was she'd put me into a sissy dress, w/ girly diapers. I didn't really approve of the sissy stuff.
Was your nanny your babysitter or your grandmother because I know some people called their grandmother nanny
 
CutePrincess said:
was 3rd or 4th grade wearing 1 piece swimsuits
Did you’re parents ever find out
 
Rahrah1 said:
Did you’re parents ever find out
i got no clue, lol, my mom found out on something related to this area later but not the bathingsuits specifically. I would also tried on my cousins ones on too. (more then one) to my knowledge no one found out, and I do not see how.
 
CutePrincess said:
i got no clue, lol, my mom found out on something related to this area later but not the bathingsuits specifically. I would also tried on my cousins ones on too. (more then one) to my knowledge no one found out, and I do not see how.
I recently told my mom about it because I was dealing with stuff she didn’t seem to upset about it
 
Rahrah1 said:
Was your nanny your babysitter or your grandmother because I know some people called their grandmother nanny

No. Dani was a live in Nanny and she now works for me. She is my Housekeeper / Nanny.
 
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TexasToast11 said:
No. Dani was a live in Nanny and she now works for me. She is my Housekeeper / Nanny.
Does she know you still wear diapers
 
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