When did you first realize that you were a sissy?

Playing with panties and bras,always got me turned on. Later i realised i wanted to a women so i tried on my mothers clothes as well. I liked being all dressed up. It then progressed to using her make up. And so Natalie was born. My sissie name. This was when i was about thirteen. Every body knows i like to dress up.

I've always liked sissy boys that were very pretty. One of my bf's was well known in circuits as a cross-dresser. I have sissy tendencies, but was raised in a very conservative area. I think if young today, I would be much more of a sissy. When young, I use to get into my sister's Tampex and use them instead of underwear.

I often wish there was no differentiation in sexes, in that it was not such a big deal to most. I think I'm more of a girl than a boy in some ways, but because of my environment my boy side is dominate.

I was raised with girls, and they were always on me that I was too much like a girl. I remember my older sister once yelling at my mother, "mom, he walks just like a girl!" I remember in school some girls telling me I carried my books wrong and I sashayed when I walked.

I was always trying to fit in and just be another boy. I did not enjoy it at all.

I started noticing all of this when quite young, maybe about 9. I was a very pretty boy, I was never able to fit in and just be one of the guys. Gym class was the pits. I hated it. The other guys always, just always, picked up on me being different than them.

Even though I'm straight, I've always been turned on by "girly" baby clothes and panties. I guess this started when I was a kid and spent lots of time with girl cousins who were younger than me and still wearing diapers, pink plastic panties, sissy rhumba panties, etc. I also lived next door to a girl who was my age who still wore diapers at night and wet her pants during the day and I always got to see her diapers, plastic pants, and panties hanging on their clothesline.

Later in life, when going through puberty, I developed a big "girls' dirty panty" fetish and often stole panties out of hampers when visiting female friends and male friends with sisters. I'd take them home and look at them, feel them, smell them and sometimes put them on.

As I got older and more into ABDL fun, I realized that I love pink plastic panties and other baby clothes with pretty girly patterns (flowers, butterflies, Disney princesses) but I really don't like blue boys' patterns much. So when I met my wife and she started making me some baby clothes to wear, we went to a piece goods shop and bought pink and white material and soon she was making me frilly bottomed sissy pants and all sorts of nice things.

Now I have mostly pink plastic panties, a few pairs of sissy panties, and pink baby onesies. I don't always wear my sissy clothes, sometimes I just wear my diapers. But when I do get them out, I love them.

I guess the first time I really began to realize I was a sissy was when I was around 11. When I was 4 I had been been sent to live with two maiden aunts. They were very strict to make sure I didn't end up like my dad. When I went to live with them, they insisted on potty training me even though I could take care of myself in the bathroom. I did not like this because I already felt like a big boy and I tried to resist. So she bought a child-sized enema syringe.

She used it on me a lot and I got enemas, suppositories, and the soap stick all through my childhood. They had a friend who would babysit me sometimes, an older man widower. Sometimes I would stay with him for two or three weeks when my aunts traveled. They always left instructions for taking care of me including getting enemas to help with my nervousness. When I was around 11 I realized that if I fidgeted after he told me to settle down that he would take my temperature and then give me an enema to help me feel better.

I began to do it every three or four days, I would trick him into giving me an enema. It's hard to explain but I loved the feel of his hands on me as he took all my clothes off. and then the feeling of his finger with the vaseline slipping inside my bottom to get me ready for the syringe. Over time I really began to enjoy the enemas he gave me. Sometimes I would sass just so he would spank me and give me an enema. He said, "if you're going to act like a fussy little baby, I will sure enough treat you like one!'

When I was really little, four or five, my girl cousins would dress me up from top to bottom in girls clothes. I really didn't mind. I liked the attention. By the time I was nine, I knew I really liked dressing up like a girl and looked forward to those occasions where I was allowed to go out to a movie en fem.

HI for me it was atv5 yrs old played dresses up with 4 girls almost very day . Older siter started having me war panties daily . Love how they felt .Sister would dress me after enemas as female .So all around was girls .Still love wear bra panties and other garments .Now wife is giving estragen breast much large and much more female like so happy

I figured it out at about 7 , when my sister would dress me up in her panties , tights , and dresses , when my Mom & Dad were out for the night

She always told me she wanted me to be her little sister , and would dress me at any chance she got. As she and I got older , she would take me on shopping trips with her , and make me come into the try-out rooms with her, She would pick out dressed , skirts , and blouses for me to try on in the stores. What ever she bought , I had to wear for her , the next time my folks were out.

At 18 , I moved out from home , into an apartment , and got a job at a steal mill. My sister would come over almost every night , and spend the whole weekend with me , and make me dress up as her sister. She made sure I had a complete wardrobe of female clothing , right down to wigs , make-up , and everything that went along with being a girl.

We would go out to movies , shopping , theater events , and I was always dressed as her sister Bridgette.

Today my darling sister , Erin , is no longer with us , but i still dress up at home once in a while to honor her memory

I love you and miss you sis, and thanks for showing me , my true self...................

I guess that I always was real close to mom growing up.I got married the 1st time she left due to being Very little in the manhood dept. The 2nd wife is a lot more understanding when I became a diabetic and started wetting my pants and bed she put me back in diapers and pants the male ego was crushed she calls me her little wimp.She is a lot younger and as I found out very dominate.

I was 3 when I started wearing my sister's clothes. I knew that I should be a girl and wear girls clothes. My parents did not let me be the girl that I am. My sisters always helped me when they could. For my 7th birthday my sisters got me panties and tights so I could always wear them under my clothes. I have always been and will always be a sissy girl. I see men as lovers and girls as friends only. Being a sissy is way better than being a boy. I love to wear very feminine things. Now that I am an adult my parents finally call me by my real name Lisa. I am proud to be a sissy.

I was 5 yrs old and would wear panties around the house by 6 I was SUCKING my dad's cock and dressing like a girl thanks to mom dad would give me to his friends for sex. He would send me out nude

I was usually very straight except for a boy who lived across the street and when his parents were gone, we were 12 or 13 yo, he would bring out his dad's playboys and we would jack off together and sometimes jacj off each other but no oral. When i was 26 yo my live in girl friend usually would dress up in panties, bra, nylons, garter belt and high heels and we would play, suck and than make love. One night I pissed her off and she said no sex. So when she went to work and left her panties and bra on her chair so I got up andf put them on. that was where it all started. There was a laundramat down the street from me and late at night I would go over there and look through the pile of unclaimed clothes and pull out the bras and panties.. Many nights I would put them on and take my enema and have a good jack off. Later on I got married and my wife found them and made me throw all of my 'crazy stuff' away.

20 years ago I met a tranny and he recently became a female but we don't see each other because he moved away and wanted to settle down with a husband. We played sissy games and 'she' dominated me with force dressing anf enemas. Those were the good times. I have been looking and looking to find a sissy enemate but even this large 'silicone valley' there doesn't seem to be anyone around to play with. HEY are you out there? Please write soon. Cindi.

When i was picked up at a Bar, and didn't realize she was a Tranny but by then there was no turning back and have been hooked every since

It wasn't an epiphany my friend that I got into a relationship with just got me into it slowly.

Age 14. I had to wear a pair of my cousin's panties because I had wet the bed. I was hooked from the moment i pulled them on. Now I'm a Femboy and probably will trans. Along the line I started having sex with other Femboys. I saw a post one time recently about what Femboy carries in her purse. The list was sort of vanilla. So, my suggestion based on experience: lipstick, mirror, eye liner, spare panties, spare pantyhose or stockings depending on what you need, mace, most important…..rubbers! Femboys should always wear rubbers if they are the top and if you are the bottom make sure whoever is fucking you wears a rubber and put it on him/her to make sure. Best kind…ultra thin with good lube. I do both but really love being fucked so rubbers are always a must.

As per Webster's sissy = an effeminate man or boy also : a timid, weak, or cowardly person.

My realization moment that I was a sissy happened after college. I grew up wearing girls clothes but didn't give it much thought, just felt right. I enjoy dressing in femme and going to drag shows. Dating was hard to find man/woman who wanted to date pretty cross dresser. A bartender friend introduced me to a man who likes sissies. He was older and much larger than my 5' 9 & 145lbs. We became friends and met. Out at drag shows. At his house after a few drinks he asked me to be his sissy. He said if not it was OK , but to go to bedrommand put on clothes on the bed. There was a short pink little girls dress with full petticoats ,pink ruffle butt panties,training bra and pink high heels. I couldn't help myself , I put I on and braided my hair in two pigtails. Skipping out I said oh daddy I love my dress. Sitting on the couch he came up with a Hugh buldge in his pants. Sliding on my knees I swayed to and fro performing my sissy duties. He had a firm grip on my pigtails and told me to drop my hands and then pulled my head. I struggled with his 10 inch member and my throat gave way sliding forward till nose in crotch. As I realized my first sissy cum load was being directly deposited into my stomach I filled my panties with a sticky mess. He put me over the end of the couch , spanked my for messing in my panties and stuffed them in my mouth. Mounting me to bred he showed me who's boss giving three deep beef injections. I now met my destiny of being a sissy to a burley real man.

I would say about 11years old I had already been the family baby for 2 years when my sister asked if I wanted her dolls as she was growing up.

I said yes please I still have her ( her name is sally) I would play with her and take her to bed.

Then as my sister started to get more grown up look she would give me her old stuff.

One day I found my day over underwear change to girls I asked her to witch she replied that she knew I wanted to wear them because I was still playing with my dollies.

Even to this day I still wear girls underwear over my day diapers.