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Brianna’s Feminization Story – Crossdreser Society | An Online Resource for Crossdressers | Transgender

Brianna’s Feminization Story

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Brianna reveals how his feminization took roots at a young age

How his aunt played feminization games…

Here is my story of my early memories of my feminization

A lot of us lived with my grandparents in Queens right after the war.  My aunt was married to my mother’s brother.  She was a high-class southern belle, very sexy and flirty, judging from photographs.  I was the pride of the family and I think she was jealous of all the attention I was receiving, especially after her first child was born a year after me.  Among the clothes I was dressed in was a French beret.  She teased me that I looked like a girl in it.

I didn’t want to wear it after that, but my father made me wear it.

I don’t know if she had anything to do with that, but in later years my father claimed that she had made a play for him, and she said the same.  A little later she caught me playing with myself.  I was probably 3 years old at the time.

She said she was going to tell on me.  Subsequently, my father and I took a walk to a soda store about 3 blocks from the house.  As we turned the corner onto the main road, he said to me “I understand you’ve been playing with yourself down there.”

crossdressers auntRight away I thought of my aunt, and knew she had snitched on me.  “Better stop,” he said, “or you’ll turn into a girl.”  This inflamed me with sexual lust, but he probably took my reaction for embarrassment.  I told him I would stop, thereby lying to him for the first time and acquiring a secret.  I am convinced my aunt told him to say that to me, assuring him it would stop me from masturbating.

I have since learned, from a cousin-in-law, that my aunt played feminization games with at least two of her sons.  Just before we left for California, I was spending the weekend at their house and she got her son to grab me from behind, and proceeded to kiss me, wearing thick red lipstick.


She spread it all over my mouth, making me look (in her words) “just like a girl.”  Then we returned to my house in Queens and suddenly my mother announced we were leaving for the airport in 5 minutes.

crossdresser goes to CaliforniaWe flew to California to find my deserted father and make him pay child support.  We left practically everything behind.  All I took were a small fortune in comic books and the fetish my aunt had imprinted me with.  The comics are long gone, but the fetish has stayed with me all my life:

Sex = changing into a girl.



About the Author:

Hi, I’m Marcy Simpson, founder and creator of Crossdresser Society. I have been a crossdresser for over 2 decades and I am also an author, photographer, entrepreneur, and admirer of the feminine realm. I currently work and live in Los Angeles, California.


  1. jaque  August 20, 2014

    i think we all have been in similar situations mine was an older sister but had i not had inclination and enjoyed it than itv would not have happened it started when i was 14 i shared her panties with her wore her skirts and dresses and her make up i was jealous of her long hair i loved the dressing up and still do wxcept now i have wigs

  2. Ajay dixit  September 23, 2014

    Hi every one sexy. Every one like feminine dress as i like to wear makeup as well outfit .

    • Frank mobillio  January 9, 2018

      I never got into make up but when i was 13 i began taking a interest in women’s lingerie and clothing and when no body was home i would dress up in sexy lingerie and put on a nice dress and get around the house wearing it for a few hours,i never heard my mom come home i was sitting on the lounge playing with my self my eyes closed when i heard a voice say what the hell are you doing,mt eyes opened and my mom was standing there looking at my cock,she yelled at me to get changed i quickly pulled my dress down and run to my room an changed,I never dressed up again,mom and dad divorced not long after and dad’s girl friend moved in,she was super hot and sexy,i just turned 15 and noticed she wore very sexy lace lingerie and sexy clothing. I went hard,they were going out for tea i couldn’t wait until they were gone,I wanted to see what she had. So as they left i went into their room and i went through her draws and i took out silky black lace panties and matching bra a pair of silk black stockings and suspenders a long silky lace petticoat and in the wardrobe i got a long red maxi dress and a pair of hi heels,i dressed up in it all. I found a 6 inch vibrator and a 5 inch. I put 6 inch down front of my panties and the 5 inch i lubed up and pushed it up my arse.it was really dark out side i looked around and could see no one so i grabbed a long wig and put on then i resided to go for a walk around the block,a few people saw me and said hello i just nodded they didn’t know that i was a male in female clothing so i began to go for a walk every night dressed in women’s clothing

  3. michael  October 17, 2014

    Bon soir, Marcy!…..Ginger and I went out for awhile…Happy hour at the Quarterback Club….I go there quite often… usually with another girl….We hung out at the bar, near the piano guy……I never knew how those guys can play anything you can think of…… A small group started up a little later….Both of us danced a lot……we can do a two-step in a tight skirt…..small steps….turn around by un-weighting one heel, and push with the other foot …..it gets you noticed…We both slow dance, also……I sink right into a man’s arms…..sometimes it feels great…..other times, forget about it…… sometimes it seems like there’s a war going on inside me……Later, we watched that story of Brianna …..and her entrance into crossdressing…..we didn’t know if that picture was her…..omg…really beautiful ! …..kind of a sad story….tough being ridiculed by you own family when you’re young……. We are very impressed by how people tell you things like that….you are so warm….been through it yourself…..you’re giving us so much confidence….to get out there and try…we love you, Marcy!….hugs …kisses….Ginger and Mitchie

    • michael  November 11, 2014

      Bon soir, Marcy …..I saw some pictures of you that I hadn’t seen before……some of them from an office setting…..
      I would KILL for your legs, Girlfriend…..warm hugs….I love you…….Mitchie

  4. Frank mobillio  January 8, 2018

    I am a straight married guy mid 40 and yes I love wearing sexy lingerie and dressing up in women’s clothing,i began crossdressing about 13 years ago. I don’t believe it should be called crossdressing as clothing has no gender and because lingerie is made of a different material doesn’t mean it was just made for females, when I was about 14 women’s clothing and lingerie began to excite me because my 21 yr old brother’s wife who was living with us wore very sexy lace lingerie and sexy clothing,one day when no body was home and i was there on my own it looked like it was going to rain so i took washing off the line and when I got half thru taking it off i came across sister in law’s lingerie,first i took off her panties they were so smooth and sexy,i looked around and could see no one so i put them down front of my shorts then I took a silk lace bra off the line and a long deep plum colored silky lace petticoat,I wanted to know what it was like to wear so i raced in side took my own clothes off and put on the panties,bra and petticoat,I went and looked in the mirror and i liked it,i went into sister in law’s room and went through her draws and i took black stockings,suspenders and some clothing which was a long yellow dress.i put it on then walked around the house. I fell in love with wearing women’s lingerie and clothing,I was getting drink from fridge when i heard sister in law call out if i was home,i froze i couldn’t hide so i slipped out back door around side of house and climbed in through my bedroom window and once in i went to lock my door but wasn’t quick enough because sister in law opened it and walked in,there i was standing there dressed in all her clothing,she stood there staring at me then asked what i was doing wearing her clothes i said i only wanted to see what it was like to wear,she asked how long have i been crossdressing i told her that it was first time,she said so how did you enjoy it was it what you were expecting,then she locked door and sat on my bed. SHE asked why did I pick her stuff to wear so i told her that it was the sexist thing I ever felt and said she wears sexy things and i said please don’t tell anyone about it,she promised she wouldn’t say anything then told me a secret and made me promise not to tell anyone i agreed,she told me she caught her brother dressing up in women’s clothing and if i wanted to wear female clothing and lingerie around the house she said it was fine by her and asked if I had any women’s clothing or lingerie of my own i said no,she unlocked the door and said follow her,we went to her room and told me to sit on her bed,she left room then came back with a empty suitcase and opened it up,she was going through her draws and took out 5 pairs of panties 3 bra’s and 2 pairs of black stockings and put them in suitcase then she open her wardrobe and took out 3 maxi dresses and a knee length one,then took down 4 mini skirts and 2 maxi skirts a half slip and a long silky lace petticoat and put it all in suitcase and then closed it.she open her draw and took out a pick and black 2 piece bikini and handed me and said you might like to wear it in spa or pool when you are alone,she said i hope you like what ive just given you i nodded and said yes and thank you for everything,as i was leaving her room she said if you want to wear something different i don’t mind if you take some of my things as long as you asked first and i don’t mind if you want to dress up and it’s okay to wear it in front of me,i crossdressed for about 3 yrs and some times my sister in law would tell me put some of my things in the car and she would take me somewhere so i could dress up,it would be dark and sister in law would tell my mom and my brother we going do bit of shopping,once out the front gate she would ask where my things were i would say on back seat,she would pull into a park and say QUICKLY get dressed up in the lingerie and put on the pink long skirt and the black lace blouse she gave me and once dressed up she said put on the black pantyhose,i got out of the car and she went to the boot and took out a long dark brunette wig and a pair of hi heels she told me put the hi heels on while she fixed the wig on me,she grabbed my hand and led me under the light and said now stand still then she had her phone and took some pictures of me,i said what you doing that for she said for our eyes only.she showed me the pictures and i couldn’t believe that i looked like a girl,sister in law said let’s go and i told her i couldn’t go dressed like a girl she said people won’t even recognize me so i got into the car and she drove we went down the main street she stopped at traffic lights and people walked past,i couldn’t believe nobody recognised me,as we were driving sister in law said did you enjoy it,i nodded yes she asked if I wanted to do it again soon and i told her that i would,,she said come Saturday she would get some make up and for me to pick out what i wanted to wear..i went into her room and picked out a long white maxi skirt and a cream colored silk lace blouse and a long white silky lace petticoat…i went and put them in a bag and took them out to the car,she wrote a note and said we going to the pictures,we got into the car and drove to a deserted building,she told me to get dressed in what i was going to wear so i did,i even had on my stockings and hi heels,she put the wig on me and then started to put make up on me,once done she stood back and took a good look at me then got her phone and took some pictures of me and then showed me and said what do you think,i said i don’t look like a male and she said when we get to the pictures pretend you have a cold and put hanky over mouth,we parked car i was nervous about getting out but she convinced me she held my arm and we walked to the pictures and stopped so she could pay then went in and found a seat up the back on our own,,she whispered in my ear and said i looked hot and kissed me she then put a hand up my skirt and inside my panties and jerked me off,she put my hand up her top..we became discrete sex partners and i dressed in women’s clothing and lingerie when it was just the 2 of us

    • Marcy  January 8, 2018

      Hi Frank i loved reading your story. thank you for taking the time to submit it. feel free to email me some photos of you and we can post your story on the site as a post for all the other girls.
      Thanks again,



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