why do you cross dress how did you start

[luvitall]

what age what did you try on first bra anyone make you do it what do you do when dressed do you use makeup were do you get your things to put on

Once, as a boy, my mother and sister dressed me in sister's dance costume. It had a tutu like skirt that was very frilly, white tights and a sequined tight long sleeved top. They had me stand on the bed and look in mirror. I loved the look and feel of it. They had me twirl around and I remember the smiles on their faces. I felt good knowing I made them happy. They never mentioned it again nor did they have me do it again but I was hooked. Started secretly dressing in their clothes whenever I was alone. I would wear a pair of sister's panties to school under my pants. Loved night gowns and anything silky for how it felt against my skin.

At the time I bought I was the only boy that did that. I had such mixed feelings about doing it but did not want to stop. I enjoy hearing that others besides me enjoy dressing like a girl.

 

[BendoverRover]

I was about 10 or 11 and was peeking into my mother's dresser drawers. For me it's all about satin panties and pantyhose. I had no idea what i was doing, but rubbing felt good and I came but didn't know what an orgasm was or even what cum was. Have never looked back.

 

[nailu75]

Actually some bulls here made me start dressing and take pics. It was humiliating but also exciting

 

[h5t6ca]

Actually some bulls here made me start dressing and take pics. It was humiliating but also exciting

Can you share any pics?

 

[nailu75]

Can you share any pics?

Pm me i can share in private

 

[Azwoodguy]

I was about 25 when I had just moved in with a roommate a few months prior and knew I was bi. He suggested I wear bra, panties and stockings when at home. I started wearing them only when blowing him, but then just became a regular thing. All my male underwear was throw out and replaced with lace thongs. Over the course of 6 months, I started wearing skirts and dresses, and skimpy blouses. A friend would take me shopping and taught me about makeup. I shaved all body hair from my face down. We also started making little trips on BART from Concord to the city to meet friends. I became his house sissy slut.

 

[oldercuckcpl]

I had just turned 18 and graduating from high school when I actually had a guy stop and help me change a flat. I had always kept my legs smooth and was wearing short cut offs and a tee shirt. It was warm weather and he lived not far down the road in a little town on the way to college. He invited me to stop and have a cold drink and cool off. Once there he sat down on the couch beside me and put his hand on my bare leg. I didn't care and left it there. He started rubbing my leg and feeling me up. It actually felt good and turned me on. He ran a finger up my shorts leg and felt my balls. He had me naked and sucking his cock right away. He took me to the bedroom and put me on my back and put my legs over his shoulders. He was hard as a rock and slapped some lotion on my ass and fingered my hole. He asked if I liked that. I said a lot. He used two fingers then three then pushed his cock into me slowly then all the way in. I felt so full but felt good. He started fucking me harder and harder. There was nothing I could do but take it in that position. He was pinching and twisting my nipples and kissing me. I was on fire and wanted pounded hard. I got that good feeling like when I jacked off and cum all over my belly. He finally lunged deep and held it and I felt a warm feeling deep inside me. he backed out and fed his cock to me to taste. He seen where I had cum on my belly and said I must have enjoyed it too. I told him I did very much. He said you know you are a girl now. His girl. He said he was going to have me start acting like like his girl. He started buying me girls clothes and having me wear them. At first he loved to take me out wearing girls shorts and tops with panties and bra. I really liked him forcing me to and the humiliation. He would have me wear a dress and take me to Dallas or to a large flea market and stroll around. I would spend the weekends with him some.

 

[Rbm]

I started around 19, 11 with moms cloths. then when i got married it was the wifes and her make up and nail polish. ididnt hide it and she saw me dressed, she didnt say anything
later on i decieded i wanted boobs so i started on hrt
within 2 years i had decent boobs and told her i wanted a bra, so she bought me a bra and panty se , a nighty and a make up kit for xmas, a 38b bra
as istarted getting bigger istarte buyin my own things and couldnt stop till i had everything a women wears including heels and womens bathing suits, bikini.
after she passed away i got remarried and had to get rid of every thing, 60 bras and panties , plus everything else
i still allowed to wear bras and panties. Iwould love to be able to fully dress again

 

[Italianslutwife]

Started around 14 with heels and skirt. Found it so exciting and i never stop. When wife undestood my "secret" she push me so fast on a cuckolding and sissy evolution.
Now she meet other guys everytime she wish and i enjoy her and her bulls or other guys. Time by time i'm "pushed" by her into dogging for strangers.
Here i'm in a recent shot taken by one of her bulls...

 

[sissycuckrachel]

I began i think around 15 or 16....use to "borrow" my older sister's panties and bras when no one was home...dressing in them...eventually putting on one of her dresses or skirts. often came in them without even touching myself as i was so aroused by how her panties felt on my little penis. Eventually i began to look thru my mothers pantie drawer...would wear these occasional;y but not as often as my older sisters as they werent as sexy. I did love though wearing my mothers special nighties that she would wear for special occasions with my father, I often came inside these panties...as i imagined how amazing it must feel to have a guys hand under my skirt, dress or in the panties of my nighty, touching me, rubbing my little dicklette.
I tried to stop when I got older and eventually married but the urge to dress didnt leave me and I began wearing my wife;s things often while she was out working or shopping. She did eventually catch me and although initially pissed, and made me begin sleeping in the spare bedroom, she has come around to the fact that i am nothing more than a sissy and eventually, a cuckold as she began seeing men

 

[h5t6ca]

Started around 14 with heels and skirt. Found it so exciting and i never stop. When wife undestood my "secret" she push me so fast on a cuckolding and sissy evolution.
Now she meet other guys everytime she wish and i enjoy her and her bulls or other guys. Time by time i'm "pushed" by her into dogging for strangers.
Here i'm in a recent shot taken by one of her bulls...

Nice!

 

[h5t6ca]

I began i think around 15 or 16....use to "borrow" my older sister's panties and bras when no one was home...dressing in them...eventually putting on one of her dresses or skirts. often came in them without even touching myself as i was so aroused by how her panties felt on my little penis. Eventually i began to look thru my mothers pantie drawer...would wear these occasional;y but not as often as my older sisters as they werent as sexy. I did love though wearing my mothers special nighties that she would wear for special occasions with my father, I often came inside these panties...as i imagined how amazing it must feel to have a guys hand under my skirt, dress or in the panties of my nighty, touching me, rubbing my little dicklette.
I tried to stop when I got older and eventually married but the urge to dress didnt leave me and I began wearing my wife;s things often while she was out working or shopping. She did eventually catch me and although initially pissed, and made me begin sleeping in the spare bedroom, she has come around to the fact that i am nothing more than a sissy and eventually, a cuckold as she began seeing men

Do you fool around with bulls?

 

[sissycuckrachel]

Do you fool around with bulls?

yes...have embraced dressing and becoming a sissy cuckold

 

[creempieluvr]

what age what did you try on first bra anyone make you do it what do you do when dressed do you use makeup were do you get your things to put on

My wife started dressing me after the first time one of her Bulls fucked me and cum inside me. Now she said my transformation is complete.

 

[h5t6ca]

yes...have embraced dressing and becoming a sissy cuckold

Any story you care to share with us?

 

[h5t6ca]

My wife started dressing me after the first time one of her Bulls fucked me and cum inside me. Now she said my transformation is complete.

Experiences and pics you can share?

 

[nancyask]

a older guy slowly started me 2 years ago he was so slow at it i thought he was just playing around

 

[suntzuson]

me

Can definitely appreciate what he sees in you as a desirable sissy gurl