As A Young Boy I Loved Wearing Panties, Slips, Dresses, Anklets....

As a young boy I loved wearing panties, slips, dresses, anklets, all clothing labeled as "little girls" cept for tights. (I hated tights, cus, well, I had great looking widdle legs that was meant to be seen and not hidden).

Here's my story, or as I called them, 'ventures (transalated - adventures, cus Gad! Some words need to be shortened).

I have posted something like 25 of my 'ventures on EP as of 1/5/2011 (and have a nice collection of my "Giggelets" pictures on my Profile). All of 'ventures are true with only some name changes and minor embellishments. It all starts below...enjoy and member, my 'ventures are a lot more fun to read if you're wearing a pretty widdle dress and accessories like pink silky panties and a satin slip.

My Life as a Young Boy

About age six I began a career as a child model, modeling for a local agency with many national accounts. My mom was a licensed agent in this state and because of her own notoriety; she was able to keep me working regularly at the local and national levels.
By age seven I’d become a regular fixture on a local TV show helping to sell products and had established quite a portfolio placing me in demand, especially when a very pretty little boy was desired. Adding to my “fame” was being discovered by a nationally famous movie actor who fell in love with me, and whenever he came into town to film a commercial for a food product manufacturer, he insisted that I be in that commercial also.
Just before my 10th birthday while on the set at a national account that sold among other things, children’s clothing, it seems that a little girl model didn’t show and well, the agency rep asked my mom if I would stand in for her since I was certainly pretty enough to be a little girl. Mom consulted with me and despite my objections decided that I’d love to take that little girl’s place.
That day opened up a whole new adventure in my young life and by the age of eleven I’d modeled more dainty little panties, slips, petticoats, dresses and all other manner of little girls’ clothing more than I modeled boys stuff. Course, I wasn’t alone as the agency that I was under contract to actually had about eight other young boys who also modeled as a little girl, and we was in demand, even forming our own exclusive club at L & L, which Timmy Rogers, (our unofficial leader ‘cus, well, he had more seniority at the agency which his uncle was a partner), named “The Blue Princesses”. We'd always show up at assignments wearing our blue baseball caps. Course, the Dressers hated out hat hair but hey. And yes, we all hair somewhat long hair that could be styled or have a fall clipped onto it.
My modeling activities by and large were kept pretty quiet ‘cept for the immediate family, meaning my mom and agent, my much older brother, and that jerk who claimed to be my father, but wasn’t, trust me! Oh! The Catholic grade school I attended found out ‘cus I was being taken out of school on a regular basis to work assignment. The Church’s Pastor approved these releases ‘cus my mom was making rather nice donations to the church. It was Sister Mary Margaret, the Principal, who became upset with my modeling. She just about ate her black habit when she found out that I was also modeling girls’ clothes, even little girls’ panties. That just seemed so wrong in her perverted mind. She of course kinda leaked what I was doing and soon I was the School Sissy Boy and to her dismay, instant hero and boy god to most of the other kids. That was because they hoped that I’d get them modeling jobs. Naturally, the boy

Jockstrapers had a problem with me modeling little girls’ undies and dresses, but fortunately for me, most of the 7th and 8th grade boys thought I was a pretty neat widdle kid. Hey! I was extremely popular with just about every girl in my school and that further pissed off the Nun.
The down side was my playing on the school’s baseball team days were over since the coach didn’t “allow sissy little girls” on his team. That was ok ‘cus, well, I was off to Chicago most Saturdays modeling, and had even managed to convinced my agent to also represent my best friend forever, a classmate I’d nicknamed “Fraky”. Don’t remember why I named him that but it stuck even to this day.
The upside was that my agent, (mom) encouraged me and Fraky to practice being sissy, dainty, proper little girls to insure more modeling, thus more money for the old collage fund. Just about every day after school Fraky and me would race home undressing on the way so that by the time we reached my house, we was just about down to our ugly boy undies. I had a really good supply of very pretty satin panties, slips, and dresses that mom had made for me, enough to share with Fraky. We called our dressing up activity, “playing little girls” and mom loved it. That jerk, who claimed to be my father, just snorted and call us nasty names. My older brother just thought that we was 2 really weird little boys as he was leaving to stay with his friends.
Between the ages of about 10 and 14 Fraky and me continued to play little girls whenever we could, and I continued to model both genders, but as I approach 14 the assignments to model as a girl became few and far between.  Fraky never really made it as a model, ‘cus, gosh, he just wasn’t a pretty as me.
During these years I enjoyed many adventures and loved every minute on my modeling and acting activities, but there was some painful times also that have played a major role in my rejecting the Catholic faith, one specifically, the week in the 5th grade when I had to attend school every day for a week dressed like a very sissy little girl for “teasing” a little girl in my class.
Over the years I have researched the idea of young boys wearing girls’ clothing both by choice and by force, and have created more than 1000 pictures of “sissy dressed boys”, some funny, some sad, some happy and cute, some real, some “Photoshopped”, but none sexual or pornographic, because my experiences were never sexual or pornographic. I did have an uncle who often took some “interesting” pictures of me.
My only anger is directed at that Catholic Nun who sought to deliberately hurt me and my mom. I am also a bit angry with those who sit in judgement of boys “playing little girls” by choice.  I grew up to be totally straight and married to the same wonderful lady for 40 years until her death. We raised a great family and I enjoy grandchildren and a very special Godson adopted by 2 gay moms when the saintly religious people threw him away and didn’t want him.
I do believe strongly that this world is changing and the day is near when women will be the “men” and “men” will be the women and find themselves 2nd or 3rd class citizens as we males have so dominated females for centuries. We’ve earned every injustice that women will inflict on us
theBillyandBudBear theBillyandBudBear 66-70, M 17 Responses Jan 5, 2011

Your Response


When I was 5yr old my sister dressed me as a girl and I liked it. My mom finally found out and let me be a girl. I was home schooled most of my life, but did go to a girls private school and wore a girls uniform to school.

In my mom and sisters eyes I was a girl. Since 5 yrs old I have never dressed as a boy, I dont own any guy clothes.
I now live with an ex-girl now that liked me and even tho she found out I lived as a girl, she still wanted me to be her personal maid while she travels with her job.
She lets me wear dresses everyday and look like a girl all the time. All our neighbors know I'm a sissy girl and most of the towns people. I go out grocery shopping and run errands as a girl and everyone knows I'm a sissy and I dont care.
I like being who I am.

I am so impressed with your evolution beyond the hate spewed by that horrible nun. She must have had major personal issues with her own self image to take it out on a young boy. Congratulations on living your life the way you wanted to! You are my hero.

I enjoyed your story sounds like you have had a lot of fun. I really love to wear patties , pettiecoats, dresses with full skirts, ect. My ultimate cross dress is in a wedding gown with lots of crunchy crinnoline and a pretty veil.

A very interesting story, I liked it.

Hi and thanks so much for the story - I have to admit that my interest in dressing up is sexual, not professional! However I agree with your point of view on life. I live as a heterosexual man but do not have any hangups about gay people and as I say, I do enjoy cross dressing for sensual enjoyment

wearing a dress or a skirt has nothing to do with one's sexual orientation, you could wear a gorilla suit and still be gay. Most guys who do wear dresses and skirts are straight, married and have children.

Were you ever forced to wear tights?

Not really cept it took a widdle encouragement for me to wear them, which I only wore when I was modeling them for the costumer or the shoot directed demanded them be worn. For which I was well paid.

I'm with Billy -- tights are yucky, too much like pantyhose, which I don't like either.

The four things I hate that most crossdressers love are: makeup, bras, pantyhose, and high heeled shoes.

Wow! Someone very smart agrees with me. Melodie13! Please read this. Thanks Mr. racer512 person!

I don't wear Heels or pantyhose or bras, however I willwear tights because they help with circulation and give warmth in colder weather. I can't stand make-up I feel my face is DIRTY and it irritates me. I wear skirts 365, no pants, occasionally shorts depending on what I'm doing. I wear sandals (even in winter) or sneakers.

OK! I still don't likes yucky tights!

Me either.

3 More Responses

Some things are better left unsaid. It is better to remain silent and thought a fool than to speak and remove all doubt! No punitive action can equitably balance historical injustice. Why? Because those responsible for the injustice have passed on. You want to enslave half the species for no other reason than they have an outie! Besides the fact that you are so overstating the oppression of women. Make no mistake that vast numbers of women have borne the brunt of abussive males attitudes. Rather than women adopting those attitudes toward males they should celebrate the demise of such attitudes when those abusers go to the grave. Ezekiel 18 'the sons shall not bear the sins of the father...'. What you propose is to make women perpetrators of what men have in the past perpetrated (not to the extent you say they have). Take some classes in logic or something please.

I have been dressing in female clothes since age 12 and even started sex change treatment- stopped for my career's sake. I only really feel myself when dressed as a woman.

Sad to do such violence to yourself for a career. Living with such tension is hard, and I hope you find peace.

Sweet story. Would have given anything to be a panty model!

That's the trouble with these models you know. Can be right divas! :-)

I took to experimenting some time in my 20s. I can't remember 30 years later, but probably when curiosity overcome me and I tried on one my sister's short skirts.

A point from 3000 miles E of Boston, Mass. re putting your pictures on-line. Without viewing them, I do not doubt they are all simple, ex-catalogue adverts, but still dangerous to down-load in the UK whatever the style, source and context.

I do change a few names in some of my 'ventures to the names of some of my EP friends, but the names, Fraky, Blake, Logan, Devon, Joey, Mary Beth, and that bratty widdle girl that lives across the street from me...Doris are all very real, also Austin, and we all meet for lunch every month. Well cept for Devon cus he lives in Chicago. The rest of us all live within 50 miles of each other and are all basically retired.

I started wearing my cousins panties when I wa 10 yo..I LOVE the feeel of sexy panties against my hairless **** and balls all day.

i love tights over panty hose they are much stronger and do not run like pantyhose do there is nothing like white and or black tights on your legs they are very comfortable but very hot in an uncondtioned room as i found out once when i wore them for a masquarade show a few times it was kind of uncortable wearing tihgts in a hot room and was kind of glad to get out of them the only other real problem was whuch and what bathroom to use while dressed in andd as your girlself this is kind of very confusing for so mnay of us fory tuatly i was in a large hotel at the time so was still able to sue the male restroom although i would really ahve rahter used the ladies restroom whild dressed in girl mode usually girls restrooms are much clealner and nicer once you can get in and sue the stalls as they ahve no urnails becasue girls do not need those! ah well!?

To everyone reading this story!

Wednesday February 23, 2010

Is PINK SHIRT DAY throughout the world, and is your opportunity to STAND UP to punks and bullies.

This day has nothing to do with any other agenda but protesting against bullies who hurt and humiliate innocent people of all ages and genders’

I’m man enough to take this stand against bullies and hope that you too with wear a pink shirt on Wednesday February 23rd to let the punks and Bullies know that they, not us, are the real “sissies”.

Hmm...Now (2013 and beyond) the "International Day of Pink" is the second Wednesday in April -- in 2014 that will be April 9. See

Never could stand tights too. Except maybe on clowns, and oh yeah, on men who dress up but don't shave their legs! Yuck!

Dressed as a girl at school for a week! Ouch! Double ouch! With petticoats 'n panties 'n slips? That first day musta been a real bumma ( just my Boston accent). At least you didn't have to wear that stuff to my grammar school. I know some of those kids at my school wooda tried to kill you. All you had to do at my school was be talking to a girl for too long, or sitting with them at lunch, and you'd have a "dance card" filled with young snots that wanna fight you outside after the last bell! 'Course, most times they wouldn't stick around after school, and that gave you fodder to use on them the next day. You know. "Hey Richie, where were you after school yesterday? I waited around and you never showed. Ya mommy calling ya, huh?" And you had to say this with other kids around so they knew you were the one who wasn't a sissy. The false bravado we had back then is comical, thinking back on it today. But if you stayed with friends, you would be ok 'cause they'd stick up for you. Sounds like you had friends always there for you. Unfortunately, I didn't have many friends in grammar school ( grades 1-6) 'cause I sometimes would have accidents, and nobody wanted to be seen as a friend to a kid that pissed their pants, except another kid with the same problem. But, hey! I survived!

Just a note about taste and preferences. Maybe this has changed in Chicago, but I remember often seeing women with unshaven legs, with and without nylons, and apparently feeling no less pretty for it. "About taste there is no point arguing." (old Latin saying)

Thanks Bobbie, I have checked out your great comments and I hope to post a new 'venture later today.


I've look at your pictures and must said that they were just wonderful. Thank you for sharing them with us. I've commented on many of them and I hope you will read my comment. Please keep up the good work. Bobbie