First Time Crossdressing

I must have been about 13 , and in the boys brigade . We had end of season display , and I had to dress as a woman for a sketch in the show . I was made up , and dressed in a bra ( stuffed up ) and black tights , and a dress , and a pair of 2inch heeled court shoes all donated by the leaders.
It was a total embarrassment , to have to wear all this in front of my fiends and family , but after the dress rehersal , I had to take the stufff home with me and keep it for 2 nights
Left alone in the house on one of those nights , I had my first real CD experience , as I tried on my costume , and sat around the house, paraded up and down , and experienced my first ****** , dressed as a woman .
I have been dressing and orgasming in dresses ever since .
miranda69 miranda69
9 Responses Jun 18, 2011

Wonder how many guys would like cross dressing if given a chance

Lovely story. Had very similar experience with GF on Halloween. She was football player and I was cheerleader. Bra, panties, wig, makeup the whole deal. After party j went home still in full regalia very horny. All my friends were gabbing me and lifting my super short skirt all night. I had an enormous ****** before I washed up for bed. I even slept in the panties after.

I haven't since my teens, but I have been wanting to in recent time.

I started trying stockings on in the bathroom where my mom and sister would hang freshly washed stockings. Initially my mom....fully fashioned stockings and then the slow switch to RH&T's. My sister wore RH&T first and it took my mom a bit longer to convert. It went un-noticed that I was bathing more often and longer!<br />
My wife knows that I like to dress and we enjoy an occassional 'frolick' with hold-ups on. So far I have not pushed for 'more' and I try to mix it up by not wearing every time that we have sex. She does notice that I perform with more passion when I am wearing and if we both do we play longer....I need to point that out more----hint (to wife)!---hint(to wife)!

I started wearing womens clothes about age 8. And had my first ****** wearing my moms nylon nightgown. Am married now told my wife that I liked to wear womens clothes before we got married. She has helped me accept and enjoy being a crossdresser.

You made the right decision telling your wife before you got married. I was afraid to confront it. It has come up several times over the years and she does not accept it. I have decided to be pantied full time now and that has not gone over very well. I hope someday soon she will accept me and let me dress in front of her.

I did not realize I wanted to until after I got married. So I have never brought it up. I am pretty sure she would not like it. I have hinted, but its hard to bring up. She does not really like to dress herself up anymore. So why would she want to help me do something she doesn't find pleasure in?

One Halloween, My mom helped me to dress up as a girl, the clothes belonged to one of my cousins. She let me keep the stuff &amp; I hid everything so my father wouldn't find it. I about wore out the panties trying them on. So I graduated to her lingerie drawer, memorizing how everything was placed &amp; folded. Then I could put it back exactly the way it was. I'm sure she suspected, but never said anything. It took me a few years to get up the nerve to dress up as a girl again, but by that time I was in jr. high &amp; her stuff fit me. By then "pleasuring myself" in fem had been reinforced by practice to an art. I knew what I wanted to wear, a longline bra, a girdle, panties &amp; hose, covered by a tacky, pink, chenele bathrobe. I clipped curlers to a scarf, put it on my head &amp; covered it w/ another scarf to make it look like my hair was in rollers. She helped applied make up to my face, that gave the appearance I had cold cream on. With a pair of sunglasses, no one could recognize me. My feet were biggerer than hers so this presented a challenge. She came up w/ a pair of sling back weddgies that were easier to walk in then the high heels of hers I would squeeze into &amp; walk around the house in when no one was home.. There was still the stigma given to any guy dressing up as a girl, but no one could figure out who I was. I felt safe, but felt so alone, hoping I could find someone else who enjoyed dressing up the way I did.

My initial attraction to intimate womans wear was when my older sister (12) and I briefly shared a bedroom. I would take her nylon slips and panties into bed with me. It all started with a favorite 'blankie' and the satin binding. My mom I guess thought it was an inocent extention of the blanket and didn't fuss about it. She would take things away from me (if found in my bed) but she never made me feel like it was wrong....the seed's were sown!

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That's really cool - having your first ****** all dressed up as a woman. I'm so glad that you were able to transition from an embarassing experience to a lifetime of wonderful ones. Thanks for sharing.

Wonderful story, thank you for sharing.

Yes it is eurprising how a dressing up experience can untroduce you to a life time change

I`m really pleased I did; I was out buying new pantie hose for the winter this morning; got some nice panties too, trying them later! xxx

Having your first ****** while dressed in women's clothing totally cements the fetish. My first ****** happened while wearing pantyhose. Loved ******* in them ever since.

Interesting to note that you had your first ****** dressed in womens clothes. I`ve noticed that I have a better ****** when dressed in womens clothing, particularly a nice black skirt and crisp white blouse...that really turns me on.