Funnest CD experience?

[Jill]

So which experience in your whole crossdressing life was the most funnest for you? I am very much still in the closet, but for me I have two times that stand out as the most fun. The first was when I told a female friend about it and she was totally cool about it. I wnt over to her place one day and dressed up, and she did my make up. It was the first time I had been dressed in front of anyone. The second was when my parents went out of town so I went to their place to "house sit" and I had the place all alone to myself. Late at night, when I was all decked out, everything but makeup and wig. I walked outside to my car, which has tinted windows, and went for a drive. I stopped at a school that was very dark and went for a little walk. It was so much fun for me! I loved the wind blowing against my legs and up my dress. I know it's not much compared to others, but I want to know what others have done.

[Ivana]

As of yet I haven't driven out in my car, But I have walked up and down my street. I especially lilke windy nights when I can feel the strong breezy air flow up my skirt or dress and my nylon hosiery.

So which experience in your whole crossdressing life was the most funnest for you? I am very much still in the closet, but for me I have two times that stand out as the most fun. The first was when I told a female friend about it and she was totally cool about it. I wnt over to her place one day and dressed up, and she did my make up. It was the first time I had been dressed in front of anyone. The second was when my parents went out of town so I went to their place to "house sit" and I had the place all alone to myself. Late at night, when I was all decked out, everything but makeup and wig. I walked outside to my car, which has tinted windows, and went for a drive. I stopped at a school that was very dark and went for a little walk. It was so much fun for me! I loved the wind blowing against my legs and up my dress. I know it's not much compared to others, but I want to know what others have done.

[rhiannon]

Hi Jill,
My only experience of going out was also the most thrilling I have had.
It was night, I put on my panties, suspender, hose, bra, skirt, blouse and heels , then my trousers and sweater on top. Left the house and got into my car, I saw my neighbour on the way down the garden, and felt like they knew. I took off the trousers and started to drive, once out of my road took off my top and drove to the local "common" land, had a smoke and stepped out the car. I too enjoyed the feeling of the wind between my legs. I wasnt sure what to do next and got scared someone would drive and by and stop so I got in the car and left for home. I have never been out the house dressed since except wearing panties to work, but this is even more scary as in construction its easy for t-shirts to become untucked and accidentely flash a bit of ass.

luv rhiannon

[Pete262]

My experience wasn't funny at the time but looking back on it I have to laugh.

I've only been out female dressed once which was last November. I never wear anything too obvious even around the house... my taste is more 'clothes that can pass as male to all but those who I want to know'. So on this day out to the gay village with my girlfriend I was wearing socks, black pumps, matching bra and knickers, pin striped black trousers, and a black blouse.

Completely unrelated to what I was wearing a guy poured drink on me to try to distract me while his friend stole my wallet. The robbery didn't work but basically the guy came down from upstairs and threw his glass in my face which left me bleeding and needing to go to hospital to get stitches. So there I was at 7pm on a Saturday wearing a low buttoned blouse with my bra visible getting stitches in a sort of dental chair with the plastic surgeon peering down my top. After my treatment was done we went back to the bar and got free drinks on the management all night! It wasn't funny at the time but now it makes me laugh. Talk about a worst case scenario for a first time out!

[Vivian Best]

Hi Jill,

Two experiences stick out in my mind. The first one didn't seen funny when it happened but as I look back I can laugh about it. My wife had left the house and I got my clothes and had panties, pantyhose, girdle and bra on when I heard the security system in my home beep indicating a door had opened and I heard my wife coming in the kitchen. I was in the master bath in all my glory and all drab clothes were in the bedroom which can be seen from the kitchen. I made a mad dash to the bedroom to get my drab. I saw my wife and she was looking my way. Apparently it didn't register with her what she saw because she got what she came back for and left. That was the nearest I ever came to getting caught.

The second was when I went out dressed. I went to a store that was supposed to be closed which gave me a chance to get out of the car and walk around and look in the store window. As I was looking a man came out of the store and said "Miss" you can come in if you want to. I turned and left saying I would be back later. I still remember being called "miss".

Vivian

[scoob]

Hi Jill,

my best and worst times both involved the urge to get away from civilisation, out into wild countryside, and go for a hike in full regalia (panties, suspenders, stockings, basque, slip and miniskirt). As a fully paid up coward I went out late at night, in dark weather. The best thing was walking along a lonely footpath, into a storm, wind and rain lashing me senseless and the bushes and trees and tall grass waving me on, on on... The feeling of total security and liberation was sooo good. I walked for miles.

The worst time was to same place, and blundering into a herd of sleeping cows. They woke up. Total panic! I arrived home shaking and wondering what on earth they made of it all (you can imagine the gossip in the milking parlour next day...)
Beats being *made* by people, if racing pusle is any measure.

[Stelli]

That happens to be during my high school. I have had this crazy female friend of mine that shared a school bench with me. She and couple of other girls (about 5-6 of them) made some afternoon party at her place. I was not only male at the party there was my best frend at that time with me - two of us and a bunch of crazy girls. I do not recall if we drunk or not, I do not believe so, but at some point girls decided that we are pretty but they can make us more pretty and that they should makeup us two. We looked at each other, started lauging and agreed. Then it was a lot of laugh, faces, gigling, tickeling etc. They did not dress us in clothes just did makeup and made photos with polaroid camera. I believe that I still have that picture somewhere among my photos. I remembered that I was astonished how different I look after I apply makeup. I remembered also that this was the most ulitmate experience at that ime. At that time I was not having a clue about CDing. Years passed on when I start feeling that I should do makeup. Now I rarely dress if I do not have chance to have makeup too.

[Abraxas]

Well... I'm female- bodied just so you all know (if you haven't gathered as much). One time when I was about fifteen I went to the loval skating rink with my (then) boyfriend Josh. This was back when I could pass as a boy, whether I wanted to or not. People just assumed I was (not any more, unfortunately). I was there with my friend also. It was really funny because all these girls kept coming up and asking my boyfriend and me if we were gay. I just thought that was slightly funny and a bit embarassing. This was before I really realised that I do, in fact, crossdress and I am a tv. Now that I understand the whole psychology of it and everything I wish I could pass. If I really tried I'm sure I could...

[Julie]

My first "funnest: experience was one Haloween. My wife dressed as a gu and I as a ..... yeah, you guessed it, a GIRL! What a surprise!

Anyway we wnet to a local bar where they were having a costume contest. We met a bouple who were an elevtrical plug and socket. I don't remember him much but she just couldn't get enough of me. I was pretty thin then and was wearing a size 7 dress which fet quite well. She was asking me all sorts of questions and being very complimentary. When it came time to use the bathroom I said I was a bit nervous about walking into the men's room dressed like this. So she insisted we (she, my wife and I) all go to the ladies room.

I went into one of the stalls until my heart stopped pounding and then came out. I figured I might as well enjoy this so I went up to the mirror and touched up my makeup and hair. My wife was urging me to leave while the other girl was watching with what seemed amusement.

After that I used the ladies room all night without incident.

What a night!

Julie

[Lawren]

My 1st time out was "the Halloween thing". I went dressed to kill. Of course it caught all of my friends completely off guard. We went bowling and had been there for a while when another friend arrived. One of the guys decided to "introduce" me to her. I sat there quietly so I wouldn't ruin it with my masculine voice. The ruse worked. She never did recognize until we told her the truth about 30 minutes later. I was struggling hard not to break out in hysterical laughter.

Later, I went to the restaraunt where I worked and stood before a co-worker who completely failed to recognize me also.

[windycissy]

When I was just getting into dressing, I used to bring my girl stuff with me on business trips and make myself over in my hotel room. In those days I didn't have the cajones to go outside my room, but one day I got up enough nerve to order room service after I got myself all dolled up. Just when I heard the room service waiter knock on my door, the telephone rang! It was my bosses' secretary! In my girl's voice, I shouted, "Just a minute" to the waiter outside the door. Fearing he would be able to hear me talking on the phone, I was stuck having to talk to my bosses' secretary as a girl! So I told her to please hold on for a moment, opened the door, waited for the waiter to leave, and then picked up the phone again and spoke to her in my natural voice. I can only hope she suspected that I had a chippie in my room who answered the phone before I took it away from her...Ask Windy

[jessicadiane]

My funnest experience was going out dressed for the first time .Although it was just going out and eating lunch at the park. Hopefully I will have "funner" experiences in the future besides just going out.I would love for a guy to treat me like a lady the whole time.Opening the door,giving me flowers,etc.Well a girl can wish anyways

[joesephine]

Lawren
Hollowen, is coming up soon. Sounds like a great idea. I've never thought of that before. I'm off to the second handstore. I don't think I'll make it an offical coming out though. There are usually some single gg in attendance, maybe I can impress one.

Joesephine

[babe4life]

My favourite was at an end of year function for the student newspaper I was working on. It was always a fancy dress party and one year I decided to put on jeans, make-up, wig, the works! It was getting quite dark by the time I got there (still early for the do though) and went to one of the other staff members to give them the money for the evening (I was financial manager at that stage). The expression on her face was *priceless*. I still have photos from that evening. Of course I set the precedent and the next year half the staff were in drag! Some of them were very good too. LOL.
Love,
Vicky

[carolynhcd]

My funnest experience was back in the '80's when I lived in the Bay Area of California. I worked at a large law firm and was close friends with a GG who was also from North Carolina. She knew I crossdressed and was comfortable with it. She called me up late one night and said she wanted me to come stay with her. I told her that I was totally en femme and had too much to drink and would not drive into the City under those conditions (I lived just south of San Francisco, in Daly City). She said, "Let me call you back" and hung up on me. A minute later, the phone rang and she said that she had called me a cab. I swear to god, girls, I only had time to get out of bed, check my makeup and grab my purse and there was a cab honking its horn in my driveway. I ran out the front door, locked it and went down the steps to the cab. I tried a useless falsetto to give the cabbie instructions as to where I wanted him to take me and settled back to enjoy a rocket ride into downtown San Francisco as a girl. The cabbie was of foreign nationality and my girl voice was useless, so I had to bark orders to him after several worthless attempts at speaking like a girl. Finally, he dumped me off at her apartment building and I had to run in my 5" stiletto heeled pumps up the front stairs and through the doors to the elevator. A straight couple got off the elevator when it arrived in the lobby and they gave me "the look," but I didn't care as I was so frantic to get upstairs to the safety of my GG's apartment. She had left the door not only unlocked but standing wide open and I swished in in a cloud of perfume and hastily bolted the door behind me. I went through to the bedroom only to find her passed out on the bed in just a pair of pantyhose and a bra (she was quite voluptuously endowed). I woke her and berated her for the anguish she had put me through and she just laughed saucily in my face and told me to "get over it, ****". We watched MTV and she passed out again and I spent the night looking at her beautiful body and wishing that I looked like her. Finally, I went to sleep about five in the morning and the next thing I knew, the doorbell was sounding and she sat bolt-upright next to me in bed and said, "Oh my god, the tile men are here." I said, "What the F... do you mean 'the tile men are here?'" By now, my five o'clock shadow, which hadn't been convincing at 1 am, was even less convincing at eight am. I panicked and she hustled me into a tiny room, too small for a bedroom, and in which she had dumped every soiled undergarment she owned (and she owned plenty) to hide until the tile men had accomplished their task. I spent three hours in there, afraid to cough, and indulging a trait that some of you will need no explanation for. Finally, she opened the door to my perfect prison and saw me holding a pair of her panties to my nose and my hand in an improvident spot. To my delight, she just burst out laughing and called me a ***** and we both became hysterical. I sternly demanded, between gusts of laughter, that she take me home immediately. I instructed her to get dressed and go out and bring her VW Beetle up to the front door of her apartment building, as I would now have to negotiate my way out of her apartment and building in broad daylight. Fifteen minutes later, I saw her car pull up in front of the building and I made my mad dash for freedom. I encountered many people in my escape and everyone of them knew at first glance that I was a sissy. I jumped into her car and she tore off at an insane rate of speed. We drew up short at a traffic light and she said, "Oh my god, is that Rob (our boss) in that car?" Well, believe me girls, in a Beetle there is only one way to "go down" and I put my face in her lap so fast I didn't have a chance to breathe. Then the hysteria retuned and we didn't stop laughing for weeks after that. She had to stop in my driveway, as I had the remote for the garage door in my car, and I had to get out of the car in full drag (and, god, I hope no one has a problem with that term) and walk her up the steps to my house in broad daylight. I am lucky that after all these years she is still a close friend. That's my story. Love, Carolyn

[CindyT]

One of my funnest experiences was just about a month ago when I was traveling out of town. Before I left I shaved my face very close, packed many of my clothes and took the stuff that I planned to wear first and packed them all into a small duffel bag. This included my short blonde wig, 36C bra, my size 6 breastforms with the large nipples, pink thong panties, jordache stretch capis's, a white tank top, white girls tennies and finally my purse with makeup.
I stopped at a wayside/rest stop about 60 miles from home, no one else was there, so I grabbed my bag out of the trunk, and strolled into the "Ladies Room" took about 5 minutes and "Cindy" came OUT! There was no mirror in there so I left my eye makeup off and just put my girls sunglasses on. I got back in the car and drove the rest of the trip as "Cindy", stopping here and there to tweak my makeup in the cars visor mirror.
First time I ever drove in full dress, putting the shoulder belt on around these breasts was a learning experience!

Also I posted my ultimate best experience in a different thread so heres the link to that one. Hope this works...

http://www.crossdressers.com/forums/...5425#post15425



Cindy

[Pamela girl]

Well I had to spend some time in a motel over the weekend one time and got all dressed up for hours then I was hungry so I changed back to my guy clothes and went to Burger king. When I gave the girl behind the counter my money I realized I had forgotton to take the nail polish off! It was pink so it didn't stand out real bad but it sure made my heart stop. If she noticed she didn't act like it but then I had to look and see who was looking at me and sure enough there were a couple looking at me like I was crazy.

[Miss Sherry]

When I was just starting out, and still very much "in the closet", I spent one night all dressed. Later that night I decided I needed a snack, so hastily took off the dress, etc, put on my boy clothes, and headed on foot for the nearest 7-11. It was very late, and not many patrons. When I was paying for the chips, I noticed the clerk looking at me rather funny, but shrugged it off and went home. It wasn't until later that I looked in a mirror and realized I hadn't removed any of my makeup ... lipstick, mascara, liner.

No wonder the funny look from the clerk!

Sherry

[Youthanasia]

A few weeks ago. A couple friends of mine and myself decided to go to Corvallis to go mess around. And I used it as the perfect time to go out for the first time en femme. And it was a blast. Just for the look that a little kid shot me at a gas station was priceless.

[Natasha Anne]

I was stopped by the police for running a Stop street. They asked me for my drivers license and then told me I had to show them mine, not my husbands. I eventually had to lift up part of my wig to convince them, and then they asked me to wait so the others could come look. It was all in good spirit and very funny. I didn't feel discriminated against at all.

[Alayna]

My "funnest" time was more of the indoors type. My (now ex) girlfriend and I had just had sex (both with panties ) and she was in the shower. I put on a red satin tap-pant and cami set I had bought when the two of us went to Target. I was standing just outside the shower talking to her and at some point leaned in and kissed her, getting a little water on my cami. Before long we were making love in the shower - I was totally aroused by the wet satin (so was she, though she probably wouldn't have admitted it!) That was "fun" to say the least!

As for "funny" mine was kinda like yours, Carolyn (not nearly as heart-pounding though!!) A friend had mentioned putting makeup on me once, and one night we decided to do it. Well, her complexion is totally different from mine, so I looked more like a drag queen ghost than a girl (no clothes, just makeup). Just after she'd finished, there was a knock at the door. It was like 4 of her guy friends (all over-macho, the type who would play football for no other reason than that it's manly) and she couldn't get them to leave! I was in her bathroom for 2 hours listening to her half-heartedly join their conversation while coming up with one lame excuse after another as to why they needed to leave. The next day though, apparantly she told them that she had a friend over while they were there and that he was getting ready for a drag party. I'm sure they bought that, cause people planning for a party always stay in the bathroom, silent, for 2 straight hours

[samanthajay]

my funesst time is when i was over at my best girlfreinds house. she new i like to cd here and there and then all of the sudden she had the urge to see me dress. "ill do your makeup jay come on." well i was a little nervous because a male freind was there and she just got done braiding his long hair(god how i wish i had his). she gave me a little maroune sparkaly top and strechy pants. then she did my make up . "damn jay you are a cute girl" i blushed. she tried to spike my hair but that was a nogo. then my gg called. she said that she was glad i was having fun and she wishes she was there.