Does anyone have a good crossdressing story?

Question

It could be funny or serious and at any time in your life. Whether it is at college or at home.

Answer 1

I have quite a few good cross-dressing stories, but my favorite is about the time my apartment manager was telling me how she dressed as guy friend of hers like Erica Kane the past Halloween. I asked her how could she make a guy look like Erica & said I didn't believe it. Then she said she could even make me look like Erica, I said yeah right, I doubt it. She asked if I'd let her try & I said sure, why not, then I bet her she couldn't do it. I lost the bet and she did make me look just like Erica Kane & that evening I was playing pool dressed as Erica Kane. When we went home to her place I told her that I loved to cross-dress, but had not dressed in a while & after she told me the story about her friend, I thought I could talk myself into letting her dress me like a girl. That was just the first time she dressed me up over the next year, I sure missed her when she was transfered, but we had fun.

Answer 2

New Crossdressing Stories

Answer 3

I've not gone out in public yet, so I don't have any really embarrassing moments. My most embarrassing moments are almost being caught a few times. I'd think I have the house to myself, only for someone to come home early which leads to a mad dash for my room before I get seen. I've also had a couple of occasions where I've been shopping and the sales staff have informed me that the men's department is upstairs. That doesn't really bother me though as I just say that I'm buying a gift for my girlfriend.

Answer 4

Woman at work made it plain she'd like to go out. I wasn't dating so we went to happy hour at the local pub. Got tipsy and I said I was uncomfortable with the idea of her driving home ... "Let's walk over to my place and have a coffee." We did. While I was grinding beans she went to the (HA!) ladies room. I had a big one bedroom and the bathroom is around the corner and down a carpeted hall. Didn't hear anything for a bit and thought she was taking her time. When she came back and sat down, she had a weird look on her face. I ****** my head and asked what was on her mind. She shrugged, shook her head and said, "Nothing." Halfway through the coffee, she said, "I did't know you had a GF." I instantly knew she had looked into my bedroom. I leave the door open (duh, I live alone) and you can see into the walk-in closet from the doorway. Almost my whole closet is filled with women's clothing ... dresses, skirts, blouses, shelves with bras, panties, etc. I've had enough heartache dealing with the result of trying to hide that part of my life and had made the decision to tell all at the beginning of a relationship regardless of the consequence. If it's going to be a prob ... better to know up front. I told her who the clothes belonged to. Best relationship I've had.

Answer 5

Once I was out for a walk on a nice summer evening wearing a really short skirt, heels and stuff, when a cop car pulled up beside me. I nearly passed out I was so scared. The cop asked me when I started to work "this side of the city", and before I could answer he got a call and had to go. He just said "It's your lucky day!" before he took off. It all happened so fast I didn't even have a chance to be insulted that he thought I was hooking lol.

Answer 6

I was working for the lady who trained me as a maid. She had a guest house at the sea side and I was helping her get it ready for the season. I was wearing a female cleaners uniform from Alexandra. Green dress, white apron with green pattern and a matching head scarf, stockings, nice court shoes with satin bows in the front. She did not tell me she had ordered a new fridge and she went shopping while I was cleaning one of the downstairs rooms. She left the front door unlocked and two guys arrived with the fridge. They gave me some very funny looks and I was very embarrassed That was just after I had started to dress as a maid if it was now I would not have bothered as I have since appeared in TV 3 times as a maid, been a maid at a wedding reception, cleaned front windows in full view of a busy street and signed for parcels all in full maid or cleaners uniform

Answer 7

I get the feeling all the time to crossdress. So 3 months a go I went out and bought some panties and hose's I rushed home to put on my new things i put my boy jeans back on and the panties and pantie hose felt really sexy with my jeans on. It felt so sexy and nobody knew I had panties on.

Answer 8

When I was sixteen my parents caught me dressed in my sister's clothes. My mother and stepfather came home early from a party to find me wearing a dress, hose, heels, made up, the works.

Now, strictly speaking, from my point of view, I wasn't crossdressing, as I thought of myself as a girl and from this POV, I was wearing clothes appropriate to my gender. They didn't agree; they say a boy in a dress.

I was lectured, and later beaten by my stepfather. At the end of the school year, I was sent to a "Christian therapy" counseling center to cure me of being gay. I wasn't, I wasn't even attracted to boys, but they either couldn't or didn't understand the difference, so off to gay counseling I went.

The therapy consisted of being told repeatedly that I'd be going to hell for being who I was, that God wanted me to be with girls. I told them I was attracted to girls, but it made no difference; they assumed I was lying.

It didn't cure me. It isn't possible to cure me, because having a female mind isn't a mental disorder; the defect was my body, not my mind. It did make me miserable, teach me to hate myself and left me depressed and in a near suicidal state of depression, convinced that God hated me and that I would never be able to go to heaven.

But I was still a girl inside, and still attracted to the clothes as an external confirmation of that.

Answer 9

I was in two plays at school and both times I was cast as a guy. Doesn't do much for a girl's self esteem!!

Answer 10

I like women in jeans. It creates them look more home town like and it generally does not appear to be they are trying too hard but if you are trying to get this guys attention, this might not exactly be what you want