Crossdress Stories

Crossdress Stories
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The Choice of Dress – My Crossdressing Story

I had just finished washing the dishes, when a knock on the front door. So, dried my hands, and opened it. Not thinking, I was still wearing a floral print apron, with ruffles around the edge.
Oh Miss Lewis, how can I help you, I asked?
Is your mom at home sweetie?, smiling at my apron.
No, mom has just gone with my sister, to town, on a girlie shopping spree.

So you have not gone with them, I see.
No, I just stayed to tidy-up, before they return this evening.
Well I must say, you are a very good one, aren’t you?
Thank you, but can I help you, Miss Lewis.
Well, as you can see, I have a mail order catalog here, and I am in a dilemma, which dress to choose, for a party, with the women, of the village group, next weekend.
No, wait, it maybe too late, by then, if you have not ordered the dress, and the day be next weekend. I can help you, to make up your mind, Miss Lewis.

Well, do you know anything about dresses, sweetie?
Well enough to choose for my mom and sister on times, as they also, ask my advice, as mom and sis, say, I have a good taste in women’s clothes.
Oh very well, I trust you, her now handing me the catalog.
Please come in and make yourself at home. Would you like a tea, coffee or wine?
Well thank you my girl, she answered, a wine please.
That is twice now, Miss Lewis has referred to me in the female gender. Oh, well she must be teasing, me, with this apron on.
Would you like something to eat, with it?
Oh sweetie, you’re spoiling me. I wish you were living with me, or visit occasionally, and you would do well, as my maid. Have you a chocolate bar sweetie?

Yes, I shall take wine with you, if you not mind, and a bar each.
You, addressing me as a young lady, and a girl.
Oh, please forgive me, but you with that pretty girl’s apron on, I just had to.
No, please, don’t. I like it on you, it suits you, with that blue top and those shorts, but tell me Graham. You are aware that everything on you, I have seen are ladies’ wear.
Yes, you are very observant Miss Lewis.
Can I ask you the reason why sweetie?
Well, when I am here, I like to dress up.
You mean, your mom and sister are quite oblivious to it.
oh no, on the contrary, they both know, and not only permit it, but encourage me to dress up.
My, this is so hot and I have read on this, but never have encountered a cross dresser before now. Well, it’s your home and your business, let me show you the two dresses.
She then turns to the catalog and shows me photos of dresses. Miss Lewis, pointed to both, but I was not fussed on either.
If you wish to wear either, then this one I would choose, but if you like my opinion, this dress here, I pointed to, on the other page.

Miss Lewis, smiling at me, saying, I bet it would look good on you, shall I order it for you, my girl?
No, no, I cannot accept that Miss Lewis, I would pay for it myself. I shall order both dresses, one for me and this one you like, for you.
Now no more said, in a commanding tone, telling me. Well let me, do some work for you, and I will feel much better for it. oh, alright, if you persist.
You, are aware, that I am a seamstress.
Well, if you make dresses, why buy this one.
Occasionally sweetie, I too like to buy a pretty dress, for myself.
I understand, but how can I help you?
I need you, to model some dresses for me, just to sew the hem of each dress and see how it looks on the woman, that has asked me to make it for her.
Oh, on times, the woman, who wishes the dress, just has no time to visit, for that, but you my dear, are about the size and build of the women, that be my customers. It’s only a dress Graham. I am not asking you, to put your hand in the fire.
We ended up, drinking the whole bottle of wine, between us.

Now shall I open another bottle Miss Lewis, as we now had the taste for it, and it were a hot summers’ day.
Oh my, you are a very naughty girl, aren’t you, trying to get me drunk, to take me to your bed, and have your wicked way with me, as her hand rubbed up my thigh. My you are very pretty Graham, for a boy. It’s a real shame, you were not born a girl.
Tell me Graham, are you wearing knickers?
The wine now, hitting us both and making us tipsy.
Yes MA-AM, as now my voice were high, and excited.
I want to see your knickers, to see what color they are.
Yes, but still want to see them girl.
Take everything off, show me your girl’s knickers. NOW GIRL!!
I thought best to do it, as she would rip all my clothes off.
Do it like a strip-tease, your flats, ( shoes ) shorts, top, and now mm, lovely pink knickers, as she grabbed me, and threw me over her lap, as I were only like 5 foot three inches, and her a buxom woman, with strength.
I am going to pull your pink girl’s knickers down, so I can spank you, and oh my we have a little wriggler, as I attempted to liberate myself, from her grip.

To no avail girl, you are going anywhere, until you have had a very severe bottom warming.
No please Miss, I beg you, as she ripped my knickers down.
My what a cute girl’s bum you have, very nice indeed, and SLAP, SLAP, SLAP.
I cried out, with her calling me a very horn-y naughty girl.
Once it were over, Miss Lewis, pulled them right off me, and stood me naked there.
Gripping my wrists, so not to cover my genital-ia, she told me, surely your not shy or embarrassed girl, we are all girls here.
Now sweetie, I need the bathroom, after all that wine, so you are accompanying me, and if I am right, you too need to pee. Once in the bathroom, told me to stand with hands on my head, and watch her. T
Then dropping her knickers to her heels, kicked them off, and ordered me to don them. My you look good in my knickers, which were a lemon yellow color.

I want you to wear them, when you arrive for the dress fitting.
Now girl, go and pee, and you had better sit.
That’s my girl, her smiling, and we washed our hands, then she gripped my wrist and nigh-on dragged me to my bedroom.
Good, because today, I am going to deflower you, of your innocence.
Miss Lewis threw me on the bed, and shut the bedroom door. Well, no need to continue, as we all know what happened to Graham, in there.
THE END
Written by Miss Jane Wyn Jones.
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I started crossdressing at a young age. A movie I saw once about a boy who was dressed as a girl by his mother got me very curious about dressing up. One time, I secretly got dressed in one of my mother’s dress when I was 12 years old. I simply loved the sensation and my desire to feel & look feminine grew with time.
I didn’t have much options back then to dress up. I could dress up very little because most of times, my parents would be home too. I only got to wear what I could find in the laundry most of the times. Sometimes, mom would have her recent worn clothes hanging in her bedroom and if no one was around, I would sneak in and put them on. It was such a rush for me.
One day, I was alone in the house. My parents had went to a party the night before and both of them were off to work that day. I had a holiday break after completing my school exam. I went into my parent’s bedroom to find if there was any mom’s clothes I could try on.

The dress that my mom wore the night before was lying on the bed. It immediately caught my eyes. It was a burgundy bodycon dress with a cut on the front side. I also found her bra, pantyhose and heels lying in one corner of the room. It was already making me tingle with excitement just thinking about putting them on .
I undressed myself and put on the bra first. It was a bit bigger for my size but it felt great. I could feel the bra’s strap around my back. Then I filled the bra with socks and adjusted the shape to make it look more round.
It was then time to put on the dress. It had a zip in the back. I unzipped it and then slowly put it on. Slowly got my body nicely inside the dress and zipped it from behind. It was a perfect fit. Instantly, I felt so feminine and beautiful.
Then, I got the pantyhose. I had never worn them before but always wanted to wear one. This was my best chance. So, slowly I put them on. I struggled to get it on because the alignment always got wrong. With quite a bit of effort, I finally got the pantyhose on. It was an intense feeling that I had never experienced before. I completely fell in love with how it felt on my legs. Lastly, I put on my mom’s heels and my feet could fit in them. It felt amazing.

I walked around the room in my new avatar and couldn’t stop staring at the mirror. I really felt like a girl. It was so nice to walk around in that attire. Then I saw my mom’s makeup kit on the table and from it picked a nail polish that matched the dress color. I was enjoying every bit of it. I started applying the nail polish on my nails. I was pretty bad at it. Just as I was finishing to apply the nail polish, I heard our main gate opening in the front. Someone was home early. I panicked and rushed to place everything back to where they were. I started to undress, I took off the shoes and placed them back.
Then, I tried taking off the dress, but I couldn’t get the zipper back down . I had maybe a couple of minutes before my dad or mom saw me and I was really close but I just couldn’t do it . I was mortified , my heart was pounding , I could feel my face was becoming bright red and I was sweating heavily.
I knew I couldn’t use too much force, otherwise the zipper would rip off. It was just stuck somehow and my only choice now was to run back to my room. Just as I turned to the door, it flung open and I saw my mom. As soon as she saw me, her face looked completely shocked and I had a very big fright that I almost screamed.
Immediately she asked me what was I doing wearing her clothes. My face became so red and I couldn’t utter any words. She noticed how embarrassed I was feeling and tried to calm me down. She spoke gently and told me to take off the dress. I told her the zipper was stuck. She turned me around and unzipped the dress. As she was getting the zipper back down, she saw I was also wearing her bra.

She laughed and said ” No, not my bra too. Why did you wanted to get dressed like this dear?”
I said I was really sorry and I didn’t know why I wanted to but I just felt like trying. I wasn’t a kid anymore and that made me feel more embarrassed. My mom then asked me how long I have been dressing up in her clothes and I lied saying it was my first time. The good thing was she wasn’t very angry and tried to be understanding. As soon as the zipper was down, I rushed to my room to take of the dress and pantyhose.
I returned the clothes to my mom and she said if I wanted to talk about it. I said I was sorry and just wanted to know how it felt to wear a dress. She agreed to not tell dad and after that moment I made sure to never get caught like that. My mom didn’t asked me about it again and I think I feel more comfortable like that.
I so wished I had dressed more as a wittle girl! I so wanted to be a sweet young lady for Mommie, and be her best daughter! I wuv being in dwesses and skirts, wif my wittle panties and bra under them, and to pway wif wittle bois. One day I weally want to have a wittle boi want to marry me and make me his wife. I would be ever so sweet to him. Oh, such are the way I feel these days. I so want to be his woman!
Miss Roxanne Lanyon
My parents divorced when I was 12. I started to dress up to and feel like the “woman” of the house, not the “man”. One night my mom was out on a date, so I dressed in my mom’s bra, panties, pantyhose, dress, heels, pearls and full makeup! It was so freeing. But, when she came home early, I was caught red handed. My mom was shocked and asked how long had I been doing this? I panicked and said this was my only time. A total lie. The next morning we had a very brief talk and she wrote the event off to the divorce as a one off. I’ve been dressing ever since!
I started cross When my mother asked me to wear a sweater suit to match the hem of her coat with the skirt. At 12, we were both 5’6”. I resisted and gave in. She tried just the skirt and the coat. She was not satisfied and added her girdle, slip, skirt, bra and sweater. The skirt and sweater were cashmere. I felt the soft texture of the sweater, the smell of my mother and her perfume and I was hooked. By the end of the afternoon she added stalkings and had me wearing two more sweater outfits with the camel hair coat. My heart pounded and I had a restrained woody in her girdle. After that experience I cross dressed on the sly when ever I had the chance for a year. I wanted to be close to my mother and I felt embraced in her soft cloths. A year later mom caught me in here cashmere suit. Mom was not surprised or angry. We talked and I admitted my strong feeling for her in her attire. Mom had me remove her cloths and had me bath in a scented bath and shave my whole body down. She had me dress again and every inch of my body felt wonderful. Than she applied make up and a wig with matching style and color to her own. Mom was turned on. I was turned on and I spent my whole Easter vacation made over in my mother’s image. We spent many weekends and whole summer together as girlfriends. To this day, I still crossdress behind closed doors.
That’s terrific. I wish sometimes something like that had happened to me.
Charming story … and I love the picture! You have great legs!
good story’s — there is not a thing I like more than dressing as a girl , then go to then shopping
good story’s — there is not a thing I like more than dressing as a girl , then go to then shopping
as i am there i will buy new bra an panty’s of different color’s
im 51 and married my wife knows im fem and she buys my panties and she pays to get my hair fem permed and curled and rollerset and have curlers put in my hair looking for another into girly clothes and a fem hair perm
I enjoyed reading your story. I wonder what my life would have turned out to be like if I had been caught by my parents and confessed that I enjoyed wearing femme underclothing.
By now I am a mature crossdresser. I think I want to graduate and become a real trannie girl, and wear feminine clothes 44/7! I simply adore being feminie, and would even love to go out on a date as Roxanne, with a sweet, knowing man! Oh my! I just know I could be a really loving girl for a nice, caring man, someday!
Miss Roxanne Lanyon
That’s a beautiful story.when I was small,our neighbor lady watched me after school every week day.For some reason it was important for her to dress me like a girl and demand I act as if I was her daughter every day. I did love her, even though she was very strict and controlling, the feminine clothes she dressed me in always made me feel peace and joy. I was with her nursery school thru 3rd grade. Will never forget her….
i was 13 and a half when i started to dress, my mom worked as a nurse then they wore all white bras slips stockings and shoes, her bra would always fall so tried kid sis omg it felt great, from then on i was hooked. one day i got fully dressed in kid sis cloths, black bra, panties,white half slip lime green skirt,light pink blouse red tights white mary janes and did my chores, came up from the basement and was confronted my mom. all she said i was dressed all wrong and come with her to sister room where she re dressed me and re named me from then on i had to dress
lovely story. I have loved to dress in ladies clothes always made me feel so feminine.xx
there is not a thing better than to dress as a girl
love to dress up as a sweet girl then go to town an do sum shopping
Nice! My mother caught me rummaging through her lingerie drawer when I was young less than 10, she walked in when I thought she was going to be out for the afternoon and caught me in the bottom half of her canary yellow two-piece baby doll. Instead of freaking out took a cut off and slowly slipped the top half of my shoulders. She started to brush my hair and told me how adorable I was. She nurtured me for many years and I trust in front of her from the time I came home from school to the next morning when I left we shared many things and she taught me how to be a good young girl, and when I was older and she was older I would still trust for her and black bras and panties and more mature see through tops and short shorts she always got a kick of how cute and sexy I looked!
Well, her am I again! I am still not yet married, but am still looking aroun! I have had a few men interested, but none into marriage yet. Some day, I hope! I am a mature woman now, but I think I am still cute! I am learning how to please a man, and love to practice on him! One day there will be an ivory lace gown in my life, and I know I will be the happiest woman in the world! with, I hope, the happiest man on my arm!
Miss Roxanne Lanyon
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