My First Time.

We all had our ‘first time’ dressing. For some of us it was fun, for others it was shameful and humiliating. Poor Julie – have you read her story? It’s worth join our Premium Members group just for her story. You can get a glimpse of it here:

I’ve decided it might be helpful to allow my members to tell their stories of their first time dressing up. So, all you need to do is go to my site, register, and then post your story of the very first time you dressed up. You may find that others have had much the same experience as you.

Remember, this is about having fun. Tell us what your journey into the world of dressing entailed. Tell us how you felt about it, and if you like how you feel about it now.

All you need to do is Register, (if you haven’t already) and then use the comments section below to tell your story.


13 Replies to “My First Time.”

  1. Hello Fiona,

    my first time really was two years ago…
    I had been already and alone wearing girly clothes, enjoying the thrill of wearing panties, stockings, heels, and dress or skirts…
    But the real first time for me was when i had the urge to meet a man and being Lola…
    We texted and called each other, and he said he would welcome me at his house…
    I was so nervous, anxious… But i took my little bag, after carefully choosing my clothes.
    A jean short skirt, a white half transparent top, leaving my shoulders naked, a nice black lace shorty and black garterbelt with stockings. White heels.
    I got to his home, he opened the door and my heart was beating. I asked him where i could prepare myself, and i went to his bathroom…
    The whole process of quitting my “man” clothes, and slowly and sensually becoming Lola was so much a thrill already… I was aroused… Slight make up, eyeliner, mascara, and liptstick…
    Then i got into his living room…
    Walking nicely and sensually up on my heels, my hip bouncing gently while walking toward him…
    I will never ever forget his eyes on me, as i was scared to be ridiculous or awkward…. He was looking at me with the most intense lust i had ever seen in a man’s eyes.
    I felt achieved. I saw I was making him totally excited, and the massive bulge in his pants was quite obvious 🙂
    What happened next for some hours was the most intense experience of my life, as Lola was a virgin so far (well, as Lola) and i knew at every instant and then after this was me, this was right, and this was what I was craving for.

    I am married, my wife doesn’t know about my femme side, but I don’t care since i know what i want and who i want to be.
    This was my first time.


    1. Hello,
      Très très beau récit Lola. J’aurais tant aimé être à la place de cet homme… cela a du être un moment intense et magique pour vous 2

  2. I was about 5or 6 years old my mom had some of her lady friends over for drinks one day and started dress me up in girls things – a bra and panties, a nice sun dress – and then put make up on me. They did my hair all up and I had to walk to all her friends getting a kiss from each of them.

  3. My first time I was 12. I tried a pair of my cousins underwear on. I wish I still had them. I was at her house. We played with eachother a lot. We got naked with eachother and felt each other for hours, played together fingered and stroked each other. It was great! We still love eachother! Occasionally we still get together. It’s fun.

  4. I was 11 the first time I tried on my mom’s clothes. I was going from the bathroom into the hallway and the door to her bedroom with ajar, and I could see she had a bra and a slip laid out on her bed. I felt a little tingle and it came in my mind to try on the bra and the slip to see how they would feel. I liked what I felt and what I saw in the mirror. I found her lingerie drawer and pulled out some stockings to stuff into the bra. I felt the shape of my “breasts”. I was hooked from there. Two or three times a week after school before my mom would get home from work, I went into her bedroom, opened her lingerie drawer and picked out what I would wear. I got so aroused! I discovered that wearing a pair of panties under her slip allowed me to lie down on the bed and rub the panties against the slip material to get an incredible erection and release. I also used pictures of women and girls in lingerie from catalogs that my mom kept to further my excitement. I sometimes tried to stop, but I couldn’t for more than a week or so. I repeated this often until I went away to college and lived with other guys in a dorm room. Later on, after I got married, the urge came back, and that’s where I am now.

    1. My story is pretty similar. A little exploration of moms satin slips and panties, years of suppression, occasional wearing of spouses stuff under man clothes and now as a senior, a deeper exploration including some femme hypnosis, finding a few friends in an online friendfinder site . One of these hosts parties that includes a makeup pro who did me the first time. It was pretty amazing.

      Now your program is guiding me toward next steps that is leading me to some “dates” with others I’ve found . I’ve bought stuff and am ready to play! Life’s to short !

      I hope I know what I’m getting myself into!

  5. I was 10 we just got home from the laundromat and I had started putting my stuff away and found a pair of black panties in my stuff. I knew from the style they were not my mom’s and I got curious and tried them on. It was like a switch was flipped in my head and I knew that this was the first of many more times to come.

  6. I had been playing around in my sisters stuff for quite a while and she knew, so when I was 11 she dressed me up for halloween from head to toe. It was a short pink dress with little strawberries on it with nylons, bra. panties with ruffles on the bum, high heels and makeup, the works. That was when I knew I was Heather. I had such a great day and night and when I went home I pretended to fall asleep all dressed up so I could spend the night as the real me. My sister was great, she talked to me about it and started buying me stuff and keeping it in a special place in her closet, so when I went to visit we would have girls night.

  7. My first Time when i’ m 13 years old, i try my mother’ s green satin panties, the sensation On my skin Are very horny and beatiful !! And Everyday i put it with pantyhose and high heels . It’ s very beautyfull and i love wear feminine lingerie and clothes !!

  8. Fiona … My first time.
    I was 14 yrs old and had two older sisters and I remember I would wear their tight skirts and tops and always involved panty hose.

    I would always employ some type of bondage and red lipstick. Things really haven’t changed 30 years later except for the fact I have an entire closet filled with my own clothes.

  9. My first time I was a young boy in the year 2002. Age 11. It wasn’t my first feminine experience as I’d had a neighborhood friend as a kindergartener and she loved to play barbies and the like. And it was then I started wishing to be a girl. But at age 11 I was a 5th grader. The school had just held a womanless pageant that I was too “proud and macho” to enter. As I watched it, I felt deep regret not volunteering to represent my class. I went into a storage closet to find something for a teacher and there it was. A cheerleader uniform just there in a box. I looked around and stuffed it under my shirt. I snuck it to my locker and backpack. After smuggling my treasure home I hid away in my room and locked the door. I stripped and put on the tight form fitting dress. It was designed to fit a girl and I was small and skinny for a boy (what I wouldn’t give to be small and skinny now) so it gave me the appearance of a feminine body (for an 11 year old, I just remember having a slight hourglass). I danced and twirled for hours on end, almost daily. It was wonderfully addicting. I felt pretty for the first time and I was hooked for life. I kept that dress until I hit a growth spurt later that year and I returned it to the school when it didn’t fit anymore.

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