I had such a strong desire, to dress up like a woman and to go out in the streets against my shy personality.
“Well….. it is a good idea. Everybody goes out dressed like an idiot during carnival, so why can’t I go out dressed like a woman” I said.
“Let’s go to do some shopping, my girlfriend will help you to buy clothes and all stuff to transform you”. Mark said, smiling.
So we took the car, and after picking up his girlfriend from her place, we all went to the centre to have a walk and look at the shop windows. For the wig there wasn’t any problem, at first try we hit the spot and found one with straight red hair long down to my elbows.
As for the shoes we had a little trouble, shoe shops usually doesn’t stock women’s shoes above 39 sizes, and my feet are 43, so after trying in some shops we decided to directly ask the clerk, who suggested to give it a try in a shoe shop specialized for transgender, which wasn’t too far away.
As soon as we entered we knew that we were in the right place, I tried some shoes that were really nice. It was really strange for me to wear in women’s shoes in public, but after a couple of minute of embarrassment, I got used to it, especially when Kate, my friend’s girlfriend, told me that I was looking for something to wear to the next carnival, I relaxed a bit and enjoyed the feeling of walking In high heels. In the end, I decided to buy a pair of classic black shoes with 10 cm pin heels.
The next step was a boutique for a dress, in that case, we had to look around a little longer, because we couldn’t find anything that suited me well, the clothes that suited me, were elegant dresses with a jacket and long until knees, but they didn’t go well with the shoes, so again in the street to look for something else.
In a small store halfway on the road, I saw a black leather miniskirt, I loved it at first sight, and told Kate. She agreed with me, that skirt would look fantastic with my body, and also with the shoes, now it was coming together, I could dress up, yes, like a woman, but more specific… like a whore.
My eyes sparkled with excitement and before she could say something else I was already in the shop. When they reached me, I had already told the clerk my intention to dress like a whore the next carnival, and I liked the skirt in the window.
The girl measured my size and after some minute came back with the skirt, a sexy black transparent shirt without sleeves, and a black leather jacket, that complemented the skirt perfectly.
“Here you are!” The clerk smiled as she laid everything on the counter.
We analyzed every item of clothing and we were amazed about how that girl understood exactly what I was looking for. I entered the dressing room and dressed, then Kate gave me the shoes, after putting them on too, I looked in the mirror… The clothes suited me perfectly, erasing from the mirror the vision that normally stares back at me, the face of a man. Now I was looking at the physic of a real girl. Kate entered the dressing room too and seemed really satisfied.
She turned to me and said, “Ok, back in your clothes, we still need lingerie and accessories”.
So after a short while, we were again in the streets, but this time, we didn’t stop to look at any window, we went directly towards a shop that Kate already knew. It was a shop specialized in lingerie where she used to work until some months before.
Me and Mark (under Kate’s order) remained outside smoking a cigarette, and she went in to do shopping.
After that last effort, we were almost ready to go back home, we just needed a bag, a couple of necklace’s, a ring and earrings, luckily on my right ears I already had holes since my youth “trendy” period.
For the bag there were no big problems, Kate had enough spare bags at home and according to her memory, there were a couple that would match my chosen attire, for Jewellery we spent over an hour looking in a shop before deciding what to buy.
I bought a set made of a white gold, a necklace with a teardrop-shaped piece of yellow gold and a small pearl in the centre of the drop, identical earrings, a simple bracelet made with a white gold chain, and two rings, one was a white gold band with small emeralds, and the other a simple white gold circle.
We had finished our shopping, we realized it was already eight o’clock in the evening and decided to have a pizza at Kate’s place.
After we had our dinner we were ready to try my transformation.
Mark took a seat on the sofa, to watch TV, while I and Kate went into her room. There she simply ordered me to undress, so I obeyed, remaining with only my underwear and socks. Kate took the lingerie out from the package and watched me.
“I SAID NAKED!!” she shouted, “It won’t be the first time I’ve seen a naked man”. She smiled and I removed everything.
First of all, she helped me shaving completely. All the hairs on my legs, arms, torso and back have been removed with shaving foam and razor.
Then she taught me how to wear lingerie correctly, especially stockings, it took a couple of attempts to get there, but with her help, I learned quite fast.
With black silk underwear on and my legs wrapped into the black stockings, I slipped into the skirt.
Then she gave me the black silky bra, helped me to put it on, and filled the cups with silicon enhancers.
“It looks like a 2nd measure,” she said, then gave me the shirt and I put it on.
The transformation was almost complete, she spent almost forty minutes to make me up with her lipstick, fake nails and polisher, and all the other things and at the end, I put on jewellery, wig, shoes and jacket…
Then I was ready to look in the mirror, Kate called Mark to see me… and we were all really impressed… I was looking at a girl, a really cute girl.
After congratulating with Kate for her good work, I dressed back in my male clothes and went back home.
Carnival was approaching, two weeks passed since that shopping day. More or less.
Every day I dressed up in my apartment and learned to put on make up by myself, every time I was more satisfied than the previous.
Once watching myself in the mirror I asked myself if I was gay, enjoying that behaviour of mine. So I thought for a while. I realized I like to dress like a woman, would I like to make love like them, just the idea to get a cock in my mouth, or in my ass, to be soaked with sperm all over my body, simply disgusted me, so… of course I was not normal, but not really gay…
I was still wondering about my “nature” when I was looking at myself in the mirror, and Kate and Mark arrived to bring take me to the Carnival party at friend’s home.
In the car, I asked them the same question, but they were more interested in speculating about who might be at the party, so I gave up.
Party was more or less good, surprisingly I wasn’t shy at all, well everybody, as planned, was masked, and there were others dressed like a woman, but everybody was impressed by me, I was showered with compliments for my “costume”.
During the party Kate called me, she wanted to tell me something but in the room, the music was too loud to talk freely, so, we decided to look for a better place.
We walked down along a corridor, and as a game, she took my hand and when we met people, smiling, she said that we were going in the bathroom to fix the makeup, at the end of the corridor there was the door to the garden, and after crossing it, we realized that that garden was bigger than expected, it was more like a small park.
“How are you?” She asked as soon as we were outside.
“Fine thanks, I am really relaxed and well also a bit excited”.
“Oh… my… why excited?” She said looking surprised.
“Well, you know… this situation, being dressed as a woman, in public…” I was talking freely, ignoring the fact I was talking with a pretty girl, by the way, she was a friend, and my best friend’s girlfriend, so I didn’t have any strange ideas. “I am so hard all the time, while dressed like this”.
“Wow,” she said and put her hand over my pubis feeling it and caressing through the skirt. “You are right, it is like a rock”.
There I was really embraced, and she noticed it, smiling with the look that only a real woman would have, then she kissed me on the lips, and even if I was surprised, I held her in my arms, replying to her kiss.
Kate rubbed her hips over mine feeling my penis and enjoying it. Then stopped kissing me, remaining a couple of minutes looking in my eyes. On her lips, there was a smile painted on in red.
Then, she took my hand and led me into the garden where there was a big oak tree, she didn’t say a word and unzipped my skirt letting it slip down on the ground, she turned her back to me, and I understood immediately her desire, so I unzipped her White snow gown and she removed it leaving it falling at her feet.
Under the gown she was wearing the same lingerie she bought for me. Black bra and underwear made of silk and black stockings and garters, then we embraced again and started kissing, but this time with more passion, our tongues were dancing in each other mouths, our hands caressed each other bodies, and in few minutes we laid on the grass under the oak. From the house, nobody could see us, thanks to the tree.
Laid on the ground we kept kissing and whispering our desire. Our legs wrapped in the nylon stockings were entangled. Kate brought her hand on my penis and released it from the panties.
I untied her bra and removed it, leaving it next to us, and started caressing her breasts, using my fingers to play with her nipples, she was excited like me and moving aside her underwear, sit on me, lowering herself on my stiffness.
I felt her wet and warm swallowing my sex slowly, inch by inch. Kate took my hands with hers, tilted her back backwards and went down slowly and completely, enjoying, every millimetre entering inside her.
When I was swollen completely into Kate’s vagina, I pulled her hands, and she laid over me. We kissed while she moved her hips slowly.
Then she lent back against my legs and sitting on my pubis she started to move up and down caressing my folded legs. She was enjoying it but looked at me, and realized that I was not really comfortable being so passive, so she stood and put her hands on the oak tree offering me her back and moving her ass.
I stood up and laid on my knees between her legs, after removing both of our underwear, then I started licking her wet pussy and going up until her asshole, with my fingers I penetrated both her holes, listening to her love sounds coming out from the mouth mixed with an invitation to make her happy.
So I stood and easer myself into her welcoming, hot, wet pussy from behind, I reached around with my hands and squeezed her breasts, pulling her towards me, while moving my hips sinking my dick deep inside her and then again out.
Kate’s breath became heavy, her desire was stronger, she started asking for more, faster, harder, and I obeyed, raising the rhythm of the penetration until her body began to shake with her climax, I was also close to coming, but I asked my strength to resist a little more.
When Kate recovered a bit of her composure she turned toward me and went down on her knees. Taking my cock into her mouth she teased me to cum and helped me to reach the orgasm while masturbating me.
When I came, she swallowed, and with the mouth still full of the white nectar she pulled me on the ground again and we kissed again exchanging sharing my cum in our mouths.
We laid together, locked in an embrace on the floor, just relaxing.
A couple of days later Kate came to visit me, she told me that Mark had finished it with her, she told me that if Mark hadn’t made the first move to end it, she was going to do the same.
I was still realizing that they broke up, and maybe I could have a chance to start something with her… but she anticipated me, answering the question I asked her and Mark in the car, with another question.
She looked me deep in the eyes, thinking hard and said, “Do you still have doubts about your sexual identity?”
“No” was my answer “I may have strange desires liking to dress up, but… I still like women… and… well a woman in particular now occupies my thoughts.”
Kate opened her hands and I embraced her.
“Good, because I like strange desires, and I need a man who knows what he want’s.” She said smiling, her eyes were sparkling with anticipation and I knew what she was thinking.
We kissed, and I lead her to the bedroom.