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Crossdressing In Public : A Day Out Dressed as a Woman !

crossdressing in public for first timeI have been crossdressing since my teenage years. I was really fond of skirts and tights since I can remember. When I secretly wore my mother’s pantyhose for the first time, everything changed. I wanted to dress as a girl so badly. So, I started sneaking into the laundry room to try out my mom’s dresses, pantyhose, skirts. The more I dressed in her clothes, the more I wanted to become a girl. I used to fantasize a lot of getting transformed into a girl and living as a girl for the rest of my life.

My family is quite religious and that was the reason I never had the courage to tell my parents about my dressing urges. I knew they would never understand. So, I dressed in secret whenever I had a chance. I did have few really close encounter with my mom when I was dressed in her clothes.  But luckily, I never got caught red handed.

As I started college, I signed myself up for more sports activities to suppress my feminine side. I moved out and started living with a male friend. For a few years during college, I stopped dressing in women’s clothes. I would get the urge to dress up now and then but I resisted every time.

After college, I joined a software firm as an intern. There I met a beautiful girl ‘Janice’ and we started dating. After few months of seeing each other, we decided to move in together. It was nice living together and we were both earning good money at that time.

One afternoon, I was home a bit early from work and it was a hot day. So, I decided to take a shower and I went into the bathroom. As I was taking off my clothes, I noticed Janice’s panties lying on the floor. It was a pink lace panty with a cute bow in the front. I suddenly got this intense urge to put on the panties. I couldn’t resist it. I picked it up from the floor and slowly put it on. My body trembled with excitement. Everything came back to me. I remembered how much I loved wearing panties.

Since, I was home early that day, I knew I had some time on my own. I put on my robe, still wearing the panty and went to the bedroom. Then I opened my girlfriend’s closet and I could sense my heart beating faster. It was such a rush looking through Janice outfits, especially her panties and lingerie collection. After deciding what to wear for sometime, I finally took out a white padded bra and a  black bodycon dress to wear.

I closed all the curtain in the bedroom. I surely didn’t wanted any of my neighbors to catch any glimpse of me. Then I took of my robe and put on the bra first. It was a bit tight but I managed to put it on. I loved how the straps felt on my shoulder. The padding made it look like I naturally had tiny b00bies. I loved the feeling of the bra pressing against my skin. Then I put on the bodycon dress. I simply loved how figure hugging it was. My body looked so much better in a dress than in guy’s clothes.

I went in front of the mirror to check out how I looked. I blushed when I saw myself. I was so happy to see how cute I looked dressed as a girl. I must have spent hours just standing in-front of the mirror, posing and admiring myself. I loved every moment of it.

As it started getting dark outside, I realized I had lost track of time and needed to change back before Janice arrived home. So, I undressed myself, put everything back where they were and took a shower.  All the while, I just couldn’t stop wondering why I liked dressing as a girl so much and why I was attracted to girl’s clothes. Afterwards, I felt a bit shameful that I dressed in Janice’s clothes. I was confused whether or not I should tell Janice about what happened earlier.

When Janice arrived home, I was quite nervous. I couldn’t decide whether or not I should tell her that I wore her clothes and I has this urge sometimes to  dress as a girl. I knew that could put our whole relationship in a big mess. So, I decided to not tell her and didn’t dress for the next couple of weeks until one day Janice said she was going out of town for her cousin’s wedding for 3-4 days.

The thought of being along for a few days sparked a new excitement in me. I started having the urge to dress up again. This was certainly a great opportunity for me to live as a girl for few days. I decided that it was going to be the last time I dressed as a girl but I would enjoy it to the fullest. I began preparing for the special day. Janice was busy with her own thing with the wedding. So, I had more time to plan everything perfectly.

I figured online shopping would be the best way to buy everything I needed. I browsed through a lot of clothing shops online because Janice clothes were small for me to dress up. Many times I just lost track of time as there were so many choices when it came to shopping for girl’s clothes. After hours of looking around, I finally ordered a bra & panty set, a lace hair wig, high heels, two dresses,  sheer pantyhose, and even breastf0rms. All the items arrived within the next few days and I hid them in the garage. I was super excited for the moment to arrive when I could fully dress up from head to toe and transform myself into a beautiful woman.

Finally the day arrived, I dropped Janice at the airport, kissed her goodbye, and went back home. I was so excited to have the next few days all to myself. When I reached home, I went straight to the garage where I had hidden all of the things I brought and took them to the bedroom. First, I unwrapped everything; two dresses, a bra, panty, wig, heels, breastf0rms, and pantyhose; and laid them neatly on the bed. It was so much fun just doing that. Now time to get ready!

I decided to shave off my facial hair and also my legs. I wanted to have smooth legs like gorgeous models. I took a shower and shaved my face and legs. Then I put on moisturizer on my face and all over my body. Now, it was time to put on the bra and panty. My body was shaking with delight. I put on the bra & panty and instantly felt so feminine. I slipped on the breastf0rms into the bra’s cup and I was shocked how real they looked and felt. I couldn’t stop jiggling them. I was so glad that I brought them, it was really worth the experience. 

Next, I picked the pantyhose and put them on slowly. I was very careful because I didn’t wanted to rip them up because of my excitement. I managed to pull the pantyhose all the way up without any rip and did some final adjustment so that it looked nice and smooth. I loved how sexy my legs looked now and the sensation of wearing pantyhose on clean, shaved legs was amazing. I rubbed my legs together and it was divine.

Now, time to pick a dress. I had brought two dresses; one was a leopard print bodycon dress with a full sleeve black top attached and the other dress was a white floral knee length dress. I decided to go with the leopard print dress. I put on the dress and it was magical how it felt on my body. It was a bit short but I liked it. I twirled in front of the mirror to check how I looked from all the angles and I couldn’t help smiling looking at myself. My body was now completely feminized and I loved how feminine I looked and felt.

It was now time to put on the hair wig and some makeup to complete my transformation. The wig also came with a hair cap. I put on the hair cap first and then tried on the wig. I struggled a lot because I had never worn a hair wig before. It was harder than I had thought but after a few try I managed to put it on. I could already feel how much of a difference it made to simply put on a wig and having long hair.

When I looked into the mirror to make some final adjustments, I was blown away by how different I looked now. I didn’t look like a guy anymore, I looked like a WOMAN! I had no idea a wig could change my appearance so much. I was so happy to finally see the woman that was hiding inside me all these time. I felt beautiful, strong and confident! I couldn’t believe how strong the feminine energy was, radiating throughout my body at that moment. I stood in front of the mirror for a long time, looking at myself, admiring and accepting my new self. It took a while for everything to sink in. It felt so right, I felt so happy!

Moving on, now it was time to put on the heels. I had already tried it once  when it arrived, just to check the fit and it was a lovely fit. I sat down and slipped on the heels. Heels really added so much glam to my feet and legs, especially with pantyhose. I stood up, took a deep breathe and took the first few steps as a woman and it felt great! The whole experience of transforming myself into a woman was so much intense than I had imagined it to be. I was glad that I decided to dress up otherwise I would have never known how amazing it felt. I no longer felt like a guy, I felt like a beautiful woman!

I walked around in the bed room for few minutes, just to get the hang of walking in heels and also my new self. It was a lot of fun. Next, it was time to put on some makeup. I had watched a lot of makeup tutorials on YouTube to be ready for this moment and I was excited for this. I went to the Janice’s dressing table and took out her makeup kit. It had everything I needed and I didn’t want to put on too much makeup, just enough to minimize my male features.

I took some moisturizer first and as I was applying it on my face, hairs kept getting in the way. I realized this could be a problem for me to apply makeup properly. So, I looked around and saw a couple of Janice’s hair clips. I took one and used it to clip the hairs back. It was better now and I proceeded with the steps.

After moisturizing my face, I put on some foundation on my face, not too much, and gently tried blending it all over my face with a beauty blender. I had seen Janice do this a lot of time and it definitely helped me use the right amount of foundation. I could see how smooth and bright my face looked after applying foundation.

Next, I used some eyeliners to draw a nice line over my eyelids to make them look more feminine. Janice only had liquid eyeliners and it was quite tricky to use. I kept messing up, had to wipe the eyeliner with tissue papers and redo the foundation step again and again around the eyes. After quite a few tries, I managed to draw decent eyelines and I simply loved how my eyes looked so beautiful and feminine now.

Lastly, it was time to put on some lipstick. I couldn’t decided which color shade to use since Janice had such a big collection of lipsticks and lip gloss. After looking around, I went with a light shade pink lip gloss. I might have applied a bit too much but I liked how my lips looked so glossy and attractive.

Now that the makeover was complete, I was pretty happy with the outcome, especially because it was my first time wearing makeup. I felt like I did a decent job. I would have never believed that I could look so beautiful as a woman. It was a lovely experience to try makeup. I felt like I was glowing now!

I looked around in the dressing table and saw Janice’s jewelry box. I opened it and there were some cute necklaces, earrings, and some bracelets. I took out a necklace and I also noticed a cute clip-on earrings that I had seen Janice wear before. I put them on and I was quite happy with the look. It was amazing how accessories could add so much style even if there are just small pieces. Then, lastly I choose one of Janice’s perfume and sprayed it on myself. The scent made me feel so womanly and beautiful.

I felt like my transformation was complete now, I loved how I looked and I just felt amazing. As I was checking the drawer one last time to see if there was anything I missed, I noticed some press on nails on the drawer. I decided why not and applied them on my nails. I had seen Janice apply press on nails many times before so I had some ideas on how to put them on. After I was done, I loved how my nails looked, they looked so pretty.

I was all set now. I took off the hair clip and let the hair down. I liked how flowy the hair wig was and made some last adjustments. I stood up and walked towards the full length mirror we had in the bedroom. I couldn’t believe my own reflection and how gorgeous I looked as a woman. I could just stand there and look at myself for hours.

Then suddenly my stomach growled, I was so focused on getting ready that I completely forgot to eat something.  I looked at the watch and I was surprised to see that it had almost been 4 hours since I started getting ready! I didn’t want to lose track of time again, so I put on my watch just to remind myself.

I stepped out of the room to go to the kitchen but it felt so different, walking in my new attire. I was scared and excited at the same time. The sound of heels as I walked gave me so much pleasure and the realization of how it felt being a woman. The rush was unbelievable. I reached the kitchen and took out some leftover pizza from the refrigerator. Heated it up in microwave and grabbed myself a soda as well. I sat down and started eating. Even though I was very hungry, I decided to eat slowly, just like a lady would. I wanted to be bring out my feminine manners to the fullest.

Now that I was full, I had a lot of energy to do things. I thought about what to do next and decided to take some photos and videos. So, I went back to the bedroom, grabbed my phone and tripod, set it up, and started taking some pics and videos. As a guy, I didn’t really like taking pics of myself but now that I was dressed as a woman, I loved it. I really enjoyed modeling in front of the camera. It was so much fun. I just didn’t want to stop. When I checked the time, an hour had already passed.

I sat down to get some rest as my feet started feeling a little sore but I didn’t want to take off the heels. I started going through the pics and videos I had just taken. Most of them came out so good. Just then I got a call, it was Janice. I jumped up in fright! I got so nervous to pick it up but I knew I had too. I just prayed she wouldn’t ask to turn on the video.

With a deep breathe, I answered the call. As we talked, slowly all the excitement I had for the next few days vanished. Janice told me that she was coming back the next evening because there has been some emergency at work. I was so bumped. But I tried to reply as calmly as possible and said okay. We talked for a bit and she told me what was going on at the wedding but my mind was so distracted by the thought that I wouldn’t have more time for myself anymore.

After the call ended, I was really frustrated but I knew I had to make the best of the situation. After trying to think for a bit about what I should do next, a thought came to my mind. Why not go to the backyard and record myself there in the open. It would be a complete new experience for me. Just the thought of it gave me such a rush. My body shivered with excitement again. I figured I might make it a little more adventurous.

I took the tripod, my phone, and walked towards the backyard. Our backyard is a pretty private area and the neighbors can’t see much with all the big fences around the perimeter.  I paused at the back door, I could feel my heart beat rising up. What if the neighbors see me like this? I would be in so much trouble? Maybe it was a bad idea. But something inside me was telling me it was now or never! I might never get another opportunity like this.

I was feeling the rush, it was so intense, and I wanted it so badly. I opened the door and stepped outside. I instantly felt so vulnerable and exposed like never before in my life. I looked around to check if any of the neighbors were outside. I didn’t see or hear anyone. I decided to take some pics and videos fast and go back in the house. I set up the tripod & phone and started recording myself. Strangely it felt like I was being watched the whole time. My senses were on full alert! My eyes and ears were automatically scanning around from time to time involuntarily. But there was no one!

Slowly, my confidence returned and I felt more at ease. It was such an intense sensation to be out of the house, even though it was just on my backyard. To be out in the open was just so different, it was an incredible experience. I felt so happy and grateful that I was able to express & experience my feminine side. I clicked a lot of pics and recorded plenty of videos. It was so much fun! I finally looked at the watch and another hour had easily passed by. ready for crossdressing in public

I sat there trying to grasp everything, every emotion that I was feeling. I wanted to record everything I was experiencing at that moment in my head. I didn’t want this wonderful feeling to end.  I wondered what I should do next now. Maybe something even more adventurous? Then I got this idea of maybe going out in public. That would be the ultimate feminine experience for me. I didn’t know what came over me at that instance but I just knew I had to do it. I didn’t care about anything else now. The rush was just too strong!

I went back inside the house and went straight to the bedroom. Then I took out one of Janice purse. I put my phone and the house keys inside it. Then I took out an overcoat from Janice’s wardrobe and put it on. In case any of the neighbors did see me, I didn’t wanted them to see me in the way that I was dressed.  I grabbed the car keys and reached the front door. I took a peak outside from the window to see if anyone was out in the streets or if there were any neighbors out of their house. I saw no one.

This was it! I took a deep breathe and stepped out. My heart was beating like crazy. I locked the door and marched straight to my car without looking anywhere. It felt like million eyes were gazing at me. Walking from the front door to the car felt like a mile’s walk. I reached the car, opened it and got inside.

Once I was in the car, it felt more safe. I glanced around and there wasn’t anyone there. I knew I couldn’t sit there for long, somebody will surely see me. So, I started the car and just drove. It was the most intense thing that I had ever done in my life but it felt great!

Once I was out of my neighborhood, I stopped the car and took off the overcoat. Then I saw a car coming from ahead and I almost had a heart attack. It was my first public encounter with someone as a woman.  I couldn’t stop my body from shaking. I pretended to search something on the passenger’s seat to cover my face from anyone that was in the other car. Once the car had passed, I breathe a big sign of relief. I decided to drive to a near by departmental store, not a lot of people went there since a new mall opened up near by.

Driving in heels so so hard and every time a car passed by I would just freak out. But I loved everything that was going around me. I managed to get used to this new feeling  and just did my best to avoid any eye contact with the people in the passing cars. I finally reached the parking lot of the store. There was only one car parked there. I knew it would be just too much to go inside the store. I would surely be found out. So I just took out my phone and decided to click some pics inside the car and leave.

Just then, a car came out of nowhere and parked near me. My heart stopped! I didn’t have the courage to look. So, I  pretended to be busy on the phone. I only looked up once I heard the footsteps going away. I looked and it was an elderly lady and she slowly walked into the store. I knew that was enough interaction for me. I didn’t want any more close encounter with people. So, I started the car and decided to drive back home.

On the way, I parked on an empty road and got out briefly, pretending to check the tires. It was so wonderful, the feeling of wind on my pantyhose legs, hair floating in the breeze and the freedom of being out. I was just starting to really enjoy the moment when I heard a car coming by and that gave me a big fright! I jumped back in my car and pretended to search something in the passengers seat once again until the car drove by. It would take a lot of going out to be used to these kind of encounter for sure I thought.

I put on the overcoat and slowly drove back home. I enjoyed the ride back so much. It felt like if I was driving out in the open roads for the first time. When I reached my neighborhood, I could feel my heart beat rising up again. I really hoped there weren’t any neighbors outside.

Luckily, there were none when I reached home. I parked the car as close as I could to the front door as possible. Then I made a run to the front door, opened it as fast as I could and went inside. Once inside, I could feel my mind and body finally being able to relax and not having to be on a full alert mode.  I couldn’t believe how a normal day turned out to be the biggest day of my life. There was a big smile on my face. A day out as a woman and it was beautiful.

Submitted by Samantha 

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  1. Wonderful!! My limited times out and about as Laura were always filled with a kind of euphoria as well! On a business trip to Omaha, I began my return trip as Laura and drove for quite a while just loving the feeling of the air under my dress and being blown around by the breeze in the car. I stopped at a little park on my way back for some photos. It was what is called a “Freedom Rock.” Each county in Iowa has one. It was WONDERFUL to get out in the sunshine and felt so very free!!

  2. What a wonderful story, thanks for sharing. And good for you having the nerve to live out your urges. Very curious about the follow up though. Shaving your legs is the best feeling! But explaining it is another thing 😉

  3. hello

  4. Yes it’s much more fun been a girl, to feel the cool night air on your stocking clad legs feels fabulous, but then feeling the odd breeze wafting around the hem of my miniskirt & cooling the bare skin above my stocking tops, but the best bit is hearing the evocative clatter of my 4″ cfm stiletto heels, WOW it feels so good been a girl xx

  5. Great story…luv everything about it..It is so great when you get to dress and spend time as your true gurl self. I hope we hear more about your adventures.

    Hugs and Kisses

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