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My Girlfriend Asked Me to Crossdress In front of Her !

My Girlfriend Asked Me to Crossdress In front of HerSince a young age, I was fascinated with girls clothes. I loved how cute my sister’s outfits were than mine when we were kids. She was two years older than me. One day, when no one was around, I wore my sister’s dress and stockings for the first time and I instantly felt like a girl.  When I looked at the mirror, I no longer saw myself as a boy. I completely fell in love with dressing as a girl.

After that, I couldn’t stop wanting to look and feel like a girl. I started sneaking into my sister’s room and wearing her clothes; skirts, dresses, leggings, and even my sister’s bra and panties. The more I dressed, the more I wanted to explore my girly side.



One day, I found a bunch of my sister’s old clothes in the store room and it was really exciting. There were two dresses, her old school uniform ( a white shirt, gray pleated skirt & school tie), two t-shirts, and one black skater skirt. I also found an old black wig that belonged to my mother from halloween. I was trembling with happiness, I grabbed everything and hid the stuff in my room.

That night, I dressed up all night and it was so magical. When I wore the wig and the outfits, I looked and felt like a real girl. The feeling was just amazing. After that, I would dress up every night in my room and it went on for quite a while until I got caught!

One Saturday afternoon, when I was alone in the house, I was dressed in my sister’s old school uniform, which was my favorite outfit to wear at that time. I was walking around the house and having a lot of fun being a girl. My parents were out of town that day and my sister was at her friend’s place. She was only supposed to come home in the evening but she arrived home early.



When my sister came in the house, I was in the kitchen downstair completely unaware that she had arrived. As I walked out of the kitchen, I saw my sister standing right in front of me and she saw me. We both jumped with fright! My sister looked completely shocked and stared at me from top to bottom. I was having a major panic attack! I felt so embarrassed and had no idea what was going to happen now.  After few moments of silence, she realized I was wearing her old school uniform and she couldn’t stop giggling!

“Oh my god! What are you doing? Why are you dressed in my school uniform? And is that mom’s wig you are wearing?” she asked me, staring at me with a big grin on her face.
I didn’t know how to respond. I tried to speak but couldn’t. My sister was giggling the whole time. After a while I finally managed to speak:

” I just wanted to see how it felt to dress as a girl..”. I told her, my face becoming redder and redder by the moment.

“How long have you been dressing up? Do you want to be a girl?”. My sister asked me.



I blushed hard hearing the question. I was too embarrassed to tell her the truth, so I lied: “It’s just today, I was just curious.. and nothing else!”. I told her.

My sister gave me a weird look. I knew she didn’t believe me. I was getting more and more nervous standing there in front of sister. I felt so exposed dressed in her school uniform, just like a vulnerable young girl. I felt so ashamed and angry at myself for not being careful. Now my sister knew I liked dressing up as a girl!

I apologized to her and begged her not to tell our parents. I said it was my first and last time dressing as a girl. She was understanding and didn’t tease or scold me. She was being a good sister and she said she was always there if I wanted to talk about it and I said okay. She never told our parents about what happened between us and I am very grateful to her for that.



It was always strange after that moment; I was too scared to dress up inside the house or tell my sister that I really wanted to dress as a girl sometimes. Many years passed and I did everything I could to suppress my crossdressing urges. I would watch videos of other crossdressers and boy to girl transformation videos on YouTube to satisfy my desire to dress up.

It was only after joining college, I moved to a new apartment alone and I started crossdressing again and it felt so amazing as it did in my early days. I would dress up quite often inside the apartment and do everything like a girl would do. I was so obsessed with looking as feminine and convincing as a beautiful girl. I would spend hours learning makeup, walking in heels, practicing feminine postures and gestures, basically everything I could do to look and pass as a girl.

I spend a lot on women clothes, makeup, wigs, heels, lingerie and everything girly! I got a lot better in my transformation from a guy to a girl and it made me feel very happy. I started posting my photos online and also made so many new crossdresser friends and admirers. It felt amazing to share my feminine self to the rest of the world. I was hooked!



After a year of college, I started dating a girl because she was also into online games and music, just like me. Her name was Riley and I liked hanging out with her. We started getting more closer to each other and I had to be really careful to hide my crossdressing side from her.

Riley was coming over more frequently to my place. So I knew, I had to hide everything from her and anyone else coming in my apartment. I brought a big black container and kept every feminine items inside it and locked it inside the storage room. I started dressing up only at nights to avoid any bad encounters or getting caught.  So, few nights a week, I would dress up from head to toe and enjoy my girl time inside the apartment. I was happy!

One night, I came home pretty drunk after hanging out with few of my college friends.  I don’t know why but I was so charged that night. I wanted to dress up so badly and be handled like a woman. I got dressed in a matching red bra and panty set, sheer black pantyhose and a pink bodycon dress.



I put on makeup and my blonde hair wig. I did a decent job with makeup even though I was so tipsy. I looked hot! Then I put on my 2 inch pumps and I was ready! My heart was pumping with excitement. I put on some pop music and started dancing my heart out. Then I started taking videos of myself dancing and fooling around. It was so much fun!

After half an hour I needed a drink. I poured myself some whisky and went near the window to also have a smoke! I was loving every moment of it. I felt so feminine, so womanly, so powerful! I had no idea why but at that moment, I just wanted to be with a man who would caress and make love to me while I was dressed like that. I couldn’t stop thinking about it and it was making me super charged.

I went to the bedroom, put on some music and started stripping in front of the mirror. I was feeling hard and fabulous! Then I made love to myself, imagining I was a hot woman and I came hard.. It was so satisfying.. I was pretty tired then and decided to go to bed without cleaning my makeup and taking off my wig. I put on the bra, panty, and the dress back again and went to sleep like a girl.



Next morning, I woke up with the phone ringing and it was my girlfriend. She said she was on her way right now to my apartment and arriving in the next 10 mins or so. I looked at the watch and it was 9:30 am already. I had overslept and now my girlfriend was coming over while I was still dressed like I was. I started to panic and as soon as I put down the phone, I rushed to clean myself up and also my room.

I took off everything that I was wearing, put on my normal guy clothes. Then went to the bathroom, washed my face hard so there was no trace of makeup. Next, picked up all the feminine stuff, put everything back in the container and locked the store room door. Then I went back to the bedroom and tidied everything up and do a double check.

Just then, the door bell rang and it gave me such a fright! My heart started beating faster. As I went to open the door, I couldn’t stop thinking whether or not I had missed anything to hide or remove. I opened the door and greeted Riley with a smile nervously. She came in and my heart was still beating fast. I really hoped I had taken care of everything from last night dressing session.



Riley went to the kitchen and made some coffee. She had brought some cup cakes and we ate and talked for a bit. She didn’t suspect anything and I started feeling normal again.  We hung out for a bit and she said she had to go to her yoga classes in a bit. She went to the bedroom to change into her gym clothes. I was sitting in the sofa in the living room.

After a few minutes, Riley scaremed my name loudly from the bedroom. I turned and saw Riley coming out of the bedroom. Her face looked pretty angry. She was holding a lipstick and pointed it to me. My heart stopped! I had forgotten to hide it. It was the worse feeling. I didn’t know how I was going to explain it to her.

“What is this?? Have you been cheating on me?” Riley screamed at me!

“NO! its not what you think!” I said, my whole body trembling with fear.

“Then explain it to me! or else.. its over between us”. She ordered.



I sat there, everything was complete silence and then Riley started crying! I felt terrible and ashamed! I knew she would never understand if I told her I was a crossdresser. She would think I was such a freak!! But I had no other option than to tell her and I did! I told her everything about my crossdressing and Riley listened in horror. No wonder, she was completely in shock when I told her I liked dressing as a girl sometimes.

After I told her everything, she sat down on the sofa with a confused expression on her face. I knew she was having a hard time processing all the things I told her. I gave her time to respond and waited quietly for her reaction.

After few minutes, she asked “How long have you been doing this?”.

I said “Since I was 14 years old!”, feeling embarrassed.

Riley paused again for a bit, took a deep breathe, and asked me again: “Do you like guys? I had no idea about your crossdressing desire! Would you have never told me if I hadn’t caught you?”.



“No! I just like to dress up sometimes. I don’t know why! I am not into guys, I promise! Its just that its very hard to explain why I like dressing up. Its not that I haven’t tried everything I can to suppress it. But I never could stop it! I am really sorry, I really am but I completely understand if you don’t want to be together anymore! I am so sorry.. I kept this a secret but I didn’t know how to tell you about this.” I replied covering my face with shame.

“Do you have pics of you dressed as a girl?” Riley asked me, her voice now a bit softer.

I was so scared with her question. I didn’t know how to respond to that. If I showed her my feminine self, things would never be same after that. And I was really sacred how she would react to the photos! She might think I am such a sissy!

“Please! I need to really see this”. She insisted with watery eyes.



I said okay and took out my phone. My hands were shaking like crazy! Then I opened a pic where I was dressed in a black bodycon dress, nude pantyhose and heels with full makeup and wig.  I took a deep breathe and handed the phone to Riley.

I could tell from her face that she was shocked!

“Is this really YOU??” Riley asked with disbelief, her mouth wide open.

I nodded. She then scrolled through the pics and there were a lot of naughty pics in there too. I felt so embarrassed and guilty. I wanted to snatch the phone back before she saw everything but I was too sacred to do anything!

Riley went through all the photos and I knew our relationship was over now! I felt miserable and weak. I couldn’t believe this was how it was going to end.



“Wow!! You really surprised me today! I had no idea you liked being feminine and also so naughty! But you do look pretty good as a girl, I would have never guessed! Are you sure, you like girls and not guys?”. Riley asked with curiosity.

“I promise, I am not in to guys! I just like dressing up sometimes! I will stop dressing up, I promise”. I replied feeling embarrassed.

Then Riley said: “This is a lot for me to process. I need some time to think.. I don’t know what we are going to do about this! You should have told me about this before.. I feel cheated and hurt. I might not be able to go through this with you.. I need some time to think”.

It was the worse feeling ever, getting caught and broken up the same day. Then Riley left and I had never felt so bad and lonely in my life. Few days passed and I was so depressed. Riley was not answering my texts or calls. Then one morning, I got a call from Riley and she said she was coming over to my place. That cheered me up a bit. I really hoped Riley would listen to my apology and forgive me.



I waited anxiously for Riley’s arrival. It felt like time was moving so so slow. So many thoughts were racing through my mind and I was also feeling very nervous to face Riley. Finally she arrived and my heart started beating a lot faster when I saw her. She came in and sat on the sofa. I followed and sat next to her.

“How have you been?” Riley asked me.

“Not good really! I feel terrible for hiding my secrets from you. I promise I will never dress again! Please just forgive me Riley!” I replied becoming too emotional out of no where.

“I thought about it a lot and I am still trying hard to process everything. Since I saw your pics, those images of you have been constantly in my mind. I can’t stop thinking about it and wonder if you actually may want to be a girl full time in the future.'” Riley said with a sad tone in her voice.



“NO!! Its not like that.. I only dressed a few times and I swear I will completely stop! You have to believe me Riley, please!” I begged her.

“Okay, I am willing to give it another chance but the only way I think I can move past this is to actually see you as a girl with my own eyes!” Riley said nervously.

My heart stopped and my body went cold instantly. I was shocked with what Riley just told me. How could I dress in front of her, I would die of embarrassment.

“Please Riley! I don’t think I can ever dress in front of you! Its too humiliating for me!” I begged her.

“I need to see you as a girl so that I know how I feel about it. Its not that I want to make you feel embarrassed but I really need to understand if I am okay with this! So, I need you to crossdress in front of me!”. Riley said as she started to whimper.



I was so shaken, just by thinking about what Riley was asking me to do. I felt like I had no other choice but to show Riley my feminine side.

“Okay, I will do it!” I said nervously.

Riley looked at me with a hopeful smile and grabbed my hand. Then, she came closer and kissed me on my cheek.

“Okay, I am ready whenever you are..” Riley spoke softly.

I nodded and stood up slowly. I was so scared and ashamed!

“Are you really sure you want to see me dressed up?” I asked Riley one last time. Riley nodded!

I got up and went to store room to get my feminine stuff. I was terrified about what was going to happen next. Slowly, I opened the container and I was completely blank! A shiver went through my whole body and I was regretting everything. With a deep breathe, I tried to focus again but I couldn’t decide what I should wear.



After thinking really hard for a bit, I realized that if I was going to dress up and show Riley my true feminine side, I might as well go full way and look as feminine as possible. I started feeling a bit confident now but I was really scared how Riley was going to react seeing me as a girl!

Finally, I picked up a grey bodycon dress, a padded bra, panty, black pantyhose, heels and my brunette wig. As I undressed, my heart was racing faster and faster. I put on the bra and panty first. Then I stuffed the bra with some socks. After that, I put on the pantyhose and then the dress. I couldn’t believe it was really happening with me.

My head was overflowing with so many questions and I was really scared. I managed to put the wig on me and lastly, put on the heels. I was ready! I gave myself one last look in the mirror. This was it! I called to Riley that I was ready and she told me to come out. My whole body was now trembling with fear and embarrassment. I took a deep breathe and walked out slowly.



The sound of my heels filled the air. I felt more and more nervous with every step I took forward. As I walked out slowly, Riley was standing there, waiting for me. When I saw her it felt like my heart was about to explode! Riley shouted in shock when she saw me. I could feel her gaze one me. It felt like I was standing there in a very bright spotlight.

“WOW!! I can’t believe its really you! You look totally different.. You look pretty cute than I imagined! Wow..just wow.. I can’t believe it..” Riley shouted at me with a lot of excitement in her voice.

That made me even more nervous. I didn’t know how to respond to that. I just wanted to get it over with.

“Can I change back now?” I requested Riley.

“No.. come here and sit down with me.” Riley demanded.



My hope of making out of it quick went in flames. I sighed and walked slowly towards Riley and sat down next to her. All the while, Riley was eyeing me like a candy and I couldn’t even look at her face. I was so embarrassed. I just sat there having no courage to speak or look back at Riley! We sat there silently for a few minutes and then Riley finally spoke.

“Its amazing how feminine you look and how well you carry yourself as a girl! I can tell you have been doing this a long time! I am really surprised today!” Riley said while coming a bit closer to me. Then she stroked my hair gently and lifted my face with her hand. She wanted me to look at her. I was so shy and nervous! I tried looking away. But she was very persistent and I finally looked at her! It was terrifying! I couldn’t do it and looked down at the floor again.

“Why don’t you say something? How do you feel? Do you like it that you are crossdressing in front of me?” Riley asked.



“No, not really.. I don’t feel very comfortable doing this! Can I please go and change!” I begged her.

“Its okay honey! I think we can do something about this! Looking at you right now, it doesn’t feel as awkward as I imagined it would be. You kinda look cute and I think I will be okay with you crossdressing.. as long as you are honest with me about it. But you have to promise that you really like me and you don’t have feelings for other men!”

I was a bit relieved hearing that. I nodded and we hugged. It felt so strange when our bodies touched. It felt like it was my first time hugging her! I don’t know if it was because I was dressed as a girl or it was the circumstances! But I slowly started feeling a lot more comfortable in front of Riley now.



Then we talked for hours about my crossdressing and how both of us were going to handle it. She had so many questions and I patiently answered her every question. She seem to be satisfied with my answers and told me that she trusted me. I thanked her and we kissed! It was so different and I asked Riley if it was okay with her. She said it was no different than before with a smile! I was so relieved. Then Riley had to leave to meet a friend and we hugged before she left. I was so so relieved and happy!

After Riley left, I just sat there thinking about everything that happened. I couldn’t believe that Riley was so understanding and accepted my crossdressing. I could feel a new sense of freedom and it made me feel so much lighter. I decided to spend the rest of the day as girl and did my makeup and got ready properly. Then I took a lot of photos& videos and spent the whole day as a girl. It was amazing..



Riley and I dated for a year after that and then we broke up! During our time, she dressed me a couple of time and she was really supportive. I wished we went out in public together but it never happened. But I am still very happy that she supported my crossdressing and I will always be so grateful to her!

Submitted by Jenny.

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3 Comments

  1. No. 1, Jenny is sooo attractive now. Even though Riley is no longer with her. It is my wish that Jenny and I could chat… because I suspect what’s going on in her life now that her gf is no longer with her.

  2. Loved the story…it is so true for me on how I feel when crossdresser. I luv you had a supportive friend. Would definitely luv to hear more about your adventures after you broke up.

    Hugs and kisses
    Amber

  3. Loved this story and read it twice
    Stay true to yourself because you are special person

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