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(Join my patreon) I'd rather wear a dress (Updated story) (Old story is below)

Well, it’s that time of the year, prom is coming up. Most of the people at my school were excited about it, asking people out and get their prom outfits to read. On the other hand, I wasn’t looking forward to it, so I was doing everything I could to avoid it. That was until I got home one day and my parents were waiting at the door. They were excited and hiding something behind their backs when I asked what was going on they pulled the item out.

It was a nice black suit, they got it for me to wear to prom. Looking at it made me feel so bad. I just awkwardly accepted it and put it into my backpack. I thanked them and made some sort of excuse so I could leave. I texted my girlfriend and asked if I could come over for a bit, and she said yes, so I headed over to her house. I got there and we went to chill in her bedroom. I tossed my bag on the floor and I laid on her bed.

I guess she noticed my bad mood because she sat next to me and asked me what happened. I sighed grabbed my bag and pulled the suit out. I showed it to her and she nearly died laughing when she pictured me in it. She knew I’d never wear this thing, never mind to prom. I’ve never liked typical masculine stuff, that's the reason me and my girlfriend started dating. She liked having someone to practice makeup and hairstyling on and I liked the feel that came with being cute.

So I tossed the suit on the floor and kept sulking on her bed. She took the suit and held it against herself. She said it was close enough to her size that she could wear it, although she might have to have it fitted a bit. Confused I sat up, I told her she was free to keep it but why did she want to wear that thing? She smiled at me in a very similar way my parents did when they handed me the suit and I sorta of began to panic.

She went to her closet and returned with a similar bag the suit came in and unzipped it. Inside was a gorgeous purple and white prom dress. I was in awe, I smiled and told her she’d look great in that. Then it hit me, I asked her why she had a prom dress if we’d never even talked about going. She nodded her head and told me I was wrong, she didn’t get herself a prom dress, she got it for me.

She forced the dress into my hands and I just stared at it for a moment before I started to cry. My girlfriend began to worry she made some sort of mistake and tried to apologize, but I stopped her and hugged her tightly. I loved it so much, I thanked her over and over again while still crying like crazy. After a while she got me to stop crying by telling me to try it on. I wiped away my tears got undressed, and prepared to get into the dress.

My girlfriend stopped me saying I should wear it properly. She handed me a pair of her panties and one of her bras that had extra padding in it. I looked at her and turned bright red, but she laughed and said I was about to wear a dress, it’s too late to be embarrassed. She was right, but it was still more than I’ve ever done when it comes to being feminine, I mean this is full-blown crossdressing territory now. I slip the underwear on and she helps me clip the bra in place.

After that, I slip the dress up and my girlfriend zips it up in the back, she tightens the waist strings and ties them into a pretty little bow on my lower back. I began to play around with the dress, while my girlfriend got into the suit I brought. Once she was fully into the slightly baggy suit she began to play some music from her phone, and I turned to see her in the suit. I smiled at her and we went up to each other and started dancing in her room.

It was such a magical night, and I knew it was only a fraction of how amazing our prom night together was going to be. We eventually fell asleep on her bed cuddling, while still wearing our prom outfits. Two weeks later prom night was here. I snuck out of my house without my parents noticing and made my way to my girlfriend's house. She did my hair and makeup and I slipped into the prom dress while she got into the suit.

I had everything but shoes on and when I was about to put my normal shoes on my girlfriend walked out with another present. It was a pair of pretty dark purple heels, and they were exactly my size. I basically screamed like a happy little girl when I saw them. I slipped them on and started to walk around to get used to them. Luckily the heels were low, so it was like walking around in slightly taller shoes.

My girlfriend wrapped her arms around me and we walked downstairs together to see her parents smiling and holding cameras. They got us to take many photos alone and together so they could put them in their family photos book. I’m really glad her parents are awesome and are supporting us both in our decisions to crossdress at prom. After they got their photos her dad drove us to school, and we entered the prom.

I knew no one at prom would recognize me with the way I was dressed, but they would recognize my girlfriend so they’d be able to figure out it was me under this dress. So after tonight, everyone will know the real us. We started to get a ton of stares as we made our way to the dance floor. We pulled each other closely and started to dance despite all the looks we got, but eventually, the looks went away and everyone started to have a good time.

We danced, ate food, drank punch chatted with friends, some of whom had many questions or merely congested us before heading back to their dance partners. We had a blast, at the end of the night my girlfriend's mom picked us up and brought us back to her house. Now we were once again laying on her bed cuddling and talking. That’s when my girlfriend said something both kind of scary and exciting. She asked me what would happen if we decided to stay like this.

I asked her what she meant and she pointed at her suit and my dress. She said what if we stayed like this, swapped. She could be my boyfriend and I could be her girlfriend. I looked up and said nothing. She went on to say I clearly like dresses and makeup more than her, and she likes suits and other masculine things, so it would be perfect if we just switched. She even told me her parents we willing to accept us both if we decided to do it.

She turned her head towards me and pulled my head towards hers. She then asked if I wanted to be a girl, but not any girl, his girlfriend. There were so many thoughts passing through my mind, but I already knew my answer. Yes, I’ll be your girlfriend from now on, and you can be my boyfriend, I said smiling and kind of crying. I pointed down and said it made sense anyway, after all, It seems I’d rather wear a dress than a suit.

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I'd rather wear a dress (Original story)

My high school prom was coming up and everyone was off asking people out and getting their prom outfits. My parents were excited and had already gotten me a suit to wear. I awkwardly accepted and threw it in my bag and headed to my girlfriend's house. I’ve never really liked masculine stuff, it’s actually why me and my girlfriend started dating. She liked having someone who liked the things she did, she always got to practice makeup and hair on me.

When I got to her house she was super excited to show me her prom dress. She looked great in it and I told her so. She was jumping around and dancing in it until she noticed I didn't look happy. She asked me about it and I told her about the suit. That’s when she got a huge smile on her face and ran out of the room, I was kinda freaked out by that. When she returned she had another beautiful dress, she handed it to me and told me it was mine.

I just stood there in silence, and then I started crying. She thought she had made a mistake and tried to apologize. I told her loved it but what would people think if I wore this, what would my parents say? She told me that plenty of men like to crossdress and some people are transgender meaning that they don't feel like the gender they were assigned at birth. She said that she was planning to give me the dress and ask me about it.

I didn’t really have an answer to that as the concept was new to me, I do like all the things that girls like, perhaps I am. She told me to go to the prom with her like this and afterwards to make a decision, and no matter what she'd support me. Well tonight was the prom, you should have seen my parents' faces when I walked out as a girl in a dress instead of a boy with a suit. No one at prom recognized me but I’m sure they put two and two together when they saw me dancing and kissing my girlfriend.

Right now I’m sitting in my girlfriend's bed, we’re both still wearing our dresses and cuddling. I looked over to her and thanked her, I’ve never felt so amazing and free. She asked me if I had made a decision. From then on I never wore another suit, I’d rather wear a dress!

Description
(Join my patreon) I'd rather wear a dress (Updated story) (Old story is below)

Well, it’s that time of the year, prom is coming up. Most of the people at my school were excited about it, asking people out and get their prom outfits to read. On the other hand, I wasn’t looking forward to it, so I was doing everything I could to avoid it. That was until I got home one day and my parents were waiting at the door. They were excited and hiding something behind their backs when I asked what was going on they pulled the item out.

It was a nice black suit, they got it for me to wear to prom. Looking at it made me feel so bad. I just awkwardly accepted it and put it into my backpack. I thanked them and made some sort of excuse so I could leave. I texted my girlfriend and asked if I could come over for a bit, and she said yes, so I headed over to her house. I got there and we went to chill in her bedroom. I tossed my bag on the floor and I laid on her bed.

I guess she noticed my bad mood because she sat next to me and asked me what happened. I sighed grabbed my bag and pulled the suit out. I showed it to her and she nearly died laughing when she pictured me in it. She knew I’d never wear this thing, never mind to prom. I’ve never liked typical masculine stuff, that's the reason me and my girlfriend started dating. She liked having someone to practice makeup and hairstyling on and I liked the feel that came with being cute.

So I tossed the suit on the floor and kept sulking on her bed. She took the suit and held it against herself. She said it was close enough to her size that she could wear it, although she might have to have it fitted a bit. Confused I sat up, I told her she was free to keep it but why did she want to wear that thing? She smiled at me in a very similar way my parents did when they handed me the suit and I sorta of began to panic.

She went to her closet and returned with a similar bag the suit came in and unzipped it. Inside was a gorgeous purple and white prom dress. I was in awe, I smiled and told her she’d look great in that. Then it hit me, I asked her why she had a prom dress if we’d never even talked about going. She nodded her head and told me I was wrong, she didn’t get herself a prom dress, she got it for me.

She forced the dress into my hands and I just stared at it for a moment before I started to cry. My girlfriend began to worry she made some sort of mistake and tried to apologize, but I stopped her and hugged her tightly. I loved it so much, I thanked her over and over again while still crying like crazy. After a while she got me to stop crying by telling me to try it on. I wiped away my tears got undressed, and prepared to get into the dress.

My girlfriend stopped me saying I should wear it properly. She handed me a pair of her panties and one of her bras that had extra padding in it. I looked at her and turned bright red, but she laughed and said I was about to wear a dress, it’s too late to be embarrassed. She was right, but it was still more than I’ve ever done when it comes to being feminine, I mean this is full-blown crossdressing territory now. I slip the underwear on and she helps me clip the bra in place.

After that, I slip the dress up and my girlfriend zips it up in the back, she tightens the waist strings and ties them into a pretty little bow on my lower back. I began to play around with the dress, while my girlfriend got into the suit I brought. Once she was fully into the slightly baggy suit she began to play some music from her phone, and I turned to see her in the suit. I smiled at her and we went up to each other and started dancing in her room.

It was such a magical night, and I knew it was only a fraction of how amazing our prom night together was going to be. We eventually fell asleep on her bed cuddling, while still wearing our prom outfits. Two weeks later prom night was here. I snuck out of my house without my parents noticing and made my way to my girlfriend's house. She did my hair and makeup and I slipped into the prom dress while she got into the suit.

I had everything but shoes on and when I was about to put my normal shoes on my girlfriend walked out with another present. It was a pair of pretty dark purple heels, and they were exactly my size. I basically screamed like a happy little girl when I saw them. I slipped them on and started to walk around to get used to them. Luckily the heels were low, so it was like walking around in slightly taller shoes.

My girlfriend wrapped her arms around me and we walked downstairs together to see her parents smiling and holding cameras. They got us to take many photos alone and together so they could put them in their family photos book. I’m really glad her parents are awesome and are supporting us both in our decisions to crossdress at prom. After they got their photos her dad drove us to school, and we entered the prom.

I knew no one at prom would recognize me with the way I was dressed, but they would recognize my girlfriend so they’d be able to figure out it was me under this dress. So after tonight, everyone will know the real us. We started to get a ton of stares as we made our way to the dance floor. We pulled each other closely and started to dance despite all the looks we got, but eventually, the looks went away and everyone started to have a good time.

We danced, ate food, drank punch chatted with friends, some of whom had many questions or merely congested us before heading back to their dance partners. We had a blast, at the end of the night my girlfriend's mom picked us up and brought us back to her house. Now we were once again laying on her bed cuddling and talking. That’s when my girlfriend said something both kind of scary and exciting. She asked me what would happen if we decided to stay like this.

I asked her what she meant and she pointed at her suit and my dress. She said what if we stayed like this, swapped. She could be my boyfriend and I could be her girlfriend. I looked up and said nothing. She went on to say I clearly like dresses and makeup more than her, and she likes suits and other masculine things, so it would be perfect if we just switched. She even told me her parents we willing to accept us both if we decided to do it.

She turned her head towards me and pulled my head towards hers. She then asked if I wanted to be a girl, but not any girl, his girlfriend. There were so many thoughts passing through my mind, but I already knew my answer. Yes, I’ll be your girlfriend from now on, and you can be my boyfriend, I said smiling and kind of crying. I pointed down and said it made sense anyway, after all, It seems I’d rather wear a dress than a suit.

______________________________________________________________________________
I'd rather wear a dress (Original story)

My high school prom was coming up and everyone was off asking people out and getting their prom outfits. My parents were excited and had already gotten me a suit to wear. I awkwardly accepted and threw it in my bag and headed to my girlfriend's house. I’ve never really liked masculine stuff, it’s actually why me and my girlfriend started dating. She liked having someone who liked the things she did, she always got to practice makeup and hair on me.

When I got to her house she was super excited to show me her prom dress. She looked great in it and I told her so. She was jumping around and dancing in it until she noticed I didn't look happy. She asked me about it and I told her about the suit. That’s when she got a huge smile on her face and ran out of the room, I was kinda freaked out by that. When she returned she had another beautiful dress, she handed it to me and told me it was mine.

I just stood there in silence, and then I started crying. She thought she had made a mistake and tried to apologize. I told her loved it but what would people think if I wore this, what would my parents say? She told me that plenty of men like to crossdress and some people are transgender meaning that they don't feel like the gender they were assigned at birth. She said that she was planning to give me the dress and ask me about it.

I didn’t really have an answer to that as the concept was new to me, I do like all the things that girls like, perhaps I am. She told me to go to the prom with her like this and afterwards to make a decision, and no matter what she'd support me. Well tonight was the prom, you should have seen my parents' faces when I walked out as a girl in a dress instead of a boy with a suit. No one at prom recognized me but I’m sure they put two and two together when they saw me dancing and kissing my girlfriend.

Right now I’m sitting in my girlfriend's bed, we’re both still wearing our dresses and cuddling. I looked over to her and thanked her, I’ve never felt so amazing and free. She asked me if I had made a decision. From then on I never wore another suit, I’d rather wear a dress!