Swapped Date Night (YT)

Idea by nicholasfarrell5981 on youtube

It was Friday night, and both Rayna and Branson were together in the bathroom getting ready to head off to a local restaurant for a date night. They’d been doing this every week for the last year, and it was always a very romantic and wonderful night.

Rayna was brushing her hair out while Branson was in their closet looking at his options to wear. As he was there, he called out to Rayna and asked her what dress she was planning on wearing tonight.

Rayna thought about it for a moment and asked him to pull out the blue dress with only one shoulder strap. Branson looked in the closet and smiled when he saw it. He pulled it out and told her it was a lovely choice.

He then grabbed a suit for him to wear and brought both outfits to the bathroom. Once inside, he showed both outfits to Rayna and then pressed each one up to himself and asked which one looked better on him.

Rayna smiled and said blue was definitely his color and that dress would look great on him. Branson got a bit embarrassed and said there was no way he could pull off a dress, never mind one this beautiful and elegant.

Rayna said that wasn’t true; she was sure he could. After all, they were about the same size, so it would fit him, and seeing as he looked pretty androgynous, she was sure no one would be able to tell he was a guy.

Branson laughed and still didn’t believe it, but he held the dress up to himself and looked in the mirror. Rayna saw him staring at himself and asked if he wanted to try it. Branson looked over at her and asked what she meant.

Rayna explained Branson could wear the dress on their date, and she’d help him get dressed up to look nice. Branson let out an awkward laugh and said that was crazy and then asked what she would wear if he did that.

Rayna rolled her eyes and said it wasn’t crazy; it was just clothing. She then said she had tons of dresses she could wear, or perhaps she could join in and dress up as a man and wear the suit he had picked out.

Branson seemed interested and looked at the mirror again. He smiled and said it sounded pretty interesting, but he wasn’t sure that no one would know he was a guy. Rayna nodded and said she was positive.

She then said that as he was now, it was hard to tell he was a guy, but after she got him all dolled up, no one would even question it, and she was so sure she was willing to make a fun little bet about it. If anyone could tell, she’d do the dishes for the next week.

Of course, if no one could tell, Branson would have to do it instead. Branson thought about it for a minute and said he accepted that bet. After all, it was sort of a win-win: if no one noticed, they got to have a fun, unique night, and if someone did, he didn’t have to do dishes this week.

Of course he might be slightly embarrassed about being found out, but like Rayna said, it was just clothes. Rayna jumped up and was excited to be doing this; she had Branson hang their outfits on the shower curtain and then pulled him over to the mirror.

She had him sit down so she could start making him look beautiful. She started with his hair. She brushed it all out and then put a hairnet over it all. She then ran back to their closet and dug through it until she found one of her old wigs.

She brought it back and placed it on his head. She moved it around a bunch of times before settling on a spot. Once she did, she used hairpins to hold it in place so Branson wouldn’t have to worry about it falling out during their date.

Now with longer hair, Rayna could start styling his hair and making it look pretty. She brushed the wig out and then used rose-scented hair spray to make it smell wonderful. Once it dried, she pulled all the hair back towards the back of Branson’s head.

She left one long bunch of hair dangling on the sides of the bangs over Branson’s forehead, and the rest went into a ponytail in the back, held together by a hairband with cute blue roses attached to the side.

Rayna put her hands on Branson’s shoulders and asked him how it looked. He looked into the mirror and turned his head back and forth. He admitted it looked nice, but he still didn’t think he looked like a woman.

Rayna looked surprised and said Branson must be blind, but she’d keep going, as next up was makeup, and he was sure to see his feminine side once she was done. Rayna then grabbed a bunch of things to use.

One by one she used each product, though Branson had no clue what she was using, other than the really obvious things, like blush, mascara, and lip gloss. She also pulled a few of his eyebrow hairs out, which he wasn’t super thrilled about because of how much it hurt.

Once she finished with his face, she had him look at himself again. Branson did what he did before and turned his head back and forth, and sure enough, it was getting harder and harder to argue he couldn’t possibly look like a woman.

Rayna smiled when she could tell Branson was seeing it. She then told Branson to take the dress and head into the bedroom. She also told him to grab a waist cinch and some of her sticky bra pads and wait by the bed for her to come out.

Branson nodded and went right to do that. While he was doing that, Rayna started to get herself ready, which would actually be much quicker for her than normal. She used some of Branson’s hair gel to style her hair to look more boyish.

Next up, she stole his deodorant and cologne. She rubbed her armpits with the deodorant and then sprayed the air with cologne and spun around in it. She then sniffed herself and smiled. She smelled just like Branson, which was nice.

It was almost like when she stole his hoodies and lounged around in them. With her hair done and manly smell achieved, there was only one more thing she had to do before going to help her boyfriend into his dress, and that was for her to get in her suit.

Rayna took everything off the hanger and started by putting on a binder, then she put on the suit pants and white button-up. She then took the belt and looped it around the pants, and then she took the tie and put it around her neck.

Rayna stopped and looked at herself. She had never worn a suit before, and she was only halfway in it and already enjoying how nice it felt and how good she looked in it. She then giggled; no matter how good she looked, she was more excited to see Branson in the blue dress.

Rayna finished getting dressed by putting on the vest, shoes, and finally the blazer. Rayna checked herself out one more time before leaving the bathroom and finding Branson standing in the bedroom with the waist cincher on and attempting to use the sticky bra pads.

He stopped trying when he noticed Rayna standing there. He looked up at her and looked shocked, but in a good way. Rayna struck a manly pose and asked him how she looked. Branson gulped and quickly said, Amazing.

He then said she looked like a very handsome man. Rayna smiled and thanked him; she then got closer and said it was time to make him look like a beautiful woman. She took the sticky bra pads from his hands and helped him stick them to his chest.

They were to make it look like he had some sort of breasts while he was wearing the dress, but with the type of dress he’d be wearing, they couldn’t use a bra, so these strapless pads were the best bet for him.

With them on, and him already wearing the waist cincher to make him look slimmer and curvier, all that was left for him was the dress and a matching pair of short heels, since he had no experience wearing them.

Rayna held the dress for Branson as he stepped into it, and then she lifted it up for him. Once it was over his shoulder, Rayna went behind him and found the zipper. She grabbed it and pulled it all the way up, making it so the dress would not stay up on Branson as he walked around in it.

Once she stepped back, Branson looked down at himself and twisted his body back and forth to make the dress move. Rayna, watching him, could tell he was enjoying wearing it and perhaps enjoying being a cute girl.

Rayna let him enjoy it peacefully for a minute while she grabbed the heels. Rayna came back with them and showed them to Branson and asked him if he was okay with walking around in them. He looked a bit embarrassed but excited at the same time.

He lifted his dress, and Rayna bent down and put each of the heels on his feet. With that, both of them were dressed in each other's clothes and ready for their crossdressing date night. Branson, walking slowly, went over to his end table and grabbed his wallet.

That’s when he heard Rayna clear her throat. Branson turned and found she was holding a very pretty blue purse that matched perfectly to the dress he was wearing. She handed it to Branson and took his wallet out of his hand and put it in her suit jacket.

Branson let out a smile and put the purse strap around her uncovered shoulder. Rayna then stuck her hand out for Branson to grab, and the two of them finally left their house and made it to their car. Normally Branson would drive, but Ranya wanted to drive.

So Branson let her, as he really didn’t care, but also because he didn’t want to drive barefoot since he knew there was no way he could drive in heels. About a half hour later, they arrived at the restaurant.

Rayna parked the car and then quickly got out and ran around to open the door for Branson. She then reached her hand out for Branson to take. Branson chuckled and took it, allowing Rayna to pull him up out of the car and into her arms.

The two then walked into the restaurant, and Branson noticed right away that people were staring at him. He pulled Rayna closer; he was starting to get really nervous and really embarrassed. Rayna, noticing him holding her tightly, looked over.

She followed Branson's gaze to see what he was looking at and then noticed all the men staring at him. Rayna started to laugh quietly to herself because she knew those men thought they were looking at a beautiful girl.

After waiting in line, they made it to the hostess. She asked for the name on the reservation, and Branson was about to answer since he was the one who made it, but Rayna chimed in, not only saying Branson’s name but also using it as hers.

The hostess checked the reservation book and confirmed their reservation. She then told them to follow her to their table. Rayne grabbed Branson’s arm and led him into the main area of the restaurant, and they followed the hostess to a small two-person table with a candle on it.

Rayna pulled the chair out for Branson and then pushed him in once he was seated. She then sat across from him, and the two looked over the menu until their waiter came over to ask what drinks they would like.

Since Branson usually drove, he normally ordered some sort of iced tea to drink, while Rayna usually had a small glass of wine, so when Rayna ordered iced tea for herself, he knew she was really taking this role reversal to heart.

So Branson was going to order that and enjoy some wine for once, but he found himself frozen in place when the waiter turned and asked what the madam would be drinking tonight. Branson hearing that the waiter actually thought he was a girl shocked him so much he couldn’t speak.

Both the waiter and Rayna looked at him for a minute confused, but Rayna decided to step in and save Branson by ordering the wine for him. The waiter nodded and left to grab their drinks. Once he was gone, Rayna started laughing.

Branson snapped out of it and asked her what she was laughing at. She smiled and said she was just happy that she was right. When they swapped outfits like this, no one could tell she was actually a girl and that Branson was totally a guy; they were both presenting well as the opposite gender.

Branson looked a bit embarrassed but laughed alongside her and agreed. He even admitted so far it seemed he was going to be doing dishes all week. Rayna nodded and said she thought so, but she didn’t want to worry about the bet right now.

Instead, she was enjoying this and wanted to continue having fun. Branson agreed, and they talked about what to order. Like normal, they each ordered something they both thought sounded good as they planned to split both dishes.

The waiter came back with their drinks, placing the tea next to Rayna and the wine next to Branson. He then wrote down their orders and told them it would be out in about thirty minutes. Both of them thanked the waiter, and they started to chat while they waited.

A few minutes passed, and live music began to play in the restaurant. Both Branson and Rayna looked over and saw someone on the piano and someone else by the microphone, and in front of the stage were a few couples slow dancing.

Rayna jumped up and reached her hand out to Branson and asked him if he wanted to dance. Branson’s face turned bright red, and he looked down at himself. He wasn’t sure he could dance in a dress, but Rayna told him not to stress it; she’d lead.

Branson nodded and took her hand, and the next thing he knew, he was led to the front of the stage and was pulled right into Ranya’s arms. Rayna then started to dance around, pulling Branson with her.

Branson trusted her to lead and simply placed his head on her chest and enjoyed the music. The moment was amazing, and both of them found themselves lost in it, so much so that enough time for their food to finish had passed, yet to them it felt like mere moments.

They finished dancing, and Ranya led Branson back to their table so the two of them could eat. This part was the only part of the night that was exactly the same as normal, well, other than the fact they were both still cross-dressing.

They talked about things, shared their food with each other, flirted, and even held hands and stared out the window into the city’s night sky. Once they finish their food, the waiter comes and takes their plates, asks them if they’d be ordering dessert, and then finally comes back with the check.

Branson was about to reach for it, but the waiter placed it next to Rayna instead. That seemed to make Rayna happy, and she quickly pulled out Branson’s wallet and pulled out enough money plus a decent tip and gave it to the waiter.

The waiter thanked her and then left. Branson and Rayna then got up and walked back to their car. Rayna opened the door for Branson and helped him in before going around the car and getting into the driver's seat.

She then just sat there smiling instead of turning the car on. Branson was happy as well but still wanted to know what she was thinking, so he asked. Rayna turned a bit red herself and said that tonight was a lot of fun.

Branson laughed and agreed, saying it was a crazy experience; at some points it was a bit nerve-racking, but overall it was nothing but fun, and as weird as it was to admit, he enjoyed dressing up pretty and acting like a girl.

Rayna looked over and said she enjoyed it as well and really enjoyed getting to stare at a beautiful woman all night, and she really wouldn’t mind doing it again, and perhaps sometime soon, assuming that pretty woman was up for it.

Branson blushed again and held his hands together and thought about it. He then looked up, smiling, and nodded at Rayna. He then said that the pretty woman was free next week. Rayna started the car and said it was a date then, thus kicking off a series of swapped date nights.