Unexpected Journey Dressing Up

Closing the garage door, Erin passed through the laundry room and into the kitchen.

"Kathy!" He called out as he looked around and found himself alone. "I'm home."

Knowing she was somewhere in the house, as her car was sitting next to his, he noticed her purse on the kitchen table.

"Must be upstairs," he murmured before doing a quick check in his office.

Finding no messages waiting, he kicked off his shoes and went upstairs to their bedroom.

"Kathy?"

"I'm in here, sweetie, taking a bath. Why don't you join me?"

One of the first things they did upon purchasing the townhome was upgrade the bathroom. Now, both tub and shower had enough room for two to fit comfortably, which he thought was the best thing he ever did.

"You're filthy," she commented as he opened the door before closing it.

"Our storage place is a bit dusty," he agreed, pulling off his shirt.

"You're wearing a bra? Were you wearing it too when you went to the bank?"

Piling up his clothing, he chuckled. "Yeah, I actually forgot I had it on. When I walked into the bank, it was a little too late to reschedule my appointment."

"Did anyone say anything?" Kathy asked as her husband stepped into the shower for a quick scrub.

"Not a peep."

With the dust and grime off his body, Erin slipped into the bathtub, joining his wife.

"Did you find them?" Kathy asked as she shifted, allowing him in.

"Yep, I found my mom's collection of serving platters; I'm not sure which ones you wanted, so I brought a number of them for you to pick from," Erin said while looking down. "Huh, they really do float."

"Idiot," Kathy snorted. "We'll just take them all, let Mom pick, or maybe just send her some photos. Been told they expect quite the group this Thanksgiving."

"Joy," Erin sighed, sitting back.

"Don't be a party popper. So, I have been thinking."

"Dangerous."

"Funny, ha ha," Kathy said, giving her husband a nudge with her foot. "Well, since you left the house wearing a bra, and you're not freaking out, perhaps this wasn't for the first time?"

Erin shrugged. "Perhaps, besides, I don't need to change if I'm just going to go through the drive-through at lunch."

"Even so, well, I have an idea. Let's dress up when we go out to dinner this upcoming weekend."

"Dress up? Aren't we just going to the food court and seeing a movie? Might be fun, I guess."

"No, you misunderstand. I want to take my girlfriend out to dinner," Kathy explained with a grin.

Girlfriend, huh, yeah, Erin knew where this was going.

"We'll get our nails done; you've been biting them again." She also pointed out. "And you were OK with getting them done last time."

True, when he was anxious, he tended to chew on them. The reason, besides his regular deadlines, it looked like he would need to hire someone new. Which was actually a good thing but didn't help with the stress.

"Your hair also needs a bit of a trim; you're beginning to look scruffy. Oh, let's go to the salon. We can make a whole day of it," Kathy said excitedly.

"Alright, but I just want to point out, my love, that I'm your husband."

"I know." Kathy grinned while rubbing her foot against his cock.

With a frown, Erin grabbed it and rubbed the arch, causing his wife to groan. Ignoring his wife's kinks for a moment, did he want to actually get dressed up as a woman?

He didn't lie about going out to lunch wearing a bra. He might have also forgotten to mention that lately, he'd also been going to the grocery store without changing. However, dressing casually and looking a bit androgynous was quite different from wearing a skirt or a dress.

Of course, Erin wasn't shocked that she would quickly take advantage of this new revelation. Wife had her kinks, and he knew this one well. Back in college, she made him dress up as a cheerleader one Halloween while she wore a football player's uniform. Afterward, well, they didn't get out of bed the entire weekend and were lucky to make it to class the following Monday.

That wouldn't be too bad if that happened again. It was a great way to spend the weekend. And would dressing up really be so terrible? He had some of the right parts now without needing to stuff his bra with tissue.

Funny, he was more upset that it didn't really bother him. A year ago, yes, now, not so much.

One thing he knew, if they went out, she wouldn't embarrass him. That wouldn't end well. He knew it was in her nature to push, but she also understood which lines not to cross. At least, he hoped she did.

"I assume you already have an outfit picked out?"

"Not really; none of what I have will fit you properly anyway. I figure the two of us can go to the mall one evening this week and find something nice for you to wear," Kathy suggested hopefully.

"So, just another excuse to go shopping. OK, I agree provisionally. But it's not a done deal. First, I get to pick the movie. Don't make that face, we'll go to something we both will enjoy. Secondly, I want to eat at Ceaser's Table, the one at Timber Mall. If I'm going to dress up in a way you're thinking, we're going to the other side of town."

"As long as you don't order the Fettuccine Alfredo."

"Wasn't planning to. The new medicine is great, but I have no desire to spend the rest of the weekend on the toilet."

Kathy smiled happily. "OK, sounds good so far. What else?"

"Finally, If I don't like what's happening, I'll cancel, and we can eat at home. I'm serious, Kathy. Let's keep this to a low burn, please, nothing, well, you know, just the two of us having a nice meal and seeing a movie."

Crossing her arms, Erin's wife whined. "I don't know why you would think I would do something bad."

"Because I know you, sweetheart. If it goes well, I would be willing to do it again in the future."

"Really, really?" Kathy almost stood up. "This is going to be so much fun."

The rest of the week flew by; however, the weekend's escapades had been thrust into the back of Erin's mind. The Grumpy Birds project plan had finally been finalized. Candy Smashers had a couple of essential patches in the works, and one of his less successful games had a crossover with a popular anime requiring several early morning video chats. And, thankfully, after half a dozen interviews, he sent an offer letter to one promising candidate from Denmark.

So that was a weight off his chest.

However, Erin wasn't a fool, even if he wasn't dwelling on the weekend. Going out purposely dressed as a woman was a huge fucking deal. It was a giant leap to somewhere. OK, he had been to the grocery store, but shopping for tomatoes in a t-shirt and jeans didn't make him feel particularly feminine. Even if he had a pair of breasts.

Was this really, OK?

He kept returning to the conversation in the tub and what it ultimately meant to him and his relationship with his wife. Especially the lack of real issues with the concept of putting on a dress. In the end, Erin figured, having a pair of tits for almost six months kind of took away most of the anxiety.

And even if his wife would continue to push his boundaries, if he did continue down this path, it would be on his terms, not hers.

Wednesday, however, Kathy almost caused the whole thing to crash and burn as, once again, she was late getting home without a phone call or text.

Bursting into the kitchen in a panic, she apologized. "Sorry, sorry, I know, I know. I was on the phone with Beth planning Thanksgiving; she needed some advice on a few things. Also, Mom asked if you could make those pecan pies you brought a couple of years ago."

Erin gave a frustrated sigh. "Fine, give me your phone."

"What?"

"It needs to be on the charger, even if it's only for a few minutes. Thank you. Now run upstairs and change if we're going to get to the stores before they close; we needed to leave an hour ago."

"I know; I'm sorry, baby," she shouted after giving him a quick kiss and ran upstairs to the bedroom with her shoes in hand.

With no time to sit in a restaurant, the two found a quick meal at the food court before Kathy began to drag her husband all over the mall.

From store to store they went.

New underwear was unnecessary; the wife was sneaky, having already purchased some new sets; shoes were a must, OK, no high heels. You can learn how to walk in them another time. There isn't going to be a time when you would be willing to wear high heels, perhaps. Oh, look how nice these would go with that skirt from the other store. And yes, you need more than one pair, picking out a similar style but in a different color; a pretty floral skirt was discovered at a third store that, apparently, he had to have and later while standing in front of a jewelry counter of now too many stores to count Kathy reached over and played with her husband's earlobe.

"I still have those Celtic crosses you used to wear in my jewelry box. From what I can see, we can just reopen the holes."

"Really?" Like many of the guys in college, he used to wear earrings, but it had been a while.

Kathy grinned. "Don't be a baby, I'll numb it with ice first. How about taking a look in your mom's jewelry box. She gave me a few pieces, but most of hers is in the bank."

"My mom, huh," Erin whispered, touching his earlobe. "You're right; the really nice stuff is in the safety deposit box."

"I'll go by tomorrow and take a look. If I remember correctly, there were some gorgeous emerald studs. They would look good on you, I'm thinking."

Now, with time running out, bags in hand, Kathy began collecting a pile of skirts and tops from the last store.

"Ahh, twelve."

"The limit's six, ma'am," a young, bored teenager pointed at the small poster on the wall outside the women's dressing room inside the larger stores.

"Well, six, then six," Kathy pointed to her husband. "Can we leave these bags here?"

The girl just waved them away, passing two plastic cards with the number six printed on them.

"Alright, go-ahead."

"Ah, it's a little crowded in here," Erin laughed as the two bumped into one another.

At the other stores, his wife stood outside the dressing room and commented as he stepped outside to show her how the different outfits looked.

"The mall is going to close soon. Strip, come on, chop-chop, time's a waste," Kathy insisted as she started to pair up skirts and blouses.

"Do all manufacturers play a bit loosey-goosey with women's measurements," Erin asked, slipping on a pretty baby blue blouse.

"You noticed, huh. That's a gorgeous top, but it's too tight around the chest. Here, try this one."

"It looks like a garden exploded on this one. Do I really need to try on all these things? We're only going out to dinner. How many outfits do I really need?"

"You might change your mind, sweetie, and decide to put on something nice one morning before you go to the grocery store."

"Doubtful."

Kathy shrugged. "You never know."

Saturday would eventually come quickly enough, and the day started rather well when Erin was awoken by his wife moving on the bed, pushing the covers away before wrapping her lips around his morning wood.

Applying suction while moving her tongue around the head, he moaned in bliss and then leaned back as she began to bob up and down.

"Morning baby," she laughed, taking his enter member into her mouth before licking the back side of it up and down to then twirl her tongue around the head before going back down on him.

The morning blowjob would soon end as she started to stroke the now slick shaft while playing with his ass and balls, causing him to squirm in pleasure.

"God, that feels amazing, Kathy." And immediately, Erin began to grunt. "I'm going to come."

"Go ahead, baby, give it to me," she said, opening her mouth as he orgasmed, some of it landing on her nose and cheek.

And just as quickly, she climbed on top of her husband to give him a lusty kiss full of cum. For a few minutes, their tongues twirled back and forth, sharing his load between them. Moments later, Kathy moved his hands away and jumped off the bed.

"Later, we have things to do."

It had already been over two years since they moved into their new townhome, but Eren still didn't really know anyone. The neighbors kept to themselves, and he didn't know anyone except for the workers at the grocers and the various restaurants. He had some old friends, but most were online, and the two guys he hung around in college with had moved to other states and started families.

However, not wanting to make her husband any more anxious, Kathy selected a salon a little bit further away than the one she had been going to.

He wasn't exactly nervous about what they were going to do; Erin had been to one before; he zoned comfortably as one of the technicians worked on his fingers and toes. Yes, he agreed that chewing on his nails was bad before she started working on them.

The dark red nail polish, however, was a surprise. Did he agree to it? No clue. Well, that's what he got for almost falling asleep.

"You have beautiful hair," the stylist commented soon after as she ran her fingers through it. "What would you like me to do with it today?"

"Not sure, really; I was told it's getting a bit scruffy."

"A little bit; the split ends need to be taken care of that's for sure. I have a few ideas; do you trust me?"

"Sure, go ahead. I imagine it will grow back if I don't like it."

That caused the stylist to laugh, "I wish every woman thought the same. OK, lean back."

Less than an hour later and wow, what a difference hairstyle could make.

Looking at his reflection didn't at least to him scream woman; however, in addition to the emerald earrings, the new style made his reflection lean much more towards the feminine side. Although perhaps others saw it differently.

"Well, what do you think?"

"It looks really nice, thank you," he said to the stylist with a grateful smile.

Besides, wasn't that the whole purpose of the weekend, indulging in his wife's fantasies?

Might as well do it right.