Becoming Ashley Ch. 02 - Accepting Ashley

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Ashley dives deeper into her feminine persona.
13.2k words
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Part 2 of the 2 part series

Updated 06/10/2023
Created 01/23/2021
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AshRynn87
AshRynn87
709 Followers

"What's bothering you babe?" My wife Victoria asked.

"Nothing...I'm fine." I mumbled as I fidgeted with my fork, ignoring the majority of my dinner.

"I know you Aaron. You've barely touched your food. You're never not hungry for lasagna." Victoria prodded, determined to get a real response.

"Just not in the mood." I was purposefully short, not wanting to discuss my feelings at the moment.

"Okay. Well...if you want to talk about it, I'm happy to listen."

I continued to pick at my dinner, hoping that she would just let me be. Of course she was right though. She did know me too well and the silence was short lived.

"Is it Teddy?" Victoria prodded.

I let out a long sigh and set my fork down on the dinner plate.

"Yes, but at the same time no." I shrugged.

"I still don't know why you ended things with him. He was a great guy."

This again.

"I've told you several times. It's not like I just broke things off. We wanted different things. He wanted a relationship with Ashley. That's just not something I was able to give him."

For a few months after that first weekend as Ashley, things with Teddy were amazing. Victoria and I came to an agreement that one weekend a month I would be free to be Ashley and could spend that time with Teddy. To be completely honest...I had never been happier. I finally felt free from the burdens of hiding that part of me.

Every month a tiny tension would build inside of me; growing and growing until it finally burst free when I was able to put on Ashley and show her to the world, and more importantly, give myself to Teddy. He made me feel things I didn't think were possible. I melted every time he touched me. When I made love to Victoria, I found myself being jealous of her. Not because of who and what she did while I was with Teddy, but because she got to be the woman all the time and I was stuck as the man all but once a month.

I love Victoria. She has been wonderfully supportive of my exploration of Ashley's sexuality. Without her, I never would have set Ashley free. But at the same time, Victoria is still my wife, and the person I want to spend my life with. I hated the way I felt when I was with her. It was almost like I resented her for being a woman when I couldn't.

About six months ago, Teddy asked for more. He told me that one weekend a month wasn't enough for him. He asked if Victoria and I would be willing to do every other weekend.

At first, I was thrilled. I knew Victoria would be not just open to it, but likely fully supportive. She loved seeing me blossom as Ashley. But the more I thought about it, the more I was filled with dread.

I love being Ashley, but the process had begun to wear on me. It would have been one thing if I was living my life as a woman, but I was Aaron in 90% of my life. The transformation from Aaron to Ashley is not a simple one, and while both Victoria and Teddy were appreciative of my time and efforts, an additional two days of full body shaving, and contouring, and hair styling, and wardrobe picking just felt like a mountain I wasn't able to climb.

Reluctantly I told Teddy that I wasn't ready to do more than one weekend a month. He said he understood and respected my decision, but the next two months it was obvious that he wanted more. Finally, he broke down and told me.

"Ashley, I know I've already asked, but I was hoping you'd reconsider spending more time with me."

It broke my heart because I knew I didn't have it in me.

Teddy continued, "I really like you. I don't want to be a weekend fling every month. I want a real relationship with you."

Tears welled in my eyes as he confessed his feelings to me. I wanted so bad to give myself to him.

I wanted to tell him "Yes...I'll be yours whenever you want me."

I wanted to tell him "Take me. Take me now and make me Ashley forever."

I wanted to take his face in my hands and smother him with all my love.

I wanted to give myself to him completely...but deep down in my heart, I knew that it wasn't possible.

I cried.

I broke down in front of Teddy and told him the harsh truth.

"I can't. I want to, but I just can't, Teddy. I'm so sorry. You deserve more, but I can't give it to you."

He pulled me into a hug.

"I know...but I had to ask."

The next part was even harder.

"I...I don't think we should see each other anymore." I whispered under my breath, almost hoping he didn't hear me.

He did.

"What? No! Why?" Teddy got animated as he jerked away from our embrace. "It's okay. I'm okay with one weekend a month."

"No you're not." I looked up at him, tears still filling my eyes. "You want me to be your girlfriend and I can't be that. I'm married. It's best that we just go our separate ways before this becomes even harder in the future."

"I'm willing to respect your marriage. I know you need your time with Victoria. Forget I brought it up."

"I know you are Teddy. And that's what makes this so hard. I love you. And that's why I have to let you go. You deserve better than what I have to offer."

That was four months ago, and not only was it the last time that I saw Teddy, but it was also the last time that I had become Ashley. Victoria still gave me my monthly pass to dress and explore that part of me, but I couldn't motivate myself to go through with it. I could no longer become Ashley just to prance around the house, and I couldn't go out without thinking about what I had given up with Teddy. I was trapped and I was depressed and it was starting to show.

Victoria stared at me as I played with my food. She could tell I was hurting. What's worse was that I felt bad that I was hurting her. I couldn't imagine how bad it felt seeing your significant other long for the love and touch of another person.

"You really need an Ashley weekend, babe." Victoria said.

"I've told you. I'm just not in the mood. I don't see the point anymore."

Victoria suddenly perked up.

"I think we've both been going about this the wrong way. We have both been trying to treat Ashley's woes by taking care of Aaron. Ashley had a tough break up. We need to take Ashley out and show her that it's okay and that she'll get through this."

I furrowed my brow as I looked up at my wife. "You make it sound like I'm bi-polar or have multiple personality disorder."

"Well, you have kinda been living two lives, and you completely cut off the one life right after experiencing a major life event. It hurts and you have never treated that hurt. You need to show Ashley that life goes on, not bury her under the pain."

I couldn't believe it, but what my wife was saying made sense. I couldn't put a bandage on Aaron to heal Ashley's pain.

"What did you have in mind?" I asked.

"Well, whenever we had a rough patch back when we were dating I'd go shopping, treat myself to a spa day, and then go out with the girls."

"I think I would be down for some shopping. Whenever I struggled with motivation to dress up in the past, shopping always helped to get me excited. "I don't know about a spa day though, and I certainly don't have any girlfriends."

Victoria considered my response for a minute. "I'll tell you what. Let's go shopping after work on Friday, and if you trust me, I'll set something up on Saturday for a spa treatment and a girls night. I promise that you won't be disappointed."

As much as I wanted to just wallow in my misery, some legitimate time out and about as Ashley did sound appealing. And Victoria was right, I needed some healing and a fun evening as Ashley. I had no idea what she was planning but I trusted her, especially after how she treated me when she caught me dressed the first time.

"Okay. I trust you." I said. "Make it happen."

The wait was only three days, but it drug on forever. It was excruciating waiting for Friday to come. I hadn't realized how bad I needed to be Ashley. I left work a few hours early to come home and get all cleaned up for the evening.

I was feeling a little edgy and my choice in outfit and makeup reflected it. I slid on a pair of gray, sheer to waist nylons and a black cable knit bodysuit. I paired those with a tartan mini-skirt and black Doc Martens boots. I wore my wavy, shoulder length dirty blonde wig and opted for dark eyes and pink, glittery lips.

Victoria walked in as I was putting on a studded bracelet and hoop earrings.

"Ahh, feeling a little rebellious, are we?"

I frowned. "Is it too much."

"Not at all babe. I like it," she said with a kiss to the cheek. "It's important to dress how you feel and you have every right to feel a little grunge. At least you can actually claim to listen to the music that started that trend unlike the kids who dress like that nowadays."

"I don't look like I'm trying to hard, do I?"

"The makeup is a little bold, but you've really gotten pretty good at it. It's not my style, but I'm impressed. It fits your personality."

I smiled at the compliment. For the first time in months I felt like myself again. Looking at my reflection in the mirror gave me a feeling of calm euphoria. It was almost like taking a drug. I was a new person both literally and figuratively.

"Let me just freshen up, and then we'll head out, okay?" Victoria said as she disappeared into the bathroom.

I couldn't tell you how long she was gone because I couldn't help but stare at myself in the mirror. I struck several poses and mentally noted what I liked and what I didn't. Victoria emerged and caught me red handed.

"Admiring the view?" She joked.

"It's been awhile. Trying to regain my feminine posture."

"I'm just teasing, Ashley. You look great. Ready to go?"

I loved that she called me Ashley. My heart already felt full as we left headed down to the car.

Mind if I drive?" I asked as we walked into the garage.

"Really?" Victoria questioned.

"Yeah. I never got to drive with Teddy."

"Okay, but only under one condition," Victoria stated. "That's the last time I want to hear about Teddy from you. We're getting you over him this weekend."

I laughed. "Deal."

I pulled out of the garage and onto the street. It felt empowering to behind the wheel as Ashley. Something about it made it seem more real and less like I was playing a part.

"To the mall?" I asked as I drove away from the house.

Victoria grimaced. "Uh, if you want. I had something a little more, how should I say, intimate, planned."

"Okay," I said in a long, drawn out syllable.

"Head into town, but go to Honey Birdette."

Victoria grinned as she turned to look at me.

"Really?" I asked. "Don't you think that's a little pricey?"

"Maybe, but I've always found that the best way to get over a guy is to look and feel your best. And what better way to start than with some ridiculously overpriced lingerie."

"Okay." I said. "I told you I'd trust you."

"Good." Victoria smiled her mischievous grin. "I think you'll find this very therapeutic."

In a short time we arrived and made our way into the store. Victoria had a few things from Honey Birdette, but I had never considered shopping there myself. In fact, the brick and mortor store was relatively new, as they had primarily been based out of their California location and online sales, so I was certainly excited to browse their in-store selection.

Just walking in, I was overwhelmed by a kaleidoscope of neon colors in meshes and laces of very high end lingerie. Everything I owned was pretty bargain basement. They were sexy, but I could never bring myself to spend so much money on something that I would wear so infrequently. The only thing that I had that could remotely be considered higher end was a Victoria's Secret Angel's Collection sequined halter bra, panty, and garter belt set. It was child's play compared to what I saw on the shelves here, however.

I immediately started to wander to a neon yellow bodysuit that caught my attention when Victoria called to me. She was speaking to to saleswoman.

"Ashley...c'mere." She said with a flick of her head.

I dutifully did as requested.

"This is Ashley," she continued as I walked up. "She is getting over a tough break up, so I'm treating her to something to help her feel herself again and get back on her game. Can you help her find something that brings out her inner beauty."

I was extremely touched by my wife's words. It was odd, but she truly cared for me as Ashley as if I were one of her best friends, and I certainly appreciated the intro. Despite my growing comfort as Ashley, I still tended to retreat inward and become shy when shopping.

The saleswoman frowned, introduced herself as Zoey, and pulled me in for a hug. I was initially taken aback because Zoey was a complete smokeshow. She was mid-20s, dressed in a short black skirt with an impossibly high slit and a tiny black suit coat that showed off her obviously fake breasts and neon red bra. I glanced at Victoria to make sure she wasn't upset that I was hugging this woman when I realized that she actually saw me as Ashley, not her husband.

That helped me relax.

Zoey released me and spoke.

"Ashley, you have such an amazing friend. I would be happy to help you release your inner vixen. Every woman needs to let her inner diva out from time to time."

"Thank you Zoey...and yes, Victoria is amazing, isn't she. A big thank you to her as well."

"So Ashley, I saw you looking at one of our wonderful bodysuits as you came in. Is that something that would interest you or are there other pieces that you would like to see?"

I smiled.

"Yeah, I love bodysuits. That and three piece sets make me feel the sexiest."

"We definitely have all of that. We have strappy, lacey, mesh and all in a wide range of colors from neons to pastels and even bolds or blacks."

"I really love your neon collections." I said with an impish grin.

"Everyone does." Zoey returned my smile.

"I also love mesh and straps."

"Okay, why don't you and Victoria have a seat and I'll bring over a few things for you to consider."

Zoey escorted us to a gorgeous sitting room where she took my measurements and then departed back to the front of the store. Victoria and I waited for her to return with some lingerie. In what felt like no time at all, Zoey appeared with several items in hand. She set them all on a table, picked up the first and started to show off her wares.

The first item, Zoey explained, was part of the Morgan Collection and was a three piece set in neon blue. The bra had a wide band under the bust, lace cups with a bold underwire and double shoulder bands. The panty was a hip hugger that had a wide waistband and two thin straps in a V-shape down to the crotch and a small panel of lace between the straps. The garter belt again had a wide band with smaller crossing bands with lace insets extending down to the garter straps. Zoey also showed that it could be paired with nude stockings with matching neon blue accents.

Victoria was thrilled. She nudged me with her elbow. "Imagine slipping into that. That blue would look amazing with your eyes."

Zoey agreed. "She's right. You would look amazing in this set, and I guarantee that you will feel amazing."

I finally spoke up. "I definitely like it. That blue just grabs your attention."

"Okay," Zoey continued. "I'll keep this one here for now."

The next set was called the Lottie.

"This is one of our bestsellers," beamed Zoey.

I could see why. It was a neon yellow set with thin bands outlining the bra, panty, and garter belt with surrounding nude mesh and inset with neon pink and orange floral embroidery. The mesh dominated the set and definitely didn't leave anything to the imagination. It too came with nude stockings with matching neon yellow accents.

"I love the mesh," I admitted, "but I'm not so sure about the thin straps. I may be a bit big for that."

Zoey admitted that it did not provide as much support as the Morgan, acknowledged my nod, and put it in a separate pile.

"I bet that would look amazing on Victoria, with her caramel skin tone though," I added, looking her way.

Her eyes were glued on the set.

"Yeah...I kinda want it!"

She paused, then lightly shook her head.

"But were here for you, Ashley."

Zoey continued with the next set. It was a bold turquoise set called the Jasmine and the style was just as bold as the color. The bra started with a neck collar that had a metal ring over the collarbone and straps that attached from the ring to the shoulder straps. The underbust strap was wide and supportive, but the cups were a smooth and shiny satin that only covered the bottom half of the breast. To cover the nipple, the bra had two thin, buckled straps that went from the cup to the shoulder strap.

The garter belt had matching buckled straps around the midsection and down the garters. The panty was a high waisted, full coverage front with a thong back with matching buckled straps around the waist, another metal ring, and mesh coverage.

"That's powerful." I exclaimed.

"Hard not to feel dominant with all these straps." Zoey added. She held the bra and panty up to herself for effect.

"I love it, but I still think I like the Morgan the best so far."

Zoey put the Jasmine with the Lottie and moved on.

"The last two things I grabbed were bodysuits I think you'll love. The one you were looking at when you came in is called the Christine."

Zoey held it in front of her as if she were modeling it for us. It was the same color and pattern as the Lottie, neon yellow bands with nude mesh and pink and orange floral accents. I could feel myself sliding my legs into the openings and pulling the sexy, sheer material up over my body.

I was in love.

"I can see that you like it," Zoey said.

"I do. It's amazing."

"I'll put it with the Morgan for now." Zoey continued. "The last bodysuit is the Laura."

She held it up just like she did with the last. It was the same color blue as the Morgan set and had similar bands under the bust and around the waist. It also had blue mesh inserts over the abdomen and down the sides and back, but had nude mesh inserts, with matching floral embroidery over the breasts and down the front, separating the blue mesh pieces.

"I like it, but it's no Christine." I admitted.

Zoey nodded and placed it with the Jasmine and Lottie.

"I'll leave you and Victoria to try them on if you'd like. Just use one of the disposable panties underneath the garments and throw it away when you are done. I do have some more items if you'd like to browse, but this is what I have in your size that matched your preferences"

I thanked Zoey, who then left Victoria and I to study the things she had chosen. Once she was gone, I handled the lingerie like each item was a rare and treasured piece of artwork. With my eyes closed, I felt the silky smooth fabric and imagined myself wearing each set.

Victoria broke my trance. "Are you just going to feel them, or are you going to try them on?"

I smirked. "I'm going to try them on. Just wanted to enjoy the tactile touch of the fabric by itself for a minute. And thank you, by the way. I am really enjoying this."

I undressed and started with the Morgan. It looked as good on me as I had hoped. Just like Victoria had suggested, the blue material made my eyes pop with a little something extra. I didn't have the stockings to try with it, but I could only imagine that they would put it over the top.

Much to Victoria's disappointment, I did not try on the Lottie or the Laura. They were very nice pieces, but just didn't feel like me. I did however try on the Christine bodysuit. It felt heavenly and hugged all of my curves in the right places. The mesh left a lot of me exposed, but I couldn't help but smile as I stared at my reflection in the mirror.

"What do you think?" Asked Victoria.

"I like them both. I can't decide."

"Which one feels more you?"

AshRynn87
AshRynn87
709 Followers