Becoming Ashley

How did I get here? Not here in the world, but here in this point in my life. This wasn't what I had imagined. This isn't the way it was supposed to go, is it?

Here I stand, a man dressed as a woman, quite convincingly I may add, as another man passionately plants a deep kiss on my lips. My wife stands off to the side in utter shock, eyebrows raised and jaw agape. What decisions led me to this point? Could this have been avoided, or was this always the road I was meant to travel? Do I give into my impulses and allow this to continue, or do I put a stop to everything right now, blowing my cover as a crossdresser and facing the consequences?

To get these answers, I guess we'll have to go back a few weeks to when this all started; back to when my wife Victoria caught me dressed in women's lingerie. In all truthfulness, I guess this all started when I was a young boy and decided that I wanted to see what it felt like to wear a pair of women's stockings. Over the years, that developed into full on crossdressing, including lingerie, outfits, wigs, makeup, and a collection of heels that rivals that of my wife.

Normally, I was very safe about my crossdressing. I had been closeted about it for at least 15 years, and I always made sure that I have several hours of free time with my wife out of the house before venturing down that path. That gave me the time to grab all of my things out of storage and enjoy a little time dressed in the chosen outfit. It usually wasn't sexual, I just enjoyed the feeling of the transformation from man to woman, although sometimes I would get myself all turned on at the sight of the woman looking back at me in the mirror.

I am six foot and about 170 pounds; a little large for a woman, but average sized for a man. I have a trim athletic build, nice legs, and a bit of a booty. So with a little bit of shapewear, I'm able to pull off a convincing woman, albeit a tall one, especially in heels.

On this particular day, my wife had run out to get lunch and do some shopping with a girlfriend. She told me that she expected to be gone for about 3 to 4 hours. It was tight, but it would be plenty of time to get an hour dressed as my female persona, who I called Ashley, and still have time to clean up all the evidence before Victoria returned. I had put on my 38DD breast forms and gotten my wig and makeup all to my liking. Just as I pulled on a pair of tan stockings to go with the green bra, panty, and garter set that I was wearing, my wife burst through the bedroom door.

I don't know which of us was more shocked, but I froze like a deer in headlights, unsure of what to say or do. Victoria, in her initial shock, thought that I had another woman in the bedroom.

"Who the fuck are you?" she started to say. "Wait...Aaron? Is that you?"

I was frozen stiff. Unable to respond, yet too afraid to run away. I was busted.

"Oh my God," she laughed. "What the fuck are you doing?"

"Um, what are you doing home?" I finally uttered out, sheepishly.

"Well, I had almost gotten to the restaurant when Holly called and said she had something come up and wouldn't be able to make it, so I came home to see if you wanted to join me for lunch." She laughed again. "But it looks like you already have plans."

"Victoria, I'm so sorry. It's not what it...well it is, but...I don't really know what to say." I stumbled about my words, unsure of how to explain this shocking sight to my wife.

I took off the wig and began pulling off the stockings and lingerie, uncomfortably aware that my wife was watching me like a hawk.

She cocked her head, intrigued, but clearly confused by the situation. "I didn't know you had this side of you Aaron. I mean, I have several questions, but I can't help but notice how nice your legs look. You honestly had me thinking you were a woman until I saw your garish makeup."

I frowned. "Yeah, I'm not so good with the makeup. Lack of experience I guess."

I paused, unsure of how she was taking this. "I'm confused, are you pissed?"

Victoria still stood there, eyeballing me as I removed my breast forms.

"I'm not exactly sure," she said. "First off, is this just something you do, or were you about to meet with someone? Are you gay, or trans? Are you looking to transition to female permanently? And how long has this been going on? Looking at your suitcase full of clothes and shoes, I'm guessing it's been happening for quite some time."

I did my best to explain and answer all of her questions, and to her credit, she remained quiet and listened. I'd told her that it started when I was young, well before we had even met, let alone got married. I had always figured it was a phase I'd eventually grow out of, but instead I only traveled deeper and deeper into the rabbit hole.

We discussed my affinity for women's fashion and shoes. She admitted that she did find it weird that I always knew the perfect shoe for her outfits whenever she was getting ready. I showed her my entire collection of clothing, shoes, lingerie, stockings, and of course makeup and accessories. Finally I showed her my several pairs of breast forms, hip pads, cinchers, and other shapewear. It was actually quite a relief to finally get all of this off my conscience.

She finally breached the subject of my sexuality again. "So, what does all this mean? Are you gay, bisexual, trans?"

I just shrugged. "I...I don't really know. I can tell you that I'm not gay. I mean, I don't have any desire to be with a man, as myself or my female personality. And I love women, maybe too much. Perhaps that's why I enjoy being one."

She smirked, "Have you ever played with a dildo?"

"No!" I blurted out, maybe a little too aggressively. "No, but I guess I have thought about it."

Victoria just pondered my answer in silence.

"I...I have put a finger inside though. I didn't not like it."

Perhaps I said too much. Victoria continued to stare at me in silence, but at this point I couldn't stop myself from talking.

"I've also talked with other crossdressers and trans women on social media, like Reddit and Kik. I guess I find them attractive. But I've never looked for a hook-up, I promise." I continued to ramble on nervously. "It's always just been to share and get tips from others like me. Again, I'm so sorry."

Victoria finally broke her silence. "No need to be sorry for being who you are. I mean, I wish you would have been honest with me from the beginning. I'm hurt that you felt you couldn't trust me with this."

It just occurred to me that she now had dirt on me. Dirt that I did not want getting out to my family, friends, and coworkers.

"Victoria, please...you can't tell anyone about this." I stammered.

She just shook her head. "Why would I tell anyone? It obviously took a lot of effort for you to confess all this to me, even though you only did it because you were caught red handed. I'm still your wife and I will keep all of this in confidence."

"Thank you," I pleaded.

"But," she said defiantly. "I don't want you sneaking around and lying to me anymore. I can deal with your alter persona, but I won't tolerate lying. I have always been honest and up front with you, especially when it comes to extramarital sex."

I just nodded in shame. She was right. She had always been honest with me. It was me who drove us to an open marriage. More accurately, it was me who practically begged my wife to have sex with other men. It was always my fantasy to watch her fuck another man. It took a lot of reasoning and pleading, and it almost destroyed our marriage, but she finally graced me with the experiences I craved.

Victoria had always been up front about what she expected from me and what she planned with other men. She would always tell me when she'd receive a proposition from another man, and it would always be a unanimous decision on whether or not she would accept. Sometimes I got to watch, and sometimes I would just hear about it the next day, but if one of us said no, then that was it...no questions asked.

I felt even more shame for keeping my true self from my wife.

"You're absolutely right," I admitted. "I've been selfish. I won't keep anything else from you."

Victoria smiled. "Great! I've got just one last question for you. Have you ever gone out as...um"

"Ashley," I informed her. "Ashley Ryann, actually."

"Ashley, huh? I like that. Have you ever gone out as Ashley, or do you just hang around the house?"

I slunk back into the bed. "No, never. I've always been terrified that someone I know might recognize me. I considered staying at a hotel out of town and going to the bar as Ashley, but I could never bring myself to do it. Besides, like you said, my makeup is garish."

Victoria grinned, "I could easily help you with that."

"Really?" I beamed. "I would love that."

I couldn't believe how this was turning out and I couldn't believe how accepting my wife was being. I would have told her years ago if I had thought this reaction was even possible.

"Of course," Victoria continued. "Actually, that really may help me out with something I've been meaning to ask you about."

She had my full attention now. "Really? What is it?"

She sat by me on the bed. "Well, you know Mike from my office right?"

I knew Mike alright. He didn't know about our open relationship, but he knew that Victoria was married. That didn't stop him from coming on to my wife every chance he got. It actually bordered on sexual harassment.

In fact, Victoria had often told me about his advances on her. She always loved the attention, but she was usually put off by how forward he was. She described him as a frat boy, only after as much pussy as he could get his hands on. Every woman was just a conquest to him, whether or not she was spoken for.

"Yes, I'm aware of Mike," I responded. "What did he do now?"

"Well, you know my feelings about him, but he keeps pestering about going to this new bar in the city with him. He wants to take me and wants me to bring a girlfriend for his buddy."

Taken aback, I spit out, "And what did you tell him?"

Victoria shrugged, "I told him no, of course. But if you were to go as my girlfriend, I think that might be fun."

I couldn't believe what I was hearing. Just an hour prior I was afraid that my marriage was over, and now my wife was suggesting taking me out on a date as my female persona. On top of that, she'd be on a date with a guy she had always claimed to hate.

"I'd love to go out with you," I said eagerly. "But I'm not interested in dating a guy. Besides, I thought you couldn't stand Mike."

"To be completely honest, you're right. I can't stand Mike," Victoria admitted. "But a little birdie told me that he's hung, and I figured if it's just sex, then what's the harm? As long as you approved, of course."

I just sat there stunned. I wanted to go out as Ashley, but I wasn't too keen on the idea of being on a double date. Also, I never really cared who Victoria fucked, but I never thought she'd want Mike. I was completely caught off guard.

"If we did this, I wouldn't fuck him on the first date. I'd be right by your side all night to make sure you were comfortable. If at any point you wanted to stop, we'll leave and call it quits." Victoria did her best to calm my fears and reassure me.

"I don't know. I just don't think I can do it," I admitted. "I'm sorry."

Victoria didn't let up. She just changed her tactic.

"How about this? How about you get dressed back up as Ashley and I'll help you with your makeup. Then we'll go shopping...you can take Holly's place. We'll buy you an outfit or two. Just to get you comfortable as Ashley in public. If you still don't want to do the double date afterwards, I'll drop it."

"Right now?" I asked, incredulously.

"Yeah, right now." She was practically begging me to join her as Ashley.

How could I turn that down. A chance to finally present myself as Ashley to the world, and a shopping trip with my wife to buy clothes for me. I was practically floating at the prospect.

"Okay," I said eagerly. "Where do we start?"

Victoria eased me into it gently. "Why don't you pick out an outfit to head to the mall, and once you're dressed, I'll do your makeup and give you some pointers."

I sprung into action. So many options. I had never actually picked an outfit for me to venture out as Ashley. Most of my clothes were sexy and a tad slutty. What would I wear to the mall?

I put the lingerie set away and grabbed more modest undergarments; a black mesh bra and matching thong. I also grabbed a pair of black sheer-to-waist tights. I worked my way back into the breast forms. It was a full vest version that I had to pull over my head. It went from mid-neck down to a few inches below the breasts and covered my shoulders as well.

I threw a small pair of hip pads in the tights to help with my figure. I had several pairs, but opted with a more realistic version, rather than some plastic fantasy. Finally, I put on a modest maroon colored dress. It was a U cut neck, but it was high enough that it didn't show any cleavage. The hem was knee length ansent, had a panel of lace and a tie up the left leg. I topped it off with a black choker to hide the transition from breast plate to skin, and then threw on a pair of black ankle boots with a 4 inch heel.

I normally wore a long, bright red wig. It was my fantasy look and I loved how it highlighted my face. I resigned myself to a wavy shoulder length dirty blonde wig, however, as I was too afraid to draw attention to myself at the mall.

Once I had my outfit in place, I turned to my wife. "How do I look?"

"I love it!" She beamed. "Now let's work on that makeup."

She took my hand and walked me to the bathroom. Victoria said that I had actually done a really good job on the foundation and the contouring, but I really messed up the eyeliner and eyeshadow. She also said that the bright red lipstick was a little too aggressive for going to the mall. She fixed me up with false lashes, a smoky eyeshadow, and a flawless liner with a wing. Victoria topped off the look with a soft pink lip gloss.

"There," she said. "I wouldn't know you from Adam. You look amazing. Have a look," she said as she motioned to our full length mirror.

I just gawked at the woman that stared back at me. I always thought that I had done a pretty good job in my transformation, but with my wife's help, I finally felt like a complete woman. Of course I still sounded like a man.

"I'm in love," I admitted. "But you'll need to help me with my voice."

"We can work on that a bit in the car, but I wouldn't stress it too much just yet. We live in a trans friendly town, but you'll definitely need to soften your tone. I can help."

I couldn't believe I was about to head out of the house. The butterflies in my stomach were relentless. Normally I could work a six inch platform heel like a professional dancer, but I felt wobbly in my chunky four inch boots.

Victoria smiled at me and took my hand. "Are you ready to introduce Ashley to the world?"

"I guess no better time than the present," I answered.

She led me to the car. I got in on the passenger side and she drove us to the mall. It was probably for the best. While I was comfortable walking in heels, I had never driven. On top of that, I needed to focus on my voice.

It was a short drive, but we made good progress. She helped me to raise my pitch without sounding too fake or breathy. It still sounded weird to me, and I had to focus really hard to not lose character, but it was better. We sat in the parking lot a few extra minutes to work on it before I finally built up enough courage to finally step out of the car.

"Are you ready?" Victoria asked.

I gave her a quick kiss on the lips. "Let's do it. Thank you for this. I really appreciate your understanding."

My wife just smiled back and watched as I stepped into the world for the first time, born anew. I waited, and she eventually joined me at my side and walked with me into the mall. At only 5'5", I towered over Victoria, especially in my 4-inch heels. I felt like every single person that we passed was staring at me and could see right through my charade. Victoria sensed my apprehension and reached out to grab my hand.

"You're doing great," she whispered.

"I feel like every person here is pointing and laughing at me," I said shakily.

Victoria reassured me. "Of course you do. You are way out of your comfort zone, but I promise, hardly any one is looking at you, and those that do only see an attractive woman."

"A gargantuan woman," I corrected.

She sighed, "There are plenty of women that are taller than you babe. Just relax. Let's head into Akira and find you something cute."

Victoria knew exactly how to calm my nerves. She had never spent any time with Ashley, but it was like she had known her her entire life. Focusing on the clothes helped me to take my mind off of everyone else, and what girl doesn't like shopping for herself.

We perused the whole store and found a few dresses and skirts in my size that I thought were sexy, but wasn't committed to. Finally, I came upon a tan bodysuit made of sheer mesh. It was just a few shades darker than my skin tone. It was sheer enough that it would show a bit of cleavage, but still opaque enough that I wouldn't be completely on display. Finally, it had a zipper front that would allow me to show off my ample, albeit fake, chest.

"This is it!" I squealed.

"That's hot," Victoria agreed. "Why don't you go try it on?"

"Try it on?" I was confused. "I've never actually tried anything on in a store before. I've always just brought it home and hoped it would fit."

Victoria laughed. "Well, that's the benefit of being a woman. You can actually use the women's fitting rooms and see if an item fits you BEFORE you buy it. Here, let me grab a saleswoman."

She flagged down a worker who helped me into the fitting room and complimented me on my dress. I was all smiles.

I put on the bodysuit and a short black skirt that I thought would compliment it nicely. It cut to mid-thigh and had an aggressive slit up the right side. It was actually kind of slutty, but it was definitely my style. I looked at myself in the mirror and fell in love all over again. I peeked out from behind the curtain and called out to Victoria.

"Pssst, Victoria...come take a look."

She joined me in the fitting room.

"Wow! You look amazing in that. Definitely shows off a lot of leg though."

I frowned. "Is it too slutty? I was thinking about wearing some nude fishnets and a pair of shiny ankle boots with it"

Victoria pondered the outfit. "No, not TOO slutty, but it definitely shows off your goods..."

She paused.

"I'm sorry, I can't stop staring at your legs. Who would have thought my husband was hiding stems like those?"

"Shhh!" I quieted her. "Don't give me away."

I made a quick peek out of the fitting room to make sure no one was within earshot.

Victoria grimaced. "Oh my God, I'm so sorry. You look great Babe! You should totally get it."

I nodded. "I think I will get both the bodysuit and the skirt. The bodysuit is a must. If the skirt feels too short, I have some longer ones that will work as well."

I changed back into my clothes and headed over to the shoes while my wife continued to look for a dress for herself. Most of the shoes were quite exotic; neon colors and straps galore, but I was able to find what I was looking for. They were almost perfect; a glossy, patent leather ankle boot with a side zipper. The only issue was that it was a 6-inch platform. I tried them on and strutted around the store. They fit like a glove.

I heard a voice from behind me. "You absolutely have to get those."

I hastily turned to see the woman that helped me into the changing room, but was too startled to respond.