Allowing Jill to be free (Patreon)

“Oh my, I have so much to do today," said my wife, Pamela Mead as she walked into our kitchen, "I'm meeting Brian for lunch and then we have to pick up Lily at the airport.”

I had to smile. I love my wife, but she is about as organized as a class-three hurricane. I put down the wedding album I had been perusing and grabbed her by the shoulders, holding her in place. I kissed her deeply. I have been using this method to calm Pam down since we were teenagers. It always works and it's fun. "You are meeting Lily for lunch and picking up Brian from the Airport,” I clarified, holding her gaze.

Pam sighed, “Right.”

“Do you need me to pick up Brian?” I offered for the umpteenth time.

“No. I’ve got it,” said Pam as she walked over and sat on my lap. She put one arm around my neck and started to rub the back of my neck. "You do so much already. Besides, I am going to need you to prepare the padded room and the deprogramming machine."

I put my arms around her waist and chuckled, “come again?”

"Our son just spent the whole summer with his Aunt Alice," Pam rolled her eyes, "Lord knows what she let him get away with."

We both laughed. She turned a couple of pages in the wedding album and stopped on a shot of just us. I was wearing a classic black tuxedo and she a tiered wedding dress. “You looked so good in that dress,” I complimented her.

She kissed me on the cheek, then said “It would have looked better on you.”

I closed the album and stood in a huff. She slid off my lap and stood as well. She was always so graceful. “What?” Pam asked.

“You know what,” I responded, a lot louder than I meant to, “No more dress up.”

“But why?” She asked, moving close to me.

“You know why,” her look said she didn’t. “The kids.”

"Oh, for heaven's sake," Pam said, throwing up her hands, "Bill, they love you. Do you really think they would care?"

I thought for a minute before answering. “I’m protecting them.”

“From who?” Pam asked.

“The world.”

"Bill," Pam said in her mom's voice, "Lily and Brian are teenagers now. Lily will be off to school next year. They can take care of themselves." Pam then went on, “I know why you stopped being Jill, Bill. I get it. I don’t agree with it, but I get it. But I also remember how much fun it was to play dress up with you when we were kids. Alice enjoyed having Jill as her babysitter and mom and dad loved having another daughter. I fell in love with both of you. I knew when I married you, Bill, that I was, in a way, marrying Jill too."

“I just can’t,” I said sticking to my guns, “If they got called names or worse were embarrassed because of me being Jill…I just couldn't take it. Your right, they're strong but I'm not. I'm a coward."

“Oh, sweety,” Pam walked over to me and used a paper towel to dry my eyes. “Please don’t cry,” said Pam, beginning to tear up herself.

“Can we talk about this later?” I asked, trying to end the conversation.

Pam opened her mouth to argue, but then her phone beeped. “Crap,” Pam exclaimed and kissed me on the forehead, “Got to go.” Pam walked to the doorway, then turned back to me and said, “please think about Jill.” She took a deep breath and said, “Wish me luck.”

“Break a leg,” I answered back.

What Pam didn’t understand was, that I had been thinking about being Jill every day for the last 18 years. I imagine it’s the same for a recovering gambler. They never stop hearing the sound of poker chips falling or the whir of the slot machine. I thought about silk stockings and lip gloss constantly.

When Lily and Brian were younger, I only thought about being Jill every once in a while. There was so much to do. Pam and I were working full-time. The kids had school activities and clubs. We did everything we could to be part of the kids' lives. I didn't want to be the workaholic parents that mine were.

Over the years my resolve to not cross-dress eroded very slowly. Then two years ago it was as though the universe turned against me. The kids started doing stuff on their own, with their friends, and not with us. I started working from home. Pam, however, still had to work in the office, leaving me alone for most of the day. This provided me with means, motive, and lots of opportunity.

I went up to the bedroom I share with Pam and directly to our (shared closet-delete. You already said 'shared'). “What am I doing?” I asked myself.

Of course, I knew exactly what I was doing. Pam permitting me to be Jill again had destroyed the last of my resolve. I moved several “Jill” dresses into our closet a year ago. The best place to hide things was in plain sight. I found a little knee-length red dress with short sleeves, a white belt, and a keyhole high neckline. "Hello, old friend," I said to the dress.

I pulled out the dress and laid it out on the bed. I then found a set of nude thigh highs. It took me a minute but I finally, found a set of black lacy panties and a matching bra. I added them to the growing pile on the bed. Next came a set of black Mary Jane's with a one-inch heel.

Finally, I went down to the kitchen and got a step stool. I had put my breast forms, hip forms, and wig in a box on the top shelf in the closet. I pulled the box out and started down the step stool. I miss judged the last step and fell on my backside. My wig stand popped out of the box and hit my nose on the way to the ground. “I guess I deserved that, for neglecting you for so long,” I said to the head-shaped stand.

I had showered and shaved that morning. I had not plucked though, so I went to work. Next came foundation, concealer, blush, and eyeshadow. A small dab of perfume went behind each ear. I don’t want to say it was like riding a bike, but in a way, it kind of was. In less than thirty minutes Jill was staring back at me from the mirror. “Hello, beautiful,” I said to my reflection and then blew Jill a kiss.

My girly juice began to flow by this point. I put on the panties and the bra. I put my size “C” breast forms in the cups and shimmied into my hip pants. The stockings felt so good against my hairless legs. I just had to lay there, on the bed, enjoying the feeling of nylon and spandex. I asked the room at large, “Why did I ever stop doing this.”

I put on the shoes and the dress, remembering all too well what a pain a zipper in the back can be. Then I put on the wig, brushed it out, and put it on. I ran back to the closet to grab a headband that matched the belt of the dress perfectly. I finished off the outfit with a string of pearls.

“Hey Alexa,” I said, “Play, Just a Girl”

There was a chime and Gwen Stefani started to sing, "Take this pink ribbon off my eyes." And I started to dance, badly. I grabbed my phone off my dresser and started taking selfies. I was debating whether to send one to Pam when I heard a voice say, “Hey Alexa. Stop.”

I turned and came face to face with my son Brian.

“Brian! What are you doing here?” I asked automatically.

“I live here,” Brian said, obviously a bit confused. “Who are…” he stopped speaking when he looked into my eyes and saw that they were the same as his. “Dad?”

“I know that, Brian,” I said exasperated. I struck a womanly pose, putting one hand on my hip, “But your flight doesn’t land for four hours.”

“I got an earlier one.” Brain explained as he orbited me like a moon. “Then took a cab home.”

“Does mom know about this?”

As if on cue, my phone blinged to indicate an incoming message.

“Does mom know about this?” Brain parroted me with a smile.

"Yes," I said, taking a deep breath to calm myself. I don't know why, but it was way easier to remain calm dressed as a woman. "Do you want the whole story or the short version?”

Brian sat on my bed. “Short version. For now.”

“Your mother and I used to play dress up when we were your age.”

“She called you Jill,” Brian interrupted.

I covered my shock at him knowing my secret name with bravado, “You telling this story, or am I?”

“Sorry,” he answered looking contrite.

“Grandma and Grandpa Mead hired me to take care of Aunt Alice after mom when to college. They didn't mind me dressing like a woman so I pretty much lived as one for several years.”

“Gram and Grandpa know?” Brian exclaimed, nearly falling off the bed.

“Yes.” I walked over and sat next to him, “they supported and still do support me just like they support you and Lily.”

“What about your mom and dad?” Brian asked.

"They know, but like with everything else, they don't care, one way or the other."

“Jerks,” Brian said and then looked at me a little worried.

I tussled his hair and smiled, “A fair assessment of my parent, if ever I heard one.”

Brian looked at his feet and asked anxiously, “Do you like dressing like a girl, I mean a woman.”

“Very much.”

Brian looked puzzled, “Then why don’t you dress like this all the time?”

“Because, this is something different, and this world loves to hate anything different." I kissed the top of his head, being careful to not leave any lipstick, "I have you and your sister to worry about. I didn't want you to get picked on or harassed."

“So, you’re giving up something you love for me and Lily?” Brian asked.

“I’m giving up something I love for two, some-ones I love far more," I answered beginning to tear up.

Brian got up and brought me a tissue. “You know you don’t have to do that. I mean I can take care of myself and I know Lily can too.” Brain looked a little nervous, “Besides, you’re really pretty.”

I blushed. Brian did too. "I mean it, dad," Brian went back to looking at his shoes, "If you want to keep dressing as Jill, I will support you and I know Lily will too. Especially if you show her how to shade her makeup like that," he pointed to just above my eye.

“What makes you think that?”

Brain looked worried, “I may have heard her say something about it to Aunt Alice, once.”

At that moment We heard the front door open and Pam and Lily call out, “We’re home.”

Brian pulled me to my feet, and with a grin that would have made the Cheshire cat envious said, “come on. Let’s go introduce Lily to Jill.”

He began to pull me out of the room. I pulled back and made him look me in the face, “Who told you about Jill?”

Brain looked a little sheepish, “Aunt Alice.”