My wife was working and wouldn’t be back until 6 and Amy, 17, was to be over with friends until after five. When I took the time to cross-dress. I had done some makeup and even brushed my hair into a more feminine style. I had put on some pantyhose and a matching bra and panty set. I had put on a smart-looking knit dress and a pair of three-inch heels.

I looked in the mirror to see how I looked. It was then that I spotted Amy peeking through the door. When our eyes locked onto each other she pushed the door open. “Daddy, I didn’t know you had this pretty side to you!?”

I could have died at that moment with all kinds of fears and questions arising. A thousand thoughts flying through my brain… (What have I done to my daughter? Liz is going to kill me? I promise I’ll never do it again. Daddy has a dress-up party to go to, and I…)

Amy just came in and sat on the bed, and waved her hand for me to turn around. I turned to face her and she smiled saying, “You actually look good as a hip mom. How much did mom have to help you?”

The surprised look on my face must have given me away. “So Mommy doesn’t know about this time, or are you saying she doesn’t know?”

I said, “I thought you were supposed to be at Sheila’s this afternoon?”

Amy said, “I’m sorry to disappoint you. How about you answer my question?”

“Your mother knows, but you aren’t supposed to.”

Amy smiled, “So does this mean your bacon is fried?” She giggled at her own humor.

I said, “Why don’t you get out of the room and close the door, so I can change back?”

Amy said, “I have a better idea. We can go downstairs to have some tea and cookies, so we can talk.”

I asked, “Don’t you find this awkward and want it over with?”

“Daddy, this is 2021, not 1984 or whatever. There is no way I want this over until you tell me what’s up. So let’s go downstairs. You should be happy that you look this good.”

We started downstairs and I had Amy go in front of me. But she hurried down so she could watch me. “You don’t do too bad for wearing heels.”

I asked, “Do you really think so?” I was used to heels and had forgotten I had them on.

“It’s nothing that with practice, Mom and I can’t help you to improve on.” She smiles at the idea of helping me. “How often have you gone out like this with mom? I could see Mom having fun with you like this.”

The hot tea water is steaming as Amy puts a tea bag in each of our cups. “It’s red raspberry with things good for us women. We drink it when Mom and I relax to talk.” Instead of several cookies each, there’s one cookie for each of us.

Amy asks, “So are you one of those guys who felt like a girl since you can remember?” I was surprised she asked such a question.

I asked, “How is it that you ask such questions?”

“Dad, I don’t want to keep saying it but this isn’t the old days. We have computers, the internet, and learn more at school. Girls like to surf and look up things too.” Amy sat back and smiled. “You’re cool. I don’t even see you sweating this?” I was more nervous than she knew.

I am stunned in hearing my wife’s car pull into the garage. I quickly stand and Amy steps in my way. “Mom knows that’s why she is home early.”

I turn and see Elizabeth come through the door. Her look is stern but softens as she sees Amy blocking my exit. “Amy’s right, you do look good for not having the needed time… Did I not tell you that you’d get yourself caught?” She poured herself a cup of tea and Amy and me some more.

I was uncomfortable in sitting down, but took correction and sat up and put a hand in my lap. The other two chat away; I feel like it is at my expense but I am too embarrassed to say anything.

My wife finally says, “Well, if the three of us are going out to eat you need to make sure your five o’clock shadow is not a problem.”

We go to our room and I begin to undress when Liz says, “Don’t change just shave and redo your makeup. We’ll go to the Purple Goose this time it will be okay for Amy. Especially now that she’s seen you; the others won’t look that different.”

I’m set to argue, but Liz and I had agreed how we’d not try to cover over it and face this my issue.

Once I’m shaved she asks me, Please, let me do your makeup. I don’t want you doing too much. And if Davis is there and asks you to dance. I don’t want to make a scene. Dance with him once and then we’ll be going.”

Kenny Davis is a friend who noticed makeup on me once and said I owed him a dance if he sought me out. Kenny is a gay man and a good friend of the family.

I planned to do my makeup and then complain it didn’t look good enough for me to go out. But Liz had outdone herself and I was caught off guard to find myself being attractive. Liz handed me a purse saying, “Your keys and wallet are already inside thanks to Amy.”

Amy chirped in, “I even put in some extra makeup and your lipstick.” Liz’s car was in the way, but she went to her passenger side door. I was either driving or sitting in the back, so I chose to drive.

We were able to park near the Purple Goose and were soon inside. Being three women drew some attention, but Cassidy was soon over to seat us. She quickly recognized Liz and Amy but took her time looking at me and trying to draw a name. It was Liz who was quick, “This is my other half playing house, Lindsay says hello.”

I went to a softer voice, “Hi Cassie.”

She showed us to a table, gave us menus, and took some time to chat. “Can I ask, Liz, if you did her makeup? It’s too good for an evening out for Lindsay doing it herself.”

Once Liz asked for their pork chops I knew we’d be there longer. It would be after 7:00 before we’d be served. The crowd even then was a mixture of couples and singles, straight and LGBT. Then it was our salads and rolls and Liz ordered us a carafe of wine. One glass would have been fine, but with the second Liz handed her set of keys to Amy.

It wasn’t until after 7:30 when the Johnsons came that Amy got their attention. Aaron Johnson joked with me, “You know, we like coming here, but my wife would never let me out like that?”

Amy said, “Layla, I hope you and I can talk later.”

Layla said, “Don’t get shook, but my parents are here for me, my mom can go both ways.”

Once they went to their own booth Amy began to talk. “I wonder, what she thinks about me. I’ve hung around with her and some of her friends but I didn’t know this about her.”

We were quite relaxed and nearly finished our drink when Cassie brought over a Grasshopper split for Liz and me. Cassie said, “This is on me, I wanted to celebrate your first time here. I’m proud of you Liz and you Lindsay for being comfortable. And to you Amy, ‘Goes the evening’s tip for being the safe driver.”

Mom asked, “Cassidy if you have time for a dance and can find a partner for Lindsay, I’d like a time with you.”

Cassie called, “Kenny, I think you got your wish.” Kenny Davis was soon there.

I looked to Liz and whispered, “I didn’t see him come in?” She whispered back she had. Kenny was taller than me even with two-inch heels. It was awkward, but I was glad we were not snug together. Kenny came over after the dance. “Amy, last year I saw Leon, your dad, at a barbecue and he had missed some makeup and finger polish, so I knew.”

Amy said, “Like you, I’ve noticed things before. I’m surprised that instead of making me sick; it’s kind of cute that he’s a chick. Today I was successful in catching him. I’m not used to it, but I’m glad, Mom and Dad are not in denial of it… Have you two ever been together before?”

Kenny said, “Heaven no, we haven’t. And your Dad probably is not gay, but a crossdresser or trans. I’ve always appreciated you for folks for being open. I know they’ve raised you the right way. Take your time in coming to know this side of him.”

Kenny squeezed Leonard’s hand, and then asked, “Could I give you a kiss?”

I hadn’t taken him seriously until he leaned forward and I found myself puckering my lips and closing my eyes. It was a light kiss but he pressed forward until I responded. He hugged me, and I held him as he whispered. “Maybe some time, we can meet?”

Amy and I were sitting when Erik Handsome brought Liz back from the dance floor. She joked, “It is nice to be treated nicely by a man. If you have a friend, maybe we could double date.”

Amy said, “Mom you’re being mean.”

Her mother said, “I love your Dad; he has his manly side. Maybe now I’ll even get to adore his soft side some more.”

Liz says, “You know what could have been a terribly awkward evening has turned out rather nice. I would like to have a dance or two with you before we call it a night.” We danced and Liz was at ease with Lindsay.

The second dance was faster and they appeared as one of several women couples dancing together. It was the next slow dance when they saw Amy dancing with her friend Layla.

While I was wanting to get home, Amy began talking, “Mother have you ever danced with another woman and experienced both of you had hot breasts?”

Elizabeth, gulped and asked, “Amy are you okay? Are you indicating that happened while you were dancing? I’m surprised you didn’t stop dancing and walk away.”

“Mom, it wasn’t like it was bad; I was just surprised. It felt good dancing with her, she’s a friend,” Amy said.

Liz said, “Maybe it’s a good time to be going home?”

Amy spoke saying, “But Layla had talked about another dance. I don’t want to go home because of me.” Her mother asked if she was sure. Amy nonchalantly said, “Sure it’s not a big deal; I don’t want to discount my friendship with Layla or have it be seen in a bad light.”

Liz looked at Leon, don’t act too surprised but Mel Stott’s is on his way over here with Erik. If there’s going to be dancing; I’ll be with Erik again. Remember, you’re the one who wanted to practice being a woman.”

Mel extended his hand to Leon and said, “I hear you’re Lindsay for tonight. I guess if your game to come out so am I?” Mel tried to swing me like we were going to do an old boogie type of dance, but I didn’t know-how. He ended up drawing me close and we ended up moving our hips in rhythm together. I was glad when the dance ended but didn’t move quickly enough and got drawn into another slower dance.

Then it was another dance with Kenny and two others I didn’t know. I found myself distracted at the end of each dance looking for Amy or her mother.

It was after 10:00 when I finally got a break as I needed to go to the bathroom. Kenny told me to either go home, use the women’s room, or that I would be propositioned in the men’s room.

I barely made it home, when Liz dared to tickle me as I went to use the toilet. I had wet myself before getting there. I used the toilet, and Liz said, “You can take off your pantyhose and change panties, but no more than that! We need a family discussion!”

I wasn’t happy with the panty brief, she handed to me, but it was one of mine.

The three of us were sitting in the living room when Liz broke the ice so to speak. “I’m torn between being angry and contemplating what an interesting evening we’ve been through. First of all, I want to thank you, Amy. I think you led the way in making it something positive.”

“And Leon though it wasn’t what you planned; I guess we all got an eye-opening to your other colors. It will be interesting, to say the least, what you thought of the night?”

Amy said, “It looked like we all had some fun. I heard Mom mention you as Lindsay, but it was not as flattering as it was tonight. Daddy, is Kenny correct in calling you a crossdresser or trans? I don’t want to lose you as my dad, but I saw another side of you. I’m sure I saw glimpses of you before.”

Amy took several deep breaths; like she wasn’t done speaking. Liz and I found ourselves both staring at her until she spoke again. “I know, I experienced that there’s more to me than I knew of.”

Liz asked, “How’s that Honey?”

“Mom, there’s more to the birds and the bees than you told me about. You didn’t say, I could be turned on like I was with Layla and Ashley.” There was a young woman named Ashley, but we hadn’t seen Amy with her. We found out that Ashley was someone she encountered when she got a diet Pepsi refill.

The discussion went on until well after midnight and in more directions than one could follow.

Interestingly enough, it didn’t stop after that discussion ended and we all went to our bedrooms. Liz and I being together; started with Liz making sure we both got out of our makeup. I was still in my skirt, as well as my panty and bra. “You know Lindsay of everyone, I’m the one who got the least amount of time with you. I am interested in rectifying that with you now.”

She unhooked and loosened the zipper of my skirt allowing it to fall to the floor. She pushed me back until I fell on the bed, and she straddles me. She had a tube of lipstick that she applied to my lips and then began to get sensuous with me. My manhood arose, but she pushed it up against my belly as she straddled me and moved to her satisfaction. She also directed various responses she wanted from me.

I know that I came no less than twice and she had multiple climaxes, muffling her joyful outbursts into the pillow, our kisses, and biting my shoulder. It was after seven o’clock in the morning that she dragged the two of us into the shower. It took a good time and effort to get ourselves ready for a new day.

“You are Leonard today, and I do not want either of us dragging around ourselves in Amy’s presence.”

It was Sunday evening and Amy was home from friends. She had showered and was relaxing when she matters of factly said, “We’re not going back to as though Friday never happened, are we?”

She asked, “Mom, how long ago was it when you discovered Lindsay again? I thought you said something that you thought he stopped it before you two got married. But I think you also knew he was doing it when I mentioned something when I was nine. Please don’t treat me like that little girl.”

She sat down and we did also. It was I who spoke next, “You’re right, I’ve been in denial about this ever-changing. My excuse has always been; I’d change for the sake of you two, but I haven’t been able to do that. I don’t want to lose either of you.”

Amy looks to her mother, “Are either of you saying I need to choose? I realize you probably need to be out more as, um. I’m not sure how to say it as my dad or as a woman? …I don’t know about you two, but I need more experience with you being a woman in my life and our house… I don’t know how to say things. About the other night, I still loved you as Lindsay, but then you’re gone again and we were not talking. That I don’t find acceptable, I can’t take that.”

Liz says, “We’re sorry. We never should have allowed it to get this far without talking and being open. Are you serious that you’d be open to your Dad dressing and being Lindsay and see how it feels like a family?”

Amy says, “Tina knows. She and I talked a little yesterday and more today. She’d like to know about Dad and see that side of him, so I’m not alone. She even knows I danced with Layla. She thought she and I could even talk to Dr. Ida Hart at the school.”

Liz says, “I don’t know if doing that as school is a good idea yet?”

Amy’s a bit more forceful, “I guess I’m not asking as much as saying Tina and I need to talk with someone. If not at [school, then I want to find someone soon! This is not debatable.”

Her Mom says, “There is an Audra at the Plan Parenthood resource center. She’s supposed to be especially good talking with young women on other topics.”

I tried speaking, “Just a moment Dad, what you have I want to hear, but I hope it will be okay if you and I go shopping for Lindsay with Tina. I think it would be good to get away, maybe up to the Paterson or over to the Sussex area…”

After I agreed, she asked, “So are you still my Daddy as well?”

I said, “Of course, I’ll get this behind me and I’ll always be your father.” I tried to say it convincingly, but neither Amy nor Liz affirmed that with their heads or expressions. I asked, “What do you want me to say then?”

Amy was the first, to say, “Just let me know you love me, and let’s take one day at a time. I love you and I’ll be here for you. I think that’s about the best you can say to me right now.”

I was moved; it was one of those moments a mature child speaks with a wisdom one can only take in and be proud of; my response, for now, was without words. Finally, I respond, “It’s humbling, but I know I’ll need both your assistance.” She thanked me.

Amy asked her mother, “Have you ever helped Dad to get clothes for her?”

With a small smile, “Once, but he was dressed as himself and he didn’t get to try the clothes on when we went shopping. Otherwise, I’m guessing he did some shopping when away on trips; supposedly he was buying clothes for me. I will enjoy doing it with her when we take the opportunity. After our outing Friday night, I’m guessing she’ll be known soon by some close friends.”

I’m sure I nodded my head in agreement. I mentioned, “Your mother and I agreed if you came to know about this or if it became public we wouldn’t compound our problems by lying about it.”

Amy said, “Well, I know at least two students where the mom or dad left because of someone of the same sex. I don’t know if gender issues were any part of that?”

It was later, when we were alone again, that Liz asked, “Do you have any attraction to men other than wondering what it would be like to have a man inside of you?” I didn’t answer but acted as though I chose not to hear or be unresponsive.

She said, “From what I’ve read a good percentage as you wonder and if not do some probing of your own. I’m not saying anything more one way or another. I just want you to know to talk to me if you can.” She pauses until we were ready for bed, “We may want to get a dildo for me to use with you.” I became quiet at that point.

Come morning we woke up early and Liz had her way with me and we enjoyed our time as two women.

It took three months to square away my change with work. It being able quite evident that a formal severing of ways was inevitable. I changed from being an employee to become a contractor for the company that worked for them. They liked my work and valued keeping as a contracted worker.

Once I was able to develop Lindsay’s speaking voice and how I looked; my personal interactions continued with Leon as well as Lindsay.

It was a month after my first outing to the Purpled Goose that Amy, Tina, Liz, and I as Lindsay went shopping at Paterson. Actually being thirty-nine and in good condition and with the help I presented well as a woman shopper. It was a shopping trip for all four of us.