It was shortly after our first child was born that Elaine caught me crossdressing. Her being a mother set off my feminine feelings to become stronger. While she wasn’t exactly happy about my dressing as a woman, we were still very much in love. I had to promise several things: I wasn’t to use her clothes that I would misshapen; I wasn’t to wear her underclothes; and if I couldn’t quit there was a day she would enjoy feminizing me. She did add one more stipulation when Aubrey became one. That the children were not to see me dressed as a woman. Elaine had just found out that she was pregnant again. Darby was born a year and a half later than her sister to the day.

Aubrey was four years old when she heard me singing a popular song in the shower and she called to her mommy, “Mommy daddy’s singing in the shower and he sounds like a girl.”

Elaina didn’t miss a beat, “Your father likes to sing and can sound very pretty when he tries hard… I think it is nice that Daddy can sing beautifully, don’t you?”

I didn’t know it, but Aubrey and Darby saw my reflection in a mirror with me dressed as a woman. Aubrey was seven and had decided it might have been me she saw, and she went looking for clothes to prove it.

When I heard her outside my room, I quickly undressed and threw the clothes into the back of my closet. I went into the master bathroom and locked it figuring I was safe. I had showered; making sure I lost all traces of what I had done.

When I came out of the bathroom with a towel around my waist Elaine said, “Here are the clothes you are to wear when we go out to dinner.”

My response was, “I can’t do that everyone will see me.”

She said, “Adam, you’re not the first man to dress like a woman; plus, it is what we agreed to if the girls said they had seen you again. We will be going to the Underground Vine for dinner. I’m going to tell the girls we’re going out to dinner and they’ll be seeing Adriana.”

She kept the door open a crack so I could hear her talking to our children.

Adam asked, “Where in the world is the Underground Vine?”

Elaina said, “It’s at New Hope and it stays child-friendly until 9:00 tonight. I told you when your sister heard Adriana singing this would happen and you agreed. Daddy, you had sworn it wouldn’t happen ever again." "We knew that that was a promise you couldn’t keep. But you agreed about this and I’m holding you to it.”

I looked at Elaina and then at the clothes she had laid out on the bed. I heard her, “You know you can pass for a woman, now get to it.”

Elie left the room and I could hear her talking to the children as they went to get ready to go out.

“Aubrey and Darby come here and listen to Mommy?… We’re going to dress up and go out to dinner.”

Aubrey spoke, “But Mommy, Daddy was dressed like a woman? Is he going to come with us?”

Mom said, “Aubrey, you and Darby can call him Adriana tonight. And yes, she’ll be going with us... If she looks pretty, I hope you will tell her that.”

“But what if she doesn’t Mommy,” Aubrey asked.

“Then we’d have to help her look better before we go out,” her mom told Aubrey. Audrey smiled and went with her mother and Darby to get them dressed and ready to go out. Aubrey and Darby enjoyed going out to eat if they were able to dress up. Tonight would be one of those times.

Having gotten the girls ready, she went to their master bedroom and saw that Adam was in the dark blue A-line dress and was already in a bra with padding and a camisole. Adam said, “I’m having trouble getting my hair properly done. Elaine, I know this is my fault but I don’t want to do this.”

Elaine said, “One, get your voice for Adriana; I don’t want to hear Adam’s voice again. Two, you work on your makeup; I know you’ve practiced. Do what you can and I’ll help you finish up.”

Adam focuses and begins to talk to himself as Adriana, ‘Light on the concealer and foundation.’ He has a blemish on the left side near the jawbone. It is gone with the concealer and foundation. He hears Elaine talking, complimenting the uniformity and smoothness of Adriana’s complexion. He knew he needed an eyeliner, but that was hard for him to apply properly. He could give it over to Elaine, but he knew that she’d want him to try first. Adriana was proud when she got her left eye done. But she had tired and the steadiness of her hands didn't allow her to get the other eye done and Elaina took over for him. “Learn to do this properly it will help change your image from being a man to Adriana. You can be thankful you’ve taken good care of your hair.”

Elaine had put something on our bed and then walked out of the room saying she was checking on the girls. “I suggest you put your panties on over this.” It wasn’t mine, but I knew it wasn’t for Elaine. It was shapewear with a little padding to the hips and buns. It would go up to just under my bra. Besides adding to my bottom it took in my waist and made everything look smooth.

That changed my mind about what I was wearing. I had a skirt, that was very pretty but hard to hook and zip properly. I had a pretty pink sweater-like blouse to go with it. After I put on the shapewear, the skirt fitted as I hoped. The pink blouse snuggled my waist and the little extra it gave in my bra gave me a nice feminine shape. The hem of my skirt was just above the knee but would slip higher when I sat but then my legs would be under a table.

Elaine came in and seemed delighted, “I am nicely surprised and I am sure our daughters will be as well.” She called to Aubrey and Darby and as they entered the room Aubrey said, “We were told we should tell you if you look nice as a mommy, but we’re to call you Aunt Adriana. We never saw you this pretty before.”

They sat on our bed as Elaine finished getting dressed. She had put back the skirt outfit she had out and chose a prettier evening dress that she wore on special occasions.

Elaine put on some music as she told me she wanted me to practice singing with my countertenor voice, both were old Carol King songs. I knew them Tapestry and Natural Woman, and they had sounded good in the shower whenever I was alone.

Upon finishing the second song, Elaine said, “Now and until this evening is over I would suggest you speak with that voice.” My speaking voice at first wasn’t as smooth as singing a song; I knew and had practiced. But Elaine kept me talking with her or our children as we traveled and arrived at the Underground Vine.

Constance the proprietor greeted us and said our table was awaiting us. Elaine introduced us and Constance thanked us for trusting them as a family place. My dinner consisted of the thin slices of filet minion, roasted cauliflower that I thought was a potato and asparagus. The red wine they served with it was from one of three local wineries that they used. The girls were thrilled with their roasted chicken pieces and finely chopped asparagus. Elaine enjoyed her channel Catfish.

Come eight o’clock the pianist was playing and Elaine and I began dancing as there was another female couple. When Elaine was open to the third glass of wine she asked, “Constance where would you recommend a lodge for us to stay overnight?”

Connie smiled, “All the places are friendly to our customers. The named hotel chains are probably better prepared to serve you and your children. I will be thankful and discount your bill if you assure me you will stay in the area tonight.”

Elaine responded, “You have already done a great service in giving us an enjoyable night out. No discount is desired.”

I started to say, “But…” and was stopped.

Elaine said, “I planned for this possibility.”

I differed, “I am not ready to be out in public.”

Elaine turned to Connie and myself, and said, “You already are.” She asked, “Connie, doesn’t she make a good-looking woman?”

“She does, but whether she does or not is immaterial, this is who you are, become comfortable with yourself.” Her seventeen-year-old daughter, Madi, soon appeared and Connie introduced her. “Madi, if they would be open to staying another hour and a half would you be open to watching Aubrey and Darby?”

It was now 9:15 and a good variety of night customers were there and we enjoyed ourselves. During the slow dances, we would change who was leading. Twice another couple of women cut in and danced with each of us. It was ten-forty when Madi drove us to a hotel and helped take our children inside. I paid for her Uber ride back with a tip as well as paying her for watching our children. She said, “This was on the house, my mother was pleased to help you, just please come back sometime.”

Madi hugged me and whispered, “We are very happy for both of you. It looked like you had a wonderful evening…”