It was Sunday evening of Mother’s Day and my wife asked me what I wanted for Father’s Day; not taking her seriously I said a nice dress or skirt outfit. She asked, “Would you mind if I choose the dress and surprised you?”
My response was, “Have at it, you might as well go the whole nine yards!”
Come Memorial Day, Darby told me she could wait no longer for Father’s Day. She called our friend Rosalyn over and had me sit down and she would bring my gifts. I hadn’t a clue as to what she was about to do. I had forgotten about Mother’s Day and remembered nothing of our conversation that evening.
While she was gone, Rosalyn asked, “Are you going to mind that I help you to have the best time possible?”
I responded, “You are our best friend; if that is what it will take I’ll be glad to receive your help.”
I heard my Darby coming from our bedroom and turned my attention to her. She was carrying a long gown bag in one hand and carrying a gift in the other. Our daughter Aubrey was with her which was a big surprise in itself. Aubrey lives twenty miles away from us, and I never heard her come into the house.
Aubrey has a couple of gifts that she places on the table in front of me and then hugs me. “I’m here for moral support. Please know that you have my full devotion. I’m eternally thankful for all you did for Momma.”
I’m asked to sit back down. First, there is a video hook-up with our son Kent and his wife Anna. Anna is a therapist and she greets me warmly. “I think you have an amazing wife and we’re proud of both of you as well as Rosalyn going with you. Kent and I are gifting you a cruise for two. Giving you the freedom to express your second self.”
Mom, my wife said, “Since this is what you asked for on Mother’s Day and I want you to know you have my support; please open this gown bag first, it’s for you.”
I unzip the bag and there’s a violet, pink, and silver gown inside. She said, “This is for a special night on your cruise in the Caribbean. Theirs often a time when a group is invited to dine with the Captain, or a ball for everyone to dress up and celebrate. It will allow you to dress up, go to the ship salon, and have a fantastic time.”
I was flabbergasted and leaned back in the chair; I was waiting for someone to tell me the real surprise. A Caribbean Cruise with Darby would be great, and Rosalyn along would help to make it a good time for both of us. Finally, I asked, “Who’s all going and when?”
Darby unloaded the surprise, “You don’t remember, do you? I asked at the end of Mother’s Day what you’d like for Father’s Day. And you said a dress or nice skirt outfit. Well, I have changed my mind; I don’t want to go out with you dressed as your female self. This is your gown for your cruise in the Caribbean: St. Lucia, Barbados, and Martinique. With air and cruise, it will be a ten-day trip. Rosalyn will go with you to help you along the way.”
Darby had gone through a lot over the past several years and I of course had been there with her every step of the way. She had said numerous times, “You’ve cared for me better than my Mom would have if she was able.” Today she said, “I don’t understand this side of your life, and I never want to let go of you. This is the closest I can come to embracing and celebrating this part of you!”
Darby got up, came to me, and as she was giving me a hug and kiss. “I will even take you to bed once after the cruise if you still want.”
Aubrey came over and handed me a card and her two gifts. “This time I suggest you open the gifts first.” The shape of the wrapped gift suggested what one would be. It was brightly wrapped and looked as though they were shoes.
I slid my fingers under the edge of the wrapping lifting the taped areas without tearing the wrapping paper. It was a three-inch heel with an ankle strap and open toes. Aubrey spoke up, there’s a gift receipt. I’ll tell you more if you need to exchange them.” I looked in the box and there was a pair of stockings. They were silk though I hadn’t looked that closely now. The other gift was small and I was surprised as I unwrapped it to discover a long jewelry box, and when I lifted it there was a beautiful silver necklace. I was surprised that it was long enough to fit around my neck easily.
Though I have a slim neck for most men, necklaces I’ve tried have always been tight. Aubrey had taken it out of the box and had asked me to turn around and lift my hair out of the way. It lay beautifully around my neck, everyone complimented me on how it looked.
I was near tears, but wouldn’t cry. It was now time to open the card. I took a breath and opened it. I could hear Aubrey’s voice as I read it. She and Mom would take me shopping for a nice wardrobe. She agreed to pay for half of it. I was surprised about the amount she expected it to cost. Darby said, “I’ll be there at least for part of the time shopping. You and I will pay for more than half if that is what it takes to get you a wardrobe you and be proud of.”
Rosalyn broke in, “I’ll take you to a salon here for a manicure and pedicure, as well as help you shop for makeup.”
We have two sons, but Kent is the only one partially accepting of this part of me. Anna spoke, “Daddy, I know this has to be surprising and difficult as well as exciting right now. We’ve scheduled your trip to start on July 14; that should give you time to start pampering yourself and getting your hair and complexion into shape. I can’t be counseling but I’ll give you a listening ear.”
Kent said, “Dad, Anna, and others have brought me a good way. I’ve usually been proud of your sensitivity. You’ve helped me to grow as a caring man. I know Grandma said this part of you has always been there. I just see it as part of your male nature. I will however celebrate for you. You have my best.”
He added, “You know Calvin loves you.”
Darby got everyone’s attention, “We will have a traditional Father’s Day on its regular day. Calvin will be here then.”
The night of Memorial Day, Heath wanted to romance his wife but as usual, even the talk of Heather; Darby was not in the mood for romance with Heath. It had been that way since the year before Aubrey was born and Heath made known to Darby about his cross-dressing.
It was two days later when Aubrey called, “Daddy, I would like to meet you for lunch on Friday. We need to go shopping and Mom has agreed to be gone Saturday morning.”
She said, “I’m wanting to pick up Heather at the side of the house. It will be discrete that way. We’ll go all the way to Flemington, I know some nice shopping areas there.”
I agree to lunch and give a reserved yes to Saturday. It was too soon to lose all traces of Heath as I dressed on Saturday.
Come Friday and our noon luncheon, Aubrey was bubbly as she usually gets when she meets her Daddy. It’s been six months since she’s become an RN. She’s been very accepting of his female identity. She thinks it is more than cross-dressing, and enjoys being there for him.
Aubrey was thirteen when her mother first became seriously ill; she was sixteen when her mother’s car accident complicated her health issues. With Darby’s mother a thousand miles away in Iowa; it fell upon Heath and Aubrey to take care of Darby.
It was an extended time of being bedridden that Darby’s pride gave way to the personal care Heath was giving her. Bathing, dressing, even using the toilet, and needed personal hygiene.
Once during a stressful time in her illness that Aubrey heard her mother belittling Heath about Heather. Aubrey had since taken to giving her father manicures using a clear polish on his fingernails, sometimes with a pink tint. By far that was an exception that he would allow.
=^_^=
Friday’s luncheon went well, though he appears as his male self, Heather was very present; from ordering tea, a salad, and a quiche to the air kiss on his daughter’s cheek. They both talked about the shops at Flemington and what they’d be shopping for. Aubrey had given over her tablet for her father to see clothing ideas.
Aubrey agreed to stop early Saturday to put the finishing touches on Heather’s makeup. Heath acknowledge he’d be both anxious and excited to be with her the next day.
Come Saturday, my wife knew Aubrey and I were to go shopping. She was gone to meet up with Rosalyn shortly after 9:00.
I had a simple outfit laid out in the guest room. I had already showered, shampooed, and conditioned my hair and was drying it out when Darby left. With Darby’s informal consent, I was just a little more relaxed in moving around the house than Heather. It was the second time I shaved my legs and underarms; my pantyhose and blouse both rejoiced over the smooth silky difference that I felt. I had chosen a different necklace to wear from the fancier one that Aubrey had given me.
Aubrey and I went to her place for tea and to talk. “Daddy, there’s something very sensitive I need to talk to you about. Do you have breast forms, if not I’ll be buying you a pair?” Daddy blushed red, “Daddy, you might as well get used to that this is personal but no longer being hushed.”
I said, “I’ve gotten along this long without them…”
Aubrey hushed me up, “This isn’t about your private world. You are soon going on a cruise and will be out in public. You will want your girls to move like regular women. You also need to get used to having them; they will change things for you.”
We stopped at Stacy’s Bra and Lingerie store, Margaret was heading up the store this morning and she assured me that they fitted and sold breast form for many reasons. She had me look at a variety that I might like. I hadn’t realized one could get them with or without nipples. With Aubrey’s input, I selected three and after trying them I selected the Soft Touch and the Swimmer form. Aubrey was ecstatic that she talked me into both. The nipples were two inches wide and would be part of the breast forms and not glued on. Aubrey bought a generic pair that would help try on clothes today.
After we were at our second clothing store and I had tried on five different dresses or outfits, I was relaxing. My daughter had me try on a pair of stretch designer jeans and a pink sweater top and I bought them, another break in the ice. My final selection for the day was a dark satin skirt and a shiny black top.
I agreed to buy the outfit, and Aubrey said I was to wear it home. When we left the store and were heading home, Aubrey turned into Michael’s which featured steak, Italian, and seafood. I tried to argue, but she said we were already late and Darby and Rosalyn were waiting for us.
I was reminded that Darby said she wanted to see me as Heather and I had agreed. A picture of me in my present outfit had already been sent to them. My phone rang and it was Darby telling me to relax. “Heather, you are beautiful and this is a nice way to come together.”
Darby always orders fish when she can, and I ordered sirloin tips on a bed of wild rice, peppers, and onions. Rosalyn and Aubrey became like supporting cast as we ate. I had two wine glasses and quite enjoyed myself. My personality as I had dreamt of it fit well into our gathering. I rode home with Darby, and Rosalyn and Aubrey followed us, bringing the beginning of my new wardrobe home.
I was to model my new clothes, but that ended with the third item a printed cotton dress. My vanity had gotten the best of me, and I had to change my makeup with each dress or outfit. It took too much time. My wife true to her nature, asked me to sleep in the extra room since I had spent the day as Heather. But it was after midnight that Darby snuck into bed with me. She gave me a passionate kiss. I wasn’t wearing anything fancy, but it was feminine. Darby whispered and touched me. She would not let me enter her, as she seemingly was relating to me as Heather, not Heath.
=^_^=
We went to worship, but it was not at our church, but one more open to receiving a diverse group of people. I was presenting as Heath, but a few noticed my manicured fingers and the hint of my hair being swept over from a more feminine style.
Adrian and Paula invited us to lunch and we went with them. My wife was open in telling them she had not been very accepting of me. Adrian complimented her, “But I suspect it was you who chose to come here today. I am impressed; I wish my parents had progressed like you.”
When they heard I was going on a cruise as Heather, Paula passed a note to my wife, one she smiled and said yes to, but would not share with me, then or later. Paula asked if I had practice dancing as I might on the cruise. She offered herself and Adrian to teach me as Heather to dance. This was all sending my spirit into joyful dreams. Darby even asked for a day and time to be set before I back away from it. Thursday at 7:30, they would pick me up at our house and I was to be dressed as Heather.
Monday, I had an appointment in the evening to meet with a couple about photographing their upcoming wedding. It was for late in the spring of the following year. But Samantha and Shelley wanted to be sure that I would be willing and interested in doing their wedding. There would be two brides and bridal parties, and only one bridesmaid was to be a best friend Jonathan dressing as Joni.
While the couple was popularly known in many circles and the guest list quite open; they wanted my vision of such a wedding. Sam invited us to meet around a table and once we were seated; she asked, “Would you be comfortable if I painted your nails?”
“This is highly unusual, but seemingly you are seeking to know if there’s a feminine side to me. There is, but I am just now beginning to become more public about it. I hope it need not be part of my photographing your wedding.”
Paula said, “No, it would not, but I am asking if you’d be comfortable with my painting your nails as we talk?”
She chose a dark red color venturing into purple. She shaped my nails a little more feminine look and put on a base coat, two coats of paint, and a top coat. I had not expected it to be so elaborate or lasting, but I had not stopped her along the way.
When we were finished meeting she gave me a bottle of polish and a lip gloss of the same color. We had agreed to a contract frozen at this year’s price with an early signing discount of 15%.
There was no attempt to sneak into the house to hide my nails. It was always better to be upfront with Darby; especially now that she was being more accepting. Darby was surprised and asked forthrightly if this was to be a new practice. I said it was serendipity as it transpired at Adrian’s request.
Come Thursday, I wore the knit dress that Darby had placed out for me. I purchased it when I shopped with Aubrey. I didn’t notice how I looked in it with my new breast forms. Adrian commented, “It’s a wise choice as it’s good for the variety of dances we’re going to teach you.” First, we went to their home and they quickly taught me the dances. Despite my protest, we went to a wine cellar to eat and relax. When we went upstairs at 8:30 they were having a dance where I was to continue learning the dances. It was an LGBT-owned establishment. And it was there I had my first experience of dancing with a man. Byron was a good dancer and he quickened my pace in learning two dances; before the third song slowed things down.
He hadn’t shaved since the morning, and I got to feel how it felt. I was staring at him in disbelief as the third dance ended. He mistook my pause as waiting for him to kiss me which he did. The first quick kiss was followed by a longer and more passionate kiss. I quickly pushed away as I knew I was slightly aroused.
Once, I was back at our table, Paula took to talking to me. “You just reminded me of when I first went out with Adrian. Adrian was the shier one like you, and I was anxious like Byron was.”
“I don’t know Byron well, but most of us here know him. Something caused you to pause; while Byron was concerned that you paused and he wondered if he didn’t please you. I did that with Adrian and I filled the void with a kiss.”
Heather spoke, “I was taken back by the coarse stubble on his face. It wasn’t terrible, it just surprised me. What was more disturbing was how his kiss felt and that I responded to the second kiss?”
“Don’t get upset, I suspect you dreamt about an unknown man kissing you Heather?”
“But what am I to say to Darby?
“If you’re not planning on going out with him, I’d suggest nothing,” said Adrian. “My understanding is that you’re going on a Caribbean cruise with other crossdressers and trans people. You’ll receive a lot of attention and compliments; there will be hugs and kisses, mostly air kisses. Things like that will happen, don’t get overly concerned.”
I learned a good number of dances and Darby was excited to see me show them. Either Paula or Adrian had sent her two pictures from the evening. Darby said, “Paula told me what you’d do. I expect you were surprised to be dancing in public and twice with men. Were you surprised as I thought you’d be?”
=^-^=
Saturday, Darby had me work around the house and yard with her, which wasn’t a surprise. But after cutting the lawn she had me change into my designer jeans and help inside. Only how I was dressed was different.
During lunch, Darby said, “Usually on Friday nights you’re downstairs doing whatever you do in your cubbyhole. Last night you were up here watching a movie with me. What give?”
I wanted to read some stories on Big Closet, but I thought I had spent enough time on Heather. “I decided the focus wouldn’t be on me but about us.”
Darby leaned close and we shared a kiss. “Thanks, I know that’s usually your time to unwind. I was pleased that you shared it with me.”
“I’m even more thankful, that you’ve been stepping into my world and considering my other side.”
Darby had us go sit in the living room, where we would speak more. She said, “I see the reality of who you are isn’t so scary. I can’t say I quite buy into it, but the reality is better than I imagined. I went back and read the letter about yourself that Paula Rudd had suggested long ago.” I had forgotten about the letter, though I still had a copy of it on my computer…
To be continued…
