Preparation for Heath/Heather’s Cruise in the Caribbean was now fully underway. A passport for Heather had been expedited; a costly affair, but it arrived in just over a month. It arrived right after July 4th.

Tanning in the backyard was a sensitive venture using two days a week working at home, where Heather could work around the tanning. Doing it during the day limited those neighbors who were working from seeing eyes. Cortney visiting her aunt and uncle became the only unwanted person to see Heather. Cortney’s silence was relatively inexpensive at $20, but Cortney also became an unexpected friend and fan of Heather’s.

Dancing and walking in heels became part of her training regimen.

Darby worked with Heather to hone her packing skills and ironing skills. Roxanne took one day for mapping out every two days on the ship or at ports. There were to be three full days at an all-inclusive resort in St. Lucia. Rosalyn, Darby, and Heather went out three times for dining experiences. Darby found the experiences more fun and less difficult than she expected.

Darby even spent two romantic evenings with Heather. The first was short as it bothered her. She spent the second time instructing Heather on pleasing Darby. On the 20th of July Heather and Rosalyn flew to Florida to begin their cruise the next day. It would take a day and a half at sea to reach their Caribbean destination.

Aubrey and her Fiancée would fly to St. Lucia on the third day. They would be spending a week there. Meeting with her Father and Rosalyn would be decided there at the convenience and interest of all parties. There was a storm possibly coming in on the 20th so they reserved two rooms at the hotel the night before. Darby was with Heather.

There were probably three crossdressers or transgender people on the flights to Florida. One crossdresser befriended Heather as they were waiting for their flight. Marie was going on the dignity cruise. She had been on other trips and was all too happy to share experiences awaiting Heather. Heather said, she did not intend to dance with men, as she was married. Marie tried to convince Heather that she would; then finally said, “We’ll see; it will be your decision?”

There was a table and then a section of tables at the hotel where many were staying. It was for those going on the Dignity Cruise and companions.

Rosalyn had reserved salon appointments for them. Rosalyn and Darby had decided to try and merge Heather into her feminine identity. Rosalyn knew Heather would be uptight and feeling guilty about being away from Darby and worried that Heather’s desires might stop her from being fully herself. While Darby did have some concerns; she knew Heather needed to confront them once and for all. If Heather needed to dance with men or women, or even become affectionate with someone this was the place and time. Darby even told Heather that Darby and Heath’s relationship could survive it.

The salon trip started with a massage, then a manicure and pedicure, and finally her hair and makeover. Knots loosened with the massage, muscles became like butter. The masseuse talked to Heather throughout her massage. The stress showing in her forehead and face smoothed out, soon replaced by a smile and eyes that soon glowed. She undressed and put on a terrycloth robe with only a pair of panties underneath.

The manicurist started with the pedicure and massaging her feet. It was Heather’s second pedicure and this one was like stepping into the clouds of heaven. She developed sensual feelings, but nothing like Heath had ever experienced. By the time Rosa had shaped the nails, used delicate scissors and other implements to clear away unwanted skin tissue. It was like a part of Heath disappeared. The nail polish and seal coat brought forward Heather. A cloth was used to rinse her feet with fragrant rose water and pat dry.

They were done in time to return to the hotel, get changed, and go down to eat with the group going on the cruise. Heather and Rosalyn Had given Heather the twice over to make sure Heather was making a good presentation for herself. There were now over twenty people identifying as the group and there would be another table full before orders were complete.

Their table of eight included Tim as Tammy, Braden as Brandi, Nick as Niki, and Mary introducing her husband Bob as Janet. Brandi and Janet were bigger women, but everyone had a genuine smile on their faces. Once Mary found out that Heather worked as a photographer; Rosalyn made it known the Dignity members had a photographer for the cruise.

Heather said she hadn’t brought her cameras on the cruise as the water, humidity, and sand weren’t good for the equipment. The unmentioned reason was Heather had left Heath and left the needs of others behind.

Voices, mannerisms, and flaws in appearance aside, a sorority of women was forming. Tips, suggestions, and positive feedback were given only if it appeared another was wanting something.

They were to begin boarding around ten and just before noon, they were casting off. It seemed that only a few passengers were surprised and upset to see so many crossdressers and transwomen on the cruise. Men and women were interested to visit and ask questions.

The first evening meal found Brandi, Mary, and Janet, Niki with Doug, Rosalyn, and Heather at the same table. There was a last-minute arrival of Christina at the table. She quickly acknowledged herself to be a conservative Christian and introduced herself to Heather. “I am not here to address everyone, but I’ve kind of been assigned to you, Heather.”

Almost like he had expected her, Heather said, “I’m happy to inform you that I too am a Christian.” Christina looked surprised but recovered and said, “Then you must know what you are doing is a sin and damnable.”

Heather said, “You probably quote Paul saying there is neither Jew nor Gentile, neither slave nor free, neither male nor female in Christ Jesus.”

Christina again was surprised by what Heather said to her, nor was she ready for Heather to casually tap her hand. Heather said, “As far as I know we all come up short, and need the grace Jesus Christ extends to all. You seem to know my shortcoming, would you be willing to acknowledge that you too need his love and grace?”

The food was coming so Heather suggested they eat in peace and visit more later. Christina did seem to be a positive spirit and they ate in peace. Rosalyn identified herself as a friend of both Heather and his wife.

The captain welcomed everyone as they were eating dessert and gave basic information about the cruise and the amenities they offered. A steward had approached Heather and Christina and asked if their eating together was okay or if other arrangements needed to be made.

Heather said, “If it’s not me it will be someone else. We seem to be able together okay, if it’s not we’ll be in touch.” It was Sunday at noon when they were together again Heather said she was going to swim and named which pool and invited Christina to meet her there.

It was two o’clock when Heather arrived at the pool and Christy was soon there. Christina acknowledged that her chaperone was a bit concerned about allowing Christy to meet with Heather alone.

Christy asked numerous questions about Heather and when she thought she was a woman. Heather had mentioned times when he purged herself of her clothing and sought to be straight. It was after a heart episode and meeting with a psychologist that she came to grips with who she was. Heather even mentioned a Psychiatrist who said he could do away with Heath’s desire to be a woman in one visit. It was after the third appointment and a fourth and fifth scheduled that he was through with Dr. Cravats.

Heather was pleased she was visiting with a young woman of some intellect. They agreed to meet now and then but to also give each other some space.

It was on the second full day of the cruise that Heather stopped in her tracks upon seeing a particular person in front of her. It looked like Walter Bush a neighbor from a few blocks of where he lived. Walt said hello, and Heather knew it was him. They agreed to go have a drink and talk. Walt acknowledged he had followed Heather here. “I was glad when you came here going by Heather Anders. It was a companion who first noticed you had panty lines under your slacks at social gatherings. When I hired you for some special photography for our corporation; I began noticing some of the same, my secretary even told me of when you wore no-line panties. Then when word was out you were going on a cruise and I learned through gossip when your ship was leaving out of Ft. Lauderdale things added up.”

Walt said, “This is a long way to come for a dance, but it would have been very costly if I were wrong.”

Heather said, “I guess it’s expected that I will dance with a man or two on my vacation, but I assure you It won’t be going further than dancing.”

Walter said, “I’m comfortable starting with that. I won’t lie, I’m hoping for more of the kiss, a little foreplay, wherever it goes.”

Walt complimented Heather that she looked as good as he had hoped. It was that night many stayed around after dinner and danced. Walter had come over to Heather’s table and asked Rosalyn if it was okay to take Heather for a dance.”

“That’s one of the things she came on the cruise for. Doesn’t she look good?”

Walter spoke to Heather, “My Dear you are the prettiest woman I see here.” He offered his hand and helped her to stand. She was wearing two-and-a-half inch heels, a half in higher than recommended. There would be more than one person who’d sprain their ankles wearing higher shoes. Heather had them but was saving them for St. Lucia.

Heather was more nervous than others knew. The first dance was a little fast and they were a part. It was the second and third dances being slow and close together that made Heather nervous. She could tell that Walter was becoming aroused during the second dance. Walt had mentioned Marie Dubois and asked about the rumor that she had hired him to do some landscaping as well as photography.

Heather said, “Yes, it was an interesting request, to say the least. My interest was in saving the great tree in the back, and the legend of it not being a successful hanging tree. The old Barkly place where the first old man Barkley came out with a shotgun and shot down the hanging rope before the victim could be hung.”

Walt acknowledged he knew there was a legend, but not what it was about. “You take interest in those things like you’re one of the women in the historical society. That’s one of the things I’ve come to like about you.”

They sat and talked some more. Brandi finally came and encouraged Heather and her friend to dance again. “After this, we’re going to the Night Sky Lounge around 10:00.”

Walt stood up with Heather, “I have a better idea, why don’t you relax a little and change into a little black dress and I’ll meet you up at the Night Sky Lounge.” Walt hugged her and stole a kiss. Heather knew she closed her eyes and savored the kiss a little.

“Could you walk me to my cabin, that way if you’re serious about going up there I won’t be going alone.” Once back in her room, she was surprised that Rosalyn was not back yet.

‘What am I doing,’ thought Heather herself as she dropped back on her bed. Heath was happy he came on the cruise. He’d never been around other crossdressers or transwomen except when he went away to a conference and explored some off-beat night spots. And never to visit others like himself as friends.

He had never expected to see someone he knew or liked that they kissed him.

He was in the act of sitting up when the key latch was triggered and Rosalyn was opening the door. Rosalyn was talking from the start. “You’d never believe how much fun a regular woman could have here.” She said, “Most thought I was your wife or companion like we’re an item… Several women asked if we had kinky sex. Others wanted to know why I let you loose among all the others; weren’t I afraid of losing you?”

She went on, “I danced with Tammy; she was fun to dance with. It reminded me of dances where women danced with other women until the guys finally loosened up.”

Finally, she asked, “So how did you like dancing with that guy; I hope you didn’t mind I pushed you to dance with him?”

I was standing by the time she asked me about dancing with Walter, though she didn’t know it.

“I don’t know what you’ll think of me if I said I liked it or not?” I watched her eyes, for a clue to what she thought.

“Well did you or didn’t you,” she asked. “We expected that deep down you needed the experience.”

“Yes, I liked it, especially when the music slowed down. I didn’t expect to like it, but you had gotten me to experience the day as Heather. And it was nice to be away from Christina.”

Rosalyn interrupted, “You should have seen Christina’s face when you were walking away to dance with him. She soon left herself. Did you know she’s finished her first year in college and she says you’re an interesting person? She asked me if you indeed thought you were a Christian.”

I soon broke off our conversation, saying, “I’m going to the Night Sky Longue, and I only have enough time to change and clean up.”

She reminded me, “You know you only have one visit up there as we travel to the islands?”

“Yes, I know. I was wondering if you could help me with evening makeup?”

Rosalyn said, “Can I put out something for you, for dancing?”

“If you’ll help me with makeup and my hair?” She pushed me to take a quick shower, reminding me not to get my hair wet.

Once I was out of the shower and dried off, I saw that she had a glittering red and silver dress lying there for me. I said, “I didn’t remember getting that.”

“But you tried it on and liked it; Aubrey thought it would be a surprise, hoping you’d relax and have some fun.”

Rosalyn said she needed to use the washroom and suggested I get changed into the dress while she was in there. I put on fresh panties and a lace bra and then squeezed into the dress and moved it until it lay properly. I was happy about how it looked on me.

I brushed out my hair to how I liked it. I was in front of the mirror, going as light as possible on the foundation makeup. I shaved the little facial hair I had while in the shower. My complexion had color from being in the sun and just needed some help to set my eyes and lips off.

I thought I was done until I thought about shoes and realized I didn’t have stockings on either. Rosalyn pointed to a small package of stockings that had been under the dress. They were a pair of shimmering white silverfish stockings. There was a knock on the door, and I eked out, “Wait, I need to get on my stockings and shoes.”

Rosalyn turned away laughing, while I shimmied up the skirt of my dress, rolled up the stockings, and one by one brought them up my legs. I stepped into my shoes, grabbed my purse, and was out the door saying “Goodbye” to Rosalyn.

The hug that greeted me on the other side of the door, was both a surprise and felt good.

Walt is five inches taller and I felt comfortable in his presence. His hand was warm, and I was anxious. I mumbled to myself, “I shouldn’t be here, but I like him.”

Walt said, “I’m glad that you’re here, and I’m glad you like me?”

I stuttered, “I didn’t mean to say that.” He had pushed the elevator button to take us to the upper deck. Walt said, “You make a better-looking woman than I had hoped.” He leaned toward me and sniffed, “That is a nice fragrance on you.” The doors opened and we were joined by another couple. Niceties were exchanged; Rodney introduced Rachel and Walter introduced me. Walter was looking for someone as we got off of the elevator, and a couple was waving to him. Robert something introduced Nicki to us and soon realized that Nicki and I already knew each other. Nicki and I both ordered regular-size Margaritas. I was sitting on a barstool facing Walter and he was standing close to me, with one of his legs between mine. My eyes caught on his lips as he slowly and gently moved to kiss me. “I shouldn’t…” he kissed me and quickly asked me to dance.

“I said, “Walter, we shouldn’t be kissing.”

He asked, “Why did you come on the cruise? I thought it would be for experiences like we’re having.”

“Kind of, but it’s happening too fast and so soon already.”

“You mean you didn’t expect an admirer?”

I asked, “Why did you follow me here; Do you like girly…” I didn’t exactly know what I wanted to say. But he said it, “Because it is something I thought of a long time, and when I thought it could be you I knew I had to try.”

We were dancing and I liked being in his arms and the way he was looking at me. But I kept telling myself it wasn’t right.

He pressed against me; he was aroused and I didn’t push him away. We kissed again, and I became lost in my feelings.”

It was after 1:00 and we found ourselves in his room. I looked for my phone in my purse but found condoms. Rosalyn had to have put them in there. I lifted them and whispered, “I didn’t plan on this?”

Walter saw and took them, “It looks like Darby gave you permission.”

Heather thought, ‘Could that be true? Would Rosalyn do it on her own….

To be continued…