Daydreaming on Deck (Part 1)
By Sabrina G. Langton

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Author's note... Here is a story about a quiet, married, older, new transgender woman, a listener, but she never tells anyone about all the conversations she has inside her head... I hope YOU like it...

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"Hey!"

"Oh, hello."

"Beautiful out today."

"It is."

It was starting to get dark. He was out with his dog, a big black lab mix, I loved when he stopped to talk to me. He always had a smile on his face, he always licked me. The dog that is. "You look so nice, are you going somewhere?"

I smiled, I loved a compliment, "I so wish I was."

I was wearing a long-sleeved black dress with gold polka dots. It had a thin belt emphasizing my thinner waist. I had on nude thigh-highs and four-inch black high-heeled booties, just up to my ankles. I was showing off my knees leaning on the railing in the back of my house, I felt my breasts shift slightly as I moved. We had a huge deck, I felt tiny on it. I could smell the flowers and spices growing in the garden. I had on a long blonde wig, darker streaks, darker roots. I just put it on, it was hiding my longer hair underneath, I wanted to try on something different, a new look. I had on just a touch of makeup, long lashes, and a little bit of mascara. My lips were red, I am sure he could see my smile from his house an acre away. I turned around.

"Oh, hi, I thought I heard talking." My wife, Linda, was coming outside with drinks, she had just gotten home from the club, she smiled when she saw me talking to a man, a man she knew. "Ahh, Logan, I see you finally met Sabrina."

"I did, I followed the scent of her wonderful perfume."

"Stay for a while," She handed us a drink as I got water for the dog, She went in to get herself one. It would be nice playing with my hair and showing off my long nails for a man. Crossing my legs and practicing my voice.

Linda didn't know that he had met Sabrina before.

***

Last summer both my wife and I turned forty-five, the two kids, a boy, and a girl moved out of state, and we decided to each get involved in something different. Something we were passionate about. Linda took up golf. She started to play when she was a teenager with her father but then stopped when we got married and started working full-time. Now she has been taking lessons and practicing for almost a year, she even joined a Club. She is out of the house with her equipment sometimes three to four times a week, I love that she found something she was passionate about. I let her tell me everything about it, about all her opponents, golf cart mishaps, and missed swings. I was enjoying it too.

Me? I went a slightly different route. I did something I have wanted to do for years but I just couldn't make it work. It was way too hard for me. Once I slowed down at work, took some money from our investments, started to relax, enjoy life, I knew I was completely ready.

I lost weight.

Between exercise and diet, my body completely changed for the better. I was 5'8". I was now 145 pounds. I was perfect. Linda was amazed at how great I looked and I was amazed at how great I felt. I was ready to move into a different phase of something that I had done forever, crossdressing.

I got rid of everything that used to be in my boxes, hidden in my closet. All the dresses were three sizes too large, all the ripped lingerie didn't fit anymore, all the makeup was dried up and old. I only kept my heels... and one simple white dress. Now I wore the most exciting outfits, outside in the back of my small world. I started crossdressing more seriously now, like when I was younger, before and after college. And later on when I started to realize I had a touch of gender dysphoria. I wore panties and pantyhose sometimes under my male clothes. I had been dressing up when Linda wasn't home for years. Nothing ever fit right, I didn't have the right type of makeup, or foundation color. I was too nervous and paranoid, it wasn't working but I needed it to. Now... everything was. I had my own room, full of my own female clothes and accessories, shoes lined up on shelves, a vanity full of makeup and nail polish, I was ready to do this right, the correct way. I was ready to introduce my perfect thighs and the genuine me to someone, to anyone.

A year ago, Linda was looking at me in my short orange summer dress. "What are you going to tell people when they notice your perfectly smooth legs?"

"I was thinking, I was just going to tell them I'm a crossdresser."

"Mmm, really?" She squished her face watching me brush my hair in the hall mirror. My hair was quite long, I have been growing it for years, it came down just to my boobs, which were breast forms size D. I was able to get my hair to look pretty nice, I had a bunch of different styles I was trying out, and my natural color was perfect. Strawberry blonde. I was surprised that Linda assumed, more people would be looking at my legs.

"You don't think I should?" I looked at her, she was quite cool about me dressing up now, quite interested in my style and mannerisms. As long as not too many people saw me, then started asking her questions. I had told her all of my dressing-up stories, even when I was young, I always told her mostly the truth, and she seemed okay with every new revelation.

"Well if people ask, let's tell them you are transgender or just trans. Crossdressing sounds like a hobby and trans sounds more like a disease." She laughed as she got her new golf clubs and gloves together. "What are you going to tell the kids, well, if they find out?"

"Telling Jenny should be easy, Mark might need a little more explanation. I'm not dressed all the time, it's not like I am becoming a woman."

She was studying me, shaking her head, she looked a little undecided. "Okay." But soon her mind was off of me, it was too late, she was ready to go, she was going to leave me for the entire afternoon. I would be dressing in at least four different outfits today, taking pictures and videos. I might even go into the city and drive around. I was thankful that Linda never said to me that wearing dresses was a waste of time, or silly, or even harmful to our marriage. I was very lucky. I now did everything she asked of me and more. I was the perfect partner. I was quiet and patient and stayed in the background where she could barely see me. I knew she liked to talk, and me? I just listened.

She kissed my cheek. "Bye, bye girlfriend have fun, be careful on those heels." She was out the door, forgetting about her trans husband and thinking about the eighteenth hole. I didn't want her to worry about me, I wanted her to have fun with her friends. She had three times as many as last year. I wanted her to tell all her friends about her hot trans husband, with the perfect smooth legs.

***

"So Logan, how is the work going on the house? Did you get the permit for the porch?" Linda knew the right questions to ask a man, she was always interested. She worked in medical insurance, and not surprisingly she could converse with anyone. She was into home improvement, DIY, shopping for the best contractors or gardeners, arguing with jerks, she knew almost everything.

Me? She called me a dumb blonde. I usually just smiled and played with my hair, or wine glass or fork when we went out. In either gender I was quiet, I was usually happy to be anywhere. I was happy people were letting me hang out with them and immerse myself in their personalities and voices. Every one of our friends, either husbands or wives were ultra-handy, able to fix a sink, a door, an air conditioner cooling system. Everyone was working on their cars, working in their garage, working on their portfolio. In my head I was working on my look, working on my mannerisms, always daydreaming. I was always distracted, I was an artist, a dreamer. Absolutely none of our friends were like me, they were more conventional, realistic. They were all just like Linda.

I was petting Merch, the lab. He was sniffing my ankles, I had a tiny bit of Chanel perfume there. Merch was more my speed. He needed nothing more than my long nails scratching his head and the scent of my expensive perfume.

I looked up, Logan was watching me. "So Sabrina, have you tried any new restaurants lately?"

I smiled. "I did." This was the type of conversation I liked. I wanted to talk about how things tasted, felt, sounded, looked. I wanted to talk about movies, books, music, and restaurants. "We went to the new Italian place on Third Avenue. I had the best cheese plate ever."

Linda laughed, she always thought what I loved was slightly underdeveloped, like I wasn't paying enough attention, but I was. Along with the cheese they gave us a honeycomb, fresh jalapenos, pine nuts, ginger jelly, and more, it was quite wonderful, and the staff was so nice. I wouldn't get a chance to tell Logan about it though.

She sniffed, "Cheese? That's what you liked best out of all the things we tried?"

I made a sad smile. "It was." I felt I should have said sorry so I went back to petting the dog, he didn't care if the things I loved were frivolous. I would tell him later about the six kinds of cheese we had, he would lick his chops, I would give him a piece of jerky, and thank him for letting me scratch him.

Logan touched my hand, it was on the dog's back. "The builders will be off tomorrow. Why don't we all go to the Italian place and try it? I love a good cheese plate." He smiled, he was being nice to me, he was getting me involved.

"No good, every other Sunday I have brunch at Gold's golf club, just the golfers. We talk about our handicaps, heh."

"Well, Sabrina how about you and me?"

I was surprised. "Me?"

The girl me? The one in the expensive stockings? The one in the Maidenform bra? I looked at Linda, she knew I would be dressed as a woman the entire weekend, especially if she wasn't taking me to brunch with her. She didn't like that I saw people dressed as a woman, I was surprised she was okay with me talking to Logan.

Linda gave me a little conspiratorial smile, "Sure," She touched my other hand, "Go, you two have fun."

***

"Are you going dressed as a girl tomorrow with Logan?" She asked and I nodded. She didn't seem too excited about it. She let me clean up, she went to look over her pile of paperwork.

That night I was sitting in my room, in front of my lighted mirror on my vanity, listening to Joni Mitchel, Julie Covington, Kirsty MacColl, something lite. Those artists reminded me of the kids. Linda liked podcasts, she didn't listen to music. She had to be learning something, even when she slept. She wore her headphones to bed, we never talked, that was her time for herself.

I had my hair up. I was taking off my makeup. I loved when the false lashes came off. I took hold with my delicate fingers, my long nails almost poking my blue eyes, and I pulled. I was de-glamming myself, I was still a woman in my mirror with or without makeup. I used a wipe and took off my lipstick, I loved the red on the white of the wipe. That was my color for a little while today. That is what made me happy, my lips, my white teeth, I smiled all day.

"You," I said to my reflection, "Are going out to dinner with a man." I smiled, I loved thinking about it. I couldn't tell Linda that my little 'clit' was so hard while we were drinking martinis with Logan. I couldn't tell her this was a fantasy of mine since, like, forever. I had told her almost everything else. "You are going to have fun again." I smiled, I used a washcloth and more wipes to remove the rest of my makeup, my cheeks, my eyes. I felt I was still beautiful, I felt I might even be beautiful inside too. My wig was on its foam head watching me, on its shelf, my real hair was in a high ponytail. I still had girl's hair, I still had my slightly curvy feminine body, my feminine look on my face. Lately, I was always female in my mind, even in my male clothes, I started taking low doses of estrogen. I was almost seven months into HRT and dressing up so much more. I smiled, I licked my lips, I played with my breasts in the black lacy bra.

Just the thought of being on a date, "Wait is this going to be a date? Is Logan taking me on a date?" I would get the courage, somehow, to ask him, just like I asked my reflection.

My long fingers went down to my little black panties. They were made of lace and silk. They were see-through. You could make out the little patch of hair hiding behind the lace. I started to finger myself. I always played with my 'pussy' like I was a 'woman.' It wasn't that hard to do, the mind was a very powerful tool. I started to push. Just the thought that I would be with a man, as his date, on the other side of a table was making me excited. Maybe he would tell his friends, the waitress, his mother. He would tell them he went out to dinner with a younger beautiful woman, a neighbor, a MILF who wore heels and big gold earrings. I started to shake, I started to push, I started to move my bottom. My ass was so round, my hips just slightly wider than last year, my body more feminine than it had any right to be. I licked my lips, I shook my ponytail, I watched my big hoops dance around my cheeks. "Oh no," I whispered, I started to cum, I pressed harder, I was cumming in my panties, my bench would be wet. I was shaking my vanity, a cup with my liner pencils fell over. I am always so surprised. "Ahh," I moaned. "Thank you for dinner, ahh..." I would kiss him goodnight. I would touch his chest, I would beg for another date. I would beg to be listened to. "Yes, yes, yes..." I closed my eyes, my hands left the panties, and started rubbing my breasts again.

I had a big smile on my face, this new frivolous 'woman' just had a marvelous orgasm and she wasn't even wearing makeup.

***

"Ugh, I was on the phone and computer all morning, the banks, Amazon, even work." Linda was busy this Sunday morning. "I can't wait to get to the club."

I was in a nightgown and a long robe. I had pantyhose hidden underneath, I had on three-inch heels, but still no makeup. I had been lounging all morning. "I hope you have fun." I smiled as I poured some coffee.

"And how about you, going to dinner with Logan. I hope you don't run into the ex-wife, ha." I looked at her, I think she was finally realizing I had a date, why else would she bring up his ex. They have been divorced for way over a year. She was sleeping with a relative, an uncle or cousin, or something. I only knew what Linda told me. I didn't really care.

"I'm looking forward to the restaurant. I loved that place, I love the decorations and atmosphere."

"Really? I can't even remember."

I was going to get dressed and made up after she left, I didn't even know what time we were leaving. I didn't even know if it was really going to happen. Linda told me all the things she had been working on this morning, all the bills and problems concerning the house and her work. She said she was working on things I wouldn't understand. She didn't even know why she was telling me. It sounded like she was complaining. I nodded, I looked interested. I felt my hair in the ponytail, I felt my stockings, I felt myself, in my little panties. I couldn't wait to paint my nails, pick out an outfit, brush my hair, tell her goodbye.

"Are you listening to me?"

I was daydreaming, "Oh, I am, I'm sorry. What are you doing next week?"

She told me she was going on a little golfing trip, Helene, her friend, emailed this morning. One weekend, two and a half days. She told me, she didn't ask me.

***

End Part 1 of 5