Five Fifteen to Long Branch

"Um, Wendy, come with me to the kitchen for a second."

I was leaning my ass on the counter, while she held her drink. She was looking at my outfit, I felt she didn't approve. "You have a girl's name?"

"I do, I have had it since I was young," I told her, I was starting to shake a little bit. I felt like I was about to be interrogated. "I'm sorry, I wore this outfit, I didn't know..."

"Wait, you had that name since you were young? I don't like that."

"You don't like my name?"

"Stop, I don't like that you have to have one, it makes this a little too real for me." She shook her head.

"But I need a girl's name if I want to be a girl."

She let out a sigh I could tell she was annoyed. "Just stop." She looked down toward my feet, "You are going to break your ankles on those heels," She looked at my feet.

I spun them around, looking at them from above. "No it has the ankle strap for support, they are fine. You don't like them either?"

"It's not that I don't like them," She said that, a little too loud, then she turned away from me I wanted to go back inside with Matt, who would be nicer. She whispered, "I just don't think my husband should be this sexy and have a girl's name, that's all." She took her glass and went back into the living room. Leaving me a little upset. I wanted to go back into my room and hide, but I wouldn't. This was me, hopefully, she would start getting used to it. Starting now. Hopefully, I could get through the night without apologizing again.

***

I let the two of them talk, I didn't want to get in the way. I kept myself busy in the kitchen, I was imagining that they were on a date and I was the perfect hostess. I filled up their drinks and brought them in some dinner. Matthew complimented me on my cooking, which made me smile.

I was cleaning up after they ate, Matt was watching me, "Wendy, we were thinking that we could have a happy hour every Friday, right out in our lobby. We could invite the neighbors. You could show off your outfits, show everyone how pretty you are becoming."

I looked at Loni, did she really think that. She added, "It will be fun, you told me you were getting too bored."

"And if you want," Matthew took my wrist and pulled me closer, "I could find you something to do, even some work if you'd like."

I smiled, I liked how he was talking to me. "Do you really want to do something Friday? Together?"

He now had both of my hands, "I do. We do, I will tell everyone. Five-fifteen until seven-fifteen. Not too long, just after work, you do drinks I will get the food. Okay?"

Loni stood up and released me from his hands. "Perfect, Friday, but maybe we can rethink this outfit."

Matt stood, "I better go, I have a conference call soon," He took my hand again and kissed my cheek. "I will be re-thinking about this outfit all night." He then kissed Loni, "Goodnight ladies."

I just stood frozen in the middle of the room, Loni closed the door and gave me a look, I then heard her head to the bedroom, "I'm going to lie down." I didn't see her for the rest of the night.

***

The Champagne Ginger Cocktail might not have had an aphrodisiac type effect on them, but on me, it felt like I was blasted out of the water. I didn't know where I was going to land. I stood in front of my mirror in my room and took out my headband, then took off my collar. I picked up my brush and fixed my hair, pulling one side back to show off my earring. I then put on new lipstick again, a dark red. I was shaking but for a different reason. I made a surprised look on my face, my lips becoming an O, my palm held in front of it. I picked up my phone and recorded myself posing in front of the mirror. I thought I looked incredible, Matthew did too. I had never had a man look at me like that before. I slid down my pantyhose, then panties. With a little flip, I untucked myself. I still looked feminine with my full skirt, no one would imagine there was anything but a little 'pussy' under the hem.

I practiced my conversation for Friday. "How may I help you?" I pursed my lips and kissed my image. "Would you like something to eat, something to drink, or something soft and squishy and sitting on your lap, ha."

I moved closer to the phone, and bent over, my breasts swaying in front of me. My D-cup breasts, I felt the weight, they were going to fall out of the corselette. I rubbed them watching my hands with my long fingernails fondle my breasts. I was a woman enjoying her body. I pushed my little 'clit' between my legs and crossed them. I felt my bottom rotate and my legs slide just a little bit together. I felt myself getting more excited, I felt the woman in me take completely over standing on her toes.

"Hi," I said into the phone and then into the mirror. "Do you like my breasts?" I giggled. I wouldn't say that on Friday. I stood up and played with my hair. My lips made the shape of my favorite letter again. I imagined I could feel the tiny bit of estrogen run through my body, I still couldn't believe I was starting this journey. I would love to tell everyone, a couple of calls or invite everyone over, I would love to show them the little vials I had in my medicine cabinet. "This I take every other day, but this, only once a week. Then I have to visit my Doctor for more." I would wink, but I didn't know why. I was getting more and more excited so I looked closer into my mirror. My nose almost touching it. My lashes were long, my eyes were blue, my lips left a print on the glass. Mwah.

"Tell me I'm beautiful," I told the woman in the mirror, and I started to breathe heavily, my tongue started to lick my lips. I started to come, one hand in my hair another on my breasts. I rubbed my legs tighter, my crotch was flat from the front, and I felt myself orgasm, my tiny 'clit' facing backward, and the cum start to slide down my legs. I scooped up the little I found on my calf and lifted it to my lips. I was shaking again. My fingers vibrated as the sperm touched my tongue. I was nervous, this was the first time I tasted a 'man's' cum. I sucked my finger, I watched in the mirror. I was suddenly happy but tired. It had been a long night.

"Thank you, baby," I told the image in the mirror, leaving another perfect lip print. I changed into a nightgown and took off my makeup, I then went to pick out another maid uniform for Friday. I started to wonder if Matthew was really going to think about me tonight.

***

This was a big year for me and was full of changes. I started to notice that Loni was getting angry at me very easily again. Just like before the big move to Long Branch.

The top three reasons were:

3: I dressed too sexy

2: She inadvertently blamed me for losing one of her friends

1: I gave away some of our money

The whole trans thing I thought she would get over quickly, but she was definitely annoyed more than ever by it. Wearing the sexy maid uniform instead of the one she had gotten me confirmed it. She was cold and condescending the next couple of days. I couldn't wait for Friday at five-fifteen so someone, anyone, would be nice to me again.

Number two and number three could probably be combined but I want to stay consistent. The morning after showing Matthew my maid outfit we got a call from our accountant. Well Loni accepted it, they talked for about a half-hour going over our finances, she didn't even ask me about it. Everything was fine, but it brought up the memory from last year. I sold my business for an exorbitant amount of money, more than I would have thought it would have gotten. I had to give some of it to my lawyer and accountant of course as commission. I didn't want to sell it, I was happy, I liked my work, I liked the building in Hell's Kitchen and the people I saw every day. My lawyer and Loni convinced me it would be a good move financially.

I wasn't good with money, I was more of an artist, I just got lucky with my business. I had eight employees, when the new company came in to take over I begged them to keep them all on. They told me no, so I gave each of the employees a million dollars. Eight million out of all that we had in the bank account, it didn't look to me like a big deal. I liked all of the people I worked with, they were friends, they were part of the reason the company did so well.

Loni was pissed. "You didn't even ask me." She yelled at me in front of the lawyer and accountant.

"I wanted to give them something, they would be out a job. I wanted to give them a head start." I tried to console her. She cursed at the three of us, left, and slept at her mother's for two weeks.

Soon people and relatives found out we had money, I was getting calls from uncles I hadn't spoken to in decades. I told Loni, and she was livid, but I didn't give away any more, except this once.

Loni was getting ready for work one morning, she seemed really agitated, this was before we moved to New Jersey full time. "Dorothy asked me for a loan. Can you imagine?" Dorothy was her assistant. They had been friends and associates since before we met. I'm sure she didn't even make twenty percent of what Loni made. "Why do people assume you have to pay for their friendship?"

"Maybe she really needs it. We have it."

"We have it. It is ours, no one said anything about sharing." She finished getting dressed and slammed the door.

I called Dorothy. I liked her very much, when she came to visit the two of us would talk in the kitchen while Loni and the other women from work would gossip in the other room. At those get-togethers, Loni didn't want me to bother her and her workers but I wanted to see Dorothy, I didn't get to talk to her as much as I liked, she was very busy. She was one of my favorite people.

Dorothy talked to Loni, she wanted to borrow four thousand dollars, she wanted to send her son to a performance arts school, but her ex-husband wouldn't chip in. When she asked me I didn't even question it, I sent her a bank check for twenty thousand dollars, it wasn't a loan it was a gift. I would have given it to her even before we had the extra money. I told her not to tell Loni, but she thanked her with flowers the next day.

When Loni came home that night she was screaming. She told me we were moving. "You have to get away from all the spongers and your fucking lousy family. We will have no money left by Christmas." We left West 61st Street. Sixty miles away from where we were now. She never talked to my lousy family or Dorothy again.

I still talk to her, I want to know how her son is doing. I didn't really care about the twenty grand or my lousy family.

***

I was standing in front of my mirror again, my favorite place in the world. I had just cleaned the whole apartment and taken a shower. I was dressed up just waiting for five-fifteen. Today was our party in the lobby on the ninth floor. Loni told me everyone was going to come. There were six apartments on our floor, four were occupied this winter.

I had on another sexy maid outfit, I had seen a crossdresser model this one on one of the costume sites. She looked spectacular, I hoped I looked as great as her. It was black with white lace on the collar and the hem. It was very short just reaching the tops of my sheer black stockings, lace around the trim. I had a pair of silky black panties and a matching garter belt underneath the little dress. I had on seven-inch heels with a two-inch platform, matte black with a perfect ankle strap. I'm sure Loni wouldn't approve of my footwear, but I felt the uniform was quite conservative, at least compared to the one she and Matthew saw me in the other night. I didn't show any boobs this time, the collar was right above them. I had on big gold hoops that reached my shoulders and a nice tiny gold watch around my wrist. I flat ironed my hair making it look longer and shinier than ever. I put a white ribbon through it. It looked very girlie. I loved it right away and took some pictures. I had on long red nails and dark red lipstick. I also had on long eyelashes and dark eye shadow, I looked mysterious. I couldn't wait to show off to the people on the floor.

I sent a picture of me in my maid outfit to Dorothy, I told her we should talk. A minute later she called. "Is that you?" She asked.

"It is."

"Why, what are you doing?"

"Well," I didn't know what to tell her, I didn't have too much time. I started questioning why I sent her the picture in the first place. "Dot, I think you are my best friend, I miss you." I sat down, I started to cry. Loni wouldn't let me talk to her anymore.

"Are you okay? Where are you, can I see you?"

I was still crying, "Things have changed, I don't know what I'm doing, I've been a little confused. I'm, a, transitioning to become a woman, don't be mad at me."

"What? Really? Why would I be mad? I think that's great, finally."

***

We made plans, we would talk. I had discussed this with her almost every time we got together. Sometimes she would meet me at work if I was depressed or if she was depressed, we knew how to cheer each other up. I wanted to tell her months ago, I wanted to ask her advice, but I started to feel like I should tell Loni first. I felt better after hearing her voice. She was so happy to hear mine, even though I sounded different.

I was now ready for the party, I went into my room to access the damage to my makeup, but I looked surprisingly fine.

I hardly ever went out on my own, but being right outside my door would be the next best thing. I would be out of the closet, so to speak, but not that far out of it. I could still see it when the front door was open.

I was posing in front of my mirror getting a little worked up, then there was a knock on the door, it was still early. I took a deep breath and opened it up. It was the first time I greeted a visitor as a woman.

"Hi, you look incredible." It was Matthew he was shaking his head with a huge smile on his face. "I was thinking we could set up the landing together."

"Okay."

He brought out a little fridge, filled with sandwiches. He had salads, condiments, and utensils. I could tell he had done this before. He let me set up the bar area. I had one on wheels and I brought it into the corner with his help. Besides the liquor, I had beer, hard seltzers, and cider. I had two bottles of wine and plastic wine glasses. I then had two pitchers, one filled with Sangria, and the other, Margaritas. I took my ice machine out of the kitchen and placed it on the smaller table next to the cups. I put on music, this party was going to be perfect.

Five fifteen people started leaving their apartment. We had them take out chairs and some snack tables. Everyone was on the landing. The elevator opened and Loni was amazed there were so many people. Matthew and I were serving everyone and they all loved my outfit. Matt himself kept touching my back or the skirt telling me he loved how it felt. It was making me feel so comfortable. After Loni was changed she sat down and I brought her a margarita. She said thank you and started talking to Mr. and Mrs. Sloan. I heard her call me her maid several times, but I didn't mind, I felt that was who I was to her now.

When Matt took me aside I forgot all about Loni, "Let's invite the staff from downstairs, they all get out at six. We can get some major points with the building," He laughed and we made our way down the elevator. I was a little nervous, I would be on display in the lobby for all to see, when I did this in the afternoon it was so much quieter. My heels, stockings, and the cute ribbon in my hair would be for everyone to see.

We walked out of the elevator, and Matt called over the man behind the counter. "Hey, Syd, Wendy, and I are hosting a party on nine, bring everyone up when you are done."

"That sounds great, love your outfit, um, Wendy?" He said with a smile on his face.

"That's me." And I took his hand. I was suddenly very happy and confident, we waved and went back upstairs.

***

Seven-fifteen was getting close and Matt and I were talking to the people at our table, all neighbors I originally didn't know the name of. Now I would have someone to say hello to. While we talked, Matt's hand was rubbing my back. he kept on smiling at me. Sometimes he would grab my hand. He was complimenting my nails, my legs, and especially my hair. He told me there was nothing more beautiful than a redhead. I lost my breath for a couple of seconds, I was loving a good compliment. We then started talking about our lives and I told the table I was a little bored, this party was a perfect distraction for me.

"We can have one every Friday." One of the neighbors mentioned, "I'll make empanadas."

"I'll bring the wine." Another one said. It was nice, it felt like a community.

Matt held my hand again. "See how easy it is to not be bored and be included."

"But what about the rest of the week?" I squinted my eyes and smiled at him, he moved even closer.

"I have my fingers in plenty of businesses in the area. Maybe you would like a part-time job?" He looked at his phone and rattled off a couple of positions he found. "Wait, here's one, this might be perfect, the perfume counter at Nordstrom's is looking for someone." He looked up at me. "What do you think?"

I didn't even think I just said, "Okay."

He made a call, smiling the whole time. All of us at the table watched him. "Monday through Thursday two to six."

I shrugged "Okay." And I giggled. I would be part of the workforce, I would be out of the house. I would be working as a woman.

When the time came we said goodbye to everyone, I couldn't believe how many kissed me or hugged me goodbye. I noticed Loni wasn't getting the same attention as me. We cleaned up and I put all my bar equipment and liquor back into the apartment. I took one more look and noticed Matt leaning back on one of the couches.

"Sit, and let's enjoy the afterglow of our successful party." He patted the spot next to him and I sat close to him.

I took out my phone from my apron, "I got a picture from my friend before." I showed him, it was Dorothy in a long red apron and high heels, "She said she was going to dust her unmentionables." We laughed, I thought she looked so pretty and happy. I needed that. She knew how to make me happy. I turned my attention back to Matthew, "Thank you for today. I had fun. This was so much better than just having drinks with Loni."

"No, thank you, it was great and you were very popular, heh. We make the perfect team." He grabbed my hand again and put it on his stomach. "I was thinking, would you like to go to Nordstrom's early on Monday, meet a couple of people, you know so you aren't nervous. I can take you."

"Um, okay that would be amazing if you did that. Are you sure you are not busy?"

"I can make time for a beautiful woman." He rubbed up against me. He was making me feel good.

"Loni doesn't like taking me anywhere anymore." I shrugged. and he smiled. "And we only have the one car, Loni takes it to work. I haven't driven for over a year." I giggled. "I'll have to come up with transportation."

"Well, this week it will be all sorted. I have a feeling neither of us will be bored." He leaned over and kissed my cheek. I felt I turned six shades of red. I waited until I turned back to normal, then we said goodnight, and I hid in my room and stood in front of my mirror. I had never looked happier. I stripped slowly in front of the mirror and posed in just my lingerie. I had on my bra, panties, garter belt, and stockings. My platform heels make me taller than the mirror. I would have loved to show Matthew what I had under my little maid's uniform. I rubbed my breasts together and made a surprise face, my lips looking luscious and kissable and in the shape of an O again. I would need to kiss someone soon. I thought about Matthew's kiss on my cheek, it was the only thought I needed. I put my hand on my panties and started playing with myself. I had never cum so much or so fast in my life.