Six-Month Anniversary

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A Crossdresser gets a little sidetracked on her Anniversary.
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Six-Month Anniversary

By Sabrina G. Langton

***

(The same dress through the entire story... I'm not used to this... Hope you like it.)

***

"I'm sorry our plans had to change, but are you sure you want to wear that? Don't you think you are going to stand out in that dress?"

Marge and I have been dating for six months and she promised to take me to my favorite restaurant for dinner and drinks, Tuscany 22.

"Are you sure you don't want to go to Rubies? You can wear that nice pink latex one I bought you."

***

I met Marge after I went to a transformation service in Downtown LA. I have been a crossdresser since I was young but when I turned twenty-five I wanted to go all out, get dressed up, and go somewhere I could interact with others. I was getting lonely being by myself in front of the mirror and computer screen. Marilyn's was a place where men came to dress as girls and get to go out to a nice safe place for the night, drinking, dancing, and looking fabulous. I wanted to look fabulous. Marilyn and her stylists took us to Tuscany 22, a quiet restaurant with a party room in the back.

"...and what did they do to your hair? You look like a weather girl."

I let her watch me play with my long red locks, they were extensions. They weren't poofy or curly, just a little height at the top and they landed nicely on my breasts. Marge didn't really like how I dressed and presented myself as a woman. When we met I was wearing a beige dress with brown stripes in strategic places to give the illusion of a curvier body. I also wore my four-inch black pumps and nude stockings. My makeup and red wig were perfect, coming directly from the salon. When the seven of us got to the restaurant we went into the back where a bar was set up. There were already people drinking and I was happy to be out, it was my first time at a bar as a 'woman.' Besides the seven of us from the salon, there were so many guys and a handful of women. I was hit on by women and men most of the night, I was totally enjoying myself. Marilyn told me I had legs that would drive a man crazy so I made sure the hem of my dress was high all night. It was also the first time I was in the company of other crossdressers and their admirers.

"You know, if you walked into Rubies wearing that outfit they would think you were there to collect the rent, haha."

Marge told me she saw me walk in, but I didn't notice her until the end of the night when Marilyn and her staff were ready to leave. I was sharing an expensive bottle of Australian Malbec with my friend Antoinette and two men. We exchanged numbers with them, I felt so sexy. They treated us like women all night though I knew, they knew, about Marilyn's girls.

"...and that perfume you are wearing, I definitely didn't buy it for you."

Marge very rarely wore perfume but when she did she wore something called TomboyX and she liked when I wore something that smelled like cotton candy. She was definitely a tomboy, me, I definitely wasn't cotton candy. I liked 'Chanel Chance' which was always my signature scent, I always wore Chanel even when I was a teenager. My mother couldn't understand why my clothes always smelled of it, I lied to her that I had a girlfriend.

"Let me see those nails again."

Marge took my hand, she was getting a little frustrated, but I was nicely dressed and waiting to go out to dinner. I didn't rush her at all. I had on sensible shoes and comfortable lingerie. I bought my bra at J.C. Penny. I had gone to Marilyn's Salon again and was prepared to be a woman for the next three weeks. I had a vacation from work and I was excited about wearing only female clothes for an extended period. I didn't tell Marge about that.

"These are so long, and who wears red anymore?" She asked me.

"Well they go with my dress, don't you like them?" I showed her both my hands, long nails made me feel so feminine. Marge didn't like them long. She liked nails short and black or pink depending on what type of outfit she was putting me in that night. "I love them, they look so nice running through my long hair." She didn't like me with long hair either, she would make me wear my wig with pigtails or a short blonde or black bob. My own hair was red and that's what I liked. I liked to look like your regular average woman, Marge didn't. When we first met she said she was molding me into something better. She was older and wiser, and she was so nice to me I let her take me home.

***

Tonight was supposed to be our anniversary dinner, Marge told me she would take me anywhere I wanted and I picked the place we met. I was very excited. It was just a regular restaurant on an average street in LA. Marge only took me to Rubies. Rubies was her local, it was a dark bar usually filled with lesbians and some trans men and women. She would dress me up as her 'little sissy' and prance me around the club, then leave me in the corner. She loved to watch me get hit on by all the bigger women, but she knew I was too embarrassed and nervous to go out with or even talk to any of them. When we first met we only hung out together in her apartment, but as time went on she tried to get me more involved in her sissy games and brought me more into her world. She was training me to become the type of man she liked. Unfortunately, I wanted to become the type of girl I liked.

I was standing in front of the mirror, I had on my C cup breastplate under my red leather dress. They looked perfect. The dress had short cap sleeves and the neckline was high. The hem came halfway between my panties and my knees showing off my tan pantyhose and then my three-inch red heels. They had an ankle strap and my red nails were peeking out the front. They were very feminine. I liked them so much better than the mary-janes Marge would make me wear. Sometimes she put me in pink sneakers, but I wanted a bit of height, heels made my body look so shapely.

Marge owned a wine bar, Margarine's, on the same stretch of storefronts where Rubies and Tuscanny 22 was. She got busy at the last moment and then someone called in sick, so she had to go in herself and take care of things. She told me it wouldn't be all night. I wanted to move our plans to tomorrow but she knew how much I was looking forward to this. She just didn't expect me to look all femme from the salon. She didn't like when I went to Marilyn's, I usually had to dress under her watchful eye. I wanted it to be a surprise. She was surprised.

I was brushing my hair waiting for her to get off her phone. I could tell she was staring at me from behind, she was a little disappointed in my look. "Okay," She told me, "My ex is going to meet you and take you to Rubies, they will hang out with you until I get the chance to finish at work."

"Rubies? You said I wasn't dressed for it."

"Yeah I know, just sit at the back bar and hide, I won't be that long."

***

When we got to Margarine's it was packed, Friday was a popular night.

"Now sit here," She pointed to a stool that looked out onto the street. "And I will have them come and take you out." She then went in the back to cook, serve, and manage.

I had my legs crossed sitting on the high stool and I felt I looked very sexy and very passable. I never came to Margarine's dressed as a woman, Marge wouldn't let me. I could tell she was avoiding interacting with me and she was leaving me alone to get on with the night. She told me her staff figured she was gay and if I came in as 'Sabrina' then they would know for sure. She loved showing off my male self to her staff instead. Marge was a little complicated.

I was drinking their house red, the waiter was being so nice to me, and I was people watching out the window. A man stopped and took my picture through the glass and then came in and asked for my number. I was very flattered, I gave it to him. My phone buzzed and I read the text from Marge, someone was coming to get me in ten minutes. I couldn't wait to see everyone in Tuscanny 22.

Sitting here I knew Marge was uncomfortable with me looking too much like a girl and not enough like her plaything.

I was caught up in the street action watching people get on with their night when I felt a tap.

"Hi. Sabrina right?"

She was a beautiful Asian woman in a short blue dress with a clutch bag and red heels. She smiled as she peered down at mine.

"Oh I love your heels, ha, we almost match." She seemed very nice. "You are Marge's girlfriend, right? I have seen pictures of you on her Twitter."

"I am," I told her and took her pretty manicured hand.

"I'm Felicia, can you believe Marge and I once dated too? It's crazy to think of it now." She laughed. "And now you, maybe she has a new favorite type. Hot looking women in red heels, haha."

I liked her right away, she was very bubbly and the two of us giggled the whole time we were together.

"Is this your spot for the night?" She asked me, "Or do you want to get some real drinks?"

Margarine's was usually where the clubbers started and then made their way down the rest of the block. I was glad Marge had gotten Felicia to take me out with her, I was afraid I was going to end up hanging with one of her tougher-looking exes. I felt most of her friends didn't like me, as either gender.

"Oh no. I am so ready, let me just tell Marge." I went to the cashier to pay my check and tried to get Marge's attention. She waved me off not even getting off her phone. I guess it didn't matter, I'm sure she will know where we were going.

Once we were on the street Felicia checked her phone. "I just have to meet my boyfriend first, have you ever been to Studio 12?"

"I haven't but I always wanted to go."

"Good, let's go show off."

We passed by Rubies, it was dark and unassuming. They had Micalobe Ultra specials, I actually hated going in there. They had a huge courtyard and the only thing the customers did was smoke. My little girl dresses would smell even after I had them dry cleaned. Next, we came up to Tuscanny 22. That was my favorite. Marge's friends wouldn't be caught dead in there. I loved the food and the staff loved me, I haven't been inside for a month. The last time was when I went with the salon and the CDs again, it was my third time but I knew everyone's name in a minute. As soon as Marge found out I was inside she left work and dragged me out of it. She made me change out of the plaid dress I just bought and put me in something less revealing. We spent the night at Rubies.

"Here we are." Felicia headed inside. We walked past people waiting on line to get in. She kissed the doormen and introduced me to them. "This is Sabrina, doesn't she look fabulous?"

"She sure does." One of them took my hand and started asking me all sorts of questions, I was liking the attention but Felicia dragged me into the light of the club. I waved back to the doorman before the door closed.

The music wasn't too loud and it wasn't that dark, I loved it immediately. The room was filled with women in designer outfits and men in nice suits, I felt I fit in. Men watched us as we breezed by, I think they all knew Felicia. We were heading to the bar in the back when suddenly a huge man grabbed her and lifted her off of her feet. They kissed, he was more than happy to see her.

She turned to me after he gently put her down. "Sabrina this is Mack, Mack, Sabrina."

He took my hand and kissed it. "Another one of my girlfriends' beautiful friends."

I just smiled and whispered, "Thank you."

The three of us sat at the bar and drank martinis, I loved crossing my legs sitting on the high stool. I was begging anyone to check out my legs, I wanted to drive someone crazy, at Rubies no one even looked at me. Marge just made me hang out with the other sissies. We all wore an over-the-top frilly dress with so many petticoats. It took me forever to tinkle, especially if she made me wear the plastic cock cage.

Felicia made sure she introduced me to everyone who walked up to her, she was very popular and I vowed I would remember everyone's name. That was my thing. She told me, "You know if Marge finds you here with me she is going to be quite disappointed in her little girlfriend. Does she ever let you off of her leash? She never let me."

"Very rarely but this is a special occasion, it's our six-month anniversary."

"Wow six, I made it to about eight, ha. When I met her she said she was going to teach me to be a better woman." Felicia laughed.

"That was one of the lines she used on me too."

"And look at us. Are we better?" I knew in my case I was, but Felicia was so beautiful and feminine I couldn't believe she was male or used to be. Marge told me she only dated men, even though they had to look like women.

"My voice and confidence are so much better," I told her.

"Good, because I want you to meet someone. I want your confidence as high as your heels." Just then a man walked over to us and kissed her. He was tall and seemed quite confident himself. His name was Marcus and his hands were so big. My fingers looked so dainty when he took me in his grip. "Marcus, Sabrina's date stood her up, she is looking for some company."

I looked up at him, would he keep me company? He didn't seem like the type of man I usually ran into when I was dressed as a woman. If I was in Rubies all the men were overly feminine and their mannerisms were over the top. Marge wanted me to learn from them. If I was at Marilyn's salon, the men were usually gay and they always complimented my makeup and dress. Only the crossdressers were straight, or at least some of them. But this was something different, I was in the presence of a man.

After we got acquainted Marcus asked me to stand, and we headed to a table in another section of the club. Before we got there he spun me around, I was in his arms.

"Could we have a quick dance?" He smiled down at me.

"Mmm, okay." He put his arms around me and I instinctively put mine around his neck. I could smell the soap he used and it was suddenly intoxicating.

"Felicia told me I was going to meet a beautiful woman tonight."

"She did?" I started to look around, maybe I was just keeping him warm for her.

"She told me she knew a redhead that didn't get out much. Don't you want to show off to the world?"

Was I the redhead? Was he calling me beautiful? I loved compliments but didn't know how to accept them. "I do," I told him as I bit my lip, and I held him a little tighter.

I looked around, other couples were dancing to the quiet music, a man winked at me when I smiled. I closed my eyes I wanted to enjoy this. Marcus's hand went a little lower, I was wishing I was wearing a thinner dress. I had so many, I had a closet full of them. I decided on my red leather one because Marilyn suggested it. I brought six dresses and six pairs of heels to the salon. She knew I wanted to look perfect on the first day of my three-week vacation. None of the outfits I brought have ever been out amongst people, only my apartment mirror. If it wasn't for the anniversary I would be wearing something uncomfortable. I was totally comfortable in a man's arms.

The music stopped and we clapped. He bent down and kissed my cheek. I looked at him and put my long fingernails on the spot he kissed. I was a little surprised. He gave me the greatest grin and then led me to our table.

He asked me what I would like to drink, but I couldn't think. I was a little worked up. I wasn't used to someone paying attention to me, plus being so close to a man was making me too excited. "Um, something red, to match my dress?" I was being cute and he laughed. He told the waiter he wanted a bottle, he gave him a year, it sounded expensive. I was so going to love it.

When I went to Rubies, Marge would make me drink something pink to match my outfit. It was always all fruit punch or lemonade. I wanted something stronger, more adult. I was an adult. Sometimes she would make me lick a lollypop, she wanted to give my tongue a workout. I knew there were better uses for a tongue and I licked my lips while Marcus watched, we held hands again until the waiter came back with the wine.

"What should we toast to?" He asked me. "Should we toast to your six months with Marge?"

I forgot all about her, I was suddenly hoping she forgot about me. I haven't checked my phone all night.

"Can't we toast to us?" I asked him, a sly smile on my face. I felt my heels against his leg. We toasted and he laughed.

Felicia was back with her boyfriend. "Hey, you two can I borrow Bree for a sec?" Bree? Was that me, I loved a good nickname especially a sexy-sounding one. Marge called me fancypants, which I hated. I couldn't tell her that cause then she would use it more. I didn't mind her calling me Sissy, but at the bar, everyone was named that. I was just one of the crowd, I wanted to be someone special.

"Don't take her away for too long." Marcus stood as I did and kissed me on the cheek again. Mack sat in my place as we headed for the ladies' room. I glanced back and Marcus was still watching me, I gave him a little wave and Felicia laughed.

"Someone is having fun I see."

I stopped before the restroom with my hand over my mouth. "I am. I think he likes me."

She giggled as we walked into the bright ladies' room, "Every man likes you, look at that goddess in the mirror." We stood looking at each other's reflection. She was a perfect woman I couldn't even compare to her, she was totally a goddess. If it wasn't for Marilyn fixing my eyebrows and lashes I don't think they would of even let me in here. I tinkled and then went to fix my hair, my makeup was still perfect.

"Mack and I are going back to our place, want to tag along?" Felicia was painting her lips.

"I do. Do you think Marge will mind?"

"Mind? She is gonna freak. You can just tell her she shouldn't of let you out of her sight."

I was having such a nice time, and it was still so early. I decided I still wasn't going to check my phone, I was all in on whatever Felicia decided tonight. "Will Marcus come?"

"Where you lead he will follow, little girl."

The four of us sat at the table finishing the rest of the incredible wine we were drinking. I touched Marcus' hand, "The wine was so wonderful, I will always remember you introducing me to something I genuinely love."

He smiled at me again, he then bent down and kissed me. I was startled. His lips touched mine and I suddenly felt his tongue enter me. I was hoping Felicia and Mack were watching. We pulled back as the two of them stood up. Marcus then kissed me again. I started to get flushed and my heart was racing. Hopefully, we could do more of this at Felicia's.

***

We walked a block west. Felicia and Mack's apartment could be seen from all the bars and clubs on the main street.

I was standing at the window looking down at Tuscanny 22, Marcus was behind me. He pointed out his apartment, it was three blocks away.

We were sitting together on a red and black couch. My dress matched and I told her it looked like I was waiting for service at Auto-Zone. She laughed and told me Marcus was probably going to get my motor running anyway.

"First I will have to check her maintenance report." We laughed and I leaned into him.

Mack made coffee, and Felicia showed us her apartment. It was beautiful, nicely decorated, and had wonderful paintings on the wall. Before we went back to sit down Marcus put his arms around me.

"Mmm," He said as he held me against his body.

He was turning me on, it was crazy how sexual it all felt, even just walking next to him. "You smell so good," I told him. I meant it but I felt like a little girl saying these things to him. He was a man. I needed to come up with better lines, Marge didn't teach me to become a better woman she taught me to be a better sex partner for her. I wish I spent more time with Marilyn and her girls I would have learned so much more.

12