The Fifth Date

The Fifth Date
By
Sarah Goodwoman

Chapter 1

Scott paced back and forth while looking at the cell phone in his hand. He was only a half hour away from having his fifth date with Monica and was making a big decision. He was either going to cancel the date or go through with it. He strongly wanted to enjoy the evening with Monica. He found her wonderful, yet knew that if they had their date it would end their budding relationship.

The fifth date always did. No matter how well he and the woman he was seeing got along there was never a sixth date. He did find solace in the fact it was not that he did anything wrong. In fact, Scott knew if he just kept his secret he could have had a sixth date with any of them.

Yet Scott did not regret never having a sixth date since college for he felt he was doing the right thing. He would tell his date his secret, he crossdressed. Scott felt it was not fair to a woman he wanted to be close to not to tell her. She had the right to know this fact before they got serious.

At first Scott told the women, but now he shows them he is a transvestite. He went from telling to showing his date because it was less painful for him. He only had to deal with rejection if he showed them. When he told them he also had to deal with the humiliation of them laughing when they thought he was joking.

Scott kept on looking at his phone and thought that Monica had to be on her way by now. He could still back out of the date, but he didn't know how to. He couldn't tell her the truth, that he feared her reaction to him dressing. He also didn't want to lie to her, she deserved better than that. She needed to know the real reason why there would not be a sixth date.

Scott couldn't take his eyes off his phone and suddenly it rang. He saw the caller ID appear on the screen, Monica. He was overjoyed at reading it. Yes! She is going to cancel the date and he wiill not have to do this. They will make vague plans to meet up again and just become ghosts to each other.

He answered the phone and cheerfully greeted her. Monica, in a sweet voice, told him that she was running early so she was wondering if it was OK if she showed up now. Scott panicked, he wasn't ready. Almost done with his makeup, he wanted a chance to make sure his outfit was just right.

Scott told her that he was not ready yet. She asked him when he would be. He wanted to say never, for one is never really ready for rejection. He told her that she could just come in, his front door would be unlocked.

Chapter 2

Monica was in a great mood all day. She had another date with Scott, a man she found wonderful. She joked to her friends that she could not decide what was the best part - that he was cooking lasagna for her at his house or that he was more interested in getting to know her as a person instead of getting her in bed. She laughed to herself for she knew the best part was Scott wanting to get to know her as a person.

She was so excited about the intimate dinner date that she left early for it. She figured it would not be a big deal to show up a little early. Then Monica thought that it would be considerate to call Scott. He might not be ready for company yet.

She walked into Scott’s house and announced she was there. Scott yelled down to her to get comfortable and help herself to a cup of pre-dinner coffee.

Entering the kitchen, she saw raw sugar and French vanilla creamer next to the coffee maker. She paused, for it put a smile on her face. Knowing that Scott drank his coffee black he must have gotten them just for her. That little deed of getting what she liked to add to her coffee just strengthened her notion he was a keeper.

She went to the living room and enjoyed her coffee while waiting. She thought about how perfect the night was going to be. Scott was impressing her the right way by being himself.

Scott told her to close her eyes as he was coming down. Monica asked why. Scott, sounding a little nervous, asked her to please humor him. She said fine. Laughing to herself, Monica thought that Scott must have gotten her flowers.

Chapter 3

Monica opened her eyes and saw Scott standing in front of her in a gray pencil skirt, a black T-shirt tucked in, and black heels. His makeup was done to perfection and his hair. Scott's hairstyle was tight curls. It fit his short round face and his outfit.

The only part of his outfit which did not flatter his look was the frown on his face. The frown on his face was more of a concern to Monica right now than the clothes. She had only known him for a month but she already deeply cared for him. She knew he was special. He was so much better than the men she had been dating before.

Monica asked Scott what was wrong. Scott sheepishly said this was their last date.

At that moment Monica knew one thing, that statement was the furthest thing from the truth of any statement she ever heard. She was not going to allow some pieces of fabric get in the way of her having such a good man. She asked him why.

Scott was ready for rejection so he was not prepared to explain the reason why. He expected her to give him any one of a multitude of reasons why. He must be gay, he was a freak, it is stupid for a man to wear women's clothes, he must stop dressing if he wanted to be with her. They all had one common thread, the woman not accepting him dressing

Scott told Monica she would not want to date him for he was sure she disapproved of how he was dressed. That he understood that she must be disappointed in him for not telling her sooner. He wanted to be upfront about his crossdressing, but felt that his dressing is something he did not want to share until he knew the person better. He understood that she would not want to have the fifth date. He just really liked her and had to show her why they could not be a couple.

Monica did not interrupt him once while he explained why he thought it was over. She felt so close to him right now for he was baring his soul to her. She found him strong for doing so. She knew most crossdressers never shared their secret with others. Their secret got revealed only when they were caught.

Monica told Scott, that she was disappointed in him. Those words instantly vindicated Scott’s preconceived notion about their relationship being over. Monica then went on to continue she was disappointed in him for even thinking it was over. She understood why he thought so, but she was not those other women.

Monica told Scott that she was not going to lose a great man because he liked to wear a dress. That she'd rather be with him than the men she had dated before. It was much worse to her for a man to blow off their date to hang out with his friends than him wearing a skirt. Monica then told Scott he better go check on dinner and asked if there was anything she could do to help.

Chapter 4

Scott did not know what to do next as he was in uncharted territory. The fifth date never went this far. He was expecting to have an argument with Monica. Then after she stormed out telling him to never contact her again, to cry and forget to take the lasagna out of the oven.

She was right, the lasagna needed to be checked. He got his bearings and told her she could open the wine to let it breathe.

They went into the kitchen and Scott was shaking a little. Monica could tell he was nervous and offered him a glass of wine. He smiled while accepting it.

There was a silence, Scott was scared of saying anything to offend Monica and Monica did not want to offend Scott with too many questions about his dressing. She did not know what to call it, calling it a hobby downplays it. Asking if it was sexual would be too personal, then again she hoped to find out if it was.

Finally, after another sip of liquid bravery, Scott said, “Heather.”

Monica quizzically said “Heather?”.

Scott then told Monica when dressed like this he referred to himself as Heather. Monica told Heather to go on.

Heather took another sip of the potion of bravery to help herself to continue. It did not work. So she said, “sorry this is stupid. You are here for a date with Scott, not Heather. I will take the lasagna out and quickly change while we let it cool down.”

Monica knew this was a delicate situation. She did not want to force Scott/Heather into saying or doing anything which is outside of their comfort zone. At the same time, she wanted to show she was open and accepting of the female aspect of his personality having such a prominent physical role.

As Heather was leaving to go get changed Monica said, “stay dressed how you are if you like. I think you look great in that outfit Heather, you have the legs for pencil skirts. I also need to know this side of the man I am dating.”

She paused for she thought she might have made a faux pas. Should she have referred to Heather as a woman now or female? It did not matter to her for that person in front of her is wonderful and she wanted to get to know them better.

Heather smiled after hearing the compliment on her legs. She knew she had great legs. They were long and slender. She always wanted to show them off and was happy that Monica noticed them.

Heather realized that she was so caught up being nervous about meeting Monica that she forgot to tell Monica how ravishing she looked in her peach bodycon dress. Heather responded with a thanks and told Monica how much her dress accents her curves and that the color went well with her skin tone.

Monica was relieved that she did not offend Heather by calling her a man. She also enjoyed the compliment, for the details in it. Unlike most men who just told her she looked great without being able to explain why, Scott always articulated on why. Worse. when other men did try to explain the reasoning was always sexually charged.

Monica asked Heather to tell her more about herself. Heather said that she would be more than happy to once she served them supper.

Chapter 5

Heather served supper and before Monica could ask any question, she blurted out one of her own. “What would you like to know about me?”

Monica saw that Heather was still nervous and told her to talk like she was on a first date with her.

Heather started to stumble around for what to say. She had no idea what she would tell a date. She never had a personal conversation with anyone as Heather, yet alone talk to someone who she wanted to get to know in a more personal manner. Heather just repeated the question.

Monica wanted to have a conversation and not turn this into an interrogation. She genuinely wanted get to know Heather and knew that if it just became questions and answers it would not help them connect. It would start to feel cold and formal. There was a good chance Heather would get defensive. Monica wanted a warm and inviting atmosphere to their chat.

Monica knew she had to be patient and understanding. Being a veterinarian she could read body language and could sense how scared and frightened Heather was. She did not want the silence to get awkward but also could not think of a question.

The silence was getting deafening in the room as they ate. Then it came to Monica she needed to take the lead on this date. Monica smiled and started to tell a story from her childhood about playing house. She hoped that Scott acted out on his feminine side when he was young also. At the end of the story she asked Heather if she ever played house.

Hearing Monica tell her about playing house brought back so many good memories from her childhood. Heather was lucky growing up, she had a sister, Stella, who was two years older and a couple of the kids on her street were girls. She was able to play with them.

Heather started to open up and told Monica about playing house. How Scott would make the girls let him to be the homemaker too. How Scott would love to have tea with the girls. How he would act like he did not want to but would play dolls with them.

Monica loved seeing the twinkle in Heather’s eyes as she was talking. She also noticed that she used her hands more to talk and touched her more. Scott was very personable when chatting with Monica, but it was in a different manner. She also was curious about why Heather would refer to herself as Scott in the third person. She asked her about it.

Heather had to think about the question for a moment for it was nothing to her to see her male side as someone else. She put her finger up in the air when she was finally able to articulate an answer.

“Monica, I am Scott. I refer to myself in the third person for even with us being the same person, I am different as Heather. When I was young I had to allow myself to let this part of my personality out. I wanted to but had to think about it. Had to think it was fine to do so. As soon as I thought it was fine I did not have to think about it anymore. Having allowed myself to be this natural part of my personality it just seemed right to refer to my male side now in the third person. I know I do not do it as Scott talking about Heather.”

Monica wanted to be part of the conversation, for it to have a natural ebb and flow, so she mentioned she thought it was good Scott was able be open about Heather.

Heather smiled for she was enjoying being able to share who she was with Monica. She wanted Monica to know all about who she was, both as Scott and as Heather. She knew that this chat they were having would bring herself and Monica closer to each other.

She told Monica that she did talk some to Stella about Heather. Stella was the first person to catch her dressing. Heather told the story about Stella catching her dressed. She was lucky that Stella was not upset at seeing her kid brother in her clothes. She did not like the outfit he had on and thought he had no sense of fashion. Scott explained that he just wanted to wear the clothes and did not take the time to put an outfit together.

Stella laughed and told him to so now if wanted. Scott did and Stella was impressed with his style. Stella did impose one rule, he had to buy his own panties and bras. While she would actually buy them he had to give her the money for them

Heather then told Monica about his parents knowing but not approving of Scott’s “hobby”. She did not like that they referred to it as a hobby. How can wearing what you want to wear be a hobby? It is just following a social norm. People wore clothes even when alone. Heather did laugh when she mentioned one great thing about dressing is it did stop her parents from making unannounced visits. Her mom and dad did once when Heather was dressed to the nines in what she would have worn to the prom.

Hearing about the prom made Monica think about Scott/Heather’s sexuality. She knew that there was no correlation between a man who crossdressed and their sexual orientation yet she was concerned that 'Heather' might be straight. She knew that concern was probably unfounded: yet it was real so it had to be dealt with. Knowing that she could not come right out and ask Heather if she was straight or a lesbian she asked her who would have been her perfect prom date.

Heather’s face perked up hearing that question for she was spending time with the person she thought would be her perfect prom date. She quickly responded to Monica's inquiry. “A woman who is kind, caring and can bring me out of my shell, in other words, you.”

The quickness and sweetness of the answer along with the conviction in Heather’s voice made the worry Monica had about Heather baseless. That answer also made her realize that she loved Scott/Heather. She knew that she had strong feelings for him but the love was confirmed by how good she felt hearing that answer. She had a warm feeling inside which felt like home.

Chapter 6

“I love you!” Monica proclaimed .

Heather's eyes watered up with tears of joys and tears of relief. She had dreamt of hearing someone as special as Monica saying those words to her, but never dared to put much details into those fantasies. The vaguer someone's dreams were, the easier the letdown would be when they never became real. As tears started to roll down her face she told Monica she loved her back.

Monica went over, hugged and kissed Heather. She thought to herself, this is the first time she kissed a woman. She thought of how tenderly Heather kissed her compared to Scott and was pleasantly surprised at how much she enjoyed it. Monica later thought she was lucky, she would get both kind of kisses from her boy/girlfriend.

After the kiss Heather wiped away the tears from her face and said, “oh no, my makeup is ruined. Let me go upstairs and change.”

Monica told her she did not have to, her makeup was not that bad and Heather should be able to easily fix it.

Heather smiled and replied back “That is true but everyone knows you end the first date with a kiss and Scott deserves to finally finish a fifth date.”



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