Why Haven't You

Author's Notes: This is a stand alone story which use some of the characters from Why Not. You do not need to read Why Not to enjoy this story. While enjoy it as much as someone can enjoy what I write.

Lizzy Potter was a little excited for her third date with Dale Kelso. The hopeful lady was thinking he could be the one, Mr Right. Not the perfect man, or even the man she dreamt of when she was young. A man who could fit those monikers was would fulfill her desires but the wise lady was content to meet her needs. Her date for the night could be the man who she could grow old and have a good life with. The wise lady knew that sometimes you needed to not let the perfect be the enemy of the good. So with Dale being able to provide what she needed, lized convinced herself he was actually Mr Right.

Lizzy’s phone rang just as she was done getting ready. As she went to answer it she saw it was the man who was courting her. “He must be early” the optimistic lady thought. Her voice echoed her good mood when she answered the phone with “Hey there Stud.”

Dale sounded excited when he replied “Hey babe, great news!”

Lizzy’s bar of expectations was raised by hearing the happiness in Dale’s voice. He might just turn out to be better than good enough. Of course, this was real life and not a movie. People start to put the relationship in front of their needs the longer they were in it. It does not happen right away like in the world of fantasy. Dale will grow as a person and be more well balance.

Lizzy flirted when she said “do tell.”

“While babe, it is awesome. Heath scored two tickets to see the Cavs play. I am so wearing my LeBron jersey. So rain check on dinner tonight. We will do it some other time.”

With those words Dale did a Fosbury Flop right into Lizzy’s bar of expectations and sent to crashing to the ground. To her surprise she was not that devastated only a little disappointed. The disappointment was in herself and not Dale standing her up at the last moment . She let herself down by having that one night stand with a guy in her circle of friends. Then, to make matters worse, she decided to see if it could work out between those two. She lied to herself and saw Mr Right Now as Mr Right.

Lizzy’s tone also drop to where her expectations were when she said “OK”

Dale was oblivious to the change in Lizzy’s voice. It was for the man was too happy about going to the game. “Cool Babe, I will call you to set up dinner. Bye.”



Brad Gratton just finished putting on that cute skater dress he bought today. The crossdresser knew he did not need it, but he deserved a treat. Plus it went great with the floral design pumps he had. That should have been an excuse enough. It also helped to better justify him splurging on shoes which he never wore out of the apartment. There was now two outfits those shoes were perfect with. He did laugh to himself that he felt better about a frivolous purchase by making another one.

He sat down to a glass of white wine and was ready to have a nice relaxful evening at home. It was the perfect atmosphere for him. The lights were dimmed, a couple scented candles were lit and the man in a cute dress was going watch some Law & Order: Parking Violation Unit. It was going to be so nice.

Brad so loved his me time, it was when he could feel pretty. He used to think it was silly, but then thought how other hobbies men have were also silly. A grown man going to a game wearing a sports jersey with someone else’s name on the back was just as silly, if not more, than him wearing a dress at home.

The phone rang and he saw it was his friend Lizzy Potter. He found that a little odd for she should just be being picked up for her date tonight with Dale. The man, who was always there for a friend, was hoping for the best but expecting the worse when he said “Hey there Lizzy.”

Lizzy felt bad on the other line. It was not right to call someone on the last second to hang out just because you got stood up. If Brad was not such a good friend she would not had called him. He was a sweet guy who was there for the people in his life. Lizzy was unsure of if she was overreacting to Dale’s decision to cancel the date at the last moment. She felt like it was not right so she started to abort what the call was about. “Sorry Brad. I should not had called. I will see you tomorrow.”

Brad knew what was going and wanted his friend to say what was on her mind. He knew being straightforward would not work so he just acted like her plans were still on “Never say sorry for calling. Sometimes a person just needs to hear a friendly voice. I hope you have a great time on your date tonight.”

Lizzy knew her friend was saying he was there for her and talk to me. “Come on Brad, you know something happened with the date and that is why I called. I should not had, I can handle it. See you tomorrow.”

“Come on over in an hour and we will just hang out and talk. Come on I am doing nothing.”

“Brad, you are having me time. So you are doing something, you need not to change your plans for my self-made drama.I see you tomorrow.”
“Lizzy, me time is doing nothing. I am just relaxing and I can also do that with you around. In fact your presence is always relaxing so some on over. All I ask is for you to bring over a bottle of white wine. I do not have enough for two people. See you in an hour.”

Liz, knew her friend disguised a friendly command as in invite.. If she did not show up, Brad will bring it up and they will talk about what was on her mind tomorrow night with their friends. So she got changed and went over to his place.


Brad hurried up and got himself and the apartment back in male mode. As he came back into the living room from his shower dressed in jeans and a t-shirt he saw the the lavender candles. Brad cursed himself for not paying attention to details which he deemed not important. The he thought it was no big deal the place will have a calming smell for Liz and she had other things on her mind.

As liz walked into the apartment she said “Hey Brad, thanks for having me over. I swear I smell lavender.”

Brad laughed and played it off“Yes, you caught me. I like scented candles and had one lit before you came home. Now you know what I do during my me time.”

Lizzy laughed while requesting him to light them. Then again Lizzy always laughed when Brad joked around for he knew how to ham it up. While hearing the lady with man problems show she was getting in a better mood the host offered his guest a sit, got the candles out then lit them and pour them both a glass of wine.

“Again, Brad sorry for coming over and bringing you into this little mess I have. I will get straight to the point so we can enjoy the evening together. Am I overreacting to Brad cancelling the date on me.”

“You can see it as him cancelling the date, if I were in your shoes I would see it as me being stood up. By the way, love the shoes.”

Liz shook her head and laugh at the ham’s comment about her shoes then asked why.

“It is simple, you two are in a relationship so your plans together should have taken precedence over a last moment chance of doing something else. It made it so he was wasting time with you not spending time with you.”

“What should I do? I mean he is good enough for me and other than a couple of flaws a nice guy.”

Brad took a long sip of his wine as he tried to find a tactful way of not answering the question. “Hon, you make that decision, not me. I will back you either way, for I want you to get what you desire.”

Hearing Brad’s non-answer helped Lizzy find what she was looking for. Brad was right, she should go after what she desired rather than what she needed in a relationship. She did not need a relationship to be whole and happy.

So with her being done with Dale and having the renewed conviction of going after what she desired she asked Brad "Why haven't you asked me out?"

Brad took another long sip of wine, this time for he did not want to tell the truth. He only dated ladies who knew about his hobby at the beginning of them knowing each other. “Come on Liz, we are friends. Your friendship with me means more than a date. I am in the friendzone with you and happy to have you in my life. You know that Men and woman can have healthy platonic relationships.”

Amy said“Now you come on. We both know we like each other in that way, yet you never asked me out. I think I deserve a better answer than that. Plus you said you would help me get what I desire. I desire a relationship with a man which is like our friendship. I desire a man like you to share the rest of my life with. So, why haven't you asked me out?”

Brad blushed hearing that. He laughed to himself for he knew that the color of his cheeks were now the same as they were earlier tonight when he was all dolled up. “I just do not think, I am the best man for you.”

“You can do better than that, come on. We are always open and honest with each other. It will not hurt my feelings if it is something superficial about me. Please tell me why haven't you asked me out?”

“Oh, no, no, no. It is not you. It is me, all me oh it is all me. You have to believe me when I say it is all me.”

Amy started to rack her mind about what it could be. Nothing came to her. “Please tell me, why haven't you asked me out. I promise not to laugh.”

“Oh you will laugh, so I will not hold you to that promise. I will never make you promise anything anyways to tell you something. I would share something with you for I am comfortable with you knowing that about me. I am not comfortable with you knowing why. It will change how you see me.”

“Brad, it would have to be something major for that to happen. You are too good of a person for me to change how I see you over something trivial. I will drop it after asking one more time, why haven't you asked me out?”

Brad took his time. He did trust Liz not to tell anyone about his hobby and she needed to know why yet another man rejected her tonight. It would help his friend’s ego if she knew it was not her. “Ok, I like to crossdress.”

Liz laughed and Brad was a little hurt. Liz quickly said “Oh I am not laughing about you crossdressing. We all know that you do. While at least you like to wear women’s panties. A couple of times you wore them while out with us.

I don’t care. A couple of the friends make fun of you about crossdressing behind your back and I tell them to shut up. That is so childish of them. But I am happy that they do for then I know I do not want to be as close of friends with them.

That is no big deal for me. You are a great guy. You make me laugh feel better about myself, No wait, we make each other laugh and feel better about ourselves. You are dependable, there for me when I need you. No, Not only me but anyone. I try to be as dependable as you.

So now tell me why you do not ask me out now.”

Brad this time laughed at him not paying attention to details which were not important and wondered how many times he went out in panties. Then Brad got a serious look on his face at said “No, I will not. Instead I will ask you this; can I take you to out on a date to a nice restaurant next Saturday night.”

Lizzy wondered for a second why not tomorrow night and then it dawn on her, they had plans to be with their friends. That made sense Brad. would practice what he preached. “I would have to think about it….. Of course, hahaha.”

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