Urban
patreon
Dress Code - Dare To Wear Dress - Chapter 16
🕑 Added 2025-01-02 13:20:04 +0000 UTCOTHER CHAPTERS | ALL STORY LIST
I was born and raised in Big Spring, and after high school, I joined the Navy where I was an ASROC gunner mate. It took presidential authorization to fire a rocket.
How cool is that? After a few odd jobs here and there where I learned how to be an expert at Excel, I wound up here.
Now you.” I smiled at Jimmy before looking back at my brisket.
I said, “I’m not quite so colorful. I was born and raised in Wink and graduated from Angelo State and Xantek picked me up mostly because of the websites I developed as a contractor. That’s about it.”
Jimmy set his sandwich down and leaned towards me. He asked, “But how did we get to Heather?
Yeah, I know about the bet and all that. It was crazy for you to accept such a bet, but let’s face it.
You, Heather, are a far cry from some nerd trying to survive wearing women’s clothes, much less be passable. No, you’re not just a guy in a dress. You’re a woman and I’m having a hard time wrapping my head around that.
I talked to Ann and she told me that before the bet, you were just some dweebish, quiet guy who, though mortified, managed to ask every woman in your office area, single or otherwise for a date.
So apparently, you were a normal guy who liked girls.” Putting my fork down and frowning, I said, “You’ve been checking up on me? That creeps me out.” Jimmy held up his hands defensively and said, “Hey now. I’m not a stalker or anything. I find you fascinating.
I mean, you completely changed sides and I just can’t grasp how that’s possible, and as a guy, the thought of having my penis removed…” his voice trailed away and he shuddered. “My penis is just fine, thank you.
I think we’re done here. Please take me back to the office,” I said sternly.
Shaking his head, Jimmy said, “I’m terribly sorry if I offended you. I just find you very interesting.”
“I had to deal with one of you so-called admirers right after I became Heather, and he damned near made me lose all interest in men.” Jimmy smiled and said, “That’s an interesting thing for you to say. Look, I’m not one of those admirers, whatever that is.
I’m a straight guy and I like women. You seem to be a very special kind of woman. A kind of woman that’s perfect for me.”
I set my purse on the table indicating I was ready to leave. I said, “Oh? And how is that?” Jimmy smiled nervously and said, “If you haven’t noticed, Jennifer likes to talk.
She told me in strictest confidence that the reason you broke up with your last boyfriend was because he wanted a family and you of course can’t provide him with one.” Scowling, I said, “I’m going to kill her.”
“I just broke up with my girlfriend for much the same reason,” said Jimmy as he looked like he was about to tear up. “She wanted babies. My babies. And I can’t give her, or any woman a baby.”
I relaxed a bit and said, “Oh? Why not and why are you telling me?”
Jimmy laughed and said, “You’ll just hear it from Jennifer. I’m… um, I’m impotent. I just feel it isn’t fair for me to date a woman who expects to have a family one day.”
I just looked at him for a moment.
I said, “That’s a treatable condition, right? If nothing else, you and your girlfriend could go to a fertility clinic.” Shaking his head, Jimmy said, “Ex-girlfriend. My sperm count is just too low. I’m basically shooting blanks.”
This was increasingly awkward for me. I said, “I can’t believe I’m sitting here listening to a man I’ve only recently met tell me about his sperm. During lunch.” Jimmy’s cheeks reddened.
He waved a hand in a surrender gesture and said, “You’re right. I’m very sorry. I didn’t intend to talk about my sperm. I actually feel so comfortable with you, that I just sorta blurted it out.” My eyes widened and I angrily said, “Will you please stop saying ‘sperm’?”
“Okay, okay!” Jimmy said. “I won’t say ‘sperm’ any more today. Let me finish my sandwich and we’ll go.”
“I’m sorry he made you uncomfortable, Heather.” Ms. Rogers sat calmly at her desk and just studied me. “But his project is very high profile, and you’re the best woman for the job.”
“Really?” I said, feeling shocked. “How can I work closely with someone who casually talks about his sperm?
Ms. Rogers, I’ve spent my whole life without ever having a discussion about someone’s sperm.”
Looking amused, Ms. Rogers said, “You suddenly seem to be obsessed over Mr. Garrett’s sperm.” Waving my arms in frustration, I said, “I don’t care about his sperm or lack thereof. I was embarrassed and offended by him singing it up when we were supposed to be discussing the project!”
Ms. Rogers said, “If he brings it up again, just let him know that this is not the proper place to discuss his personal problems.
Look. I’ve met Mr. Garrett before. He’s a very capable, bright, and enthusiastic young man. He tends to go overboard. Just show him a little patience.” Shaking my head, I said, “Patience? Really Ms. Rogers? Telling me about his sex life borders on sexual harassment!”
Ms. Rogers picked up her phone’s handset and poised her fingers over the buttons. She said, “You want to torpedo Mr. Garrett’s career? Say the word, and I’ll call H.R. right now.” I sat there staring at Ms. Rogers’ finger tapping the first digit of H.R.’s number.
If I make a complaint, I’m sure Jimmy would be out the door. I’ve seen men fired for much less. Ms. Rogers pressed the first digit on her phone. I just stared at her and she pressed the second digit.
I waved my hand and said, “Okay, okay. I don’t want to get Jimmy fired. I just don’t want to hear any more about his sperm!”
“I really didn’t mean to talk about my sperm yesterday,” said Jimmy as he sat across from me in my cubicle’s guest chair. “I apologize.” With a scowl, I pointed at my phone and said, “I have H.R. on speed dial. Just say sperm one more time.” My fingers hovered over the phone’s buttons.
“Okay! I’m terribly sorry. I really meant no offense. Let’s just finish working out the details for this project and I’ll leave you alone.” Jimmy looked at me earnestly, his clasped hands resting on my desk.
“Well okay then,” I said while launching Visual Studio on my PC.
“I did a quick prototype this morning. Let me know what you think.” Jimmy leaned across my desk and pointed. He said, “That is very close to what I’m looking for.”
“Ms. Rogers!” I said as I stepped quickly towards her. She was about to press the button to call the elevator.
Smiling as she turned to face me, Ms. Rogers said, “Oh, hi Heather. Congratulations on another successful project. I’m glad you and Mr. Garrett finally worked out your differences.” I nodded and said, “Thank you. He’s really a pretty nice guy.
He’s very funny, actually. Anyway, I wanted to talk to you about my future here.
I know you’re heading off to a meeting, but I just wanted to start the conversation.” Looking confused, Ms. Rogers said, “Conversation?” “About going back to being Harry,” I said. “As fun as it’s been being Heather, I think I should go back to being the real me, and we need to talk about how to back out of my transition story.”
Frowning, Ms. Rogers sighed and said, “This is definitely not the place to discuss this. I’m free on Thursday morning.
Send me a meeting request for nine-thirty. Nothing I can say to convince Heather to stay?” I shook my head and said, “I don’t think so. Sorry.
I mean, I do enjoy being Heather, but I think that’s one reason why I need to return to the real me. It’s not like I’ve spent my life wanting to be a girl. I just need to stop this before I do something I’ll regret.”
Ms. Rogers gave me a weak smile and said, “You have to do what you feel is right, but I’ll be honest. I really feel this is the real you.”
Before I could answer, the elevator dinged and the door slid open. Jimmy stepped out of the car with a big grin. “I was hoping to catch both of you!” beamed Jimmy. “Mr. Keys loved your dashboard, Heather. He was very excited to see it.”
I smiled at Jimmy and said, “I’m very happy to hear that, Jimmy. I’m glad he likes it.” Ms. Rogers said, “That’s great news, Mr. Garrett. We like making Mr. Keys happy.”
Jimmy grinned and said, “That’s very true. Thanks again, Ms. Rogers for giving the project to Heather. I really doubt that anyone else could have done a better job and so quickly.”
With a grin, Ms. Rogers said, “I hate to break up this mutual admiration society, but I really need to get to a meeting. We’ll talk later, Heather.” She turned and pressed the button. The elevator door opened again and she stepped in and the door closed after her.
“I mean that,” said Jimmy with a smile. “I really do think you were the best one for the job.”
“Thanks, Jimmy,” I said shyly. “It really wasn’t all that hard.”
“Look. You helped me out a great deal, and I know we got off on the wrong foot at the beginning. Let me make it up to you.” Jimmy started to look around nervously.
“You don’t have to do anything, Jimmy,” I said. “I was happy to help out.” “No, really,” Jimmy said. “I’d love to take you out to dinner.” “You’re asking me out on a date?” I said incredulously.
“I don’t know Jimmy. I mean, after what happened at that BBQ place and you know who I am. I’m not staying Heather any longer.”
Looking earnestly, Jimmy said, “Yes, I know who you are. I hate to hear that you’re not going to stay a woman. But, please. Let me take this incredibly beautiful, incredibly smart, and incredibly special woman out to dinner before she disappears. I promise not to talk about sperm.”
I laughed and said, “How can I turn down an offer like that?”
I saw the woman reflected in the mirror shake her head. I changed my pose a few times before leaning into the mirror to check my make-up again.
Here I am, once again getting ready for a date with a man. What am I thinking? Yes, he’s cute, but still. Tomorrow morning I’ll be discussing with Ms. Rogers about reverting back to being Harry.
But tonight, I’m wearing a short, shimmery cocktail dress and heels, and waiting for a man to come pick me up.
I must be insane. I jumped slightly when the doorbell rang. I thought that must be Jimmy at the door. One last check of my make-up and to make sure I didn’t have lipstick on my teeth, I grabbed my matching clutch and hurried to the door as fast as my tight skirt would allow me.
There was another knock on the door just as I was about to open it. I stopped, took a deep breath, and pulled down on my skirt. I opened the door. “Hi, Heather,” said Jimmy.
He was dressed really nicely in a jacket and tie and his hair was combed. “You look amazing, Heather! Here. These are for you.” He handed me a bouquet of flowers. “Thank you! These are just gorgeous!” I said as I took the flowers and briefly inhaled their aroma.
“Let me put these in the water right quick and then we’ll go.” I stepped into the small kitchen of my apartment, retrieved a tall glass from the cupboard, filled it with water, and placed the flowers in it. I hurried back to the door where Jimmy was patiently waiting.
I had debated for half a second whether to invite him in. It was just a few seconds. It’s not like it mattered. I wasn’t going out with him again.
“I’m ready,” I said as I walked out the door. “You are very handsome tonight, Jimmy. You should dress like this at work.” Jimmy laughed and said, “I just do this for special occasions.”
He paused a moment and pointed a thumb at the apartment across from mine.
“Does your neighbor always stare at your visitors?” I glanced over in time to see the blinds quickly close. I yelled through the door of the apartment, “I’ve turned in a complaint about you once already, Jerry. They’ll kick you out if I make another one. Understand?” From behind the door, I heard a muffled, “Yeah. Sorry.” And then silence. To Jimmy, I said, “Let’s go.
That guy creeps me out.” Jimmy took my hand and led me down the stairs. The drive was mostly silent. Jimmy seemed a bit nervous. It wasn’t long before Jimmy was pulling his car into the parking lot of Lucia an Italian restaurant. I was impressed, “How did you manage to get reservations here? I’ve heard it takes months to get in.” Before answering, Jimmy exited the car, ran to my door to open I,t and help me out.
He gave me a wry smile and said, “Trust me. You don’t want to know.”
He took my hand and helped me out of his car. He held onto my hand and led me to the restaurant entrance.
After we were seated, I glanced around the restaurant, “Wow. This is nice. This is very romantic!” Jimmy smiled and said, “I was hoping you’d like it. Too bad we can’t come here every date, huh.” I gave him a wry smile and said with a sigh, “Well, I’m afraid Heather won’t be around for any more dates after tonight.”
Jimmy frowned slightly and said, “That is truly sad news. You’re a very special woman, Heather. I will mourn her loss, but I’m happy that I got to spoil her at least once before she disappears.” Smiling I said, “Thank you for that. Harry will still be around though.”
Wrinkling up his nose, Jimmy said, “Who wants to date Harry?” He looked thoughtful for a moment and then said, “Although, I guess it makes sense for you. Have you always been interested in guys?”
“No,” I said a bit too quickly, “only since becoming a woman.” Jimmy smiled and said, “Well, my guess is that Harry is going to have a bit different life then.”
“What do you mean?” I asked after taking a sip of my drink, leaving a trace of my lipstick on the glass.
“Well, regardless of what gender you’re perceived to be, everyone at the office now knows you like men,” said Jimmy.
“That’s not likely to change when Harry returns.” “I wasn’t interested in men as Harry. I plan to go back to just dating women,” I said in a quiet voice. Jimmy laughed, “From what I understand, Harry didn’t have any success with the women at work.”
Feeling indignant, I said, “I dated at college. And I had one night with Jennifer.” Raising an eyebrow, Jimmy said, “She never mentioned that. Though I guess that’s not something she’d share, but still, she throws men at you.”
Staring at the table setting, I said, “Jenn thinks I’m a woman and just won’t accept the fact I’m not.” Jimmy said, “I tend to agree with her. I mean, how well have you thought this return out? How much do you have invested in being Heather? What do you gain being Harry?
What do you lose?” I laughed and said, “This is the weirdest date I’ve ever been on.
This seems more like an intervention than a dinner date.” “I’m fascinated by you, to be honest. You’ve totally switched sides, from a nerdy boy to a beautiful, desirable woman.
You’re on your way to being a woman. Jennifer told me you’re on hormones. She showed me your old badge picture and I see where you’re looking more feminine than when you were that somewhat effeminate guy.” Jimmy took a sip of his drink and looked up.
“Oh, here’s our food.” There was a pause in the conversation as the waiter set down our dishes. Jimmy was starting to annoy me. This isn’t what I hoped to talk about over dinner, but what did I hope to talk about? When the waiter left, I said, “You’re right.
I love being Heather, but I like being a woman for all the wrong reasons. I love the attention I get from both men and women.
No one ever noticed me before. Now all the women in the office treat me as an equal, and I realize how much I’m being feminized. That’s why I need to stop this now before it gets too far.”
Jimmy shrugged and said, “What’s too far? You’re not obligated to have the surgery. You can just stay like this.
But you still haven’t told me what you’ll be giving up and what you gain by being Harry. Personally, I don’t think you’ve thought this out enough.” I felt angry now.
I said, “What’s to think about going back to who I really am?
Yes, I have a huge investment in women’s clothes shoes, and cosmetics. I don’t have any male clothes at all. I’d have to buy all new.
What would I give up? Being talked over in meetings or just ignored. You have no idea what that’s like to be explaining a point only to have a man start talking as if you’re not even there, making the same point you were!
And he gets the credit! And… and I won’t miss having to get up an hour early just so I have time to put on make-up.”
Jimmy laughed again, “That’s it? Some bad office politics and getting an extra hour of sleep is the best reasons to bring back Harry?
How happy was Harry compared to your happiness now? You were just a cog before and now you’re one of the movers.”
“What do you care?” I asked a bit too loudly as some of the other diners turned to look. I lowered my voice and repeated, “What do you care? It’s my life. My choice.
I don’t want to spend the rest of my life as a woman!” Raising his hands in a defensive gesture, Jimmy said, “I admit. I care for very selfish reasons.
I’ve never been so excited about any woman before.
You’re just not beautiful and intelligent and funny, but you also bring a perspective that… what’s the term? Ciswomen? You bring a perspective they just can’t possess.
“I’ve asked around. Everyone tells me that Harry was sullen and didn’t say much. He just didn’t seem to have much depth to him, but everyone loves you as Heather. You brighten the room, and you smile at everyone.
You’re more emotionally deep… you cry, you laugh. You’re more – well, natural.” I felt a sudden chill, “People talk about me?”
“Not all the time, but I’d say you’re generally liked,” said Jimmy. “That’s nice and all,” I said, “but I can’t live to satisfy others. I have to be my true self.” Jimmy looked me coldly into my eyes, “And what is your true self, Heather? Forget the surface stuff like which clothes you wear, or make-up or even who you choose to date.
You need to look deep into your soul.” Frowning, I said, “Thank you, Doctor Garrett.” His mouth still full, Jimmy said, “You know, this is the best lasagna I’ve ever had.”
Outside of a couple of humorous stories, not much was said the rest of the evening. I was upset with Jimmy for trying to influence my decision to return to be Harry.
He amplified all the doubts I was having, either way. He only wants me as Heather so he can date me. That’s not a good enough reason to alter my life. Yes, he’s attractive and charming, but he’s also annoying as hell. Jimmy drove his car into an empty parking space near the stairs to my apartment. The conversation was pretty sparse during the drive back.
“I know I talk too much,” said Jimmy as he turned the off the ignition on his car. “But I did enjoy your company tonight, Heather.”
“Except for shaming me and depressing me and shaking my confidence in who I am, I enjoyed your company too,”
I said frowning. I opened the door and slid one leg out.
“Let me walk you to your door,” said Jimmy. “That’s okay. I think I can make it,” I said. Jimmy opened his door and started to get out.
He said, “I insist.” Jimmy came around to the passenger side of the car and offered his hand in assistance in getting out. I took his hand and he helped me out. He then started to lead me to my apartment. I hate to admit it, but I do like having my hand held.
The way a man holds it. When we got to the top of the stairs, I said, “Thanks for an… um… interesting evening.” I started to turn to unlock my door. I felt Jimmy touch my shoulder.
Looking down at me, he stepped a bit closer and as he gently slid his fingers down my cheek, he said, “I always enjoy an interesting evening. I enjoyed being with you, Heather.” I ignored the tingle I felt at his touch. I felt my cheeks flush a bit as I looked down and said, “Thank you.
I like you, Jimmy.
You’re a bit intense though.” I looked back up and my eyes locked on his. Don’t look into his eyes shouted a tiny voice in the back of my head. He held the side of my face in his palm and he bent down and gently caressed my lips with his. I felt myself starting to melt. The tiny voice shouted to pull away.
I closed my eyes and pressed into him. Why do I let men kiss me? Still holding my clutch, I slid my arms around his neck as his lips pressed more into mine. No tongue, no roughness. Just a solid, gentle, romantic kiss.
A warmth rolled over me.
He pulled back and smiled at me, “Now that’s the kiss of a woman…” He bent back towards me and touched his lips against mine.
My lips lingered, pressing softly into his. Jimmy disengaged his lips from mine and looked deeply into my eyes as he again gently stroked my cheek with his fingers. He said, “I’d love to see you again, Heather.
Good night.” He looked at me briefly and then turned and hurried down the stairs. I just stood there, watching him go while wrapped in the warm glow of his kiss. I smiled and whispered, “Damn you! Damn you…”
“Hey! Wait up!” I turned around to see who had spoken. I was almost to the elevators. “Hi Jimmy,” I said. “Hey beautiful! Mind if I ride up with you?” asked Jimmy.
He reached out his hand like he wanted to shake. I held out my hand in that limp style most guys hate to feel. He took my hand and before I could react, quickly bent over and kissed me on the cheek. “That’s a bit forward, don’t you think?”
I asked withdrawing my hand. Jimmy grinned and said, “You seemed to enjoy my kiss last night. Thought it’d be okay.” I made a face at him, “That was in front of my apartment. This is at the office.” Jimmy laughed, “This is the lobby. It’s like no-man’s land.”
“Mr. Keys might disagree with you!”
I said as I pushed the button for my floor. As the elevator door closed with only Jimmy and me inside, Jimmy said, “You know, for someone who is planning to become a guy again, you sure outdid yourself as a woman today. You look both a professional woman and extremely hot. I don’t know how you do it.”
“Thank you,” I said, “and I’ve always been a guy.” Jimmy looked me up and down and gave a low whistle, “Well, not many guys could dress like that and be so incredibly hot. Or women for that matter.”
The elevator door opened on Jimmy’s floor. He stuck his foot in the doorway to hold the door open. His face changed to a bit more serious look.
He said, “Hey. I had a great time last night.
You’re a very special girl, Heather. Take that to heart. I’d love to see you again. Which brings me to this. A friend had two passes to Six Flags and now can’t use them. I don’t want to go by myself or even with one of my office buds. I’d love to take you.”
“I’ve never been there,” I said honestly. “Really? You should go. I’m sure you’d enjoy it,” said Jimmy as he started to step through the open doorway.
“What do you say? This Saturday? It’s not like you’re going to just turn back into a guy in the next couple of days.” “Let me think about it, okay?”
I said starting to get annoyed at holding up the elevator. “You have to think about having fun?” asked Jimmy with a confused look on his face. “The passes are free.
I’ll pay for anything else.
Come on. What do you say?” I smiled and against my better judgment, I said, “Okay. I’ll go, but don’t think this changes anything.” Jimmy’s face lit up, “Great! I’ll talk to you later.
Maybe we can do dinner or something on Friday?” The elevator door closed, cutting off any response from me. I like Jimmy, but he sure is moving fast, but considering I’m planning on returning to being Harry soon, I guess he has to.
Should I accept his dinner invitation? I don’t have any other plans, but we’re not dating. We’re just friends hanging out. Yeah. That’s all.
Comments
Jerry
Yeah, sadly my name is Jerry. He has to go too
Jerry
Heather is amazing. Maybe Jerry(the creep at the apartment building) is a spy and the NSA will engage her to take down Jerry, who has been hacking software. Heather knows software. She’ll get the proof to get rid of that creep and then she will have the apartment building to herself for dating. A win win😉. Heather can date who ever she wants then without tip toeing around.
Annah Rourke
Jimmy is sinking fast; but the real quandary is not his being oo pushy, its the mental & heart war being waged between Harry and Heather. I might be giving my own life experiences too much credit but i fought that battle for more then 60 years, in silence for the most part, my ex made every attempt she could to destroy the man she had married despite never learning about my internal conflict until after we were separating. I will spare you more history but suffice to say the battle being waged is in one persons head. I do think these dating encounters give the Heather camp an occasional nudge ahead but Harry has had years spent convincing his side that he was happy as is. Urban has played various cards in her numerous stories that I'm really unsure which side will lose more or if this one will be a win for everyone. Im also thinking the next door neighbor has yet to play their final scenes and what the impact will be - i have my suspicions and my hopes We are forced to wait with baited breath here but luckily I'm enjoying the tantalizing torture
My Freeze
I agree with you. Always like your thoughts.
My Freeze
Yeah, that's all. Heather is here to stay, I hope. Any person as intelligent as Heather could make no other decision but to stay. What a serial this could make. The ADVENTURES OF HEATHER, I like it. Thank you for the great entertainment.
Brianna Demonet
Jimmy sounds like a great guy. While Heather is considering returning to Harry, I don't think she realizes all the advantages Heather brings to the table. Heather seems happier and more social than shut-in Harry.
