tagRomanceYes, Dear Ch. 01

Yes, Dear Ch. 01


This really isn't my story, it belongs to my only crossdresser friend, who I consulted while doing research for another story. It's her dream situation, and I agreed to write is as a thank you. I wouldn't let her see the finished story. She has to read it here. Hope you enjoy, Anne, this one's for you.

I was going to put it in the transsexual and cross dresser section, but it's just too much of a love story to be anything else. If this offends you, stop reading now. There are plenty of good stories to capture your interest.


This is the story of how I fell in love.

I've been called petite, at five three and weighing a hundred and five pounds. I always wear business suits, jacket, skirt, usually a matching silk blouse. I think my legs are too pretty to conceal. My dirty blond hair trimmed into a short, professional style. I always wear four inch heels, so I look taller. My whole appearance screams "successful business woman".

And I am. Very successful, working for a Fortune 100 company. At thirty, I'm a junior vice president, and the sky is the limit for advancement, as far as I'm concerned.

I have an MBA from Wharton, apprenticed with some of the most successful firms in the world, landing my dream job right out of college.

I've been called, brilliant, driven, devious, and a cast iron bitch. All apt descriptions.

How did an attractive young woman work her way up the food chain so quick? Well for starters, I never dated, giving my full attention to work. Oh, I got hit on, some customers have even hinted that my favors would go a long way towards sealing a deal. I usually found an excellent reason why my company should stop doing business with theirs. These men didn't get where they were by being stupid, word got around, and I was always treated with respect from then on.

"Married to her job, that one," they would say behind my back, "wonder if she's a lesbian".

I was so successful because I knew how men thought. I know, you hear men and women say that, but very few actually do. I could work the good old boy system with the best.

Why? Because underneath those Armani power suits, thigh highs, and expensive lingerie, lies a five inch cock. So now you know I'm not a lesbian.

That's right. I was born male. It didn't take me long to realize I was trapped in the wrong body. I actually had reasonable parents, and by the time I was thirteen I was in therapy for gender reassignment. When I got my driver's license I could legally put down female in the proper slot.

Social interaction with other teens was severely limited. I tried a regular high school, and when who I was became known, I was beaten up twice and almost raped once. After that, I tended to hang with others in my support group. I was privately tutored.

College was a little better, but not much. In fact, I had only been with two sexual partners, one transsexual that only gave and received oral, and one guy who was too rough taking my virginity. I bled, hurt, and swore off sex. I masturbated a lot to relieve my sexual tension. I was very lonely.

I literally fell into my husband's arms. It was late April, and as I gazed down from my forty third floor corner office, I had an almost uncontrollable need to get outside and breathe unfiltered air. I decided to take a long lunch, get a sandwich and sit in the park, enjoying the sunshine.

I had to walk by a construction site, another skyscraper that just had to be a floor taller then the last. As usual, the catcalls and whistles followed me all the way down the block. Construction workers are pigs generally, half a strand of DNA above an ape.

I got my sandwich and soda, found a nice bench with a southern view, and enjoyed the sunshine, for about five minutes.

The two men, obviously construction workers, were muddy, unshaven, and Neanderthals had more brain cells.

"Hey bitch, that's our bench."

I got up quietly, prepared to move. The loudest one got closer.

"Who said you could leave? You owe us for the use of this bench."

I gave them my most professional look.

"This is a public park. I should be able to sit where I want. But, if you need the bench that bad, take it and welcome. I have to get back to work now."

"We're not done with you missy" said the biggest one, grabbing my arm and causing me to drop my soda. "I think a kiss or two will square the debt."

I was struggling with his grip when a quiet voice said "Charley, I think you should let the lady go and apologize for being such an asshole."

He let go of me so fast I started to fall when strong arms encircled me and helped me upright.

"Miss, are you all right?"

I couldn't help it, I was so scared I started crying. I managed to sniffle a yes, conscious of the arms still around me. I think he realized he was still holding me at the same time, and gently let go.

"Fuck you Brian, we ain't at work and you ain't my supervisor" the man who tormented me said, trying to save face.

The man named Brian smiled.

"You're exactly right. So if I stomp your ass, you got no beef with the company or the union. Wanna get in on this, Dave?"

Dave appeared nervous.

"I got no problem with you, man. We was just havin' a little fun."

"Does she look like she's having fun?"

He had pulled me behind him, a position I was more than happy with.

"Get back to work, boys. If you hang around I might get the idea you intended to aggravate this young woman more. You know how I would hate that."

Dave couldn't leave fast enough, Charley wanted to save face, but as soon as Brian turned to him, he left.

I was shaking as he seated me on the bench.

"Don't worry, they won't bother you anymore. Relax, enjoy your lunch. I'm sorry they spilled your drink. Here, share mine."

He poured something from his cooler into a plastic cup and handed it to me. I took a small sip. My eyes widened. He smiled.

"Homemade lemonade, with a touch of raspberries. Do you like it? I have more."

I held out my cup, and he refilled it.

"May I join you?" He asked politely.

"Please " I said moving over slightly.

After the lemonade my bought sandwich tasted plastic. I could see him frown.

"Try this." He handed me a croissant filled with chicken salad. I had never tasted chicken salad like that. Made from herb smoked chicken, with bits of grape and pecans. I practically inhaled it. He looked at me, smiling.

I felt like a glutton. I tried to cover it up.

"Your wife is an excellent cook."

He grinned.

"She better be, when I find her. This is my recipe, I'm a fair cook, for a single guy."

"Good looking, single, and able to cook too. I might just apply for that wife position."

Shit! Where did that come from? I colored.

He laughed.

"Thanks, I think."

We talked for thirty minutes before he looked at his watch.

"I've got to go. I'm the foreman, wouldn't look good to be late. I enjoyed lunch. What time do you get off work?"

The question caught me by surprise.

"Five thirty."

He gave me a five hundred watt smile.


He scribbled something on a notepad and gave it to me.

"I'm doing interviews for the wife position. I can work you in at six thirty. Don't be late, you'll lose points if you are. It was a pleasure to meet you, Andi."

I must have looked like an idiot, holding the piece of paper and grinning.

"See you at six thirty, sweetie."

And just like that, he was gone.

I came to my senses and checked the time myself. Shit, thirty minutes late from lunch. I was never late from lunch! I hurried back to my office.

When I went by the construction sight, the Neanderthals glared at me, but not one worker said a word. I looked up, Brian was in some kind of contraption about two stories up. It did not look safe. He gave me a small wave. I know I looked like an idiot waving back so hard. I practically ran into my building.

My personal assistant, Aubrey, was a woman in her fifties. I liked her. She had been with me since I got my first promotion. She was very good at her job, and would have mothered me relentlessly if I let her. After three years together she starting dropping hints. Why didn't I have a picture of my boyfriend on my desk? Was that wedding bells she heard? You work too hard, you should date more.

We had a code. If I stamped my foot and said "MOM!", she would back off for awhile.

I caught Aubrey watching me and smiling several times. I finally had to ask.

"What are you grinning at?"

It all came out in one long rush.

"You're not the only one who had lunch in the park today. We all saw you. Who is he? What does he do? Are you serious? He was, oh, what was it Janine said? Oh yeah, ripped. That means hunky, right?"

"Yes, it means hunky. No, we're not serious. I just met him today. He's a construction foreman on that project down the street. With me so far?"

She nodded.

"Did he ask you out? Did you ask him? He was definitely interested in you, that much was plain."

I couldn't resist.

"Well, he is currently conducting potential wife interviews. He offered me a six thirty slot. What do you think, should I dust off my resume?"

Her mouth hung open.

"You already got a date? Tonight?" she looked at the time.

"What are you standing around for? It's five ten, the clock is ticking. Where is he taking you?"

"Nowhere. I'm supposed to meet him at...." I pulled the paper out of my pocket, "Cafe Rizzo, ever heard of it?"

"Heard of it? It's supposed to be the third best Italian restaurant in the city. It's basically a Mom and Pop place. Small, intimate, next to impossible to get into. He must be more than a construction foreman to have the pull to get in there on short notice. Bring me a doggie bag, okay?"

Her mouth almost hit the floor when I told her I wasn't sure I was going.

"You're kidding! Young lady, you are going and you're going to have a good time. Are we clear?"

I stamped my foot. "MOM!"

"Oh no, little lady, that's not going to work this time. Now get your cute little butt in gear and go capture a man's heart. You're fired for the rest of the day. Go on now, get ready. Make me proud."

I was so shocked I let her lead me to the small closet of clothes I kept at the office. I never knew when something last minute would come up, and had to have suitable clothes.

Aubrey was already going through my wardrobe.

"Too formal, too business like, ah, this will do."

It was the classic little black dress, modest hem and neckline.

"This, and the pearls. Now go do your makeup. I'll call your driver, have him waiting."

If I hadn't wanted to go so much, I would never have let her go on. I even had to stand inspection before I left.

"Very nice, dear. Now, go have a good time. Details expected tomorrow. I'm going home and rape my husband, imagining he's a 'ripped' construction worker. Bye bye."


I was on pins and needles on the way. I dismissed my driver, I didn't know how long I would stay, and would cab it home.

I was about to ask the hostess for Brian, and realized I didn't know his last name.

I finally squeaked out "Has Brian arrived yet?"

She broke out in a big smile and led me to the back of restaurant. He rose to meet me. Damn, he cleaned up nice. White shirt, black vest, jeans and loafers. He looked good enough to eat.

"Here she is, Brian. You can stop worrying now."

She looked at me while he colored.

"He's been up to check the door at least ten times in the last twenty minutes. I can see why. I'm Gina, this idiot is my first cousin."

That explained the restaurant. It also explained why nearly every worker in the place, including the dishwashers, came by to be introduced. Finally a man and woman in their fifties shooed them away.

"Go on now, You can give her the third degree later. Let them have a little peace."

They were his aunt and uncle. If Brian turned out like his uncle when he was fifty, he'd still be getting looks. His aunt was small, petite really, and Italian to the roots.

"Come to lunch next Sunday. We'll talk. Now, I'll make sure you're left in peace. Enjoy your meal."

What meal? We hadn't had a chance to order.

The platters started appearing. It would take a week to eat this much food. Everything tasted so good, she had to have at least a bite of it all. They didn't have much conversation until after the dishes were cleared, and they were on their third glass of wine.

Brian grinned at me.

"Okay, time to fill out your application. Start with the basics. How old are you? Have you been married before? Got someone in your life right now? Foolish question, that. As pretty as you are, there has to be someone. Where do you work? What do you do? Are you happy with it?"

My mouth hung open in shock. Damn, get right to it.

"Don't you know it's not polite to ask a lady her age? I'll be thirty one in three months. I've never been married. Not dating right now, I'm concentrating on my career. I work at Chase and Simpson, and I'm quite happy with my job."

Why did I tell him all that. He just sat there, looking at me with those calm green eyes. I wanted to bare my soul to him.

"You're a little older than I thought. Not enough to matter, though. I notice you said where you worked, but not what you do. Care to elaborate?"

I hesitated, I had to make a lot more money than he did. Some men couldn't handle that, or the fact that I held a position of power. I shook myself. What did it matter? This was never going anywhere.

"I'm the youngest vice president in their history. I run run the mergers and acquisitions branch. Sometimes I get two clients to merge who can complement each other and be more profitable. Sometimes they get bought out by my company. And rarely, it's a hostile takeover. I'm very good."

He nodded, listening intently.

"What kind of pay grade does that carry? Stock options, bonuses, you must be making out quite well."

This should scare him off.

"I make two hundred ten thousand a year, plus bonuses and stock. It averages a little more than three hundred thousand."

He seemed impressed. Time to counterattack.

"What about you. If I'm older, by how much? Does being a construction foreman pay well? Ever been married before? Time to share."

"I'm twenty six. Never been married. It pays all right, I average seventy five thousand a year with completion bonuses. I don't intend to stay where I am. I'll have my degree in architecture in another year and a half, going part time."

He turned the tables again.

"What about kids? Do you want them? How many? How close?"

I figured this would be the deal breaker.

"I can't have kids. I've always liked them, but anyone I end up with, unless they already have kids, would have to agree to adoption."

There it was, the biggie.

He just smiled.

"I've always wanted three. One of each, the last doesn't matter. I'm adopted, myself. Best thing that could ever have happened to me."

Didn't see that coming, but it explained why he didn't look Italian.

We talked until closing time. His aunt escorted us to the door, extracting promises that we would join them next Sunday.

"Where's my cab?" Aunt Rita waved her hands.

"Why waste money on a cab when you have a perfectly fine young man willing to escort you home? Behave yourself Brian. I like this one."

It was a four door truck. He drove straight to her condo. He helped me out and escorted me to the security door.

"Well, I know now."

"Know what?"

"Where to pick you up. Seven O'clock, Saturday. Dress nice, we're going to the opera."

With a quick kiss on the cheek and an even swifter kiss on her lips, he was gone.

I didn't remember how I got into my condo. I did remember the huge smile on the doorman's face.

"I didn't even get a choice" I though as I got ready for bed. I knew I wouldn't have turned him down.

I rubbed my lips as I snuggled down, remembering his kiss.

Cold hard reality hit me the next morning as I showered. I rarely got an erection any more since my hormone treatments, but today I had a serious case of morning wood. I even masturbated, dreaming of Brian.

"He'll hate me when he finds out" I thought later, as tears threatened to ruin my makeup.

My mood brightened as I reached work. I'd hold onto my fantasy just a little longer.

Aubrey was on her as soon as she entered her office.

"Spill! I see that smile on your face. Was the food good? Does he clean up well? Did you get any last night? Did you bring me any leftovers?"

I let her wait for a few seconds.

"All right, here we go, in no particular order. He cleans up very well. This was a first date, so no nooky. His family owns the place, and the food was to die for. There were no leftovers."

I watched the disappointment on her face before I handed her a handwritten note.

"What's this?"

"It's a personal invitation for you and your husband to dine at Cafe Rizzo this Friday. Enjoy. Did you wear your husband out last night? Did you make him wear a hard hat?"

Aubrey held the note in awe, before turning just a bit red.

"I didn't wear him out, more like down. But not enough that he wasn't recharged this morning. I was almost late."

Andi hugged her.

"Now, if we can get our minds out our panties, let's get some work done. And Aubrey, don't spread this around."

Aubrey laughed so hard she almost spilled the two cups of coffee she held.

"Too late, my little Cinderella. Joan from accounting and Barb from legal were at the cafe with their husbands. They saw you and I quote 'hanging onto your hunk like a drowning woman clings to a life preserver'. I've had three calls already this morning."

Even my boss said something that afternoon.

"Popular rumor has it there's a new man in your life. Quite attractive, according to the woman in accounting. I'm not prying, I'm just saying good for you. All work and no play and all that. Just tell me he doesn't work for a competitor."

I was glowing red

"No, he's in construction, lower management, but he'll be qualified as an architect soon."

"Sounds great, think how much you'll save when it comes time to design your dream home."

I started telling him it was just casual until I saw him smiling.

"Relax Andi, I'm just teasing. It's good to see you look human, instead of the ultimate business woman. Does he know?"

Bob was the only one in the company who knew my secret. When he offered me the vice president slot, I felt it necessary to come clean. I didn't want it to be discovered and brought to light to embarrass the company. It surprised him, but my efforts spoke on their own. He supported me and I got the job. If Aubrey was my mother figure in the office, Bob was her counterpart. I often told him I wanted to be just like him when I grow up. It pleases him no end.

"No, but I intend to tell him soon."

He nodded.

"I expect no less from you. And Andi, if it doesn't go well for you, I have a dry shoulder you can cry on."

I couldn't help myself, and kissed his cheek.

"I swear, between you and Aubrey, It's like I never left home. Thanks, Dad."

I believe we were both misty eyed for awhile.

I now had a dilemma. It was Tuesday, and I hadn't chosen a gown. My cheerleaders, Aubrey, Barb, and Joan, spent two lunch hours helping me shop. I was about to give up when we saw it.

Almost full length, open back, modest neckline. Red satin. I had a 34C chest, mostly hormone induced, but augmented by small implants. It was hard to go without a bra because of my extremely sensitive breasts. I could almost orgasm just from rubbing them. I wondered how his lips wold feel on them. I would probably explode on the spot.

Matching shoes, handbag, a small red velvet choker. My Adam's Apple was almost nonexistent thanks to hormone treatments at an early age and a bit of discreet surgery. I spent two hours having my hair done

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