Bet Gone Wrong

"I wish I could say I'm sorry."

"But you're not, and neither are the rest of us. Congratulations."

I went back to work, and had no problems from anyone else for the rest of the day. I did have to pee later, and true to her word, Rachel escorted me to the women's room and stayed in there until I finished and left. As I exited the restroom, I saw my boss nearby. He looked totally pissed and glared at me before turning and stomping away.

As my standard quitting time rolled around, I gathered up my stuff to leave. I saw my boss, who seemed as pissed as ever.

"Not working late tonight?"

"Not tonight. I have someplace I need to be. Besides I'm on track to have my part of the close finished on time, even without overtime."

He snorted and went back to his office. Mind you, I still wasn't thrilled about going to an interview as I was, but Amir, my recruiter assured me it wasn't a problem. I drove to the company, parked and went in. There was a receptionist there, so I went up to her.

"I'm Jamie Morgan. I'm here to see Mr. Howard."

"I know he's expecting you. Let me call him. It should only be a minute."

I sat down, making sure to be discrete and tuck my skirt to be modest. Very shortly, a middle aged man came into the lobby, saw me and smiled.

"You must be Jamie. Pleased to meet you, come in. Can we get you something to drink?

"I'm fine."

He escorted me to a room where a man and woman waited. They stood, shook my hand, then we all sat down. They alternated between them, asking questions about my work history and qualifications. I told them what I'd done and about my computer skills. They had some mildly technical questions about spreadsheets, no doubt to try to judge just how good I was.

They didn't comment on my attire, and after we had been at it for almost an hour, I decided to address the issue.

"I don't normally dress this way at work."

"That's a minor issue. You see at one time we had developed a bad reputation which we're trying to correct. We want to be very LGBTQ friendly, and having an employee who is trans or even cross dressing is actually a plus to us."

"You mean you want me dressed like this?"

"As a matter of fact, yes. Look, there's lots of people with similar qualifications. If you continue as you are, we want to not only hire you, but pay you fifteen thousand over your current pay. And the current manager in that area is retiring within the year. Assuming your work is as good as we think it is, we can almost guarantee you that spot, and another fifteen grand as a promotion raise."

"That almost sounds like you're bribing me to continue to cross dress."

"That's a very negative way to put it, and we'll deny ever saying anything like that."

Shit, here I was trying to get through a week of cross dressing, and now I had a job offer at more money with the possibility of a promotion and even more money, contingent on continuing to dress like a woman. I know, paying me fifteen or even thirty thousand would likely save them hundreds of thousands that lawsuits would cost them.

If I turned it down, what could I expect from my current employer? My boss hated me, and apparently now so did many of the other men in the office. Even once I went back to normal attire, I know I'd be on a lot of shit lists there. So my choice was more money but cross dressing, or less money and probably out on the street when they could find a good excuse to fire me.

The old phrase was 'damned if you do, damned if you don't'. That's about the way I felt right then, but I decided to accept their offer. Did I want to continue to cross dress? Not particularly, but my other option wasn't any better, and might well be worse. At least with this job, I had the chance to see if I could find yet another job where I could dress normally.

I accepted the job offer, and told them I'd give notice to my current employer. They said they would like me to start as soon as I was able. As I exited the building, I called my boss, since I suspected he might still be there. I told him that I'd put it in writing tomorrow, but I was giving him notice.

He seemed nastier than usual. "Fuck two weeks notice. I'm at the office now. Come by and pick up your personal shit. I don't ever want to see your faggot ass again after today."

"What about close?"

"That's my problem. I want your ass gone."

I quickly went back inside where I'd just interviewed and told them my boss didn't want two weeks notice and that I could start tomorrow if they wanted. They seemed ecstatic, and said they'd see me tomorrow morning. I got in my car and drove to where I had been working. There were few people still there, but my old boss walked me to my cube and watched carefully as I took my stuff.

My boss sneered at me. "I wanted to fire you as soon as I saw you yesterday, but they told me I had to follow proper procedures. You saved me some grief. Now get the fuck out of here."

I had one box, not very large, that I took to my car and drove home. I might not be completely pleased with the circumstances of my new position, but at least it shouldn't be as toxic. By the time I got home, Susan was there. I'd told her yesterday that a recruiter was interested in me, then texted that I had an interview. She hugged and kissed me, then wanted to know how it went.

"So how did they feel about having you show up for an interview like this?"

"I'd say that were okay with it, but that's not quite true."

"They were uneasy about having a guy in drag?"

"If they had been, it would have been simple to tell them it was just temporary."

"You mean they were good with it?"

"They offered me a job, at more money, with the chance for promotion, but only if I show up for work in drag."

"You never thought this would be permanent, did you/"

Susan began to laugh, and laughed so hard, she cried. She sat on the sofa, while I stood there, still in shock over it all. Finally, I sat down next to her. She hugged and kissed me again, getting ever more passionate as she did. She lay back on the couch, pulling me onto her as we kissed. Being intimate with her was one of the few bright spots in my day.

"So I assume you accepted, or didn't you?"

"My old boss is now so bad, I needed out of that. I start at the new place tomorrow."

"We're going to need to update your wardrobe. Skirts and dresses, I'm guessing."

"They probably figure pants suits are not femme enough."

"So, Jamie, I get a bonus. I get a cute girlfriend and still have a lover with a cock."

"Fuck. I may have to work that way, but don't want that 24/7."

"Don't you think that if they want a trans employee, they want you to be trans even when you're not at work?"

"I should at least be able to dress normally here."

"Okay, you can wear women's jeans and bootie shorts here, instead of always being in skirts."

"You're really cutting me a lot of slack there."

Susan kissed me again, and I reveled in her kisses. I reached up and began to stroke her boobs and she moaned as we kissed. She reached down and stroked my ass, then eased my skirt up and rubbed my ass over my panties. As much fun as it was being with her, that reminded me of how I'd been dressed since I lost my bet. Then she snuck her hand inside my panties.

I got my hand inside her top and pulled up her bra to caress her titties directly, with no cloth in the way. I love Susan's mammaries and enjoy fondling them. She seemed to enjoy it as well and I almost forgot how I was dressed and the indignities of the day. Then Susan took the hand that was in my panties and snuck a finger in my ass. That made me squirm and I think I had a little shriek.

Sure Susan is a woman, so it's not like having a guy mess with me like that. Still, I can't say I'm at all fond of having anyone mess with my ass. She began to finger fuck my ass and to my own astonishment, I found my cock had gotten very hard. Emotionally, I might not like it, but some part of my body didn't get that message.

To my disgust and amazement, I found myself getting really turned on. Before that got too far, I got off her and pulled her to her feet. I led her into the bedroom, undoing her blouse as we went. In turn, she unzipped my skirt, which pooled at my feet and I stepped out of it. I got her skirt off and kicked off my shoes along the way.

We reached the bed with both of us in bras and panties. This time I lay down, pulling her on top of me. That made it harder for her to finger my ass, but still kept us quite intimate. Let's be honest, I wanted to make love to Susan, I just didn't want her messing with my ass too much. As we kissed, I played with her very real breasts as she fondled my fake ones.

I reached behind her to unhook her bra, and take it off her. She had me in a front snap bra that she quickly undid. We toyed with each other, until she broke our kiss and slid up my body, presenting her right titty to my awaiting mouth. I wrapped my lips around the nipple and began to suckle at her bosom. I love women's mammaries, and particularly liked Susan's.

I grabbed her waist, because I figured she'd move up further and I wanted to enjoy this part of her thoroughly before moving on. I worked that tit over until she began to moan, then shifted her to one side to give my attention to its mate. I continued to pleasure her until she reached an orgasm and pretty much collapsed on me, almost smothering me with her boobs.

I suppose being smothered by a breast is not a bad way to go, but I wasn't really quite ready to pass on. She regained her senses and lifted up enough for me to breathe again, then she slid farther up my body, She rested on her knees with her quim right in my face. Far be it from me to turn that down, so I began to lick her labia and even insinuate my tongue between them.

She began to move her hips, almost like she was fucking my tongue. I was happy with that, since I enjoy going down on her. In the middle of this, all the pains of my day were swept away in a cloud of sexual bliss. She came to another orgasm, and I was holding her, otherwise she might have fallen backwards. By the time she recovered, I was ready for my own pleasure.

Susan was happy to accommodate me, and pulled off my panties and sunk my cock deep into her pussy. It felt like bliss, and she simply held it for a bit with me balls deep in her before she started to move. It was a slow movement but getting nearly out, before plunging me all the way in her again. It was simply a slow sensual fuck and I let myself get caught up in it all, before pulling her hips tight to cum in her.

She kissed me before getting out of bed. "That was nice, but I'm hungry. How about dinner?"

She had gotten some Italian food delivered, but obviously by that point it had gotten cold. We heated it in the microwave and sat at the table each in only panties to eat. There was chicken marsala with farfalle and mushrooms. We also had fettucine Alfredo with chicken, broccoli and mushrooms. We shared both dishes and were hungry enough that there were no leftovers.

We sat and talked while letting our food settle. I brought her fully up to date as to what had happened, both at my former job, and at the place where I was going to be working. Susan decided it was too late to do any clothes shopping that night. Besides we were both too horny and went back to making love as soon as our stomachs allowed. We fucked until we fell asleep from exhaustion.

.....................................................................................

The next morning, I dressed and went to my new job. Susan helped me with my makeup since I was still not good at that. Of course I had paperwork to fill out with Human Resources, plus a short orientation before being shown to my new work area. I was introduced to the other people who worked in that area and most were quite friendly. My new boss seemed cool and distant though.

Where I had a cube at my old employer, I actually had a small office at this place. That was kind of a surprise albeit a pleasant one. I had a computer and got logins and such and quickly got down to work. There were five men and three women in the department, besides the boss and me. As lunch time came, one woman asked if I'd like to join her for lunch.

Teresa was early 40s and married, though not held together badly. There was a café near the office and we walked there to eat. She seemed curious about me.

"So, are you seeing anyone? I'm married, but I know a few others are curious."

"I'm living with my fiancée, Susan."

"Is she like you, or was she born as a woman?"

"Susan was born as a woman."

"I thought most trans went for the opposite sex of how they identify."

"It may not be quite what it seems."

"Well, Jamie, our boss, Frank Donaldson, isn't trilled about you being here."

"I thought it was odd that he didn't interview me."

"Frank ran off a former gay employee, who threatened to sue over it."

"So they hired me to keep from having more problems."

"I think Riley got a settlement along with a promise to hire more LGBT."

"So top brass made that promise, but Frank didn't agree."

"He was less than a year from retirement. They told him if he didn't cause problems they'd let him stay until he retired."

"So he may not like me, but he won't cause problems."

"He's just marking time till then."

"That's nice to know."

"So, Jamie, did you always know you were a woman?"

"I may dress as a woman, but don't identify that way."

"You just like cross dressing?"

"Weird circumstances made me dress like this, and this job now requires me to."

"So if you had your druthers?"

"I'd dress like a male. But there are a lot worse things than being in drag."

"Don't get pulled over by the cops unless your license says you're a woman."

"Fuck, no."

"Well, Jamie, you seem to be pretty sharp, so I'm glad you're on board."

"Thanks."

We ate our lunch and went back to the office. Teresa said she'd spread the word that I was taken, so I wouldn't have anyone hitting up on me. Eventually, even Frank had to admit I knew my stuff, even if he didn't like having someone like me around. I did get hit up on a very few times, and I gently dissuaded them. Mercifully, most did not object to having me brought in as the person to get promoted.

Odd as it may sound, after a little while, it almost felt natural to be in skirts and dresses. Come the weekend, Susan and I went shopping for more clothes for me. My former male clothes are now all gone, having been donated to charity. I indeed dress as a female 24/7 and am quite used to it.

I still glue on breast forms, though Susan said she'd love for me to have titties of my own. I made it clear that was a step too far and she's settled for what she has. We're getting married soon, and she has chosen a lovely bridal gown for me, while she plans to wear a tuxedo. My hair has grown out so I no longer need a wig and she had me get my facial hair lasered.

Susan has had her hair cut short and often wears male clothes and has a binder on her chest when we go out. Now we look like a straight couple, but with me as the woman, and her as the man. I no longer see my old friends, most of whom were weirded out by my new attire. We've made a new set of friends, though many of those were people Susan knew before.

After six months, Frank retired and I became department manager. I've been told I have a good chance of being promoted to AVP in another year or so. I came into this job, figuring I'd mark time until I could find a job as a man. Now it seems like Jamie the girl is who I am. I had my driver's license changed to show me as female with a new picture, but I still don't want to get pulled over by the police.

What started as a misbegotten bet set me on a new path in my life. It isn't a path I'd ever have chosen, but it has had its rewards, so I can't regret it either.