Nobody's Perfect

Osgood's driver saw me and pulled up to the curb. The hotel doorman opened the back door of the limousine and ogled my legs while I stepped in and smoothed my dress around my legs. I was having so much fun! It never occurred to me that I wouldn't be able to stop...

I looked out the window at the fancy storefronts as we motored down Worth Avenue. This was the life for me! As a wealthy woman, things were so much more pleasant than my former existence, living hand to mouth between gigs with badass bands in badass towns.

Eventually we came to a stop in front of an exclusive French restaurant. A bit stuffy for Osgood, I said to myself as I emerged from the limousine and entered the dark, elegant lobby. A hostess approached and I told her I was looking for Mr. Fielding. "Of course, Miss, right this way," she said, and I followed her past several half-occupied tables until I spotted Osgood, rising to greet me. Who was that person sitting across from him? In the dim light, I could make out the dreadful scowl of a battle-ax who was regarding me like a fly who just landed in her soupe à l'oignon. In shock, I came face to face with Mrs. Osgood Fielding, Jr.!

I was speechless as Osgood pulled back a chair and nervously introduced me to his formidable mother. "Mama, I'd like to introduce you to Daphne. Daphne, meet Mama."

"She's taller than the others," Mama observed. "Does she speak?"

Up until that moment, I'd assumed that my one and only meeting with Mrs. Osgood would result in an immediate annulment or divorce, with a big check to speed me on my way out of his life. This spoiled everything! As soon as I opened my mouth, Mama would surely detect that I was an outrageous imposter, and she'd probably have me arrested for impersonating a woman. Frozen in shock, I sat down and looked hopelessly at Osgood, who had a downcast expression on his stricken face.

"Mama, Daphne and I are getting married," he stammered.

Mrs. Fielding rolled her eyes. "Another gold-digger," she sighed, as if I weren't even in the room. "When are you ever going to learn?" Then she swiveled her guns onto me. "This marriage is out of the question. Pack your bags and go home to whatever dreary part of the country you came from."

It was becoming apparent to me that all of Osgood's previous wives had melted under Mama's intimidating glare, happily taking their checks to escape from the Fielding madhouse. Figuring I had nothing to lose, I decided to go for broke. Let's see how she handles the unexpected:

"Let's talk turkey. What will it take for you to leave us alone?"

She dropped her jaw in shock. "What did you say to me?"

"You strike me as a woman I can do business with. I may decide to marry your son, but not if you're going to make my life miserable, like all his other wives. What would I have to do to get you out of my hair?"

Smoke was coming out of her ears. "You little tramp! No one has ever spoken to me like that!" Osgood looked like he wanted to crawl under the table.

"Don't get me wrong," I continued conversationally, "the last thing I want to do is get between you and your son. And God knows, marrying into this family won't be easy. If I were smart, I'd take your advice and walk out of here immediately. But let's face it, you're not going to be around forever, and we both have to start thinking about Osgood's future."

Mrs. Fielding looked like she was about to have a seizure. "The nerve of you," she seethed.

"Well, that's one thing we can both agree on. It's gonna take a ballsy chick to make Osgood happy. You're obviously a past master at that, but who's going to keep him in line once you're dead and gone, which could be any moment from the looks of you?"

Mrs. Fielding finally snapped. "Get out!" she roared, pounding the table with both fists so that the silverware jumped.

I pushed back my chair and turned to face Osgood. "Coming, darling? It's now or never," I said sweetly.

I started to walk out of the restaurant, writing off my future as a wealthy woman, when I heard Mrs. Fielding call after me, "Just a minute, young lady. Come back here." I spun on my heel and looked at her. Osgood was still rooted to his chair, sheer desperation in his eyes, which darted between Mama and me.

I returned to my seat and sat back down. Mrs. Fielding seemed to be appraising me with fresh eyes. When she finally spoke, her tone of voice was completely different. "As I said, no one has ever spoken to me like that, with the exception of my late husband. God knows, I'm worried sick about who's going to keep Osgood in line when I'm no longer here, just as you surmised." Now she was speaking as if Osgood weren't even in the room. "Perhaps I was overly hasty. There's something about you that I can't quite put my finger on, but you have grit, my dear. You may be Fielding material after all."

***

A shaken Osgood rode in silence with me back to the hotel. "Well, that went well," I finally said to break the ice.

"I've never seen Mama so furious! Just when I thought we were done for, you turned her around...what just happened?"

"We learned that Mama can't hit a curveball."

"None of my wives could ever figure her out."

"That's because none of your wives were men. I know an alpha dog when I see one."

Osgood shook his head. "Daphne, I have a confession to make." He looked forward to make sure the chauffeur couldn't hear us, then continued in a low voice. "Most of my life, I've known that something was...wrong with me. I think that's why I got married so many times, to try to compensate for it."

"Are you trying to tell me that you're a little bit queer?"

He hung his head in shame and started to weep. I took his head into my lap and sighed. "Oh Osgood, you've got nothing to cry about. In the first place, you're hardly alone." He looked up at me in bewilderment. "Just look at me! I'm the one wearing a dress! I never in a million years thought I'd wind up liking myself this way, but that was before I met you..."

"Do you still want to marry me?"

"I'll be honest with you, Osgood. I never thought Mama would go for me, and I was expecting a big payday when she showed me the door, like all your other ex-wives. Now I'm not so sure."

"Not so sure you'll marry me?"

"No silly, I'm not so sure I want to let you get away!"

***

Thanks to Osgood's connections, I was able to obtain a forged birth certificate for Daphne which enabled us to get a marriage license, and Osgood and I were married a few months later. And yes, I wore Mama's (heavily altered) white wedding dress! After I finished putting on my gown and veil, I stood and looked at myself in the mirror for a long time. My dress was so long! How would I even be able to walk in it? Oh well, at least I don't have to worry if my seams are straight, I thought ruefully as I pondered my reflection, the girl that was me. Is this really what I wanted? To be a bride, a wife, a woman? Somewhere deep inside me, Jerry was screaming "Noooooo!" But inexplicably, Daphne was smiling back at me and saying, "I want this! Osgood needs me, and I'll never find another person like him, man or woman. Let's do this!"

The marriage of Miss Daphne Whoever to Mr. Osgood Fielding III was the social event of the year in Palm Beach. The ceremony was lovely, and our wedding night was memorable: I'd held out from giving it up to him during our whirlwind courtship, still unsure of what I was doing and where I was going, but once we tied the knot, I surrendered to my fate as a married woman and let him have his way with me.

For our honeymoon, we took his yacht to the Bahamas, and that first night of married life is chiseled in my brain. First, I yielded to his request for some "suction" and gave him the first blow job of my life. I can't say that I enjoyed it, but he sure did, and somewhere along the way I got totally into pleasing my man, and when he finally came, it made me feel incredibly feminine and satisfied. Osgood reciprocated by going down on me, and there was something about being suckled by my husband while wearing my white satin bridal nightgown that drove me half insane, and that night I had the best orgasm of my life in Osgood's loving mouth.

The next morning, Osgood was ready for more, only this time he plumped a pillow under my butt and proceeded to make a woman out of me. It hurt a bit at first, but Osgood had lubed himself well and after the initial shock of penetration, I quickly yielded to the raw carnal pleasure of being filled and fucked by my husband, until when he finally gasped that he was about to come, I knew that I was going to come too, and our bodies shuddered together as we experienced the first of many, many simultaneous orgasms. "Zowie," we sighed in unison.

After a delightful breakfast served by the discreet crew, I changed into one of the swimsuits that Osgood bought for me that first day at Abercrombie & Fitch, and we lolled on the foredeck for hours, sipping champagne and sharing naughty thoughts about the future that awaited us.

When we finally pulled into Nassau on day three of our honeymoon, totally sated and satisfied, we decided to have dinner at a new restaurant that was the talk of the Island. Apparently a young American couple had taken over a derelict business and turned it into the most fashionable port of call in the Bahamas. Osgood checked us into the British Colonial Hotel, where after a long, lovely bubble bath, I put on a cute flapper dress, heels and stockings - by then, I was one hundred percent content with dressing myself as a woman, and I doubted if I could ever go back to being a man - and after some final flourishes with my hair and makeup, I was ready to take Nassau by storm.

Osgood hailed a taxi to the restaurant, which was totally charming with lots of wicker furniture and ceiling fans, and after we were seated near the dance floor, we made small talk over martinis, very much in love. Our dinner was excellent, and after a couple of foxtrots and an early exit from an impromptu Charleston contest (dancing in high heels was still a challenge for me) we were about to head back to the hotel when the owners of the restaurant approached our table. I couldn't believe my eyes!

Joe and Sugar recognized Osgood at once, but it took them several double-takes to realize that the woman seated next to him was their old friend, Jerry. Actually, Sugar had known me only as Daphne, but of course by then Joe and filled her in on my - and his - reluctant transformations into women to stay one step ahead of the vengeful mob.

"You look incredible," Joe said. "I can't say I'm surprised, but I kind of am."

"Well, I'm not," Sugar piped in. "I always thought Daphne was a special kind of girl - of course I didn't know she was really a boy - but seeing her here with Osgood seems, I don't know, kind of right."

"I should hope so," Osgood said proudly, "since you're talking about my wife."

"You really went and got married?" Joe gasped.

"Yep. What about you two?"

"Oh, we're still talking about it, Sugar sighed. "At least I'm talking about it. He's just listening."

Joe changed the subject. "Any sign of our old friends?"

"If you mean the Chicago mob, not a peep. I'm not sure they'd recognize me anyway..."

"That's an understatement! We haven't seen 'em either. That's one of the reasons we landed here, to stay far, far away from them." Joe proceeded to describe how they fenced my diamond bracelet for pennies on the dollar, slipped away to Nassau and bought a failed restaurant for a song. The rest was a combination of hard work and good luck.

"Well, it looks like you ended up with something special," I said. "I envy you," I added with genuine remorse over all that I'd given up - my identity, my manhood and my future as Jerry. But all that was in the past: I was a married woman now, a wealthy married woman, and I knew my old shallow self well enough to know that there was no way I'd ever give up my new life to return to being a hapless loser like Jerry.

"We know how lucky we are," Sugar replied. "I love Joe to death, and I'm never letting him go," she hugged him close.

"That's exactly how I feel about Daphne," Osgood beamed.

Joe and I looked at each other and shook our heads. We'd come a long way from that warehouse in Chicago, and we'd both landed on our feet - even if one of us had to wear high heels! I envied Joe his life with the gorgeous Sugar, and I think he envied my newfound wealth and security as Osgood's "wife." A happy ending, even if we both knew that our stories were far from over.