St. Clair Ladies Circle: Leonard

Sternberg looked at his bookings, then smiled at Leonard. "Ah, yes, Mr. Hopkins, party of three. Your usual booth. Yes, yes, everything the same?"

"Everything the same, Luigi."

Sternberg turned to his wife, Bernice. "Mama Rosa, you remember Mrs. and Ms. Imhof? There the guests of Mr. Hopkins tonight."

Bernice Sternberg, whose waistline equaled her height, was manning the cash register. She looked at us, then at Leonard, then frowned at her husband. "We're glad to have you," she said perfunctorily.

Sternberg raised his hand and a waiter appeared out of nowhere, black pants and shoes, white shirt, no tie, towel over one arm.Bella Napolihas a main dining area, and a mezzanine. We were ushered to the upper level. There were fewer tables there, spaced further apart, giving each party more privacy. Leonard held out the chair for me, while the waiter did the same for Naomi.

"The San Antonio 2001, Pedro," Leonard said to the waiter, one of the Sternbergs distant cousins, Jacob Heskovits. As Pedro left, Leonard turned to us. "This is a specialty of this restaurant," he said, referring to the wine. "Since you two seem to be familiar with this restaurant, I'll just let you order for yourselves."

Sternberg appeared with a bottle of wine, and three glasses. And a broad grin on his face. "This is Glen Cove 1999, Mr. Hopkins," he said setting the glasses down and filling one glass. "I think you'll find it better than the San Antonio."

Leonard lifted the glass and took a sip. Whether or not he found it more to his liking, he nodded his approval.

"The wine is on me, Lenny," Sternberg continued. We all looked at him quizzically. "You've help me win a bet with my wife. All of you. Enjoy your dinner."

The waiter had been behind Sternberg, and stepped forward as the owner left. Naomi and I gave him our orders, Naomi making sure to order the most expensive items she liked. I was more conservative. From the look on Leonard's face as my wife ordered, I sensed that some sort of duel was going on between them, and that Naomi was winning. Leonard matched her in price of his selections, although they were different.

"So, Mr. Hopkins," Naomi began as the waiter left, "what do you do for a living?"

Leonard smiled at her. "I'm a lawyer." Naomi would have fell if she hadn't been sitting down. "Didn't the St. Clairs tell you?" He had scored points and was at least even, if not ahead.

"No ... they really didn't ..." she looked at me. "Val, are you holding back on me?"

"No ..." I joined in. "Leonard's profession never came up."

Leonard was now smiling as broadly as Sternberg had. "My firm is Caldwell Professional Corporation, PC. We handle most of the business affairs of THE ESTATE members in this town. Like the Mafia, THE ESTATE likes to keep its business and its affairs in the family, so to speak."

"How come you've never approached us?" my wife asked.

"We still believe it's improper for attorneys to solicit business. Besides, word of mouth gives us all the business we need. I'm sure you've had the same experience."

He was right about that. We've never had to make a cold call to represent a business since moving here.

"In fact," he continued, "I've known about you two since you first moved here. If you check the lease on your office, the papers on your house, and the legal sign-offs on most of your contracts, you'll find yours truly has done the work."

Naomi and I looked at each other in surprise and wonder. We'd not checked these things, just noted that they were professionally handled and didn't have any nefarious clauses.

"What else about us do you know?" she asked, now a little bit nervous herself.

"Just about everything there is to know. You're members of THE ESTATE, which means your sexual lives are not prosaic. You go by the honorifics of 'Mrs.' and 'Ms.' so that means that one of you is a biological male living as a woman. You're members of the St. Clair circle, so that means that you're a legally married couple, and that the husband is the 'Ms.' "

Again, Naomi and I just looked at each other. She spoke first. "You can tell all that from us being with the St. Clairs?"

"Well, not just the St. Clairs. After all, like I said, you are members of THE ESTATE. The Mrs. and Ms. titles are standard for couples with a husband who is special lady. Sometimes, however, we have two biological women who use the same protocol. Then there is speculation whether we're dealing with two lesbians or a married couple."

The meal arrived just as he finished. This gave all of us a chance to let what Leonard had said sink in. Naomi and I had not really gotten into the social etiquette of THE ESTATE beyond my crossdressing and our friendship with the St. Clairs and the others of that circle.

Leonard turned to Naomi. "How long have you two been married?"

"Seven years," she answered.

He turned to me. "And how long have you been dressing up?"

This is a question I've grown to anticipate. Naomi asked it the first time she caught me dressed as a woman. Then Helga asked it when we first met the St. Clairs at THE ESTATE. Each of the wives and special ladies, in private conversations, had also asked.

I looked at Naomi for guidance. She stared back blankly. "Since my teens," I answered honestly.

Leonard turned to Naomi. "Did you know about this when you got married?"

"Noooo," Naomi said. "We were married three years before I found out about Valerie."

Leonard nodded. "When did you accept Valerie?"

Naomi thought a while. "About a year ago."

This came as a surprise to me. I thought she had accepted me from the beginning. My shock must have registered on my face.

"That's about the time you joined THE ESTATE?" Leonard asked.

Naomi nodded.

Leonard turned to me. "Valerie, your experience is quite typical of many special ladies, especially of the St. Clair circle. You dress up, your wife goes along with it rather than divorce you, you think she's ok with it, you join THE ESTATE, you began living as a woman 24/7, including dating men. Thelma, Antoinette, Hermione, Karen—they all went through identical experiences. I was fortunate to be one of the men they dated. I would like to be fortunate enough to be one of the men you date."

We ate silently for a few minutes as Leonard's words sank in. He was saying that he expected me to fuck men and he wanted to be one of those men. Men, no a man! I looked at Naomi as we ate, wondering what she was thinking.

"Would you like to fix your make-up, Val?" she finally asked.

I nodded and we got up and went to the ladies' room. There were a few others in there, taking care of their business or fixing their make-up also. We waited until we were alone before speaking.

"Well, what do you want to do?" she asked.

"I don't know," I replied. I really didn't know."

"The man wants to fuck you, Val," she continued. "Do you want him to fuck you?"

"I don't know, Naomi," I cried, tears coming to my eyes. "I just never thought my dressing this way would lead to this."

"Ok, ok, Val. Just don't cry. We'd have to do your make-up all over again. Remember, you're a lady. A lady never puts out on the first date. And we have our car here, so getting home is not a problem. Let's finish the meal as what we are: two ladies being taken to dinner by a handsome successful lawyer. Can you handle that?" I nodded. "Ok, then. Fix your make-up and let's go."

Leonard stood as we returned, searching our faces for some sign of the state of affairs. I could not look at him. Naomi smiled at him broadly.

"So, Mr. Lawyer," she began. "What law school did you go to?"

Leonard sighed in relief. At least the dinner was not at an end. "State University."

"And how long have you been in practice?" she continued.

"Twelve years."

"With Caldwell all that time?"

"Wait a minute, Mrs. Imhof. I'm the lawyer, I'm supposed to do the cross-examination. They both smiled at this. "No, I've been with Caldwell for about five years. Spent a couple of years with another firm in another city, tried private practice. But being gay, and in the closet, the fact that I hadn't settled down by the time I was thirty, so to speak, worked against me. I had a few lesbian friends who escorted me on dates when I had to be a couple, and I did the same for them. It appeared that I was an irresponsible womanizer. About six years ago I found out about THE ESTATE. I met Helga and Thelma there. They introduced me to a lawyer with Caldwell who was also a special lady. She suggested I join the firm and move here. So, here I am."

By now I had regained enough of my composure to join the conversation. "And how long have you known you were 'gay'?" I felt uncomfortable with the word, both when used by Leonard and when I said it. Leonard wasn't.

"I guess since my late teens. I dated regularly in high school. I'm not vain, but I know I'm good looking. I never had a problem getting a date. Even lost my virginity to a girl when I was fifteen. Then one night at a party, I met my first special lady. Or special girl. She was only sixteen. Dressed as a cheerleader! Talk about stereotypes! Anyway, everyone knew it was a guy, but she looked better than all the real girls there. Toward the end of the party she was giving blow jobs to any and all. I got in line with all the others. It was the best sex I had had up 'til then. No one thought twice about being blown by a queer. As long as you weren't the one performing the act, you weren't the fag."

Leonard looked at us to see how we responded to these pejorative words. Not noting any negative reaction from either of us, he continued. "In college I got more exposure to gay life, and a more sophisticated understanding. I still dated women, but found that I rather get head from a special lady than straight sex from a coed. Like I said, I'm good looking. And gays are more into physical appearances than most women. So I never lacked for a date with them either. By my senior year, I was exclusively dating special ladies. And into law school."

I looked at him intently. "Do you still think of a special lady who is sucking your cock as a 'queer' or a 'fag?' " The bitterness in my voice could not be disguised.

Leonard looked at me just as intently. "I seemed to have given you the wrong impression, Ms. Imhof. My first gay experiences was having a special girl perform oral sex on me. That was it for a long time. I stopped thinking in terms of blow job and queer and fag in college. I just wanted to be honest with you and Naomi. I came into this orientation with all the sexual baggage of our culture. Becoming aware of what I am and how I am took time. It was—is—an evolution, not a completed process. And it's the same for you," he looked at Naomi, "and for Mrs. Imhof. I want to be part of that process. I think I can be a positive part of that process. And for the record, I've had more than one cock in my mouth, too."

Naomi and I finished eating, not immediately responding to what Leonard had revealed. Leonard poured himself another glass of wine, sipping it while watching us over the rim. I didn't know how to proceed. Fortunately, Naomi did.

"So, Leonard," she said as she put her fork down on an empty plate. "By the way, do you prefer to be called Leonard or Lenny?"

"Leonard," he answered. "I really hate Lenny. Thelma is the only one who calls me that, and that's because she can be a real bitch at times.

"Well, Leonard," my wife continued, "Val's evolution, as you say, hasn't progressed that far. She's only been with one man, and neither of us wants her to repeat that experience."

"Yes, I know about William," Leonard interrupted. "I'm not William. ... Few men are. Personally, I think he should be restricted to those special ladies of THE ESTATE whose wives are into female domination, or who themselves are into self-humiliation. Many special ladies and their wives are. Helga and Thelma and the others have their own reasons for subjecting new members of their circle to him. You'll have to take that up with them. But they also want to subject—if that's the proper term—you to me." He placed his hand over mine. "I find you very attractive, Valerie, and I want you."

I looked at Naomi again. She leaned back in her chair, looking at me, but said nothing. I gently pulled my hand away.

"Evolutions take time, Mr. Hopkins," I said demurely.

Leonard looked dejected, not knowing whether or not my statement was a rejection or a postponement.

"I think both Val and I need to think over what you said, Leonard," my wife interjected. "We'd like to think you for a very interesting—and informative—evening."

She stood, reaching for her purse. I copied her moves and followed her to the ladies' room a second time. This time it was empty.

"This will give Leonard time to pay the bill and take care of all those financial things we ladies aren't supposed to know about she said. So just fix your make-up and give him about five minutes."

We both reapplied our lipsticks, looking at each other in the mirror. I was certain I could detect a smirk on Naomi's face. When we returned to the table, Sternberg and Leonard were laughing. Leonard stood as we arrived.

"I hope the dinner was to your liking," Sternberg smoozed.

"Bella Napoli is always to our liking, Luigi," Naomi answered. Satisfied, Sternberg moved on to the other tables. "Private joke, Lenny?" Naomi said to Leonard.

He winced at the diminutive. "I'll tell you outside."

Naomi led the way, followed by me, then Leonard. He'd parked his car at the opposite end of the lot from ours, so he escorted us to our car. Before opening the passenger-side door, Naomi stuck out her hand.

"Thank you for a very pleasant evening, Mr. Hopkins," she said.

He took her hand and shook it. I stuck out my hand next, and was prepared to say the same thing, when he took me in his arms and pulled my face to his, kissing me. As I felt his tongue trying to enter my mouth, I also felt something between our bodies at the crotch level. Shocked, I realized it was my wife assessing Leonard's endowment. The surprised caused me to open my mouth to Leonard's invading tongue. I managed to put some space between us, looking at my wife in horror.

"Nice equipment," she smiled at Leonard.

"Thank you," he smiled back. He looked at me again. "May I call you this week?"

"Sure you can, Lenny," Naomi said, a smirk definitely on her face now. She opened the door and I got in, ass on seat, legs together, pivoting and swinging my legs in, all ladylike. Leonard leaned into the car and kissed me again as Naomi went around to the driver's side and got in. As she put the key into the ignition, she turned to him.

"Mr. Hopkins, you didn't tell us what you and Luigi were laughing about."

Leonard knelt beside me, placing his hand on top of mine, which was in my lap. "Remember what I said about the 'Mrs.' And 'Ms.' Titles?" We both nodded. "Well, Valerie is such a convincing lady," here he squeezed my hand, "that Luigi and Rosa had a difference of opinion as to whether she was a special lady, or whether the two of you were lesbians. Luigi thought Valerie was a special lady. When I announced that the two of you were with me, it meant that Luigi was right." By now his hand had moved to my knee.

"And that was worth a bottle ofBella Napoli'smost expensive wine?" my wife asked.

"Luigi doesn't win many arguments with Rosa." His hand was now on my shin, below the hem of my dress.

Naomi started the car and Leonard gave my leg a squeeze, then stood and closed the door. Naomi drove out of the parking lot; Leonard stood there watching us leave.