My Wife, My Pimp, Part 3: Leonard

by 1946ew

 

Thelma and I were lunching at one of the St. Clairs' favorite restaurants, having just left the beauty salon. It had been three months since I had been with William. I still could not perform with Naomi as a man, although I ate her daily to orgasms. We had adjusted to our new lifestyle, opening a manufacturers' representative firm, Imhof Consultants, in a different city than the one we had lived. This had been my old line of work, with Naomi acting as my secretary, office manager, appointment setter and girl Friday. It was only natural to continue this line of work, now with Naomi the full partner she had always been. To our clients who were also members of THE ESTATE, which were most of our clients, they knew we were a couple with a transgendered husband. To our other clients, we were two women entrepreneurs, probably lesbian. Both willingly gave us the chance to prove ourselves. Members or not, we had to show that we were competent and capable salespeople willing to go the extra mile to represent their product lines. We satisfied both.

By now I had let my dark auburn hair grow down to my shoulders. My lipstick color was a medium dark red, which contrasted nicely with the slightly ruddy foundation and blush that are now my colors. As this was a Saturday, I was wearing a casual outfit: tunic, skirt, lingerie, two-inch heels. There were two businesses in our town owned by ESTATE members which specialized in clothing for us special ladies. Both carried a special line of shapewear with padded busts, hips and rear ends, depending on the desires of the customer. I always wear a longline bra or bodyshaper or similar garment which smoothed my body shape from upper chest to hips, and let me wear breast forms. Sometimes I wear shapewear which added padding for my ass and hips as well. I always wear stockings, never pantyhose. I just love the tug of the stockings against the garters when I walk, or stand up. Keeps reminding me that I am now a woman.

I normally spent Saturday with one of the ladies, usually Thelma or Antoinette. We did normal middle-class women's things: getting our hair done, or make-overs, or manicures and pedicures, shopping, gossiping. I found out that several of the businesses in our new town were owned and operated by members of THE ESTATE, and catering to us special ladies was never a problem. We were sitting on the outdoor patio of the restaurant with a good view of the area, having coffee and talking about nothing in particular.

"Hello, Thelma," a man said as he pulled up a chair to our table. He leaned over her and kissed her fully before sitting down. He was about my height without heels, trim, with sandy brown hair and hazel eyes. He immediately stared at me.

"Are you the Valerie I've heard so much about?"

I nearly choked on the food in my mouth, and could only nod my head. Thelma, fixing her lipstick, answered for me. "Yes. This is Valerie. Valerie, this is Leonard Hopkins. Lenny, Valerie Imhof."

Leonard took my hand and kissed it. "It's a pleasure to meet you, after all I've heard, Valerie."

I looked at Thelma, quizzically. She finished reapplying her lipstick and looked at me nonchalantly. "Leonard has a weakness for ladies like us, Valerie. Ever since he heard we added a new member to our circle he's been dying to meet you."

"And you're everything they said you were, Ms. Imhof," he added.

I said nothing, trying hard to maintain my composure. I was sure his being here was not happenstance. I swallowed my food and muttered a "Thank you, Mr. Hopkins."

He looked at Thelma with mock disapproval. "Don't tell me, Thelma, that you've never discussed me with this beautiful lady."

Thelma slowly chewed the bite she had just taken. After swallowing, she looked Leonard in the eyes. "You know we always allow new ladies to take some time to adjust after being with William. We wanted to make sure Valerie was ready to continue her life as a complete woman before introducing her to you, or to others."

I was not sure what that meant, or who the "We" she kept mentioning were. Did it include just her and Helga? All the ladies and wives of the St. Clair circle? Naomi? Thelma returned her gaze to Leonard.

"I think Valerie needs a little more time, Lenny. Can I help you?"

Lenny's face alternately clouded then brightened. "Yes … yes … certainly…"

The two stood, Lenny placing his arm around Thelma's waist. She turned to me, "Please pay the bill, Valerie. I'll treat the next time."

Without waiting from my answer she turned and walked away with Leonard.

* * *

"You didn't exaggerate about her attractiveness," Leonard said as he and Thelma reached his apartment. When do you think she'll be ready?"

"You really know how to flatter a lady, Mr. Hopkins," Thelma said in mock anger. "Here I, a married lady, am about to enter your bachelor apartment to let you have your way with me and all you can think about is another lady."

By now Hopkins had opened the door and ushered Thelma in. He didn't reply as the two quickly crossed the living room and entered his bedroom. Thelma sat on the bed as Hopkins stood in front of her and let her open his pants and fish out his cock. It was hard, its eight inches pointing at her. She pulled him forward and took the head in her mouth, sucking while undoing his belt and the top hook of his pants, then pushing them down. She had to take his cock out of her mouth to push his boxers down also, but as soon as they were at mid-thigh she clamped her lips around his member again, gripping the shaft with one hand while palming his balls with the other.

When she felt he was ready to cum, she released him, stood and kissed him on the mouth, letting him taste himself on her lips and tongue. She stepped away to undress herself as he finished undressing himself. Both naked, they wordlessly climbed onto the bed and made the beast with two backs, Thelma on the bottom.

Leonard Hopkins was a sissy fucker—a man who enjoyed having sex with other men dressed as and living as women. He was not as big as William in either length or girth, and had a more romantic technique than William. For this reason, the St. Clairs preferred him to be a lady's first lover after William. He had fucked all the ladies of the St. Clair circle, and usually enjoyed a weekly tryst with Thelma. They had an established routine and rhythm, and it took only minutes after he was into Thelma that he came. She kept her legs wrapped around him as he pumped his seed into her, squeezing her sphincter to drain him. Their mouths were practically glued to each other the entire time. After nearly fifteen minutes, he pulled out and rolled off her. Thelma immediately reached inside the top drawer of the nightstand and took out a tampon, which she inserted. No use staining the sheets anymore than necessary.

The two lay silently for several minutes before Leonard spoke. "About Valerie …" Thelma poked her elbow into his ribs, hard, reminding Leonard that it was a man he had just fucked. He winced. "C'mon Thelma," he persisted. "You invited me to the restaurant to check her out. Well, I've checked her out and I want her. You and Helga know her better than me, so tell me when she'll be ready. Same deal: $1,000 if I'm the first after William, regular rates after that."

Leonard took a breath waiting for an answer. When none came, he asked, "By the way, how much is this gonna cost me?"

Thelma poked him again. "Owww!"

"I should charge you double, thinking of another lady when you're fucking me. However, you were unusually randy this time, so consider it a freebie." She decided this wasn't the time to tell him that Helga and her had decided not to charge Leonard for sex anymore. After all, he was providing them with a service as well.

Lenny smiled and rolled on top of Thelma, kissing her. Thelma started to push him off but felt him becoming turgid again. She pulled her legs up until her knees were at the cups of her bra, and felt him pull the tampon out. He's gonna have a large laundry bill this week she thought as he slid into her again.

* * *

Naomi looked at me as we ate dinner. Usually after an afternoon with the other ladies, I was quite talkative about where we went, and what we did. This afternoon, however, I had been silent, even pensive, since returning home. We had prepared dinner together, barely speaking.

"Something wrong, honey?" Naomi asked.

I looked up from my plate, staring at the empty space in back of my wife's head. "No … not really, Naomi." I paused. "Have you and the others made plans concerning me?"

Naomi stopped eating with fork in mid-air. She looked intently at me, the sign of something hidden on her face. "Well, no, honey. Not plans." I looked at her, waiting for the other shoe to fall. "Well, it's been three months, Val. You're no closer to returning to Nicolas now than the day after William fucked you. The other wives think its time you moved on."

"Moved on?"

"Well, yes, honey. That you experience someone other than William."

"And you approve?"

Naomi was now somewhat defensive. "I wouldn't say approve is the right word. It's just that you've become a woman. You look like a woman, you dress like a woman, you act like a woman. Damn it, Val, you even make love to me like a woman! The wives felt that since you've come this far, you should go further."

"And what is going further?"

"That you begin dating men!" There, she'd said it. The final step: her husband Nicolas no longer existed, and the woman he had become should start being a woman sexually as well.

I looked at my wife in disbelief. Despite the events of the past three months, I still thought of ourselves as a monogamous couple. Now she was asking me to step outside the marriage, maybe even dissolve it.

"Are you going to begin dating men?" I asked, afraid of what the answer would be.

"No. I have a husband. She satisfies my needs: financially, socially, emotionally, psychologically … and sexually. This is not what I expected when I married you, but we both went into this together with open eyes. I love being your wife, and I love you. I have no need for anyone else." Valerie began to cry. "But it's different with you, Val," Naomi continued. "I … our marriage … wasn't enough for you. You wanted something different. And because I love you, I wanted you to have what you wanted. That meant watching you become a woman. First the cross dressing, then the membership at THE ESTATE, then the association with the St. Clairs, then William. And now it means having a husband who is my lesbian lover. I don't think it will stop there. I'm afraid that I will lose you eventually. But until then, I love you and will help you become as complete a woman as you want. And the next step in that is for you to begin dating men."

We finished the meal in silence.

* * *

It was Thursday of the following week that Leonard came into our office. Being reps, we do most of our business out of our home, but it is necessary to maintain an office to be seen as legit, and to meet clients in a professional atmosphere. The office is essentially a large office room where both Naomi and I have our desks, and a reception area. Usually, we keep the door between our office and the reception area open so we can see whoever enters. One of us is usually visible when anyone enters. Leonard came in and stood in front of the reception desk, looking directly at me. I came out to greet him.

"Good Afternoon, Mr. Hopkins," I said, extending my hand. He took it in both of his, holding it rather than shaking it. By now, Naomi had appeared at the doorway. Leonard looked over my shoulder at her. I turned, and introduced her. "Mr. Hopkins, this is my wife, Naomi. Naomi, this is Leonard Hopkins."

The two nodded at each other. I gently pulled my hand from between Leonard's, as Naomi came up to stand slightly beside, slightly behind me.

"You're as lovely as I've heard about, Mrs. Imhof," Leonard said.

"Thank you, Mr. Hopkins," my wife replied.

"I would like to invite you to dinner," Leonard said, looking at me.

"I … I …" I stammered.

"Oh, not just you, Ms. Imhof. Both you and Mrs. Imhof." He said.

Naomi and I looked at each other, puzzled.

"I'm sure Thelma must have discussed me with you after we met, Ms. Imhof" He continued.

I nodded. Thelma had called me Sunday afternoon and explained about Leonard, that he was quite taken with me, and that she, and the others, thought he would be the perfect man for me to go out with next. I relayed all this to Naomi, along with my apprehensions about dating men. Naomi was noncommittal, mere stating that she thought I should consider what Thelma had said, but it was solely up to me.

"Yes …yes, Mr. Hopkins," I replied, "she did speak about you."

"Please, call me Leonard. And may I call you Valerie?" He looked at my wife, "And may I call you Naomi?"

"Yes," my wife replied for both of us. "Leonard. Valerie. Naomi."

"Thank you," he smiled, looking at my wife. "The invitation is for both of you, Naomi. I understand Valerie may be somewhat reluctant to date men, but I do find her very lovely. If we three have dinner together, maybe she'll be less intimidated by the situation. Besides," he now turned his smile to me, "being seen with two such attractive women can only enhance a bachelor's reputation."

"That sounds reasonable to me," my wife replied. "How about you, Val?"

I didn't know what to say, looking from Leonard to her and back again. Was this something they had planned? Was it something Leonard and the St. Clairs had planned that Naomi was going along with? Or was it Leonard acting on his own? No matter. My wife wanted me to go on this date. And so did I!

"I … I … I'm not sure, Naomi." I stammered.

"What's there to be not sure of, Val?" she insisted. "Mr. Hopkins … Leonard … is asking two women to have dinner with him. We both like to eat. We both like being entertained. And we both like male companionship."

I threw my most daggerly look at her.

"Then it's settled," Leonard beamed. "Tomorrow. Give me your address and I'll pick you up about seven, ok?"

I didn't know what to say. Thankfully, Naomi was more experienced in this matter. "Not so fast, Mr. Hopkins," she said, emphasizing his name. "Why don't you call us and tell us which restaurant you have in mind, and we'll meet you there."

Leonard looked at Naomi, aware that I was to be no easy conquest. "Fine, Naomi. And your phone?"

Naomi took one of the business cards from its holder on the desk, wrote our home phone number on the back, and handed it to him. He looked it over, obviously memorizing it, then put it in a wallet bulging with similar cards. I wondered if the St. Clairs, and the others had their home numbers on cards in his wallet.

"Tomorrow, then," he said, extending his hand to Naomi. She shook it professionally. When he extended his hand to me, I tried to do the same, but again he took it in both hands, this time kissing it as he had done at the restaurant. I blushed. He smiled at both of us again, and left.

Naomi looked at the closing door, then rushed and locked it as soon as it closed, leaning against it and looking at me. "Wow!" she gushed. "You didn't mention that he was such a hunk?"

I just looked at her. I was conflicted as to what to feel. My wife was encouraging me to go out with a man, a man whom she found very attractive herself!

"I don't think of men that way," I meekly rejoined.

"Well, you should begin thinking of him that way," she countered.

The rest of the afternoon was a waste as I couldn't concentrate on anything, and neither could Naomi. We drove home in silence, and barely spoke at all while fixing and eating dinner. Sensing that I was disturbed by that afternoon's events, Naomi tried to cuddle me as we watched TV, but I didn't feel cuddlesome. That night, she tried again to arouse me, without success. We ended the night sleeping spoon fashion, her behind me, her hand on my still flaccid dick.

* * *

Friday we decided not to go to the office. Most of the work that we needed to do could just as easily be done from our home office, and we were not expecting any business calls, or making any. The tension in our home you could cut with a knife. A dull one. We went through our routines: breakfast, work, lunch, trying to work, etc., waiting for THE CALL. It came about 4 p. m. Naomi answered.

"Imhof residence. Yes, this is Naomi. … Yes, Leonard, I recognize your voice. … Bella Napoli? Yes, that's fine. We've eaten there several times. Excellent choice, Mr. Hopkins. … Yes, 8:00 is perfect. We'll see you there."

She turned to me. "Well, you heard. Bella Napoli at 8:00. Let's get ready. You shower while I think of what we should wear."

I dutifully went to our bedroom and undressed, then took my shower. When I came out Naomi was still musing over what dresses we should wear. She'd already laid out my lingerie: a pastel green body briefer from one of the specialty shops for us special ladies. It contained a built-in 36C bustline, padded hips, and padded rear, reaching down to the top of my thighs, with garters for the sheer light tan hosiery she'd selected. She decided on a simple sleeveless sheath dress with a scoop neckline for me, emerald green to match the alligator pumps, handbag, and clutch purse set she had bought for our last anniversary. I was again disturbed that the first time I would wear these shoes or use the purse and handbag was on a date not exclusively between me and my wife. Faux emerald and gold earrings and necklace, and a slim gold wrist watch completed my ensemble.

Naomi chose a bra-waistcincher-panty set, beige, and the same color stockings as mine. Her hair being dyed a light shade of brown, not quite blonde, she chose a beige suit with a white shell, looking like a businesswoman on a business dinner, which in fact she was. She also wear classic pumps, also in beige, white pearl earrings and single-strand necklace. This was her standard "have to have dinner with the client" suit. It was clear she was not going to outshine me. She made it a point to have on both her engagement ring and her wedding ring. She also insisted that I wear the woman's wedding band we'd purchased when I first started going out as a woman to ward off men. It didn't.

We were ready about 7:00 p.m. It took about 30 minutes to drive to the restaurant, so we left about 7:15, Naomi driving. On the way, she gave be brush up pointers on having dinner with a man.

"Remember, let him order. You tell him what you want, and he tells the wait person. Second, this is an Italian restaurant, so he'll probably order wine. Agree with whatever he orders, no matter what you think. Whenever there is a lull in the conversation, ask him about himself. Men never tire of talking about themselves. If you have a serious problem, just say you and I need to go to the ladies' room, and we'll discuss it there."

"Is that how you trapped me?" I asked in mock innocence.

She threw me a look. "Trapped isn't exactly what I did to you. You were begging to be hitched. If only I knew it was to get into my clothes, not into my pants."

That hurt. Naomi regretted saying it as soon as it was said, but you can't unring a bell and the peals of that sentence would reverberate for a very long time. Naomi pulled the car into the restaurant's parking lot at 7:47. We checked our makeup and then entered.

"Welcome, Mrs. Imhof, Ms. Imhof," oozed Bernard Sternberg, owner of the restaurant, known to most of his patrons as Luigi. "I'm so sorry. We're booked solid tonight. If only you'd made a reservation."

"It's ok, Luigi," came a voice from behind us. Turning, we were greeted by the smile of Leonard. "They're my guests this evening. Hopkins, party of three."

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 Napoli has 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 business¾ and its affairs¾ 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. The Helga asked it when we first met the St. Clairs at THE ESTATE. Each of the wives and 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 liked 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 down her fork 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 of Bella Napoli's most 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.

* * *

To Be Continued.

  

  

  

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