St. Clair Ladies Circle: Leonard

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Valorie and wife Naomi have dinner with a CD admirer.
6.4k words
30.8k
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Part 2 of the 4 part series

Updated 08/30/2017
Created 07/07/2006
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1946EW
1946EW
43 Followers

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 in which 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—what cosmetics companies like to call by some wine, like Sangria or Burgundy or Merlot. The color 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 she and Helga 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 going to 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 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 fromLily Marlene's, 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."

1946EW
1946EW
43 Followers
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