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St. Clair Ladies Circle: 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 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.



St. Clair Ladies Circle: Leonard Pt. 2



POSTCARDS FROM THE ESTATE:

THE ST. CLAIR LADIES CIRCLE—MY DATE WITH LEONARD

[Author's Note: The St. Clair Ladies' Circle: My Date With Leonard is the full title of this submission. The title in Literotica meets its requirements, which do not permit long titles. This is the sequel to The St. Clair Ladies' Circle: Leonard. The submissions are not necessarily chronological, as back stories are sometimes needed to introduce characters not directly within the storyline. In response to some of the comments on my other submissions, I must caution the reader to remember this is a work of fiction! These people do not exist. THE ESTATE is not a real place, nor is the town in which the St. Clairs live!]

"Yes, Leonard, seven will be fine."

"Hot date?" my wife asked as I put the phone down.

I looked at her with a combination of expectation and fear, needing her approval, acceptance, and assistance. "I guess so. Leonard has invited me out to dinner again. He's picking me up at seven."

I didn't need to say more. It had been a week since our dinner with Leonard. We both knew that tonight I was going on a date with a man with the full knowledge that he wanted to fuck me. I looked at Naomi pleadingly.

"Would you like me to help you get ready?" she asked.

"Oh please!" I shouted.

She stood and led the way to our bedroom. "Go shower while I figure out what you should wear."

I showered thoroughly, even taking time to douche. Half an hour later, I emerged from the bathroom to see what my wife had prepared. Instead of my standard long-line bra she had a merrywidow with garter straps, which was less restrictive than the bra. To fit into this, Naomi produced a set of C-cup faux breasts.

I looked at her in shock. "How long have you had these?"

"Marlena called Wednesday, saying they were ready. You were out of the office, so I picked them up." Naomi said, placing the forms against me to get an idea of their fit. Marlena Schwartzmann owned Lily Marlene's, a dress shop—and more—that catered to us special ladies. "Maybe you ought to put the merrywidow on."

I stood and put it on, Naomi fastening it from the back. She then put the breast forms into the cups and adjusted them until she was satisfied. Next she pulled back the top and put adhesive along the top portion of both forms, pressing them against my skin.

"Just let them set for a few minutes, then we can glue the rest of them on. Here, put your stockings on."

The stockings, as well as the rest of the lingerie were peach in color. I sat on the bed again, rolled the stockings up my shaved legs, attaching them to the garters. Naomi had me stand again, undid the top part of the merrywidow and rolled it down to my waist. She then lifted the bottom of each breast form, applied more adhesive, then pressed it down in place. She then handed me my panties. They were specially made for special ladies like me, with padded buttocks and hips, and a special pouch and control panel to present a feminine front, sort of combination gaff and girdle, courtesy of Lily Marlene's designing. I slipped them on.

Merrywidow, breast forms, stockings and panties on, Naomi next presented me with a slip. It completely covered the merrywidow and ended about three inches below the knee. "Go put on your face," she commanded. As I did so, she laid out a dress I had never seen before. It was a sleeveless, V-neck, empire-waisted dress with the bottom flaring, reaching to mid-calf, peach, in rayon,. She held it up and I stepped into it. As she zipped up the back, I looked at myself in the mirror, amazed that even I could not tell I was biologically male. I looked like a stylish thirtysomething woman dressed for a romantic evening.

Next came my shoes, a pair of 3-1/2" three tone pumps: peach on the inside, flesh-tone on the outside, with a tan toe. Naomi finished my look with a simple one-strand pearl necklace, matching earrings and bracelet. My clutch purse matched the shoes. Just as she finished the doorbell rang. We exited the bedroom together.

Naomi opened the door while I stood in the living room. Leonard was wide-eyed with lust when he saw me.

"Wow!" He quickly covered the distance between us, put his arms around me and kissed me. By now I was getting used to being kissed by a man; well at least this man. I put my hand to his chest as I returned the kiss. Breaking the kiss, Leonard ushered us out without ever speaking to Naomi. I doubt if he even saw her.

On the ride to the restaurant, Leonard could not stop telling me how beautiful I looked. I tried to change the topic of conversation several times, but it wasn't until we were seated in the restaurant did he realize his gushing and fawning might seem inappropriate. The restaurant he'd chosen was Cévennes, one of the more expensive restaurants in the town. We began discussing some of our mutual clients, nearly all members of THE ESTATE, and their personal quirks, much as we had when he took Naomi and me to dinner.

"Good evening, Monsieur Hopkins. It is so nice to have you visit us again. And what will you and the lady be having?"

The waiter did not indicate anything special in the way he said lady. He nodded in my direction when he said it, but otherwise his attention was on his tip: Leonard Hopkins. 

"Why don't we start with soupe froide aux herbes? We'll decide the rest of meal later."

"Excellent, Monsieur Hopkins," the waiter said unctuously. Bowing, he left the table. I noticed that he had not written anything down. I watched him as he reached the waiters' station, where he punched everything into a screen.

"The only thing French about this place are the prices," I noted to Leonard.

Leonard looked at the waiters' station. "Oh, not really. The cooks really are from France, and learned their craft there. The owners insist that the waiters be called that and not 'servers.' And there are no female waiters. If this was a regular town, this place would have a dozen discrimination suits to fight every week. Most of the attitudes are Gallic, but France is a large country, and there is probably more conflict in the kitchen here than in the U.N. But the food is five-star. I'm surprised that you and Naomi have never eaten here."

"This place is a little beyond our budget," I informed him.

"I don't think that'll be a problem after tonight." The waiter arrived and I let Leonard order for both of us, not really understanding what he meant by what he said.

After the waiter left, Leonard continued. "Most of the non-members of this town have no idea what THE ESTATE is. Some of them know of THE ESTATE, and think it's some exclusive club that they would like to join, for business reasons, not knowing its sexual nature. Others are completely in the dark."

"Are there any non-members who know all about it?" I asked.

"Only one that I know of," he replied. I waited for the revelation. "Ted Hanratty."

"Hanratty!" I said, startled.

Theodore Hanratty owned 22nd Century Imports, one of our biggest clients. We represented several different lines of his products, but shared his business with several other manufacturer's reps. He represented a sizeable amount of our business, while we were just one of many reps to him. Or so we thought.

"Yeah. In fact, it was Ted who informed me about you." Again I waited for the other shoe to drop. "Ted has a thing for ladies like you the same as me. Only I'm open about it, he's not. He's had his eyes on you ever since you moved here. Couldn't be sure whether you were a woman or a special lady, until he saw you having lunch with Thelma one Saturday, Karen and Antoinette the next. As you know, Ted's a very smart man. He put two and two together. You're part of the St. Clair circle," he said matter-of-factly.

"What do you mean by that?" I asked.

"The St. Clairs and their group are known to be married couples in their thirties and forties in which the husband is a crossdresser who can readily pass as a woman."

"So just by being with the St. Clairs tells everyone at THE ESTATE that I'm a crossdresser?"

"More or less. The only question is which is the wife and which is the husband. Also that you've been fucked by William."

I thought about this. Every one at THE ESTATE, that means every one of our clients, and Hanratty among the non-members, knows I'm a man living as a woman whose been fucked by the biggest dick at THE ESTATE. Finally, I asked. "You said he informed you about me?"

Leonard looked sheepish for the first time that night. "Well, like I said, Ted and I have the same weakness. He's also a client of Caldwell's. He's been with some of the ladies of the St. Clair circle, as I have. One day we were at the same bar after hours and he asked me if I'd tried out the new lady."

I sat back, taken aback. "So, I'm just another conquest?"

Leonard looked at me, "Valerie, we all know what we are and why we're here. You are a very attractive lady. I like ladies like you. I don't consider it a conquest, just a new experience. For both of us."

I began to have second thoughts. It must have showed on my face.

"Valerie, I don't know exactly how you see yourself. Some ... CDs," Leonard seemed uncomfortable with the word, "see themselves as women, period. Some see themselves as men in dresses, period. Some see themselves as gay, others deny that they are gay. And some see themselves as expressing their feminine side, while not denying their masculinity. And there are all other types, too. I'm gay. I'm a man who has sex with other men. My only bent is that the man must be dressed as a passable female. Ted has the same bend, only he denies that he's gay or bisexual or that there is anything homosexual in his having sex with another man, because in his mind, and the mind of his lovers, they're women. I have no illusions as to what you are. You make a very beautiful woman, and I want to make love to that woman."

Leonard was nothing if not bold and direct. Dinner came and as we ate I was thinking what he expected me to do to him this evening. What did he plan to do to me? I only knew two things for sure. I was going to suck his cock, and that cock was going to ream my ass. After all, we're two gay men, and that's what gays do, right?

The meal finished, Leonard paid the bill and escorted me out of the restaurant, his arms around my waist. Except for the fact that I was slightly taller than him, we looked like any other romantic couple at the restaurant. His apartment was about a ten-minute drive away, the drive made in silence. Only when we were inside his apartment did he take me in his arms again and kiss me. I totally submerged myself into my femininity, throwing my arms around him and kissing him back. We stood like this for minutes, lips pressed together, bodies pressed together, me feeling his manhood grow until it was obvious it was painful in its confines.

I broke the kiss, stepping back and sitting on the sofa, pulling him towards me by his belt. I unfastened it, then his pants, pulling them down. His cock popped out of the opening of his shorts, nearly hitting me. It was not as big as William's—very few can be—but it was large, about 8" long, and 2" wide. I remembered how Naomi used to suck me, how I had sucked William, and how the other ladies had done the same. I looked up at Leonard, his face a mask of unrestrained lust. Without removing my gaze, I opened my mouth and guided his cock inside. He closed his eyes as I closed my lips around the head. I sucked gently, gripping his shaft with one hand while reaching inside his boxers to run my fingernails through his pubic hairs and gently scratch his balls. He came.

His cum was not as effusive as William's, nor as forceful. But it was enough. It filled my mouth and drained Leonard to the point that he had to grab my shoulders to stable himself. I swallowed, realizing that I had taken a man's cum in my mouth for the second time. I kept my lips glued to his cock until he finished spurting, licking the cum that had oozed out of the side. Leonard pulled me to my feet and kissed my cum-smeared lips. Breaking the kiss, we just stood there grinning at each other. By mutual consent, we held hands and started towards the bedroom. That's when Leonard fell flat on his face. His pants had completely hobbled him!

Laughing, I knelt and untied his shoes, removing them, his pants and his boxers. I then kissed the insides of his thighs, working my way up to his crotch, where I licked the area behind his balls, his balls, and his cock, still shining with a cum sheen. I would have gladly sucked him off then and there, but he had other plans. By the time he stood up, he was hard again. He shucked off his suit coat, and again took my hand, leading me into the bedroom.

Leonard stood me next to the bed and kissed me again. He then turned me so that my back was to him and unzipped my dress, pushing it from my shoulders and letting it pool at my feet. I turned, reached down and pulled off the slip, leaving me facing him in my lingerie and heels. Slowly, tentatively, I pushed my panties pass my hips and down my legs until they fluttered to the floor. He reached around me and undid the back of the merrywidow, letting it fall as far as the garter straps would permit. I reached down and unhooked them, letting the merrywidow fall to the floor. While I was unhooking the garters, Leonard removed his shirt and tie. We stood like that, facing each other, me in stockings and heels, him naked except for his socks.

Instinctively we embraced again, our tongues dueling. Leonard trailed kisses down my throat into the valley created by the faux breasts. The breasts! I had not even thought about them! They did not seem to matter. Leonard kept going south until he was on his knees before me. He took me in his mouth and sucked me gently. For the first time since William I responded. Not hard, but a little more firmness than I had experienced with Naomi. He pushed my thighs gently and I fell back on the bed. He spread my legs and licked my balls, the area behind my balls, then kissed the inside of my right thigh to the top of my stocking, switched to the left leg, and kissed his way back to my crotch. It all felt wonderful!

He stood and reached inside the nightstand for a condom. As he was putting it on I removed my heels and scooted to the center of the bed, laying on my back with legs splayed. Leonard applied some lubricant to his sheathed cock, then climbed on the bed and positioned himself between my legs. I looked down the valley of my breasts at the monster that was about to enter me, then at the proud face of its possessor. Proud, but not prideful. Confident but not cocky. Cocky! I had never seriously considered the meaning of the word! I brought my legs up until my knees kissed the nipples of my faux breasts. Accepting my surrender, Leonard placed the head of his cock at my hole.

"Take a deep breath," he commanded. I did. "Now let it out slowly." As I did so he pushed himself steadily inside me. Once inside, Leonard laid on top of me and kissed me, deeply. I responded, wrapping my legs around him, rubbing his side and back with one hand while gripping the back of his head with the other. He assumed the classical male part of the missionary position, forearms on either side of my head as he rode my ass. And rode my ass. And rode my ass!

I did not experience the pain I had with William, probably due in part to having been opened so fully by him, and Leonard's smaller size, if 8" can be considered small! Leonard's technique was different. He entered and exited me with much smoother strokes, seeming to care that I enjoyed being fucked as much as he enjoyed fucking me. And he was an expert kisser! Plus I enjoyed the feel of his body on mine, the way his stomach sort of surfed on me. When he began to increase the rapidity of his movements, I gladly planted my feet on the bed and lifted my ass, giving him freer access. When he came, I enjoyed the twitching of his cock!

Leonard lay on top of me as I lowered my hips, his cock still twitching and spurting inside me. For several minutes we continued to kiss. As he recovered he began to mutter sweet nothings to me. How he enjoyed what had happened. How he had imagined it would be like that. How beautiful I was, and how happy I had just made him. I responded in kind: telling him how much I enjoyed it too; how now I knew what being made love to, not just fucked was; how I enjoyed pleasing him.

After about ten or fifteen minutes of this he pulled out. For the first time I realized one of the advantages of a condom: no cum oozing out of your ass! Of course there was still the lubricant and the secretions of my ass, but these were mainly on Leonard's cock. Leonard swung over me to sit on the side of the bed. He reached for the towel that was on the nightstand and placed it under my ass, leading toward the edge. I slithered onto it until I was sitting next to him, leaving a messy smear. My stockings were bunched around my ankles. Looking across the room at the mirror over the dresser, I saw that most of my make-up was smeared. Looking at Leonard I saw quite of bit of it on him. He removed the condom, took my hand, and led me to the bathroom.

We showered together, me mostly standing in the shower as he washed us both, directing the spray of water where needed, especially my ass. Several times during this he took me in his arms and kissed me. Cleansed, he toweled us both dry. Returning to the bedroom, he removed the soiled towel and replaced it with a clean one. I didn't think about the routine, but in retrospect realize that he had done this many times before. He sat me down on the bed, produced another condom and stood before me. I knew what was expected. But I wanted to be coy.

I got up and went to my purse, still in the living room, returning with my makeup kit. Leonard was now sitting on the bed. I went to the mirror and carefully applied a thick coat to my lips. I then turned and went to him, kneeling before him. He lay there on his elbows, looking down his body as I took his cock in my hand and guided it to my mouth. I lovingly took the head in and sucked, reveling in the taste of his cock. I deep-throated as much as I could, leaving a lipstick smear as I brought my lips back to the head, which I then kissed. I was about to deep-throat him again when he placed his hands on my shoulders. I looked into his eyes as he sat up. The message was clear. I placed another condom on him and rolled it down, thinking how many times I had done this to myself, an action now restricted to pulling on my stockings.

I lubed him, then handed him the tube and climbed on the bed on fours for him to return the favor. The feel of his fingers in my ass felt almost as good as his cock. He finished the lubrication then guided me to my back, placing my ass again on the towel. As he got into position, I raised my right leg straight into the air, marveling at how feminine it looked even without the hosiery. He again placed the head of his cock against my hole, pulling my uplifted leg against his body. He kissed the ankle, moving to my calf, letting the leg rest on his shoulder. He leaned forward, scissoring me, driving himself into me in one long stroke. I grabbed his sides as he pumped me gently, kissing me all the time.

Despite the awkwardness of the position, I enjoyed the stress it put me under: the feel of my leg against his body, his cock moving in and out of me. He kept this up for some time before he began that rapid movement signaling his cumming climax. When he came, he simply slid into me all the way, twisted slightly to release my leg, then lay on top of me, kissing me as his cock pumped its life force into me. This time he went softer much faster than the first time. He rolled off of me and lay beside me, running his hand along my body looking at the ceiling. When his hand reached my cock, I tensed. It was not necessary. Leonard slowly and methodically masturbated me, getting a respectable rise out of me. We lay there, me petrified, while Leonard fisted my cock, pumping it gently until suddenly I came! He kept pumping me, letting my cum ooze over the head of my cock, down my shaft and onto his hand. When I finished, he wiped his hand on the towel, rolled on top of me and kissed me again, positioning himself so that his cock was on top of my now deflated cock.




St. Clair Ladies Circle: Leonard Pt. 2



"Would you like to spend the night?" he asked.

I could only respond by kissing him again. Breaking the kiss, he again led me to the bathroom where we cleaned ourselves a second time.

"Bend over," he commanded when I thought we were finished. I did as told. He then produced a tampon, coated it with what I now knew was the astringent cream from THE ESTATE, and inserted it into me. He then led me back to the bedroom where he produced a baby-doll nightie in peach.

"My favorite color," he said.

I put it on, as he removed the second towel from the bed and deposited it in the clothes hamper in the bathroom. We kissed a final time and climbed into bed as if we were long-time lovers. Leonard was soon fast asleep. I remained awake long into the night wondering about what had happened that night. Heloise's suggestion that maybe the only way for me to be a husband to Naomi was to be a woman to someone like Leonard kept running through my mind.

* * *

Saturday morning I woke to Leonard's kissing me and handling me, his hand inside the panty of the baby doll. I got harder than the night before, but not as hard as with my wife. Leonard made love to me again, missionary style. I never imagined how important it is for the woman to be able to look at the man fucking her, to be able to kiss his face, not just his lips. I don't know why missionary style is so joked about. For a woman, it's the best possible position. I lay there, on my back, my arms and legs wrapped around a wonderful man who was riding my body, his dick entering and leaving me rhythmically, my knowing that I was giving him pleasure and that soon he would express that pleasure by cumming inside me.

But he didn't. He turned me onto my hands and knees and began fucking me doggy style. All the time he was doing me this way he kept jacking me until I had a regular erection—the kind I used to have with Naomi. When he was ready to come he kept jacking me as he pumped me, like he was jacking himself off. And we came together, him buried in my ass and me spurting cum all over his hand. We cleaned up again, this time Leonard helping me place a maxi-pad in the crotch of the panty as I pulled them up.

"There's always some residual leakage," he informed me. He then walked to a closet and produced a satin robe, also in peach.

"Were you expecting I would spend the night?" I asked, somewhat perturbed that he would make such an assumption.

"No, these belong to Antoinette," he said. The look on my face must have expressed my pique. "Valerie," he sounded exasperated, "you are not the first woman to spend a night here. Thelma, Antoinette, Hermione, and Karen have all been here. And others. Like I said when we had dinner with your wife, I have a preference for women like you. But I'm not going to fall in love with you, anymore than I did with them." He then opened the closet. There were several women's garments on hangers, plus a set of drawers labeled 'Thelma,' 'Antoinette,' 'Hermione,' 'Karen,' and a few others I didn't recognize. "You women leave things. Intentionally or accidentally, I'm never sure. You and Antoinette are the same size."

I walked to the closet and looked at the collection. There were a few dresses, some of which I recognized being worn by Thelma or Hermione. Mostly there was lingerie: panties, stockings, bras, in the drawers. I turned to him. "Do you plan on having a drawer with my name?"

"Yes, I do," he said matter-of-factly.

I returned to the bed and picked up the robe, putting it on. I returned to the closet and selected a pair of mules that were about my size. Wordlessly, we went to the kitchen where I fixed breakfast—Denver omelets, toast, orange juice, coffee.

"Would you like to spend the weekend?" Leonard asked as I set places for both of us.

I had not thought about spending that much time with him. I had went out with him because Naomi and the others expected it of me. Now I wanted to spend time with this man, to be his woman! "I don't have anything to wear," I evaded answering. I had only the evening dress. Wearing another lady's robe was one thing; wearing the dress she had worn to be fucked in by the man I was fucking was another.

"We can go back to your place and pick up some more clothes," he suggested.

I wasn't ready for that either. I wasn't sure how I felt about being with Leonard, but I knew it was more than going through another ritual or stage or phase. I was no longer a man in drag. I had been thinking of myself as a woman for the last few months. I was now a woman, with a man I wanted to be with—and whom I wanted to fuck me as a woman all weekend long!

***

Naomi was sitting in the living room when we walked in. She looked at us expectantly.

"Afternoon, Naomi," I said as if just returning from morning shopping.

"Good afternoon, Naomi," Leonard said, taking a seat in one of the armchairs.

Naomi said nothing, just looked at us. Or rather glared.

"Please entertain Leonard while I pack some things, will you, honey?" I said, flouncing toward the bedroom. I had no sooner entered than Naomi slammed the door shut behind me.

"Pack some things?" she said, incredulously.

"Yes," I tried to sound nonchalant. "Leonard's invited me to spend the weekend."

"And you're going to do it!"

"Yes," I responded, facing her. "I can't explain it, Naomi. I'm a woman now. Completely. I don't ever want to be Nicholas again! I enjoyed being taken out by a man, pampered by a man, fawned over by a man, kissed by a man, and fucked by a man. Or at least by this man! I enjoy being a woman, not just dressing or acting like one."

I had already pulled out an overnight case and opened it on the bed. Naomi went to my chest of drawers and opened one of them. "Well, you're going to need a change of underwear for tomorrow," she said, tossing me two pairs of panties, some bras, and stockings. She then went to the box that had contained the fake breasts and pulled out another item. She held it up for me to see. "If you're gonna act like a cunt, you should at least have one."

The words were mean and hateful and hurt. I snatched the latex pussy panty from her and put it on the bed, then stripped naked. With venom in my eyes I put it on and looked at myself in the mirror. Like everything else we got from Lily Marlene's these were perfect. The skin tone matched my own so that, like the breasts, they blended into my body. In addition to the fake cunt, the panties—a pantyleg style—also had padded hips and a rounded derriere. Looking at myself in the mirror I saw a very sexy thirtysomething with full breasts, a thin waist, nice hips, shapely legs. Talk about wanting to fuck myself!

I stared defiantly at Naomi. She looked at me appraisingly, then went to her closet, returning with one of her favorite sundresses, a light pink halter with deep decolletage and a very low back. I put it on. On her it stopped just above the knees. On me it reached only to mid-thigh, if that long. While the intent was to make me look like the slut she now thought I'd become, the effect was to make me look ultra sexy: no underwear, my breasts filling the cups of the dress, the hint of bare cunt whenever I sat down. I loved it! I picked a pair of wedge sandals with wrap-around straps to complete the look.

Naomi came over and sat on the bed as I finished selecting items—blouses, skirt, dress for dinner, another dress less revealing than the sundress.

"Valerie," she said as I closed the suitcase, "sit down." I looked at her doubtfully. "Please." I sat beside her. She looked at me and took my hands in hers. "I'm sorry about that cunt remark. It was spiteful and mean and ... bitchy. I'm happy for you, Valerie. And I'm sad about Nicholas."

For the first time that weekend I thought about what my transformation might mean to my wife. "Oh, Naomi," I cried, "I'm sorry. I've been so concerned about what was happening to me, I didn't think about what it was doing to you."

Naomi put her arms around me. "Don't cry, Val. I knew it might come to this. I hoped it wouldn't, that I could have both Valerie and Nicholas, but I agreed to this with my eyes wide open."

"But it's not fair to you, Naomi," I continued crying.

"Yes it is, Val," she comforted me. "We're married, for better or worse. You're not gonna get rid of me. We got into this together, we'll get through it together. Now, I want you to have a good time with Mr. Hopkins. Just remember, he's your lover, I'm your wife. I'm gonna be here tomorrow when you come home. And this is your home! Yours and mine."

We hugged and we both cried. "Now fix your face and let's go downstairs," she said.

The look on Leonard's face was seconded by the tenting of his pants when I walked into the room. Both Naomi and I were thinking the same thought: If a man looking like a woman could have this effect on him, why couldn't a woman?

Leonard didn't say anything, just took me into his arms and kissed me, as he had the night before. He gave Naomi a shit-eating grin as he picked up my suitcase and practically pushed me out the door. Naomi watched us from the doorway, dialing her cell phone.

"Helga, Naomi. ... No everything's not ok! My husband just packed a suitcase to spend the weekend with someone else! ... Yes, I knew it could come to this, but now that is has happened, I'm not at all pleased about it! ... Yeah, I'll be here. I've got no place to go and no one to go there with."

***

As he held the car door open for me, Leonard whispered "Beautiful. You look absolutely beautiful."

As I sat down I made it a point to spread my legs so that the dress rode up and he got a shot of my false pussy. Leonard smiled, closing the door and putting my suitcase in the trunk. As he sat down, he turned to me and asked, "Would you mind if I showed you off?"

My expression communicated my lack of understanding.

"I have some clients who don't know about my sexual orientation," he explained. "Being seen with a sexy woman wouldn't hurt my image."

"You think I could pass that well?"

"Valerie," he smiled, "every straight man in this burg who sees you will want to fuck your brains out!"

"And what about men like you?" I coyly asked.

"They'd want to fuck your brains out too," he laughed, pulling into the street. "And I'm the lucky man who's going to."

He headed for the municipal golf course, the town's concession to class distinctions. If I had any reservations about passing as a woman, they were all erased when we walked into the club house. Every eye turned to watch the stunning woman in the mini-sundress with nothing on underneath. Leonard was right. Those who thought I was a woman wanted me. Those who knew I was a special lady wanted me too! I felt wonderful, knowing the power of a woman who could turn heads—and cause them to rise in their pants! I put my arm in Leonard's and we sashayed past the bar to a table in the center of the restaurant of the club house. As I surveyed the crowd, knowing who was and who was not like me, I spied Ted Hanratty sitting at a booth in the most hidden corner of the restaurant with Marlena, owner of Lily Marlene's, and three other women. One woman looked to be in her teens or twenties, the other two in their early forties. I recalled what Leonard had said about Hanratty and wondered which of the older women was a special lady. All five looked at us, Marlena with pleasure, Hanratty with lust, the two matrons with a mixture of envy and jealousy, the nymph with boredom. I smiled in their direction; only Marlena smiled back.

We ordered a light lunch, salad for me, a sandwich for him, and drinks. Several men made a point of passing by our table to look down my dress or check out my legs. I made a point of crossing them and recrossing them during lunch. We spent about an hour there, discussing nothing in particular when Leonard decided that his reputation with both the straights and the knowledgeable was sufficiently secured for us to leave. Again we sashayed out, me switching my hips in a sluttish fashion. Leonard had parked his car where it could be seen from the club house windows, especially the restaurant. After he opened the door for me and went to his side of the car, I got a wicked idea in my head.

"Do you really want to enhance your reputation?" I asked as he sat in the driver's seat. He looked at me, confused. "Just put your hands on the steering wheel."

As he did so, I unzipped him and pulled his boner out of his pants. He had been hard the minute I came down in that sundress, and the attention I attracted at the club house had done nothing to lessen his arousal. His cock pointed to the roof of the car. I leaned over and took him in my mouth, making a point of bobbing up and down the full length of his 8" cock. Anyone and everyone passing by the car could see a woman blowing a man. Despite the tint of the windows, many in the club house could also see the same thing. Those who couldn't were soon apprised of the event, and an audience soon gathered at the windows. Leonard didn't last long, having been aroused for over an hour. I swallowed his cum, then licked his head clean.

"Drive by the waste can near the entrance," I instructed Leonard.

He tooled the car to the entrance, stopping so that my door was next to one of the waste cans. My window was already rolled down. I slowly wiped my mouth with a tissue, making sure lots of lipstick and cum were on it, then tossed it in a high arc into the waste can. I then turned and kissed Leonard, squeezing his dick, which was still outside his pants. Reclining my seat, I pulled my sunglasses over my face and licked my lips. Out of the corner of my eye I saw the valets trying to look like they weren't looking, shit-eating grins on their faces. Leonard also had that grin as he looked at me and shook his head. We were both satisfied with our performances as he drove off.

***

Back as his apartment, I couldn't wait to get out of that dress. First, it was my wife's, and I felt that I had somehow betrayed her by what I did. Second, that dress wasn't me, nor what I did. Or was it? After all, I was now a sissy. Yes, sissy! S I S S Y! I wear panties and bras and stockings and heels. I wear my shoulder-length hair in a woman's style. I wear make-up and paint both my fingernails and toenails. I've been fucked in the ass while lying on my back by not just one man, but two. I am a cocksucker. And I enjoy it all!

Naked, I looked at myself in Leonard's bathroom door mirror. I looked like a woman. Breasts, cunt, hips, ass. I turned to admire myself, my dick getting hard inside the pussy panty. I'd almost forgotten the man whose apartment I was in until I saw his reflection in that mirror. Leonard was leaning against the hallway wall, looking at me. I turned and faced him, arms akimbo, legs spread.

"Well, big, boy," I taunted him, "See something you want?"

Leonard came over and kissed me, then turned me to the wall. The panty had an opening in the back so that I could relieve myself without removing it. He spread my legs, and I reflexively braced my hands against the wall, sticking my ass out for what I knew was coming—or cumming. Leonard didn't disappoint; he speared me instantly, working his tool in and out of me for several minutes before having another dry cum. He just pressed himself against me and let his cock twitch inside of me. I enjoyed the feel of his chest on my back, his lips nibbling my neck and ears, but I missed the feel of his pubic area on my skin, or his kissing my lips while he was in me. I resolved not to let him fuck me this way again.

He pulled out and turned me around again, pressing my back to the wall as he kissed me. I reached between us to grab his half-flaccid dick and rub it against my ersatz vagina. He quickly pulled back, pinning my shoulders to the wall, his dick deflating in my hand.

"If I wanted a woman, I'd be with one now," he hissed. "I know what I am, Valerie, and what you are. If you need that," he looked down at my pussy, "then go ahead and wear it. But don't expect me to use it." He then pulled away and finished undressing.

I stood there watching as he took off his clothing, not certain what to do. I liked being a woman. I liked having breasts. I liked having a cunt. And I wanted a man to fuck it! For the first time that weekend I thought about who my next lover would be. Not that I wouldn't give Leonard my ass or my mouth anytime he asked for them, but I wanted a man to fuck my cunt, even if it was a phony one. I continued to look at myself in the mirror as Leonard took a shower. One thing I had to agree with him about: I was definitely hot! If I could get a rise out of all those cocks at the club house, then maybe one of those cocks would want to cum in my new pussy.

I showered as Leonard finished dressing, leaving the pussy panty on to test its water-tightness. Well, no. I wanted to wash my pussy—to finger it, to run suds through it, to rinse it with the spray. I envied Naomi—all women—who were able to orgasm this way. I wanted to be them. I enjoyed washing my breasts too. Taking the sponge and squeezing the suds over them, and watching the bubbles run down my body into my pussy. Yeah, I love being a woman!

I enjoyed drying myself too. It was like taking a dry shower with the towel replacing the water. As I ran the towel over the cunt hairs I envied Naomi and other women for being able to arouse themselves so easily. When I was finishing I looked toward the bedroom to see Leonard on the bed watching me. His face was a mixture of lust and disgust. He wanted me as a sissy, but not as a woman. And as much as I wanted to be his sissy, I wanted to be his woman more. And if not his, then someone's.

He began getting dressed as I finished drying myself. Leonard was noticeably cooler toward me. He had made reservations at Les Cygnes de Loire–the fanciest–and most expensive—restaurant in town. I decided that I should dress as conservatively as possible, while still being stylish. Naomi had selected by best dinner dress—a black number with a tight bodice, a flared skirt that went to mid-calf, with a black mesh yoke and mesh full length sleeves. Again, I regretted that the first time I would wear this dress would be on a date with someone other than her. I accessorized the dress with a single strand pearl necklace—real pearls—and a pair of pearl earrings—two-three-two pearl rows dangling—black suede 3-1/2" heels with matching clutch purse. The heels also had matching suede gloves, but Naomi had not packed them, this being summer. I had replaced the pussy panty with a padded long-leg panty so that the skirt of the dress would sway sensuously as I walked. I also decided to get a full body suit with breasts and hips and ass—and cunt!

When I was fully dressed and had completed my make-up, even Leonard had to be pleased: he was. "You look beautiful," he gushed as he opened the door for me. We drove to the restaurant in silence. I could tell from the way the restaurant went quiet when we entered that I had indeed made an impression that afternoon. Several of the patrons were special ladies like myself, including Marlena Schwartzmann, who was with Tom Hanratty, and the Tatnalls, another couple who I knew included a sissy husband, but who were not part of the St. Clair circle. Of the men in the room, both those who were members of THE ESTATE and knew of my special status, and those I assumed thought I was a real woman, pure lust rode their faces! I was thrilled! Whether real woman or special lady, I was the belle of the restaurant!

Despite his earlier pique, Leonard too was pleased. What he had wanted was happening. He was squiring around an extremely attractive woman whom every man in the place lusted for, and envied him for having. It made no difference that I was a special lady. To those who knew, it made them want me as such. And envious of Leonard for the same reason. For those who did not know, they felt the same.




St. Clair Ladies Circle: Leonard Pt. 2



Every now and then one of our mutual clients would stop by the table to say hello. Our male mutual clients. After the meal, I went to the ladies' room to freshen my make-up. There were nine other women inside.

"I hope you're proud of yourself, young woman!" the most elderly of them huffed at me. "all my George has been hinting at all day is having me do that disgusting thing you did out at the golf course. I told him to find himself a prostitute!" She then stormed out of the restroom, followed by her entourage, four women young enough to be her daughters.

"I hope you're proud of yourself, too," a voice came from behind me. I looked in the mirror at a woman who was also a special lady, passable, but obviously male to those of us in the know. "I never thought of doing that at the golf course, with Leonard or anyone else." My raised eyebrows signaled my surprise and my confusion. She stepped toward me and extended her hand. "Irene Carruthers."

I shook her hand, "Valerie Imhof."

"Oh yes," she smiled. " Imhof Consultants." Again the surprise must have registered on my face. "We," she indicated the three others still in the room, "know about you and your wife. And about the St. Clairs. Probably more than you do." Tittering. "Much more." More tittering. "All of us have dated Mr. Hopkins. Some still do."

I looked around at the four knowing faces. Only on close scrutiny could one detect any maleness in their appearances. Their demeanor and dress, and their presence at Les Cygnes de Loire all indicated that they were the type of special lady that appealed to Leonard. While I had been jealous just twenty-four hours ago about Thelma and Antoinette, now I accepted that I was but one of a procession of special ladies in Mr. Hopkins' life, and that he was but the beginning of a procession of men in mine. I smiled wanly at them all. They smiled graciously back. No cat fight here.

"He's really a great date," Irene continued. "Good looking, a great conversationalist, informed and informative, likes fine restaurants, discreet—and a great fuck! He makes what being a woman is all about. Personally, I prefer to being a top—banging some sweet young thing..." She looked at the quartet, who smiled demurely back at her. "rather than being fucked. But even us tops need to feel like a woman every now and then. Being complimented on our looks. Being taken to dinner. Being courted. And seduced. Knowing that the man you're with can't wait to get your mouth on his cock and then his cock in your ass. And you barely able to wait for him to be in either place! Yesss!" Irene hissed, her eyes now closed. When she opened them, they were wet. She quickly dabbed them dry, then turned to the mirror to repair her mascara.

As she was doing so, several other women walked in. All stared daggers at me. Irene watched them in the mirror, then turned to me. "I own Irene's. I don't believe I've ever seen you or your ..." She stopped and looked at the women who had just entered, then returned to me. "Your partner at my shop. The two of you must come in some time. I don't have the same inventory Marlena Schwartzmann has, but I'm sure what I have will please the two of you." She smiled at her double entendre. Without waiting for my response, she turned and whisked out of the lavatory, followed by her court. I finished my business and joined Leonard at our table.

"You were in there a long time."

"Well, you know how we ladies are."

"I gather you had a talk with Irene."

I looked at him, somewhat surprised that he would bring up another of his lovers, especially in this context. As I looked at him I realized he was quite nervous. And worried.

"Well, Mr. Hopkins, you've been tomcatting around with us special ladies for quite some time now. You should realize we'll run into each other and exchange notes. I mean, after all, it's what you men do." I resisted adding I should know.

"And what notes did you and Irene exchange?"

"Only that I'm but your latest conquest. And that Irene and her entourage were your earlier ones." Leonard looked uneasy. "And that you're a great date...and a great fuck! I have to agree with the last two observations."

Leonard shifted uneasily. "Anything else?"

"No. But I think you'll be hearing from her soon."

Leonard pursed his lips, his discomfiture more and more evident. A steady stream of men visited Irene's table, each waiting for the man before him to leave before presenting himself. Most of them I recognized as being members of THE ESTATE, about a third of them my clients. From their demeanor I knew that something more than checking out Irene and her friends was going on, but I did not know what.

"Who is that woman?" I asked, indicating the old bag who had verbally attacked me in the women's room.

Leonard looked in the direction I indicated, then let out a low whistle. "Where'd you meet her?"

"She was most unpleasant in the loo," I responded.

Leonard shook his head. "That, my dear, is Mrs. Ophelia Hepplewhite Natcher" Leonard said in awe.

"Natcher as in Natcher County?" I asked, stating the name of our county.

Leonard nodded, adding "and Hepplewhite as in Heppleton, the name of our illustrious little burg."

Now it was my turn to be in awe. Talk about grande dames! I looked over at her again. She was easily in her sixties, probably her seventies. That would have made her a great-granddaughter, maybe only a granddaughter, of the founders of this town and one of the first settlers of this county. Talk about first families!

"Do you think she knows?" I queried.

"Nooo," Leonard said slowly. "She is one of the few people in this county who could have us all arrested for perversion and destroying the public morals. Even THE ESTATE would not be able to counter her. No, she's old money—and old values—and old everything. She would not understand you—or me for that matter. In fact, I don't think she knows about her grandchildren and great-grandchildren, several of whom are members of THE ESTATE. In fact, it was the younger Natchers and Hepplewhites who paved the way for THE ESTATE's take over of Heppleton and Natcher County."

Leonard indicated the other women in Mrs. Natcher's court, and the men with her. Younger Natchers and Hepplewhites? The youngest was in his or her forties. Sitting there they were the picture of Middle American upper class gentility. I wondered what sexual proclivities they had that led them to THE ESTATE?

We left the restaurant, Leonard asking "Exactly what did she say to you?" as we drove to his place.

"She castigated me for what we did at the country club," I replied.

"Well, Val, I didn't expect our tryst to reach so high in this town. The next few weeks might be a little strained for both of us."

We rode the rest of the way in silence. At his place, I waited for him to open the car door and help me out, then we walked arms around each other to his apartment. After entering, Leonard closed the door and spun me around, taking me in his arms and kissed me ardently.

"I really wanted you to know how much I've enjoyed your being with me this weekend," he said when we broke for air.

"I enjoyed it too, Leonard," I replied, placing my arms around his neck and kissing him deeply. 

When we broke this time, we turned and went into the bedroom. Words were no longer needed. Silently we undressed, me turning to let him unfastened the back of my dress, then letting it and all my other garments pool at my feet. When I turned around, Leonard was naked, his cock rampant. I sat on the bed as he positioned himself before me. I took his cock in my right hand and brought it to my lips, kissing the slit gently. As I opened my mouth to receive him I slid my left hand underneath his balls, running my nails along his perineum. Familiar now with his dick, I slip the head through my lips until I again engulfed it fully. Gently sucking, running my tongue around it, scratching his perineum, palming his sac, it wasn't long before Leonard was ready to cum.

I released him and took a condom from the nightstand, kissing each inch of his shaft just before I slid the latex coat over it. Cloaked, I moved into position on the bed as he lubed himself. He climbed between my legs and inserted a copious amount of lube into me as I held my legs up and splayed. Leaning forward, he didn't have to tell me to take a deep breath as our lips met. I wanted to inhale him into my very being! As we kissed land his tongue invaded my mouth, his cock invaded my body. I was his mare and he was my stallion, posting on me as we gamboled on the silken pasture of his bed. When he came, I gladly received him, a woman giving pleasure to her man!

-000-



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 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 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 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.