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 Leonardis the full title of this submission. The title in Literotica meets its requirements, which do not permit long titles. This is the sequel toThe 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 ESTATEis 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 ownedLily 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 ofLily Marlene'sdesigning. 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 wasCévennes, 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 saidlady. He nodded in my direction when he said it, but otherwise his attention was on his tip: Leonard Hopkins.

"Why don't we start withsoupe 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.