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 fromLily Marlene'sthese 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 ofLily 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 atLes 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.