St. Clair Ladies Circle: Leonard
Keywords: St., Clair, Leonard, Ladies, Circle:,
1 2 3 Next
Thelma and I were lunching at one of the St. Clairs' favorite restaurants, having just left the beauty salon. It had been three months since I had been with William. I still could not perform with Naomi as a man, although I ate her daily to orgasms. We had adjusted to our new lifestyle, opening a manufacturers' representative firm, Imhof Consultants, in a different city than the one in which we had lived. This had been my old line of work, with Naomi acting as my secretary, office manager, appointment setter and girl Friday. It was only natural to continue this line of work, now with Naomi the full partner she had always been. To our clients who were also members of THE ESTATE, which were most of our clients, they knew we were a couple with a transgendered husband. To our other clients, we were two women entrepreneurs, probably lesbian. Both willingly gave us the chance to prove ourselves. Members or not, we had to show that we were competent and capable salespeople willing to go the extra mile to represent their product lines. We satisfied both.
By now I had let my dark auburn hair grow down to my shoulders. My lipstick color was a medium dark red—what cosmetics companies like to call by some wine, like Sangria or Burgundy or Merlot. The color contrasted nicely with the slightly ruddy foundation and blush that are now my colors. As this was a Saturday, I was wearing a casual outfit: tunic, skirt, lingerie, two-inch heels. There were two businesses in our town owned by ESTATE members which specialized in clothing for us special ladies. Both carried a special line of shapewear with padded busts, hips and rear ends, depending on the desires of the customer. I always wear a longline bra or bodyshaper or similar garment which smoothed my body shape from upper chest to hips, and let me wear breast forms. Sometimes I wear shapewear which added padding for my ass and hips as well. I always wear stockings, never pantyhose. I just love the tug of the stockings against the garters when I walk, or stand up. Keeps reminding me that I am now a woman.
I normally spent Saturday with one of the ladies, usually Thelma or Antoinette. We did normal middle-class women's things: getting our hair done, or make-overs, or manicures and pedicures, shopping, gossiping. I found out that several of the businesses in our new town were owned and operated by members of THE ESTATE, and catering to us special ladies was never a problem. We were sitting on the outdoor patio of the restaurant with a good view of the area, having coffee and talking about nothing in particular.
"Hello, Thelma," a man said as he pulled up a chair to our table. He leaned over her and kissed her fully before sitting down. He was about my height without heels, trim, with sandy brown hair and hazel eyes. He immediately stared at me.
"Are you the Valerie I've heard so much about?"
I nearly choked on the food in my mouth, and could only nod my head. Thelma, fixing her lipstick, answered for me. "Yes. This is Valerie. Valerie, this is Leonard Hopkins. Lenny, Valerie Imhof."
Leonard took my hand and kissed it. "It's a pleasure to meet you, after all I've heard, Valerie."
I looked at Thelma, quizzically. She finished reapplying her lipstick and looked at me nonchalantly. "Leonard has a weakness for ladies like us, Valerie. Ever since he heard we added a new member to our circle he's been dying to meet you."
"And you're everything they said you were, Ms. Imhof," he added.
I said nothing, trying hard to maintain my composure. I was sure his being here was not happenstance. I swallowed my food and muttered a "Thank you, Mr. Hopkins."
He looked at Thelma with mock disapproval. "Don't tell me, Thelma, that you've never discussed me with this beautiful lady."
Thelma slowly chewed the bite she had just taken. After swallowing, she looked Leonard in the eyes. "You know we always allow new ladies to take some time to adjust after being with William. We wanted to make sure Valerie was ready to continue her life as a complete woman before introducing her to you, or to others."
I was not sure what that meant, or who the "We" she kept mentioning were. Did it include just her and Helga? All the ladies and wives of the St. Clair circle? Naomi? Thelma returned her gaze to Leonard.
"I think Valerie needs a little more time, Lenny. Can I help you?"
Lenny's face alternately clouded then brightened. "Yes ... yes ... certainly..."
The two stood, Lenny placing his arm around Thelma's waist. She turned to me, "Please pay the bill, Valerie. I'll treat the next time."
Without waiting from my answer she turned and walked away with Leonard.
* * *
"You didn't exaggerate about her attractiveness," Leonard said as he and Thelma reached his apartment. When do you think she'll be ready?"
"You really know how to flatter a lady, Mr. Hopkins," Thelma said in mock anger. "Here I, a married lady, am about to enter your bachelor apartment to let you have your way with me and all you can think about is another lady."
By now Hopkins had opened the door and ushered Thelma in. He didn't reply as the two quickly crossed the living room and entered his bedroom. Thelma sat on the bed as Hopkins stood in front of her and let her open his pants and fish out his cock. It was hard, its eight inches pointing at her. She pulled him forward and took the head in her mouth, sucking while undoing his belt and the top hook of his pants, then pushing them down. She had to take his cock out of her mouth to push his boxers down also, but as soon as they were at mid-thigh she clamped her lips around his member again, gripping the shaft with one hand while palming his balls with the other.
When she felt he was ready to cum, she released him, stood and kissed him on the mouth, letting him taste himself on her lips and tongue. She stepped away to undress herself as he finished undressing himself. Both naked, they wordlessly climbed onto the bed and made the beast with two backs, Thelma on the bottom.
Leonard Hopkins was a sissy fucker—a man who enjoyed having sex with other men dressed as and living as women. He was not as big as William in either length or girth, and had a more romantic technique than William. For this reason, the St. Clairs preferred him to be a lady's first lover after William. He had fucked all the ladies of the St. Clair circle, and usually enjoyed a weekly tryst with Thelma. They had an established routine and rhythm, and it took only minutes after he was into Thelma that he came. She kept her legs wrapped around him as he pumped his seed into her, squeezing her sphincter to drain him. Their mouths were practically glued to each other the entire time. After nearly fifteen minutes, he pulled out and rolled off her. Thelma immediately reached inside the top drawer of the nightstand and took out a tampon, which she inserted. No use staining the sheets anymore than necessary.
The two lay silently for several minutes before Leonard spoke. "About Valerie ..." Thelma poked her elbow into his ribs, hard, reminding Leonard that it was a man he had just fucked. He winced. "C'mon Thelma," he persisted. "You invited me to the restaurant to check her out. Well, I've checked her out and I want her. You and Helga know her better than me, so tell me when she'll be ready. Same deal: $1,000 if I'm the first after William, regular rates after that."
Leonard took a breath waiting for an answer. When none came, he asked, "By the way, how much is this gonna cost me?"
Thelma poked him again. "Owww!"
"I should charge you double, thinking of another lady when you're fucking me. However, you were unusually randy this time, so consider it a freebie." She decided this wasn't the time to tell him that she and Helga had decided not to charge Leonard for sex anymore. After all, he was providing them with a service as well.
Lenny smiled and rolled on top of Thelma, kissing her. Thelma started to push him off but felt him becoming turgid again. She pulled her legs up until her knees were at the cups of her bra, and felt him pull the tampon out. He's going to have a large laundry bill this week she thought as he slid into her again.
* * *
Naomi looked at me as we ate dinner. Usually after an afternoon with the other ladies, I was quite talkative about where we went, and what we did. This afternoon, however, I had been silent, even pensive, since returning home. We had prepared dinner together, barely speaking.
"Something wrong, honey?" Naomi asked.
I looked up from my plate, staring at the empty space in back of my wife's head. "No ... not really, Naomi." I paused. "Have you and the others made plans concerning me?"
Naomi stopped eating with fork in mid-air. She looked intently at me, the sign of something hidden on her face. "Well, no, honey. Not plans." I looked at her, waiting for the other shoe to fall. "Well, it's been three months, Val. You're no closer to returning to Nicolas now than the day after William fucked you. The other wives think its time you moved on."
"Moved on?"
"Well, yes, honey. That you experience someone other than William."
"And you approve?"
Naomi was now somewhat defensive. "I wouldn't say approve is the right word. It's just that you've become a woman. You look like a woman, you dress like a woman, you act like a woman. Damn it, Val, you even make love to me like a woman! The wives felt that since you've come this far, you should go further."
"And what is going further?"
"That you begin dating men!" There, she'd said it. The final step: her husband Nicolas no longer existed, and the woman he had become should start being a woman sexually as well.
I looked at my wife in disbelief. Despite the events of the past three months, I still thought of ourselves as a monogamous couple. Now she was asking me to step outside the marriage, maybe even dissolve it.
"Are you going to begin dating men?" I asked, afraid of what the answer would be.
"No. I have a husband. She satisfies my needs: financially, socially, emotionally, psychologically .
1 2 3 Next
Keywords: St., Clair, Leonard, Ladies, Circle:,