Judy

This story is the continuation of the story "Denise" (www.literotica.com/s/denise-11) published on Literotica on 07/02/2023.

"I've already called Judy," my wife, Carole, told me.

It was nearing noon on Saturday and Carole was preparing to join Denise at her house for a surprise party for Jason, Denise's husband. Jason was due home from a weeklong business trip this afternoon. The four of us had become intimate friends, with benefits, over the past months and the women's plan for Jason was partially a consequence of a similar party I had with them while Jason was traveling. The other reason for the planned party with Jason was because they wanted to.

Judy is my administrative assistant at work. She's a sexy broad about ten years older than we are. Recently, she's been demonstrative in her sexiness and she's been hinting at something outside of work, and inside of her, with me. I think she somehow figured out my extracurricular activities with Denise and Carole and wants to be part of it. Carole agrees and is flattered that another woman wants her husband in bed.

So, Carole is planning an overnight debauchery with Denise and Jason and is concerned about my welfare while she is gone. Obviously, she thinks Judy is my administrative assistant, my work wife and my welfare manager.

"When did you call Judy?" I asked.

"Thursday, after we talked," Carole answered. "I didn't want to wait too long in case she wasn't available."

Amazing. Once again she's way ahead of me. I never had a clue. "And she's available?" I asked.

"Available, locked and loaded," described Carole. "She should be here about two."

"And you'll be?" I asked.

"Gone," said Carole.

"Isn't this going to be a problem?" I asked. "It creates an unsymmetrical situation."

"You'll have to explain that."

"Well, if this happens, I'll be having sex with you, Denise and now Judy. You'll be limited to me and Jason. That seems unfair somehow," I explained.

"Your math is incomplete," said Carole. "I agree it's unbalanced but in my favor. True, I have you and Jason but I also have Denise and now, possibly Judy. That's three for you and four for me."

I couldn't dispute her logic. I'd seen her and Denise in action and I could only imagine adding Judy to the mix.

"Thanks for thinking about me," I said.

"You're welcome," she said.

"Do you want to fuck before you leave?" I asked.

"I don't know if I have time," Carole pondered the question.

"It would be good for both of us as a reminder of who we really care about," I reasoned.

"Try not to make too much of a mess," Carole said. "I don't want to have to shower again.

She took another shower and left for Denise and Jason's place just before one and without an overnight bag.

If Carole was correct, I had about an hour to prepare. I didn't know what to prepare for. All I had was a number of potent hints from Judy like sitting in front of me claiming she had removed her panties, a claim I was unable to visually confirm. Her comment about a "hair of the dog" treatment for my sexual hangover rang again in my ears and the view of her panties hanging out of her desk drawer only added to my confusion.

I took a shower, dressed conservatively and sat barefoot in the living room with a glass of water. I tried to imagine Judy's body. Except for last Thursday, she rarely wore clothing that featured her feminine attributes. Over the years, I'd concluded that her breasts were large. How large and how firm was beyond my observational skills. I also didn't have a clue about the state of her pussy.

I focused on what I did know about her. She usually wore her medium brown hair long, reaching to her shoulders and framing her face. Her face was slightly ovoid with her jaw line slightly narrower than her forehead. On days when she wore her hair up, I could study her ears that were close to her head with suckable lobes that were always adorned with diamond studs.

Her eyebrow color matched her hair color and, except for trimming and plucking, was natural without any attempt to change their shape with unnecessary makeup. She rarely wore makeup, using it sparingly with a natural-colored lipstick. Her lips were naturally shaped without the need for fillers to enhance their beauty. I imagined kissing those lips or watching them wrapped around my erection.

Finally, her nose. Her nose was a classic celestial nose with a slightly upturned tip that I wanted to kiss.

I was starting to think about her legs when the doorbell rang. I put my glass of water on a nearby table and headed for the door. Opening the door, I was greeted by a goddess. I had to look twice to confirm it was Judy. With seemingly no effort she had managed to improve her already fantastic appearance by an order of magnitude. She had a broad smile that begged to be kissed and her hair was up in a French braid leaving her ears exposed. Her ear lobes were without the diamond studs which, somehow, improved my longing to suck on them.

She was dressed in a white, high collared, long sleeved Edwardian blouse buttoned all the way up on her neck and covered with a teal, hip length vest left open. Her below the knee skirt matched the color of her vest that fit around her hips and flared slightly.

She was holding a medium sized brown grocery bag in her left arm. Words were difficult.

"Hi Mark," Judy said. "Expecting me?"

I couldn't answer. I just held the door open for her. She walked into the room with a womanly motion that I'd never seen at work. "Are you all right?" she asked.

"I'm fine," I managed to whisper. "I just wasn't expecting..."

"Me?" asked Judy.

"No. I knew you were coming by."

"Then what?" asked a confused Judy.

"You look fantastic," I told her.

"Thank you," Judy said.

"It's just how you're dressed," I said.

"Oh," Judy uttered as she understood my reaction. "What were you expecting? Jeans and a sweatshirt?"

"No, but not quite what you're wearing," I confessed.

"Should I take it off?" asked Judy.

"Not yet," I grinned. "What's in the bag?"

"Lunch," Judy told me. "Some Thai takeout."

"I like the way you think," I said and led her into the kitchen.

We sat in the kitchen and shared Pad Thai with prawns, bean sprouts and peanuts. There were even quarter slices of lime in a separate container and jasmine rise. She had included coconut rice custard for dessert. I put dishes and silverware on the table. I pulled a bottle of Pinot Grigio from the fridge, added wine glasses and we sat down to eat.

We ate silently. I was pondering the reason Judy was eating lunch at my kitchen table and wondering how things were going to develop. Starting seemed to be the most imposing. I also wondered if Judy was thinking the same thing.

Sated, I pushed the dishes aside and filled our wine glasses with the last of the wine. We sat, looking at each other for several seconds before Judy leaned forward and extended her hands. I took her hands in mine and waited.

"Mark," Judy started. "I came here today with a single thought. I don't need to tell you what it is. I've fantasized about it for years but Carole's phone call Thursday night suddenly made it real."

I started to say something. "Let me finish," Judy said.

"Now that I'm here, alone with you, on the verge of making my fantasies come true, I've suddenly lost my nerve. I've never done anything like this in my life and, frankly, I'm scared."

I squeezed her hands. "Do I frighten you?"

"No. I frighten myself. I'm frozen by self doubt. Will you like my body? Will I know what to do and when? Will you be disappointed?"

I held her hands between mine. "Judy," I said. "Trust me. Trust yourself. There are no expectations. There is no right or wrong. Leave your thoughts behind. Trust your body. It knows exactly what to do and when to do it. It knows what it wants and how to get it. At the end of the day there are only fantastic feelings and better memories."

"I think I can do that," Judy committed.

I leaned over the table, raised her hands and kissed her fingers. She closed her eyes and I could feel her arms relax. I turned her hands over and kissed the palm of each hand. She exhaled. I kissed her palms again and touched my tongue to the tips of her fingers. I felt her quiver.

"Let's move inside," I whispered.

We stood up, I handed Judy her wine glass and we walked, hand in hand into the living room. I led her to an overstuffed chair. I sat down and guided her to my lap. We sat with my right arm around her waist. I took a sip of my wine and offered my glass to her lips. I tilted the glass and she took a sip. Then she offered her glass to me. I sipped and ran my tongue around my lips.

I handed her my wine glass and she took it in her free hand. I touched her chin with my left hand and gently pulled her face closer to mine. When she was close enough, I closed the distance and kissed her softly.

Her eyes opened wide and then closed. She returned my kiss with a kiss of her own. I was right about her body knowing what to do. Her kiss was electric and my body began to react. A few seconds into the kiss, Judy began to wave her arms around. I looked up. "Take these damn glasses," she said.

I put the wine glasses on a nearby table and we resumed kissing, this time with Judy's arms wrapped around my neck. Whoever taught her how to kiss had my appreciation. I needed find him some day and thank him.

The kiss had the expected effect on me. My erection was rising in my pants and becoming uncomfortable confined as it was. Judy had to notice. When her mouth opened, she began to squirm on my lap. Whether to ease my discomfort or improve her position I wasn't sure but it only encouraged me.

Our tongues caressed each other and probed to explore behind each other's teeth. Judy took my left hand and placed it on her right breast. I fondled her breast and we sucked on each other's tongues until we had to breathe. I took advantage of the sudden freedom to tilt her head and kiss her earlobe. When I sucked her earlobe between my lips and tickled it with my tongue, she pushed her head against my lips.

When I paused, she turned her head and said, "Mark, let me up for a second."

Judy stood up in front of me and took off her vest. "This is only in the way," she commented.

The way her blouse flowed over her breasts was mesmerizing. She pulled the blouse from the waist of her skirt and started to unbutton it.

"Let me do that," I said.

She stopped and looked at me. "That would be wonderful," she admitted.

I put my knees together and moved her to sit on my lap again. She hiked up her skirt and sat, straddling my knees, facing me. I looked into her eyes and slowly began to unbutton her blouse from the neck down. There were a half dozen buttons on the neck of her blouse alone and, as I undid each one, her smile broadened. The buttons grew further apart as I continued down the front of her blouse.

Her eyes closed, her back arched and she pushed her chest in my direction as I reached the last button and her blouse fell open, hanging on the tips of her white lace bra. Judy held up her arms so I could unbutton the cuffs of each sleeve of her blouse. I lifted the blouse carefully from her breasts and slid it off her arms. It landed on the floor somewhere behind her.

Her breasts weren't large. They were immense, barely contained in her substantial bra. She waited patiently with her back arched and her chest extended. I realized she wanted me to take the next step. I put my arms around her body and settled my fingers on the five hooks of her bra. One by one, I unhooked each clasp. The last one was the most difficult. It was the only thing holding her bra in place and it had become tighter under the strain. I tried several approaches and finally just pulled it apart. I might have damaged the bra but my frustration and anticipation overcame my common sense.

Her bra fell into the space between us. Her breasts were magnificent. They were large but they didn't look out of place on her broad chest. They were perfect spheres that hung from broad bases. They didn't sag. They hung several inches down on her chest due entirely to their size. Her large brown nipples were plateaus high on each breast with almost no areolae.

I couldn't resist. I reached out, held her left breast in one hand and kissed her nipple. Her body shivered with the contact and did it again when I kissed her right nipple.

"You like?" Judy asked.

"I love," I admitted. "Your breasts are incredible."

"Thank you," she said.

"You're welcome," I responded.

The sight of her breasts and her weight on my legs was strongly influencing my penile response. My erection was obvious to anyone looking at my crotch and Judy was looking. "You look uncomfortable," she commented. "Let me help," she added as she reached for my belt and fly zipper. She managed to pry open my trousers and briefs enough so that she could pull my erection into the open.

When she wrapped her fingers around my shaft I almost came. Why I didn't is still a mystery. "Your cock is incredible," she said.

"Thank you," I responded.

"You're welcome," she said. "I need to improve this situation," she added.

"She stood up and, with help from me, pulled my pants and briefs down my legs to my calves. "That's better," she observed.

She pulled up her skirt, put her hands underneath and pulled off her panties. She stepped out of them, lifted her skirt again and sat back on my legs facing me. "That's much better," she said.

Judy leaned forward and kissed me again. She put her arms around my neck and slid forward on my legs until I could feel the heat of her passion in between my thighs. She reached down with one hand, pushed my erection flat between my legs and pinned it down with the lips between her hips. Her labia wrapped around my erection and she began to slide back and forth on it while kissing me even more fervently.

She was incredibly slippery. The heat was as intense as her passion. I could feel her throbbing pulse in the flesh of her labia. She lengthened each stroke until I felt the opening of her vagina catching on the head on my cock with each one. She tried unsuccessfully to find the right position to complete our union. I reached down and stood my erection vertically. She shifted her hips back, up and then down, completely engulfing my erection inside her.

We both sighed as she settled down on me. I was immediately on the verge of an embarrassing premature release if she moved. Fortunately, she didn't move. Instead, she put her head over my shoulder, pulled us closer together until her breasts were squashed against my chest and just absorbed the feeling of me inside her.

I was completely in agreement with her. The feeling of being inside her was exquisite and I needed to process it as much as she did. Eventually, I moved within her. "Don't," she said in my ear. "I'm not ready for that yet."

I didn't move. Instead, I kissed her neck and nibbled her earlobe. She moved. "Judy," I said. "I'm going to have a problem if you move and I shouldn't have that problem while still inside you."

"Why?" she asked.

"In my experience," I explained. "When a man and a woman connect passionately like we are at this moment, desirable interior orgasms can have undesirable consequences."

"You mean I could get pregnant?" Judy asked.

"That's the simple description," I suggested.

"Well," suggested Judy. "Have a go at it. Pregnancy is not an option with me." She proceeded to move aggressively on me.

I lasted less than five seconds. I grabbed her hips and pushed up against her as hard as I could. My erection swelled inside her and my orgasm left me breathless. Her orgasm started before mine finished. Her body tensed and then went limp as her body collapsed against mine.

Neither of us moved for several minutes. My erection deflated inside her and, when she moved, fell out of her followed by a flood of mixed fluids. Judy squirmed on my lap, leaned back and kissed me. "Thank you," she said.

"I should be thanking you," I responded.

"That was incredible," Judy declared. "Much better than I expected.

"I didn't know what to expect," I admitted. "But you've created a monster."

"A monster?" she asked.

"Yeah. A monster. A monster that wants more of what just happened," I explained.

Judy laughed. "That makes us 'Monsters, Inc.'" she agreed. "But we need to improve the environment."

"I know just the place," I said. I moved her off my lap, kicked off my pants and shorts, stood up next to her and started for the bedroom. We made quite a sight as we walked hand in hand to the bedroom, Judy topless and me pantiless,

"This is really nice," commented Judy as we entered the bedroom. "But first I have to pee."

She went into the bathroom, left the door open and peed. I took off my shirt while I waited. Judy came out of the bathroom without her skirt. I looked at the complete woman in front of me, focused on the perfect triangle of pubic hair that I'd just been on the inside of without seeing it.

"Is this okay?" Judy asked.

"That's perfect," I told her.

She began to turn around slowly so I could appreciate the rest of her assets. She smiled as she faced me again. "You know, Mark," she said. "I was nervous about being naked in front of you but this feels natural and easier than I feared." To prove it, she turned around a second time.

She looked behind me at the neatly made king sized bed. She walked around to the far side and grabbed the top of the bedspread. "Help me out here," she said.

Together, we folded the bed covers down and let them fall on the floor at the foot of the bed. The light weight blanket and top sheet followed. She climbed on the bed. I climbed on the bed and we wiggled toward each other until we could touch and kiss each other.

"Why haven't we done this sooner?" Judy asked.

"Probably because we work together," I suggested.

"Plenty of co-workers have relationships," Judy insisted.

"Not if one of them works for the other," I added. "It's against company policy."

"Only if they get caught or one of them gets pissed off enough to file a complaint. I could name a half dozen women who have improved their respective positions by fucking their bosses," said Judy.

"I don't need to know that," I said. "And I don't have the power to improve your position."

She kissed me. "This is the only position I want," she grinned.

I heard the bell for round two. I returned her kiss and fondled her breasts. I moved until I could kiss her breasts and fondle her lady bits. Judy relaxed and allowed me to explore her body. When I kissed her clitoris, her body reacted reflexively and when I sucked her clitoris between my lips, her back arched. I slid up her body and entered her for the second time, this time slowly.

She absorbed my erection and we began a mutual rhythm. Her legs came up alongside my body with her heels on the bed. Minutes later, she lifted her legs higher and held them up with her hands behind her knees. Her orgasm crested when she pulled her knees against her shoulders.

As her orgasm subsided, she turned us over until she was on her knees. "Get behind me," she ordered.

I entered her from behind. Her body seemed to suck me inside her. Only her cervix prevented me from going further. We resumed our rhythmic fucking. Judy was squeezing my cock with every stroke. "Come on, Mark," she called to me. "Don't hold back. I want to feel your sperm inside me."

I relaxed somewhat and granted her wish before collapsing exhausted on top of her. We lay together in a twisted, sweaty pile until we could breathe easily again. Judy pushed me off her and rolled over to face me. "How do you do that?" she asked.

"Do what?" I replied mystified.