Starting Over – Chapter Four Judy Introduces Jack to Her Club

Prologue

This is the fourth chapter about the sexual rebirth of Jack a senior citizen who learns it’s OK to enjoy sex again after the tragic loss of his bride and lover of 50 plus years. In this chapter, I’ve tried to spend a little more time developing characters and describing their surroundings. I’ve divided the chapter into sections. Those of you who are looking for the hard core sex, may want to skip directly to the “The VIP Room” section.

Thanks to the 40s Couple, Deb and Allen who post their home video’s online for providing encouragement and editing service to me. Also thanks for allowing me to include characters based on what I saw in their videos and what I learned from them in our e-mail exchanges. They are a truly exceptional couple.

As always, I appreciate your constructive criticism. The fact is that I am not a very good proof reader. While I try to find misspellings and errors in punctuation, I’m not always able to catch these errors and I ask for your understanding.

Introduction

Judy continued introducing me to her friends at different events. Each of these introductions proved to be intellectually and sexually stimulating. I guess you might say I was back into the social circuit. One day I got a call from Judy. “It’s time you saw my club. Interested?”

Well, by this time I was interested in anything Judy suggested. “Tell me about your club, Judy.”

Judy explained that the club was originally formed by people who were interested in perfecting their massage techniques. These are the people who put on the class that Judy took to learn the art of massage. You may remember I helped Judy pass her Massage Final Exam. It was a mind blowing, sexually liberating event for both of us.

Judy went on to explain that club membership has expanded to include people who are looking for intense social interactions and also people who just enjoy a formal night out with a good dinner and stimulating conversation. That explanation sounded interesting and just a bit mysterious and intriguing.

Thinking back to Judy’s final exam really raised my interest, and my cock. “When can we see your club?”

Judy told me that the club was having their quarterly dinner meeting next week Friday. “It’s black tie. The bar opens at 6:00 PM and the dinner starts at 7:00. “ She gave me the address and I said I’d pick her up at 6.

When the time arrived I pulled into Judy’s driveway at precisely 6:00 pm. I walked to the door and knocked. After a short pause, Judy opened the door. “Oh my God! Judy, you look fantastic.” Judy had outdone herself. She had a new hairdo. Her hair was piled high on her head, exposing her long sensuous neck. She was wearing a floor length gold dress that draped her body in an almost regal fashion. The dress was metallic and shimmered every time Judy moved. The neck was a low cut scoop that showed off the swell of her breasts. When Judy took a step toward me, I noticed the dress had a side slit that went almost all the way to her waist. Judy has athletically strong toned legs and this displayed them in the very best light. That Judy, what a minx! She could hold the slit closed with one hand and be as modest as a nun. Or she could let it fall open to expose a lot of her body. Then the idea hit me. Judy could not be wearing anything under that wrap. My cock sprang to life. This was going to be a great fucking evening…literally.

“Put your tongue back in your mouth, There will be time for that later, Jack. Now give me your arm and let’s get going.”

Judy’s Club

About 20 minutes later we pulled up at the address Judy gave me. The building was singularly unimpressive. It looked like a four or five story warehouse in a not so nice section of town. “Are you certain this is the right place?” Judy just patted my thigh, dangerously close to my semi-hard cock. She said something about not judging a book by its cover. We were interrupted by the knock on my window. It was a valet attendant. I unlocked the doors and he opened my door while another attendant helped Judy out of her side. I thought the attendant would be embarrassed when Judy spread her legs and gave him a wide open beaver shot, but he just smiled and said, “Hello Judy. Welcome back to Rubbers Anonymous!”

I took Judy by the arm and escorted her to the only door I could see. Another attendant opened the door and we entered a small lobby. There was a small desk with two computers and two people checking in members. “Members ID please?” Judy reached into her purse and produced what looked like a credit card. “And this is Jack. He is my guest, tonight.”

“Welcome to Rubbers Anonymous, Jack, Please sign one of our guest member forms.” I looked over the form. It stated that I was voluntarily requesting admittance to Rubbers Anonymous, and that I was a consenting adult, and finally that I agreed to treat the location of the club and the Identification of the members confidentially, in accordance with the terms of the temporary membership. .

As I read the form, Judy moved behind me and began caressing my neck and down my back to my waist. As my cock began to rise, the Entrance Associate just smiled at me. I’m certain you will enjoy yourselves. With that, I signed the form.

A door behind the desk opened and we moved through it. Wow what a change. Outside the door, we were in this dumpy office. Inside the door, we are in a luxurious reception area.

The reception area makes me think of a fine restaurant. The tables seat 10 or 12 people and are covered in luxurious linen table cloths. The place settings are fine china. The silverware is gold accented sterling. There is a large bar on one wall, and a stage on another wall. There is a long hallway that leads out of the back of the area and a grand staircase . Both of these exits have signs displayed prominently that state, “Platinum Members Only!” The entire area is covered in plus red carpeting.

Judy and I strolled to the bar. I ordered White Zin for Judy and myself. “Judy, what was all that security about for a simple social organization?”

Judy apologized for the tight security. “I need to tell you about the club. We are a private club, for consenting adults. There are four levels of membership: Bronze, Silver, Gold, and Platinum. Bronze level members are guests of Gold or Platinum Members. Silver level members Are sort of athletic club members. Gold level members are voting members who have access to all levels of the club, except the private rooms. The Platinum members have complete access to all club facilities. They can use the private rooms and suites to entertain their personal guests or to relax with other consulting members.

Since there are small minded people in this town who reject the notion of consenting adults, our lawyers advised us to establish stringent membership requirements. We are a private club. What goes on in this building, stays in this building.

Judy’s Friends

Wow, what Judy was telling me was beginning to sink in. This was destined to be a great fucking evening. My solitude was interrupted by Judy’s tug on my shoulder. “There’s Nan. And she has a guest I’ve never seen.” We started moving toward them. Nan practically ran into Judy’s arms. Then she turned to me. As she threw one arm around my neck, her other hand found my cock. She squeezed it through my pants and then patted its length. “So nice to feel you again, Jack. Oh pardon my rudeness. This is Carlos. He’s from Brazil. His English is very limited, but his tongue is fantastic!” Nan laughed at her own play on words. I shook hands with Carlos. His grip was strong and firm. He stood over 6’ foot and looked like he could play wide receiver for any NFL team. He smiled at me, “Boa-noite.”

Nan asked, “Are we at the same table?” Judy reassured her that “Of course we are! It‘s right over here.” We all moved to our table. There were three couples already at the table. Judy seemed to know everyone.

“How’s every one tonight? You know Nan. This is her guest Carlos. Nan tells me that Carlos doesn’t speak much English, but with his tongue he doesn’t need to.“ Everyone laughed. Carlos flashed everyone his brilliant smile and executed a small bow. “This is Jack, my guest tonight.” with that I extended my hand as Judy continued, “Jack and Carlos, meet Bill and Barbara, Jim and Sandy, and Deb and Allen.”
Everyone was tastefully dressed in their finest outfits. The men were all in tuxes. The women were wearing floor length formal dresses that showed a lot of skin. As I said hello, I shook hands with each of the men. I nodded to each of the women as I looked each in the eye. They each smiled at me and delicately returned my greeting. As I gazed into Deb’s eyes, she licked her lips seductively, and took my hand firmly.

“It’s so nice to finally meet you, Jack. Judy has told me so much about you. I’m hoping to see more of you tonight.” Wow! Was it my imagination or was the sexual tension thickening rapidly? Deb gently tugged on my arm as she almost whispered, “Here, Jack, sit next to me.”

Deb has sparkling eyes. I couldn’t bring myself to look away from them. She was wearing a black, toga like dress. I couldn’t see how it was fastened around her body, but it looked like a large piece of fabric that was wrapped around her body, exposing her right shoulder. The end was attached to her left shoulder. It draped her body gracefully. As I studied her form, I realized that the fabric was somewhat transparent. I could see her ample breasts. They sat low on her chest and had very large dark nipples. Deb’s normal movements caused the fabric to slide seductively over her breasts causing her nipples to become erect. Deb saw my look of lust and just smiled. She picked up her clutch purse and casually dropped it on the floor. “Oh Jack, I’m so clumsy!” Before I realized what was happening, Deb leaned forward to retrieve her purse. This motion allowed the fabric to fall away from her body. I could see her breasts and especially her magnificent nipples. Deb straightened up and looked me right in the eye, “Later lover.” She gave my cock an extra squeeze and turned her attention back to Allen.

Judy explained to me that Deb and Allen are a 50 something couple who are definitely in love and also thoroughly enjoy sex. They love to provide each other with the ultimate in physical pleasure. They also love to watch each other being pleased by additional playmates. You might say they love to watch and be watched. They are also very vocal.

My reaction as I observed Deb and Allen was, “Wow! These two are so in love with each other.” The way they caressed each other, even when engaged in conversation with others, made me think (hope) that they were about to ravish each other.

Dinner was outstanding. The food was delicious and fortunately the portion sizes were not too large. Someone
was thinking. No sense in throwing an orgy and having all the middle aged guys fall asleep after overeating.

Deb spent a large part of the dinner time rubbing her hand along my thigh. She definitely had my attention. “Has Judy explained the membership arrangement to you?” I told Deb that I sort of understood. She told me that she hoped that I would be joining them in their suite for the evening. As she said that, her hand went right to my erect and very hard cock. “I hope that means yes, Jack!”

“I would like that very much, but as Judy’s guest, protocol suggests that I should stay by her side.”

“That’s wonderful! Allen has already asked Judy to join us., after dinner for desert in our suite. So it’s settled!”

The VIP Room

Judy took me by my right arm, and Deb took me by my left arm. The three of us headed up the grand staircase, followed by the rest of our table. Judy leaned her head close to my ear. “Our tradition here is that I get you first, before you get to play with anyone else. I can see you are smitten with Deb. She’s fantastic, and I certain Allen would love to join the two of you.”

Judy directed me to a door and swiped a key card. The door opened. Inside were a number of couches and overstuffed chairs. The center of the room was dominated by the largest bed I’ve ever seen. It was all very plush. Along one was a large flat screen TV.

Judy grabbed my arm and ushered us to one of the five doors on one end of the suite. “Let’s get nice and clean for each other, Jack” Out of the corner of my eye, I saw Deb taking Allen into the room next to ours. The rooms turned out to contain large Jacuzzi tubs. Like everything else at the club, the baths were very Plush! We slipped out of our clothes, while never taking our eyes of one another.. Judy stepped into the tub and began soaping her hands. “Come join me lover.” I stepped into the tub. Judy had taken her soapy hands and lathered up her thighs, her stomach, and her magnificent breasts. My cock bobbed its approval. Judy turned me so my back was toward her. Then she pressed that slippery, soapy, wonderful body against my back. I was in heaven! She reached around me and grabbed my cock with both hands and began to stroke it slowly, sensually.

“Judy, I can’t take much more of this!” Frankly I was on the verge of forgetting about anything or anyone else and just allowing my climax to overtake me. Judy increased her pace.

Then I heard what I can only call a bellow from the room next door. “Oh Deb! OH Deb! Oh Fuck Deb! OH DEB! OOOOOOOOODDDDDDEEEEEEBBBBBBBB!!!!” It was Allen and Deb was obviously making him cum.

“See Jack, it’s OK. You can cum too. There’s plenty of time for you to recover tonight. You can fuck all of us if you want!”

Oh my god! I knew who I wanted to fuck next. I had been infatuated with Deb all night. Judy stepped up her stroking even more. Then as she stroked my hard cock with one hand. She slid the other hand between my ass cheeks. She found my asshole and using the very slippery soap as lube, she deftly slipped her middle finger un my ass. That did it for me. Judy always know how to make me cum, even if I’m trying to hold back. I grabbed the towel rack for support. All this stimulation was too much for me. “Oh fuck Judy! Oh fuck Judy! You are making me cum! My body went tense. I pushed my hips as far forward as I could.

“Give it to me, Lover! Give it to me, Jack!” My cock jumped in Judy’s hand. The first jet was small. The second one was an eruption. I lost count after that. I think I began to mumble something about so good.

The next thing I knew, Judy had eased me down into the warm water. She climbed up on this little shelf that surrounded my head, and lowered her pussy directly to my mouth. Instinctively, I opened my lips and extended my tongue. “That’s it lover. You know what I love.” Judy began to move her clit up and down as I licked her cunt from asshole to clit. She picked her pace. I reached for her ass. She was so wet, so slippery. I rimed her ass hole and then slipped a finger inside.

“Oh Jack, that feels wonderful! Oh yes, lover! Oh fuck yes, Jack! Ohhhhhhhhhhhhhhhhhhhhh I’m ccccccccmmmmmmmmmiiiiinnnnnnnggggggg!!!!”

Judy eased herself off the shelf and slid into the water. She moved next to me and wrapped one arm around my chest. I think we fell asleep.

The next thing I knew, Judy was rinsing us both off. Then she dried us with these gigantic, soft, plush Turkish towels. As she patted and rubbed my body, particularly when she attended to my cock, I began to get another erection. I was ready for another round right there with Judy.

“Easy boy! I promised Deb, I would share you tonight. She is so hot to suck and fuck this beautiful guy. Let’s go see what she’s up to right now.” I wasn’t certain what the protocol was. Should I wrap the towel around my self, or what? Judy grabbed both of our towels and tossed them in the corner. “We are way past to point of being shy. Come on lover, follow me!”

Once back in the main room of the suite, I saw Deb and Allen sitting, naked, on one of the couches. They were caressing each other. No, they were actually petting each other! As we approached, they rolled apart. Allen took Judy by the hand and pulled her into his lap. Deb opened her arms and legs to my view.

Oh fuck, was this really happening to me? Here was the hot, sexy, beautiful, sensual woman I had been lusting after all evening inviting me into her very soul. My cock hardened. Deb is a marvel to perceive. Her breasts are natural. They sit low on her chest. Her belly is flat, with just a bit of pubic hair. Her pussy had flowered open and I could see either her fluids or Allen’s fluids glistening in the subdued light of the suite. Her legs are long and muscular. I can hardly wait to feel them wrapped around me. But with all that sexiness staring me in the face, her most attractive feature is her eyes. They sparkle. They dance. And as she scanned my body from head to toe, I got the feeling she was devouring me. My cock got even harder.

I eased my body down on the couch, covering Deb. We wrapped our arms around each other and began to kiss. Long, slow, sensual French kisses. I loved the feel of her body pressing against mine. But most of all, I was intoxicated by her scent. It was fresh and clean, and hot and sexy all at the same time. For an instant, I didn’t want this experience to end. Then I realized, this was just the appetizer. Deb had more treasurers for me to experience.

I began to kiss my way down her chest. I gently caressed her left breast while I sucked her right nipple as deep into my mouth as I could. I licked one nipple while I tweaked the other between my thumb and forefinger. Deb began to moan. Then she began to giggle. She sounded like a school girl being tickled. As she giggled, her breasts began to jiggle. Wow! in this day and age, there is nothing as sexy as natural breasts. I continued making my way south toward her pussy. One short stop at her belly button and then I began to feel the heat emanating from her wet open sex. I slipped my lips over her clit and gently caressed the rest of her pussy lips with my fingers. I heard a sharp intake of air from Deb. Then she began to moan. “Yes, Yes, Oh Fuck, that’s so good. Oh Jack, oh Jack.YYYYYYeeeeeeeeeeeeesssssssssssssssssssssssssssssssssssssssssss.”

Deb wrapped her legs around my head and pulled me even deeper into her sex. She began to rub her clit on my tongue. Her legs covered my ears so all sound was muffled. I think I heard her giggle. I know I heard her shriek! In between these sounds she continued to moan, “Oh Jack, this is so fucking good. Don’t stop, oh don’t stop, don’t you dare stop. I am so fucking close. I’m going to cum. Oh yes here it is! I’m cumming. I’m cumming. It‘s so good!!!”

I could feel Deb throwing her head from side to side. Her legs relaxed and fell to her side. She pounded the cushions with her fists. I took this opportunity to climb on top of her. I held her in my arms. I could feel her entire body shaking with her climax. I positioned my cock at the entrance to her sex. It was wet and slippery. I used her fluids to lubricate my cock. Then I pushed my hips forward. That slippery wet warmth surrounded my cock. “Oh fuck , Deb, you feel so good.” I buried my cock balls deep in her pussy. Deb’s body tensed again. She grabbed my ass and forced my cock inside her body even deeper.

“Oh Jack, fuck me hard. I’m cumming again. Yes. Yes! YESSSSSSSS!” Deb tightened her hold on my ass. Then she slid her arms around my torso. Oh fuck, this woman was strong!

I began to fuck her with long fast strokes. I increased my pace as I felt her pussy contract around my cock. It’s a good thing I already came once with Judy. I knew I could keep up this torrid pace without cumming…at least for a while.

I kept up the pace until I finally felt Deb relax her grip. Then I suddenly pulled my cock clear of her body.

“Oh Jack, don’t go. I want to feel your cock inside me!” I flipped Deb onto her hands and knees, spread her legs, and positioned my cock at her pussy. With one push, I buried my cock balls deep in her sex. “Oh Yes, Jack. I love it. Make me your bitch. I love to be fucked doggy.” Judy pulled her body almost all the way off my cock. Then she pushed back and buried my cock again in her pussy. That little nymph was fucking me!

I looked up and there was Allen. He had climbed up on the bed and was watching us fuck each other. Judy was behind him. She was reaching around his body and stroking his cock. Her entire body would move forward as she masturbated Allen. Then I realized that Carlos was standing behind Judy, fucking her doggy style. Wow, this was hot.

I reached around Deb and grabbed those magnificent breasts. I leaned forward as I pulled Deb’s back against my chest. I loved the feel of her strong firm torso. this forced my cock to slide against her clit as we fucked harder and faster. Oh fuck, I won’t be able to take much more of this. I could begin to feel the approach of my own climax.

Deb looked at Allen. “Oh baby, I want to feel your cum in my mouth. Give it to me. Shoot your load in my mouth. She managed to crawl forward far enough to burry Allen’s cock in her mouth. Judy wrapped her arms around Allen’s body and hung on as he began to thrust his cock

“Oh Deb!” Allen began to bellow. “Oh Deb, I love you so much. I’m going to shoot. Here it cummmmmmmmmssssssssssssss, Deb!” He raised his face as to thank heaven for the overwhelming pleasure he was experiencing. And he buried his cock deep down Deb’s throat.

Deb pulled back slightly. I couldn’t see what she was doing, but I think she was licking his cock clean of his seed. Then in a flash, Deb pulled herself off my cock and whipped her body around to face me. With one lurch, Deb swallowed my cock, balls deep. I could feel her tongue licking my shaft. Instinctively, I began to fuck her warm wet mouth.

I heard Judy moan as she began to climax. That did it for me too. The first spurt from my cock went down Deb’s throat. I fell backwards on the bed. As my cock slipped out of her mouth, the next spurt landed on her chin. Then another fell on those magnificent breasts. I saw Allen gently lower Deb to the bed. He began to lick my cum off her body. Allen wrapped Deb’s quivering body in his arms. Oh those two are so much in love. They care so much for and about each other. I’ve never known another couple who could be so caring and at the same time able to share their partner physically with other lovers. Wow, they are extraordinary people!

I felt Anne’s warmth envelope my body. She cuddled me in her arms like a mother holds a child. Someone covered the four of us with a warm plush blanket. That feels so nice. I always get cold after I cum. No! Wait! Annie’s dead. This must be Judy. I’m so confused. Oh well, I will figure this out later.

As sleep began to overtake me, a number of thoughts and feelings went through my mind. One was total and complete physical exhaustion. Another was an equally powerful sense of satisfaction. I was so content. I was at peace with my life. Thank you Allen. Thank you Deb. Thank you Judy. Thank you Annie! I love you all. I am such a lucky guy to have you all in my life.

The End.

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