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Lifeguard 2: Jill and Frank: Chapter 3

"Her fourth orgasm was totally different as she squirted. She had never squirted before."

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Author's Notes

"Alex (The Lifeguard Series) sets up Jill with Frank"

Chapter 3

7 PM. Frank took an Uber to the restaurant. Atelier was located in a boutique hotel that in itself was a hot place. 

Frank walked in the front door. He was about 5’9” tall, broad-shouldered from wrestling, and maintaining his fitness so even at almost fifty years old, he still looked like an athlete. He didn’t look his age either. His new suit, shirt and cufflinks were an extravagance he hoped would appeal to a certain woman and made him brim with confidence. He looked good, he felt good.

He walked to the restaurant. The Maître d’ asked for his name and once Frank said his name, Phillipe replied, “Mr. Johnson we are so glad to have you dine with us tonight. Alex has already called to say he’d be a few minutes late, but asked that you be seated as champagne is already on the table to be served.”  With that, he was escorted through the restaurant. 

Atelier was a beautiful and understated experience. The tables were not very close together so it lent a certain privacy to each table. Phillipe walked slowly as he was repeatedly being greeted by the diners. He was obviously popular. Frank didn’t mind the slow walk to the table as he saw some really marvelous-looking women, some who even gave Frank an appraising glance. For some reason, Frank liked that.

Finally, they were at the table. There was a step up to a very intimate small table that had four chairs and a crystal vase with a bottle of Dom Perignon on ice. Phillipe pulled Frank’s chair out, handed him his rich linen napkin as he sat down, then deftly reached over, pulled the chilled Dom out of the vase, quickly opened it and poured a glass for him to taste. Frank sniffed the bubbly contents, then slowly sipped the small amount in the glass. He smiled and said, “Phillipe, has there ever been a bad bottle of Dom?” Phillipe poured a glassful and smiled and said, “Alas it does happen ever so often, but not tonight. Cheers!”

Frank then had a chance to survey the room. He realized that this specific table was the place to see and to be seen. The surrounding walls were well padded and obviously intended to soundproof what people were saying inside of the cocoon. Frank was impressed.

He took a few more sips of the Dom or the “YUM” as Frank liked to think of this overrated, pricey and wonderful libation. Once the engineering business was well established his wife and he used to celebrate with a bottle. Frank gave an inaudible gasp as he thought about his wife. But for some reason at this time he didn’t tear up. Instead, he lifted up his glass, looked up and said, “Love you, babe.”

Shortly, Frank noticed a commotion on the floor. Sweeping into the dining floor were the unmistakable profiles of Alex, Caley, and Jill. They were making very slow progress getting to their table as all three were being greeted and hugged and kissed at almost every table they passed. It was almost like they were movie stars. All three of them. They were all strikingly handsome or beautiful depending on your point of view. And as well they seemed to be genuine and genuinely liked. Jill kept looking over at Frank as they made slow progress. She even gave him a small wave. Frank felt an electricity that such a beautiful person even noticed him. He gulped a bit.

Finally, they broke free and went directly to the table. Caley was the first one to greet Frank who had stood up to greet the group. Caley was even taller with her high heels and was beautifully attired in a simple silk dress with a v-shaped neckline. Her hug was tender, her kisses on his cheek divine. Oh, she smelled good. Alex was next and he gave Frank a hearty handshake and then a hug. He was wearing a great-looking suit and simple check shirt. Elegant. 

Lastly was Jill. “God, she is beautiful.” Frank thought. He turned to greet her not knowing exactly if the chemistry from the night before would carry through to the next day. She reached out and pulled him close to her with her head on his chest and he engulfed her with a hug. A few seconds after she pulled back and kissed him on the lips. Not a peck, a full-on, “We’re adults and I like to kiss.” Frank reacted immediately with a huge hardon. He struggled and started to move around so she couldn’t feel it, instead Jill pulled him even tighter. From there he didn’t even try to hide the effect Jill had on him.

Slowly, they pulled apart, Jill holding his hand. He pulled out her chair so she could sit down and he awkwardly got into his seat as his boner was not subsiding.

He looked up and Alex and Caley were watching the entire event. Alex said quietly, “Jill has that effect on some men.”

Caley hit him on the arm and giggled.

Alex turned to Caley and then said, “Don’t do that, you have the same effect!” and he kissed her.

Everyone laughed and Frank’s boner was soon forgotten and everyone moved on to other topics.

A waiter named Jacques arrived and made sure they were all served champagne. He carried on a lively discussion with Alex, Caley, and Jill as they all seemed to know each other. He started to tell them what was available tonight on the menu, when Caley interrupted, “Jacques, please just have Chef serve us what he would like us to have tonight.” She turned to Frank and asked him, “Is that okay with you Frank?” Frank couldn’t imagine anything being better than that and so he agreed wholeheartedly. 

Then Caley added, “Once Chef has chosen what he wants to serve, have the sommelier bring his wine suggestions since that will be so much fun to see how they’ll pair up.”

Jill said quickly, “Oh that will be fun.”

Jacques expressed his pleasure at being able to do this for the table. 

After Jacques left, Alex piped in, “Frank you know a little bit about me but I’m not sure you got to know Caley or Jill all that well, so if I may?”

Frank agreed for him to proceed of course.

“I met Caley the summer after I graduated from high school. I saw her, I instantly fell in love with her and I asked her to marry me shortly after. Caley is a few years older than me so Caley was already headed to law school at Georgetown and now is in practice with her mother representing athletes, models, musicians, artists, rap stars, and other celebrities. I got my Master’s in Computer Science at UVA but spent most of my time in DC with Caley. We took some law courses together. I was focused on the legal side of cyber security and it’s amazing how much our practice overlaps with protecting the brands for people Caley represents. You know how Feldman works for your company, just think if we had an individual whose likeness, ability, and money-making potential are destroyed by bad actors out there. Working with Caley and her mother on protecting those rights has been fascinating.”

“I met Jill when I joined the swimming team as a sixteen-year-old kid. She was so beautiful. Listening to my parents, they said I followed her around like a puppy dog for years. I was always in love with her. I will always be in love with her.”

Just after he said that Caley leaned over and kissed Alex.

Frank was getting a bit nervous about the direction of this conversation when Jill squeezed his hand and looked over at him. He melted at her smile.

“I don’t know if Jill told you, but she is the principal of the large high school I attended. She’s always giving back. She just loves kids, even goofballs like me. Now it looks like she’s going to progress to Superintendent for a larger school system just outside of DC.”

Beautiful, sexy, giving, smart and successful... that totally makes sense Frank is thinking to himself. 

Frank didn’t know what to say. These three obviously had a special relationship. Was it complicated? He didn’t know, but as they talked, the ease with which they shared this, the calmness and love they had for each other was palpable.

Frank cleared his throat and said, “So why are you telling me all of this?”

Jill squeezed his hand again, and as he turned to look at her, she said, “Frank, I fell in love with you last night. I want to have your babies. You have a choice, but I’d prefer it if you marry me. I’ve never been married. I’ve never wanted to get married until now. As much as Alex loves me and I love him, Caley is the right person for him. So I would understand you may not want to get married to me, but I could tell last night, I wanted you.

Frank was shocked. Somehow he kept his composure and looked back at Jill and smiled and added, “Can we wait until after dinner for me to propose? I’m kind of hungry.”

He was a very, very smart man.

Laughs and a round of “cheers” were shared all around. Frank kissed Jill this time, not waiting for her to kiss him. His heart was fully captured.

After that, dinner was a breeze. The food was wonderful. The sommelier choices were perfect. The company at the table was joyful, entertaining, thoughtful and charming.

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Toward the middle of dessert, Caley looked up and shouted, “Mom, Dad!” 

Frank turned to see a beautiful woman approach the table as well as a very good-looking black man.

Frank recognized the man and said to himself, “Derek fucking Ramsey is Caley’s dad. Derek Ramsey!” Frank thought Derek may have been the best athlete he ever saw play basketball. His two NCAA championships, number one drafted into the NBA, taking a low rung team and moving it into the playoffs his first year in the league, winning the NBA championship his second year, then at the beginning of his 3rd year in the NBA was hustling to the ball, as he always did, slid out of bounds, hit some of the chairs and suffered a catastrophic career-ending leg break and muscle-tear. Derek fucking Ramsey. “Wow.”

Alex, Caley and Jill were exchanging hugs and kisses. Frank had stood up as well to greet. Jill grabbed Caley’s mother’s hand and pulled her over to Frank and said, “Frank meet Belle, Caley’s mom.”

Frank offered Belle his hand, she took it and then held it for a second and looked Frank in the eyes. She smiled then pulled Frank into a big hug. She didn’t say anything but the hug was long and satisfying. She seemed reluctant to let go of him. When she did let go, Jill came up and put her arm around Frank and just smiled. Belle gave a laugh and then leaned over and kissed Jill on the lips. It seemed so natural.

Derek came around and this time Belle introduced Frank. They shook hands, and while Derek was six feet six inches tall, much taller than Frank, the shake was truly man-to-man.

Chairs were found for Derek and Belle and a round of after-dinner drinks was produced. The laughter and talk and kidding just continued. Frank joined in as everyone was interested in him and his business and thoughts. He was quickly made comfortable. Jill was holding his hand the entire time. She didn’t seem to want to let go of him.

Finally, she did as she excused herself to go to the bathroom. Frank hated to see her go, but it did give him another chance to marvel at this beautiful woman as she walked away.

The talking continued.

Jill returned. As Frank reached for her hand, Jill placed an item in his hand. He looked down, and saw a room key for the hotel was now in his hand.

He looked at Jill and smiled. Nothing needed to be said.

More talking. Somehow Frank heard he’d been invited to come to the Ramsey’s house the following weekend with Jill, Alex, and Caley. He saw no reason not to say yes. Frank was a very smart man after all.
It got to be around ten PM when Derek and Belle, then Alex and Caley said their goodbyes. A long time was spent with hugs and kisses and general fun and then Jill and Frank were alone.

Jill looked at Frank and said, “I thought they’d never leave.” And as Frank was stifling a laugh she kissed him.

As fast as they could, Frank and Jill left hand-in-hand and headed for the elevator. Frank looked at the number on the room key and matched that with the elevator bank, and headed to the top floor. Jill told him that Derek and Belle keep an apartment here for themselves or for friends coming into town and it was free tonight.

Frank was already hard the entire elevator trip, thankfully nobody was in the elevator with them. Jill was already rubbing his cock through his pants while kissing Frank.

They found the room number and opened the door. Jill spun around and pushed Frank up against the door, kissing him, while unbuckling his belt, and unzipping and pulling his pants down.

Frank wasn't idle either, he had unzipped as much of Jill’s dress as he could reach, deftly undid her bra, and was reaching around to grab her boob as Jill was pulling his cock out.

Jill grasped Frank’s fully engorged penis then gasped. She couldn’t get her hand all the way around his member. She had never felt a penis this big around. It’s not that it wasn’t just long, it was just so big around. She dropped to her knees to see firsthand. It was truly magnificent. While Frank’s penis was very thick at its base, it ended in a beautiful circumcised taper with a small mushroom cap. It was hard, it was straight. She took as much in her mouth as she could. She sucked on it for some time when Frank pulled her up and kissed her mouth. He savored the musky taste on her lips.

“Come on, let’s find a bed and do this right,” he said.

As they moved through this luxurious penthouse apartment they shed the remainder of their clothes. Jill had a magnificent body. Frank was no slouch either.

Naked and giggling they jumped into bed. Jill pushed Frank down, but Frank flipped her easily and said, “Jill, will you marry me and have my babies?”

Jill pulled him to her and replied, “Yes, I will. Let’s start with the making babies part first,” and she kissed him.

Frank got to the end of the bed and pulled Jill’s naked body toward him. While doing this he slid off the end of the bed. Now his face was directly in front of Jill’s already wet vagina. He pushed his tongue straight in. Frank is endowed not only with his penis but also with a long thick tongue. Jill felt her canal fill completely and she came immediately as well. Frank did not relent his pressure in his tongue and somehow managed to engulf Jill’s vagina simultaneously. She came again and again. Her fourth orgasm was totally different as she squirted. She had never squirted an orgasm before. After a couple of more squirts and orgasms and Jill was ready for a break.

Frank sensed this and came onto the bed. He also knew that his size was going to be a problem. 

When Frank met Evelyn he had no sexual experience. With any other woman every time he tried to get something going, the woman would see or feel his cock and react with horror. Evelyn and he were friends before they were lovers. As they were starting to get intimate, Frank told her of his unusual size. Evelyn loved a challenge, and while it took a good number of tries to figure out how to get all of Frank in her, the effort was fun and exciting and ultimately satisfying for both.

Frank also knew that Jill was super lubricated from her orgasms, so he pushed her back onto the bed and aimed his cock for her pussy. Jill didn’t make any negative sounds or moves. She’d had big cocks though not one this big around. She liked challenges too. Frank slowly started entering JIll. Frank moved his beautiful mushroom head and the first three to four inches of his cock easily into Jill. Jill closed her eyes. He said quietly, “Breathe.” She did so. He slowly added an inch into Jill. It hurt now. Frank sensed this, “Breath.” He said again, she did again and again until all of Frank’s fat cock was inside of her. It was intense. It hurt. But not enough to stop and anyway Jill started cumming. She squirted just a little more and that felt good and also added to the lubrication. Frank wasn’t even moving and Jill was cumming. She finally stopped jerking and quivering and shaking.

Finally, she opened her eyes and said to Frank, “Fuck me.” He did. He started out slow and smooth and quickly sped up. Jill kept cumming and cumming. She wrapped her legs around Frank’s ass and then he came in a huge torrent of love and lust.

Frank slowly pulled out exhausted and fell in next to Jill side by side both on their backs. Frank’s massive penis was slowly softening. After a few more breaths, Frank was surprised as Jill rose up and went straight to Frank’s crotch and began licking all of the commingled juices and effluent from their lovemaking. She then swallowed Frank’s cock to the hilt. Jill then surprised him even more by lifting her leg over Frank’s head and pushing her crotch and vagina into his face, Jill’s smell was overwhelming Frank’s senses. He lifted up and began licking and sucking all of his cum and the contents of Jill’s pussy, and swallowing and swallowing. His dick started to get hard again. Jill kept it in her mouth as long as she could, but Frank’s hardness was overwhelming. Pulling off, she left a long trail of her saliva mixed with her juices and remnants of Frank’s cum.

Jill then pulled herself forward, lifted up and pushed Frank’s hard but well-lubricated cock completely into her vagina. She shook with an orgasm. Then she laid with her back on Frank’s chest somehow keeping him fully inside her. As she lay back she orgasmed. Frank lifted his knees toward his chest to keep inside of Jill as she straddled him in reverse.

She said, “Fuck me.”

And Frank did. He reached up to grab hold of her magnificent breasts to hold her. His fingertips encircled her aureole and pinched her nipples. She shuddered. Jill then reached up with her hands, grabbed Frank’s hands and with a touch pinched her boobs and orgasmed. Frank pinched her nipples, understanding her urgency. She orgasmed. Frank pinched her nipples again and again. Jill orgasmed again and again. Frank followed.

Before they fell asleep, Frank said, “Still want to marry me?” Jill kissed him and as she fell asleep, she said, “Yes.”

Published 
Written by GhostedWriter97
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