Where's Waldo? The Beginning

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Slickman
Slickman
8,174 Followers

Jill moved out onto the patio and saw Tommy sitting near his parents and sister. He smiled and she smiled back. He was the only young guy there and had to be Waldo she thought. She moved over to a chair next to his and slowly removed her shirt and shorts.

Christine and Richard stood in the kitchen watching Jill's nearly naked body wiggle to the small diving board. She stood proudly on the back making sure everyone including Tommy saw her nearly perfect body and then took a long high step to perform a perfect jack knife into the water.

"Take it slow with her," Christine whispered. "She's a virgin." It was the first time she had told him.

"Are you sure she will do it?" He asked not really believing anyone would really fall for the Waldo thing.

"I think so but until you push it in she might change her mind," she laughed. She looked across the patio at Vic who was watching Richard and her. She grinned and waved at him. She had plans for him later.

The first hour they all mingled and got to know each other especially the new parents and girls. Jill was puzzled why Tommy had not said much to her and spent most of his time talking to a new transfer girl with long legs. She had almost given up hope until she went into the house to use the bathroom. The house was empty when she went in but when she exited the bathroom Mr. Wright was standing there smiling. She started to say something when he looked her eye to eye and said, "Where's?"

Jill froze not expecting Waldo to be an older man especially her coach's husband. Shit if the coach found out she would be kicked from the team and lose any chance for a scholarship. She had fantasized about Mr. Wright before but it was just a dream mostly a wet dream. Now it was real.

The word rumbled from her lips. "Wal...do." He smiled and took her small hand in his and walked her to the stairs. Her legs were weak as they walked up the stairs and into the master bedroom. He closed the door behind them and looked down at her cute butt in the tiny bottom. Since he was wearing swimming trunks it wouldn't take them very long to get naked. His fingers reached up onto the knot on the back of her neck and pulled the two strings until he held them both in his hands.

"Oh God," Jill thought feeling her top being untied. She gasped when he pulled the top down over her bare white breasts and although he could not see them yet she was standing topless in a room with an older more experienced man. He untied the other knot and let the top fall to the floor. Next were the two knots on her waist. He pulled the strings at the same time and the back of the bikini fell half-way off her ass.

"Shit," Richard thought when her pure white ass cheeks appeared. They were better than he had imagined. He pulled the bikini bottom down to her thighs and she opened her legs to allow him to pull it down and off her body. She was now naked in front of him facing away. He wished he could talk and tell her how beautiful her ass was but he remembered the stupid Waldo rules. He took her shoulders in his hands and twisted her until she moved around to face him.

Jill's eyes were closed as her body was exposed to a man for the first time. She knew her rosy pink nipples were pointing upward and her virgin pussy was extremely wet in anticipation of what was to come. She bit her lower lip and peeked out to see him smiling. She smiled too. But, the smiled disappeared when he took her two hands and put her fingers down into the top of his trunks. He wanted her to push them down over his long hard penis.

It was like opening a special present. She took her time and slowly pushed the elastic in her fingers down until she felt the resistance of his member. At that point her fingers pulled the waistband outward until she saw her first hard-on. She gasped when it curled outward before popping straight up at her face.

Jill bent at the waist to push the trunks down to his ankles. Her eyes looked forward to see this manhood only inches from her lips. He stepped out of the suit and she stood back up to look down at her first totally naked male. She was having trouble breathing.

Richard took her hand and led her to the large king-size bed that was turned down and waiting for them. He allowed her to climb under the sheets before he moved under with her. When his body pressed into hers she felt his hardness against her hip for the first time. She allowed him to turn her body towards his and to move his lips to hers.

*****

Christine was talking to one of the mothers by the kitchen door when she saw Vic pacing back and forth while looking at the house. He knew his daughter had gone inside about fifteen minutes ago and realized it was "Where's Waldo" time. Amy was also talking to another parent so he moved swiftly to the door but was blocked there by Christine. "Going somewhere?"

"I...uh...need to use the bathroom," he lied.

"Me too," she whispered as she led him into the house. "Let's use the one upstairs."

Vic followed her and noticed her nearly bare ass as she walked up the stair in front of him. He just wanted to make sure his daughter was OK and was a willing participant. As they got to the master bedroom door Christine stopped. They heard Jill's moan.

*****

"Ohhh!" the virgin moaned when his lips found her tiny nipple and his fingers parted her thick bush. She suddenly realized how lucky she was having an experience man who was taking his time touching and kissing her. As he rubbed over her hard clit her fingers explored down under his body until she touched his hard sex. She had only touched one before in the back seat of a dark car and it was less than a minute before the boy climaxed into her hand.

"OHHH!" She moaned louder when his lips moved down into her hot slit.

*****

"Is he hurting her?" Vic whispered as he leaned his ear against the door.

"No," Christine giggled. "Let's go into the library and I'll prove it to you."

Vic followed figuring he would be able to hear better but when she closed the door and led him to the desk he realized the image on the video was his daughter about to be fucked for the first time. He knew it was wrong staring at her naked breasts under Richard's chest and at her bare thighs now wrapping around his hips.

"Isn't she lovely?" Christine asked as her fingers moved down into his trunks and pulled out his straining prick. She pushed down her bikini bottoms and guided him onto the desk chair before straddling his lap and pushed her dripping pussy down his gigantic hard-on. His eyes never left Richard's ass as it lifted and pushed downward. Richard was taking her virginity while he watched and it was beautiful.

*****

"AHHH!" She groaned when her hymen gave way and his shaft pushed steadily into her hot box. She realized she was now a woman and probably the last female in the senior class to loose her virginity. His hips started a very slow in and out fucking motion which transformed the pain and pressure to bliss and pleasure. After a few minutes Richard moved to the side and pulled her on top of him. It was Christine's plan to make sure Vic got to see every naked detail of his daughter and her first fuck.

Christine realized Richard had changed positions because Vic moaned and started fucking up into her a lot harder and faster. She was facing away from the monitor when she whispered in his ear, "Look at her wonderful ass and pussy." She knew the camera angle allowed him to now see Richard's penis moving in and out of her pink folds.

"OH GOD YES!" he cried out when he climaxed. As his body landed back on earth he saw his daughter have her first cum from a man's cock and Richard's face smiling towards the camera. He realized he had been set up but was not angry because he had done a similar thing to fuck Christine.

"That was wonderful," Jill whispered in Richard's ear as they lay together.

"Shhh," he whispered back as he pulled her face up and kissed her on her forehead. He moved out from under her and dressed. He hurried downstairs to make sure none of the parents needed anything as his wife finished off Vic.

*****

Vic rode in the car back to their house looking periodically at Jill's smiling face in the back seat. She had not stopped smiling since they got into the car.

"That was a great cookout," Amy said smiling.

"It really was," Jill purred from the back seat.

"I must agree," Vic said smiling. Little Vic was asleep in the seat next to his sister.

*****

After everything was cleaned up and Amanda was put into her bed Christine sat next to her husband who was drifting off to sleep on the leather sofa.

"So, did the little girl wear you out?" she teased while rubbing up and down his thigh.

"Uh huh," he smiled without opening his eyes. He felt her body move into his.

"So do we end this now or keep it going?" She whispered. Her fingertips pushed against his limp covered penis.

"How many people do you think will go for this Waldo thing?"

"Well, I know of two women who didn't even blink. I guess it's the excitement of having sex with a mystery person in a public place. I'm sure there are some who will not go for it."

"We need to meet with Vic and see if he wants to help us," Richard said feeling his penis stirring.

"I fucked him while we watched you take Jill's cherry," Christine confessed. "I hope you don't mind."

He smiled. "As long as it was just sex."

"It was," she giggled. "I've had more sex the past few days than all of last year."

"Where's?" He asked.

"Waldo," she giggled. For the next hour they touched, sucked, licked and fucked without saying a word.

*****

When Vic got the call from Richard he was surprised and was able to get away from the office for a few hours to meet Christine and him at their home. He knew it was about the WW club but didn't know what they wanted.

After greeting them at the door they moved into the dining room where a large flipchart was set up. On the chart was his name at the top with Christine's name under it connected by a single line. A dotted line came off her name to Richard's with Jill's name under his connected by a solid line.

"What's that?" Vic asked.

"The Waldo pyramid," Christine answered. She had taken off from school for the day and had asked her assistant to run the practice later on. "It started with you and it went down to me. I brought Richard into it and he selected Jill. To keep this going we all need to select another person."

"All?" He repeated. "Jill too?"

"Yes, Jill too," Christine said. "And, since we will be putting a lot of time into keeping this going we need to bring your wife into it as well." She saw the fear on his face.

"She will never do it," he said firmly. "Amy was brought up in a very religious family and would never cheat on me."

"I thought I could never do it either but I wanted to do it," Christine said. "And, you never thought your daughter would be willing either."

"So I guess you will be Waldo for my wife too," Vic said looking at Richard.

"I wanted to but Christine thinks we need to bring another man into the club for her. Is there anyone you know of that she might be more willing to do it with?"

"Shit, I don't know." He thought for a minute. "There is this one man at church who leads the choir she sings in that she talks about all the time but he is as religious as she is."

"Leave him up to me," Christine said. "I hope he is good looking."

"I guess so but he does nothing for me," Vic laughed. "He is married and has a knockout wife."

Christine smiled. "Why don't we really give this club idea a test. Why don't we set you up to be her Waldo and me up to be his at the same time?"

"The worst that can happen is that they both refuse to wear a red shirt and do not participate," Richard said.

"What if they tell others about our involvement?" Vic asked.

"They will have no proof," Christine answered. "All they have are unsigned letters and if they refuse to have sex with us so what?"

"What are their names?" Richard asked.

"Paul and Mary Jenkins," Vic answered.

*****

It was on Sunday morning that Richard and Christine saw Paul and Mary for the first time. They sat next to Vic's family and sang as loud as any of them. It was after the service when Jill cornered Richard near his car in the parking lot.

"Do I get to see you again?" she whispered as she stood smiling in her clinging silk dress.

"Actually yes, I need to talk to you," he said as he opened the door and followed her into the car.

"Here? You want to do it here?" She asked looking around.

"As much as I want to right now," he answered, while staring at her firm chest. "I need to know if you want to continue to the next step of the Waldo club."

"Well, yes, I guess so," she said, not sure of what the next step was.

"You now get to pick the next person you are to seduce as Waldo."

"Me? I get to choose who I want to fuck?" She giggled when she realized she had said the "F" word in the Church parking lot.

"Well, yes if that's what you want to do. You can do oral sex or anything mutually agreeable to."

"I'm beginning to really like this club," she giggled. She looked all around the car and didn't see anyone nearby. "Can we do something right now?"

"It's too dangerous," Richard said.

"What if you kept an eye out?" She grinned.

"What will you be doing?"

"I've never given a blowjob and would like to try it with you?" She blushed.

"Oh, why didn't you say so," he laughed as he unzipped his pants and pulled out his limp noodle. It didn't stay limp for long because as soon as her virgin tongue licked across the tip it sprang up ready and willing.

He looked down at her light brown hair bobbing up and down on his lap and her short dress which had pulled up high over her silky pink panties. She really didn't know what she was doing as she licked and sucked on his tool but it just made it more exciting. He saw an older woman walking their way and tapped her on her shoulder. She popped her lips off and sat up while pushing down her dress. Richard covered his hard-on with his hand.

"Hi," Mrs. Johnson said as she passed the car with the older man and his daughter sitting in the back. "It's nice to see a father and daughter spending time together."

"Yes Ma'am. My daughter and I are very, very close," Richard smiled. He turned and kissed Jill on her forehead.

"You two have a nice day," she said as she pulled her little white purse up her shoulder and shuffled to her old Ford Fairlane parked on the last row.

"We will," Richard said as he turned to watch her walk away. "Well daughter, you need to finish what you started." He moved his hand from his prick and smiled as her mouth dropped back down on his all day sucker. "Thank you Waldo," he thought.

*****

Vic and Christine watched Paul and Mary Jenkins as they hugged and spoke to the members of the choir including Amy. "He is quite handsome," Christine whispered.

"And, she is really stacked," Vic grinned. "So if they decide to join where do we do this?"

"I noticed on the flyer that the church is having a choir presentation at the Civic Center next month. Other church choirs will be there and it will take place most of the day. Why don't you and I go down and check it out?"

"You're really getting into this Waldo thing aren't you?" Vic whispered. He squeezed her butt and she slapped his hand away.

"What kind of woman do you think I am?" she giggled as she walked away.

*****

Mary was the first to receive her invitation letter a few days later. It was placed in her morning newspaper and she saw it when she sat down at the table for her morning toast and jelly. At first she thought it was from the newspaper so she just sat it aside and finished her breakfast. Paul was at the church in his normal weekly scheduling meeting so it was her morning to just sit back and relax. She folded the newspaper and placed it where she had put it the past eight years for Paul to read later. Their live was so scheduled and predictable. As she stood she saw the letter and opened it expecting to see an invoice but instead saw the invitation. She had to sit down as she read it again.

"Oh my God," she said aloud. Who would even do such a thing? She quickly tore it into little pieces and dropped it in the garbage can.

An hour later, Paul returned to his car and found an envelope on the driver's seat. He looked around and saw only the gardener cutting the hedges nearby. After sitting and starting his car he opened the letter and read it. He turned off the car.

Mary was in the shower when he returned to the house. He hid the letter in the top desk draw after reading it one more time. He tried to think of all his friends and those at the church and had no idea who would want him in a sexual way. Like most men he appreciated the soft curves of women and even made sure the choir had as many of them as he could recruit. Did one of them want to have sex with him? He moved upstairs and heard his wife drying her hair in the bathroom. Without knocking he pushed open the door and froze. Mary was standing naked before him. She had never been so brazen before.

"Hi honey," she said smiling. She saw his shocked face and giggled. After months of working out in the small gym down the street she had gotten her body fat down to the lowest ever. It was the first time it had been put on display and from his reaction she knew the sweat and work was worth it.

"Wow," he said looking at her tight buttocks and thin waistline. "Is this my wife?"

"I can see you like the new me," she grinned looking at the front projection of his slacks.

"Yes, very much," he moved behind her and squeezed her cheeks. "How much weight did you lose?"

"Actually only ten pounds because I put a lot of muscle back on." She squeezed her tight butt. She turned off and put down the hair dryer before turning to show her somewhat smaller breasts and her neatly trimmed pubic mound.

"You shaved?" His eyes looked at her bald pussy lips for the first time.

"I did it this morning," she giggled. "Do you like it?" Her thighs slowly opened displaying her glistening pink folds.

"YES!" he said loudly. He pulled her nakedness into his body and whispered in her ear. "You did this for me?"

"Yes," she whispered back feeling his phallus pushing into her taunt abs. Her fingers tickled their way down his stomach and over his bulge. She leaned up with her opened lips to find his. It was the first time ever they had sex in the daylight and the first time ever they both climaxed at the same time. Both of their minds were on the Waldo letters.

*****

It was the following Sunday that both Paul and Mary wore red to the church. His shirt was a red striped dress shirt and she was wearing a bright red blouse. Vic looked at Christine and winked.

The next week they got the meeting letters out to them and it was two weeks later that Christine and Vic walked into the large Civic Center together. Vic had a copy of the schedule from his wife who was singing in the choir that day. Their church was to go on first and then later in the morning. Both Paul and Mary were wearing red and white clothes.

Christine saw Vic's hard-on as they listened to the choir presentation and whispered, "You better calm down."

"I know," he whispered back. His eyes were on Mary's body as she walked onto the stage and stood next to his wife. The red blouse and white skirt looked wonderful as they clung to her shape. He could see her eyes looking around at the various men probably wondering who would approach her. He looked away when she glanced in his direction.

After their performance Mary excused herself from her husband to go to the restroom. It was a perfect time for Vic to follow her. He sat at the entrance to the hallway leading to the restroom and waited for her to come back out. He heard her voice and stood to confront her with the "Where's?" when she walked around the corner with his wife. He froze.

Slickman
Slickman
8,174 Followers