Chapter 3

Monday

School Counselor

Zack knocked on Ms. Franks’ office door before entering at 2 pm on the dot. As she bade him enter, Penelope came around her desk and gave him a hug. His Aphrodite was dressed in a dark pantsuit with a low-cut blouse that showed off the tan tops of her generous breasts. The tall dark-haired woman hugged him to her soft chest. He had spent many hours with those tits over the summer when for a few weeks she took the place of his regular escort and companion Melisa.

Delicious memories, a dream come true to sleep with her. After half a minute they separated, she kissed him on the lips, and they took their seats. Ms. Franks sat in a comfortable-looking high-backed chair and Zack was across from her on the well-worn couch.

Penelope had her tablet and stylus on her lap for notes. She quietly listened, legs crossed, taking notes, as he told her about the weekend, everything that he thought she would find interesting. Penelope in her Madam Franks – Ph.D. sexology student role had been with them in Florida at the ‘family sex week’ with the Naturalists. So, he didn’t hold anything back when it came to talking about sex.

“That’s all?” she asked. Eyes on him smiling, all knowing.

There was more. Ruth. For some reason, maybe because it was out of the norm, he had held back. Seeing her look, he told her about Ruth’s offer to let him breastfeed from her tits. The first meeting with Ruth in the back parking lot of the school. Taking Heidi with him last week to sit in the back of Ruth’s 4-Runner and feed off her milk-filled breasts. ‘Madam’ Franks had been in the big tent in Florida and watched him and his sister suck on Greta’s milky boobs. She just nodded knowingly at his confession, tapping the stylus to her gorgeous lips.

“Thanks for telling me, Zack. We’ll come back to this,” she said in a non-judgmental voice. But she did smile.

Ms. Franks came to the reason she asked him to come in for a counseling session.

“Zack, I asked you to come in because I have a special job for you.” She said as he nodded, “I want you to accept a couple of sex dates.”

“Uh sure, I just haven’t had time yet,” thinking she was criticizing him for his slow start.

“No, you’re fine. You have a good reputation among Saint-U moms. Especially the moms of freshman girls who have seen your videos and positive feedback. I have a couple of shy virgin girls, cute but really shy whose mom wants them to sex date.”

“Uh okay,” he said looking for the trap or catch. “Do I know them?”

“I don’t believe so. Trust me on this. You will need to meet each of them first and get to know each other; girls need work sometimes before they jump in bed. Each girl’s mom will contact Julia to request the date. Just agree and have your mom call me if she needs to. Do this and I can help you out with Ruth.”

Zack would do anything for Penelope. She knew he would but was being nice in asking and offering a reward. Not that sex with two virgin freshman girls was not a reward.

Ms. Franks turned her tablet so he could see two pictures, headshots of the girls. The first was a smiling, young-looking blonde with curly hair and the second was a very pretty, serious looking brunette with glasses.

“Fine, they look okay. And what about Ruth?” he said curious to hear what she had to say.

“Have her come to my office on Wednesday. You three can use the couch. Ruth will like that more than the backseat of a truck. I’m usually out during lunch roaming the halls and cafeteria. Have her call me first. Deal?” As she spoke, she came and sat next to Zack on the couch.

“Yeah deal,” he said as her right arm settled on his shoulders.

“So, you like to breastfeed? I don’t have milk, but we still have a half-hour left in our session, and you have been a very good boy.” She teased in her husky sexy whore voice.

Eyes on Zack, Penelope began to unbutton her blouse. Her big round breasts were supported by a lacy red underwire bra. Zack moved a hand inside her top. He hadn’t felt these girls since he went back to sleeping with Melisa, he had missed them. Yup, he would do almost anything for this woman, she had the power.

Penelope took off her blouse and turned her back letting him unhook the the wide bra strap, freeing her juicy melons for him to put his hands on.

“Tell me about the Sex Date party at Kelly’s house.” She said as she took a seat on the couch on his left. “You’ve seen what she posted about the party, it’s very artsy,” Penelope said, letting Zack put his hands on her breasts.

He was torn, he wanted to suck on her delicious dark nipples, pretend she was his mom feeding him. But Zack did feel a need to confess to share with this beautiful woman, his Helen (of Troy), a bit more about the party. The artsy video was cool, but it focused more on Kelly and Tucker than the other guests like Zack and Gal.

With his hands on her heavy sagging tits, he used his fingers and thumbs on her nipples, teasing them until they were hard.

“You saw Gal Abrams’s video and Clara Van Winter’s with Sydney?” he said thinking of a couple of names from the party he knew. He liked Sydny the softball pitcher and team captain, he had gotten in a nice slow fuck with her before the party ended. She was bisexual and had strong thighs he figured that much out.

“Yes, I did, and Simons with Kelly. He has become very popular since he posted his date video.” Penelope said. “Your touch feels nice. If you ever get tired of Melisa...” she said teasing him with a big white smile.

Yeah. Any dorky freshman boy who posted a video of him losing his virginity to the beautiful head cheerleader would make girls, and their moms, wonder what Simon had that was so special.

He closed his eyes and talked as Penelope took him in her arms. A lot happened that night he would just choose the most interesting and summarize.

Standing in the kitchen with Kelly, he and his date and took turns licking Kelly’s wonderful breasts clean of Simon’s drying cum. Kelly giggled the whole time they ran their tongues over her breasts.

“I like both of you,” Kelly said in a husky voice. Her creamy pale chest was a little flush as she looked at her ‘boyfriend’ Tucker who had come up behind Gal, placing his hands on the slender shoulders of the smaller girl.

Tucker played football, one of the defensive positions. There was another football jock here, the team punter who was better known for being the debate team captain than good at kicking a football.

“What’s going on? I miss anything?” Tucker said taking a bottle of water from the refrigerator.

“Nothing really, they were just helping me freshen up.” She answered, tossing Gal a wink.

Zack took a moment to admire Kelly. She was near his height 5’8”, her blonde hair had platinum highlights was tied in two cute pigtails. Full heavy breasts and a photogenic face that would not be out of place on the cover of any girls Teen magazine. She had that unique ‘I am smart and beautiful’ look wrapped up in one delicious package that was only mildly intimidating.

Zack and Pete had discussed Kelly at length, agreeing the new head cheerleader was best described as a beautiful blend of actresses Olivia Dudley from The Magicians, an old favorite of theirs, nice big round boobs and an intelligent look combined with the white smile and dimpled chin of Lili Reinhart from Riverdale fame. Kelly and Tucker had been a part of Saint-U’s promotional materials for the last couple of years. A definite 10 in looks and athletic ability, she had been cheering since middle school and playing girls sports.

Kelly saw his look. “What?”

Zack felt himself blushing. “You’re beautiful. Thank you for inviting me tonight.” His cock had started to find life again as he played with her tits. She noticed.

Kelly looked at her boyfriend “You can thank Tucker.”

Tucker had his hands on Gal again, having chugged his water. His big right hand was massaging her neck as he whispered into her ear.

Gal was looking at Zack. Her big dark eyes questioning.

He was torn between Kelly, a fully developed gorgeous girl-woman, and his date. He felt protective but at the same time Gal’s family motto was ‘Sex was Sex don’t confuse it with love’.

Zack gave her a slight shoulder shrug as Tucker pushed aside a handful of chestnut hair and kissed her neck.

Both he and Kelly were watching.

“Tucker honey, let’s go back to our guests and give them your speech.” She said.

“You’re right,” he dropped his hand from her neck to Gal’s ass and gave it a squeeze. “Later?” he said.

Gal turned and nodded at the older handsome boy. “Okay.”

Kelly took them both by the hand and followed Tucker back to the living room.

Penelope interrupted his story. He was lying back on her using her breasts as pillows. She had a hand inside his shirt.

“Yes, I know. Turker is running for student body president, that’s why most of you were there, so he could ask you to join his campaign.”

Zack kissed Penelope’s tan arm as she stroked his chest.

“We’ve had his registration forms for a week. He listed you as the webmaster for the campaign.” She said as her fingers tranced his nipples, she loved to do that to him when they rested after sex. “Tell me about the deal you made.” She kissed his forehead.

Ah yes, his deal with Kelly to ‘buy’ his support for Tucker’s campaign.

Tucker took Zack aside in the living room and made his ask. Zack had a heck of a good reputation when it came to programing and computer work, Turker wanted him on his team. Kelly stood by, waiting. Zack didn’t answer right away. He was a busy guy and wasn’t sure he wanted to deal with school politics.

Kelly had spoken up. “Would it help if I said you would be working closely with me as I’ll be directing the social media team?” Her icy blue eyes locked on his. Gal stood behind Zack holding his hand, gripping it tighter. He waited counting time to himself.

“What would it take?” she said stepping closer into his space as Tucker watched.

His cock was still hard and pointed at her toned flat belly. He leaned in and spoke in her left ear as he put a hand on her belly, her abs were rock-hard at his touch. Kelly’s perfect breasts and tight body was of the type that most men, like his dad, and Zack, were drawn to like moths to a flame.

Kelly leaned back eyes on his face, a hand on his chest. “Sure, we can do that tonight, and I can arrange for cheerleaders to be at ALL your baseball games next season if we win. Anything else?”

“Yeah, my buddy Pete. He’ll work with me, it’s a big job. Get him a Sex Date with a cheerleader.” He said with a straight face. Tucker smiled and stuck out his hand.

“Thank you, Zack! Pete will get his pick; I know my girls. It’s going to be so much fun working together.” She said kissing him on the cheek.

“I, we, appreciate the support,” Tucker said diplomatically giving Kelly’s perfect tight ass a light slap. “Now can I borrow Gal for a little while?” he said with a warm inviting grin.

He watched Gal leave with Tucker, she cast a glance over her shoulder at him. He waved. Kelly promised Zack they would meet later and consummate the first part of the deal. Did he feel jealous about Gal and Tucker, he always did when he liked a girl and liked Gal. Tucker did have a nice cock, well proportion and pubes neatly trimmed, balls hanging just right. Sydney the blonde good-looking softball player, who had one of the largest social media accounts of all the school athletes, had let him know she was interested in getting together. He had the feeling she would be up for a foursome with Tucker and Gal.

Penelope chimed in. “What was the first thing you asked for? I’ve heard rumors.”

Zack looked at the wall clock. It was a quarter to the hour he would have to leave soon for his next class.

“It will be better if I show you. I promised to not post this.” Zack reached for his device which was on the couch next to him.

Penelope brought her head down next to his as he leaned against her naked chest and lifted his device so they both could see the video he pulled up.

“It’s kind of long, I’ll just show you part of it, so you get the idea.”

“Okay, but you will send this to me if I ask?” her breath warm against his cheek.

“Of course.” He could never say no. He picked a spot early in the video and let it play.

Zack was on his back on the twin bed in the middle of the living room. Kelly straddled his hips. He had his hands on her narrow waist supporting her as she used her strong athletic legs to ride his cock.

“Go Zack Go!” Kelly cheered as she shook one green and one white pompom in the air.

Green, white, and gold were the school’s colors, the mascot was the medieval Knight, usually shown on horseback with a lance.

He thrust up into her. Kelly’s large boobs bounced seductively on her chest making small circles.

“Fuck me, fuck me, harder!” she chanted as sat on his cock and shook the pompom.

Her blonde pigtails making her look younger than seventeen, flailed in the air as she tossed her head back and forth giving her all to the unusual cheer.

He reached for her tits palming both.

“Squeeze them, suck them!”

She bent down and he took the right hard pink nipple in his mouth.

“Bite it, suck it. Bite it, suck it!”

He moved to the left breast sucking on the hard nipple, giving it a love bite, and thrust with his hips.

Behind him, Maria, the former head cheerleader had her device out recording, for a modified POV shot. Kelly’s pretty mom was off to his right with her device. She was trying to record the sexy improvised cheer as Tucker went down on her, lapping on the older woman’s cunt.

“Suck me, fuck me, Zack!” a shake of the pompoms. His face was buried between her tits.

He stuck a finger in her ass hole as he held her down on his cock.

“Go Zack, go!” her voice at the highest octave now.

And on the cheering for Zack went. He had fucked her silly as most of the party guests sat and watched grinning from ear to ear, he hoped. Zack would be working with most of them for the next month on Tucker’s campaign.

He stopped the video. If he didn’t, he would come in his khaki pants.

Zack sat up and looked at Penelope. “So yeah, that was my first ask it went on for a while longer. Now anytime I need extra motivation, I can play this to cheer me up.”

“Very creative Zack.” She said as she put on her bra. He helped. Then her blouse.

“The campaign starts Wednesday. Is Tucker ready?” she said standing buttoning her shirt.

“Steven, the debate team captain is his campaign manager. He’s a smart guy and we have a good team. Me and Pete worked on the webpage during our computer lab, it’s ready.” It wasn’t hard work and between he and Pete they would keep the Sanit-U hosted web page updated with news and protect it from attack. Saint-U student body politics could get rough at times.

They kissed inside her office before he left.

Overall, the first official Sex Date Party he had attended was a lot of fun. More wine was drunk, partners swapped, and games were played until those who were not going home crawled into bed well after midnight. He woke up early Sunday morning with a mild hangover and thirsty with a hard-on. Next to him on her belly was Kelly under a baby blue duvet sound asleep, looking cute. The noise that woke him was Simon fucking a groggy Gal next to them on the queen-sized bed. Her legs were open as the boy slid his cock in and out.

He considered his hard cock and spotted the half-full bottle of water on the nightstand in the early morning light filtering through the blinds. He quenched his thirst and then bent down whispering in Kelly’s ear. He eventually got a nod, okay and she opened her legs slightly. Before he could start, Simon grunted, then collapsed next to Gal pulling the duvet over them both. Zack mounted Kelly from behind spreading her ass cheeks. Collaborating with her for the next month, win or lose, was going to be a lot of fun.

Life was good for him and Gal. Both had made new friends and accepted what each had done at the party. Later that morning they had breakfast was Gal’s Dad and Rebekah, a happy couple tired after a long night.

Tailgate Talk

On Monday afternoon, Zack saw Rebekah in their AP World History Class for the first time since he canceled weekend plans with her and everyone else. They sat together but had no time to talk as the teacher jumped right into a lecture on early Bronze Age cultures. They did not talk until the 90-minute class was over and they were heading for the student parking lot, the class had been their last. Heidi had band practice for another hour and would find her own ride home. Seriously, she needed to get her driver’s license.

At his truck, they stopped, and he pulled down the tailgate so they could sit.

Rebekah leaned against the tailgate arms crossed as she waited, her dark eyes sending him a message.

Resting against his backpack, he jumped right in, asking about her weekend. Rebekah appreciated the direct approach, not much for small talk.

“So, you had a date with Pete?” He said. Not really a question, just a place to start. She was the one who said she wanted to talk. Pete would be along soon.

Zack had a hard time reading her pretty face. With all that curly chestnut hair, dark looks, and big mysterious eyes, she hid her emotions well. Rebekah looked good in her short green skirt and thin white school blouse. This school year, if the light was just right the girl’s uniforms left little to the imagination of what a girl had on underneath. She wore a bra, her heavy chest supported, and her modesty protected. Rebekah also didn’t like public displays of affection but moved closer and took his hand anyway as students walked by.

“Well, you disappeared for the weekend. Just a message saying you were going on a family weekend out of town. What were us, your friends, who you had plans with supposed to do?” she jabbed with the last words.

Zack had had to cancel a date to hang out at her pool Saturday afternoon. No doubt they would have had sex, his loss. Her sister Gal was probably even more disappointed as she had developed a crush on him, especially after their first very fun Sex Date. He was also supposed to hang out with Pete and work on the next Virtual Reality D&D adventure module they were designing. And of course, there was Kelly he had to disappoint in not being available to work with her on Tucker’s campaign materials.

“Sorry, my dad said we all had to go. A last-minute thing in North Carolina for his work.” He left it at that. Trying to look apologetic. He’d had a great time in North Caroline driving cars, shooting guns, meeting cool people, and of course the sex at the end of each day. He tried to act sorry.

Rebekah nodded, let go of his hand, and sat on the tailgate, letting her white stocking-clad legs swing. They sat in silence for a moment watching the students going to their cars or waiting for rides. They each said hello to people they knew who happened to pass by.

“So yes, Pete had been asking when we were going to have our Sex Date. I agreed and said why not Saturday when I found out you broke a date with him too. You know he has a kind heart and wants to impress.” She smiled at Zack “and I kind of like him.” she let her right foot tap his playfully.

“Can’t blame you, he’s a smart guy,” he replied. Trying to not act jealous of his best guy friend for enjoying an afternoon of good sex with a great girl. Rebekah had very progressive views on sex, thanks to her mother. She would not stand for him being jealous of who she slept with.

Rebekah gave him a look that said he better feel sorry and then went on talking. “So, tomorrow after school we’re playing tennis at Bethany’s house.”

Zack nodded, watching her talk.

“Then we will ‘study’, she said. “That will be our chance to help Pete out. You and I know you fucked Bethany at Brothel Night, and she has been after you since then.”

“Yeah, we did that night. Was kind of weird when her grandfather joined us,” he added maybe not helping the conversation.

Bethany was a golden-haired girl from Santa Barbara, California who had come to live with her grandfather in Nashville who happened to be a dean at Saint-U. If she hadn’t gone back to California for the summer, he probably would have gotten sucked into a sex date with her.

“My sex date video with Pete, which I used all my editing skills to make him look like a stud, has been posted to the Sex Date group in the cloud. So, Bethany should be able to view it if she wants,” Rebekah said.

Zack continued nodding. He might take a look at it himself.

“After we go inside to study, follow my lead. Let’s get those two together. Agreed?”

He took her hand again. “Yes, I agree with your devious if not obvious plan,” he said. Her plan would involve all four of them being naked together and probably having sex if he understood Rebekah’s plan. No reason to argue with his smart Jewish Princess.

Rebekah saw Pete walking towards the truck with a grin on his face.

“Here comes Pete. I’ll say hi then I must get to Temple for a meeting. You’re more than welcome to join me?”