Jack's Education Ch. 08

Note to reader: The stories previously posted in the series "Jack Awakens" and "Jack's Exploits" were originally the opening chapters of a book which I had started writing over the last few months. I have now decided to post the entire book, which traces the sexual development of a high school boy during his senior year, hopefully at the rate of one chapter each week. The stories previously posted have been retitled as "Jack's Education" in strict chronological order, under the "Novels and Novellas" classification, as the book covers a variety of sexual behaviors and experiences.

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CHAPTER 8

While they enjoyed their dinner of sweet and sour chicken Maria and Jack discussed the plans for Maria's forthcoming trip to San Francisco. Jack was still a little distracted from having seen his mom having sex with his best friend Tim earlier that afternoon, and pondered whether he should tell her he had seen them. He was sure, however, that he wouldn't tell her the whole truth that he took a bunch of pictures catching them in the act on the living room floor.

Jack looked at his mom in a completely new light now. Before today she was just his mother, a successful lawyer working hard to provide for her family, perhaps working too hard to numb the sense of loss she felt after losing her husband in a car accident. Now he saw her as a mature woman with sexual needs just like any other, and this combined with his own sexual awakening, caused him to see that she was an attractive woman, who he could understand that might arose desire in men of any age.

He thought about her liaison with Tim and wondered how it came about. Did Tim make a play for his mother because Jack only yesterday had spent the afternoon in bed with Tim's mother? Was it a case of "you fucked my mother, so I'll fuck yours"? Or was it the other way round where Maria seduced Tim into a sexual act to satisfy her own needs? He could understand that, too. But why did she choose Tim?

His thoughts were interrupted by the phone ringing, which he got up to answer and was delighted to hear Toni's voice, "Hello, Jack! How are you?"

"Hello, Toni! It's good to hear your voice. How are you doin'?"

"Good, Jack, thanks! Listen, is Tim still there?"

"Tim? No, Tim isn't here. I haven't seen him."

"Really? He said he was coming over to your house."

"No, I haven't seen him, but I was out most of the afternoon, so he could have. Shall I ask my mom?"

"No, that's OK. I really called to let you know I'm going back to school tomorrow and wanted to say bye. I'll see you when I'm home for the summer break."

"OK, Toni, but I wanted to see you before you went. Are you doing anything special tonight?"

"Not really. I was going out with one of my friends. Want to come with us?"

"Yes, that would be nice."

"Are you by yourself?"

"No, my mom's here. Why?"

"I wanted to tell you something personal."

"What is it?"

"My period's over now, so I'm ready to make good on my promise. Are you game?"

"Sure, any time!"

"OK. You don't have a car, do you?"

"No, not right now."

"OK. Pick you up in a few, OK?"

"Great! See you then!"

"Bye, Jack!"

"Bye!"

He hung up and told his mother, "That was Tim's sister, Toni. She's coming to pick me up in a few minutes and we're going out with one of her friends."

"All right, Jack. She was looking for Tim?"

"Yes, it sounded like she thought he was here."

"Well, I didn't get a chance to tell you, but he was here before you got home."

"Really? What did he say?"

"Nothing much. He asked for you and waited a while, but then he left."

Jack didn't answer right away. He was wondering whether to tell her that he knew Tim had fucked her, but decided to leave it alone. If she wanted to, she could tell him. "So how long did he wait?"

"Quite a while. Where did you go?"

"I was to Angela's house. She needed some help with homework."

"Well, I called there, but her father said you weren't there!"

"Actually, her parents were out when I was there, and I left before they got back." This conversation had taken an awkward turn and he wanted to end it. "Maria, I'm going up to change my clothes. Toni will be here soon."

"OK, Jack. You're growing up fast! Just be careful with these girls, OK?"

"Right, Mom. You know I'm a good boy!"

They laughed and the tension was broken. Jack headed upstairs to change for his date with Toni. He thought carefully about what he should wear, and then, hoping for at least an encore blowjob from Toni, decided to wear nothing underneath his shorts, just as he had that afternoon.

He had just got downstairs when he heard a car horn blow outside. He looked through the window and saw Tim's Beetle outside with Toni at the wheel. He noticed that there was also someone in the passenger seat, but couldn't see who it was.

He went into the kitchen where his mother was cleaning up. "Toni's here, so I'll see you later, Mom." He still hadn't got used to calling her by her first name.

"OK, Jack. Don't be late, tomorrow's a school day and I also need to get an early start."

"All right, I promise I won't be late!"

He almost ran down to the path towards the car and Toni waved to him. When he got close to the yellow Beetle, he saw that there was another young woman in the passenger seat. She had dark hair and was quite pretty, with smallish but perky breasts encased in a tight sweater.

"Hi, Toni!" he said, as she got out to allow him space to get into the back seat.

"Hey, Jack, good to see ya!" Then as she got back behind the wheel, she said, "Jack, this is my good friend Millie."

"Millie, it's nice to meet you," he said, holding out his hand.

Millie shook his hand and Jack noticed how small her hand was in his. "Good to meet you, too, Jack!"

Toni pulled the car away from the curb, saying, "We were going down to Roosters for a drink, but then we remembered they're closed on Sundays. How about we just go back to Millie's place for a while?"

"That's fine," Jack said. "I'm happy to do whatever you want!"

Toni laughed. "That's nice!"

Millie's place was not far away and they chatted merrily as they went. Jack gathered that the girls were friends since they were small, and hadn't seen each other since the Christmas holidays. Millie was a senior at McNab High, the same school where Sara and Betty were teachers, and would be graduating in the summer. Jack asked Millie if she knew Sara and Betty, and she replied with a little laugh, "Sure I do. They're known as "The Odd Couple" at school!"

"Why?"

"Well, it's a known fact that they're virtually married to each other. They never seem to be apart except when in class and everyone I know thinks they're lesbians!"

Jack was surprised to hear this. Had he misinterpreted the reason why Betty had given her number to him? He had thought she was interested in him in a romantic way, but perhaps he was mistaken?

They soon arrived at Millie's house, where she explained, "My parents are away on a cruise, so we have the place to ourselves. I have the key to Dad's liquor cabinet, so we can get sloshed if you want!"

Toni and Jack both laughed, but Toni said, "I'll pass on that, Millie. I have to get an early start tomorrow, but I'll have a beer."

Jack said, "Make that two. I have to get up early too."

"No problem, Jack," Millie said. "Make yourselves comfortable while I get the beers."

Millie disappeared into the kitchen, while Jack and Toni sat down on the couch. A few seconds later Millie came back with three Coors Light on a tray and set it down on the coffee table. They each took one and Millie sat in the easy chair next to them.

"I met a new guy last night at the party," Millie said to Toni. "He's asked me to a pool party next weekend."

"Is he cute?" Toni asked.

"Oh, yes," Millie replied. "We made out a bit at the party and I think we can hit it off."

Toni shot a glance at Jack before asking, "Has he got a big dick?" Jack was taken a bit by surprise at this question, but stayed silent.

"I didn't get to find out how big, but he sure was hard when I felt his pants," Millie responded. Jack was shocked at Toni's next comment.

"You know, Millie, Jack's got a beautiful cock in his pants!"

"Toni!" Jack exclaimed.

"Well, it's true!"

Millie grinned at them and said, "Excuse me, you guys. I'll be right back!"

While she was gone, Jack asked Toni, "What are you doing to me? Trying to embarrass me in front of your friend?"

"Not at all, Jack. Millie's a cockhound and loves to get her hands on any dick she can! I believe she would enjoy yours as much as I'm going to!"

Just on cue Millie came back into the room and Jack could feel his prick begin to get hard right away, for now she had on a bikini that was almost indecent. The top was just two miniscule triangles of fabric that barely covered her nipples, attached by spaghetti straps. The bottom part was hardly any bigger exposing most of her lovely ass and the sides of her thighs. This piece of material disappeared between her legs and it covered only about half of the area where her pubic hair would normally be except that it had all been shaved off. As she showed it off, Jack calculated that the upper edge of the bottom piece was probably only about a half-inch above the slit of her pussy.

"So what do you guys think of my bikini?" she asked. "Think I'll raise some dicks at the party?"

"I reckon you will, just before you get arrested for indecency," Toni laughed. "You going for a dip?"

"Yes, if you guys will join me."

"I'm game," Toni said. "How about you, Jack?"

"I would, but I don't have my trunks with me."

"No problem. Let's go skinny!" Toni said.

"Hey guys!" Millie interrupted. "We have neighbors! Jack, you can borrow one of my brother's suits. You look about the same size as he is. Toni, you want to borrow one of mine?"

"OK, but I'll probably be bulging out of the top."

"That's all right. Jack would probably enjoy that!"

A few minutes later the three of them, towels draped over their shoulders, went outside to the family pool and dived in. Jack was glad for the cool water, as it eased his throbbing erection. The girls were both excellent swimmers and Jack took things easy, trying to conserve some energy. After about twenty minutes they returned to the house and Millie got three more beers as they sat in the living room to talk. Their suits were still damp, so they put towels down on the sofa. Millie sat at one end of the sofa, with Toni in the chair closest to Jack at the other end. They talked for a while about people's attitudes towards nudity and how silly most of them were. After a while, it began to get dark and Millie got up to close the blinds.

"I'm getting cold in this suit," she said. "Me too!" Toni echoed. "Jack, we may as well put yours in the dryer with ours, OK?" "Sure!" Jack said, thinking that he'd be putting his clothes back on. "Allright!" Millie said as she came over to him, stripped off her bikini top and handed it to him. Jack looked down at the damp garment in his hands for a few seconds, and then back up at her exposed tits, which were small but in perfect proportion to her body. As he looked up she turned her back to him as she untied the bottoms, letting them drop to the floor. Jack gaped at her beautiful naked ass then as she turned back around to face him he could only look in amazement as he saw that she had indeed shaved her pubic hair off to wear the suit and she was a smooth as a baby's bottom all the way down to her glistening slit. "OK, your turn!" she chuckled. Toni had already removed her suit, so Jack stood, handed Millie her top back, and began unfastening his trunks. Toni walked over to Millie, her beautiful tits jiggling and bouncing. Jack slid down his suit and pulled it off his feet, conscious that both girls were looking at his cock, which was somewhat shriveled from the cold. Millie gathered up all the swimwear, saying, "I'll be right back!" as she disappeared into the kitchen.

Toni moved closer to Jack and as she did she whispered, "Ready for some fun?" Jack felt his dick swell and then he noticed that Toni's nipples were hard and crinkled from the cold. As he looked more closely at them Toni put her hand on the back of his head and pulled him down to her erect nipples. As his tongue warmed them up she sighed, enjoying his tender touch. Jack alternated between the left and the right, sucking both of them, then gently nibbling them.

Toni pulled away rather guiltily when she heard Millie returning, and she grinned as she came into the room, because she immediately noticed Jack's growing hard-on. "He's looking a lot more perky now, isn't he? What have you been talking about?" Millie asked. Toni and Jack looked at each other and broke up laughing. Toni moved over by Millie, and took hold of one of Millie's pert tits. "Aren't these the cutest nipples you've ever seen?" Toni asked. Jack had to agree for Millie's nipples were large for so small a breast, and a much darker color than one normally sees on such a fair skinned girl. Toni bent down to lick one of the nipples and Millie moaned a little, enjoying the sensation. Jack went over to them and took hold of the other breast, licking that nipple, causing Millie to moan a little louder. She pushed out her chest out and took hold of their heads to encourage them to keep sucking. Jack ran his hand down Millie's back to caress her ass, and then slipped his hand between her legs towards her damp pussy where he found Toni's hand exploring from the front. Together they explored the cavity and Millie, moaning louder, rotated her hips as their fingers penetrated her. Toni pulled her hand away, saying, "Hold on a moment," and she knelt down to take Jack's erection into her mouth. The warmth of her mouth felt so good on his prick that he became fully hard. His cock slid all the way down into her throat, her nose resting against his belly. Then Millie knelt down to take over from Toni, and although she didn't go down as far, she was very talented with her tongue. While Millie slurped on his shaft, Toni stood up to kiss Jack, and his hands immediately went to her bigger breasts to squeeze them in his hands. They were moaning as their tongues wrestled with each other and Toni rubbed her crotch against his leg. Millie's mouth had speeded up on his cock now, soaking it with her saliva.

"You see what I mean, Millie?" Toni said, breaking briefly from their kiss. "Isn't it beautiful?" Millie just nodded, too focused on sucking Jack's dick to stop. Jack's hands slid down Toni's body and she parted her legs to allow him to slip his hand between her thighs. He was surprised to find Millie's was already there, pumping in and out of Toni's sopping cunt, while she slurped on his throbbing dick. Jack slipped his fingers in with hers, causing Toni to gasp with pleasure. Millie licked his balls, breathing hot air against them, driving him to greater heights of arousal. Toni and Jack kissed again, and then Jack used his finger to moisten her nipple with her juices and then licked it clean. "Ohh, yes!" Toni whispered. Jack again slid his fingers between Toni's thighs, working in and out of her sopping wet slit. This time, as Jack withdrew his fingers, Toni looked down. Millie was still sucking his cock, and Jack spread Toni's wetness across Millie's cheek. Toni just hissed in his ear, her tongue darting around it and her tits pressed hard against his arm. Her body was writhing uncontrollably against him.

Toni hissed, "Come in her mouth!" That was the last straw for Jack and his hot cum shot in a rush right into Millie's mouth, feeling like it was the first time had come in a week! He looked down, his cock still spurting its creamy load and saw that Millie was rubbing his cock all over her face, even as cum still spurted across her lips and cheeks. Her tongue, coated with cum, was still licking his dick, and then she sat up, moaning and rubbing it across her nipples.

Toni knelt down to kiss Millie's slimy face, and then licked up a wad of cum from her chin. The two girls kissed passionately and Jack watched in amazement, for he had never seen girls act in this way before. After they broke off their kiss, Toni began to suck Jack's dick again, while Millie was sucking Toni's right breast, slurping on her nipple and rubbing his cum all over her tits. Then Millie's hand dropped to Toni's pussy and soon Toni was moaning as she was feverishly sucking his cock, getting closer and closer to her own climax. Her moans excited Jack again, even as he watched Millie's gorgeous ass moving back and forth. Millie lifted her mouth from Toni's nipple. Millie's fingers were pounding Toni's cunt now, making all of them sway. Toni was moaning, her face contorting as her orgasm was beginning. Still shaking and fucking Millie's hand, she grabbed the brunette's head and kissed her deeply. Millie kissed back, and the two of them began to lick each other's faces, making them wet with saliva and cum. Next thing Jack knew was Millie sitting on Toni's face, rubbing her juicy pussy against Toni's mouth. Jack knelt next to them, pulling on Millie's large nipples, licking them and whispering into her ear, "Come on her face!" Jack breathed into her ear hotly. "Soak her face!" Millie stiffened and groaned, shaking, and then moaning loudly. Jack pinched her erect nipples again and again, and she was virtually jumping up and down on Toni's face. Millie collapsed in a heap on top of Toni, but Toni was obviously ready for more. Millie rolled off and lay panting on the floor, her tits glistening from the sweat that covered everyone. The chill that caused them all to take off their damp clothes was a dim memory, overtaken by burning desire.

Toni started to get up but as Jack lay on his back he pulled her back down so he could savor the flavor of her pussy himself. Gradually, slowly, ever so slowly, she lowered her cunt down onto his waiting mouth. Her twat tasted wonderful to Jack and her juices were flowing like sweet wine into his mouth. He licked and sucked her clit, and she was shuddering with ecstasy as he tongued around her entrance, then slipping down to her anus, rimming it lightly. Toni was panting as she drew nearer and nearer to her climax, but Jack kept her near the edge, her cunt soaking his face with her delicious cream. Millie came over to join them and began licking Toni's anus and cunt, and it was this combination that finally took Toni over the edge as she cried out with utter joy. As Toni relaxed, Millie kissed Jack with long and deep kisses. Jack could taste the remnants of his own cum on her lips, while she licked Toni's cream from his face as though it were nectar.

After she had washed his face, she was ready to try Jack's cock in her pussy. She positioned herself over him and eased herself down on to his dick, taking it easily into her sopping cunt. She rose up and down slowly at first, letting his entire length slide fully into her, then rising up slowly, she slammed down again. After a few minutes Millie was seemingly jumping up and down on his prick while Toni had recovered enough to suck on one of her nipples while pinching the other. Jack reached up and began pinching both of Toni's nipples, rolling the erect buds between his thumb and forefingers. Millie moaned and seconds later came hard on his cock. Jack grabbed her ass and began to fuck her with long, hard strokes, impaling her on his pecker.

"Ugh! Yes! Yes! Yes!" Millie cried. She slowed and fell panting against Jack, drenching with sweat. Jack felt Toni's hand sliding over his balls, then his cock and then saw her lick her fingers.

"That tastes so good!" she declared. "But now, Jack, the time has finally come for you and me to fuck!"

Jack nodded, but suggested that Millie could help them. Toni agreed and knelt on all fours, with Millie lying under her. Jack shoved his hard dick into Toni's cunt and began thrusting, but when he pulled back, Millie kept pulling his cock out to suck it, and to suck Toni's dripping wet pussy. Then she put him back inside Toni and licked his balls as they fucked. Toni's pussy was so slick and wet Jack almost couldn't feel anything and wondered if he was going to be able to come again. Millie ran her hands all over both of them, her fingers gently exploring his asshole and rubbing Toni's clit.