Jack's Education Ch. 09

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 9

Jack had just got home from school when the phone rang. "Hey, Jack! What's doin'?"

"Hi, Tim. Just checking about tonight. You'll pick me up?"

"Sure, Jack. I was just preparing my cameras. Got yours ready?"

"Yep. It's in good working order and I got some photos to show you!"

"Great! See you about quarter of eight!"

After he hung up the phone Jack went back down to the dark room to see how his photos came out. When he looked at them he was very pleased with the results as he managed to get some revealing shots showing his mother's tits and Tim's rampant cock. He was especially pleased with the final shots showing Tim coming on Maria's back. One shot captured some cum in mid-air and was spectacular! He made two prints of each photo, putting one set in an envelope to take with him to the meeting and locking the other set together with the negatives in his filing cabinet. He went back up to his room to do his homework, but before he had finished the phone rang. He was delighted to hear Angela's voice!

"Hi, Angela! I was looking for you today."

"Were you really, Jack?" she replied, sounding surprised.

"Sure! I had a good time with you yesterday, and I wanted to see you again."

"Really? Most guys don't bother once they've got what they want. Anyway, I wasn't at school today as I badly twisted my ankle last night."

"Sorry to hear that, Angela. Are you feeling better now? Gonna be at school tomorrow?"

"No, I conned a three day note from the doctor, so I'm not coming back until Thursday. Why don't you come by after school tomorrow?"

Jack considered this for a moment and it occurred to him that at the very least this could be his chance to get his trophy-panties from her! "Great! I'll do that!"

"OK, see you then! Bye!"

Jack went back to his homework and finished it by seven thirty, in enough time to get ready to go out. He got ready then went downstairs to watch TV while waiting for Tim. Eight o'clock came and went but still Tim hadn't come for him yet. Another fifteen minutes passed and then he decided to call Tim to see if he was still home. He got up to use the phone, but it rang before he could get there. Tim apologized for being late but his car had broken down, so Tom would pick them all up in his van and then they'd go directly to their target.

It was almost nine before Tom's van stopped outside Jack's house, honking the horn loudly. Jack raced outside and got in the back with Jeff and Jim, with Tim up front with Tom.

"Hey guys! I thought you'd forgotten me!"

"No, we wouldn't do that, Jack," Tim said. "Especially since you've got something to show us. You remembered to bring your camera?"

"Sure," Jack said, patting the tote bag in his hand. "I've got everything here!"

"Great!"

"So we're going to check out a chick now, Tom?" Jack asked.

"Right, Jack. I think you all know Lana?"

They nodded as Lana was well known to all the guys in school. She was in the senior class and probably the best looking of all the senior girls, with long blonde hair and impressive tits. Tom took them to a three-storey apartment building and explained, "My uncle lives in this building and there's a great view of Lana's bedroom window from his balcony. It seems like she usually goes to bed at nine thirty, so we should be just in time."

"Is your uncle home?" Jeff asked nervously.

"No, he owns a restaurant, so he's out every evening. He gave me a key so I sometimes come over here to do my homework."

They went up to the apartment and true to his word, Tom showed them Lana's window which was directly opposite the living room balcony. Tim got his camera out and clipped on the big telephoto lens, while the others got settled on the floor, watching the window of the house opposite to them. As if on cue at exactly nine-thirty a light came on in an upstairs room and Lana came into the room, wearing a short skirt and white blouse. The room was brightly lit and the window was large and open so that the boys could see almost the entire room.

"This is a perfect spot!" Jim said, excitedly.

Lana turned her back on the window and then dropped her skirt to the floor. Next she pulled off her blouse and they could see she was now only in her bra and panties. As she turned back to look in the mirror, the swell of her beautiful tits was clearly outlined.

"Shit!" Jim exclaimed. "She's got great tits, eh? I gotta get this on tape!"

They all murmured agreement as Lana leaned forward slightly as she reached behind her back to unclasp the bra and they all sighed as her luscious orbs swung free of the boob-sling. Lana briefly rubbed her breasts before turning again to pull off her panties As she pulled them down, Jim put on the telescopic lens on his video camera and started shooting. Lana slowly lowered her panties and stepped out of them, kicking them in a high arc onto the bed. Her hands fondled her body and her nipples grew hard as she massaged her tits. She bent forward and brought one tit up to her mouth so she could suck the nipple.

"Fuck! That's hot!" Jeff yelled out, rubbing his dick through his pants. "I'm getting horny just watching!"

"Shut up, Jeff! Just watch for now."

Lana dropped a hand down to her pussy and slowly inserted a finger into her cunt, then started stroking in and out. She seemed to be breathing harder as her hand went faster. Finally, she lay back on the bed and used one hand to hold her pussy open while she used the other to stroke her clit. All this time Tim continued taking shots of the action with his camera, while Jim had his video camera going.

"With the open window and good light, these are going to be great pictures!"

After a couple of minutes, Lana reached her climax as her body shuddered from the pleasure as she bit her lower lip during her orgasm. After a while she got up and went, still nude, into the bathroom closing the door behind her.

"Wow," Jack said, "That was really something! Is it usually like this?"

"No, we're not always this lucky," Tim admitted. "And maybe we're not finished yet!"

After a while Lana came back into the room, still completely nude, and started drying herself off, with Tim and Jim both busy with their cameras. Then she reached in her drawer and pulled out a pair of fresh panties, put them on and then threw a kiss right in their direction! She put her nightgown on, and then closed the window and the drapes.

"I guess that's it for tonight, Tom?"

"Yes, I think so."

"Do you think she knew we were watching?" Jeff asked.

"Probably," Tom said. "The last time I watched her she did the same thing, but tonight was better, because she only stripped that time."

Jack said, "Well all I can say is she's really stacked!"

"You know what, we should go over there and gang bang her!" Jim suggested.

"No, don't say that!" Tom said. "I've watched her for weeks and she always does something like that. I'd never seen her frig herself off like that, though. Anyway, she's going out with me on Saturday."

"Are you laying claim to her?" Tim asked.

"Yes, I am."

"OK, she's yours, but you gotta see if you can get some better picture for us, OK?"

"OK, Tim."

"OK," Tim said, "Is everyone horny after that?" They all nodded yes and Tim went on, "We were going back to Jeff's house, but I've just had an idea."

"Go on," Jack said.

"Tom, what time do you think your uncle will be home?"

"Oh, not until after midnight."

"So we have a couple of hours?"

"Sure, why?"

"Well, I think Jack has something to show us and then we have to initiate him into our brotherhood, so I was thinking we could finish our business here, if you think it's OK?"

"Yes, I reckon so."

"OK, then. So, Jack, what you got?"

Jack said, "I've got some great photos to show you. If you're not horny now you will be after you see these!" So saying, he took the pictures out of the bag and spread them out on the table.

They all gathered round and oohed and aahed at them. At first no one realized who the couple in the pictures were until Tim suddenly said, "Jack! How did you get these?"

Jack replied calmly, "I took them myself yesterday!"

"How? I didn't think you were home!"

"I was out until about five, and when I came home I saw my mother sucking your dick! I raced upstairs to get my camera and captured the rest of the action on film!"

"So you just stood by and watched me fuck your mother?"

"Sure. It was only fair. After all I fucked yours!"

Tim looked at Jack for a moment and then laughed out loud. "Jack, you dog! Give me five!" They high-fived and then Tim said, "I guess that makes us brothers for life!"

"I guess it does!"

The other guys were laughing now, but still looking at the photos with great interest.

Then Tim said, "OK, guys. Listen up! This is the first night for our newest member, Jack, who has already proved his worth to our group by an excellent piece of snoop camera work!" Everyone cheered this remark and Tim went on, "So if y'all are ready we'll have our usual initiation jerk-off ceremony, OK?"

Tom, Jim and Jeff all nodded their heads in agreement, while Jack looked on, somewhat puzzled.

"OK, Jack, it's quite simple. You have to jerk each of us off in turn and then we take turns at you until we get you to cum. OK? You ready?"

Jack nodded but doesn't say anything, feeling a little nervous, not having done anything like this before, but just going along with their program.

Tim went on, "OK, guys? Pairs or singles?"

Tom said, "Since we're a bit later than usual, let's do it in pairs, OK?"

"OK," Tim agreed. "So, Jack, that means you jerk off a cock in each hand, OK?" Jack nodded again, and Tim continued, "Alphabetical or reverse?"

Jim suggested, "Let's toss a coin. Heads means alphabetical!"

"All right," Tim agreed. "Heads means Jeff and Jim first, Tom and me second. Jack, got a coin?"

"Sure," he said, pulling a quarter out of his pocket.

"You toss it and let it fall on the floor," Tim instructed. Jack did as he said and then looked at the coin as it came to a rest. "It's tails!"

"OK, then it's Tom and me first, then," Tim announced as he started pulling off his clothes, indicating for the others to do the same. Within a short space of time, all five guys were naked and Jack saw that everyone's cock was hard and bobbing about. What he heard next astounded him. Tim went on to say, "Oh, I forgot one detail. As you jerk us off each guy shoots his cum into your mouth! You can swallow it or spit it out, whatever you want. Then when we bring you off you shoot into a glass and we all take a taste, fair enough? OK, guys?"

Tom said, "I've a better idea, Tim. My uncle's got a stash of condoms in his bedroom, so if Jack puts one on we could catch his cum in it."

"Great idea, Tom. If you're ready, Jack, lie on the floor and we'll take our positions."

Jack was almost stunned at this new development but he followed Tim's instructions and lay down on the carpet, while Tim and Tom knelt on either side of his head, their hard pricks swaying over him. Jack reached up and took hold of a cock in each hand. He started slowing jerking each one, Tim's in his right hand and Tom's in his left. Of course he had seen all these guy's cocks before at the party when they all gave Suzie a cum-bath but now he was able to see them more closely. Tim's was about seven inches long and quite thick, while Tom's didn't seem quite as long but it was thicker with a big bulbous head. Jack started moving his hands faster and both guys moaned as they threw their heads back in pleasure.

Very soon, Jack heard Tim moan, "I'm coming, Jack! Open your mouth!" Jack did so, and pulled Tim's cock closer to his mouth. Within seconds, he felt Tim's hot cum splatter over his cheek and then another burst fell into his waiting mouth. He continued jerking Tim's cock until the stream subsided. He couldn't help swallowing the cum in his mouth which tasted slightly salty but wasn't unpleasant. After Tim had finished, Jack turned slightly to his left side so he could grab Tom's thick prick with his right hand. He started rapidly jerking it and was soon rewarded with another load of cum splattering on his face, a little bit of which fell on his lips, which he licked off with his tongue and swallowed.

When Tom finished spurting his load, he got up and then Jeff and Jim took their places on each side of Jack, holding out their dicks to him. As he grabbed each of them Jack noticed a bigger difference between these two than there was in the other two. Jeff's was the shortest of them all, probably no more than six inches, but it was quite fat. Jim's was long and thin, and seemed to be longer than any of the others. Jack started jerking Jim's dick with his left hand and then started fisting Jeff with his right. He was now getting the hang of using both hands and before long both guys are moaning with pleasure.

Jim panted to Jeff, "I'm nearly there, buddy. How about you?"

"Yeah, yeah, I'm gonna cum soon."

"Let's give Jack a thrill and cum together, OK?"

"OK, I'm there now!"

"Me too...oo...oooh!" Jim gurgled as his long hose erupted its hot load all over Jack's face with some spilling into his waiting mouth. Jeff's followed right away and proved to be the most accurate with the majority of his ejaculate going directly into Jack's throat, and he had no choice but to swallow everything in there.

Just as Jim and Jeff got up off their knees they heard a door slam.

"Hell, what was that?" Jeff asked.

"Sounded like the front door," Tom said, "but it's way too early for my uncle to be home."

"Who is it, then?" Tim asked, now back in his underwear.

Before Tom could reply the door opened and a middle-aged woman wearing a black dress came into the room. She seemed as startled to see the naked boys as they were at her sudden unexpected entrance into the room. Even though she had salt and pepper hair and was wearing glasses, there was still something about her that was sexually attractive. She stifled a scream and then managed to blurt out, "Who are you? What are you doing here?"

Tom was the first to recover, having pulled his under shorts back on, "My uncle lives here, and he gave me a key. Now what's your story? What are you doing here?"

"I'm the housekeeper! I think you'd better go home!"

"No, not yet. What are you doing here at this time of night?"

She didn't answer right away but just stood there looking blankly at them.

"Come on, we need to know. Did you come back for something? Did you come to steal something?" She turned to leave, but Tim was standing in her way.

"Not so fast, lady," he said gruffly. "We can't let you leave now. If you won't tell us why you let yourself in, we're going to call the police. We have to know why you're here, er, what's your name anyway?"

"My name is Elizabeth, sir. Look, I can't tell you exactly why I'm here, but Mr. Major told me to be here before he came home tonight, so you ought to call him before you call the police!" She looked around the room at all of the guys, two in just their underwear, two completely naked and a fifth lying naked on the floor with a huge hard-on. "What are you guys doing anyway? Why are you naked? Are you having an orgy?"

"Well now, Elizabeth, that's another reason we can't let you leave," Tom interjected. "You've seen too much! You're probably going to tell my uncle everything you saw, aren't you?"

"No, if you leave now, I won't say anything."

"Why should we trust you?"

"You have my word on it."

"No, we can't take that chance. We've got to have something that will guarantee your silence."

"Like what?"

"That's a good question."

Jeff piped up from the other side of the room. "How about some naked pictures?"

Jim laughed out loud, "Or even a video!"

"Good thinking, guys!" Tim said. "So how about it, Elizabeth? You look like you have some nice curves underneath that dress. Show 'em to us and we'll leave you alone, OK?"

"No! No way! You've gotta be kidding!"

"Not at all, Elizabeth, we're deadly serious. Unless you have a better idea?"

"Leave me alone and I'll not tell anyone what I saw. I'm not sure what I saw anyway!"

"Naw, it's not that easy. We gotta have something on you, and the easiest way is take something off you." Tim replied. "Now look, we mean it. Either you take off your clothes or we'll strip you naked ourselves, right, guys?" The others murmured their assent and Tim continued, "So there you have it, Elizabeth. It's five against one. Your choice, the easy way or the hard way?"

Elizabeth looked at each of them in turn and saw they were deadly serious. She shrugged her shoulders and said, "OK, how about if I just take off my dress?"

"All right, that's a start. Come into the middle of the room so I can get a good camera angle." Elizabeth slowly moved to the centre of the room in front of the couch where Tom, Jeff and Jack had moved while Tim and Jim got their cameras ready. Jack was the only one still naked and his cock was as hard as steel at the anticipation of seeing this mature woman undress, something he had never experienced before.

Elizabeth slowly reached behind her back and unfastened her dress, then shrugged it off her shoulders, letting it fall to the floor, exposing the fact that she was wearing all black underwear. Her huge boobs were hardly contained by a full bra, and the lower half of her body was encased in a girdle with a black suspender belt securing black stockings.

"Very nice, Elizabeth, very nice," commented Tim. "Now could you please turn around, so we can see your butt?" She obeyed and the boys were delighted to see that her ass was pretty firm and nicely shaped. "OK, now back again, please." Again she obeyed.

"Now that is very nice, Elizabeth, but I think the boys need to see more of your boobs. Please remove your bra for us."

Elizabeth shot a look at him and replied, "Look, I never...."

"Remember, Elizabeth, the easy way or the hard way?"

Without any further argument, Elizabeth reached behind her back and unfastened her bra, but still held it in place by crossing her arms over her chest.

"Come on, Elizabeth," Jeff cajoled, "we know they're big and beautiful, so just give us a peek!"

Elizabeth sighed, and released the pressure on the bra, letting it fall to the floor, but still hiding her breasts with her arms.

"Great, Elizabeth, you're doing good," Tim encouraged, "now put your hands on your hips, so we can see those beauties, eh?"

Elizabeth rolled her eyes upwards, as if looking for divine intervention, but when none came, she resignedly dropped her arms and placed her hands on her hips as instructed. Now the boys could see her huge pendulous breasts and they all moaned with pleasure.

"Holy cow," Tom exclaimed. "Just look at those knockers! They're the biggest I've ever seen!" None of the others said anything, but their reaction was fully evident by the tents in their shorts. Everyone that is except for Jack, who already being naked, was gently stroking his hard cock.

Elizabeth was looking over at Tim, no doubt waiting for him to say she'd shown enough, but she was out of luck with that, for then he suggested she sit down on the easy chair so she could roll off her stockings. She detached the stockings from the belt and then unfastened the belt from her body. She sat down and then slowly peeled off the stocking from first the right leg and then the left, dropping them on the floor alongside the rest of her clothes.