Four Friends Ch. 05

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A sister is added as well.
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Part 5 of the 6 part series

Updated 06/10/2023
Created 09/03/2020
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Manny2314
Manny2314
708 Followers

Editor's note: this story contains scenes of incest or incest content.

*****

"Annie, did you know Bill Jackson in school?" Chrissie asked her sister the next day.

"Billy?" she said. "Sure, I knew Billy. He was a very sweet guy."

"You mean - he was gay?"

"Oh, no," Annie said. "He wasn't gay. I didn't mean that kind of sweet. Just really nice. Quiet. Shy. You know?"

"Did you have sex with him?" Chrissie knew that her sister was no virgin, but she didn't know who she had had sex with. Well, not all of them.

Annie actually laughed at the thought. "No, I never did. I honestly doubt if he ever did it with anyone. He was really shy. Like - painfully shy. I don't know if he ever had a date. Of course he might have without me knowing it - I wasn't that close to him. But I probably would have heard. Why are you asking so much about him?"

Chrissie wasn't sure how much she should say, but she intended to tell the truth. "He's working for a pizza place, delivering. That's how I met him."

"And you're asking a lot about sex."

"No, we just got off onto that. Besides, you know I am always interested in sex," Chrissie giggled. "Just like you!" They both giggled.

After giggling a bit longer Chrissie got more serious. "Annie, speaking of sex, have you ever seen someone have sex? Or has someone watched you?"

"What?" Annie wasn't shocked. She wasn't shocked at much, especially from her sister. But she was surprised. "No, never did either. But, how about you?"

Chrissie looked over at Annie. "Yes," she said softly. "Yes, I have. Both."

She waited for Annie to be surprised, but she looked more interested in details than she was surprised.

Chrissie asked her, "Do you think you'd like that?"

"Which one?" Annie asked, but before she got an answer she continued. "Doesn't matter. I think they both sound exciting. Very exciting. Have you really done it?"

"Yes." Chrissie knew she would have to share details, so she said, "Last night I watched Riley and Bob screwing. It was so exciting."

"Oh, shit!" Annie said. "Really? They just did it for you to watch?"

"Well, they were doing it anyway. Not just so I could watch."

"Did they know you were watching?" Annie asked, very interested.

"Oh, yes, they knew. Tony and I were both watching."

Annie thought for a minute, then, "Did they watch you and Tony screw?"

Chrissie hesitated. "Well... yeah, they did."

"Oh, Holy shit!" Annie said. But she was smiling. And intrigued. "How did it make you feel?"

"Oh, fuck. It was so - sensual. Somebody actually watching me take a big dick right up inside me. It made it so much hotter. I tried watching their eyes. It was somehow a little like watching myself. But more."

Annie was breathing hard. "I did notice that you said BIG dick, but I really wonder - wasn't it weird?"

"Oh, yeah. It was at first. But it didn't last long. So many thoughts... it's hard to explain."

Looking at the excitement on Annie's face, Chrissie wanted to ask, "Do you think you would like it?"

Annie breathed hard. "It sounds so great. I'm getting hot just thinking about it."

"Well, maybe..." Chrissie stopped talking, but Annie urged her to continue. "Maybe, you know, you could join us sometime. Somehow."

Chrissie wasn't sure how Annie would respond. She thought Annie was excited by the thought, but actually doing it? And of course, if her sister was there it might be totally strange.

Annie didn't disappoint. "Fucking shit! That would be so fantastic."

Chrissie appraised her sister. "You must be wilder than I thought."

"I am. And I believe you are as well!"

"What about Bill?" Chrissie asked.

Annie was puzzled. "Bill? Who is that? Oh, you mean... Billy? Jackson? Oh, no, just about anyone else would be better than him. I mean, he's cute enough, but he is too shy for anything like that."

Chrissie spoke quietly again. "Would you believe - last night I blew him? I gave him a blow job right there in front of everyone."

"What? I don't believe it. Billy?"

"Well, actually he didn't know we were being watched. But I did blow him. And he enjoyed it!"

Annie was still in disbelief. "I'm sure he enjoyed it. Probably his first one. But I am really surprised."

"I guess maybe you could see for yourself!"

"What???" Annie straightened up and looked her in the eye, ready for details. "What are you talking about?"

"Just keep next Friday open," Chrissie said.

By Friday the others had agreed, and there were some general plans in place. They called the pizza place and talked to Bill. Not surprisingly, he was happy to bring a pizza by, and make sure it was his last delivery. Though it was pretty early for his last one, he didn't care. In fact he was eager.

"Hi, Bill," Chrissie greeted him. She was topless behind the door, just like before, but this time Bill wasn't surprised. In fact he was relieved. He could hardly dare to hope that this could be happening again.

"What were you expecting tonight?" She asked him.

"Uh - what? - nothing. Nothing."

She looked at him as she placed her hands on his chest. "Nothing? Surely you thought something might happen here tonight. Don't you remember last week?"

She was teasing him ferociously. She was also unbuttoning his shirt. "Let's take this off this time."

Chrissie sat on the floor and pulled him down with her, where she started kissing him. He kissed back, though he wasn't too good at it.

"You know my sister," she told him between kisses.

He looked surprised but couldn't answer. She told him who she was.

"Annie? Yeah. She's... she's... nice."

"You mean hot. Right?

"No, no, she's nice."

"You don't think she's hot?"

"Oh, yeah, she is," he said nervously. "I mean, she's nice, and, you know, yeah, she's pretty."

"You better say she's hot, 'cause she's here."

"What?" Bill stopped kissing and looked around. "She's here?"

"Hi, Billy," Annie said as she entered the room.

Chrissie had to hold Bill down to keep him on the floor or from covering himself up. He settled down in a few seconds and looked at Annie, dressed a lot sexier than she ever had been at school.

Chrissie said, "Remember that blowjob I gave you last week?"

Bill hid his face as much as he could, shocked and embarrassed.

"It's okay, Bill, Annie knows about blowjobs. In fact, she wanted to see you get one last week. She paused a moment. "Maybe she could watch us do something today."

Bill was shocked and confused, but still excited.

"Maybe you return the favor. Have ever seen a girl's pussy? Touched one? Felt one? Eaten one?"

Bill was moaning lowly at each suggestion. Then again when she told him that she was not wearing any panties.

"Lay back," Chrissie said quietly.

Bill was a good boy and did what he was told, only vaguely aware that something very sexual might be going to happen.

Chrissie straddled his naked chest, pulling her skirt high up above her waist, exposing her pussy to Bill's wide eyes. His very wide eyes. He couldn't believe that he was seeing a pussy for the very first time. And so, so close.

Then she really blew his mind by reaching her fingers down and pulling apart her pussy lips. He was staring at the inside of her pussy. Well, someone's pussy. He didn't care whose. It wasn't even registering. It was a pussy!

And it was getting closer! Chrissie was moving closer to him, to his face, her pussy moving in until it actually touched his face. His mind went blank. Until he heard a voice.

"Lick it." Chrissie said. "Stick out your tongue... and lick"

The good boy did as he was told, without thinking, and his tongue touched a pussy! He growled as his mind came back to life. He knew enough to move his tongue, up and down the slit that he felt. He was now aware of what unexpected pleasure he was having.

Then he saw Annie just to the side of them. She had removed her shirt, and was now taking off her bra. He strained to see her, Chrissie's body blocking part of his view. He strained to get a better view as her breasts were uncovered. Oh, how many times had he thought about those breasts. Not just hers, of course. Many breasts. And hers weren't the biggest by far, but she was really cute. And now that he could actually see them he loved them. They looked beautiful, no matter what size they were.

"Oh, Billy, yeah!" Chrissie yelled.

Bill had gotten so excited trying to look at Annie that he forgot what he was doing to Chrissie. His tongue got carried away with the excitement and had been attacked her pussy, driving deeper in between her lips. He was doing good without even knowing it.

"Bill, are you a virgin?" Chrissie suddenly asked.

"No, of course not." His voice was muffled, but was able to be understood.

Chrissie said, "Bill, be honest. It's important to tell me the truth. Are you a virgin?"

"Yes," he said quietly. Even his tongue lost some hardness.

"That's okay, Bill." Chrissie said, gasping a bit at the feelings coming from her pussy. "But tell me, do you want to stay a virgin or would you like to lose it?"

Chrissie lifted herself off his face just a little as she could not tell what he had just answered.

"Lose it!" he nearly shouted. "I don't want to be a virgin."

"Are you sure? Tonight? With us?"

He answered yes to each question through her pussy. At this, Annie removed her skirt and stood there in his view totally naked for a few seconds. Then she moved behind her sister to Bill's pants. She was quick to remove them and his raging erection bounced up into the air.

Annie took hold of his penis, feeling it, getting to know it. But not for long. She was anxious, too. She stroked it a few times and then, throwing her leg over him, positioned herself over top of it. She sank herself down onto it, pausing as it first entered her. She paused for her pleasure, but mostly for his. She was aware that it was a special time for him. And with his sister riding his face at the same time she was fucking him, it was truly special. He was constantly moaning, though it was muffled. He was very excited with each inch as he sunk deeper into his first pussy. The excitement overwhelmed him.

Behind the louvered door were the other three, doing their part in this orchestrated activity. It had gone just as they had planned. Perfectly. They watched as the two girls double teamed the poor pizza guy. Poor pizza guy? They all wished they could trade places. He will absolutely remember his first time, that was for sure! The girls were pleasuring him beyond any fantasies that he had ever had.

Chrissie had started first, but Bill was by far the most excited. He erupted with a scream, pumping up into Annie. She rode him, her pussy clenching his cock, both to milk him as well as trying to coax herself to explode, but she wasn't ready yet. She was quite disappointed. She had gotten so excited, but now he was done.

But Chrissie was ready for hers. Bill's tongue had reached far inside her, as his orgasm had caused it to stiffen and grow as much as his dick had. She pushed down hard on his face as she shook on top of him.

When she finished she thought of her sister, realizing that Bill had cum but Annie hadn't. That would disappoint her but with this crowd she would have at least one more chance before this evening was over. She rotated around on Bill to face Annie and was surprised to see her bouncing up and down on him. Chrissie even reached under her sister to feel Bill's cock. It was very stiff. His erection was driving into Annie as she kept dropping down, driving down, beginning to cry out herself. He hadn't softened after all.

Chrissie reached for Annie's clit and began rubbing it. Stroking it. She had never done this before, not with Annie, but she did not even wonder if she minded. Of course not. Annie was as oversexed as she was herself. It didn't take much between Chrissie stroking Annie's clit and having a cock stroking her insides in order to get Annie to erupt. As her climax hit she collapsed into Chrissie's arms.

When she was done, Annie allowed Bill's cock to slip out of her, waving proudly in the air, ready for more. Bill could certainly be happy with cumming once and losing his virginity, but both girls had cum, leaving Bill with little hope of cuming again. At least that's what he though.

Bill didn't know that there were three more people in the apartment who had been watching the whole thing and were now desperate for some relief of their own. They burst out from behind the door, already naked. They had been playing with each other, priming their bodies, waiting for their turn.

Bob and Tony were led out of the other other room by their cocks, Riley having a firm hold of them both. Tony stepped toward the left, where the others were, leaving Bob and Riley together. Bob led her a couple steps to the right, pinning her against the dining table then lifting her by the waist up onto the table. She sat on the edge and he pushed her onto her back, grabbing her ankles and spreading her legs. Bob stepped up between her legs, his stiff erection pointing the way. Letting go of one leg for a moment, he placed his head at Riley's entrance. When he had hold of both ankles again, with her legs spread as far as his arms could make them, he rammed himself home. Both made a groaning sound, in both excitement and relief, as he sunk deep into her on the first stroke. It was exciting as well as a relief, after all of the buildup they had had. He pushed in several times, getting their frustration out, before he was able to slow down a little and begin to enjoy the feeling of being inside her. They could also enjoy a little of seeing the other couples fucking.

Tony had headed straight for Annie. The 'new girl' had excited him as he had watched her fucking Bill, and he was hoping to get a chance at her. He had knelt behind her and pulled her hips up off the floor where she had fallen and wasted no time doing her doggie style. She supported herself with her arms while he held her by the hips and speared into her. She felt a little tighter than the girls that he had had lately, but there was no problem getting into her. She had just been loosened up by fucking Bill, after all.

Chrissie had fallen to the other side of Bill, who still had an obvious hard-on. Looking at him she had spread her legs and said, "Climb aboard, big boy." Her voice suddenly sounded extremely husky.

Bill had wasted no time crawling between her legs, unsure of whether he should use his mouth on her or his cock. She decided for him by lifting him upwards so they were head to head. As well as cock to pussy. At this point he let nature take over and settled his cock into her, driving it home. She locked her legs around him to help him thrust into her.

So all six people were now three couples, fucking away, with added inspiration by knowing, hearing, and somewhat seeing the other couples. Annie, still being fucked in the doggie position, had her head pushed near her sister's. They were close enough to kiss which, surprising to them both, they did. It was a very sexy, sloppy, passionate kiss, which they had never done before but felt so right at this moment. Chrissie also watched Annie's breasts bobbing back and forth underneath her. Chrissie's breasts were bigger, but she loved looking at Annie's. They were a perfect little mass of flesh. She couldn't resist reaching out and grasping one as it bounced, even pinching her hard nipple.

As Annie was getting fucked and played with, she was watching her sister get fucked by Billy. Shit, she thought, he has a really nice-sized cock. It wasn't the largest she had seen, but it was impressive. Certainly one of the biggest. She thought what a shame for Billy that the girls in high school hadn't known about it. Billy could have been pretty popular with some of her friends.

Annie was the first to explode. It had all been too much. The kiss with her sister helped, and feeling her play with her tit, and watching Billy's big cock enter her sister repeatedly, and of course being in the act of fucking Tony helped a lot. She had climaxed on Bill a short while ago and never had time to calm down from that. She, like her sister, was able to cum more than once in a short time. Someday they would try to find out how many times they could cum in a row, but tonight this would be enough. This one was a long, drawn out cum because Tony had been excited for a long time with no relief. He was ready to cum just a couple minutes after Annie, whom he kept right on fucking after she had finished.

Bob and Riley both erupted between those two, Bob driving hard again into her, still on the table. Her legs were getting sore being spread so far for all that time, but that didn't stop her from cumming along with him. He fell onto her, crushing her but not getting up until his softening erection fell out of her.

Bill was the last to cum. He had already cum once, inside Annie, but his cock remained hard under the circumstances. Even when Chrissie exploded he kept fucking her, unwilling to end this night when he had lost his virginity, then fucked his second girl immediately afterwards. Those thoughts running through his head were almost as exciting as his dick inside Chrissie. Well, the thoughts added to the excitement anyway.

Chrissie was happy to let him continue fucking even when she was done. She thought maybe she could cum again if Bill would last long enough, but she didn't think he would. And that was okay - she was pretty worn out by now. She was squeezing her vagina in an effort to help him end it soon. They were the only active ones left, which she liked, but no longer felt that much like putting on a show for the others.

Finally Billy rose to his climax. It wasn't as great as his first one. This one felt like it had to be pulled out of him, instead of exploding out. But it was still terrific! This had been such an incredible week. First was his first blow job and orgasm caused by someone other than himself. Now his first intercourse, no more virginity, and then even a second orgasm in a row. Could it get any better than this?

Manny2314
Manny2314
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