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Introduction:

An old friend needs some help. NOTE: If you negative rep the story, please leave a comment saying why, that way I can improved my writing so that everyone can enjoy the stories!
It had already been a week that me and Cynthia were together. We were now roommates sharing my small house. Over the course of the week, we fucked like rabbits. In the kitchen, in the shower, on the couch, everywhere. Name a place in my house and chances are we had sex there. Things weren't all fun and games though. Cynthia was determined to stay away from her family. She still wouldn't tell me what happened that night she showed up on at my door, though I've made some guesses since then. It didn't seem to be that big of an issue, as neither side was doing much. I suppose they just fell out. I wasn't going to complain. The past week was easily the best week of my life. Little did I know, the next one was going to be even better.

Cynthia and I were grabbing lunch at some burger place when she received a text message. She read for a bit, then looked at me and said “Cass wants to do something tonight. The old gang. Are you down?” Cassandra was Cynthia's best friend and another good friend of mine. I had a crush on her back in my senior year of high school. At 5'7, she was slightly larger than Cynthia, but definitely not overweight. Cassandra was pretty average actually. Brown eyes, dark brown hair, regular skin tone. Still, she wasn't ugly at all.
“Sure,” I said. “Where to?”
“That's the thing. We don't really have a place right now.” Cynthia bit her lip.
“Why not our place? We'll just...clean up a bit.” Thinking of all the times we had sex around the house, there was bound to be some signs somewhere. Those would need to be cleaned up.
“Alright, I'll let her know.”
We picked up our trays, tossed out our garbage and left the restaurant. When we got home, we started a massive cleaning operation. There weren't as many sperm stains as I thought there would be. Must be because Cynthia was very keen on not letting any of it go to waste. On the other hand, there were bits and pieces of clothing strewn everywhere. After an hour or two, we got the house into tip-top shape. “Jeez,” I said, “I've never seen my house this clean.” Cynthia laughed.
“Well...we could mess it up a bit,” she said mischievously.
“Cyn, we just cleaned up.” I smiled at her. Leaning in, she gave me a kiss. “well...I suppose we could always just clean up again.” I returned her kiss. One of her hands was rubbing my back and the other was rubbing my cock through my jeans. I grabbed her ass, played with it a bit, then moved up to her breasts. She started to pull off my shirt. I lifted my arms. She took my shirt off and tossed it onto the floor. I then returned the favor, lifting her shirt off. She started working on my pants. Getting them unzipped, she pulled my cock out of my boxers and started running her hand up and down it.
“Mmm...looks like you're nice and hard huh?”
I responded by taking her head and moving her toward my dick. She started to suck on it, swirling her tongue around the head. As she took it into her mouth, she used her tongue to rub the underside. She was still using one hand on my cock while she was sucking on it. With her free hand, she played with my balls. I don't know where she got this kind of experience, but Cynthia knew exactly how to get a man going. It was like magic. All she needed to do was touch you and you'd be dying to cum. I stopped her before I reached my climax though.
I grabbed her around the waist and tossed her onto the couch. “Ooo...” she purred. I pulled her pants off. I ran a hand lightly along her inner thigh. I avoided her pussy and continued lightly on her other thigh. When I reached the end of her thigh, I went back and rubbed her pussy gently through her panties. Her panties were pretty sheer, so you could easily see her tattoo and pussy lips through the fabric. The juices flowing from her pussy also made it easier to see. I started to circle her entrance with a finger, running it around ever so lightly. I could tell it was driving her mad. I just barely touched her clit as I passed it, then continued onwards. “Stop being such a tease!” she pleaded with me. Hearing this, I pulled off her panties, exposing her completely. I slowly slid one finger into her pussy. Always moving slowly, I pulled it in and out. Cynthia started moaning softly. I added another finger. I started to speed up the pace.
Her moans were getting a bit louder now. I used my thumb to rub her clit as I fingered her. She started squirming and panting. I could tell she was nearing her orgasm. I stopped just shy of letting her cum. “Not yet,” I said, “I want to try something out first.” I slowly pumped in and out, ignoring her clit. I went so slowly, it was agonizing for her. I could see in her eyes her pleading with me, begging me to cum. “I think you're about ready. Do you want to cum?”
“Yes! Please, please make me cum!”
“Alright then, I'll make you come. Spread your legs nice and wide.” She did just that. I placed my free hand on her pelvis, pushing downwards. I slid my middle finger and ring finger into her pussy, then curved them upwards, feeling around the wall. As I passed a certain point, I heard her give a loud moan. Knowing I found the right spot, I started to violently finger her, moving my hand up and down, forcing my fingers to push into the spot over and over again as quickly and forcefully as possible. A wet slapping sound was just barely audible over her loud moans.
“Oh god, oh god, oh fuck, oh fuck, FUCK, FUCK, FUCK!” She screamed. I just continued, feeling a pressure building up in her pussy. She wasn't making a sound anymore, just mouthing the words “oh fuck” over and over again. Feeling her hit her orgasm, I pulled out of her. She squirted a good foot outwards with plenty of force. Her entire body spasmed so much I had to hold her down. “Oh my god...fuck...that...that...” She couldn't form a sentence.
“Did you enjoy that?”
“Ye...yes. Wow...I've never cum so hard in my life. I didn't know I could even squirt. I thought that stuff in porn was just fake.”
“Heh, nope, not all of it is fake.” I held out my hand to her. She took it and licked her juices off of my fingers. “How do you like the taste of your pussy?”
Licking her lips, she answered “Delicious”. I saw that she was eyeing my cock. It was still hard, especially after that extremely sexy orgasm of hers.
“Do you want my cock in you?”
“Yes.”
“Do you want me to fuck you?”
“Yes!”
“I want you to beg for it.”
“Please Jack. Please fuck my pussy with your huge cock!”
I decided I teased her enough. I took some time to slick my cock with her juices, then I lined it up with her pussy. I then thrust into her as deeply as I could, all of a sudden. She gasped as I pushed in all the way to the base of my cock. I then started to fuck her hard and fast. She gasped and squealed, holding my ass and pulling me forward, trying to get me deeper. I just slammed into her as hard and fast as I could. Her cries were getting louder and louder, and I felt her pussy start to tighten up. I could tell she was nearing an orgasm again. I kept my furious pace, even when she hit her climax. Her body spasmed and jerked, and her hands tried to push me back, but I kept plowing into her until she came down. I pulled out of her and said “Suck on it. I want to cum in that pretty little mouth of yours.” She obediently raised her head and started to suck my cock. She used her hands to help as well. I hit my climax, shooting off into her mouth, where she swallowed every last drop. “Oh...wow...that was good...” Cynthia panted.
“Heh, now we gotta clean up.”

A couple of hours later, after everything was taken care of, the doorbell rang. Opening it, I saw Cassandra standing on my porch. “Oh my god! Jack!” She squealed. She threw her arms around me, saying, “I haven't seen you in forever! What have you been up to?”
“Oh, a little of this, a little of that.”
“You sly dog,” she said, smacking me on the shoulder. “What's this about you and Cynthia shacking up? I always thought you two would be good together!”
“Really? I seem to recall something very different back in school.” At this point, Cynthia showed up to greet out guest. Amid all the pleasantries I led Cassandra into the living room to take a seat while we waited for the others. As I was getting some snacks, I asked “So who else is coming?”
“Oh, the old gang. Sam, Mass and Milly.” Cass answered.
The old gang. Samantha, Massimo and Melinda. We used to be a slightly bigger group, but the others lost touch with us over the years. We've all been busy doing our own thing, but we keep tabs on each other.
“What about Mike?” Mike was Cass's boyfriend and while he wasn't really part of our group, he fit in well, so I was surprised he wasn't showing up.
“He...had other things to do,” was all she said.
“Are Mass and Milly still together?” Cyn asked.
“You mean you don't know? They're engaged! Mass proposed a couple of weeks ago!”
“What? I didn't know that! Jack, what about you?”
“I...er...sorta knew.” It's true. I was asked to be the best man. “I'm the best man.”
“Why haven't you told me?” Cynthia fumed.
“Calm down, they were probably waiting to tell you tonight.” Cassandra said. The doorbell rang. I got up and went to answer. Opening the door, I saw Massimo and Melinda standing there smiling.
“Speak of the devil! Come in guys!” I led them to the living room. Massimo was my height, slightly smaller, yet more ripped than me. Melinda was tiny, very much so. Not height wise, but she was extremely slim. This only accentuated her long legs and neck. Man, did she have a nice heart shaped ass. Her hair was cropped short, ending just at her jawline. Mass was lucky to get a catch like her. I left them in the living room and went to grab some more food from the kitchen. While taking stuff out of the cupboard, I heard someone walk through the door. Looking up, I see Mass smiling.
“Dude, it's about time you and Cynthia got it going. I kept telling her that she should date you, but she never listened.”
“Heh, thanks buddy. Don't ask me how it happened, I'm still in shock.” We laughed.
“Seriously though. I know you haven't had the best luck with women, but this is definitely a turning point!” Oh how right he was, though he didn't know it. The doorbell rang yet again. I handed the food to Mass and went to answer. Opening the door, I led the last of the gang into the house. Samantha was about the same height as Cassandra. She was plumper than any of the other girls, but definitely not overweight. She had blond hair and green eyes. She easily had the biggest boobs of everyone, noticeably so. If I'd have to guess, I'd say solid D cups. She also had a nice bubble butt. Giving each other a hug, we walked into the living room, where pretty much every seat was occupied now. We spent some time talking, laughing, reminiscing and generally just goofing around. We're actually a pretty boring group. Really. We played Scrabble for hours. Admittedly, we managed to make it seem much more exciting with all our “Ha!s” and “Take that!”, but that doesn't change the fact that we play Scrabble.

Time passed and eventually people had to leave. Sam was the first to go. She had a cousin's wedding the next day so she had to get up early to prepare for it. Mass and Milly were next, leaving Cassandra, Cynthia and myself. We started cleaning up. Cass and Cyn were speaking in whispers. I noticed them, but didn't say anything. “Hey Jack...I got an idea for a game we can play,” Cynthia called to me from the living room.
“We're only three people Cyn,” I answered back.
“That's fine. Come in the living room and I'll explain the game.”
I put away the last of the leftovers and walked into the living room. Seeing what was waiting for me, I actually stopped and my jaw dropped. I couldn't think straight. I didn't know what was going on, but I did know that I was looking at Cynthia and Cassandra, both completely naked. “Wha...Who...How...I...” I couldn't even speak properly.
“Hmm, I think he likes what he sees,” said Cass playfully, eyeing my swiftly growing erection.
“That he does. Although Jack, you're breaking the rules of the game. You can't be wearing any clothing.”
“Woah, woah woah. Cassandra, don't you have a boyfriend?”
“Yes, so?”
“I can't...I won't get between you two.”
“Come on Jack, she won't tell, niether will I,” Cynthia purred, pressing herself against my back and rubbing my cock with her hands.
“Yeah. Mike hasn't been satisfying me lately and what Cynthia's told me about you two was so hot, I had to get in on it.” Cass was now rubbing my cock too. Cynthia started to pull off my shirt while Cass tugged on my pants.
“Come on, I can't...” I started to speak, but Cynthia silenced me with a deep kiss. Now stripped down to my boxers, with two hot girls fawning all over me, I just couldn't resist anymore. I reached down and grabbed Cassandra's C cup breasts.
“Oooh!” She squealed as I tugged and tweaked her nipples. Cynthia kneeled down and pulled off my boxers, exposing my now rock hard cock. “Wow, Cyn, you weren't kidding! He's at least two inches bigger than Mike! And wider too!” Cassandra's eyes seem to light up at the sight of my dick. She started to sucking on it. Cynthia moved lower and sucked on my balls.
“Ugh, slow down, you two! You want me to last long enough to fuck you right?”
Cass just gave me a puppy dog look. “Please can I suck on your cock longer?”
“...fine.” How could I resist that? Reaching down, I played with Cynthia's breasts this time. She gave a small moan, placed one hand on Cassandra's breast and then started sucking on the other one. With her free hand, she rubbed Cassandra's pussy. Cass was moaning around my cock. Cynthia switched to sucking the other breast, using her hand to play with the one she had just finished with.
“Alright, kneel on the couch, both of you,” I said. They both got up, kissed each other, then followed my command. “Spread your legs a bit, I want to get a nice view.” Boy, did I get a nice view. With their ass cheeks being spread slightly, I clearly saw their pretty little pussies. Cynthia's smaller, tanned ass next to Cassandra's bigger, paler ass. It was driving me mad, I was so horny right then. I placed myself at Cassandra's pussy entrance. Rubbing my cock against it a couple of times, I said to Cyn “Spread your pussy juice over my dick so I can enter Cass.” Cynthia complied, putting her fingers in her pussy then running her hand back and forth over my cock. I lined up, then thrust into Cassandra's pussy. She gave a loud moan at this. I started to fuck her, pumping in and out. Cynthia kissed Cass and continued to play with her breasts, kneading them and squeezing.
Reaching over, I pushed three of my fingers into Cynthia and started to finger fuck her. She responded by moving her hips and moaning loudly. Cynthia moved one hand down to rub her clit and used the other hand to rub Cassandra's clit as well. Still kissing deeply, Cass gave a little yelp when she felt Cyn touch her clit. As I continued to fuck Cass, I smacked her ass a couple of times, leaving a red handprint. Her breathing started to quicken, I felt her pussy tightening, sucking me in with every thrust and her hips were moving extremely quickly now. She broke off from the kiss with Cynthia to moan loudly as she came. “Ahh, Ahh, Ahh, AHH, AHH, AHHHHHHH!!!!!!!” Her pussy tighten up considerably, making it hard for me to keep thrusting. Instead, I increased my pace on Cynthia with my hand, forcing her to reach her climax as well. I was fingering her extremely hard as she came. Cynthia arched her back and stuck out her ass during her orgasm, rubbing her clit furiously.
“UUGGGHHHH!!!! GOD!!!” Cynthia screamed as she came. Pulling out of Cass, I ordered her to suck my cock. She complied, smiling as she licked it clean.
“How do you like the taste of both your pussy and Cynthia's pussy?”
“Mhmm,” she moaned, still with my dick in her mouth.
“Cynthia, lie down and spread your legs nice and wide. Cassandra, I want you to stand over her with your legs spread wide as well.” The two did as I asked. I placed my cock at Cyn's pussy and stabbed in.
“Ah!” Cyn moaned. Sitting up a bit, she started to suck on Cass' breasts. Cass in return, reached down and pinched Cyn's nipples. I leaned forward and started to lick Cass's pussy.
“Ooooo...” She purred. I used my hands to play with her ass, kneading and molding it the way Cynthia was doing to her breasts. I was still fucking Cynthia and Cass was still playing with Cyn's nipples. Both girls were panting now, moaning loudly. Cassandra hit her climax first. “Oh god! UGH! FUCK!!!” Her body jerked and spasmed, though me and Cynthia continued to pleasure her.
Cynthia came almost right afterwards, moaning loudly while still sucking on Cassandra's breasts. Her body arched forward, pushing her hips up and my cock deeper into her. Her pussy felt like it never wanted to let go of my dick. I was getting close too and I marvelled at how long I lasted, given how hot this was. “I want to cum on your pretty faces,” I said. Cass and Cyn kneeled down and started giving me a handjob to help me finish. I came pretty quickly, shooting sperm across both their faces. Once the last few drops had been shot, they turned to each other to look at their splattered faces. Smiling, they both licked each other clean, moaning as they did so. That might have been the hottest part of the night, where they both enjoyed a meal of my sperm off the other's face. “Well Cass? Are you satisfied?”
Smiling at me, she kissed Cynthia one last time before answering. “Yes, very much so. Can I count on you and Cynthia next time I need to get off?”
“Of course you can.” I smiled and kissed Cass. “As long as nobody finds out.”
“Deal.”
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