“Yes, please don't be mad,” Caleb said bracing for Ashley's reaction. “I know I shouldn't have … but when I walked in on you two I just couldn't turn away. And then Sara ...”
“Ash, I totally … I was my fault … I egged him on.” Sara said jumping in.
“I … I am truly sorry and I understand if you never want to see me again ...” Caleb said starting to get to his feet.
“You,” Ashley said looking at Caleb, “stay right where you are, as for you, Sara, get off me.”
Caleb sank back to his knees in disgrace and Sara rolled off Ashley's naked body and sat cross-legged at the head of the bed hanging her head in shame. Ashley sat up and looked at both of them as sternly as she could muster, until she finally burst out laughing.
“Sorry, sorry …” She said in between laughs, “but you pull a fast one on me and I think it's in my rights to make you both suffer a little. No one needs to be sorry, in fact, I'm thrilled to death. I mean as long as you are okay with this Caleb.”
“What? … I mean yeah, I guess so, I mean … What do you mean?”
“I just don't want you to think badly of me or Sara for what we do in the privacy of our own house. Sara had her Blooming Day a few months back and well one thing sort of led to another.”
“No, no, I mean I was a little shocked at first, but as long as it's mutual and no one gets hurt I have no problem with what you two do. Hell, you guys are closer to best friends anyway. She's an adult now, she can make her own decisions and if Sara wants to know more about her body and the joys of sex I have no problem with you showing her. ”
“What about you?” Sara asked hopefully.
Caleb looked over at her and then over to Ashley who smiled and nodded her head.
“I would love to help out if that is okay with Ashley.”
Sara looked over at Ashley who again nodded her approval.
“Sara has wanted to join us for quite some time now and while I didn't have a problem with it, I wasn't sure how you would react to such a request. But if you don't mind sharing our bed with Sara I certainly don't mind either!”
“Yea,” Sara exclaimed clapping her hands. “So can we start now?”
“Sure, what do you want to do first?” Caleb asked, his cock already back at attention.
“I want you to fuck me.” Sara said lustfully.
“Well, wow, okay … um, we can do that but maybe we can start a little slower.” Caleb said with a smile as he climbed up on the bed to join Ashley and Sara. “How about you just study it up close first, so you can get a good idea of what it looks like and feels like and how it works?”
“Okay!” Sara said.
Caleb stretched out on his back between the two of them, his hard cock standing at attention, while Ashley begin instructing Sara about the mysterious ways of the penis.
“Wow, it's so stiff, but sort of soft at the same time!” Sara said as she slowly played with her first real life penis.
Sara and Ashley were both on their knees next to Caleb, their beautiful asses staring him in the face as they played with and talked about his very happy cock. He couldn't resist reaching out touching their soft warm bodies and as his fingers began to stroke their tight firm butts they both stopped what they were doing and looked back at him with big smiles. Ashley had one of the best asses he had ever seen, small, tight, and almost perfectly round and Sara's was almost the exact replica only slightly smaller. In fact, even though they weren't blood related, Sara seemed like a mirror image of Ashley, same blue eyes and dark brown hair and same body type, average height, small waist and skinny legs. Ashley's large round breasts were the only thing really different as Sara's petite tits were smaller and more cone-shaped. Also, Ashley waxed her pubic hair while, at the time, Sara had yet to try that painful procedure, having to wax her legs was bad enough and she hadn't worked up the courage to do that to her pussy.
But the asses that presented themselves to him that night were amazingly similar and as Ashley was giving her daughter some tips on how to give a more effective hand job, Caleb worked his magic fingers, massaging their cute butts to their great delight. When Sara slipped his cock into her small mouth for the second time that night Caleb couldn't resist fondling her pussy for the first time. Sara's groans were muffled by his hard cock as he expertly worked on her gorgeous mound.
As Ashley could attest to, Caleb was much more than just a good lover, he was an expert. He studied everything he could find about the wonders of the female body and all the paths that led to its ultimate pleasure. His knowledge and skill translated well to Sara's teenage body and soon his fingers were dripping with her pussy juices. He easily slid his middle finger along her cunt slit, her pussy lips slipping along the sides of his finger as he gently rubbed up and down the entire length of her young wet cunt. He'd rest the tip of his finger just below her tiny asshole and then slowly slide it forward across her virgin opening stopping for a quick rub against her little clit before reversing course and doing it all over again. It was driving Sara wild, but she valiantly kept up her work on his raging cock, determined to not get distracted.
Sara was a quick learner and even though Caleb had just had a massive orgasm, her mouth and tongue were bringing him close to cumming once again. Incredibly turned on, he knew he couldn't hold out much longer and wanted to save his next load of cum for her virgin pussy, so to distract her from her amazing blow job he pulled his finger back and instead of gliding it over her fuck hole like he had been doing he angled it up and let it slowly enter her hot, wet, tight eighteen-year-old pussy. As he suspected he felt no resistance as he had assumed Ashley's sex play had already broken through her hymen, and, also as he suspected, it had the desired result on her blow job as she gasped and shivered with joy, causing his nearly orgasmic dick to slip out of her mouth. But it was only a brief respite as she quickly latched back on to his cock and began sucking away in earnest. His dick ready to explode, he decided to pull out all the stops and twisting his finger inside her tight cunt so his palm was facing down, he curled his finger and quickly found her g-spot. Sara immediately lost her ability to continue blowing him as Caleb rubbed her pleasure spot with his expertly trained finger while at the same time massaged her tiny little clit with his thumb. In a matter of seconds she was cumming hard, her head now resting on the bed, her hands tightly grasping the blanket as waves of bliss cascaded out from her orgasmic pussy. Juices were pouring out of her sex, running down Caleb's arm and streaming down her skinny legs as she moaned loudly in the throes of the biggest orgasm of her young life. Eventually her knees slid back and she let her body collapse on the bed next to Caleb.
“Wow, what did you do? That was really great!” Sara panted after she had finally recovered.
“It's called a g-spot. It's a super sensitive bundle of nerves that many believe are an extension of the clitoris and if you know where to look you can send most girls into heaven.” Caleb responded slipping his finger out of her pussy and gently stroking her cute little ass, leaving trails of her pussy juices behind.
“I told you he was an excellent lover, didn't I?” Ashley said smiling over at Sara.
“Can we have sex now?” Sara said as she sat up and began running her fingers up and down Caleb's still rock hard dick.
“Sure, hop up here,” Caleb said happily, patting his lap.
Sara let out an excited little scream and quickly crawled on top of him, her thin legs straddling his waist, her still wet sex pressing against the middle of his penis.
“Now I want you to be in total control, okay?” Caleb said. “Put your hands on my chest and go at your own pace. If you feel any discomfort we can stop at any time, okay?”
“Okay,” Sara said breathlessly as she raised her pussy to the tip of his stiff member.
Ashley held the base of Caleb's penis and guided it towards Sara's waiting fuck hole. With just the very top resting against the entrance to her virgin pussy Caleb could already tell it was going to be a tight a fit, her weight alrea
dy partly being held up by his huge hard cock. But with her copious juices already in full flow the top of his dick was quickly well-lubricated as she rocked back and forth. She slowly let more and more of her weight down on top of Caleb's cock until the head suddenly popped inside her.
“Oh!” Sara said surprised.
“You okay?” Ashley asked putting her hand on Sara's shoulder to steady her.
“Yeah, yeah, feels freakin' awesome, just surprised me, that's all.”
After the head was inside her the rest was pretty easy as Sara just let her body slowly slide down on Caleb's big hard cock. Caleb and Sara and Ashley watched as his huge dick disappeared inside of the tight teen's pussy, stretching her pussy lips obscenely around the girth of his stiff penis. Inch after inch was engulfed by her fuck hole, and every time Caleb was positive she couldn't take anymore, she sunk down a little bit more until she was finally sitting all the way down at the base of his cock.
“How's it feel,” Ashley asked, her eyebrows raised expectantly.
“Pretty cool, I can feel it way up here!” Sara said pointing at a spot just below her bellybutton. “How’s it feel, Caleb?”
“I've fuckin' died and gone to heaven, Sara!” Caleb said almost out of his mind with pleasure. “Can you feel this?”
Caleb flexed his kegel muscles causing his cock to jump deep inside Sara's tight wet pussy.
“Oh! Yeah, wow, you can make it move!”
“Yep,” Caleb said and did it a few more times each time causing Sara to squeal with delight.
“Here let's try this.” Sara said as she carefully rose up, gently letting Caleb's cock slide a little ways out of her pussy before just as carefully lowering herself back down again.
“Oh, God, Sara, that feels so, so good!”
“Really, it feels super good for me too! You want me to do it some more?”
“God, yes!”
Sara rose up again this time letting a bit more of his hard thick cock slip out of her drenched pussy hole before again impaling herself on Caleb's stiff rod. And again, she pushed herself up a little faster this time, but back down just as slow as before. Sara kept doing it until she found a nice slow rhythm, always keeping her down stroke slow, but rising up faster and farther each time until she was coming up to the top of his cock each time and then slowly forcing Caleb's hard dick back up inside her snug pussy. Just before Caleb couldn't take much more Sara accidentally came up too far causing the head of his hyper sensitive dick to literally 'pop' out of her cunt. With Ashley's help she quickly popped it back in and as the bulbous head moved past her g-spot Sara went over the top in a mind-blowing orgasm. Caleb couldn’t take it anymore and grabbed her hips and sunk his raging hard cock deep inside her pussy and began to fuck her like she was some sort of delicate sex doll. It wasn't a hard or fast fuck by any stretch, but he was certainly fucking her at a quicker pace than before. Sara was cumming hard, her thin body convulsing every few seconds in yet another orgasm, her already tight cunt contracting wildly around Caleb's thrusting penis until he finally could not hold back any more and erupted deep inside her body. His cum poured out of the tip of his cock suddenly filling Sara's tight cunt so completely that with every stroke the white goo was forced out around the edges of where his cock and her pussy lips met. Cum sprayed and splattered as his hungry dick continued to refill Sara's fuck hole, his juices getting forced out as his big cock repeatedly slammed inside her. Again and again Caleb kept fucking her until she finally stopped cumming and collapsed on his chest, her pussy still firmly planted at the base of his now empty, semi-hard cock, trapping it inside her still occasionally spasmodic pussy.
It was almost five minutes later that Sara finally spoke.
“That was awesome!” She said breathlessly, “When can we do it again?”
“It was only a few weeks after that that Jacob and I had sex for the first time and our little group began.” Sara explained to Holly after telling her the story of her first time with Caleb. “I was also still having sex with Ashley and Caleb a few times a week until you came along.”
“I guess I can see how that would have made you pretty jealous of me.” Holly said sadly.
“Yeah, at first I was, but like I said I wasn't in love with Caleb like Ashley is, like we are. To me it was just amazing sex and I had my friends and Ashley, who was so sex starved without Caleb that she was practically wearing me out, so I wasn't deprived of sexual release ... but I have to admit, sex with Caleb was impossible to replace.”
“So you don't have sex with him now, even though he's back together with Ashley?”
“Nope, he didn't think it was right because you're my best friend. He told Ashley how much he misses me in their bed, but he just refuses to do anything that might hurt you. And to tell you the truth I didn't want to either cause I don't want to have to keep secrets from you.” Sara explained.
“But now I know and I don't want you to be deprived of his … good sex.”
“No. I would feel too weird, like I would be stealing something away from you.”
“No, really, I really want you to. I mean, I … I … wish that I could …” Holly said softly.
“Really, well, why don't you?”
“What? I can't just go up to him and ask for sex.” Holly said shaking her head. “He would never go for it.”
“Maybe your right,” Sara said and then smiled knowingly. “But I bet I know another way, if you don't mind sharing.”
Over the next few days they fine-tuned Sara's plan. The basic idea was to get Caleb to witness Holly and Sara having sex. If he reacted anything like he did when he walked in on Sara and Ashley, he would be powerless to refuse.
They set it up to happen over at Sara's house on a typical Ashley/Caleb date night, but for their plan to work they would need to get Ashley over on to their side. This was easily done as, much to Holly's surprise, Ashley already knew about Sara and Holly not to mention Jacob and Brian and Sasha and Katie. As Sara explained it, “Ashley and I have no secrets … well except for you know … the porn stuff.” Plus, Ashley was already a strong proponent of being open-minded sexually and since Holly wanted it so badly she certainly saw no harm in helping get Caleb over his possible hang ups, especially if it meant that Sara could join back in the fun and hopefully Holly too.
Caleb and Holly spent most of the day helping Ashley and Sara with their house projects as they had been doing two or three times a week since Caleb and Ashley had gotten back together. When they finished for the day Caleb and Ashley started making dinner and Sara and Holly ran up to Sara's room. After about 45 minutes, the cooking was nearly done, the table was set, and all that was missing were the girls.
“Could you go get the girls for dinner, Caleb?” Ashley asked doing her best to suppress her excitement at what awaited him.
“Yeah, sure,” Caleb said as he dried his hands on a dish towel and headed off to Sara's room.
As he disappeared down the hallway Ashley quietly followed, not wanting to miss any of the fun.
“Hey girls, time for dinner.” Caleb said as he opened Sara's bedroom door and suddenly stopped dead in his tracks.
The sight before his eyes nearly caused his penis to rip right through his shorts. The beautiful eighteen-year-old year old Holly and her equally gorgeous twenty-year-old best friend were sitting at the head of the bed completely naked, knees bent, legs spread wide, thrusting large dildos into each other’s pussies. They both looked up at him in mock shock, but quickly smiled and resumed fucking each other with their matching purple fake cocks.
“Caleb you're just in time. Holly was just telling me how much she wished this dildo was your hard cock.” Sara said with a breathless smile.
Caleb couldn't move ... the beauty and outright sexuality being displayed before him was almost too much to bear. He knew all about Sara's unforgettable body as it was one of the hardest thing he had ever done when had refused to sleep with her anymore, but sexy young Holly, the very reason he felt he had to shun Sara
from his bed, was a new revelation. It wasn't because he had never thought of her in that way, his head had filled with fantasies for the moment he met her, it was just that he never thought she was in tune with her sexuality in such a dramatic way.
He just stood and stared at the two naked young women pleasuring each other with such abandon. Sara, her slightly curly shoulder length blond hair framing her angelic face, her piercing blue-eyes filled with lust and mischief, her small perfectly round breasts, her toned lean body, her tight bare cunt being stretched wide by Holly's thrusting dildo, and her perfect ass half hidden by the bed, but still sharp in his mind. And of course the lovely, Holly, a few inches taller than Sara, her shiny light brown hair cut short just below her ears combined with her long legs and skinny body made her seem almost pixie-like. Her breasts were perfect handfuls of heaving hard youthful sexuality, her two little pink nipples sticking straight out, the journey down her flat belly and waist was almost uninterrupted by her skinny hips leading down to her small tight ass and gorgeous cunt that was currently being filled by the latex dildo being pumped into her lean frame by her best friend. Her brown eyes were sharp and locked on to Caleb's with pure lustful intentions.
Holly’s Island: The Complete Collection Page 9