An Anal Awakening Ch. 3

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Jack gets the jitters about what Jo expects of him.
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Part 3 of the 3 part series

Updated 09/22/2022
Created 02/01/2001
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C_Duke
C_Duke
55 Followers

They'd arranged to meet up again the following weekend. Although Jack and Jo had seen Cliff at college all week they'd only really exchanged sly glances as to what had gone before. The sex Jo and Jack had been enjoying since the threesome had been wonderful, and intense, but somehow different with the new dimensions they'd explored. Even though no third party had been there before, they both noticed a sense of quiet without the man who had taken Jo's anal virginity and introduced Jack to the enjoyment that lay beyond the female partner. Jack had fucked Jo in the ass a couple of times during the week and they had both enjoyed it, her screams were so intense, and the power of the orgasms she found she could have when her pussy was stimulated at the same time were truly amazing.

The night before, Jack had removed his softening tool from her ass, which was freshly filled with his wave of spunk. He had the taste of his own cum in his mouth too, from a deep wet and very messy kiss they had shared right after his previous orgasm about twenty minutes earlier when he had offloaded his churning white wonder into her eager mouth, which was as amazing at its oral trade as ever.

"God Jack, baby you're SO good... I love it when you do it to me so well... and I really like it when you fuck my ass after you've made me cum so many times." She said, laying back and closing her eyes.

"It doesn't hurt any more, baby?" he asked, with genuine concern, looking down into her beautiful tanned face, so peaceful and serene with the waves of pleasure slowly receding from her. "I know you didn't really like it at first... I know its pretty big..." he looked down at the obvious.

"No its okay... really... and its SO nice." She giggled and nudged him. "Just always got to use the lube and go gentle at first. Damn, it feels good, I really love it when you cum in me... God your cum feels so good deep inside me."

"Mmmmmm... I like that too..." he smiled stupidly to himself. "Is it better getting fucked in the ass than doing it normally?"

"I want to try it double again, Jacky. I really want to get fucked like an animal this weekend. Its fucking great in the ass... but I come harder in my pussy." She was surprised herself at the admission "It was so good... I need to get fucked REALLY hard again, both in my pussy and in my ass. So, BOTH, at once, is the best!" She could hardly believe the words were coming out. "You like to do that with me again Jacky?"

"It was great last time, baby. I think it'll be even better this time." he said, twisting a curl of her brown hair in a wandering finger. "I kind of like seeing you get fucked... feeling you enjoy yourself so much."

"What did you think of sucking cock, Jacky?" she asked... knowing the answer that he wouldn't admit out loud (she KNEW how good it was, but guys who tried it rarely told others they liked it).

"I love you, Jo." he leaned forward and kissed her full on the mouth even as she sat up suddenly to look into his eyes. He hadn't actually ever said it before like that. Neither had she. But they both knew it.

"Jacky?"

"Hm?"

"Really. What did you think of giving Cliff a blow job?"

"I... err... it was..." Jack only stammered when he was really uncomfortable. He was very sexually confident.

"You liked it didn't you?" she bluntly asked him. "You enjoyed that hard prick in your mouth!" her smile was almost evil in its sweet-naughtiness. "Didn't you!"

"Jo, baby... I, errrr... what are you getting at?"

"Didn't you?!?"

"Yes." He replied meekly, looking at the floor. "It was strange at first, but I found myself really getting off on it, baby. I think I'd do it again... but I just freaked totally when he came in my mouth." Jack admitted "Yuk!" and grimaced.

"I want the next threesome to be even better. I hope you and Cliff will entertain me!" She had been so turned on when she'd seen the 2 guys in the shower together.

"Oh, don't worry, you'll get a workout. You won't know what hit you when I get so hard playing with Cliff and stick it hard in your unsuspecting ASS!" Jack whispered.

"I think EVERYONE should try it in the ass." Jo said back into his ear, even more quietly, and kissed him.

The both felt a faraway electricity building up somewhere deep inside their bodies as they kissed and bit and sucked each others' tongues and mouths and faces, groping each others' bodies like pythons trying to bearhug each other. No more words were needed and they lay with each other kissing for a long time. It was a beautiful feeling which didn't end but became more erotic when they made love for the rest of the morning before rolling shabbily into college smelling of sex and feeling twice as horny.

That Friday at college was a difficult day to keep the mind off sex for Jo Jack, and Cliff. They'd upgraded the motel room from the weekend before to the motel's best effort at a presidential suite, as in it had a water bed and a jacuzzi. But they had to wait for Saturday night.

Jo spent the entire day somewhere between damp and wet (biology was difficult to concentrate on seriously) and Jack and Cliff were both at least half-hard all day long. Jo grabbed both guys during the lunch hour and dragged them both unresisting into an empty classroom and locked the door. Her smile told them what she didn't have to say. She just couldn't wait a second longer! She pushed them into sitting positions on the desk and squatted down, her legs wide open to the floor and hard-ons clearly visible in the jeans at her eye-height.

"Shouldn't we try and save it for tomorrow..." Cliff started but soon trailed off as he felt a warm hand where it mattered most "...OooOOoOOOOOOooohhhh..."

She released both cocks from there denim prisons simultaneously with a little help from their owners and the 2 hard-mushroom-headed pokers burst to attention even as she greedily devoured one after the other. Jack and Cliff tensed then relaxed their bodies and sighed in extreme pleasure at the release from the day-long buildup... it was such a relief to be experiencing what they had thought about all day. Jo was without a doubt as busy as she could be... the one hand beating off the cock she wasn't sucking, the other fiddling with her clitty with a little difficulty up her skirt and past her panties. She wasn't using her tongue and mouth as expertly as she might have done if she wasn't in such a frenzy... she wanted an orgasm as quickly as she could bring it on and have the guys' big cocks squirting in her mouth!

So she sucked HARD and nibbled excitedly and quickly on Jacks engorged head, tonguing and sucking and nibbling all over, sucking until her lips whitened with the pressure... beating off hard Cliff's 7" cock even as she plumbed herself with two fingers so hard that her fingernails made her wince. Beating off and sucking and fingering... Jack's cock... Cliff's cock... Jack's cock... Cliff's cock... oh she was happy, she was cumming, she had two lovely big cocks bouncing in front of her face as she pleasured herself. She squealed as her temperature flew a few degrees and she wettened her fingers suddenly with her hot and sticky climax.

Cliff totally surprised Jack when at the height of their mutual pleasure he leaned over and kissed him, full on the lips and inserted a hungry tongue into his unsuspecting mouth. In shock and confusion, Jack just reciprocated and enjoyed the oddity. (Neither of them mentioned it later that day). They changed positions after a few minutes, and Jo pulled Jack down to his knees. Before he could hesitate, Jo kissed him and pushed his face over to Cliff's throbbing cock-head, taking his balls in her mouth. Jack for the second time in his life had a mouthful of cock, and found himself quite hard with the sensation of that thing past his lips... and the fact it was so sudden, unplanned, and thrust upon him by none other than his own girl!

"MMMMmmmMmmmmppppphhhhhhmmmmMMMMm..."

"Oh, Jacky baby, you look SO sexy." Jo whispered in shivering excitement as she continued playing her clitty and suckling Cliff's nuts.

"FUCK, MAN! YEAH!" Cliff barely suppressed his volume.

Jack dropped one hand to beat himself off... wanting to climax soon, wanting to cum. Cliff really had to concentrate to not cum with the fantastic attention the 2 mouths gave his most erogenous area and moaned and sighed and grit his teeth and ran fingers through their hair. Jo released Cliff's balls after a while and kissed Jack again, and their tongues shared that big cock head for a minute or so, and the pre-cum was more than seeping, a feeling enjoyed by both the lovers.

Cliff felt himself cumming, but didn't want to totally freak Jack out by shooting off hot into his mouth. It didn't seem so inappropriate last time, at the end of their marathon orgy session so he grit his teeth and tortured himself with the enticing pleasure.

Jo dropped down and took Jack's head in her mouth, sucking his cock while he sucked Cliff. She knew he was enjoying this whether he would admit it or not because he was as hard as he ever got, which was a very hard, hot, pulsing, almost frighteningly thick 8" of hard. She beat his length and snaked her tongue like a tentacle all over it. Jack always enjoyed Jo's oral abilities, and turned on as he was by the strange but nice feeling of dick in his mouth, which he was exploring with interest with his tongue, taking it past his lips and into the back of his throat, nibbling all around the head gently with his front teeth, and licking the seeping hole and all around the sweaty pink rim. With that great feeling of dick in his mouth, so new to him and still so weird, and Jo's amazing mouth doing its thing to him, he didn't feel the need to hold back. He came, and it felt GREAT.

He bit down on the shaft in his mouth involuntarily as a shudderingly good orgasm coursed through him, and he fed Jo the massive bolt of white hot cum she'd been aching for... he shuddered 3 or 4 times as each new jet of cream blasted into the back of her throat and filled her mouth... all 3 of them had their eyes screwed up with different sensations... Jack with overpowering ecstasy, Jo with the sudden, familiar and wonderful sharp flavour filling her tastebuds, and Cliff with the teeth on his shaft with a wince of pain and still trying not to cum. Jo's busy fingers brought another orgasm on with the feeling that the wonderful taste of cum always gave her.

"Man... you must really like sucking my cock, dude." he joked as Jack released it from his mouth. "You want it baby?" he asked Jo as he pointed himself at her face, beating himself off, so close to cumming now, the point of no return. His whole body jerked with an almost electrical blast of pleasure from deep within, and a mere instant later he started to ejaculate hard, literally firing his stream through the air.

She moved up off the floor onto her knees, released Jack's cock and smiled up at him, then opened her mouth revealing the coating of smooth thick white still all over her tongue. She was a second too late and caught his it right in her eyes and hair before she opened her mouth to him.

Cliff placed his helmet just inside her open mouth as the first shot escaped... and his whole body arched and stiffened as 2 or 3 more blasts of pleasure landed as perfectly aimed right at the back of her throat. Jack surprised them both (and himself) when he fondled Cliff's sac with his fingers, to coax the good stuff out, and then by taking the cock in his hand when Cliff had apparently finished cumming, liberating it, hot, sticky, sweaty and slimy from Jo's cream-filled and overflowing mouth and licked the end as a last couple of drops appeared, then sucked on the spunky head briefly, cleaning it up.

"Jacky BABY!" Jo squealed in pleasure after she had swallowed as much as she could, hiccupped and then licked her white lips. "I KNEW you liked it! Oh, Jacky!!!"

He smiled sheepishly and was given a big open mouth kiss for his new trick, and the taste of the mix of semen was was still very fresh. Jack wondered if it should disgust him or not. It didn't feel wrong. Weird, and yukky in retrospect, but he enjoyed it.

They all felt a sudden feeling of guilt and pulled their discarded clothes back on and after quickly checking the corridor wandered back out of the classroom and toward the cafeteria. This lunch had been very well earned! They didn't need to but they confirmed time and place for the following night.

Jo gave both Jack and Cliff strict instructions not to play with themselves until they all met up... she wanted everyone fresh and on top form for the group fuck.

The rest of the day at college went as uneventfully as it might, Jo got the usual offers a girl of her talents got when such a girl wore a skirt as short as she did now, and from the usual sources - big butch guys, white and black. She wondered guiltily and squeezed Jack's hand during one recess what a big black cock would be like. She dampened considerably, but didn't share the thought.

Jo went on to Cheerleader dance / sync practise and Jack asked her to wear the outfit the following night.

"I can't wait baby... it'll be SO good again. Watch you suck cock while I squeeze into your little ass, or have you get both at one time again..." Jack mumbled into her ear while they were un-self-consciously necking outside the girls' locker room. It was unusual for him to talk dirty, it was normally her forte.

"You just want to suck Cliff's cock you dirty bastard!" she teased him.

Jack didn't know how to answer so he grabbed her ass and kissed her hard.

"I'll go and catch Cliff when he gets out of tennis and we'll grab a beer" he tried to change the subject unsuccessfully.

"Maybe you just want to blow each other in the John."

"Maybe we will! Maybe we don't even need you tomorrow."

"Maybe you'll drop your pants and he'll fuck YOU in the ass then!" Game, set and match. Jo knew she'd won the playful argument.

Jack looked back at her suitably shell-shocked.

"See you tomorrow, baby. I love you." and he gave her a soulless peck on the cheek and squeeze of her ass.

"Off to check out your boy in the shower again?" she smiled wickedly before he could turn around and head off.

"JO." Jack gave her his enough-is-enough look, and tried not to think about it. He'd been hard most of the afternoon anyway without her mocking him about THAT.

"I love you too, baby." And she jumped forward and planted one of her big lips-just-apart-full-on-the-mouth kisses on Jack's annoyed face, pacifying him instantly.

He sent on her way with a slap on the ass and made his way over to the gym to catch up with Cliff. He'd be finished his tennis game with Rad by now. Jack wasn't so good at Tennis, football was his thing, but he'd played Rad a couple of times. The Chinese guy was good, real fast, running circles around Jack the all-star quarter back. He tried really hard to get Jo's teasing out of his head, but failed to get any other thoughts in there.

Besides making it with a guy, even Cliff would be weird without Jo. What was he even thinking?!? ("STOP IT") he told himself. Besides it would be in public. Again he shook his head ("STOP IT") but he was hard as ever he was with Jo and limped with it.

His confusion was just beginning to abate when he made it to the gym. The locker room was pretty empty and he had to call out Cliff's name. He heard no reply but there was someone in the shower, so he decided to stick his head in and shout to his buddy that the evening's entertainment would be a lot sooner than planned. His brain went into overdrive again an instant later. When he SAW.

The only guys in the shower, in fact in the whole locker room, were Cliff and his sporting opponent. What Jack didn't expect was to find Cliff on his knees, shower beating down on him with a mouthful of the Chinese boy's prick, beating it off with a very quick wrist. Jack stifled a gasp and remained quiet, watching in awe.

Cliff had always quite liked Rad but had only discovered he was bi a couple of weeks ago when he "accidentally" brushed his cock in the shower. He tried it with a lot of guys' cocks or asses that he liked. Usually the jocular response was a punch on the arm and get called a fag. But Rad had smiled, and "accidentally" smacked Cliff's ass a minute later. This was the 3rd time they'd had sex on campus. Cliff was also getting a little better at Tennis.

And like those times before Cliff was always the first to grab Rad's cock and have it start to stiffen up moments before he tried to swallow it. Rad always returned the favour but wasn't confident enough to start anything. Jack watched in fascination as the Chinese boy stretched his whole body back and sighed, his muscles taut. He looked almost godly with the warm water careering over his body, like some Sexual Historical Statue, with his big cock being serviced by a warrior's houseboy out of some myth or legend. Cliff was no stranger to pleasuring a male body and Jack watched him use his mouth and hands expertly, only occasionally reaching down to his own cock which was sticking right out 90o from his glistening body. Jack was unprepared for what happened next. Rad first began to softly finger Cliff's head and ears and then coaxed him to his feet and planted a deep wet kiss hard on his lips. The way their arms moved around each others' bodies was a beautiful sight, albeit an unnatural one to Jack.

He was half in fear ("PLEASE NO" he thought), half in perverted fascination ("PLEASE YES") as Rad reached a hand around and pushed first one then two fingers between Cliff's buttocks which parted at the request, and found he couldn't take his eyes off the frenzied kissing or the two hard cocks, both about 7 inches long bouncing against navels and each other. Jack had to bite his fist when Rad coaxed Cliff around to face away from him and bend over.

("OH NO OH MY GOD HE'S GOING TO FUCK HIM CLIFF'S GOING TO GET FUCKED OH WOW CLIFF'S GOING TO GET FUCKED RIGHT UP THE ASS")

Cliff's face screwed up and then smiled and then opened up in joy and awe as he felt himself being penetrated, that big wet prick, a little bigger than his own forced first into his hole and then up, deeper inside him, and he started to pant and grunt and "oh yea" as Rad's strong chestnut coloured hands gripped his hips, and seconds later, as both guys adjusted their feet and hips he was getting fucked. Oh, that wonderful feeling, being humped by a nice hard prick, real hard but not too big.

Both tennis partners began to pant and sigh and make all manner of noises as they got into a rhythm, saying meaningless things like "Fuck me... oh yea.. harder... you like that... fuck me... oh yea... you like that cock... damn its so good... love your ass... fuck I love that... you like this big cock... etc" Jack couldn't believe what he was seeing or hearing. Rad was pumping in deep, hard and up, slamming all 7 inches in Cliff's ass, making him squeal slightly when Rad's body slapped up against his. He was beating his own prick off pretty feverishly, hadn't softened a bit. Jack knew the look on Rad's face, he was going to cum, and Cliff wouldn't be far behind him.

Jack stared in disbelief as Cliff, his buddy Cliff, got his butt pumped and loved it. Watched his buddy getting it good and hard up the ass and about to be filled with cum. He hated himself for his own hard dick and wanted to go and watch Jo in her Cheerleader dance/sync but he couldn't tear himself away.

Cliff came in a torrent. With Rad fucking him harder and harder as he himself came closer to climax, Cliff's cock spat boiling white lust all over the shower floor and his regular happy/hurts grunts from Rad's bodily penetrations were overtook by a single, great roar of satisfaction as he achieved simultaneous regular and anal orgasm, firing off a superb quantity of thick, hard-earned cum into the beating warm water splashing on the tyles. Jack watched in quiet disbelief the pure intensity of the orgasm he saw Cliff have, the sheer amount of cum and the distance the stuff flew, fired by some incredible force from his exploding prick, again and again, until at last his body started to sag from the effort.

C_Duke
C_Duke
55 Followers
12