Which was something he could never, ever tell his wife, or Izzy for that matter, but feeling that incredible tightness around him, and knowing why, knowing that this was a dream come true, his most forbidden fantasy made a reality, and fuck, how could it be anything but the greatest moment of his life?
Luckily the two women didn't seem to notice just how much he was enjoying this. Which wasn't surprising as far as Izzy was concerned, as he could only imagine how distracting a cock up the ass could be. Not that he wanted to find out. But maybe his wife now did. She had always been very against anal, but she agreed to this, and now they were doing it she seemed fascinated by it.
And maybe even Izzy could talk her into it, which was the only way this could get better. If Emma bent over beside Izzy and begged him to take her anal virginity next, just the idea of it very nearly making Jack go over the edge it felt like he'd been on since officially popping Izzy's anal cherry.
That he had resisted for this long had to be some kind of miracle, and he really felt he deserved some credit, at least afterwards, for his fine performance. However even though the past couple of weeks with Izzy had drastically increased his stamina he was only a mortal man, and he knew he couldn't last much longer.
All he could really do was hope to make Izzy cum too, and given that he had been gently thrusting in and out of her butt for several long minutes he felt that she'd be ready for a harder ass fucking. Or at least Jack hoped she would, because that was the only way he could imagine making her cum at this point.
So he began gently increasing his pace, eventually beginning to butt fuck Izzy as hard as he'd ever fucked a woman's pussy before, hoping and praying this last assault would make his girlfriend cum, and in doing so ensuring this hopefully wouldn't be a one time thing.
Then he lost the ability to care about anything as he suddenly received the hardest climax of his life, his cock suddenly erupting like a volcano, shooting spurt after spurt of cum deep into Izzy's bowels. Oh God, he was cumming in a woman's ass. He was cumming in Izzy's ass. The woman who he shared with his wife. Wonderful Izzy who was taking every drop of his sperm up her butt.
Izzy had been close. So close to cumming herself. Then Jack came, and Izzy thought she was going to go over the edge just from feeling him unleash inside her. Unfortunately while it felt so wonderfully dirty, naughty and forbidden, just like the anal sex itself, it didn't quite get the job done, and all too soon Jack softened and slipped out of her, the man in question collapsing down beside her, leaving her with only a few options.
The easiest one was to reach down and finish the job herself, but she was on such an anal high that Izzy didn't want to switch to pussy stimulation, not when there could be a chance of her still cumming from getting fucked in the ass like she wanted.
"More." Izzy whimpered, "Need more."
"I'd love too, but you don't have to give me a minute." Jack quipped.
"I wasn't talking to you." Izzy said, turning to Emma, who was clearly surprised by this revelation, "Please Ems? Please do this for me? Please? Please get a toy, mmmmm, or a finger, whatever and shove it up my ass! I wanna cum that way. Please? Please do this for me!"
There was a long pause and then Emma asked softly, "What do you want?"
"The strap-on!" Izzy said eagerly, "I want you to strap on a nice big cock and fuck my ass with it."
There was another pause and then Emma slowly did as she was told. Which was great, because Izzy thought she was going to have to really talk Emma into this, totally coming down from her high in the process. Or maybe that would mean better, because it would have meant more butt fucking.
No, Izzy wanted to cum now, and the sight of Emma slowly retrieving her harness and attaching it while Jack watched in amazement was definitely doing a good job of keeping her excited. To make matters even better Emma got out the lube and coated the dildo with it, which was exactly what Izzy was about to ask her to do so they could get the show back on the road.
Nervously approaching Emma asked, "Are you sure about this?"
"Oh fuck yeah." Izzy said eagerly, turning her ass to Emma and eagerly spreading her own cheeks, "Fuck my ass! Mmmmmm, fuck me in the ass and make me cum. Please Ems? I need it."
Even though the next pause was mercifully brief Izzy still opened her mouth to start begging again, only for Emma to kneel down behind her and press the tip of her strap-on to her cum leaking butt hole. This process repeating itself as there was another infuriating pause, but then finally Izzy cried out in mostly pleasure pretty much the second that she'd opened her mouth as her girlfriend pushed her cock into her ass.
The ass that was full of her boyfriend's cum. Her girlfriend's husband's cum! God, this was so hot, Izzy so overwhelmed by those thoughts that she didn't even care that Emma insisted on anally penetrating her ridiculously slowly. In fact she kind of liked it, because it gave her the chance to savour the feeling, and the thoughts echoing through her head.
It was pretty much the same story for the rest of the anal penetration and the initial butt fucking, because sure, it wasn't the orgasm Izzy had been craving, but it meant more pleasure coming from her apparently incredibly slutty ass, and that was good enough for now. Especially as Emma seemed to really get into it, surprisingly so.
Or maybe it shouldn't be that surprising given the suburban wife was much more kinky than most would think when first meeting her. And of course Jack was enjoying the show, his dick returning to full hardness in what had to be record time, giving Izzy a wonderfully wicked idea which she just couldn't get out of her head until she finally made it happen.
Jack had always loved watching Emma fucking Izzy with a strap-on, and vice versa. He loved watching them fuck in any way, but this? This was truly mind blowing. Especially because after he had fucked it Izzy's butt seemed to easily welcome Emma's cock, swallowing every last inch of it without a hint of pain or discomfort from the younger girl.
Hell, it felt like there was barely any time at all between when Emma initially pushed her dildo through Izzy's ass hole and the moment his wife's thighs came to rest against his girlfriend's butt cheeks, announcing every inch of that strap-on was deeply embedded within her rectum. Then after only a few minutes of Emma savouring that fact Izzy begged for more.
"Mmmmm, fuck me!" Izzy moaned, "Fuck my little ass! Please Em, ass fuck me! Fuck me in the ass, ooooooh, fuck my ass while it's full of your husband's cum. Oh God yes, I want both the Trakarskys to fuck my slutty little ass hole in the same night! Please, oh please, Emma, baby, ohhhhhhh Goooooooooddddddddd yeeeeeeeessssssss, fuck me!"
At first Emma seemed taken aback by just how quickly Izzy begged for this, and perhaps just how eagerly she asked for it, but then she grabbed a firm hold of her hips and began pumping back and forth, Jack's wife officially starting to ass fuck their girlfriend.
Unable, and unwilling, to help himself Jack move closer so he could see the same thing his wife was staring at, namely their girlfriend's ass hole stretching for the dildo pumping in and out of it, Izzy giving them both the perfect view of it as she continued spreading her cheeks.
He couldn't accurately describe how hot that was, he and Emma becoming completely lost in that perverted view for a few minutes. They were then very disappointed when Izzy took her hands off her cheeks and lifted herself up onto all fours, although at least he wasn't disappointed for long.
"Jack, mmmmm, let me suck your cock! I wanna suck your cock!" Izzy pleaded with a loud moan, "Ohhhhhhh yesssss, I want to take it in both ends. Ooooooh, I love taking it in both ends for you two, and I want to do it in a way we've never done it before. So please, oh yes, give it to me, oh Jack."
Practically tripping over himself to get in position in front of his girlfriend Jack then let out a loud cry as Izzy immediately wrapped her lips around his dick at the first opportunity. The dick which had just been inside her own ass, and she moaned. Moaned in pleasure from tasting her own ass. Or maybe that was just from Emma fucking her in the ass.