The Loophole

Andy knew he wasn't strong enough to resist what was being offered to him on a plate here. How could he be? Before arriving at university for the first time he had never so much as kissed a girl, and was too shy to even talk to the pretty ones. Now one of the hottest women he had ever met was lying naked on his bed practically demanding he fuck her. What's more, she had a look of unbridled desire in her eyes he had never believed he would be able to inspire in any female. How was he supposed to turn her down?

Even when he made an attempt to think about this practically, it clearly wasn't a situation where he could placate Elaine by graciously allowing her to jerk him off or suck his dick. He had, albeit improbably and almost accidentally, made her hot for him tonight and she wanted to be satisfied too. On top of that, it would look pretty fucking incongruous if he attempted to play the chaste gentleman tonight then lure her into a threesome with her sexy best friend within the next forty eight hours.

There was only one course of action Andy could reasonably take here and, thankfully, it was an extremely pleasurable one. He knew how to get to the verge of a threesome by now. He would just have to retrace his steps on the next run, but in a way that made Elaine not quite so lustful for him so early on, as absurd as that notion sounded even in his own head.

Andy began undressing as Elaine beckoned him towards her with a 'come to bed' smile that was almost too much for him to handle.

A part of Andy feared he was going to cum before he even got as far as touching her. How long had he lasted inside Leah, the one time he'd had full sexual intercourse up until now? If he was honest with himself, probably not even a full minute. But he'd had a lot more experience by now. Sure, he hadn't gone quite that far with anyone else yet, but he'd spent a pleasantly surprising amount of time around gorgeous, naked women, often in close bodily contact with them. He'd had his dick sucked on a few occasions. He'd tasted Tina's pussy. Sure, nobody was going to mistake him for James Bond any time soon, but he was no longer a clueless virgin either. And he needed to keep in mind that Elaine was just a person. A beautiful, sexy, perfectly formed and deliciously fuckable person. But a person nonetheless, and not some insatiable goddess. He could do this!

Andy climbed onto his bed and embraced Elaine, his naked body soon becoming tangled up with hers. As they made out, he began to explore her with his hands, hungrily running them over every curve and crevice of Elaine's flawless form that he could reach. He knew he couldn't indulge in anything resembling foreplay for too long though - especially now he felt Elaine taking hold of his dick and starting to gently massage it between her fingers. Going off in her hand would keep the week going, but in a most embarrassing way that could hardly be expected to warm his date up for a threesome.

Andy therefore decided it was time. He placed his palms on Elaine's thighs and she gave no resistance as he spread her legs apart. He then plunged his dick right into her now moistened slit.

This was it. The second time he had got to the fucking stage with a woman, and it was Elaine of all people! Someone who had initially seemed almost completely unattainable. But this felt surprisingly natural as she wrapped her arms and legs around Andy and made encouraging noises that indicated she was at the very least satisfied with his performance.

"Mmm, keep it going baby!"

He easily passed the minute mark this time and felt like he could last much longer still. This was a world apart from his fumbled attempt to sexually satisfy Leah before. But, in the midst of would should have been one of the happiest and most pleasurable experiences of Andy's life, a nagging feeling began to gnaw away at him from the back of his mind. What if this was too perfect? What if the moment he ejaculated into Elaine, which he couldn't reasonably or biologically be expected to hold off for much longer, he didn't go back to the start of the week. What if his entire experience ended - here and Leah, Gemma, Sara, Tamara, Tina, Aurora and Kara lost all romantic interest in him immediately and forever, with all but Leah becoming virtual strangers again. He just wasn't ready for that.

Andy could feel that he was now passing the point of no return so, in a moment of blind panic, he whipped his dick out of Elaine's pussy as if he were pulling the plug from a hazardous appliance.

"Andy, what are you..."

A look of sudden panic spread across both of their faces. But it was too late. Before either of them could do anything to stop it, Andy was spraying his spunk all over Elaine's tummy and tits. Much to his horror, he could see that some of it had even gotten into her hair.

"Andy, what the actual fuck?!"

"I'm sorry, I.."

"You said your thing was threesomes, not jizzing onto my boobs! You should have at least discussed this with me first!"

"No, it wasn't that" Andy attempted to protest his relative innocence in a manner that seemed even vaguely plausible "I didn't want you to get pregnant!"

Elaine's eyes and mouth widened in unison in disbelief at that statement.

"I'm on the fucking pill!"

She looked mad for a few more seconds and then, mercifully, burst out laughing.

"Fucking hell Andy, I was enjoying that as well! Can you fetch me some tissues or toilet roll or something to clean your mess up. I guess I'll have to finish myself off!"

Andy pulled his boxer shorts back on and dutifully sprinted a few yours down the corridor to the communal washroom, where he grabbed a whole roll of toilet paper. It actually looked like she might need most of it. He returned to find Elaine lying on his bed, partially spattered with his goo, with her eyes shut and masturbating. At this rate, he would be ready to go again much quicker than expected - but he knew he needed to call it a night.

Once she had achieved her own orgasm and cleaned herself up as best she could with the toilet paper provided, Elaine stood up and gave Andy an affectionate peck on the lips.

"I was planning on sleeping over, but I feel like I need to go back to my own floor and take a shower instead" she gestured at her still mildly cum soaked hair "I think next time we'll take a less dramatic approach to birth control, yeah?"

Once Elaine had dressed and left, Andy lay on his bed and tried to evaluate what had just happened. Had that all played out in a way that was more than a little humiliating for him? Undeniably, yes. But he had fucked Elaine - that in itself was a monumental achievement. Not only that, he had performed competently between the sheets and she was already talking about them doing it again. She even said she had been enjoying the experience.

Guiltily, he had to admit to himself that, at least in hindsight, cumming over Elaine's tits had been pretty hot. And how cool had she been about it all? Maybe she really would be open for a threesome.

And that was perhaps the best part of all of this. He was still here, the week would continue. Andy had managed to find a loophole - not one he would be keen on using too often, but it had done its job for this run. Leah would have her lottery win tomorrow. Elaine was already sexually active with him. If Andy was ever going to get to experience his dream threesome with these two, it would be in the next few days.