John was obsessed with anal sex… unfortunately his girlfriend of the past year refused to have anything to do with anal sex. She wouldn’t let him anywhere near her beautiful ass, not with his hands, tongue and definitely not his dick. Insisting that it would be far too painful to even try – not that she ever had he thought grudgingly – she would only be involved in the most straight-laced sex. Lauren wouldn’t even allow the doggy-style position, insisting that it was obscene and degrading.
There were times when he despaired of it… she was just so incredibly prudish about some things. She’d suck his dick but she wouldn’t swallow… she’d have sex before marriage but wouldn’t experiment with positions… and even though she was constantly wearing clothes that showed off her beautiful ass she wouldn’t let him anywhere near it. It was enough to give a guy permanent blue balls really…
He yearned for some excitement and deviation in their sexual life… and he probably wouldn’t even have minded her strictures on anal sex if she’d at least been willing to try! But no… she heard from someone who knew someone who knew someone that anal sex was extremely painful. It bothered him because he’d been willing to try a lot of things that she’d wanted to do, although none of them were sexual. And while pottery classes weren’t his favorite thing in the world, he continued to go to them because it made her happy.
It seemed patently unfair that she would be so unwilling to do the same for him.
Then, one night he was at a friend’s house and for some reason unable to sleep. Doug offered him some sleeping pills that he used when he was having trouble. Within minutes, John was completely knocked out.
When he awoke the next morning, feeling totally refreshed he had the inklings of an idea. Asking Doug for some more of the pills, his friend willingly gave them over, having no idea what John had in mind… although he probably wouldn’t have cared too much if he had. He thought that Lauren was an incredibly selfish girlfriend, he knew he’d never put up with all the crap that John had to.
That night, John set about to making a spectacular dinner for him and Lauren, all her favorite foods. She squealed with delight when she came home to such a thoughtful surprise.
‘Something for her… and then something for me…’ John thought excitedly.
As soon as dinner was over, he had her pop in a movie while he prepared some sweet dessert wine… crumbling three of the sleeping pills into it. Since he’d had such an uninterrupted blissful sleep after taking one and a half, he figured nothing short of the end of the world would wake her up at three.
Indeed, about five minutes into the movie, she’d completely finished off her wine and was falling asleep in his arms. He waited fifteen minutes, just to be sure that she was totally asleep, and then turned off the movie and carried her up to the bed. It was a little strange, having her unconcious as he undressed her… for a few moments he had second thoughts… but when he turned her over and saw her delicious ass his doubts flew away in the few seconds it took for his dick to come to full mast.
Carefully he arranged her, face down with her ass high in the air – propped up by pillows underneath her hips. Gently he turned her face to the side so that she wouldn’t suffocate. Staring hungrily at her virgin asshole, he lathered lubricant on his dick. Standing there, staring at the small hole that was going to accommodate his very hard dick, he wondered whether or not he should loosen her up first.
Then, thinking about all the trials she’d put him through, he decided that no, he shouldn’t. Besides, it wasn’t as if she was REALLY going to be feeling it.
Arranging himself behind her upturned ass, John pulled Lauren’s fleshy ass-cheeks apart to totally reveal her tiny asshole to him. It looked awfully small next to his engorged dick… ah well.
Positioning himself, he stabbed forward, moaning as the mushroom head of his dick sank into her asshole. It was the tightest thing he’d ever felt, a hot ring squeezing his dick pleasurably. Moving his hips he thrust more of his dick into her ass… a small whimper stopped him… but when she didn’t make any more noise he let more and more of his dick sink into her ass.
Fully inside of her, her deflowered ass rippled around his dick, and he could see her pained expression, small whimpers emitting from her as she slept. Apparently it hurt. Something vindictive broke inside John and he started fucking her ass hard, loving the fact that she was finally forced – FORCED – to accept her ass-fucking. The whimpers got louder as he thrust in and out of her tight ass, his fingers digging into her hips as he pillaged her formerly virgin territory.
It was hot, tight, the best ass-fuck he’d ever had… and Lauren had no idea it was even going on. Reaching around her body, he grabbed hold of her swaying tits, using them to lever himself even deeper into her ass, forcibly sodomizing her.
The entire situation turned him on so much that he exploded in her ass, gasping and thrusting as spurts of cum gushed into her hole, it felt like he was dumping gallons of cum into her ass. Holding himself tight against her body, he could feel her hole convulsing around him as he came, pleasuring him even more throughout his orgasm.
With a contented sigh, he collapsed on top of his sleeping girlfriend, his dick slowly shrinking in her deflowered hole.
Happily, he looked over at the drawer where he’d hid the sleeping pills. Enough for three more nights if he wanted… and he’d have to talk to Doug about getting more.

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