Late Night Fun

It was getting late. Jonathan stretched in his desk chair and sighed. He had work tomorrow and staying up this late to finish a personal project hadn’t been a great idea. He put his computer into sleep mode, turned his fan to face the bed, and walked the few steps across the room to get into bed. The night was unbearably hot but no amount of heat would stop him from pulling the covers up to his neck. Jonathan grabbed the big, squishy pillow that lay at the end of his bed, and put it between his legs. The fabric was cold and it helped on nights like tonight when he needed to stay cool. Just as he was about to turn onto his side to fall asleep, something pressed against his dick and sent a surge of pleasure through him. He shifted his hips, finding the hard seam of the pillow pressed right against his freshly-trimmed pussy. He squeezed his thighs a little tighter around it and gave a tentative thrust. The feeling of the seam rubbing against his dick was enough to shock the exhaustion out of him and replace it with arousal. It was only 11:40. He could take a few minutes to get off, couldn’t he? Jonathan rolled over onto his belly, pulling the pillow up further so the seam dragged deliciously against his lips. He started to rut against it, no longer tired. It was heaven on his little cock. He spread his legs to get a better angle and soon the seam was sliding between his folds. He shuddered, thrusting eagerly against the pillow. He was already wet, slick soaking into the fabric and making the ride smoother. Despite how terrible of an idea it was, he thought of his ex. Just the memory of her tits made him double down on his efforts. He let out a whine as the pillow dragged between the soft folds of his cunt. Holding the pillow, he could almost imagine he was holding her boobs, though they were considerably less malleable. If he’d been on T at the time, maybe he could’ve fucked them, squeezed them tight around his dick and gotten himself off. His dick caught on the seam and he keened. He tried to do it again but couldn’t manage. Jonathan was flushed and starting to sweat. The fluid wetting his pillow was making a mess and he couldn’t help drooling into his actual pillow. Gods, he’d need a shower tomorrow. Heat started to coil in his belly as he humped his pillow desperately. He was getting close, faster than he thought he would. A few thrusts later and he was muffling a moan into his pillow. His thighs tensed, hole clenching around nothing and dick twitching as he came all over his pillow. The pillow was effectively ruined by the amount of slick he’d managed to get on it. It soaked the cotton, his legs, and his trimmed pubic hair. Coming down from his orgasm let him ignore the mess for a little while longer. He used the pillow to wipe up what he could before tossing it towards the laundry basket. Exhaustion overtook him soon after and he managed only a brief glance at his clock before he passed out. 11:51 wasn’t too bad. Six hours of sleep might be worth it for the orgasm he’d just had. Definitely worth it.