Young Love

Dylan was very unsure how to approach this. They had done everything up to sex and he was frustrated with having to wait, but equally he didn’t want to scare his boyfriend away by being too forward. He hoped that the other was struggling with the same dilemma, so it was a little less awkward.
It had been nearly four months since they started dating; time enough for them to start considering it. They’d talked about it since the start of the second month but neither had been quite ready then. Now they were a committed couple it felt like the right time to start, the question was how to get over the first awkward hurdle.
He’d been planning this since they started discussing it. He hated the attendant mess of unprotected anal and, feeling more embarrassed than he thought possible, had bought a packet of condoms. The shop assistant had tried making small talk during the purchase but all he could do was mumble and turn red. He didn’t want the world knowing what his plans were.
Later, while he and Stevie were watching a film and snuggling, he saw his chance. Over the course of the film they both stripped and the cuddling and kissing became heavier until they were practically there. He may have lost his jeans but he’d kept the condom on the pillow and picked it up. “Umm…” he hesitated, finally picking it up and showing it to Stevie. “I want to…”
“So do I” his boyfriend admitted. Dylan had never been on top, despite having done it before, but something told him that Stevie wouldn’t be so comfortable in that position.
Still kissing and cuddling, he blindly removed and unrolled the condom, sliding it on. Too embarrassed to buy lube as well – he didn’t want the shopkeeper knowing he was gay – he’d just gone for the extra-safe, extra-lubed ones. It made the initial part a little more slippery and awkward, but once it was on Dylan felt a lot better.
Stevie was already on his front, waiting. Dylan leaned across him, nuzzling his neck and face. “I wish I could look you in the eye during” he mumbled in his ear. “You’re just too sexy.” His hard cock was rubbing between his boyfriend’s buttocks, but not yet in him. Stevie whined and arched his back.
“Please, I want it – you!” Dylan knelt back and repositioned, adding his own saliva to the ready-present lube. Before putting his cock in, Dylan used his fingers to ready him, being as gentle as possible. He didn’t want to hurt his virgin boyfriend more than necessary.
Stevie was soon moaning loud enough to wake the neighbourhood and that was his cue to enter him. “It might sting” he told him, easing himself in. Stevie’d said he was ready but still tensed up a little when he was penetrated. Once he got over the initial pain he would enjoy the intimacy.
Stevie felt like nothing he’d ever experienced. His hand was a poor substitute He’d tried fleshlights and his brother’s blow-up doll but neither had the warmth or sheer bliss of filling someone you loved.
Once Stevie was comfortable Dylan began to tentatively thrust into him, becoming increasingly confident with his boyfriend’s positive response. He held his boyfriend still and reached under to play with his cock, prompting a garbled string of declarations of love. “Ilaffyo too” he managed to reply, gripping his hip even tighter. Stevie whined and bit into the pillow, pushing back against Dylan.
His thrusts were no longer timid, but they were still irregular and not terribly deep. “Can take all o’ it…” Stevie hinted, encouraging Dylan to push his entire self into him. He did, making Stevie scream.
He wanted Stevie to come first and was working him over quite manically. Dylan could only hope he wasn’t being too rough, he wanted to have sex with him again, not scare him off. He listened to him, made sure there were no noises of pain. “Wan’ ‘oo t’come” he uttered in his ear. “Come for me bebe.” Stevie yelped as his balls were given a squeeze, then moaned as they were more gently cradled and fondled.
Not a minute later the older boy shot his load on the bed. Dylan came not long after, collapsing on his panting boyfriend. “I really love you” he repeated, feeling for his hand then holding it. “I really do.”