Encounter

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Drew's lubed up hand was having its desired effect and it wasn't long before Gregory was almost squirming from the feelings it generated, he laid his head back on Drew and groaned deep in his throat.

'Carry on like that and I'm going to come.'

'Good, that's what I want.' Gregory could hear the smile in Drew's voice.

'But you'll get nothing out of it.'

'There's time enough.'

Gregory let himself be swept away on the sensation of that slippery hand sliding more and more urgently up and down his shaft, feeling the heat and pressure building in his balls, promising himself that he would repay Drew for this pleasure. He felt his balls tighten.

'It's going to happen.' He warned.

Drew replied by running his lips over the nape of Gregory's neck and wanking him even harder.

'I'm coming.'

He couldn't help it, he found himself grabbing hold of Drew's knees and gripping them tight as he levered himself off the bed and towards that bliss making hand. Drew suddenly tightened his grip and ran his fingers slowly and firmly along Gregory's shaft as if milking him of his cream. That was enough; Gregory squeezed his eyes tight shut, moaned plaintively and exploded, his cum shooting in great strings and gouts, spraying the bed, his own belly and Drew's hand in spurt after spurt.

When his spurts finally trailed away into little dribbles that welled out of his cock and ran down his shaft he slumped back against Drew, his heart hammering and his breathing harsh and laboured. Drew reached out again, this time for tissues with which to wipe his hands.

Gregory was too spent to do anything for the moment, and so Drew finally did it for him, cleaning the cum from his belly before gently wiping his rapidly deflating and very sensitive cock, the sensation making Gregory flinch and gasp and making Drew chuckle.

'Wriggle down a little bit.' Drew instructed.

Gregory looked back and silently did as he was told, unable yet to speak and ask why as he shuffled a couple of feet down the bed, feeling Drew's erection spring free behind him.

Drew swung his leg over Gregory's head and lay down beside him, slinging an arm over Gregory's shoulders and hugging him.

'Are you sure you're okay with this?' He asked, looking down into Gregory's eyes.

'Yes, I'm fine.'

Gregory nodded and smiled, his breathing now more or less under control. How could he not be okay with such a thrilling experience? He looked at Drew's cock, still hard and erect - and waiting.

'Can I do it to you?'

'You don't expect me to say no, do you?' Drew grinned and then his face went serious again. 'As long as you want to. I mean, I know you've not done anything like that before.'

'I know, but I'd like to.'

He wanted to see what he was doing, to get an extra thrill from watching, and so he inched his way down a little further and then reached out for Drew's cock, his heart pounding again from sudden excitement as his fingers closed around the hard warm flesh. It felt so different from his own, not just because it was that little bit thicker, or because Drew was circumcised, but because he was only feeling one side of things. Instead of feeling his fingers through his cock and his cock under his fingers, he was feeling just the skin of Drew's cock twitching slightly from arousal, and instead of both blood pumping through his cock and throbbing under his fingers, he was feeling only the throbbing, the urgent needy throbbing. He savoured the sensation for a moment or so and then began to run his fingers up and down its length. Drew rested back and groaned his approval.

At first Gregory simply explored Drew's cock, running his fingers over it, stroking its head, circling its base, fingertips scratching through its hairy nest and then pushing down to cup and fondle the sac below, feeling Drew's balls roll under his fingers. He looked up to see that Drew's eyes were closed and his mouth was open just enough for little sighs of contentment to escape and he smiled to himself, surprised at being able to please another man so easily, and at getting so much enjoyment himself at doing so.

Then, encouraged by Drew's reactions, he closed his hand around Drew's shaft and ran his hand along it, up and down, playing with it just as he would his own, gazing at the circumcised head and wondering vaguely about Drew's religion. Not that it mattered of course.

It did look nice though, a clean, vein threaded shaft topped with a slightly darker, shining mushroom of flesh. He'd often wondered what another man's cock was like, what it felt like, and more besides. He looked at it and wondered if he should, or if he could. He felt excitement well up inside him, making his heart hammer once more in expectation. Why not, he asked himself and leaned over, opening his mouth and taking Drew's cock inside it.

He was surprised at the sensation, it felt warm, hot almost, firm but not solid, but most of all he was surprised at the how much it filled his mouth. He had never realised just how relatively big a man's cock was, until now. Nevertheless, it felt good in his mouth. He swirled his tongue around the tip, licking it, using the flat of his tongue under the glans, his lips closing under the mushroom head and moving up and down the first inch or so of Drew's shaft.

There was no particular taste that he could discern, although he knew there would be there would be if - or when - Drew came, and he suddenly wanted to taste him. He sucked hard and pumped faster, wanting to make him come, wanting to feel that surge of spunk flood into his mouth, but he was filled with trepidation all the same.

Yes, he'd thought about giving another man a wank, but he'd never expected to be doing it. He'd been curious as to what it would be like to have a man come in his mouth, but never thought it likely to happen. But now it was going to, and he was both very excited and extremely frightened. In the back of his mind a little voice was shouting to make itself heard, telling him that it wasn't right, he shouldn't be doing it, not with another man. But he was doing it and his excitement was telling that voice to be quiet. There was, he told himself, nothing wrong with pushing at his own personal boundaries now and then.

Drew was beginning to squirm as his body began to respond to Gregory's attentions, screwing up his face, gripping the bed and Gregory's shoulder, his breath coming out in little explosive gasps as his climax started to build. When he had seen Gregory in the park he had hoped, but not really expected, to get to this point, and even if he had, he hadn't expected the man to be so damn good at it. He wondered if he might yet take things even further. He groaned at the thought and his climax got closer.

Gregory felt Drew start to tense and knew that it was soon going to happen. He worked harder with his tongue, squeezing a little tighter on Drew's shaft with his fingers and prepared himself mentally to have a man come in his mouth. He was still nervous, but he was determined for it to happen. One experiment was not going to make him gay, not going to prevent him wanting a woman afterwards, and he knew that if he chickened out then he would always wonder, always reproach himself for being a wimp, for he was unlikely ever again to get the chance. He was going to do it and, he resolved, he was going to swallow.

Drew's fingers gripped harder onto Gregory's shoulder as his pelvis began to shudder and he began a series of low urgent grunts. Gregory tensed himself ready for Drew to shoot his load directly into his mouth, but then, just as he felt Drew's cock twitch and swell beneath his fingers, his nerve broke and he snatched his mouth away.

He was just in time; the first spurt hit his cheek, splashing the side of his face with hot spunk. Drew groaned in disappointment, making Gregory feel both guilty and angry with himself for backing off when he had wanted to do it so much. He looked down just as a second spurt spattered his shoulder and neck. He didn't even think about it, he just had to do it or he would never forgive himself. He made himself lean back down and close his mouth over Drew's cock just in time to receive the third, slightly smaller spurt.

It felt good to feel warm spunk flood into his mouth. He had never tasted spunk, not even his own, and didn't know what to expect, but it tasted good, slightly salty, slightly acerbic, and such a turn on. Even though he had not long come himself, he felt himself becoming aroused once again. Now, as Drew's spurts became smaller and smaller as his climax passed, he regretted his weakness and promised himself that next time he would take all of it, and willingly. Next time! He suddenly realised what he had promised himself and smiled around the head of Drew's cock as he licked away the remains of his climax.

'I'm sorry Drew.' He apologised. 'I guess I just wasn't as brave as I thought.'

'No problem.' Drew was still breathing heavily, his chest heaving as he gasped around the words. 'I was nervous on my first time too.'

Gregory relaxed onto his back beside Drew and turned his head to watch him struggle to regain his composure. Eventually Drew took a deep breath and smiled back at him.

'Phew. That was good. I bet you can use a beer now.' He clambered from the bed without waiting for an answer.

Gregory watched Drew saunter out of the bedroom, taking in his rear view and thinking how much more attractive a man's body was after you'd got to know it more intimately. He giggled softly to himself at his thoughts.

Drew came back with a couple of opened bottles and wandered back to the bed, his cock swaying gently as he walked. Gregory was looking at it so intently, half wondering how long it would take to get hard again, that he almost didn't see the bottle that Drew held out to him.

'Sorry.' He apologised again. 'I was just wondering something.'

'Oh, right. No worries. What?'

'Oh, nothing much. I'll tell you another time.'

'Do a lot of that wondering, do you?' Drew asked, smiling and teasing.

'Not usually. Thanks for the beer.' Gregory saluted Drew with the bottle and took a long pull on it to try and divert the conversation.

Drew saluted back and the two men lounged side by side, still naked, each lost in his own thoughts as he drank his beer. Eventually Drew finished his and leaned out to put the bottle down beside the bed, prompting Gregory to do the same.

'I was ready for that' Drew announced.

'Me too.'

They lay companionably side by side for another few minutes, still not speaking, neither really knowing what to say. Drew reached out and laid his hand on Gregory's stomach, the fingertips just resting on his limp cock, a silent signal that the day was not yet over. Gregory glanced across and smiled, reaching out his own hand and finding to his satisfying surprise that Drew already had a semi hard. He stroked it with the tips of his fingers, feeling both it and his own begin to fill out.

'Do you want to tell me what you were wondering a bit back?' Drew asked, somehow sensing that it had been to do with him.

Gregory looked across at him silently for a long hard minute before he answered. Today had been a revelation, bringing him into an understanding of his own tendencies, his own curiosity, showing him that it had not been quite the idle curiosity that he had always believed. He was still nervous, very nervous, but he accepted his feelings now. He had almost chickened out of letting Drew come in his mouth and now he wanted to go the extra distance – if he could raise the nerve.

'I was wondering if you would like to fuck me, and what it would be like.'

'Do you want me to?' Drew asked. His cock twitched in anticipation under Gregory's fingers.

There was another long pause.

'Yes.'

'Sure?'

'Yes.'

'Face to face or from behind?'

The choice threw Gregory for a moment. He wasn't sure how face to face would work, although it obviously would. But he'd expected to be kneeling and so he chose that way.

'From behind.'

He could feel that Drew's cock was nearly fully hard now, although his own had yet to respond fully. Without being asked he rolled over and got onto his hands and knees. He felt himself trembling slightly, not knowing if it was from fear, anticipation or just plain excitement. He looked sideways at Drew, his eyes taking in the cock that he wanted inside him, and his head tilted slightly as if to ask Drew what he was waiting for. Drew rolled over and reached out, picked up the lube and then scrabbled in the drawer once more, finding and extracting a condom. Just for a second Gregory felt disappointed that something was to get between his body and that rush of spunk that he had been expecting, but then commonsense prevailed and he acknowledged to himself that he knew hardly anything about his new partner. Time enough when they knew more about each other he thought, not realising that he had already assumed it would happen again.

Drew shuffled around behind and Gregory heard the little packet being ripped open and the elastic sound of a condom being put in place. He waited patiently with mounting excitement for the experience to begin.

Gregory jumped slightly with surprise as Drew spread cold lube around the entrance to his anus, inserting a finger and wiggling it around a little, spreading it into his passage and prompting a murmur of excitement. He felt the finger push in and out several times and then it became still, just inside him. He wondered why, but before he could express his disappointment he felt another being inserted gently alongside the first, opening him a little bit. He was being stretched ready he suddenly realised and let out a long low sigh of pleasure. It felt nice having two fingers playing in that forbidden place and he instinctively pushed back towards them, making them enter him as far as they were able.

After a moment or two the fingers were withdrawn and he heard movement behind him, the cap of the lube being closed and then odd, unidentifiable wet noises. He waited, crouching on his hands and knees, wondering what Drew was doing before he suddenly realised that he was applying extra lube to his condom enclosed cock, making it slippery enough to enter him easily. His heart thudded eagerly as he heard Drew shuffle into position behind him, a slightly cool steadying hand being placed on one of his hips. He bent his arms, lowered his head and waited, resting on his elbows with his bottom raised. Drew's thumbs pressed his cheeks apart and he knew that Drew must be gazing at his anus and getting prepared to enter it.

'Ready?' Drew's voice was thick with arousal.

Gregory nodded and almost immediately felt the cool touch of Drew's rubber against his anus, and he tensed himself.

'Relax.' Came a hoarse instruction. 'Let it happen, it'll be more enjoyable then.'

Gregory tried to comply, but as he felt the tip of Drew's cock press against his entrance he had to fight the urge to tense up. His sphincter was being forced open, uncomfortably so, not hurting a lot yet, but promising a more intense pain to come. He whimpered softly with a cocktail of fear, anticipation and arousal. He closed his eyes, screwing his face up as he fought his instinct to pull away. He'd asked for it, literally, and he wanted it, and he was damn sure that all gay men didn't go through agonies every time, so why would he. He set himself rigid and let Drew press harder.

It seemed like forever before his sphincter finally relented and Drew's cock slid into his passage. The penetration hurt, a hot pain like a Chinese burn in his backside, but it wasn't as bad as he had imagined, and he was over the worst. Now that Drew had actually entered him, he knew it would only get better. He relaxed a little letting his eyes open and his breath escape, feeling the discomfort diminish along with his tension. He glanced back down under his body, expecting to see his cock flaccid and tiny in comparison with Drew's, and surprised to see it was still half hard. Drew paused now, holding himself still with just the head of his cock inside Gregory's rectum.

'You okay?' Drew's voice was low and tight.

Gregory nodded, a quick little nod before he changed his mind.

'Yes, fine.' He gasped. 'Go ahead.'

He felt Drew move behind him, adjusting his position, coming a bit closer and taking hold of his hips. Drew pushed, and Gregory felt the full length of his cock slide deeper until pubic hair brushed against his skin and he knew that Drew was all the way inside him. He smiled inside, excited and relieved to have finally done it. Now he knew what it felt like to have man inside him, and it was good. The pain had gone, disappearing as his sphincter had got used to the invasion and relaxed, and now all he felt was a wonderfully strange feeling of fullness and a lot of satisfaction.

'That's so fucking good.' He felt he had to let Drew know how much he was enjoying it.

Drew's fingers squeezed his hips briefly in acknowledgement and then he began to thrust, pushing in and out of Gregory's rectum, pulling right back only to plunge forward and drive his cock back deep inside. Gregory gasped with pleasure each time Drew drove in deep and slammed his body against his behind, part of the enjoyment coming from the sensation and part from knowing he was pleasing his partner.

He dropped his head to look back under himself, confirming to himself what he felt, that his cock was now rigidly erect. He could sense that his balls were refilling rapidly and he wondered if he could reach back and wank himself while he was being fucked, but he didn't dare try. He didn't want anything to spoil what was happening. Drew's strokes were getting faster and harder, and Gregory could tell that he was getting close.

Drew was gripping hard onto Gregory's hips, holding himself in, pulling Gregory back onto his cock, thrusting madly as his climax approached and making Gregory tense himself. He was holding his body stiff and unyielding to prevent himself from being pushed flat on the bed by Drew's frantic movements and his arms were beginning to ache. But he didn't care, he loved it and all he cared about was remaining still long enough for Drew to climax. He folded his arms, lowering his face to the bed and let it happen.

Drew's thrusts were becoming erratic and jerky and he was making little grunts and gasps as he got closer, his fingers digging painfully into Gregory hips.

'I'm gonna come.' He moaned, warning Gregory of his imminent climax.

'Good.' Gregory gasped his answer. 'Shoot it up me.'

In his excitement he had forgotten about Drew's condom.

Drew groaned and rammed his cock as far into Gregory as he could, even wriggling his hips as if to screw himself deeper, and then he came, his cock twitching inside Gregory as he filled his rubber with burst after burst of his cream, all the time grinding his pubes onto Gregory's soft backside. He relaxed and pulled back just a little bit between spurts, only to slam himself forward again each time his cock sprayed more cum.

Gregory set himself solid, receiving Drew's assault with excited fulfilment. Over the years he had fantasized about this moment, denting to himself that it was anything more than curiosity. But now it was happening and as he was buffeted and battered he was almost grinning with exhilaration and satisfaction. He was going to be sore afterwards, he was sure. But so what, it was small price to pay to have his most secret wish realized.

Soon Drew had finished and he slumped forward, leaning against Gregory's raised bottom for a minute or so before pulling away, his rapidly softening rubber enclosed cock sliding out of Gregory reluctantly, the head being held briefly by the ring of the sphincter muscle before pulling clear.

As Drew pulled out Gregory sagged forward onto the bed, sprawling out full length as if spent, his own breathing nearly as rapid and heavy as Drew's. Behind him he heard the stretch and snap of a condom being removed and tied off, and regretted that it had deprived him off the one thrill he had yet to enjoy. Another day, he thought, another day.

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18 Comments
edgrantedgrant6 months ago

Still oh so curious. I wonder if "it" will ever happen. Loved how the story developed and the excellent descriptions of finally experiencing being with another Man. As a story, I would have loved to have read that Gregory was inseminated. Great writing. I will be reading some of your other posts in a moment.

AnonymousAnonymousalmost 2 years ago

OMG

I would luv to be Gregory in this story, although I’m certain that it would hurt more than as described but I have been so curious about this for so long I know that I want to experience this at least once with a kind gentle man like Drew. I live in hope.

dirtyoldbimandirtyoldbimanalmost 2 years ago

why do I identify more with Gregory than Drew? Oh yes, been there done that.

Metoo1202Metoo1202almost 6 years ago

Love the story gave me a hard on thinking about going to a park tomorrow but I don't know if there's any way that hangs out there for sex just going to have to go try and see what happens cuz I'm willing I haven't done it in a long time but I can't wait to try it again if anybody lives in the Norwich area Connecticut I'd like to meet you. Me-too1202 send me an email

AnonymousAnonymousover 6 years ago
Beautiful story

By the time I had finished reading I'd cum twice and was getting hard again !!.. so reminiscent of my 2nd time with a man when I Was 19 ( the first was hurried , frantic and not very fulfilling )

This guy treated me like a ' lady' , paying attention to all my wishes and soothing any doubts I had ( he'd taken me back to his house in the suburbs ) as well as being kind, he was also gentle .. I didn't realise he was all the way in until he told me ( and he had a fairly big cock too - almost 8 inches ) .. he made the experience memorable and fucked me beautifully on more than one ocassion

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