A gay story: A Young Man's Memorable First The young man trembled as he lay naked on the exam table. He knew what was coming, and he wasn’t quite sure if he wanted it or not. Hands stroked his naked thighs, stopping under the curve of his ass. He wasn’t sure how many other men were in the room with him, but since he felt three hands caressing his bare flesh, there had to be at least two of them.
He was laying face down on a special table made just for this occasion. His hands and legs were tied spread-eagle to limbs of the X-shaped table. The ties were leather cuffs with fur lining in them. He wasn’t being punished, and the men wanted to be sure that he was comfortable where he was. The cuffs had a few inches of give, so that he could wiggle and squirm on the table, just the way they liked it.
The man was pulled from his musings as warm gentle fingers touched his ass, rubbing in smaller and smaller circles until the pads of the fingers were approaching his tiny virgin hole. Two of the hands gently spread his ass open while a third set of fingers touched his small entrance for the first time.
He was a virgin in every sense of the word, he had never fucked or been fucked, and this experience was by far the most intense of his young life. The table he was laying on had a large hole for his very cock to dangle through, and this was lucky because right now he was hard enough to fuck concrete.
No one was touching his cock yet, and he wasn’t sure that they would at all. He had been told that it was possible for a man to orgasm just from having his prostate stimulated, and tonight, he was going to find out if that was true or not.
The fingers on his anus pressed slightly, and though they were not lubricated, the tip of one slid easily into his open hole. The second it entered him however, his ass clamped down hard on the intruder, and he could hear a gasp of surprise from the man whom the finger belonged to. The other men in the room chuckled, and he could hear two other voices.
Three, he told himself. There are three men here with me, and I’m going to be fucked by at least one of them. It was a sobering thought, and he could feel a shiver of fear travel from the bottom of his feet all the way up to his head. His cock however, did not deflate at all. Rather, it twitched in excited anticipation.
Meanwhile, the finger in his ass was withdrawn. He heard a soft click and immediately felt something warm slipping down his back. It was lube, and it was dripping easily into the cleft of his ass, where fingers were waiting to meet it. The fingers took up some of the lube and pressed it against his now tight hole. He tried to resist, but he was no match for the slippery liquid, and before he knew it a finger was pressing insistently into his body.
“Ooooh….” He cried out as the first invasion registered in his brain. He was not gagged, as the men wanted to be able to hear all of his cries and moans, but he had been instructed not to actually speak to them. He wondered briefly how he would be able to communicate that he was in pain, if it came to that, but the thought was banished from his mind as the finger in his ass continued its exploration.
It was pressed in slowly, though the lubricant allowed it to glide into his flesh very easily. The goal was clearly not to cause him pain, but to drive him out of his mind with pleasure. He was doubtful that they would be able to do that however, as so far all he felt was an unpleasant sensation of being full.
Hands were still holding his ass open as the finger inside of him began to slide back out again. More lube was added and the finger was diligently pressed back inside of him. It slide much more easily this time, meeting little resistance from his muscles. His cock bobbed in time with his heart beat, though nothing in his ass really felt good yet.
He could hear some faint murmurs above him, and he knew that the men in the room were giving each other instructions. They were also trying not to speak beyond what was absolutely necessary. After a few more shallow pumps the finger in his ass was removed, but the hands holding him only spread his cheeks wider apart. He wondered what was going to come next. He tried to relax as much as he could in his bonds. Whatever was coming, it was best that he not tense up.
But he did just that as something cold and metallic touched the cleft of his ass, just above his recently vacated hole. He jumped a little at the foreign touch, and the men laughed again. Whatever the object was it was slippery as it moved down to poke at his hole. The little ring of muscle began to twitch as the piece of metal was pushed against it.
It felt much thicker than a finger, though he couldn’t yet tell what it was. From the way it was being rubbed against him he could tell that at least part of it was rounded, and it was this part that the men were evidently trying to push inside of him. Finally, after a few moments of pressing, his ass gave way and with a small pop the object was lodged inside of him.
He cried out in pain, but it lasted only a second. His little ring had been stretched to allow the head of the object into him, but it was able to close around the rest of the toy. He knew now that it was a metal plug that had been inserted into his rectum. It was cold, but the heat of his ass was working on it, and before long it would be as hot as he was.
There was obviously some kind of handle on the toy, because the men seemed to be taking turns pulling on it. Letting him feel the bulbous head stretch him from the inside, but never actually leave his body. The sensation of being full was back, but this time he thought he could feel tendrils of some other sensation start to creep in. One of the playful tugs on its handle seemed to last longer than the others; he could feel his ass being stretched from the inside. And just when he thought that they would let go of the toy and let it sink back inside of him, it was pulled all of the way out.
This time he did not cry out, though he did take in a hissing breath of air through his teeth at the sharp stretching sensation. Before he really even had time to relax himself once more after the shock of being stretched, he felt warm living fingers enter him once again. There were two this time, and the wiggling sensation that they produced was decidedly odd.
He squirmed around a bit on the table, trying to get away from those fingers. The man who was working on him chuckled in a rich baritone voice, and hooked his fingers to pull his ass back to where it belonged. As he did so, the tips of his fingers brushed across a special spot deep inside of him that made him cry out for an entirely different reason.
It was like a bolt of electricity had been shot up his ass, lighting his nerves on fire in the best possible way. Suddenly, instead of trying to escape from the burrowing fingers, he was pressing back up against them, trying to get them to touch that spot again.
More lube was dripped onto his ass, and a third finger was added to the mix. Even with all of the lubrication it was painful as his ass stretched around this new intruder. But as soon as the three fingers were in him up to the knuckles, they began to search around once more for his prostate.
The man who was fingering him knew what he was doing, and before long his prostate was being teased mercilessly. His erection, which had flagged a bit due to the pain of being stretched was back full force. One of the men knelt down next to the table, and for the first time that night he felt something touch his cock. A warm hand stroked him briefly, running from his leaking tip to the root of his cock. But as the hand left him, he felt a curious tightening sensation around the base of his erection. A silicone cock ring had been put on him to ensure that he didn’t end the celebration early.
The fingers in his ass pumped in and out a few more times and were then withdrawn completely. His ass now felt empty, and he wondered what was going to fill him next. He didn’t have to wonder for long as he could hear and feel one of the men climbing up onto the table. The limbs that his legs were tied to were not as narrow as the ones in the front of the table, and there was plenty of room for a grown man to kneel there, cock in hand.
“Now listen up boy. I know we ain’t supposed to talk, but this is important, and I need you to hear it.” The pleasant Southern drawl was coming from the man immediately behind him. The one kneeling on the table. The one with his cock now pressed against his thighs.
“I don’t have a very big piece of equipment, but you’ve never been fucked ‘fore now, and this is still going to hurt like hell for you. I’m gonna be gentle as I can, but my cock is going to open you wide up, and you’re gonna feel it.” He could feel more lube being dripped directly onto his hole now. “Do me a favor boy, try not to hold yer breath.”
With those words a cock was pressed against his ass for the first time. His first reaction was to clamp his ass shut against the new intruder, but the man behind him was having none of that. He used his fingers to guide the plump head of his cock into the tight little hole, pressing forward. Between that onslaught and the slippery lube that had been fingered into him, he couldn’t offer up any more resistance. The thick cock-head slipped right into his hole, the ridges on the crown spreading his ring open wider than it had ever been before.
He couldn’t help himself then, he screamed. None of the men made any attempt to either sooth or silence him. Maybe they liked his screams. The cock in his ass did hold still however. The only part inside of him was the wide, flared head, and he could feel the ring of his ass throbbing around it.
He took a deep breath in and out, and nodded. The men took this as a signal to proceed, and the cock began to slide forward once again. The head had been the widest part, but that didn’t mean that the rest was easy going. He could feel every single inch as it slide further into his body, forcing open new parts of his ass.
Finally, after what seemed like a small eternity to him, he could feel thighs against his own, and he knew that the breaching process was over. There was another man laying on top of him, and a cock buried up to the root inside of his ass hole. He was no longer a virgin.
After a moment or two of stillness, the man began to withdraw his cock. Now that his hole had been fully breached, it was time for the fucking to begin. He wished that he had something to hold onto as the cock began to rock back and forth inside of him. The pain of the initial entry had subsided, but he still felt a burning sensation deep in his ass. His cock was still hard despite the pain, unable to go flaccid because of the ring which held it in check.
The man inside of him was careful not to let his thrusting get out of control. Each time he withdrew his cock he did so slowly, and he pressed back in at the same angel every time. Each new entry into his ass hurt, as muscles unused to being so roughly pulled apart were breached. But the pain was slowly fading becoming something else entirely.
Just as he thought that he could almost feel some pleasure from this act, the cock inside of him was forced as far as it would go, the root spreading him open just a fraction of an inch more. He cried out again as felt something hot being pumped into his ass, and realized that the man inside him was coming. After a moment, the man pulled his softening cock out with a ‘plop’, and he could feel warm cum slipping out of his hole.
It was a strange sensation, and the young man wasn’t sure that he liked it. But he only had to endure it for a moment or two before someone took a damp rag and gently cleaned him up. His cock was still hard as diamonds, and he squirmed uncomfortably under the gentle rubbing. He had started to enjoy the sensations of being opened, and was hoping that the night wasn’t over yet.
To his delight he felt someone else climbing up onto the table as soon as he was done being cleaned of his previous occupant’s cum. Another cock was quickly pressed to his slippery hole, and he was delighted to discover that this one was able to slip inside him much more quickly. There was still some pain, but the cum still inside of him provided an excellent lubricant for this new, slightly bigger cock.
He was able to take this second visitor to the root after only a few minutes of pressing in, and he quickly worked his way up to thrusting. This time the young man could actually feel his prostate being worked over by the new, thicker cock. The flared head brushed and scraped against his swollen spot with every thrust, and he could feel his own cock twitching in its restraint.
The new cock seemed to delight in long slow strokes that entered him from head to root in one delicious movement. He was moaning now, in time with each wonderful long-dicking stroke, and he was disappointed when he felt a new volley of cum entering his ass after only five minutes or so.
He groaned as this cock was withdrawn as well, but the next man must have been waiting very impatiently, because another cock was pressed up against his loose hole before he even had a chance to get cleaned off.
This cock was the thickest one yet, and he could feel the ring of his well worked ass opening around it. His moans were uncontrollable as the incredibly thick cock pressed relentlessly up against his prostate. He wasn’t in any pain now, and the pleasure that he was feeling in his ass seemed to radiate over his entire body.
“Oh… please.” He begged softly. He knew that he wasn’t supposed to speak, but he was beyond caring at that point. He needed to come and it needed to happen soon. He couldn’t take the short strong thrusts that the man inside him was delivering for much longer before he would have to release his own load of sperm. “I need….” A hand gently stroked his lower back and butt cheeks.
“Don’t worry boy.” A soft voice spoke near his ear. “We know what you need, and we’re going to give it to you soon.” These words were accompanied by a ragged cry as the man inside him emptied a truly impressive load of hot cum into his bowels. He groaned at the new sensation of being filled with the hot liquid.
The man pulled out rather unceremoniously and he squeaked as he could feel the hot cum starting to drip out of his ass. He waited for the sensation of the towel cleaning him up, but instead he felt two very thick fingers slip into his well worn ass. He was being fingered again, a bit roughly this time now that his ass had been well opened up.
He lost track of time as two fingers became three, and as three became four. There was some pain as the fourth finger was slipped into him, but it was nothing that he couldn’t handle. His ass was on fire with pleasure, and he felt that if he wasn’t allowed to come soon, he might burst with it.
“Alright boy, this is it.” He shivered all over with anticipation. He thought that he was finally going to be allowed to come, and a hand stroking his cock did nothing to convince him otherwise. But the men had other plans. The four fingers in his ass were giving his prostate a good work out, pressing and rubbing it as often as they could, but now they were withdrawing.
“Am I going to be fucked again?” he wondered. But not, that wasn’t a cock pressing against his hole now, it was the fingers again. Four of them pushed relentlessly into him, up until the knuckles.
“Okay, take it off.” One of the voices commanded, and much to his relief the young man felt the cock ring being unclasped from around the root of his dick. His cock throbbed in a pleasure so acute it was almost agony.
He was so focused on his cock that he didn’t notice what was happening to his ass until a thumb was tucked in under the fingers and pressed up and in. His ass had been well opened, and the lube and cum inside of him made the passage easier than it otherwise would have been. But he could still feel the painful sensation of his small little ring being forced open around a thick set of knuckles. The pressure on his ass was unbelievable, and just as he felt that they were going to split him open, the knuckles ‘popped’ into his ass, and the hole hand slid easily forward.
He screamed out in a mixture of pain and pleasure as his ring was forced open and the knuckles slid harshly over his prostate. He couldn’t help himself, his cock twitched and began to spew forth a larger load of cum than he had ever seen in his life. It felt as if it went on forever. And all the while the hand inside of his ass rocked back and forth, over his prostate, prolonging his already intense orgasm.
Finally, the flow of cum stopped, and his limp cock was left to drip cum onto the floor. The hand inside him had curled into a fist sometime during his monster orgasm, and was now rotating inside of him. But the young man didn’t notice at all. The world around him had gone black, and he had drifted into oblivion. Somewhere, an echoing laugh rang out. But that was okay. Everything, would be okay now.