What a Boy Wants Ch. 02

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Robert’s desires are not easily fulfilled.
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Part 2 of the 3 part series

Updated 01/24/2024
Created 12/14/2023
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Warning, the following story contains acts of anal rape and drugging. The author believes that consent is required from both parties, verbally, and does not condone lack of consent. All characters in the story are above the age of 18.

It had been two weeks since the first straight man Robert had converted. This time he was prepared for so much more. His sexual curiosities of the limits of the male body would not be unknown to him forever. He inspected his sex dungeon one last time before heading out to collect another soul.

Once satisfied that he was ready, Robert headed out to another college bar. It was a longer drive than he was used to, he wanted a fresh crop to choose from. Once he arrived he ordered a simple Jack on the rocks and scoped out the bar. There were plenty of women and plenty of men, but he was looking for a specific type. The type of man who would never admit to a homosexual desire. Soon he found one. He appeared to be a stereotypical jock. Robert caught his eye and waved him over and the jock proceeded to have a repulsed look and turn away.

"Yep, that's the one," Robert said to himself. He took a swig and headed over. It didn't take long to weasel his way into the jock's good graces. A simple 'didn't i see you at the last game?' and another 'you play really well, tell me your secrets' had this guy hooked into a conversation. Robert was aware that this jock, whom Robert learned goes by Chris, wouldn't come back to his home willingly. A simple slip over his drink was all it took to make him a bit more compliant. A few hours later and it would look like Robert and Chris were best buds to any stranger.

"Let me take you home man," Robert smirked. Chris nodded and slurred an agreement. Robert escorted Chris into his truck and then proceeded to ignore the slurry directions that Chris tried to give him and took him straight home. Once they got back to Robert's home Robert all but carried Chris inside and down into the basement.

"What is this?" Chris asked groggily.

"My house," Robert answered vaguely. He then guided Chris to straddle a chair resembling a chiropractor's table. "Why don't you lay down and I'll give you a massage?"

Chris was too inebriated to really protest. So he flopped face down and tried to get comfortable. He realized that unlike a chiropractors table, this one had a Y shape in the back, similar to backwards stirrups. He could feel a nook where his knees settled with joints on either end of the nook, as if made for him to bend his knees.

"What are these?" he asked Robert, feeling a slight bit clearer in his mind.

"The table can bend, makes the massage much more comfortable," Robert answers. Chris wasn't sure about this and tried to get up when he felt straps across his thighs tighten.

"What are you doing?" He shouted.

"Nothing at all," Robert cooed while he walked around and proceeded to tighten straps on Chris's calves. Chris tried to lean up, but Robert pushed him back down onto the table and strapped his arms to the arm rests.

"What..." Chris shouted out before Robert pushed a gag into his mouth.

"I'm going to make you beg for me," Robert ended before walking back around to Chris's back-side. Chris, realizing the trouble he's in, tries in vain to break free. He turns his head to see what Robert is doing. He can hear wheels along the stone floor and catches the glimpse of a cart. "Don't worry, I'll show you everything," Robert reassures when he sees Chris looking at him. As promised, Robert picks up and shows Chris a six inch glass shaft that is narrow at the top with a rounded point and about two inches thick at the base. Chris shakes his head as Robert rubs it down with oil. Robert straps a device to Chris's ass that keeps his cheeks spread wide open before he starts to insert the glass shaft. Chris groans and screams through his gag as he is stretched open by the unyielding force. It didn't take too long for the consistent feeding to reach its end. The glass shaft was cold inside Chris's rectum, which helped soothe the burning sensation. Once all six inches were in, Robert withdrew the shaft, then plunged it quickly back in, making Chris squeal. After pumping the glass shaft in and out a few times he pulled it out completely and admired the hole he had made. Unfortunately Chris's anal star was quickly recovering and closing. Chris felt something like ice being squeezed into his colon and realized it must be gel lube.

He turned his head in time to see Robert's own cock readying the plunge. It was nine inches long, nearly ten, and Chris shook his head. There was no way that would fit. "This is the least of your worries, I just need to get off real quick before we test your limits," Robert smirked and shoved himself in until he reached the six inch depth of the glass dildo. Then he pulled out a little before pushing in harder and gradually plunging all nine inches in. Chris's colon cramped and he felt twisting pain inside his belly. Robert held himself there for only a minute before he pulled almost all the way out and plunged rapidly back in. Robert kept his pace up, rapid in and out successions, until he felt Chris's anal passage clench around him as Chris had his first orgasm. Robert pushed in, hard, trying to get as much of himself in as possible, before he too squirted himself deep inside Chris. Chris moaned through their collected orgasm and Robert smiled. He was already winning this one over. Once he was spent he pumped a few times so the vacuum of Chris's colon would suck some of his semen deeper inside him. Once he pulled out, Chris whimpered at the air that flowed in.

"Don't worry, you won't be empty long, I want to see how deep you can take it," Robert chuckled at his own joke before he pulled out a twelve inch dildo. "This isn't the biggest I have, but I want to see step by step," Robert explained. Chris whimpered as Robert stuffed the dildo into his ass. He cried out as this one was thicker at the tip than the glass shaft or Robert's dick. Once nine of the twelve inches were in there was a bit of resistance, but it wasn't a 'go no further' kind, so Robert leaned into it and pushed the last three inches in. Robert held it there, letting Chris get used to it before he started moving it again. Chris moaned and groaned at the progressing dildo as Robert withdrew and pushed it back in. A few in and out's later and the fight was more like a glide. Robert had successfully stretched this guy to a twelve inch dick. Robert pumped the dildo until Chris had orgasmed a second time.

"Yeah, cum for me, admit you like it," Robert cooed. Robert pulled out the dildo and squirted more lube gel into the gaping opening before he set the twelve inch down and picked up one that flopped over in his hands. Chris tried to squirm away when he saw it, but he wasn't going anywhere. Robert cranked the cheek spreader wider and placed the tip of the horse dildo on Chris's anus. Chris shouted through his gag, screamed in protest. Anything to make Robert change his mind, but Robert wanted to know if it would fit. This sixteen inch dildo, three inches around at the thinnest point and five inches at the thickest, was the largest dildo that Robert had right now, and he needed to know if the human body could take it.

Robert pushed and the dildo folded, so Robert had to hold it straight for it to slip in. It popped in with a few inches following and a loud groan came from Chris as he cummed from this action alone. Robert smiled and pushed the horse cock in up to the eight inch mark through Chris's orgasm, making it last longer that either of them thought possible. As soon as his orgasm relaxed, Robert twisted and pushed the dildo in farther until it reached the twelve inches that had been reached before. Chris felt a cramping in his gut again and had a flitting wonder at how much he could take, but he pushed the thought away.

"Oh relax, you can take it," Robert smirked. He pushed harder and another inch was dragged in, then another. Two more to go, but Robert was feeling serious resistance, like Chis's bowels couldn't take any more. He twisted the dildo, but it wouldn't go further. He stepped back and looked at his predicament. Then the idea came to him and he readjusted the legs so that Chris's knees dropped into a bent position. With this new position, Robert was able to change his angle and work the last two inches into Chris's colon. He moaned in pain as he felt it creep around the bend in his intestine. Robert cheered when all sixteen inches disappeared into Chris's ass. When Robert pulled the dildo out slowly he could feel it being pushed out by the pressure. He only pulled it half out before pushing it all the way back in. Chris couldn't take it and orgasmed again. This was perhaps the strongest orgasm that Chris had ever had, and all from this anal fucking.

There was also another secret to this special order dildo, that Robert couldn't wait to use, it had a channel to feed liquid through it. For this specifically, Robert had saved up his own semen and poured it through the horse dildo, down the sixteen inches, and deep into Chris's bowels. Chris could feel the liquid flow around the curve of his intestines and could feel his stomach bulge as a gallon of semen was dumped into the deepest part of him. At one point there was a bit of back flow, but Robert didn't want any of it to go to waste and used a perfect fit rod to feed in and pushed the liquid deeper. Chris cummed again at the feeling inside him and Robert pumped the cock a few times to push his seed deeper before he finished pouring the remaining half gallon of himself into Chris. He had to push the rod down and push his semen deep a few times before the entire gallon was successfully poured into Chris's ass.

Robert let it sit there, pumping the horse cock to plunge his sperm as deep and as through Chris's colon as possible, before he slowly pulled the cock out and pushed it back in and started to fuck Chris with it in long and quick strokes. After a few minutes he wanted another taste and yanked it out before replacing his own cock into Chris's ass and thrusting rapidly, but the seal wasn't tight enough. Robert never broke a sweat as he grabbed a long and thin fourteen inch dildo and shoved it in alongside his own cock. Chris moaned and cummed again. Robert pushed the dildo in as far as it would go and kept pumping himself in and out, now feeling the tightness around himself. He did this until he cummed again, then he pulled out and plugged Chris's ass with the appropriate sized plug. Chris was ashamed by his satisfaction from the events that just took place.

A few hours later Robert drained Chris and then let him go. Chris staggered out and gingerly got into the cap that had been called for him, looking back briefly at the man that had just broadened his perspectives before shaking his head and turning away. Robert smiled as he thought about how he couldn't wait to try out another.

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