Regret

Jeremy loved feeling the weight of Chris’ body pressing him into the sweat-stained mattress. The 17-year-old was face-down, his arms pinned to his sides as Chris’s cock began to penetrate his tight ring. It hurt, but at the same time it sent a wave a pleasure through Jeremy.

“Oh fuck,” groaned Chris as he started thrusting in and out. Jeremy’s hole was loosened up now, and he felt his prostate being stimulated by the in-and-out motion of Chris’ penis. He felt Chris’ balls slapping against his ass as his friend’s excitement grew.

It never took Chris long to cum after he started fucking him. Jeremy could hear Chris panting as his thrusting grew more frantic. A spasm of pleasure erupted inside Jeremy as his prostate responded to being fucked.

“God, yeah!” shouted Chris as his cock exploded. He thrust several more times, gasping for breath. Then he slowly pulled out. “That was awesome,” he said, smiling, unrolling the condom from his dick, the white jizz visible at the bottom of the rubber. “Hey, what’s that under you? Is that cum?”

Jeremy got on his knees and looked down. A pool of semen had formed on the sheet. “Yeah, I shot a load too,” he said.

“Even without a cock?” asked Chris.

“Yeah, it squirts out of me just like before,” Jeremy said. “It just doesn’t feel as good.”

Jeremy fingered his crotch, scooping the last few drops of semen from the tip of his stump. Barely an inch long, the remnant of his penis was barely visible above his floppy balls. Once more, Jeremy felt a surge of regret about his decision to have a penectomy.

When did it begin, this obsession with hurting his cock? Jeremy could remember his mother scolding him when he was a small boy because he would pull on it until it became raw. When he was about 13, he pushed a thin knitting needle into his pisshole, not stopping until almost 3 inches of the needle was inside his urethra.

When puberty arrived, Jeremy’s obsession grew stronger. He would wrap strings around the base of his cock, turning it a dark purple before untying it. He experimented with pins, pushing them into the head of his cock until the pain grew too great. Once, he managed to decorate the top of his cock with six pins. Jeremy smiled as he looked at the drops of blood oozing from the wounds.

Discovering the Eunuch Archive was a turning point in his life. Just turned 16, Jeremy learned that his fascination with penis torture wasn’t unique. In fact, to his excitement, lots of guys had the same fantasy!

Jeremy spent hours at his computer, reading the penectomy stories. He’d lock his bedroom door and get naked, and then masturbate. Sometimes he’d cum three or four times a day. His keyboard would get sticky from the semen.

It was about this time that Jeremy began acting on his same-sex attractions. Chris was an attractive dark-haired boy who lived on the next street, and they began playing with each other’s bodies in Jeremy’s room. They eventually graduated to anal intercourse, but Jeremy was afraid to reveal his fascination with penis torture to his new fuck buddy.

As the months went by, it became clearer to Jeremy that he wouldn’t be able to feel content just by reading about penectomy. Torturing his cock was pleasurable, but not enough. Only by going all the way would he ever feel at peace.

Jeremy reached out through the Archive, chatting with men who knew about penectomy. He learned the dangers and problems of cutting off a cock. But those were just obstacles to be overcome, because nothing was going to stop him. Jeremy made up his mind that he would do it as soon as his parents went away for a weekend.

A few days before he planned to cut off his cock, Jeremy spent the afternoon at Chris’s house. They had just finished a round of fucking when Jeremy told Chris everything – his long held desire to lose his penis, and his plan to perform a penectomy on himself. Chris was shocked at first, but Jeremy was able to convince him that he had thought about it for years, and knew he had to do it.

“Well, how are you going to do it?” asked Chris.

Jeremy said he had gotten a lot of information from guys on the Archive. “I’m pretty sure I can do it safely by myself.”

“That’s crazy! You need to have somebody be there in case something goes wrong.”

“Well, who can I trust to be there?”

“I’ll do it. I’ll help you.”

Jeremy was overjoyed that Chris would be there. It made him much less scared to go ahead with it. Now he knew there would be no turning back.

On the night his parents were away on a weekend trip, Jeremy invited Chris to stay over at his house. He didn’t tell him that this would be the night he was going to lose his cock. But he knew that Chris would help him achieve his long-held goal before another day began.

Waiting for Chris to arrive, Jeremy stood before a mirror and undressed. He pulled his white t-shirt over his narrow shoulders, and looked at his smooth chest. His fingers pinched his small nipples, making them erect.

Jeremy undid the buttons on his 501s, and saw the bulge in his white briefs. And then he was naked, his cock jutting out firm, his balls pulled close to his body. A mixture of fear and excitement filled the boy as he began stroking his cock for the last time.

With his left hand, Jeremy squeezed his nipples, while his other hand jacked his uncut cock. A thin rope of pre-cum soon dripped to the carpet as his stroking became more frantic. The knowledge that this would be the last time that his semen would flow through his dick gave Jeremy the biggest sexual rush of his life.

Just as the doorbell rang, Jeremy’s cum splashed against the mirror. He cried out as three white ribbons erupted from his pisshole. As Jeremy caught his breath, he watched his semen slowly drip down the glass.

Chris was startled when Jeremy answered the door naked. “Jeez, hon!” he grinned, eyeing a drop of semen that still clung to the tip of Jeremy’s cock. “Couldn’t you wait until I got here?”

“I’m sorry,” Jeremy said sheepishly, closing the door.. “But the idea that I’m gonna lose my dick tonight got me too excited to wait. I had to jerk off.”

“Tonight? Are you serious?” asked Chris.

“Yeah I am. I want to do it right away. Right now.”

Chris had hoped that Jeremy would give up his obsession, but now he knew that it was much more than a fantasy. He didn’t want to be part of this, but he also didn’t want his friend to do it alone. “Okay. Let’s do it,” he said, kissing Jeremy on the lips.

Jeremy had prepared his bedroom for the operation. He had placed a shower curtain on the floor, and towels were stacked on the bed. “This is a catheter,” he said, holding up a plastic package. “I need you to help me put it in.”

Jeremy lay down on his bed, his legs hanging off the edge. Chris unwrapped the catheter and swabbed the end with KY lube. “Now, push it into the hole,” he said, holding his cock steady so Chris could insert the tube.

Jeremy shivered as the catheter disappeared down his cock. “Keep pushing until you see piss start to come up the tube,” he said. Finally, the catheter reached his bladder, and yellow liquid began to flow from his body, and drip into a plastic collecting bag.

Chris was handed a thin leather strap and began to wind it around the base of Jeremy’s cock. “Tighter. It has to be real tight to prevent the bleeding,” he told Chris. By the time he finished, Jeremy’s cock was tightly bound and purple from the blood trapped inside.

Chris picked up the knife and held it over a candle to sterilize it. “You need to cut it fast. I don’t know if I can stand it otherwise,” Jeremy said. Chris nodded as the blade sizzled from the heat.

“Okay, are you ready?” Chris asked.

“Yes, as ready as I’ll ever be,” said Jeremy, closing his eyes.

Chris put the edge of the knife just above the leather strap and touched the taut skin of Jeremy’s cock. Jeremy clutched the sheet on the bed and braced himself. “Now! Do it!” he shouted.

With a quick stroke, Chris slashed the knife across the underside of the shaft, spraying blood all over his t-shirt. “Oh fuck!” Jeremy screamed, his body spasming from the intense pain. Chris plunged the blade into the wound and with a few strokes severed the penis from the body.

“It’s over! Look!” he said. Jeremy opened his tear-filled eyes and saw Chris up holding the remains of his cock. Then he looked down and saw the leather strap still in place over the stump of the penis. There was less blood than he thought there’d be. And the intense pain was already easing now that his dick was gone.

Chris carefully bandaged the stump, noticing the catheter was still in place. He opened a bottle of scotch and had Jeremy drink as much as he could. Finally, Jeremy passed out from the shock of the penectomy and the alcohol.

Chris covered his friend with a blanket before looking at the severed cock again. It had shriveled a lot, and blood was still oozing from it. He picked it up with a washcloth and put it in a jar of alcohol, as Jeremy told him to do.

--To Be Continued --