Remaking a Boyfriend Pt. 02: Important Lessons

Ray awoke to the unfamiliar sight of the soft glow of predawn light from the window and a throbbing pain in his cock and balls. He instinctively grabbed them, only to be surprised by the feeling of warm metal. The surprise morphed into anger as he remembered the events of yesterday. The sharp ache at the base of his swollen penis showed no signs of abating. He immediately became worried that the cage was cutting off his circulation and causing permanent damage to his manhood. He reached for Allison's shoulder and harshly shook her awake.

"Allison, something's wrong!" he hissed.

Allison rolled over groggily and looked at him. "What's wrong, sweetie?" she croaked.

"I think the cage is too tight! It really hurts, I need to take it off now."

Allison grabbed the ring of the cage and pulled it upwards, taking a look at Ray's penis and testicles. "Ray it's just morning wood, honey. You'll be fine. Go back to sleep."

"No, babe, it really hurts. Please!" Ray pleaded.

Allison got up from the bed grumpily and walked out of the bedroom. Ray assumed she was getting the key, and realized that he didn't know where Allison was keeping it. When Allison came back, though, she had a plastic bag with ice in it. She wordlessly placed it on the underside of Ray's balls, causing him to jump with shock at the cold. She climbed back into bed and rolled away from Ray. He was about to complain, but almost immediately he began to feel the pain ease as his penis began to shrink. Within five minutes, his dick was back to a completely flaccid state and the pain was gone. He faded in and out of sleep for another hour or so before finally getting up.

Being that this was earlier than his usual morning wake up, Allison was still in the kitchen, and Ray came in just as she was pouring him a smoothie.

"Morning!" she greeted him.

He mumbled groggily at her.

"You know Ray, since you're up early, maybe you could go for a run before breakfast."

"That's ok," Ray said sleepily. Allison cocked an eyebrow at him, and Ray realized that this wasn't a request. "Fine," he sighed. "But you have to take this chastity thing off me."

"But I have to leave for work soon, honey," Allison replied. "Tell you what: you try running with it today, and if it's horribly uncomfortable we'll figure out a way for you to take it off the next time you run. OK?"

Ray thought this was ridiculous, but he was too sleepy to argue. "I guess," he relented.

"Don't forget your fitness band!" Allison said as he shuffled off to get changed.

While the chastity device first felt slightly awkward during his run, after a few minutes Ray had to admit that it wasn't much of an encumbrance. He decided not to fight Allison about wearing it for exercise; he was realizing it was important to pick his battles. He ran a mile and a half, and despite it being unusually early for him to up and active he found the run to be noticeably easier. It was a good feeling. He returned home to find Allison gone and a note in her handwriting by his smoothie. It read, "Hi Sweetie! Hope your run went well. Lunch is in the fridge. Have a good day! -A"

Ray slurped down his smoothie and took a shower. He found washing inside the chastity cage annoyingly time-consuming. After getting dressed, he sat down to work. The morning flew by as Ray was busy, a little after noon he ate the salad Allison had left for him in the fridge. Shortly after that, he received an email from Allison. She wanted him to have dinner ready when she got home, and gave him a recipe for a simple chicken and vegetable dish. Ray worked a couple more hours, then decided he had been productive enough and went shopping for dinner. It was an odd feeling being in public with the weight of the chastity cage on his cock; he felt like he had an exciting secret, but it was also slightly embarrassing.

Back home, Ray began preparing dinner. He was nowhere near as good a cook as Allison, but he was still competent in the kitchen. Allison arrived home right as everything was finishing up, and Ray felt proud that he had something to offer her after her day at work. They drank a glass of wine with dinner and Allison vented about a frustrating situation at her office. Afterwards they watched a romantic comedy on Netflix and went to bed early.

The next day was similar. Ray awoke early to a painful erection (or at least an attempt at one), and got up to ice his groin. He went for a run before breakfast at Allison's suggestion. His day consisted of the increasingly familiar routine of having a smoothie, working, eating the lunch Allison had prepared for him, working a little more, and then preparing a dinner recipe that Allison sent him. When Allison got home, they ate and chatted lightly, until Allison's face went serious and she collected herself.

"Ray, I want to talk to ask you about something," she said.

"Sure, go ahead," Ray said nervously.

"I noticed you haven't looked at any porn the past couple days. Is there a reason for that?"

"I, uh," Ray stammered, caught off guard. "I just, I've been busy I guess."

"Are you sure it's not because you know I'm watching?" Allison asked. "How often would you go two days without looking at porn before our new arrangement?"

Ray thought about how to answer this, and decided that he wasn't going to get away with lying. "Never," he said truthfully.

"Thanks for being honest, honey. The point is, I don't want you to stop looking at porn! I installed that software because I want to know what you look at and what you like. Do you understand?"

Ray nodded.

"OK. All I want is for you to be honest with me and with yourself."

Allison's words of compassion struck a chord with Ray. It made him so happy to hear her concern for him and their relationship. He got out of his chair and hugged Allison. They kissed slowly and deeply. Ray could feel his arousal building but it was oddly blunted by cage restraining his erection—it simmered rather than boiling over into horniness. Previously he would have tried to escalate this into an attempt sex, but tonight he felt oddly content just to be around Allison and feel close to her.

**********

The next afternoon, after an unusually productive morning, Ray pressed send on a project he had been working on for weeks and felt a rush of relief. He had put in a lot of hard work for this client, and now that he was done he felt like taking a well-deserved break. Thinking about his conversation with Allison the night before, he opened a new browser and headed to his favorite porn site. He looked through categories for a bit and, remembering that Allison would see what he had watched, he settled on a top-end hi-def video of two attractive people having sensual intercourse. The girl in the video was smoking hot, and by the time she dropped to her knees to undo the guy's jeans, Ray's cock was already swelling in its cage. He pulled off his own pants and began to try to give it whatever stimulation he could through the cage, but it did little good. The pain of the cage tugging on his balls as his dick tried to harden only turned him on more. He closed the rather tame video he was watching and chose a new one that featured a tiny blonde girl getting pounded by a guy with an enormous cock. This only made Ray hornier, and he kept surfing for more intense videos, while at the same time trying to be mindful that'd he'd have to explain these choices to Allison.

Finally, when Ray was nearly delirious with horniness, he saw a thumbnail featuring a girl sucking dick with mascara running all down her face. Ray loved hardcore deepthroat videos full of spit and gagging, and despite not wanting Allison to know about this predilection his overwhelming sexual desire got the better of him. He clicked the video, in which a slim brunette was taking what had to be a ten inch dick all the way down her throat. Ray was seeing red trying to stimulate his cock through his cage, to no avail. He futilely tugged back and forth on the ring around part of the cage while the girl on screen had her face fucked by the massive rod. Her face became a mess of of spit and tears, and Ray was nearly in tears himself from his aching need to stroke his dick. Finally the video ended with a huge cumshot, which the girl played with and swallowed. As the screen went black, Ray began to feel creeping embarrassment about the fact that Allison would know he had watched the video. He closed the browser and went to go take a cold shower before he did anything he'd regret further. He spent the rest of the afternoon doing some laundry and idly worrying what Allison's reaction would be.

Allison arrived home a few hours later with a couple unmarked shopping bags. Ray decided not to bring up the porn and hope she wouldn't mention it, but after dinner she turned to him and cleared her throat.

"Ray, I saw that you looked at some pornography today," she said matter-of-factly.

Ray nodded. His heart began pounding.

"It's ok, sweetie. We discussed this. But Ray, I want you to tell me something."

"S-sure, anything," Ray stuttered.

"What video was your favorite? Which did you like the most?"

Ray hemmed and hawed. "I, uh, I don't know, all of them I guess."

Allison's voice lowered. "Are you sure about that Ray? What about the last video? Are you saying you didn't really like watching that slut get her throat filled with huge cock?"

Ray began to sweat and squirm uncomfortably. Allison's tone was scaring him a little, but he didn't want to lie to her. "I, uh, did like that."

Allison approached him and grabbed his caged penis through his pants. "Did you like watching her cry and gag as that huge dick fucked her little mouth?" she whispered into his ear.

Ray nearly melted. "Oh god, yes, I liked it so much. I wanted to cum so bad."

"Would you like to fuck my throat Ray?"

Ray closed his eyes and nodded. "Yes, yes, yes,"

Allison took a step back. "Well the good news is that you can, as long as you do something for me."

"Anything!" Ray said eagerly.

Allison led him into the bedroom and told him to close his eyes. Ray could hear Allison rustling through her shopping bags.

"The thing is, Ray, all men love girls who can deepthroat, but none of them realize how hard it is or what it feels like for the woman. It's just one more example of male selfishness. Not that it's not fun to suck cock, but a girl likes to have her skill appreciated. Open your eyes."

Ray opened his eyes and saw Allison standing in front of him wearing high heels, her bra and panties, and a bright pink strap-on dildo. Ray's eyes bugged out of his head.

Before he could say anything, Allison continued. "That's why you're going to learn to deepthroat a cock."

Ray opened his mouth to protest, but Allison brought her finger to her lips telling him to be quiet.

"I know you probably don't want to do this Ray, but you should know better than to object by now. I promise I won't hurt you, and you'll gain a new appreciation for what sex is like for women. And I think that's really important in developing your sexual confidence. Plus, I'll give you an amazing blowjob afterward."

Ray realized he had no choice, and nodded slowly. He was nervous, but he'd been dying for a real orgasm for days and the thought of Allison's mouth was worth it.

"Get on your knees," Allison ordered.

Ray knelt down slowly, and Allison stood over him, the pink dildo right at the level of his mouth. It hadn't looked huge at first, but at this close distance the size was intimidating. It was about 7 inches long and fairly thick. It had a stylized head that didn't look all that realistic but still reminded Ray uncomfortably of a penis.

"Now, Ray, I want you to slowly start licking and kissing the head of my dick."

Ray hesitantly stuck out his tongue and began to lick the dildo, which tasted vaguely plasticky. It felt weird, but Ray didn't want to disappoint Allison. He started kissing it, and opening his mouth around it.

"Very good," Allison said, "now put the head in your mouth and suck on it. And watch the teeth, nobody likes teeth during a blowjob."

Ray cringed at the word blowjob. Is that really what this was? Nevertheless, he opened his mouth and began sucking on the head of the dildo. It was uncomfortable to hold his mouth open so wide, so he frequently took the plastic cock out of his mouth to relax his jaw. It occurred to Ray that he had never actually considered that it might be uncomfortable for a woman to give a blowjob.

"Come on Ray, at least act like you're enjoying it. Nobody likes unenthusiastic head."

Ray began to vigorously bob his head up and down on the dildo. Taking a cue from all the porn he had seen, he put his hand in front of his mouth and stroked the dildo as he sucked it. Despite still feeling weird about sucking a plastic dick, his own cock began to harden in the chastity cage. He told himself that it was just from anticipating the blowjob he'd receive later and looked up at Allison, hoping she'd be pleased.

"Oh yeah, that's it Ray, you love my cock don't you?" said Allison.

After a second's delay, Ray managed an "mmm hmm" with the dildo still in his mouth.

"Now, Ray, I want you to slowly move the dildo into the back of your throat, and stop when you gag."

Ray did as she asked, and only got a few inches of the dildo in his mouth before he felt it at the back of his mouth and his gag reflex triggered. He jerked back and panted.

"Good job, baby," said Allison sweetly. "Now catch your breath and do it again. But this time, try to stop right before you gag and just let the cock sit in the back of your mouth."

Ray followed her instructions, pausing just when he felt himself about to gag, and waited. Slowly the need to gag began to fade.

"Now push a little deeper. You'll feel like it can't go any farther but just try to relax and breathe."

Ray pushed his head farther on the cock, but quickly gagged.

"Try again, Ray."

Ray again let the dildo rest in the back of his mouth before trying to push farther. He felt it hit the back of his throat and stop, then gagged again after a second. His mouth began to fill with thick spit.

"Again," Allison ordered.

After catching his breath, Ray again pushed the dildo into his mouth. This time, it made it all the way to the back of this throat without him gagging. But he couldn't get it to go any farther.

"Now," Allison said, "try to keep your throat open and wiggle back and forth as you try to push deeper. It'll take some force to get it into your throat but don't hurt yourself."

Ray did as she instructed, and felt the dildo began to slide down into his throat before he quickly gagged.

"You're almost there, sweetie! Keep trying!"

After a couple more attempts, Ray finally felt the dildo slide past the opening to his throat and down inside. It was a strange feeling. He could feel how tight his throat was around the dildo, and couldn't breathe. It was only a couple seconds before he had to pull away, gasping. He looked up to see Allison smiling at him.

"You're doing so good, Ray! Now, all you have to do is touch my stomach with your nose and we can move on to your reward."

Ray's throat was hurting but the promise of sexual release spurred him on. He kept pushing the dildo down into his throat, each time finding he was able to get farther. Finally, after about ten more attempts, he felt the dildo slide down his throat nearly unimpeded, and his nose buried into Allison's soft stomach. He immediately retched, and fell back panting as Allison clapped.

"That was so good Ray! You took that cock all the way down your throat. Now tell me, don't you have a better appreciation for women who can do that?"

Ray nodded, still catching his breath.

"With some more practice you'll be a real ace at it. Now, as promised, your reward. Lay on the bed and take your pants off."

Ray was puzzled by what Allison meant by more practice, but he was too focused on his reward to bring it up. He quickly obeyed her directions. Allison pulled her hair back into a ponytail and removed an anklet that Ray hadn't previously noticed. It had a small key attached to it, and it dawned on Ray that this was where she was keeping the key to his chastity device. She slowly unlocked his cage, and Ray's cock began to swell as soon as it was removed. Allison climbed onto the bed and straddled his knees.

"This may be a little different than you're used to, but I promise you'll enjoy it," Allison said with a smirk. She started gently rubbing Ray's penis with her hand, which was already enough for Ray to close his eyes and moan. His dick was already almost fully hard. Allison leaned down and softly took him into her mouth. The velvety sensation of her tongue on the underside of his shaft was overwhelming for Ray.

"Oh, fuck," he moaned, his hands gripping the sheets.

Allison slowly bobbed her head up and down for about a minute, after which Ray could already feel his orgasm building. Then, without warning, she moved her head down further, and Ray could feel the tip of his dick entering her throat. The warmth and pressure felt incredible. Allison pulled up and went back down, farther this time, making a wet noise when his cock passed the back of her mouth.

"Holy shit!" Ray gasped.

Allison continued, moving her throat up and down over his cock. As she did so, her hand moved to his balls, massaging them and rolling them around. Ray could barely see straight from pleasure. Allison pulled her head up just enough to catch her breath, but kept his cock firmly in her mouth, then went back to deepthroating him even harder. As she did so, the hand on his balls drifted down onto his taint. It felt ticklish, but Ray was barely able to breathe much less talk. He could feel his orgasm approaching quickly. A few seconds later, he felt Allison's hand move lower again, till her finger was touching his asshole. Before he could react, he felt a brief sharp pain as her finger pushed into his ass.

"What are you—" before he could finish expressing his surprise, he felt a deeply pleasurable pressure emanate from within his ass. He felt his face go flush, and his orgasm arrived like a freight train. His hips spasmed and bucked as he came, shooting his cum straight down Allison's throat. It was the most intense orgasm of his life. As he finished, Allison slowly pulled her finger out of his ass and let his deflating cock slide out of her mouth. She immediately gave him a sloppy kiss and shoved her tongue into his mouth. Ray tasted an unpleasant bitterness that he realized must be the remnants of his load, but he was too overwhelmed to object.

"What... what was that?" he managed to utter eventually.

"You mean the thing I did with my finger?" Allison asked coyly.

"Yes! Why did you do that? I don't like that kind of stuff."

"Oh calm down, Ray. It's called your prostate. It's like the male G spot. And if you didn't like it, why'd you come so quickly?"

"I, um..." Ray didn't want to admit that he had liked the feeling of having something in his butt, but also couldn't argue with Allison. "I guess it just took me by surprise."

"Lighten up, Ray! Sometimes surprises are fun!" Allison's smile was infectious.

"Yeah, I guess so." He smiled back. Allison kissed him, and in a swift motion put his chastity cage back on his penis, locked it, and put her anklet with the key back on. Ray slept soundly that night, feeling satisfied for the first time in days.

The rest of the week passed uneventfully, but when Saturday rolled around Allison said she had to go into work for a few hours to finish up an important project. Ray was bored being home alone, and, per his usual habits, started looking at porn. He again tried to steer clear of anything he'd have trouble explaining to Allison, sticking to softcore and vanilla videos. Eventually, though, his horniness started to get unbearable. He tried in vain to stimulate his dick through the cage, but it wasn't enough to get him close to orgasm. After about 15 minutes of frustrated fumbling, he realized that while his penis was still a little soft he could slip a finger in through the back of the cage. After playing for a few minutes, he realized that with some difficulty he could actually pull his penis out the back of the cage a little bit. As a test, he stopped watching porn and let himself go soft. Sure enough, he was able to pull it all the way out of the cage. Once he had done so, he immediately began to stroke himself. This was the longest he had gone without masturbating in years, and it felt incredible. He resumed watching porn, trying not to get too close to the edge and staying mindful that he'd have to explain his porn choices to Allison.