Remaking a Boyfriend Pt. 04: The Turning Point

Pt. 04: The Turning Point

Over the next month, Ray and Allison's love life settled into something of a groove. A couple times a week they would have sex at Allison's discretion, which meant either Ray eating Allison's pussy or Allison fucking Ray with a dildo. Ray was increasingly getting used to the strap-on, and starting to feel comfortable with it as a satisfying method of sex. If he was particularly horny he could even have something like a real orgasm, though Allison always found some reason to make him eat his semen as punishment when this happened. Ray also continued to watch porn frequently, and heeded Allison's advice to try and focus on what the men were doing. Eventually, his piercing healed enough for it to be taken out, though Allison insisted that it still wasn't safe for him to have sex or jack off yet. Allison swapped out his piercing for a slightly larger six gauge barbell, and his body gradually acclimated to the larger diameter.

While this new lifestyle would have been shocking to him a short time ago, Ray couldn't deny how much better his life was after deciding to do whatever Allison asked of him. His daily routine—a diet of a morning smoothie, lunch salad, and light dinner, plus the regular running and yoga, eight hours of sleep, and regular work hours—left him feeling productive and energetic. He was getting more work done, earning more money, and losing weight by the fistfuls. Once a fairly solid 175 pounds, he was now down to a trim 155 and could see the gentle definition of his muscles in the mirror.

The one part of his life that he did find frustrating was a nagging work project that he had been dealing with for months now. He had been contacted by a new and slightly mysterious client who had wanted him to make a logo for a fledgling woman's interest project.

Ray had started off designing something modern and minimal incorporating the female Venus symbol, which he was fairly proud of. But the client hated it and told him as much, saying that it looked too masculine. Ray tried again with a new design, this one an antique looking flower. He spent hours getting the colors exactly right, only to have the client reject it again, calling it too chaste.

This went on round after round, Ray's professional pride leading him to work harder and harder on new designs, only to have them rejected with terse explanations. But despite all the rejection, the client kept paying for Ray's time and requesting new designs. Eventually Ray had an idea that he particularly liked of a butterfly surrounded by stars. He couldn't explain why it made sense to him, but it felt right. Sure enough, the client finally liked it enough to not reject it outright. After round upon round of increasingly specific revisions, the design evolved into a brightly colored and elongated butterfly with stars on its wings, at which point the client finally sent him an email that read simply, "Perfect. Great work." Ray was ecstatic. It was the longest he had ever worked on a single project.

That night when Allison came home, he surprised her with an elaborate multi-course dinner and a nice bottle of wine to celebrate.

"What's the occasion?" Allison asked, able to read Ray's palpable excitement.

"Well, I finally finished a project for a really difficult client, and I'm really proud of the work I did." He went on to describe the entire process while Allison listened intently.

"That's so great, honey! I'm really proud of you," she said when he finished. "Coincidentally, I'm glad we're celebrating tonight because I just finished a big work project too. My team finally got a settlement on one of our biggest cases. 8.4 million dollars! More than anyone expected."

Ray went flush when he heard this. Here he was bragging about finishing a little drawing, and Allison was leading an entire legal team on a huge case. Still, he was incredibly proud of her, and they finished their dinner with both of them in a great mood.

"You know what?" Allison said as she finished her fruit tart dessert, "To celebrate both of our good weeks, I think we need to go shopping this weekend!"

"Oh, good idea! That sounds like fun," Ray replied.

"Especially with all the weight you've lost, you could use a whole new wardrobe."

"Hm, I have noticed that some of my clothes no longer fit very well."

"Plus, I think it's time we updated your look. I have a few ideas." Allison flashed him a mischievous smile.

"Well you know I trust you. Can't wait!"

That Saturday Ray woke up early and went for a five mile run. As he drank the coffee and smoothie Allison had prepared for him, they discussed their coming day of shopping.

"Should we go to the Northside Mall?" Ray suggested.

"Mmm, I think Lakeshore Mall has better stores," Allison countered.

"Sounds good."

"Also, I have an assignment for you. There's something I want you to do while we're shopping."

"Sure, what is it?" Ray asked hesitantly.

"Well, you know how you've been learning about how men can be good lovers by watching the men in porn?"

Ray nodded, still not sure where this was headed.

"I want you to do the same thing with how to look attractive. While we're shopping, I want you to try and notice how guys are dressed and what they do to look good."

Ray shrugged. "Sure, I guess that makes sense."

Allison smiled. "Great! Let's get ready then."

Ray put on a simple t-shirt and jeans, his standard outfit for running errands. Allison dressed in a light blue halter top, frilly white skirt, and three inch wedges. She looked fantastic, and Ray was proud to have her at his side as they strolled through the mall. It didn't escape Ray that multiple guys turned their heads at her wherever they went.

As they shopped, Allison explained to him that the style that would work best for his leaner body type was an edgier rock/punk look. Ray had never been one for flashy fashion statements, but he was enjoying the attention Allison paid him so much that he didn't object to her opinions. She took him to some of the more modern, glam stores, and picked out for him a wardrobe of skinny jeans, graphic tank tops and shirts, and patterned button ups, all well-fitted to his newly trim frame. She also got him a pair of nice black round-toe boots with a substantial heel, which he liked because they made him feel taller. Allison also got a few things for herself—a plaid miniskirt and some fishnet stockings that Ray practically salivated imagining on her.

After a couple of hours of shopping, they took their bags and sat down to eat some cheap Chinese food.

"So, honey, what do you think of your new wardrobe?"

"I really like it! I mean, it's a little more, um, ostentatious than I'm used to, but I'm excited to start dressing better for you."

Allison smiled. "You're sweet. Now, did you remember your assignment for the day?"

"Yeah, I mean, kinda. I tried to notice what other guys were wearing, but once we started buying a bunch of clothes I got pretty distracted."

"That's fair. Well, take a look around now and tell me what you see. Who do you think is the most attractive guy here?"

Ray scanned the food court, looking carefully at all the men in the vicinity. He felt unsure of himself, but finally he settled on a man sitting with two other guys to his left. "Um, that one over there," he said, pointing discreetly.

Allison turned her head deliberately and looked for a few seconds. Ray began to feel self-conscious. "The guy in the blue shirt?"

Ray nodded.

"Pretty good choice. What makes him hot?"

"Well, uh, he's tall, and he looks pretty muscular."

"How can you tell he's muscular?" Allison probed.

"Um, I guess because his clothes are kind of tight? You can see from the way his shirt fits."

"Exactly. He's wearing clothes that complement his body well. That's what I'm trying to help you with. Of course, you're not as muscular as him, so you'll want to wear a different style of clothes."

"Gee, thanks," Ray said sarcastically.

Allison rolled her eyes. "Oh, relax. You know I think you're cute. And you're going to look even better with your new wardrobe."

Ray chafed at being called cute by his girlfriend after she was complimenting another man, but he knew it was a minor gripe and he let it go.

Allison looked back at the man in the blue shirt. "What else do you think makes him look good?"

Ray snuck another quick look at him. "He has a pretty nice beard and a good hairstyle." His brown hair was cut short, and styled with a little bit of gel, with a full, thick beard and no mustache. "It's well-groomed but still masculine."

"Good observation! You're really getting it," Allison said. She was still looking over at him.

"Quit staring!" Ray hissed. "He's going to notice us."

Allison laughed. "Oh, relax, no he's not. And so what if he does?"

Ray glanced at the man again, and sure enough he turned his head in their direction. Ray quickly looked down at his plate in front of him. "Shit, he saw me looking."

"Jesus, Ray, it's not a big deal."

They went back to their meal and started to plan the rest of their day, but a few minutes later Ray noticed someone approaching their table in his peripheral vision. It was the man in the blue shirt!

He cleared his throat, and both Ray and Allison turned towards him. "Sorry to interrupt your lunch," he said in a deep baritone with a slight southern twang. "Hi, I'm Trent."

"Hi Trent," Allison said, smiling. "I'm Allison and this is Ray."

"Looks like you two have had a busy day of shopping," Trent said, looking at their bags. "I just moved to this neighborhood and haven't been to this mall before, I was hoping you could point out where the movie theater is. This place is huge."

Allison gestured behind her. "Down that direction, to the right when you get to the department store. What movie are you seeing?"

"Not sure, I was planning to go take a look and see if I saw something I liked," Trent said, grinning as he stared at Allison.

"Well, I hope you see something you like," Allison responded coyly. "Maybe one of the new superhero movies."

Trent chuckled. "Yeah, maybe. Thanks for help Allison. Nice to meet you Ray." He smiled walked back towards his table.

Ray's face was crimson with embarrassment. "Oh my God, he was totally flirting with you!"

Allison shrugged. "Maybe a little. It's not a big deal, that kind of thing happens all the time."

Ray dropped his chopsticks. "Wait, really?"

"Sure, pretty women get hit on constantly. I mean, not to toot my own horn, but—"

"No, you're stunning. I guess I just didn't occur to me that you had to fend guys off all the time. It makes me... kinda insecure. It seemed like you were flirting back a little bit?"

Allison gave him a sympathetic look. "You shouldn't worry about it, sweetie, I was just being polite. You know I love you."

Ray beamed and thought to himself how lucky he was to be with Allison. He would do whatever it took to keep her happy.

They finished their meal and shopped a little longer, and Ray got some flashy accessories, like a leather bracelet and a studded belt. Around 2:30, Allison announced that they were done shopping but had one more stop for the day. They got in the car and Ray thought little of it, until Allison pulled the car into the parking lot of Human Canvas.

Ray's heart immediately began thumping in his chest as he started to sweat. Allison could tell he was nervous and tried to calm him down. "Relax, baby, it's going to be okay. This isn't a punishment like last time."

Ray took a few deep breaths and climbed out of the car. Ray was both relieved and embarrassed to see Mark was the only one in the store again.

"Allison! Good to see you again angel!" he boomed, giving her a hug. "And Rob, how's it going?" He shook Ray's hand and nearly crushed it with his massive grip.

"Um, hi Mark, it's Ray," Ray mumbled, glancing down.

Mark shrugged.

"So glad you could squeeze us in," Allison said.

"Of course! Now, we're gauging up that Prince Albert today, correct?"

Ray gulped. Allison nodded.

"Alright then! Ray, get on up in the chair and drop trou."

Ray undid his pants hesitantly and pulled them down to his ankles, then did the same for his briefs. He was embarrassed to expose his caged penis in front of someone, but he told himself that it wasn't anything Mark hadn't seen.

Allison took the key from her ankle and undid the cage. Without asking Ray, Mark immediately began manipulating the barbell and removing it. He spun in his chair and picked up a different barbell from his work table and cleaned it with alcohol.

"Now, this might feel a little tight because it's substantially bigger, but your piercing is healed enough to accommodate it."

He carefully slid the rod through Ray's urethra and out the hole in the bottom. It felt snug and just a little uncomfortable, but not too bad. Mostly he was just flustered about having another man touching his dick, even if it was a professional with gloves. In another few seconds the new jewelry was secured, and Mark looked up at Allison.

"All done! Everything looks great, the tissue is healing perfectly. Anything else for today?"

Allison cocked her head. "Hmmm." She ran her fingers idly through Ray's hair. "I was thinking, baby..."

Ray's heart immediately raced. "Yeah?"

"We could really complete your new rock star look if we got your ears pierced."

Ray froze. He didn't really want to get his ears pierced, and the whole rock star style still made him feel a little self-conscious. On the other hand, it was so much tamer than the piercing he already had, and to tell the truth he really hadn't minded getting that one.

"But," Allison continued, "if you really don't want to you don't have to."

Ray pondered for a couple seconds before making up his mind. It was clear Allison wanted him to, and what was the point of all this if he was going to keep dragging his feet? Besides, it was just a couple of tiny holes, and if he didn't like them he could stop wearing them whenever he wanted. Also, his hair was now so long that it completely covered his ears, so it's not like anyone would notice them if he didn't want them to. He took a deep breath.

"Why not? Let's do it."

Allison squealed with happiness and clapped hands. "Fantastic! You're going to look so good, sweetie."

"Ok then, what kind of studs? Fake diamond?" Mark asked.

Ray shrugged. "Yeah, um..." He looked up at Allison, who was grinning ear to ear.

"Gold studs," she said confidently. Ray nodded in confirmation.

Mark got to work cleaning Ray's earlobes, and then picked up his piercing gun. Ray closed his eyes and winced as he felt a sharp pinch in one ear, and then the other, and then felt them start to burn with a hot but bearable pain.

"All done, boss," Mark said, chuckling.

"Oh, uh, thanks M—" Ray started before realizing that Mark was talking to Allison.

"Thanks so much, Mark, they look great. Here, Ray, take a look."

She handed Ray a hand mirror and he held it in front of his face. Two small gold spheres sat at the bottom of his earlobes, now bright red. He brushed his longish hair back behind his ears to admire them. They did look kind of cool. Maybe when they healed he'd only wear one in his left ear. "Yeah, they look great," he said.

He pulled up his underwear and pants and started to get up from the chair.

"Actually, before you get up..." Allison trailed off.

Ray sat back in the seat. "What? Something wrong? Are they crooked?"

"No, silly. Your ears are fine. I just had an idea, but I'm not sure you'll go for it."

Ray once again got nervous. "What's your idea?"

"Well, we're already here, and—what would you think of a tongue piercing?"

Ray froze for a second. Did he hear her right? "Uhhhh, I don't know about that, babe, that seems like a major decision," he replied, trying to stall for time.

"Is it? It's just another piercing. You've already got three," Allison responded. She seemed so nonchalant about the idea. "And tongue piercings look so edgy. Besides, I've heard that getting head from someone with a tongue piercing feels great. Am I right about that, Mark?"

"Oh, that is absolutely right, trust me," Mark said confidently. He stuck out his tongue to reveal a shiny silver ball in the center and let out a deep belly laugh. Ray sunk into his chair, mortified. "Also," Mark continued, "it'll hurt a little more, but it's one of the fastest healing piercings."

Allison raised her eyebrow expectantly at Ray. He decided to not give himself time to think.

"I'll get the tongue piercing." He exhaled, trying to calm himself.

"There we go! You got yourself a nice obedient boy there," Mark teased him.

Allison was visibly giddy as Mark took a pair of forceps and marked the piercing point on Ray's tongue. After a round of mouthwash and a quick countdown, he pushed a large needle through Ray's tongue, then replaced it with a silver barbell. It was painful, but at this point Ray was pretty used to the feeling. When Mark removed the forceps, Ray moved his tongue around in his mouth. It felt bizarre to have a rigid piece of metal in there, and he wondered if he had done something he would regret.

"I'm so proud of you, Ray. I can tell you're really trying to keep an open mind." Allison leaned down and kissed him, which made Ray instantly feel better.

"Yeah, what's the point of life without a little adventure?" Ray said, lisping as he tried to acclimate to speaking with his new accessory.

They walked out of the shop and were almost in the car when Allison turned around.

"Oops, be right back! Forgot something."

She went back into the store. Ray watched through the window as she spoke to Mark for a few minutes. He couldn't hear what they were saying, but it was clear they were laughing about something. Ray began to feel embarrassed again and wondered if they were talking about him. Finally Allison patted Mark's arm and waved goodbye. She had a broad smile on her face as she exited the shop.

"What were you talking about?" Ray asked cautiously.

"I forgot to get the care instructions for your new piercings!"

"That's all? You were in there a while."

Allison wrinkled her nose. "Jeez, relax honey! I was just thanking Mark for being so flexible. Piercing artists don't just typically let their clients do things on a whim, you know. He really did us a favor."

Ray shrugged and touched the new tiny gold globes sitting in his earlobes. "Yeah, I guess he did."

**********

The new piercings were fairly easy to care for, and after a couple days of the tongue piercing feeling weird Ray quickly learned how to eat and talk with it. A few months ago he would never have even considered the idea of getting a piercing, and it was still shocking to him how comfortable he was having multiple ones.

Throughout his life, Ray had always taken a perverse pride in not caring much about his appearance or how he dressed. He had always told himself that people who spent time shopping and primping were vain and shallow, but with Allison's program of self-improvement he had come to realize that that attitude was just an excuse for his own laziness. He was now taking pleasure in looking at himself in the mirror in the morning and picking out his outfits every day. It felt good to wear fashionable clothes that fit his athletic body. He even found himself shopping for new clothes in his spare time online, something he had always viewed as a waste of time.

He was also sleeping better and feeling healthier than he ever had. At first he had done yoga just to placate Allison, but now that he could feel himself getting more flexible he looked forward to it and enjoyed the sensation of deep stretching it gave him.

And yet, despite all this, Ray was beginning to feel a little frustrated. All of these changes had started as a way to fix their sex life, and months later Ray still wasn't sure when they were going to try having sex again. Not that he felt dissatisfied, exactly—while he still found it a little bit humiliating for Allison to use a dildo on him, he had to admit that the orgasms he had from anal were more intense than anything he'd ever felt from his dick. And Allison certainly seemed to be enjoying herself more. Still, he wondered when he'd finally get to fuck Allison again like he wanted to.