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."