Remaking a Boyfriend Pt. 03: Learning New Tricks

In contrast to the head-spinning events of the previous week, the next couple weeks were relatively uneventful for Ray. He had less trouble keeping his mind off of sex while his new piercing healed than he had been expecting. Both he and Allison were busy with work, and what time they had together they spent watching TV and talking. Ray continued running and doing yoga at Allison's request, and found himself sleeping better and feeling increasingly happier and healthier. They settled into a comfortable routine where Ray would run early in the morning, have a smoothie Allison made him, work until lunch, eat, work a few more hours, then do yoga and make dinner for the both of them. For a while all of these new things felt like burdensome chores to Ray, but it wasn't long before he began to appreciate the positive effects on his mood and confidence. He felt more energetic and sharper than he could ever remember.

One morning Allison caught him examining himself in the mirror.

"Admiring yourself?" she asked jokingly.

Ray laughed, but it was kind of true. He had lost almost 10 pounds since all this started, and he could already see visible effects. He looked more toned and less chubby.

"Now I just need to start hitting the weights and get ripped," Ray said.

Allison wrinkled her nose. "I don't want to you to change what's working, honey. Just stick with the running and yoga. Weightlifting might make you start gaining weight again. Plus, you're not really the musclebound meathead type, and I like that about you."

Ray shrugged. "Sure, whatever, you say." He looked at himself in the mirror again. "Sheesh, I need a haircut, though." Ray usually kept his hair short, but it had been a few months since his last haircut and his blonde hair was long enough now that it was starting to get in his eyes and get slightly curly around the edges.

"Absolutely not!" Allison said. "You look great with long hair. Promise me you won't cut it without consulting me."

"Okay. Of course, babe," Ray said, a little puzzled.

"One thing we do need to do is get you some new clothes, though! I'm taking you shopping on Saturday."

"I won't object to that," Ray said cheerily.

That Saturday, Allison took Ray to the local mall. They walked through stores for hours while Allison picked out clothes for Ray to try on. Ray normally hated shopping, but this was different. Allison was showing interest in him, and the thought of looking good for her excited him. His current wardrobe wasn't exactly fashionable, skewing mostly toward comfortable baggy clothes. At the mall, though, Allison had him trying on much more tailored, form-fitting clothes, like skinny jeans and slim-fit shirts. One of the pairs of pants he tried on was so tight that he could barely pull the bottoms of them over his ankles! They turned out to be Allison's favorite pair, naturally. She also bought him a few new pairs of fashionable, minimal sneakers to replace the tennis shoes he wore every day.

At the end of the day, Allison told him they had one last store to visit. Ray was relieved, as he still found shopping a little tiring, but he was a little surprised when Allison guided him into Victoria's Secret.

"You've been so cooperative today, I'm going to give you a treat," Allison said. "You get to pick out the sexiest thing you can find here, and I'll save it for a special occasion." She smiled devilishly.

Ray's eyes lit up and his cock twitched. He immediately began looking around the store, imagining Allison's perfect, athletic body in all of the skimpy lingerie that surrounded him. He examined all sorts of different bras and panties, growing increasingly aroused as he imagined Allison modeling all of them. Finally, his eye was drawn to a full lingerie set that was displayed on a mannequin. Everything was black patterned lace, and it consisted of full stockings, a garter belt, a thong, and a bra that barely covered anything. The tops of the stockings were decorated with small red bows.

Ray turned to Allison and pointed at the mannequin. "That."

Allison giggled at his eagerness. "Excellent choice, Ray. Maybe with some high heels?"

Ray nodded vigorously.

"I thought so. Let me just pick out the right sizes and we can go."

"Don't I get a sneak peek in the dressing room?" Ray asked mischievously.

Allison grinned at him. "Good things come to those who wait."

They drove home, but Ray couldn't stop thinking about Allison in the lingerie he had picked out. The whole night he kept putting his arm on her and rubbing her shoulders. He persisted until Allison had to tell him to stop.

"I know you're feeling romantic right now, Ray," she said, "but your piercing is still healing. We can't have sex even if I wanted to."

Ray hung his head. It was the truth. He tried to distract himself with a reality show while Allison read on the couch, but he couldn't get his mind off of sex. Allison was right, though, they couldn't have any kind of sex for another few weeks while his piercing healed. Except...

Ray put his hand on Allison's leg and looked at her sheepishly. "Hey babe, I was, um, thinking that..."

Allison put down her book and looked at him.

Ray continued. "I was thinking that, even though we can't have, you know, normal sex, maybe we could do, uh, what we did a couple weeks ago?"

Allison cocked her eyebrow. "What exactly are you asking, Ray?"

"Um, to do the stuff we did with the uh..." his voice dropped to a whisper. "...dildo?"

"Ray, there's no way we're doing something if you can't even say what it is. Tell me what you want me to do."

"I want you to have sex with me, with the dildo?" Ray said, unsure.

Allison shook her head. "I'm not sure what that means. You have to be more specific." It was clear she knew what he was talking about, but wanted to make him squirm a little.

Ray swallowed. "I... I want you to fuck my ass with a strap-on."

Allison's face broke into a wide smile. "Oh, that," she said playfully. "Are you sure want that?"

"Yes."

"Yes, what?"

"Yes, I want you to fuck my ass with a strap-on," Ray said more confidently.

"Which strap-on, though? I need more details."

"Your strap-on?"

"Hmmm," Allison said, clearly enjoying this, "that's not what I call it."

Ray took a deep breath. "I want you to fuck my ass with your cock."

Allison bit her lip and thought for a few seconds as Ray waited anxiously for her answer. "How about this," she said finally. "I'll fuck your ass with my cock next weekend, but only if you do some homework."

Ray nodded eagerly.

"I want you to spend the next week finding porn where the guy does a particularly good job of fucking the girl, where he's really getting her off. I want you focus on what he's doing and how he's bringing pleasure to the woman he's with. I think it will be really good for you, and help you understand what it means to please your partner. Are you ok with that?"

Ray thought for a brief second. So she wanted him to watch porn? That wasn't homework at all! "Yeah, I'm totally ok with that," he replied confidently.

Allison nodded. "Also, I want you to wear the chastity cage again, so that you're not tempted to masturbate while you watch porn."

Ray nodded in acquiescence. It shouldn't be a problem given that his piercing wasn't healed yet.

Allison went to the bedroom and got his chastity cage. She made Ray pull down his pants, but hesitated before she put the cage on.

"Hmm, actually, I'm a little worried about you being able to keep your pubic hair out of the piercing while you're in the cage," Allison explained.

"Oh, yeah, good point. I promise I won't masturbate if you leave the cage off, I don't want anything to get infected."

Allison shook her head. "No, sweetie, that's not what I meant. I think we need to shave you."

Ray shrugged. "Okay, I can use my clippers to get it really short. It shouldn't be a problem then."

"Ray, I know how to take care of body hair. I'm a woman, remember? Let me just shave it. And besides, I bet the cage will feel more comfortable without all that itchy hair in the way."

"Uh, yeah, I guess that sounds okay."

"Okay, great!"

Allison led him into the bathroom. She started by using Ray's pair of clippers to trim his unkempt pubic hair to a reasonable length all around his groin and even under the bottom of his balls. She then had him stand in the shower, and spread some of her shaving gel on his pubic area. She took her pink razor and carefully began to trace over the shaving gel, periodically rinsing the razor under the faucet. Ray was nervous about her running a blade over his most sensitive areas, but Allison seemed confident and before long she had shaved the entire area clean.

When she was done, Ray ran his hand over his crotch and was surprised at the unfamiliar yet pleasant sensation of his smooth, completely hairless skin. His cock looked foreign and smaller without the thatch of pubic hair surrounding it, but it also looked cleaner and nice in a way that he couldn't quite put his finger on. He started to step out of the shower, but Allison stopped him.

"Not so fast, we're not done yet," she said. "Turn around."

Ray knew better than to ask questions at this point and did as he was told.

"Bend forward and spread your cheeks for me."

Ray understood that she wanted to shave his asshole again. He leaned forward against the shower wall and spread his ass cheeks apart with both hands. It tingled as Allison lathered shaving gel into his ass crack and slowly began drawing the razor over his skin. Ray tried his best to stay still, but the proximity of Allison's hand to his asshole was giving him memories of their most recent encounter and causing his cock to twitch. After a few minutes, Allison announced that he was done, and Ray stepped under the shower head to rinse off. It was a strange, intense sensation to feel the water running over his bare skin, and it left Ray feeling a little aroused. After lingering in the shower, he dried off and stepped out into the bedroom where Allison was waiting for him.

"Shaving can iritate your skin the first few times, so I'm going to put some lotion on it, okay?"

Ray nodded. Allison grabbed a purple bottle of floral scented lotion from her nightstand and poured a dollop into her hands. She applied it to Ray's penis and testicles, moving her hands slowly over all the skin she had saved, including his ass. Her soft but firm touch, combined with the silky lotion over his smooth skin, was heavenly, and Ray's cock quickly stood at attention.

Allison finished, and waited patiently until his erection began to deflate. She then retrieved the chastity cage and put both pieces on. They slid easily over his lubricated skin. Ray had to admit, it did feel more comfortable without his pubic hair getting caught anywhere. Allison closed the lock, and put the thin chain with the key back around her ankle.

Ray was fantastically turned on, but he was also determined to please Allison by sticking to the plan they had agreed on. As tough as it was, he tried to take his mind off of sex and spent the rest of the night playing video games to distract himself. His sleep that night was restless, as his thoughts kept drifting to Allison and her lithe naked body.

The next day was a normal Monday, until noon when Allison sent him an email reminding him that he was supposed to find examples of porn. Ray, satisfied with the work he had done for the day, took the afternoon off and browsed his favorite porn sites. He skimmed all kinds of different videos: gangbangs, softcore scenes, BDSM. Finally he clicked on a video that made him lean forward in his chair.

It was a well-shot scene between an adorable young girl and an older guy. After some kissing and undressing, the guy started fucking the girl doggy style. The whole time his mouth was right next to the girl's ear, whispering filthy things to her. Unlike most porn where the girl is clearly performing for the camera, in this scene the girl seemed to be genuinely lost in pleasure as the man pounded her increasingly hard. Her eyes rolled back into her head as he placed a hand at her throat, while still snarling into her ear about what a filthy slut she was, and how he owned her pussy. He slapped her ass hard a few times with his other hand, causing her whole body to quiver. Within seconds, she was in the throes of an intense orgasm, writhing in pleasure and gasping for breath. As she finished bucking, the man released her, letting her slump down onto the bed. He pulled out finished himself with his hand, spraying his massive load onto her ass and back. As the camera pulled out and the scene ended the girl's face was so blissfully calm that she almost looked asleep.

Ray's cock was straining at its cage for the entirety of the video, and by the end it was so swollen that he had to get some ice cubes from the fridge and put them on his balls to make his erection retreat. He was incredibly horny, but there was nothing he could do for relief. And besides, he wanted to follow the rules so as not to miss out on the reward Allison had promised him. He bookmarked the video and set about preparing dinner.

That night and the rest of the week were pretty uneventful, other than Ray's midday searches for porn. He actually found it interesting to pay more attention to what the man was doing in the porn scene, like it was a new and exciting way of experiencing a favorite pastime. He also realized that very few scenes really focused on the girl's pleasure-most involved the girl enthusiastically fucking until the guy came. Over the course of the week, he found two more clips that really stood out to him.

One was a scene where a guy was making a girl squirt. He did so by putting his index and ring fingers inside her and moving his hand up and down. He would do this for maybe fifteen seconds, then pull his fingers out as the woman squirted violently and contorted in a way that looked almost like an exorcism. After a short rest, he would do it again. He repeated this maybe ten times before the woman had to crawl away from him because it was too intense.

The other was a very vanilla scene with nothing outwardly noteworthy, other than that the guy was unusually handsome and muscular, even by porn standards. It was a missionary sex scene, but it was clear that the girl was especially into it. They kissed passionately throughout the sex, but despite their intensity the guy kept the pace of the sex very slow. He would pull his sizable dick nearly all the way out of her pussy, then hold it there, his tip just barely parting her lips, then plunge in all the way, grinding his pelvis into hers. Ray could tell that this control took crazy abdominal strength, as the guy's abs were bulging with exertion. He kept up this slow, even pace, until the girl arrived at a long, intense orgasm. When he pulled out, semen gushed from the woman's vagina, indicating that they had cum simultaneously.

On Friday Allison asked him to send in his homework, and Ray sent her the videos he had bookmarked. He spent the rest of the day anxiously looking at the clock, waiting till Allison got home. When she finally returned, Ray immediately started waiting on her hand and foot. He took her briefcase from her, helped her out of her work clothes and into some comfortable sweats, and poured her a glass of wine. Allison was affectionate with him, but didn't mention anything about the videos. Ray didn't want to bring it up for fear of annoying her, but he was beside himself with anticipation. Instead he asked her about her day, and she recounted an annoying meeting she'd had with a client. Afterwards, they sprawled on the couch and watched TV while Ray gave Allison a foot massage. Finally, after a couple hours, Allison turned to him.

"So Ray, I looked at your homework you sent me, and I wanted to tell you that you did a really good job," she said evenly.

"Really?" he asked excitedly.

"Yes, those videos were extremely hot. I watched them on my phone at work and had to take a, uh, bathroom break afterwards."

Ray's heart sped up and his dick began to stir inside its cage as he imagined Allison, in her conservative but still stunning work attire, fingering herself in the bathroom.

Allison could tell that Ray was aroused, and giggled. She extended her leg and moved her foot up Ray's thigh and onto his crotch. She flexed her red-lacquered toes and squeezed his chastity cage through his shorts. Ray's mouth went dry, and his cock began to pulse against the metal constraint.

"Be honest," Allison said, "how horny are you right now? Scale of one to ten?"

Ray swallowed. "Eleven. I seriously don't know if I've ever been this horny before."

A devilish smile appeared on Allison's face. "It makes me so hot to hear that, baby. But you're being so good and so patient, and I want you to know that I appreciate that. Tell you what, tomorrow, after you go for a run I'm going to have you go shopping, and then when you get back we'll have some fun. Sound good?"

"Absolutely!" Ray said a little too loudly.

They went to bed shortly after that, though it took Ray over an hour to calm down enough to fall asleep.

The next morning Ray woke up with a feeling he hadn't had since Christmas morning as a child. He jumped out of bed and practically ran out to the kitchen, where Allison had already prepared a special breakfast of whole wheat pancakes and his daily smoothie. She watched with amusement as he wolfed his meal down. After he was finished he went for a three mile run, which according to his fitness tracker was his personal best time. When he got back he took a long shower, enjoying the feeling of his own hands on his body. Even though he couldn't stimulate his penis through the cage, he was so aroused that his entire body felt like an erotic organ. When he was finally finished and dressed, Allison told him to go to the drugstore to pick some things up and gave him a shopping list.

Ray grabbed the list and hopped in the car, eager to get the errand over with as soon as possible and already thinking about what awaited him when he returned. It wasn't until he got to the drugstore that he actually looked at the list. It read: condoms, lube, enema, latex gloves, red lipstick. Ray's heart started pounding and he began sweating as he looked over the list. He had to buy all those things? He was going to look like such a pervert! What would the cashier think? What if he saw someone he knew in the store? And what were they all for?

His next thought was that if he didn't do it, Allison would be mad at him and wouldn't touch him. He scoped out the "intimate items" aisle that had most of what he was looking for. He walked by a few times, waiting for a moment when the aisle was empty. Finally he saw his chance, and quickly grabbed a pack of condoms and a bottle of KY Jelly. He grabbed an enema from the nearby laxative section, then hurriedly made his way to the medical aisle, where he frantically looked for latex gloves. He realized that he should have gotten the condoms and enema last. Finally he found the latex gloves, and made his way to the checkout. There was no line, but Ray's ears began to burn when he saw the cashier. It was a young cute girl, probably a student at the local college. She had long bottle-blonde hair tied back in a messy ponytail, and multiple piercings in both ears. Ray glued his eyes to the ground and went to counter, dropping his items in front of him.

Shit, he thought suddenly, the lipstick. He glanced up at the cashier, who had a look of curiosity in her face. "Um, one second," Ray stammered, "I forgot something."

The cashier gave him a look like she was about to laugh, but just said, "No problem, sir."

Ray raced to the makeup aisle and grabbed the first tube of red lipstick he could find. When he returned to the register, he saw that a large man in his thirties was now checking out, and was eyeing Ray's items with suspicion. As Ray stood behind him, he turned around and looked directly at Ray, giving him a look of disgust that made Ray want to crawl under a blanket and hide. His ears were on fire, his heart was galloping, and he just wanted to get out of the store. Finally, the man in front of him finished, and Ray handed the cashier the lipstick. She rang up his items wordlessly, but with a small smirk on her face. As she handed Ray the receipt and his bag, she looked him right in the eye.