Once he woke up Catherine on his sofa, she forced him to put on some more creams and suchon his hands and face. He swore, this woman was going to turn him into a damned lotion bottle. After that, she forced him to go shopping with her, choosing things that would specifically fit him like a glove. She refused to divulge exactly what she was planning on making him wear, but trying on these clothes was about to give him an aneurism. While looking around the store, they could be perceived as a normal pair looking for her. Once they got up to the changing rooms… well, Craig was glad that he didn't go to shopping malls often. He'd probably never return after a few strange looks by the employees.
She didn't let him see what she was buying for him, though she'd hold up an array of different colors of fabric against his chest to see what would suit him. She also eyed him suspiciously a few times while traipsing through a row of accessories.
The lingerie store was possibly the most mortifying. Thankfully, Catherine only needed a few measurements to know what she needed instead of making him try on an assortment of silky and frilly things. Craig's stomach hurt; this was the worst few hours of his life, he thought. That is, until he realized he still had a 'date' tonight. After a quick trip through a department store makeup aisle, Catherine finally had mercy on him and they went back to his apartment. Fact: Shopping was a time-consuming and mostly pointless errand. She managed to keep him out until six in the evening, he realized with a groan.
She banished him to the shower again. Once he was clean again and smelling like peaches, he found that she had laid out a couple of articles of clothing for him. He pinched the bridge of his nose to try to relieve the ensuing headache. It didn't help. He sat down next to a pair of opaque black stockings with a leaf pattern around the thigh, a light pink and black lace garter belt, and a matching panty and corset set in the same light pink and black lace. Oh Christ, what in the world was Catherine up to? She clearly wasn't doing this halfway.
He picked up the pair of panties and seriously thought about throwing them out of his bedroom window, but going commando on a date with someone like Rick sounded like an all-around bad idea. Fact: He intended on getting through this as quickly and painlessly as possible. The lace was delicate and he knew that if he tried to pull them on like a pair of boxer briefs, he'd probably rip them. She was intentionally trying to make this difficult for him… He dried himself off and pulled them on slowly, trying not to break them and suffer an emergency trip back to the shopping mall. The lace surprisingly didn't scratch and itch like he thought it would. It felt… kind of strange, as it wasn't unpleasant at all.
The only other thing he even had the inkling how to put on were the stockings and even then, he was afraid he would put a run in them. He gathered them up to the toe and really hoped that nothing went wrong. He slowly pulled them up his calf and stopped at the knee with a shiver. Fact: He evidently had sensitive legs. They were made out of a fine silk and they swept over his now-hairless legs like someone breathing just over his skin. Suddenly the lace panties he'd put on felt a little uncomfortable. He ignored the feeling and pulled on the other stocking. Now it was worse. He'd have to even this whole situation out when this was done. Yeah, Catherine helped him out, but she was making it worse, as well. He wasn't sure which was the deed that would get its reward.
Speak of the devil, Catherine waltzed into his bedroom like it was here, "Are you done yet? Do you need some help? Why am I asking? I know you do."
She picked up the garter belt and unhooked the back, "Could you stand up, please?"
Craig's face pinked when she arrived, but he did as he was told. She hooked the garter belt around his waist and attached the stockings to the buckles. Craig did his best to not flinch when she moved the stockings. It felt so strange… He couldn't decide if it bothered him or it felt very good… No, he wasn't supposed to enjoy this, it must bother him, he decided.
"Okay, are you ready for the corset now?" Catherine asked when she finished adjusting the garter belt.
"Cat, I'm not so sure about that…," Craig said, trying to protest.
"Go big or go home, right?" Catherine said, unhooking the hooks on the front.
She had a point, he supposed. Not a point he really liked, but a point, regardless. She waved at him to raise his arms and he complied. She snapped the pink corset around his waist; it was a bit more comfortable than Craig would have imagined, being some silky fabric on the inside. It covered just under his navel and just over his nipples, he realized, aiding the illusion that he was just a very flat chested woman. Then, Catherine moved to the laces on the back.
"Ready? Can you take a deep breath and breathe out for me?" she said, pulling at the unkempt bow it was packaged with.
Craig swore under his breath something colorful about bad karma and cruel gods, but he did as he was told. When he breathed out, Cat pulled as hard as she could on the laces, paying special attention to the waist. When she was done, Craig felt his spine straighten into place and he found it kind of difficult to take a deep breath.
"Okay, want a robe? It's time for hair and makeup!" she said cheerily.
Craig took his bathrobe from his closet without answering her. He was having a hard time summoning the breath to speak in the first place. He hoped he didn't pass out. She led him to a stool she set up in the middle of his living room and sat him down before immediately opening up several of her makeup trunks. She pulled out brushes and sponges all over the place.
"Craig, I'm so jealous, you have such good skin," she said absently, sponging on a very light colored foundation.
He ignored her silly banter and tried to focus on breathing. She tied this thing deceptively tight, apparently. He hadn't seen himself in the mirror yet, nor had the desire to, but he had to imagine it created the silhouette she was going for. She brushed, rubbed and dabbed until she was done, standing back several times to make sure she got the look she was going for. She finally looked satisfied and moved over to the coffee table full of wigs. He winced visibly when she touched some of the stranger looking ones. She mercifully passed over a 50's style bouffant and the ridiculous beehive style. She picked up two particularly light blonde wigs and put them near Craig's head to compare. He couldn't really tell what kind of style they were, much to his chagrin. She seemed satisfied and walked away to pick up another bag.
"It's almost seven thirty! When did it get so late?" she mused to herself, "We have to get you fully dressed still!"
She was right; he was sitting in his living room in unmentionables rather uncomfortably. She pulled out a bright blue dress from the bag, Craig suddenly remembered trying it on. It was short, he remembered ruefully; it had a wrap detail and a slight 'v' neckline. She started to pull it over his head, commanding him to stand in the only way she knew how: asking rhetorically. She quickly zipped the back and stood back to admire her genius.
"Ahh, you want to see how good it looks on you?" she spouted happily, "You look great, you know?"
Craig grimaced. He didn't really care, just so long as no one found out who he was. That would be a horrifying experience and he'd probably have to leave the library and then the entire town. Catherine buzzed around him, trying to make some adjustments.
"Did you know you have such boney shoulders?" she asked with some despair, adjusting the fabric one way or another, "Nothing I can do now, but I accounted for everything else!"
She pulled out another bag and then a shoebox. Oh god, he forgot about trying on shoes. He didn't even want to think about what he'd tried on. She was convinced he needed something sky high to make up for being so short for a guy and then laughed as he tottered around the shoe store. She pulled out a pair of booties, she had called them. At least he wouldn't fall out of them, he thought, they had a zipper up the side. She had him sit again and put them on for him. They slipped on much easier with the stockings, and they weren't as uncomfortable as he remembered.
"Ah, did I forget anything?" she asked, tapping her chin, "Oh, how could I forget?"
She dug in the plastic bag again and pulled out a chocker with a rhinestone bird on the front. She quickly put it around Craig's neck to cover his Adam's apple and tightened it slightly so it wouldn't slip down during the night. She then slipped on of the wigs over his head and stared to pin it into place with a mass of bobby pins. Pin after pin and wince after wince got the wig in place.
"There! Ahhhh, you can't even see yourself, can you?" Cat gushed, "Let me see your hands."
Craig didn't respond. Of course he couldn't see himself, that silly twit. He did lift his hands so she could see them and she tutted at him like a mother hen.
"Your hands are too boney! Why are you so skinny, Craig?" she pondered, while digging into her bag again.
She produced a pair of delicate black gloves which she promptly put on his hands without asking. He glanced at them; they were soft at least and not uncomfortable. Aside from the restricting corset, nothing in this outfit was very bad… Not even the very tall heels he was wearing, not so much.
"Do you want to see now?" Catherine asked with a beaming smile.
"I suppose so," Craig said with a bit of trepidation.
Catherine picked up one of the big stylist mirrors she had and held it up for him to see. He did a double take and not in a particularly good way. He stared for a moment, turning his head so he could see it was actually him. The wig was long and layered; it surprisingly suited his now-very feminine looking face. The blue of the dress made his eyes look a darker pink, surprisingly. His thin mouth was lined with a soft color that actually made him look decidedly feminine. If he had to judge, he wasn't the most feminine and beautiful creature, but he definitely looked like a woman.
He looked down at the dress, which thankfully covered his boney shoulders with some adjustment from Cat. She was beaming at him the entire time, like she was a proud mother or something similarly disgusting. Fact: Craig was beginning to feel like a reluctant teen going to prom. Reliving his high school days was really not making him much happier. Catherine began to put some objects that Craig wasn't paying any attention to in a peacock blue evening bag.
"I have some supplies for you, just simple things," she said with an excited smile, "A little bit of makeup remover for when you're done with your little date, some of the lip stain I put on you just in case, and then your phone, which I turned off, and your ID! Is that everything?"
"I'm sure that's more than enough, Catherine," Craig said, taking the bag from her before she could stuff anything else into it.
"Oh no! Where did the time go? It's almost eight!" Catherine said, "Gogogogo, get into your room, I'll tell you when he gets here, okay?"
"What? That's very unnecessary—"
"GO," Catherine commanded.
Craig shut his eyes in a vain attempt to make Catherine and this whole situation go away. It didn't appear to be going anyplace, but regardless, he went back to his room, trying to remember if he had an aspirin left. He was having a little bit of a hard time walking in these damned heels, but he made it and shut the door behind him. He hobbled to his bed and sat down. He didn't really want to be alone with his thoughts, but here he was, sitting in a blue dress with a pair of stockings and heels. Things couldn't get much worse, but then Craig remembered that Rick had still yet to appear.
Craig stiffened; he could hear voices. In particular, a high-pitched questioning voice and a gravelly accented voice which could only belong to one person. He couldn't hear what they were saying, unfortunately. He could only imagine that Catherine was further humiliating him. He stood up too fast when there was a knock on his door, but he managed to stay on his feet. Catherine didn't wait any longer and opened the door.
"Hey, didja hear the door or not?" she asked, not waiting for the answer, "He's here, you know!"
Craig mumbled something about impractical shoes and how he was going to kill the inventor of corsets, which Catherine took for an affirmative of some kind. She opened up the door so he could come through, even at his slow pace. Rick was sitting there on the couch, wearing a dark blazer and slacks, complete with a jade green button up. Even Craig in his near-catatonic humiliated state had to admit that the lout cleaned up well. Rick finally looked up from the assortment of wigs on Catherine's table to hold back a laugh. Craig frowned; his mind nearly went 'I don't look that bad, do I?' He quashed that thought down quick.
"Hey there, gorgeous," he said, standing up from the couch to come over, "I was hopin' t'take out your brother, not a pretty thing like you."
Craig nearly ground his teeth; Rick's tone was obvious and he was joking around, "I swear to god, can we please just get this over with?"
"Now, Pinkie, don't tell me this is somethin' you do often, that'd ruin this whole bit I cooked up," Rick said taking Craig's gloved hand to get a better look at him.
"Nope! Craig didn't mention anything about me, did he?" Catherine said, picking about the worst time (read: always) to interrupt, "He didn't tell you about his best friend? I'm a makeup artist for the local theatre group! Did you know that I was trying to get him to do this for years?"
Craig shut his eyes and ran through the titles of all of Shakespeare's comedic plays to try to block out their conversation. He was trying desperately to go to his happy place. Rick was flirting with Catherine pretty obviously, too, from the snippets that Craig caught. Now he was trying harder for his happy place.
"Is that so, sweetheart?" Rick said, "Well, if this's your work, then damn, you deserve a medal."
Cymbeline; The Taming of the Shrew.
"Oooh, you're very nice, did you know that? I don't know why you like Craig then, isn't he grumpy?" Cat prattled, "Don't you think he's got the hips for it? I mean, do you know how easy it was to put him in a corset?"
The Merry Wives of Windsor; Troilus and Cressida.
"Corset?" Rick asked with raised eyebrows, "Why, no, I dunno how easy that was. You must be strong, sweetheart."
As You Like It; The Merchant of Venice.
"Aw, you think I'm strong? I'm most proud of his face! Isn't it boney...? Isn't he kinda boney all around?" Catherine quipped.
Twelfth Night; The Tempest.
"Well, I think we should maybe get goin', we got 'pointments to keep'n all," Rick said, curiously not taking the chance to poke some more fun at Craig's expense.
"Oh of course!" Catherine said, "I need to get home anyway, have fun, Craig!"
All's Well That Ends—Oh shit.
Craig had to pay attention again once he realized that Catherine was packing up her stuff and about to leave him alone with this perverted blowhard. He warily looked up at Rick, who was giving him something akin to a carnivorous grin that Craig didn't like the looks of. His ham-hands still had Craig's in a bind, like he knew Craig would bolt if given the chance.
"A bet's a bet, darlin' and you sure have delivered," he muttered to him so Catherine couldn't hear.
"Thanks, sweetheart for takin' care of this little lady, but I have a reservation to catch," he said, pulling Craig out of his apartment before he could argue.
Catherine looked like there was another question on her lips, but it was lost in the slam of Craig's apartment door. Rick quickly pulled Craig close so Craig had to put his hands on Rick's shoulders. Rick's expression was one of competition and amusement, whereas Craig's was half-mortification and half-red embarassed blushing.
"Look here, beautiful," Rick said in a low voice, "I'm a gentleman so I'm gonna give you somethin' of a heads up. We're goin' to dinner and then a little club I know of, yeah? Here's yer'catch, durin' dinner, you can't speak unless it's t'me. I'll order fer'you, don't worry. At the club, y'gotta dance with whoever takes a likin' to ya, understand?"
Craig didn't have any other choice but to nod quickly. Anything to make him let go, Craig figured, anything to stop his head from spinning right now. God damn all attractive men, was the thought that ran through his head for exactly forty seconds straight. Fact: Infatuation and attraction were indicators that the object of said infatuation and attraction would be ideal for mating. Therefore, these were completely useless characteristics to a gay man; but the body had a different idea.
Thankfully, Rick seemed to be done with his 'amusing little rules' and had Craig's hand firmly still in his grasp while nearly dragging him down the stairs toward the parking lot. Craig was looking around for the beaten up pickup that Rick had used to drag him around that day to prove him wrong, but he didn't see that red eyesore anywhere. Rick was dragging him right toward a sleek and shiny black Dodge Charger while digging in his pockets for keys.
"Wait, what happened to your truck?" Craig said as he helplessly clomped over to this much, much nicer car.
"Hey, can't drive a lady 'round in a nasty old thing like that, kin'I?" Rick said with a flashy grin.
Craig didn't reply, but was instead calculating the possible wages of a delivery truck driver and then comparing it to an estimated cost of the car. They didn't match up, not even close; this model was very likely from the past five years and that made the value of a car jump significantly. This level of surprise was leading Craig to believe that he wasn't getting a clear picture of Rick the UPS delivery man and frankly, that kind of spooked him.
Rick was messing with his keys for a moment and then opened the door with a grand gesture, finally letting go of Craig's wrist. If only he weren't wearing a pair of ridiculous heels, he might've tried to bolt, but instead he found himself sliding somewhat gracefully into the passenger seat. With one shut door and a revved engine later, Rick was speeding down the road. He surprisingly didn't have his radio blasting this time and now the trip was much, much quieter. The silence was near deafening until Rick finally broke it.
"Y'look like a deer in'th headlights, sweetheart," he said with a quick glance, "What's on'yer mind?"
Craig scowled and sarcastically thought of all the reasons he might be feeling like a fish out of water. Oh, I don't know, I'm wearing a wig, a dress, and a pair of heels, not to mention a set of lace undergarments and the steel-boned equivalent of HELL while being whisked off by some slightly mysterious albeit overly attractive meat head with a fetish for cross dressing and so many black belts that he could probably murder me with one misplaced gesticulation! With that rather lengthy run-on thought, Craig realized he had been silent for several seconds and Rick was occasionally glancing over to him expectantly every so often.
"Forgive me if this is particularly crass and unusual for me," Craig finally muttered.
Rick laughed, "Never fear, gorgeous, next time y'kin wear whatcha want."
Craig tried to take a deep breath so he could yell, but it was quickly cut off by lack of air. Fact: Whoever invented these things should be permanently strapped into one. He opted instead for pressing his hand on his stomach to try to ward of an oncoming cramp and speaking in a much more mild tone.
"Who ever said there was to be a next time?" Craig said in a near wheeze.
"Eh, I'll letcha decide when this whole mess's over," Rick amended.
Craig didn't have time to roll his eyes; Rick made a sharp turn and they arrived someplace Craig didn't recognize. It had a stucco exterior and a lot of lights on the outside; it looked crowded and that made Craig's shoulders droop. He didn't get out often, so it really didn't mean anything that he didn't recognize the place. It gave him a little hope that he wouldn't run into anyone he might possibly know from his very small social circle. Rick pulled up to the front and a valet opened the door on Craig's side. He froze for a moment, surprised enough that he didn't think of what to do immediately.
"Uhm, ma'am?" the valet said slightly nervous.
Rick was lightning fast putting the car in park and zooming over to the passenger seat to help Craig out of the car, or at least, that's how it seemed to Craig who was approaching dangerously high overheat levels. His face was flushed, but he managed to get out of the car with Rick's assistance. He found his hands desperately clinging to Rick's elbow as he navigated the sidewalk for the wobbling blonde.
Craig vaguely registered a long line of people and Rick coming up to a podium and saying his last name. He was panicking so bad in his head that he was going to trip, or his wig was going to fall off, or something else similarly mortifying that he wasn't paying attention to much else. He finally woke up when he was sitting in a booth a little too close to his date.
"That wasn't so bad, was it?" Rick said, not minding at all that Craig had a death grip on his arm.
"Easy for you to say," Craig growled, letting go of Rick's arm.
For some reason, he felt much more vulnerable without the contact, but he would simply have to deal with it. A waiter eventually found their way to them and Rick, true to his word, ordered everything in a jaw-dropping fluent French. Craig didn't speak French and Rick spoke so quickly that he couldn't catch anything he said. His jaw was hanging open for several more seconds after the waiter left and Rick finally looked over at him and grinned.
Rick reached over and tapped underneath of Craig's jaw, making it snap back up in a hurry, "What's that look for, huh?" he said, looking positively smug.
"…How did… I don't…," Craig babbled.
"Same reaction with the car, I'see," Rick said sounding like he might laugh at any moment, "Lessee, we gonna play the guessin' game or are you gonna tell me what's up?
"I-I didn't know you spoke French," Craig finally stammered, but now that he thought about it, Rick had mentioned being in Europe a whole lot while trying to flirt with his coworkers.
Rick didn't mention it, thankfully for Craig, "And th'car?"
"You drove a beat up pickup truck last time…," he trailed off, thinking back to the calculations he made about the salary of a UPS truck driver.
"Can't have 'nother car then?"
"The salary required to ob—"
"Now you're jus' assumin' when you don't know," Rick said, wrapping his arm around a reluctant Craig's shoulders, "Though, t'be fair, I did th'same to you."
Craig involuntarily relaxed a little out of curiosity. He wasn't terribly surprised, but Rick made it sound like he would explain, at least. Everyone else just passed judgment and moved on; much like he himself did. It was easier that way, unless people like Catherine and now Rick were forcing their way into the line of sight for further examination.
Craig tensed up again, ready for the onslaught of insults to come, "Then what did you assume?"
Rick looked thoughtful for a second before he answered. Wine came to the table and the waiter poured two neat champagne glasses that Rick quickly picked up and offered to Craig. He absently took it, half forgetting he was wearing gloves and nearly dropping it on his dress, but he was much more interested in what Rick had to say. After all, who doesn't like to be talked about?
Rick carefully took the champagne glass before he spoke, "At first, y'looked like someone who'd have a fam'ly and some cute wife, but I noticed y'looked kinda lonely. Y'didn't talk'ta any of the ladies where y'work it seemed and then when y'bitched at me for callin' you boring… Let's jus' say I wanted t'find out."
The corners of Craig's mouth drooped a little further, "Why?" he asked, kind of annoyed that Rick had made such an assumption about—He stopped and stiffened for a moment. Well, mission fucking accomplished, he realized, he now felt bad for assuming anything about the UPS guy.
Rick grinned, knowing he'd gotten his point across, "Y'got mad and saw y'had some fire in there."
Craig hadn't expected an answer after Rick had gotten his little revenge, but the answer had him turning a little pink. He ground his teeth to try to get himself back on track and not… He didn't even know. This whole charm bit was very much offset by the fact that he was wearing a dress and sitting with a pervert. Suddenly, a few more waiters appeared, laying down covered plates in front of them. It all came pretty quickly, course after course all with small servings, but it was all amazing. He felt like everything went by in a blur because suddenly he was holding a glass with a splash of red wine in it over a scrap of something that was both delicious and chocolate. Rick's arm didn't ever move from around his shoulders.