Intimate Wear

"Sure, you got it. I'll come back to pick you up. When do you think that you'll be leaving?"

"Oh...I don't know. I have so much to do. Don't worry. Jannine and I will be fine, and she can drop me off on her way home."

"I'll come back to help."

"No, Henry. You need your rest. You've earned it. I promise to not be too late. I'll see you later." Henry left without knowing what "later" meant. But he had tasks to do for Courtney, and he wanted to go check on his car. The shop was only a few blocks away, so he popped in to get the bad news of a $ 5000+ repair bill to fix his vehicle. Since he needed and badly wanted his car back, he agreed to the price. Then he went straight to Courtney's condo grabbing dinner at a fast-food drive-thru. After parking in her spot, he stopped at the concierge desk where four packages awaited him. They all had Courtney's name not her "business" title. So he signed the sheet and took them upstairs.

Treacher meowed at Henry as soon as he was inside the condo door. The feline rubbed between his legs and led him to the kitchen where his obvious task was to fill two bowls with a can of cat food. He saw both animals partake of their meal, so he moved on to the inventory of the packages right after putting his jacket on an empty hanger in the front closet. The four containers were of various sizes of opaque plastic bags, the kind used to ship most clothing orders. Two were from a company with the initials, WT, another was from London with markings, KMD, but the last was from the well known Frederick's of Hollywood.

Courtney sure had a thing for quality lingerie. Henry thought about her wearing such a varitey of outfits for her "clients" on the internet and cringed. He had thought that he could be okay with her continuing that business venture of hers, but that was before he was sure that he had real feelings for her. Up until right then, he had been little more than curious about the details of her apparently lucrative venture. Now it was a case of wondering just how much information that he could handle.

Henry got out his phone and texted Courtney about the details of her packages save the contents as he was yet to get instructions to open them. She texted back, "Only 1 frm Frdrks? Whats in it?"

"U want me to open it?"

"Yes, and scan the invoice." Henry shrugged and tore open the grey plastic bag from Fredrick's of Hollywood. He set aside the contents which were clear plastic packets and grabbed the invoice. While setting up his phone to capture the sheet, he noticed that it listed a red and black dot-lace short robe, a black lace plunge bra a red panty with black lace trim and one red lace babydoll on back order. He took a picture of the invoice and sent it to Courtney. While he was regathering the packets, her text came back. "Damn! They said it was in stock. They do this too often. I'll email them." Another text came soon after. "Could you just put the rest in the bedroom closet? The Frederick's was mainly for you, anyway. So enjoy. I'll be home before midnight."

Well, that meant that Henry would be staying the night again. He had Courtney's keys and would have to let her into the condo, assuming that her concierge would let her in the building late after she got a ride from Jannine. He called down to the desk, and the young man assured him that he would be available to let her inside. What truly perplexed him was her comment about the items from Frederick's being for him. After he put the the unopened packages in her bin marked "New," he took the clear plastic covered items to the bed. It was only 7:30 PM by his watch, but with little sleep from the night before, he wasn't going to be awake at midnight. So he texted her that he would be napping and for her to call to wake him when she was on her way. She sent back, "OK." with a smilely face.

Back in Coutney's closet, there was a hanger marked "H'" containing a soft burgundy robe. Henry took the robe off to use the hanger for his pants and dress shirt. There were slippers in his size, so he took them and put his shoes in their place. As he closed the closet door, he tossed the robe onto the chair on the right side of the bed, the same side he had slept on. Curiosity led him to sit on the bed and open the clear plastic bags. Her permission had created a dilemma between the taboo of his gender even touching such garments and the thrill of the previous night of enhanced intimacy. She wasn't there to prompt or witness, so he was free to do anything from putting them aside to trying them on. It felt odd, but after a minute of staring at the items on the bed, the desire to try them on became clear.

Henry took the black bra and slipped his arms through the straps. Thankfully it hooked inthe front saving himself from trying a maneuver perfected by women over the decades of blindly reaching behind to hook the back. Once the straps were adjusted, the bra felt comfortably tight against his upper chest. Moving on, he replaced his own underwear with the matching black sheer panties. His cock was fully visable yet secure inside. Finally, he completed the outfit with the short black chiffon robe and got up to step in front of Coutney's mirror. She would have looked much better in such an outfit, but his appearance did not seem to repulse him at all. The bra had a push-up effect. It didn't give him boobs, but it certainly enhanced his upper chest. With that, Henry turned out the lights and climbed into the bed under the comforter. He touched him self through the lingerie for a minute, but exhaustion won over excitement. He soon drifted off.

In a dream, Henry found himself dressing Courtney as if she were a doll. She only smiled at him as he changed her outfits from pink and frilly to bold black and strappy. When he changed her, his outfits magically morphed to compliment hers. His body also changed to smooth and hairless but not quite feminine. He looked in to a mirror to see that he still had facial hair, a goatee, and he was hung like a porn star. Then there was something stabbing him in the back. It was his old gym teacher, Mr. Lake, who was only the size of a cat yet somehow was jabbing him in the back with a knife under his shoulder blade.

Henry's phone woke him. It was Courtney, and she was on her way upstairs. He would meet her at the door. As soon as he put his phone down, he noticed that there was something, poking his right shoulder. The tag was still on the bra and hit him right where Mr. Lake's knife had. Quickly, he got up, secured his robe and went to meet Courtney. Through the front door's fisheye peep-hole, he saw her approach. He opened the door a crack and stepped back into the hallway. She came in, gave him a smile that showed relief and near exhaustion and hung up her coat and purse. "Oh thank you, Henry. I don't know how I could have gotten through the day without your help." She came and gave him a quick hug then slid past him to the kitchen. He followed her and sat on one of the stools at her counter while she grabbed two glasses from her cabinet. Turning back to him, she asked, "I need something to help me wind down. Can I get you some wine or a drink, too?"

"No thanks. I'm good."

"Well, I'm having some. Let me know if you change your mind." Courtney reached into her fridge and pulled out an already opened bottle of white wine. She poured herself a generous glass which she downed in a couple of gulps. At last she looked up and noticed Henry's attire. "Oh good! You found the robe...It looks really good on you!"

"Yeah. It feels nice, too." Henry reached over and pulled Coutney's hand to his lips and kissed it softly.

"Oh Henry. I'm sorry, but I don't think that I'm up for anything tonight. But please stay. I wouldn't mind waking up to you again."

"Okay...About that, though. Are there any...ground rules for my staying over?"

Coutney had been about to take another drink but she sighed and said, "Oh boy! Do we really have to discuss this, tonight? I'm exhausted...I want you to feel welcome to stay and sleep here whenever you like. But there are times when I'm doing, you know, my internet business, when you probably won't want to be here..."

"Yeah. About that...I was thinking that there could be a way to work something out. Now, I know that you say that you're really happy doing what you do in this business of yours. And that it's rather lucrative...But what if you had someone to share expenses with? You wouldn't have to..."

"Henry!" Courtney slammed her nearly empty bottle of wine on the counter. "I am not giving up my business for you!"

"No no, Courtney. You didn't let me finish. I was going to say that we...or you wouldn't need your salary at S & D if you had a roommate. That way, you could work at the business all day. As long as I'm the only one you do things for, in person, and as long as it's legal, I don't care what you do for a living."

Courtney tilted her head at Henry. Then she pulled her tablet out of her briefcase and set it up on the counter where they both could see. "Let me call up last year's revenue from my tax return and my estimated hours for the state B & O tax...Yeah, I did pull in a lot more per hour than my salary at S & D. I show between sixteen and seventeen hours a week. So, if I increased that to, say, thirty-six, let's say that I merely double the revenue. And if we add another salary, say yours, we could easily afford a bigger place where I could have a whole room dedicated to the business...and a bedroom for each of us."

This time, Heny looked at Courtney with confusion. "You want separate bedrooms, then?"

"Just kidding, Henry. I don't ever want you to be away from me again,..ever."

"What are you saying, Courtney? Are you really ready for...this?"

"Yes, Henry. I'm ready to be a couple with you, whatever you want to call it. You can change your FaceBook status to "In a relationship" with me. Okay?"

"Yeah. More than okay." Henry stepped around the counter into the kitchen. Courtney slid into his arms for a welcome embrace. They kissed for a minute, then just held each other for a couple more. At last, Henry thought that he heard and felt her give a sob. "Are you okay?"

"Un huh... It's just that this isn't the way I'm supposed to feel. I never wanted to cross that line and want someone like this. I have no leverage, now, and that scares me."

"Okay...How about I give up all my leverage, too...I love you, Courtney. I can't be without you, either. You could take my heart and stomp on it, and not only would I have no power to stop you, I'd never get over it."

"No. I couldn't. I could never hurt you...or let anyone else...I love you, too." Henry pulled back and started to get down on one knee. "Oh no! Not that! I'm not ready...we're not ready for that!"

Henry got back up. "Okay...But taking that step doesn't scare me. Certainly not like I thought it would. It actually, kinda felt right."

"I can see that it might...for you...and maybe sometime later, for me. But that's too far...Sorry."

"No. I'm the one who should be sorry. I shouldn't...I don't want to scare you...or push you. I guess that one of us should try to stay rational. It's just that I have no experience with feelings like this...Oh man, now I'm tired again." Henry held his arms out, and Courtney melded into him with her head on his shoulder. "Let's go to bed." She nodded, and they started out of the kitchen towards the hallway to the bedroom. Along the way, Henry reached for the light switch to the living room overhead, but he was given a tug away. She swung in front of him and looked him up and down. Then she reached for his robe ties, pulled them and his robe came open revealing what Henry had completely forgotten, his bra and panties.

"Oh Henry! We're not going to get to sleep much tonight. Are we?"

"I could always just take them off, and we could pretend you didn't see this."

She shook her head. "It's too late, now. Someday, I'll be able to keep my hands off you when you're dressed like that. But not tonight. You're my gift that keeps on giving."

"And you're mine."

The End