Daddy's Gift

Terry swung the suitcase onto the bed and unzipped it. Two nights he would be staying at Drew's place, not an ideal situation, but since Tabby would be busy for the next couple nights with Tim, and since Drew could easily take him to work in the morning, Natalie had given him permission for the sleep-overs. A part of him had hated that he was instructed to ask permission, a bigger part of him hated how great it had felt to follow those instructions, but Terry might as well curse the sky for being blue. He was who he was.

The bag open, Terry looked at what he had packed, Drew's plan come to fruition. During his last visit to the apartment, Drew had ordered the older man to stand still while he measured every part of his body; his inseam, his foot size, his chest, his ass... everything.

"It's for some clothes," Drew had said, which utterly confused Terry. Nobody had ever measured him for clothes before. It wasn't as if he could even have his own clothes. The whole idea was perverse! When questioned, the younger man clarified.

"For your wife," he said, "I'll buy them anonymously and get them delivered to your house. It's not fair that you wreck everything she owns. Maybe if I get her some clothes that are a bit oversized, then she can allow you to wear them."

Terry had stood dumbfounded as the tape measure wrapped around his waist. It was a revolutionary idea, one that had never occurred to him before. Still, she might see the anonymously ordered packages and discard them. It was a bit creepy to get clothes in the mail from someone you didn't know.

"Don't tell her that they're from me," Drew said, "But start asking to wear her sexier things, the ones she really likes. That way, when she sees the new stuff, she'll put it aside for you."

The plan had worked. Terry didn't know why he even doubted his daddy. Drew's idea about getting pills from his doctor worked perfectly. So had the idea about working out on his streaming site. In fact, every idea that Drew had brought to Terry had worked out the way that Drew wanted. He was beginning to wonder if he shouldn't just trust everything the younger man said, going along with his ideas happily. It wasn't as if he could disobey and of his orders anyway. That way at least Terry's life would be a little less stressful.

"Hurry up and get changed," Drew called from the other room, "I'm thirsty!"

"Yes, daddy!" Terry called back in the high-register voice he was beginning to perfect.

Quickly, he stepped out of Natalie's old dress that he had worn to work, folded it neatly the way she would have wanted him to, and placed it on top of Drew's dresser. Then he slipped out of her panties, an older pair that had begun to fray. Now naked, Terry returned his attention to the suitcase.

The panties he slid up his legs were black and lace, brand new. It was a strange experience. Not only had he never worn something brand new, but it was also something that perfectly fit him. It was amazing. Was that what men like Tim felt like every time they got dressed? Not strangely restricted, mixed with a sense of guilt for ruining another set of clothing?

Then came the bra. It matched. In the past, Terry had gotten away without wearing bras. No reason to ruin another item of Natalie's wardrobe, but this was a 'Terry-sized' bra. And since his relationship with Daddy Drew had begun to evolve, so had the orders incorporate bras into his outfits whenever possible. "It looks sexier," he had been told.

A garter belt came next, followed by a set of black stockings that he fastened on. In the mirror above the dresser, Terry could see his reflection, a middle-aged man wearing lingerie. It wasn't something he'd never seen before. What was new, though, was how well it fit. Terry looked amazing. Natalie's new outfit was perfect for him. He'd never felt so attractive. Was that how he would feel all the time once his workouts had paid off and his pills had done their job?

Then came the pièce de résistance. It was something that Natalie would never wear.. Terry had been surprised when she hadn't immediately thrown it away. Maybe she had been wondering if Tim might be interested in some roleplay. Whatever the reason, it had ended up in the pile that she had put aside for Terry to wear that morning. Again perfectly sized for Terry, an extremely short black and white maid outfit. Without hesitation, Terry pulled it on and fastened it shut. The frilled hem was at least three inches above the top of his stockings, something the father of two thought he should be embarrassed about, but he couldn't bring himself to feel that way. It was the first dress he'd ever worn that was exactly his size, and he absolutely loved the feeling. He wished he could wear that outfit every day!

There was a pair of patent black high heeled Mary-Janes in the suitcase, Natalie's new shoes that Drew had ordered, in Terry's size. He stepped into them and fastened the buckles. No toe pain. Terry's feet were never that big, but they had certainly been bigger than Natalie's. Finally he could stand up without discomfort, for the first time in his adult life. It was amazing. He walked around the room, the clothes he was wearing feeling good, not punishing. Tears began to form in his eyes. The gift that Drew had given him, the gift of comfort, by buying new clothes for Natalie, was the kindest thing anyone had ever done for him in his life. He only wished he could come up with a way to thank him properly!

"You almost done in there, sweet-cheeks?" Drew called from the other room.

"All done, daddy!" Terry called back, excited that he knew exactly how to thank his younger coworker. He knew because Drew had been showing him what he liked every time Terry came over, and it was about time that Terry put his heart and soul into it.