Drew and Terry

Drew has always loved the phrase, “dolled up”. He loved it when, as a child, he played with his GI Joe dolls, helping putting the patriotic heroes in beautiful outfits like wedding dresses and ball gowns. He loved it when, after he hit puberty and his body began to change, his father took him to the mall to for his first makeover. He especially loved it when he met his best friend Terry.

Terry was different from every man Drew had ever met. Yes, in some ways he was exactly like every other man, big breasts, smooth, hairless body, beautiful girlish voice, but those weren’t the ways that mattered.

Although he was young, Drew was sure that if there had been anyone else on the planet like Terry, he would have heard of it. The complete absence of authority combined with the inability to own his own clothes made Terry an incredibly unique person.

An incredibly unique person who Drew loved to get dolled up!

It was not dissimilar to his time with his GI Joes. Terry would come over, and Drew would get to have fun dressing him up! Unfortunately, Drew’s clothes didn’t quite fit perfectly. Terry’s breasts and ass were significantly more pronounced, much like those of Terry’s son, Tim.

What Drew was known for at work was innovative thinking. On the day Drew was hired, old man Rothschild, wearing a sparky pink cocktail dress that looked so sophisticated, told him that he was to think outside the box if he was ever going to get ahead.

And so he had. It had hurt his brain a bit to come up with the idea, but once he’d had it, it had seemed so obvious!

Since Terry was stuck wearing his former wife’s clothes, why not give Terry’s former wife clothes that fit Terry, then she could let him use them! In a way, it wasn’t far from going to the store to find new outfits and accessories for his dolls as a child.

It had taken a while, but finally, after a few weeks, Terry had shown up for a visit at Drew’s in one of the outfits.

“She said I could use it!” Terry had said excitedly, “She seemed happy that I wouldn’t be stretching out her good clothes anymore!”

The father of two stood in Drew’s doorway looking incredibly pleased. He was wearing a purple faux fur top and skirt, perfectly contouring the older man’s feature, showing off both his smooth belly and his long legs.

“Wait until you see what comes in the next package,” Drew said with a grin, “I hope she likes it!”

“Not that I’m not happy,” Terry said, wiggling into the apartment to start his regular cleaning routine, “but isn’t it a little weird for you to be buying Natalie clothes? I mean, you don’t even know her, and if Tim ever found out…”

“He won’t find out,” Drew said, “all orders are anonymous. There’s no way for anyone to track them to me.”

Drew watched his best friend bend to pick up some dishes from the coffee table, then straighten to carry them to the kitchen. He’d be at it for an hour at least. One day Drew would learn to pick up after himself, but with Terry around, he wasn’t motivated to speed up that learning process. It was just so amazing to have an incredible friend like Terry, who didn’t mind being ordered around a bit, and who also wasn’t bad to look at!

Speaking of looking, watching Terry tidy reminded Drew of the craving he had been suppressing.

“Terry, sweetie,” he said in his most syrupy voice, “leave the cleaning for now. Why don’t you come to the bedroom for a bit. I need to get something in my mouth, and I think you might have exactly what I need!”

“Oooh goodie!” Terry squeaked as he scurried into the bedroom, “I hope you’ll share, Daddy. I’ve got a craving, too!”

“We’ll see what we can do, sugar.”

And so Drew followed his best friend into the room which had once only been used for sleeping, but now was used for so much more. Think outside the box! Good advice. That’s how he lived his life, and it seemed to be working so far.