Caught! - Sex Stories

Caught!

... turning to Nathan, “Have you picked a girl name yet?”

Nathan gave me a confused look, “Girl name?”

“A name for the girl you become when you’re dressed. It’s okay, we’ll get to that later,” I explained.

Linda came over to help us and I briefly explained the situation to her.

“Oh, that’s great, I remember buying my first clothes. It was so exciting getting clothes of my own instead of borrowing them.”

Nathan stepped back to look Linda over from top to bottom. “You mean you’re a…a…”

Linda cut him off, “I’m a girl now hun, and you can be too.”

“Wow! You’re beautiful,” Nathan blurted.

Linda smiled and took him by the hand, “Let’s find something pretty for you, sweetie.”

I chatted with Jenna as Linda tried to help an overexcited Nathan find the first lingerie of his very own. Nathan rifled through the racks and displays, ohhing and awwwwing over everything he picked up.

“He’s going to be a very pretty girl,” Jenna said, “ Where did you find him?”

“My ex-girlfriend’s brother,” I shrugged.

“Sounds complicated,” Jenna said, scratching her stubbled chin. “Who’s better, brother or sister?”

“I’m just trying to help him out a little, he’s really struggling with his sexuality,” I explained.

“I’d love to help her out, she’s going to be darling,” Jenna laughed.

“I’m sure you would, horny bitch,” I laughed back.

“Look who’s talking,” she snorted.

Just then Nathan ran up with an armload of clothes, “Look, they’re all so pretty.”

Jenna and ...

... I looked through the items one at a time, holding them up to judge how Nathan would look in them. It was hard to judge because they would all look amazing on his petite frame. Linda stood by offering advice on proper sizes and showing us a few sets she thought would be perfect for Nathan. One was the same purple and black set I had been wearing the night Christa walked in on me.

“Oh I have that same set, it’s my favorite,” I commented when Linda held it up.

Nathan grabbed it from her hands and held it against his chest, “We could be twins!” he exclaimed.

“Oh that would be hot,” Jenna leered at the two of us.

“Um maybe this one,” I quickly suggested, holding out a baby blue satin and white lace teddy.

“Maybe both,” Nathan grabbed the teddy from my hand.

We all laughed at his excitement and carried on looking through all of his selections. It took a while as he’d nearly picked one of everything in the store. In the end, Nathan decided on the purple and black bra and panty set that matched mine, the teddy, and a simple red thong and matching bra. I added the prices in my head and asked how much he wanted to spend. He answered that he’d brought plenty of money and didn’t care what it cost. We helped him gather stockings, a black garter belt, as well as a short blue satin robe to complete his outfits. Then Nathan saw the shoes. Initially, he wanted a pair of six-inch stiletto heels but we persuaded him to go for a much lower-heeled sandal to start with.

As we ...