Friends

I walked into the study, shut the door behind me, turned and looked at the three people across the room. My wife and her friend, Jenny, sat on the couch, watching me; Jenny's husband, my golf partner, was sitting on the floor, naked, his erect member bobbing up and down, his embarrassed obvious.

"My god, those legs are to die for," Jenny said, touching my wife's arm.

"Heels and hose never fail," my wife said.

"And so poised...what do you think Walt?"

I looked at my friend; his face was as pink as my uniform. "They...they're..."

"Pretty is the word you're looking for," Jenny said. She uncrossed her legs, recrossed them so one of her heels was close to his erection. "This gives it away," she said, lightly tapping his erection with her heel.

"So?" my wife asked. "Yes?"

"I brought a bra and panties," Jenny said.

"Black?" my wife asked. Jenny nodded. "Perfect," my wife said, looked at me. "Sissy, go lay out a black garter belt and stockings and one of your black uniforms."

"Which...which one, Ma'am?" I asked my wife.

"The satin one like the one you're wearing," she said. I glanced at Walt, saw the horrified look on his face. 

"Walt, go with sissy," my wife said, "she'll help you dress."

Walt looked at Jenny. "Jen, please," he begged.

She glared at him, took the small bag from next to her, held it out to him. "This is the bra and panty set," she said, "take it with you." Her tone was firm, like she needed to steel herself to go through with her decision. 

I felt for Walt, felt this was all my fault. Without being instructed, I walked to Jenny. "May I Ma'am?" I asked her, reaching for the bag.

Jenny looked from me to her husband and back to me. She handed me the bag. "By all means," she said.

I was inches from Walt, saw him staring at my hose covered legs, saw his erection bouncing. He was longer and thicker than me and in a way I felt bad for him. "Come on, Walt," I said, holding a hand towards him.

He glared at me, ignored my hand, looked at the two women. He sighed but stood to follow me.

"This is stupid, Eric," he hissed at me as soon as we left the study and I closed the door.

"Erica," I corrected him, "I...I go by Erica."

"Whatever," he said as he followed me to my room, the small maid's room in the back of the house. I opened the bag, took out the bra and panties his wife had brought for him. They were of vintage style, perfect to hold breast forms and to tuck. 

"You...you need to make that small," I said, pointing to his erection. "You need to tuck it between your legs, the panties will hold it in place."

"Tuck it?" he looked at me. I shrugged, got red faced as I explained tucking. "Why?" he asked.

I looked at him like he was slow. "Sissies aren't permitted those," I said.

"Those?"

"E...erections," I stammered, "those...those are for men."

"Jesus, Eric," he glared at me, "I'm not a sissy."

I took a deep breath to calm myself, knew he knew no better. "Erica," I said, "just put these on, make it small, and tuck it."

"I can't," he said.

"Can't put them on? I thought you agreed to..."

"No," he looked down, "I can't...I don't know how to...to make it small."

"Just put those on," I said.

"Eric...Erica," he corrected himself, "I...I don't know..."

I took the panties from him, held them open. "Just step into them," I said, "we can't dawdle, they'll be angry."

He took the panties, stepped into them, pulled them up his legs. His erection was bigger than mine were but the panties at least covered it, though the bulge was unsightly. "You need to make is soft and small," I said.

"I...I can't," he said, on the verge of tears. 

I sighed, tried not to think of him as my golf partner, tried to think of him as a sissy who needed direction. "Let me help," I said.

"No," he shrieked, took a step back. 

"Walt, not like that," I said, "my god, what's the matter with you. We're not allowed to do that even if I wanted to, which I don't. Just...dammit, just hold still. My hands are cold, you'll...you know..."

"You better not..."

"I won't," I said, "god, will you just stop." I didn't want to tell him more, didn't want to tell him what sissies could and could not do, afraid he'd shriek and run in horror. "Don't think about sex," I said, reaching for him, "think about something mundane...the last hole of golf you played."

"Damn, your hands are freezing," he said as I reached into his panties. 

"Tell me about the 18th from last week."

He went through his par five bogy shot by shot, his erection subsiding with each one until he was soft enough to tuck. Quickly, I bent him back, pulled his panties tight. "There," I said, "all tucked and safe."

"You do this?" he asked, looking at his penis tucked behind him in his panties.

"Basically," I said, not wanting to explain that I wasn't tucked because I was locked in a small chastity cage, not wanting to make him think that was his future as well, not just not permitted to grow erect, but actually prevented from doing so, locked to prevent him from doing so. Locked to deny the ability to grow, locked to deny the ability to cum.

"For how long?"

I shrugged. "I better help with the bra; it's tricky at first but you'll get the hang of it."

He scowled at that but held his arms out while I showed him how to fasten it in front and spin it around. "You learn this way first," I said, "then how to do it from behind."

I saw him looking at my chest. "Breastforms," I said, "silicone. They look and feel real. I have a set for you."

"You're serious," he said.

"Sorry, yes," I said.

It was the garter belt and stockings that derailed things, slightly. I helped with the stockings, of course, attached the garter straps, of course. Doing the first front strap, it was an accident, the back of my hand rubbed against his tucked penis. "Ohhhh," he moaned involuntarily. Well, at least it looked like an accident.

"S...sorry," I said, quickly moving my hand.

The second time, though, was on purpose, for I knew teasing a newly feminized boy was the best way to make sure there was an indelible connection between feminization and sexual excitement. But it wasn't an accident, it was something I was ordered to do by my wife.

"Mistress, please," I'd begged her, not wanting to touch my friend this way. She didn't even answer, instead just glared at me. "Yes, Ma'am," I said.

"Eric," he yelped when I rubbed him back and forth.

"Erica," I corrected him.

"What...what are you doing?"

"Nothing," I said, moving to the other straps, but returning to touch him again.

"Eric...Erica," he moaned.

I looked up at my friend, in a way sad, knowing what was in store for him. "Let's finish getting you dressed," I said.

Dressed like I was, black to my pink, he looked at himself in the mirror, then me. "You're so much prettier," he said.

"Hair and makeup," I said. "Come on, we have to go."

I took his hand, the hand of my friend, my golfing partner, led him back to the study where our wives were waiting. "Did she give you any trouble?" my wife asked.

"No, Ma'am."

"She's tucked?" 

I looked over at Jenny, nodded. "Yes, Ma'am," I said, "I helped."

Jenny smiled widely, knowing that was all it would take to condemn her husband to the life I led, the life of the sissy.