Memories - Permission to Ask

It was a few months before we got engaged, I was at Emily's house, dressed feminine, but not overly elaborate, just a simple satin chemise and panties, when she got a box out of her closet.

"What's that?" I asked.

"Just something I picked up for us," she said, opening the box.

"Whoa," I said, seeing what as in the box, "that...that's whoa..." The lingerie was elegant, sexy, pretty, feminine, enticing. "What...what's the occasion?" 

She smiled, shrugged. "Well I've been talking to this boy I've been dating about getting married and he's kind of feminine, and I just thought, before we got serious serious, maybe I should focus more on his girl side."

"Emily, this is so...elegant," I said, "are you...are you sure?"

"Sweetie, you spend most of the time you're here wearing pretty things, do you have to ask if I'm sure?"

"I just...I mean...I worry you'll want to marry...you know...you won't want me to be...like this," I said.

"I want to marry you," she said.

"Husbands are supposed to be...masculine," I said, blushing.

"Wives aren't," she said.

"Wife?"

She shrugged. "Maybe."

We had dinner, some wine, ended up in the bedroom where I pampered the love of my life, feeling the tug of the garter straps on my stockings as I kissed her and licked her, feeling soft nylon rub on soft nylon. She pulled me to the bed and instinctively, I was on my knees between her legs, licking her, touching her, tasting her.

"You're so good at licking pussy," she said pulling my face to her, "the best."

"The best?" I asked.

"By far," she said, leaning back, moaning, "like the universe giving you a skill to make up for other things."

"It...it's my favorite thing," I said. "I'd do this before anything else."

"Did they appreciate it as much?"

I knew who she meant. "Not...not like you," I said.

"The key insight I learned," she said in between deep breaths, "is that the more feminine you are the better you are at it."

"I just feel...when I'm feminine..."

"What," she said, voice hazy, lost.

"Like...like I want to serve you," I said.

"Someday you're going to promise to serve me for the rest of your life," she said.

"I will," I said.

"I know."

She looked forward, locked eyes with me. "Be careful how good you are at this," she said.

"W....why?"

"No reason," she smiled.

Eventually she pulled me to her, my back to her chest, touched me, teased me, rubbed her stocking on mine, kissed my neck, licked my ear. Her hand found the front of my panties, touched my untucked and very swollen penis. "Well this isn't very feminine," she said, lightly touching me through my panties.

"I...I'm sorry," I said, "I...I thought...I thought..."

"What?" she asked.

"I thought we could...that you'd..."

"You have to say it, love..."

"I thought...I thought you'd want it...I thought you'd let me...I hope you'd let me...you know...put it...put it inside you."

"You're such a sissy," she giggled. "The men I've been with tell me they're going to fuck me, the pretty boy I'm going to marry tells me he hopes I'll let him put his pretty little penis inside me."

"Emily..."

"Is that what you want, my love? I buy us pretty lingerie and you get to asking me to let you put your little penis inside me?"

"Please," I begged as she touched me.

"You're so cute when you beg," she whispered in my ear.

"I...I'm sorry," I said.

"Sorry?"

"For...for begging," I said.

"Oh," she said.

"Oh?"

"I...I didn't mean to bring up bad memories," she said, "I assume she didn't...of course not...most women don't like it when guys beg...it's not very...masculine."

I moaned as she rubbed me, her words humiliating, but her touch so erotic.

"She...she didn't like it," she said.

"I imagine not. I wouldn't either, normally. A weak boy, a beta boy, begging, would normally be such a turnoff, but when it's my pretty little sissy...I get all wet. Knowing how badly you want to put your little penis inside me makes me all tingly."

"Emily..."

"Beg..."

"Please..."

"Please what..."

"Please...please can I put it inside you."

"What?" she asked.

"What?"

"Put what inside me."

"My...my penis," I said.

"Your penis?" she asked.

"My...my little penis...please may I put my little penis inside you?"

"It's so ironic..."

"What is?"

"Dressed so pretty thinking about your little penis."

"I...I'll lick you," I said, "I mean, I...all I need...all I want is to lick you."

"No, love, that's not all you want...tell me what you really want and I'll say yes."

"Emily..."

"Be honest and I'll say yes."

"I...I want to...to put it inside you and...and then...lick you...lick you clean."

She giggled. "Yes," she said, turning over, pulling my penis free from my panties.

"Yes?"

"Yes," she said, "yes...as long as you lick me clean."

"I...I'll try," I said, knowing how my libido evaporated, how easy it was to promise, how hard to fulfill.

"No, love, you will. You'll put it inside me, squirt inside me, then ask, then you will."

"Yes," I breathed, incredibly turned on, "yes."

I moved to her, paused.

"Go on," she said, "go on."

"Em..."

"Go on," she encouraged me, touching herself, fingering herself, "put it inside me."

"Em...I..."

"Go on..."

I paused because I was soft, I paused because I was no longer erect. I paused, willed myself to grow. "I..."

She reached for me as if to pull me into her, felt me. "You...you're soft."

"I...I'm trying..."

She smiled. "It's like you know."

"Em," I moaned as she rubbed me.

"It's like you know you it don't belong inside a woman; like you know you a sissy shouldn't fuck a woman."

"I...I want to," I said.

"Yet you're soft," she said.

I felt her take me, soft, move her wet pussy over me, squeeze me. "Squirt inside me, love, you don't have to fuck me, leave that to men, but squirt inside me so you can lick me clean."

We rubbed together, kissed, touched and I did. Without fucking her, I squirted inside her, slow, short releases over and over. "Such a good girl," she said over and over as I filled her, as we smiled at one another.

"You're not done," she said when I was done.

"Emily, I...can we...can I wait?"

"No," she shook her head, "you want it more when you wait, you have to ask now when it's difficult."

I looked at her, knew I had to, knew I wanted to. "Emily, may I...may I lick you clean?" I asked.

"Always, love, always."

I went back between her legs, saw the mess, more than I anticipated. Because I was soft, I was barely inside her, meaning my mess was right there, all over her lips. She orgasmed the instant my tongue touched her, the second I tasted her...tasted myself.

It cemented us, grounded us, that night, effectively her permission for me to ask her to marry her.