Memories - Nighties

I came home, found Emily at my place, unexpectedly. It was early on still, her being there was not wrong, it just wasn't common yet for her to be there without me. 

"Hey," I said, finding her at my kitchen table working.

"Hey," she said, looking up, smiling, focusing again on what she was doing.

"What's going on?" I asked.

"I had a thing up here so thought I'd surprise you."

"Well I'm surprised," I said, thinking nothing more of it.

It wasn't until later that I realized there was more. "Can I ask you something?" she asked, pouring us each another glass of wine.

"Sure," I said, recognizing that tone she had.

"I might have done something I shouldn't have," she said.

"What? Work?'

"No, no," she said, "not work."

"What?"

"I...I kind of went through your drawers. You know, the ones in the back of your closet."

"W...why?" I asked, my senses tingling, knowing what was in those drawers.

"Curiosity," she said.

"Emily, I...those...that's private stuff."

She looked at me. "Not too private," she said. "Anyway...you have...everything is organized how I'd expect it except..."

"You went through my lingerie drawers?" I asked, sighing inwardly.

"I was curious," she said, "you've showed me things but...I wanted to see everything."

"Except what?" I asked, finally.

"You have a drawer of...well... negligées...but they were folded with bras and hose...it's just...unexpected."

I looked down, knew my face was red. I said nothing.

"Sweetie, you know it's okay," she said, touching my arm. "This isn't a shit I found my boyfriend's stash of lingerie conversation, we're well past that, aren't we?"

I swallowed. "I...I suppose," I said.

"You're embarrassed."

"I just...s...some..." She looked at me like she was waiting for an answer. "I...I like to...sleep in those...you know, when...when you're not here."

She sipped her wine, considering. "They're pretty," she said, "you have good taste."

"T...thanks," I said, still looking down.

"Why the other things, though? The bras? The hose?"

"Emily..."

"It's a fair question," she said, "I...I want to understand."

"Em..."

"We talked about this...no secrets, remember?"

"I...I sleep in those, too."

"A bra and hose?"

I nodded. 

"Why?" she asked, nonchalant.

"The...the bra holds...holds my..."

"Breasts, duh," she said, "I get it, that makes sense. What about the hose? You sleep in pantyhose?"

"I...I mean..."

"No secrets," she said.

I bit my lip. "They...they're control top...they...I don't like to...you know...what boys do in the middle of the night."

She looked at me, a confused look.

"Swell," I said, my voice barely a whisper.

"Swell...my goodness...duh again...swell."

"I...I shouldn't...I mean...when I dress..."

"No," she said, "no you shouldn't. I...the hose stop that? All night?"

I nodded. "Tucked, the...the control top...I can't...I mean...it tries, but..."

"But you stay soft?" she asked. "All night?"

I nodded. 

"Soft and pretty," she said.

I shrugged. 

"Can...can I see?" she asked.

"A...a nightie?"

She nodded. "An outfit...you sleep in," she said.

"Emily..."

"Please," she asked.

"Emily..."

"I want to see," she said, "please. I've already seen other things, I want to see this, too."

"Are you sure?" I asked, afraid.

"I'm sure," she said.

"I...I should shower," I said.

She smiled again. "Take your time, love," she said.

**********

Thirty minutes later, give or take, I emerged from the bathroom, showered and dressed, wearing a satin nightie, a bra, breast forms, and hose. "Emily," I said, shocked. 

Emily was on the bed; she too had changed, not into something of hers, but of mine. "Hope you don't mind," she said looking down, "I borrowed something."

She was wearing a teal, black lace trimmed slip, a coordinating short robe, and hose.

"God," I mumbled.

"You like? I thought I'd try it, thought we'd try it...together," she said.

"S...sleeping together?" I stammered.

She nodded. "Is...is that okay?" she asked.

"I...I suppose," I said, feeling my tucked penis already trying to swell.

"Sleeping together," she said, "just sleeping."

"Em..."

"You said you wore hose to keep it...to keep it soft, right?"

"Y...yes," I said.

"Is it tucked? Soft?"

"Yes," I said again.

She patted the bed. "Come to bed with me, my pretty little boyfriend."

"Emily..."

"Come to bed with me, my pretty little girlfriend?" she said.

I swallowed again, moved next to her. "You sure," I asked.

"I'm sure," she said, her nylon covered leg touching mine.

"Oh, god," I shuddered.

She giggled. "Smooth, isn't it?"

"Y...yea," I said.

"My pretty little boy with his nylon fetish," she said, rubbing her leg on mine, putting her hand on my soft nightie as my hand found hers.

"I..."

"Shhhh," she said, "you wear them to stay tucked and soft?"

"Yea," I said.

"I respect that," she said, "it's probably better that way, so let's make sure."

"Make sure?"

"Make sure you stay tucked and soft tonight or anytime you wear this to bed with me."

"But I...I mean..."

"Shhhh," she said, "tucked and soft, I respect your wishes, I promise."

"Emily, I...I don't mind..."

"Shhh, I know...you shouldn't mind...you shouldn't be ashamed at all...that's natural, really, to want to make sure you stay small, soft, feminine."

"Oh, god, Emily," I moaned.

"Hmmm, you like that, don't you? Being soft and feminine for me...you don't have to be ashamed."

"But I...I mean..."

"Do you feel feminine when you're tucked and soft?"

"Y...yes," I said.

"More natural?"

"I...I suppose. But don't you...don't you want..."

"Want what?"

"Your...your boyfriend to be...mas...masculine?"

"Usually," she said, "that's my type...usually...but not with you, you know that. All the men you competed against, you were the one that won me. I could have any man...but you're the one I want."

"But I can't...I never can..."

"Never can what?"

"P...please you," I blurted out.

"Oh, love, no, of course not, not with that little penis of yours, no, not with that, never with that, not inside me."

"I just...I want..."

"To be my man? Honestly, love, is that what you want?"

"S...sometimes," I said.

"But here you are, my pretty girl, instead. Isn't this what you really want? To be my tucked, soft, feminine, pretty girl?"

"Yes," I blurted out.

"I wore pantyhose just for you," she said, "you're wearing them to stay tucked and soft, I'm wearing them, too."

"Why?" I asked, enjoying the sensation of her nylon covered leg rubbing on mine.

"Hmmm," she purred, "because I love the feeling of our legs rubbing together..."

"And?" I encouraged her.

"Because I love being girls together," she said.

"And?" I knew there was more.

She smiled, a big, teasing smile. "Pantyhose, not stockings, just to reinforce that this," she touched herself through her panties, "this is off limits to you, to reinforce that this," she reached for and touched the front of my pantyhose, "your pretty little penis doesn't belong inside me."

"Oh, god, Emily," I moaned, "please..."

"What?" she asked, an innocent look on her face. "Isn't that why you wear them? To stay small, soft, and feminine."

"Yes, but..."

"Isn't that what you want? A woman telling you that you don't belong inside her?"

"Emily...but I...I want..."

"Isn't that what you said shamed you? Knowing you were small...quick...unable to...to be a man," she said, rubbing me.

"I...I just..."

"Isn't this why you dress like this? Isn't this what you always wanted? A woman to tell you it's okay to stop pretending to be a boy and embrace being a girl?"

"Yes, but...but I...I..."

"Isn't this what made her cruel? Not realizing you couldn't be the man, not realizing it's better for you to just be a girl?"

"But don't you like...like when we...when we do that?"

"Do you?" she asked me.

"Yes," I said.

"Even being so small?" she asked.

"Em..."

"So quick?"

"I..."

"So...disappointing?"

"Emily..." I groaned, "I...I thought you...you never...you're never cruel..."

"Do you like being inside me?" she asked.

"Yes," I blurted out.

"I like it too," she said, surprising me.

"But I can't...I never...please you," I said.

"Not like a man," she said, "not like any of the men I've been with, never like that."

"But...but why do you like it if I never...if I can't..."

"Make me cum?" she smiled. 

"Why do you like it?" she asked.

"I...I like being inside you," I said.

"Because you're so...warm...and wet...and..."

"And..."

"It's so...intimate."

She smiled. "Intimate...that's the word. It's so intimate. I know you're ashamed, I know you try, but it's so...intimate. When you squirt inside me, I know you're conflicted, but it's intimate...safe...when you know you're going to cum so quickly and try so hard to make it last but never can...I know you're ashamed but it's safe with me."

"Emily..."

"Love?"

"Can I...can we..."

"Shhhh, not tonight, love, not tonight. I'm not saying never, but not dressed like this, this is when we're just girls."

I looked at her, felt overcome. "I...I love you," I said.

"We need more of this," she said.

"This?"

"Honesty," she said, giving me a serious look.

"Yes," I said.

"Do you like being my boy or my girl?"

"Both," I said.

She nodded. "Good, then we need more of this, too."

"This?" Meaning, what other this.

"This," she said. "You're my boy all day, even if you're in a bra and panties, so we need more of this at night. One of your sexy nighties or slips or babydolls and your soft pantyhose and your pretty breasts. We need more girl at night."

"And..."

She smiled. "Soft and tucked, of course," she said. She'd moved so my leg was between hers and she was slowly moving her pelvis up and down, moving her nylon covered pussy against my nylon covered leg.

"Emily..." I said, watching her eyes.

"Safe sex," she giggled. "Chaste sex. Chaste intimacy."

"Chaste?"

"Chaste," she said. "The pantyhose just makes sure we...we don't get carried away."

She moved again, pressed against me. "Intimacy without...going too far...chaste intimacy."

We rubbed, gliding easily as our nylon covered pelvises pressed against one another. I knew she was wet, knew my small, tucked bulge was rubbing against her as we kissed. "Oh god, yes," she moaned, "yes."

"Emily, I..."

"Don't stop," she said as she shuddered, "don't stop."

I didn't, but just like being inside her, I couldn't stop myself either. Even soft and tucked, the friction of our nylon covered humping pushed me to and over the edge. It was different from being inside her, my orgasm didn't stop what she was doing, what she wanted. She didn't need me hard, didn't need me in her, she just needed to press against me and my orgasm didn't stop that.

When she climbed down, she smiled, exhaled. "Chaste intimacy," she said.

"C...chaste intimacy," I said.

"You made a mess," she giggled.

"I'm sorry," I apologized.

"Do you want to...you know..."

"I..."

"Sorry, let me rephrase that," she smiled. "I want you to."

"Em..."

"Shhh," she said, pulled me to her, pulled my face between her legs. "Pretty boys clean their messes," she said. "They always clean their messes."