Memories

 

A memory, from years ago, of Emily.

"Do you want to talk about it?" she asked, on her back in my bed, seeing my embarrassment.

"Not...not really," I swallowed. 

We'd made love our usual way for back then. 

Extended foreplay, virtually all of it me pleasing her, touching her all over, licking her all over (some things never change). 

Her touching me much less, reaching between my legs just now and then to give me a gentle touch, brushing against me then pulling me away when I did something she liked, using her soft hand as a subtle signal for what she liked.

In the end, she gave me a look, a whisper, "go ahead," she said, as if she was giving me permission, which even then, she was.

I remember it so well even though...well...

I was on top of her, rubbed agains the wetness, pushed inside her, pulled, back, pushed in again, thrilled, as always, by her warmth, her wetness, the closeness.

"Are you in?" she asked, innocently.

"Y...yea," I mumbled, thrusting.

"You sure?" she asked, moving a hand between us. "Oh, okay," she said, confirming with her hand.

I was dizzy, knew I should hold back, try to make it last. I knew I should pull out, do more with her, let myself calm down. But I was afraid if I pulled out, I'd finish just from that friction. So I held still, hoped a momentary break in moving would let me gather my thoughts.

But it didn't work. Instead I exploded inside her.

She saw my face, understood, giggled. "Well that was quick," she said said, an observation, no more. 

"Sorry," I said, mortified. I rolled off her, looked away.

After a minute I felt her hand on my back, rubbing it gently. I finally looked over at her, humiliated tears in my eyes.

"Do you want to talk about it?" she asked, seeing my embarrassment.

"Not...not really," I swallowed. 

"Sweetie," she said gently, "what's wrong."

"I...I'm sorry."

"Sorry? Why are you sorry?"

"I...I tried..."

"Tried?" she asked.

"To...to last," I said.

"Sweetie, you went down on my for an hour, I think were both pretty excited, that happens sometimes and...oh god, I get it."

"Get it?"

"You're self conscious, oh, sweetie, I'm such a fool."

"A fool?" I asked.

"That wasn't your first time wearing panties, was it."

"Emily," I gasped.

"It makes sense...you're such a tender lover...you're imagining..."

"Emily, stop," I begged, face red, I didn't want her to say it, speak it, was afraid she'd immediately bolt from the room, from my life.

"Why?" she asked.

"Because...because I...I don't...I can't..."

She looked at me, soft, tender. "You imagine you're a girl, don't you?" she asked, pressing on.

"Emily..."

"I can tell...when you're pampering me...you're imagining you're a girl."

"I...please..."

"I...I tried..."

"To make love to me like a man...of course...but you can't...mentally."

I was terrified. "I...I like...pampering you..."

"I know, it's so obvious, I know." She was touching my hair, my face. "You were so excited that night you wore mine, it's so obvious now."

"Emily, please, I...I didn't mean to..."

"Do you have some?" she asked.

"Have some?"

"Panties?"

I blushed, looked down, aware I was answering by not answering.

"Where?" she asked.

I shook my head. 

"Where?" she asked again.

I swallowed. "In...in a box...in...in the closet."

"Why not in a drawer?

"I...I moved them when...when you..."

"Of course," she said. "You didn't want me to find them, did you?"

I shook my head no. "Women don't..."

"Like boys in panties? I imagine most don't. But I already saw you in panties."

"That was...different...it was...not like..."

"Planned?" she shrugged. "I suppose not. But it was kind of hot."

"You mean that?"

"Yea," she said. "I mean, weird, at first, thinking that my boyfriend was sitting next to me wearing my panties. But then weird turned hot. And then you were so...eager..."

"You...you noticed?" I smiled, remembering.

She nodded. "Yea...I didn't think...I mean...I didn't put it together...but now..."

"Em..."

"Get a pair," she said softly. 

"Emily..."

"Put on a pair of panties for me," she said.

I was breathing heavily. "Are...are you sure?"

She nodded. "I can pick if you want."

"No, I...I will," I quickly said, not wanting her to see what was in the box, not wanting her to judge (how foolish).

I picked something on the plain side, not too plain, but not like full on terrify her, either. A pair of white panties with lace and black trim. I brought them back to the bedroom, showed them to her.

"Those are cute," she smiled. I was red-faced. "Is there more?"

"More?" I asked.

"Is it a set?" she asked. "Is there a bra that goes with it."

"I don't think that's a good idea," I said.

"Please," she asked.

"W...why?" I asked.

"Because I want to see," she said, honestly. "Is there?"

I nodded.

"Wear them for me, please," she asked.

I went back to the closet, got out the bra, put them both on. Having just cum, I was soft so by force of habit, I tucked my penis, came back out of the closet and sat on the bed.

I was fairly smooth; even then I kept my body hair shaved, my skin smooth. She might not have noticed when I was a "boy" but obviously seeing me in a bra and panties changed her frame of reference. 

"Well this explains so much," she said.

"I...I'll go change," I said.

She shook her head no. "I think we need to start over," she said.

"Start over?"

"With you making love to me again."

I looked at her, looked between her legs at her soft, wet pussy. "Emily, I...you..." Part of my brain knew this was always fantasy of mine, but having already made love to her, the fantasy was far, off in the distance.

"Shhh, I know, sweetie, I know, but you can do it, I know you can." She spread her legs, touched herself, masturbated herself. "Come do it with me," she said.

So in a bra and panties, I went between her legs, licked her, hesitant at first, then eager, tasted her, tasted myself. She helped me last longer the second time, not too much longer, but enough, enough.

And when we cuddled, she reassured me how good it was the second time.