Memories - Questions

We'd had a romantic dinner, dressed up, home cooked, me serving Emily. Five courses, each one paired with a different wine, each planned by me and cooked by me and served by me. Light. Airy. Delicate. In the kitchen and in the dining room, I served, so I was in charge. Emily just sat there, smiled, enjoyed.

We were in her bedroom, in her bed, where the roles were reversed. She was once again in charge, she led, she was in control of the situation, she picked, she decided.

"Dinner was amazing," she said touching my leg, letting her hand slide over my nylons, "you're so good to me."

"I...I wanted to do something special for you," I said.

"It's always special when you cook for me," she said, "like you're auditioning for me."

"Auditioning?"

"Like there's a role to be played, a role to be filled, like you're showing me this is how things could be."

"I just...I mean...I don't have to..."

"It suits you," she said, "you're good at it."

She moved her hands down my calf, found the strap of my heel, unbuckled, pulled my foot out of the shoe, smiled. "So good...so pretty," she said. "What else are you good at?"

I showed her for the next hour, touched her, kissed her, made love to her, staying soft and tucked, my hose protecting everything. I found the dildo I'd bought her recently, used it to tease her, to play with her, to substitute for what I couldn't do. Licking her while I teased her with it, rubbing her with it, pushing it into her, slowly, gently, teasing. 

When it was wet, soaked, I felt my tongue on my lips, licking. I slid it over her, past my lips, let my tongue flick it, tasting her on it, just barely, pushing it into her again.

The teasing got to be too much and she reached for it, grabbed it, took control of the depth and speed of the penetration, her head back, moaning as she fucked and I licked.

Every time she pulled it out, I felt my tongue on it. Every time she used it to tease her clit, I opened my mouth, let my lips touch it, kiss it. Each time I felt more of it pass my lips, tasted more of her on it until we were sharing it. I wasn't just licking her, I was licking it, too, sucking on her, sucking on the cock shaped dildo, her taste on my lips.

I was being careful at first, subtle, but I lost control, sucking her juices of the head of the cock, off the shaft just as much as I was sucking her.

I'd lost track of how often she'd cum, how long she'd shaken, when it was she pushed me over, kissed my nylon covered legs, worked her way up my thighs, blew gently on me. "Oh my god, Emily," I moaned as her mouth hovered over me, in my mind screaming at her to release me, untuck me, touch me.

"That wasn't the first time, was it?" she asked.

"First time?"

"You were too good for the first time, too comfortable, to eager."

"I love licking you," I said.

"I don't mean me, love, I mean sucking cock."

"What?" I gasped, my blood running cold. Did she...did she ask...

She kissed her way up my stomach, over my chest, nuzzled my neck. I felt her body pressing against me, her nylons rubbing against mine, her pussy rubbing against my tucked, leaking mess.

"When?" she whispered in my ear, "who was he?"

"W...who?"

"The first time you sucked cock, when? Who?"

"Emily, I...I never..."

"When, love? Don't lie, it came to easy to you. When?"

"Emily..." I couldn't...I couldn't...

"How old were you?" she asked.

"Emily..."

"How old?" I felt her rubbing against me, felt my body leaking, knew it was on me, on her.

"Emily..."

"How old were you when you sucked cock for the first time?"

"Twenty...twenty-two," I heard myself say.

"He was older?" Her voice was soft, gentle, absent any accusation.

"I...I don't..."

"I just assume he was older, my pretty sissy under the spell of an older man."

"Emily..."

"How old?" she asked.

"Older," I said, "f...forties...early forties."

She kissed me hard and deep on the lips, her tongue sliding against mine, her mouth hungry. "Did you dress for him? Were you feminine for him?"

"Yes," I said, "I...I never...he never..."

"Never met you as a boy?" she asked.

"No," I said. "Emily, you have to understand, I was...confused."

"Was it just the one time?" she asked, kissing me deeply.

"I don't know," I said foolishly.

"You know," she said, "a girl knows if her first blowjob was a one-time thing or not. She knows if it was just too many drinks, too overcome...or something else."

"It...it wasn't," I said. "It wasn't just the one time."

"How many times?" she asked, of course she asked.

"That I don't know," I said.

She looked at me again. "A girl doesn't know how many times because she lost count," she said.

"Emily, I can't..."

"A girl loses count because she's in a relationship," she said.

"It wasn't a relationship," I said, "it was..."

"A what?"

"Like...like a thing," I said.

"A thing? Or you mean a fling?" she asked. "A young sissy and an older man kind of fling?"

"It was like a...a summer thing," I said.

"Don't defend yourself," she said.

"I...I'm not...I just..."

"A thing or a fling?" she asked.

"A...a fling," I said.

"He was the one in charge, I assume?" she asked.

I blushed. "I...I guess," I said.

"You guess? I assume with a young sissy and an older man things we're not...reciprocal. I assume there was a top...and a bottom? And I assume this man that never met you as a boy was the top?"

I nodded.

"Do you miss it?"

"I don't know if miss is the right word," I said, "I..."

"I assume there was a fantasy going through you mind a earlier when you were...attending to me."

"Yes," I said.

"He was fucking me?"

"Yes," I said.

"And when you pulled the cock from my pussy, when you looked at it covered with my pussy juices, you were overcome."

"I...I wanted to..."

"To suck cock," she said.

"Yes," I whispered.

"Have you ever done that since?"

"No," I said.

"You would, wouldn't you? Do it again?"

"Yes," I said.

"Mine?"

"Yours?" I asked her.

"My cock," she said.

"Your...your cock?"

"My cock," she said, reaching for her dildo, bringing it between her legs. "I want to see you do it again with my cock."

"Emily..."

"Show me, love, show me how good you are at it."