Teasing - A Short History

Emily was lightly holding my cage, purposefully teasing me, knowing she was making me leak. "Remember when we discovered this?" she asked me.

"This?"

"Teasing," she said.

I shuddered, thinking about her stocking covered feet touching me all those years ago.

It was early in our relationship. Not too early, she knew what I was, but before it became what it is now. Back when I still struggled to be the boy I thought she wanted or at least what I thought I was supposed to be. 

We were on a trip together. I was Sara but not like now. Then I was still mostly boy, with touches of girl, instead of mostly girl, with only touches of boy. So as mostly boy, I was wearing a suit and tie when we went to dinner, but panties underneath. Emily wore some dress that showed off her figure. She was, I don't know, not distant at dinner, but just slightly cold. I felt disappointed as I just wanted to take her back to the hotel and make love, but she seemed not in the mood. She had dressed like she was going to be in the mood but she didn't act like she was in the mood.

But something changed when we got back to our hotel. She said she was going to get ready for bed and came out wearing lingerie; a bra, panties, and garter belt; nude stockings; and heels.

"Oh," I gasped, seeing her. "Oh."

"What?" she asked, feigning innocence.

"I...you look...I mean...whoa," I stammered, feeling myself stir in the panties I wore.

She snickered. "Well that's a reaction," she said. "Being presumptuous, aren't you?"

"Pre...presumptuous?" I asked.

"Presuming things, presuming doing things," she said.

"M...maybe," I said. 

"Presuming what?" she asked.

"I...I don't know," I lied.

"Hmmm," she said again. "I know what you're presuming."

"Do you?" I asked, trying to tease back.

"Of course I do," she said. "You're presuming I'm going to take out you penis, let you put it inside me and do your thing."

"My...my thing?" I asked.

"You know...your thing," she said, coming to the bed, unzipping my zipper, reaching inside, touching me through my panties, feeling me, pulling me out.

"God, Emily," I swallowed, straining.

"Your thing," she continued, "that thirty seconds of pumping, that explosion, that look on your face, that, 'ooops' when that's all there is."

"Emily," I was shaking.

"But maybe that's not what I'm in the mood for," she said.

"What do you mean?" I asked.

She smiled, sat on the bed, took off her heels, put her stocking covered feet on my erection.

"You're always such a tease," she said, "intimating how you're going to make love to me until I cum but teasing me. Maybe I need to tease you."

"T...tease me?"

"You get so excited, love, I've noticed, when I tease you. Maybe instead of letting you do what you want, I should do the opposite." She said this as she moved her feet up and down me, driving me wild.

"The...the opposite?"

"Maybe I should tell you the truth."

"The truth?"

"The truth."

"What...what truth?" I asked, a twinge of fear shooting through me, the ever present insecurity I felt about her at the time, that I couldn't be what she wanted.

But she didn't say what I feared, that she couldn't imagine a life with me, this was part of a game to her, then as now. "Misbehaving little boys in panties don't belong inside a woman," she said.

"Emily," I blurted out, dizzy.

"I told you you like when I tease you," she said, her feet still on my erection. "I think you like teasing more than screwing."

"I...I do not," I said.

"You do, too," she said. 

"Stop," I begged.

"Fine, no more teasing," she said, moving her feet. 

"Emily..."

"Go on then," she taunted me, smiling, "screw me like a man if you'd rather screw than tease."

"Emily," I said, feeling trapped. 

"Difficult to think that way in panties, isn't it?" she asked, touching me again with her incredibly sexy feet.

"S...sometimes," I admitted.

"Screw or tease?" she asked.

"Emily," I moaned.

"It's okay, sweetie, I've already decided, you've been naughty so this isn't going inside me today."

"N...naughty how?" I asked, playing her game regardless of what I wanted.

"Pretending to be a man," she said, foot moving, "pretending you can fuck me, pretending you want to fuck me, pretending you think this belongs inside me, pretending you like it inside me, pretending it makes me cum."

"Fuck, Emily."

"No, my pretty little boy, no. Boys who wear panties don't do that, do they?"

"Emily..."

She moved up next to me, left one foot on my erection, lightly teasing me. "Tell me you agree."

"A...agree?"

"That boys who wear panties don't belong inside a woman."

"Oh god, Emily," I moaned, dizzy as she pushed my mental buttons. 

"I've noticed," she said, "your little penis, most of the time you put it inside me, it's half soft, hardly erect, like you know." She undid my pants, helped me take them and my shirt off.

"Know what?"

"Tell me," she said, "you know, tell me."

"Emily, please," I begged.

"Tell me," she said, "tell me. Tell me why you're never erect like this when I let you put it in me."

I was too far gone to think, to make something up, to lie. "Because..."

"Because?" she encouraged with her voice, with her foot, "tell me."

"Because...because I don't belong inside a woman," I blurted out.

"Why don't you belong inside me?" she asked, whispering in my ear.

"Because...because I can't please you," I said.

"Why can't you please me, love?" she whispered.

"Because...because I'm small," I said.

"And?" I felt her reach down, touch my panties.

"Because...because I'm a sissy," I blurted out.

"And a sissy with a small penis doesn't belong inside a woman. That's why you don't get erect when I let you do that, that's why you're soft when you put it inside me. You know, don't you, that's not where it belongs?"

"Yes, yes," I was shaking as I felt her foot touch me again. 

"But look at it now," she said, looking down, both of us, "look how excited it gets when I tell you it isn't going inside me. See, you'd much rather I tease you than screw you, wouldn't you?"

I nodded. "Y...yes," I whispered.

"Why?"

She looked at me, wanted to hear it, an explanation. I sensed she knew, she got it, but that she needed to hear it. "I...I know I'm not like..."

"Like?"

"Like...like the men you've been with," I said.

"And?"

"And...and I know I can't...I can't do...do what they do with..."

"Your little penis." I groaned, her words like electricity through me. She giggled. "It belongs in panties, not in me, doesn't it?"

"Yes," I said. "And I...I know..."

"Know what?"

"I know I can't do what they do, that I don't belong inside you."

"But you want to?"

I nodded. "But I don't belong," I said, "and...and I..."

"Don't get hard because you know you're trying to do something you shouldn't be doing?"

"It...it's not the same, is it?" I asked.

"What?" she asked back.

"A...feeling a man inside you?"

"No, love, no it isn't. I guess I have a thing for men."

"Like him?"

"Who?"

"E...Evan?"

She smiled. "Yea, like him," she said.

"Why?"

"Why do I like to fuck him?"

"No, no," I looked down, "why...why are you with...with me."

"Oh," she nodded. "Silly, because I love you."

"Why?"

"Because you're my pretty little boy," she said, "and as much as I love men, I love my pretty boy even more."

I was shaking as she ran her foot over me, saw I was leaking, saw the wet spot on her nylon covered foot. Her eyes followed mine, saw what I saw, shook her head. "You're making a mess on my stocking," she said.

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

She looked at me, smiled, shifted on the bed, lifted her foot towards me. "Pretty little boys that make messes need to clean them," she said.

Before, then, and since, I've worshipped her feet, literally. She fed me, her nylon covered toes wet with what I leaked. I knew my actions cemented in her mind, in mine, that I was not and would never be the man in her life, that teasing me rather than screwing me would be the dominant form of our intimacy.

I had a role, a very different role.