Memories - Rewards

It was a Friday, we didn't officially live together until we married, but we'd spend some (though not all) weekends together, usually at Emily's. When I got to her house after work, she met me, sat me down. 

"Are you wearing a bra and panties?" she asked.

I was in a suit; I'd come straight from work. "I...I came straight from work," I said, "I didn't stop home." 

She frowned.

"What?" I asked.

She shrugged. "You disappoint me," she said.

I looked at her. "W...why?" I asked.

"I guess I just hoped, well, you'd wear them without being asked; that you'd wear them because you liked to wear them. I hoped you'd get that I want you to wear them."

"If...if I did?"

She smiled. "Well...boys who wear bras and panties without being asked earn rewards."

"Rewards?" I swallowed.

"Rewards," she said.

I looked down. "I...I wore them," I whispered.

"To work?" she asked, her eyes lit up, her face lit up.

I nodded. "To work," I said.

"Are they things you bought or your stay small, soft, and tucked bra and panties?"

"Does...does it matter?"

"It does," she said, touching my leg. "I suppose I should clarify, pretty boyfriends who wear their stay small, soft, and tucked bra and panties without asking earn rewards."

"What...what kind of rewards?" I asked, eyes fluttering.

She shrugged. "I suppose I should tell you, shouldn't I. But I should warn you, too, if you're not wearing your stay small, soft, and tucked bra and panties, you might be really disappointed."

"I...I know," I said.

"Well, I thought that pretty boyfriends who wore their stay small, soft, and tucked bra and panties without being asked to or told to might...just might...get to untuck their little penis and..."

"And?" I moaned.

"And get to let it grow and..."

"Emily..."

"And get to let it grow and put it inside me like a man would." 

As she said this, the ran her hands over my thighs and I thought I was going to pass out.

"There will be one condition, though."

"C...condition?" I asked, suddenly feeling deflated.

"You need to make me cum," she smiled.

"Emily," I swallowed.

"Shhhh, I know, I know," she said, "the one thing my sweet boyfriend has so much trouble doing with his pretty little penis."

"I...I always try," I said, "but...I can't...you know I can't...promise..."

"I know, love, I know. Such a paradox, isn't it? How badly you want to make me cum like a man does, how ashamed you get when you can't, how badly you want to try just the same, knowing you're too small and too quick."

"Emily," I moaned, incredibly turned on by words that stung yet, said by her, were different.

She reached down, undid my jacket, removed it. "So, are you wearing your stay small, soft, and tucked bra and panties?"

"Y...yes," I said.

She unbuttoned my shirt, saw the bra, smiled. "You're such a good boy," she said.

"I...I just...I just like to make you happy," I said.

She giggled. "And you like to be pretty," she said. 

"And...and I like to be pretty," I agreed.

She pushed me back, reached down, started to remove my pants.

"So pretty," she said. "Who ever thought I'd end up falling in love with such a pretty boy?"

"Emily..."

She looked at the front of my panties, smiled. "Who ever would guess I'd let a feminine, pretty boy with such a small penis inside me."

"Emily, I...I think..."

She touched the front of my panties. "If you want me to take it out, you have to promise," she said.

"I...I'll try but you know...you know I never..."

"Made a girl cum with this? Oh, I know all too well," she said, her words humiliating, thrilling, harsh, tender.

"I...I'll try," I said.

"Promise," she said. "Just say it, if I let you put it in me, say I promise to make you cum."

"I...I don't know if I can," I said.

"You have to promise," she said.

"I...I promise," I said, desperate.

She took off my shirt, was next to me, pulled me on top of her, took me out from my panties. I was swollen instantly. "Put it inside me," she said.

I slipped myself into her wet pussy, shocked how wet she was, shocked how just verbal foreplay turned her on as much as it turned me on.

"Emily," I moaned as her warmth and wetness enveloped me.

"Is...is it in yet?" she asked, knowing from my reaction it was in her, making it obvious from her own reaction she knew it was in her.

"Emily," I moaned again, pumping once, twice, a third time. "I...I'm going to...I need to..." I wanted to slow down, thinking if I could just go slow, just make it last, I could have some hope of making her cum.

"Make me cum," she said, sensing I was slowing, "don't you dare stop, make me cum, put your little penis inside me and make me cum like a man would."

It was too much; she knew it and I knew it, knew she wanted me to fail, wanted me to explode inside her without doing what I promised. I wanted to stop, wanted to last, wanted to but couldn't and instead closed my eyes and just let the inevitable happen.

I felt ashamed, even as she kissed me, started to get off her. "What are you doing?" she asked as she pulled me to her breasts.

"I...I"m sorry," I said, "I...I tried."

"You promised," she said.

"I...I tried," I said.

"You're not done," she said, "you promised."

"I...you know I can't...I mean..." It would take hours, even days, before I could do that again.

"You promised," she said, "you promised to make me cum. Love, I never expected you to do it with your little penis."

"But...but I..." I stammered, knowing now what she meant.

"A promise is a promise," she said, reaching down between her legs, touching herself. "Now make me cum with that pretty mouth of yours."

"You...you're messy," I said, torn, part of me repulsed, part of me thrilled.

"I'm sure you'll take care of that mess while you're making me cum. Men don't worry about that, but pretty little boys should always clean their messes."

"Al...always?"

"Always, love, always. Cleaning up messes like this is just what girls do. Trust me, I've licked and swallowed my fair share of cum; this is what we do."

"But you're a girl," I said, knowing what her response would be.

"And so are you," she touched me, gently, pushed me down. "So be a good girl and do what we do."

"I...I'll try," I said.

"Oh, you'll do more than try," she said, "you will...now and always...you will. That's your reward, that's your true reward."

After, after I'd fulfilled my promise and made her cum...and cum...and cum, she looked at me, smiled. "You know, love, I think you like that more than you're letting on."

"Making you cum?" I asked.

"Cleaning up your mess while making me cum," she said.