My Summer of Sissification

"I know," I said.

"You're getting harder. Is it because a real man is fucking a woman you love or something else?"

"I don't know."

"Well tonight we want you to go all the way while we watch."

"What do you mean?"

"We want to see you taken by a real man. Zooey is just warming Fred up right now. Come on. Come to my room," Liz said.

She took my hand and led me into her bedroom.

"Get up on the bed, on the edge, on your hands and knees, so your bottom is facing me."

I knew what was happening. I complied. I was under Liz and Zooey's spell. I would have done anything they asked.

"That's a good girl. Because it's your first time it's probably going to hurt a lot but that's normal. All girls go through this first hurt, you might even bleed a little but you'll be okay. You can't be a woman unless you learn to deal with the pain men cause."

I heard the door open. Zooey and Fred had come in.

"She's almost ready. She just needs some lubricant on her small opening," Liz said.

My panties were pulled down. Two fingers greased my anus poking in and out a few times. I clenched my butt.

"Relax Nicole."

I felt Fred's penis begin to push. It hurt. Then it hurt a lot. More hurt until he seemed to push through a final resistance. The pain diminished. He went in and out. Zooey had her hand in her panties diddling herself as she watched. Liz stood grinning and watching him penetrate me. Eventually Fred grunted and stopped, his full length inside me. I knew he was ejaculating his semen in my bottom.

That was the last night I spent with Zooey and Liz. I called Zooey a hundred times and she never answered. The summer was over. We had no closure. I spoke briefly with Liz who told me it was over. She said thank you it's time to move on.

Years later, one night, I presented my wife with a pair of white lace panties I'd bought for her while she was out of town.

She held them in front of her face while sitting up in bed and turned them back to front saying how pretty.

"Stand up and put them on," she said.

Her request came out of nowhere. I stood up and squeezed into them. She reached over and stroked me through the silkiness until I was hard.

"You like how that feels don't you?"

"Yes," I said. I trembled.

She laughed. "That's enough. Take them off. I don't really like that. You're my man."

I think about Zooey and Liz from time to time. I broke through some kind of barrier I didn't know existed. It wasn't the feeling of silk or the lipstick but letting go of some enormous obligation tied to what it meant to be a man.

My wife never asked me to wear panties again and dismissed a suggestion once when we were both a little tipsy that she gloss my lips with her favorite colored lipstick.

I haven't ever told her about Zooey and Liz and that summer.