Jack's Adventures 02: Margaret 02 - Sex Stories

Jack's Adventures 02: Margaret 02

I keep a spare set of women's pajamas around, a cute red plaid deal from Target, just in case I have a woman who wants to stay over, or who doesn't want to immediately get back into her work clothes after we've fucked.

Like tonight, with Margaret.

I dug them out of a closet and she put them on gratefully. I tried to watch her dress without being too obvious, wanting one last look at her slender legs, her flat belly, her pillowy tits. When she'd finished buttoning the top, she clasped her hands behind her back and did a quick pirouette, smiling goofily, showing off the fit. I applauded; her, but also my choice of pajamas. They fit Margaret's slim 5'6" frame almost perfectly, the cotton draping provocatively over her perky tits and ass.

"I'm going to go put on sweats," I said.

"No," she said. "You have to stay naked."

I looked at her with mild surprise. She was trying not to smile, but failing.

I walked up close to her, feigning sternness. My face was an inch from hers, and she bit her lower lip.

"Just kidding," she said softly, her doe eyes looking up into mine.

I reached up and lightly cupped her jaw.

"Are you telling me what to do?"

She shook her head, her eyes wide.

"That's a shame," I said.

I let her go. She smiled.

When I was also in sweats, we hung out in my living room, finishing our drinks. My old fashioned was watery by now, but still tolerable. Margaret lounged across the couch, drinking her wine, her legs off one edge, her ...

... torso leaning into the crook of my shoulder. We were incredibly comfortable around each other, and we talked casually, enjoying the late night mood, something by Bill Evans coming softly off my record player.

At a certain point, our drinks finished, we sat quietly. My arm was around her, a finger drawing slow circles on her shoulder. I couldn't see her face, and she hadn't said anything in a long time. I wondered if she was falling asleep. But she wasn't, because then she said:

"Can I stay here tonight?"

She craned her neck to look up at me. She looked so nervous about it, it was very cute.

"Please do," I said.

She smiled and put her head back on my shoulder, one of her hands going to rest on my thigh.

Soon after, we washed up. We stood in front of my bathroom mirror, brushing our teeth (a spare toothbrush also always on hand). Margaret's arm motion was making her tits jiggle, and I stared at them moving beneath the fabric of the pajamas. I then looked up and saw her watching me, smiling, her mouth foaming white.

We moved to my bedroom. She looked at my fluffy comforter, at all the pillows piled up, and ran and jumped onto it.

"Best bed ever," she said, collapsing onto her back.

"Glad you like it," I said, removing my shirt and getting under the covers.

She quickly got under them as well and we faced each other, our bodies close, our knees touching.

"Lights out?" I said.

She nodded.

I reached back, turned my lamp off, and we were shrouded in ...