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 darkness. I turned back toward her, and felt her turn over, turning her back to me, but not coldly, because her butt then pressed up against my crotch. I put an arm over her and she held it, and I pushed my pelvis into her, my cock pressing against an ass cheek.
We lay like this for a few minutes, until she shifted her position slightly, her hips moved subtly, and her butt rubbed back against my dick. Once, twice, three times.
Okay maybe she wasn't just changing position.
I started moving my hips in return and lightly ground my crotch against her, and moved my arm so that my hand cupped a breast. The cotton of the pajamas was doing almost nothing to disguise the feel of her body underneath, the weight of the boob, the softness of the flesh.
Margaret reached behind her with a hand and dug around my hips for the waistband of my sweats. Then her hand was under the hem and inside, brushing over my inner thighs, and I felt it find my cock and grab it. She started tugging on it, and desire surged through me. I put my hand down the front of her shirt and grabbed her naked breast, and moved my chin over her shoulder, breathing in her ear. Her body started to writhe against mine, her hand continuing to play with my dick while I massaged and held her tit, lightly pulling on her nipple. Our breathing was heavy, but otherwise we were soundless, lusting for each other in the dark.
She turned her head and our lips found each other and we started making out, our breath fresh with mint. I took my hand off her breast and out of her shirt and reached for the front of her pajama pants. I undid the string at the front and then shoved my hand under the elastic and put my hand on her pussy. She lifted her upper leg slightly to give me better access, and when I first touched her labia her kissing grew more feverish, her hand tugging harder on my cock.
I starting rubbing at her clit, feeling the warmth of her, her wetness growing. I was running my finger around it in small circles, and at one point she broke off kissing me to say "oh shit" before leaning back to me and kissing me again. Her free arm bent up and gripped the back of my head, pushing our faces together. I put my tongue in her mouth and she reciprocated, and we explored each other's mouths as we continued masturbating each other.
I moved my finger lower, rubbed around her hole for a second, and then inserted it. She moaned into my mouth then turned her head away and rested it on her pillow, panting softly, her hand jerking at my penis. I hooked my finger and tried getting at her g-spot, but the angle was almost impossible on my wrist. I moved my weight, her hand came off my penis, and I climbed on top of her.
Light from the apartment building next door shone around the very edges of my curtains, so I could see the faintest outline of Margaret below me in the dark, her hair tousled darkly around her head. I pulled the pajama pants off of her, the marble color of her legs almost glowing in the dark, and then knelt by her side and put my finger back in her wet pussy. She reached up and felt my hard cock through my sweats and fondled at it, and I leaned down and kissed her, hooking my finger again and now getting a great angle on her g-spot. I started flexing my finger and her breathing grew shallow.
"Your dick," she said, between labored breaths. "I want your dick."
