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 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."

I shimmied my sweats down my thighs, my cock springing up and out, and I brought it close to her face. She grabbed it with her hands and put her mouth on it hungrily and we were suddenly recreating our position from earlier in the night. Her mouth felt clean and wet, my cock throbbing thick. I attacked her g-spot, and she sucked harder on my dick, her lips stretched around it, working my shaft with both her hands. I ran my free hand through her thick hair, gathering it behind her head, not forcing her onto my cock but not opposed to her going deeper. And she picked up the signal and tried, opening her lips around it and pushing it slightly further into her throat. Right at that moment I sped up with my finger, and she pulled my dick out of her mouth and gasped.

"Please fuck me," she said.

I got on top of her while she unbuttoned her top. I lined up my cock with her pussy, and then the top was open and I saw her beautiful breasts outlined in the dark and my cock swelled further, and I drove it into her. She gasped and wrapped her long slender limbs around me, her legs around my back, her arms around my shoulders, her soft nubile body pressing up against me, and the innocent sex of earlier was long behind us, and I started fucking her senseless.

I pounded her quickly and methodically, feeling her breasts pressing up against my chest, her breath in my ear. Her pussy was wet and tight, and I focused on stimulating her clit with the top of my cock at a constant unceasing rhythm. The breath went out of her with every thrust, and came back to her in ragged inhales. My headboard bounced against the wall, our bodies grew sweaty.

"Oh, Jack," she breathed hoarsely into my ear.

The sensation sent goosebumps up my skin and I kept fucking her, savoring every sensation of having my dick inside this young goddess. A few more minutes of this followed, a few more minutes of my cock driving into her pussy at constant tempo, and she breathed again:

"I'm gonna come, Jack. I'm gonna come."

And she did, she let out a sharp intake of breath and orgasmed, her limbs still wrapped around me, holding me tighter, her body shaking. I fucked her straight through the orgasm, until her muscles relaxed and she let go of me and lay flat on the mattress, staring up at me, her pajama top still down around her arms, her breasts heaving. My eyes had adjusted by now and I could see more of her face, the width of her eyes.

"Did you come?" she asked.

"No," I said.

"Get on your back."

I cocked my head.

"Are you telling me what to do?" I asked.

She smiled. "Yeah."

I laughed and got on my back, and she climbed on top of me, facing me. She guided my cock into her pussy, still soaking wet, and then sat back, the pajama top hanging open around her breasts. She gathered up her hair and raised her arms and crossed them over her head, this motion lifting her breasts up, and then she started to ride me slowly, sensually.

She looked magnificent, her long pale torso curving up from my cock, the curve of her breasts, her arms entangled in the dark mass of her hair above her head.

"You're so gorgeous," I whispered.

I saw her smile in the dark, and she kept going, her pussy sliding on and off my cock. Sensation was growing at the base of my dick.

"You like my body?" she said.

"I love it."

She took her arms off her head, her hair cascading down her shoulders, and she crossed them beneath her breasts, pushing them up and together. My dick was tensing up.

"You like my breasts?" she said.

"I love them."

She started bouncing slightly faster on my dick. My orgasm was moments away. And then she laid the hammer down.

"You like that I'm your little bartender? Your little secret? That you're the only one who gets to fuck me? That you're the only one who gets to see my tight body? My breasts? That you're the only cock I'll suck. The only one I'll fuck. The only one who will make me-"

And I interrupted her by coming, hard, my body jerking as my cock unloaded inside of her, the pleasure magnified a thousandfold by what she'd been saying.

"Fuck!" I yelled, her pussy still moving up and down on my dick, milking me dry.

When I was sure I was empty, of everything that had ever been in me and would ever be in me, I put my head back on the pillow and laughed. She started laughing too, covering her mouth with a hand, and she leaned down next to me, giggling uncontrollably.

"How was that?" she asked.

"Fucking incredible," I said.

"Oh good! I've never done that before."

"Fooled me."

She nipped at my shoulder, then jumped off of me and ran to the bathroom. When she came back, I was still lying in the same spot, and she collapsed next to me. We lay there for a while, staring at the ceiling in the dark.

"I'll never forget you, Margaret," I said.

"Ditto," she said.

We stayed there for a while, I don't know how long. Eventually we both fell asleep. The night grew still around us, quiet except for our breathing, dark except for the light behind the curtains.