u/According-Teacher-38

Checking the Boxes Pt 6 [MF]

Jess and I woke up slowly the next morning. We were still naked, tangled up in my quilt on one side of the bed, the evidence of our activities the prior evening on prominent display on my fitted sheets beside us. Neither of us had spoken yet, but I had felt her stirring and knew she was at least partially awake, as she lay on her back beside me, mostly exposed.

I slipped out of bed and into the master bathroom to rinse off. By the time I returned, she had thrown the covers fully off of herself, and the sunlight streaming through my blinds cast bars of shadow across her petite frame. I placed a hand on the bed on either side of her hips and slowly lowered myself until my mouth was hovering over her bare pussy. I touched my tongue to her lips, almost imperceptibly, and dragged it across them. She didn't move.

I pressed my tongue more firmly, parting her folds, and she started a little, her head rolling on the pillow, but her thighs adjusted on the bed into a butterfly pose, granting me full access to her most intimate parts. I gently teased her clit with my tongue, and saw a faint smile cross her face. Then I began working her over in earnest.

My tongue rhythmically lapped at her sex, the tip tracing the space between, through her moist folds, and flicking across the nub of her pleasure, before beginning the descent back to the journey's origin. Her hand slid to the back of my head, fingers combing through my hair tenderly, encouraging me on. With each passing minute, her pleasure became more apparent in the way she sighed, and the heaviness of her breathing, but I kept my pace steady, in no hurry to bring her to climax.

She applied gentle pressure to the back of my head, forcing my mouth into her pussy, and I changed tact. I drew her clit between my lips with gentle suction, running my tongue over it in methodical passes, and she clenched at the sheets with the hand that wasn't intertwined in my hair. I knew she was getting close.

I stopped all suction and movement of my tongue, but kept my mouth attached to her pussy. The tension slowly drained from her hips, and I resumed my affection on her clit. Her hips arched into my face, her hand clawing at the sheet, and I stopped again. She groaned, tightening her grip on my hair. I resumed sucking, and her hips arched again. She pressed hard on the back of my head, and I decided I had teased her enough. I sucked hard at the same time my fingertips found her nipples, twisting firmly but not to the point if pain. She careened over the edge with a deep moan.

Her hips rose and fell, humping my face as waves of pleasure rolled through her body, and I kept my stimulation consistent as she rode out her orgasm. With a final, sustained thrust, her final wave subsided and her hips dropped with finality while her breasts continued to rise and fall rapidly as she came down from her climax.

I stood, pulling her ass to the edge of the bed, her eyes remaining closed as I positioned her. I lowered myself on top of her, my rock hard cock inching towards her wet pussy, my lips landing lightly on hers at the same time my cock head dipped between her pussy lips. She met my kiss tenderly, opening her mouth to accept my tongue as it probed her, hooking to trail the backs of her teeth. She sucked on my tongue as my dick sank fully inside of her in one smooth stroke.

Her arms wrapped around my neck, drawing me tighter against her, her hand guiding my head to enforce the deep kiss she was lavishing on me. I pumped into her steadily, her warmth and wetness feeling like home to my aching cock. Eating her out had made brought my desire to a fever pitch, and I knew I wouldn't last long with how intimately she was kissing me.

Her hand trailed down my back, grabbing as much of my ass as she could reach and driving me harder inside of her. Her legs wrapped around my thighs, locking me in place, and I picked up the pace of my thrusting. Her kiss was relentless, making me feel lightheaded, and I felt the pressure building in my prostate.

My climax hit me all at once, and with a few panicked thrusts, I erupted inside of Jess. I felt her kiss give way to a smile, and her fingers dug deeper into my ass cheek, driving me as deep inside of her as I could go, the cum pumping out of me with every thrust. ​

When I had spent my last, I pulled out of her, coming to rest beside her as she turned her head towards me and finally opened her eyes.

"Well, I guess you can check 'Wake up to sex' off your list", I told her with a satisfied grin.

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u/According-Teacher-38 — 15 days ago

I lay in a stupor, my own cum drying on my skin, the weight of Jess still pressing me into the mattress.

"I'm serious, I can barely fucking take it", she breathed into my back. There was a need in her voice that surprised me. I began to rise from the bed and she rolled off of me, moving to her knees on the mattress beside me. I looked into her eyes and they were positively dancing with desire.

"If you can get me hard, you can use me anyway you want", I told her.

Challenge accepted.

Her head dropped immediately to my cock, still coated in lube, and she swallowed me whole. The sensation of my soft dick in her mouth was so novel, and her enthusiasm so infectious, I lowered my head to the pillow beneath me and let her work. Within a minute, I felt the blood returning to my dick. I was so drained, I didn't know how I would possibly cum again tonight, but in this moment, that didn't matter. Jess was desperate, and I wanted to satisfy her.

Jess lifted her head from my stiff cock and spun on the bed, presenting her bare ass to me. She dropped into a deep doggy position, and I took the invitation, rising to my knees and lining up behind her. Just as my cock head teased her entrance, she said "No. Not there".

I sat, confused, my hands resting on her ass.

"I want to try... The other way". The answer winked up at me from between her plump cheeks, and my confidence faltered a bit.

"Jess, I want to please you, but I have never..." My voice trailed off, and she interjected quickly: "Neither have I, but the way you work back there, I've never wanted anything more in my entire life."

I chuckled at her hyperbole, running through scenarios in my head until I finally settled on a response.

"We will go slow, and stop the moment you say. Are you sure?"

"If I don't feel your dick in my ass in the next 30 seconds, I'm never going to speak to you again", she quipped.

I spanked her for her snark, and she yelped and then cooed in response. Leaning over to the nightstand, I grabbed the bottle of lube and began applying it liberally to her puckered hole.

"Relax", I instructed her. She obeyed. Her sphincter softened against my touch, and I continued to massage it, gently loosening her until I could slide my finger inside. Over the course of the next several minutes, I worked my finger fully inside her ass, then replaced it with my thumb. When I finally removed my thumb, Jess groaned, and her hole winked up at me, clearly agape from the the occupancy it had experienced.

I placed my dick head against her sphincter, gently pressing. More lube. Pressing again. Jess relaxed more, and I felt the tip dip into her hole, only to be pushed back out when she next contracted. Jess reached around, grabbing my shaft, guiding me in. As she relaxed again, she pulled my tip deeper inside of her. This time, the contraction gripped my head like a vice, and she repeated the process - relaxing, pulling me deeper, contracting. Her face was screwed up in concentration, her jaw hanging slack and eyes clenched tight.

With a palpable release, the head of my cock disappeared fully inside her ass, and she let out a guttural moan into my pillow. I stared in disbelief at my shaft, disappearing into her ass, her hole clenched tightly about a third of the way up my shaft. I pressed deeper, and Jess recoiled, so I froze.

"Shit, give me a sec" she said, and I gently rubbed her lower back while she sat still, clenching and unclenching around my shaft. She pressed her hips backwards, and another inch of me disappeared inside of her. She felt impossibly tight around the entrance, but surprisingly looser deeper inside, where my cock head had taken up residence.

She pressed back harder, groaning into my pillow as she took the rest of me inside of her, my balls coming to rest against the lips of her pussy.

"You feel unbelievably large"

She said it so matter off factly, I couldn't help but laugh, which got her laughing too. Her ass clenched so hard around me it was painful, and we both stopped laughing, replacing the sound with whispered profanity. I waited for Jess to make her next move, and after a minute, she raised up on her elbows.

"Go slow. Fuck my ass"

I eased out of Jess, inch by inch, until only the tip remained, then began pressing back inside of her. She whimpered at my re-entrance, and I didn't stop until I was fully inside of her again.

"I can't fucking take it. It feels so much better than I expected."

I couldn't necessarily agree with her - her pussy felt tighter, and better overall - but the ecstasy she was experiencing at this new sensation was turning me on to no end.

I continued to slowly ​​​​​​​​​​slide my cock in and out of her ass, and she matched movements, pushing her hips back against me. The noises coming out of her were a cross between supreme pleasure and mild pain, but her entire back was flushed with desire and her fingers now worked her clit as I kept a steady rhythm. Suddenly, I felt her clench impossibly tight, just before releasing in a string of unintelligible cursing. She rocked back into me, and I picked up my pace a little as she erupted in waves of pleasure.

As I felt her start to come down, I was about to offer to pull out when she suddenly picked up the pace with her fingers again.

"Oh my go-- what the hell??" there was surprise in her voice as we both realized: she was about to cum again. I was halfway inside her when she cried out, another orgasm tearing through her body, laughter lacing her cries of pleasure. I pumped through it again, feeling my own climax beginning to stir. She lowered herself to the mattress, one hand trapped between her body and the bed, fingers still playing on her clit. She muttered a muffled word into the pillow.

"What?", I said, going still in case she wanted me to stop

"​​Harder"

She was breathless and spent, but still had a look of pure bliss on her face. I pulled my shaft mostly out of her, and began pumping just the last two inches of my cock inside her ass in quick thrusts, now in prone bone. The tight squeeze on my frenulum was pushing me quickly towards another orgasm of my own, but Jess beat me to it.

"Right there. Don't fucking stop. Harder."

Her hand was a blur now, fingers assaulting her clit with a ferocity I'd never witnessed. Her head was turned out, face on the pillow, drool pooling beneath her open mouth as tremors racked her body and she moaned my name. The sound of my name, said with such abandon, sent me over the edge.

My cum erupted inside of her ass, and I pressed myself deeper, pumping hard as she continued to cry out through her own pleasure. At last, when I was fully spent and beginning to soften, I pulled out of her hole with a squelch, my cum dribbling down the inside of her cheeks.

"Take a photo"

Her hand floundered on my bed, trying to find where she had tossed her phone before our shower, and finally handing it to me. I took a picture, ​​my cum pooling in her ass and running onto the sheets, and showed her. She gave a contented smile and said "That's going in my spank bank".

I got a towel and rinsed one end in warm water before beginning to clean her up. She winced as I gently passed the towel over her ass hole.

"I had no idea how fucking magical that would be. I don't know what you were hitting in there, but I have never cum like that before. I'm normally one and done, but whatever was going on kept me right on the edge. I could've kept going. I could go again right now"

I finished cleaning her up and rolled her onto her back, spreading her legs and situating myself between them. She smiled, knowing what was coming, as I lowered my mouth to her pussy and began gently sucking on her clit. Within a couple of minutes, she was riding another orgasm, and finally coming down for good.

I crawled up beside her and pulled her to the clean side of the bed, drawing a quilt up over us both. She was asleep inside of 5 minutes, her gentle snores signaling a job well done.

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u/According-Teacher-38 — 19 days ago

Jess's eyes looked hazy, and I could see the wheels turning in real-time.

"Did you just fuck me unconscious?"

She asked the question with zero irony, and I was trying not to laugh at how bizarre the situation was.

"I think you over-heated. I forgot to turn the vent on, I'm so sorry"

We were both naked and dripping onto the comforter on my bed. Jess looked unharmed, but still a little confused.

"What do you remember?", I asked her.

"I felt my orgasm building and remember thinking 'I can't breathe', then I was in your bed. Did you date rape me?!"

I was relieved to see her sense of humor returning, albeit dark.

"Given the way you were begging for my cock, I don't think a roofie was necessary", I shot back, and at last she smiled.

"Oh. Necrophilia really does it for you, I see".

Her eyes had dropped to my dick, where my Cialis-enhanced erection stood tall and relatively impressive​ (for extremely average white guy dick). I felt horrible for still being hard while I was unsure of her wellness, but there was really only one way to get it to deflate right now, and being in bed with a stunning, naked woman was not one of them.

"I always told you, you are drop-dead gorgeous"

She cringed at my miserable pun, but reached for me anyways. I caught her by the wrist and said "Jess, you need to rest. You just passed out. Lay back, I'll get you some water".

"I want to eat your ass".

I stared blankly at her, processing what she had just said. I saw no trace of humor on her face.

"I thought I saved you from hitting your head, but maybe not", I ribbed her. Her hand broke free from my grip and wrapped around my cock, and she just held it, maintaining eye contact. It occurred to me that she was serious, and my mouth went dry. My cock twitched involuntarily, and she noticed.

"Look, you can say whatever you want, but you won't convince me you aren't into it - not with that lightning rod jumping at the idea."

"Fuck, Jess - you don't need t-". She squeezed my cock, cutting off my sentence as I moaned.

"Get on your knees. Head down, ass up", she instructed me. My head was spinning. Was this really happening? Almost against my better judgment, I obeyed her. I buried my face in my pillow to hide my embarrassment. I heard my nightstand drawer slide open, and looked over in time to see her ​withdraw my pocket pussy and a bottle of lube.

"Try to relax. You're safe, I promise."

Her words took the edge off my nerves, and I closed my eyes as I heard the cap of the lube click open. The next thing I felt was the pocket pussy sliding onto my cock, and the mattress sinking behind me as Jess climbed onto the bed. She began slowly stroking me with the Tenga.

The suspense was killing me, but I couldn't bring myself to look back. Warmth suddenly enveloped my left testacle as she sucked it into her mouth. Her tongue lapped at my sack, and she latched onto the other one for a moment, while still stroking my cock. She placed a hand on my ass cheek, raising my hips higher and spreading my cheeks apart. I felt gentle puffs of air and sensed her face hovering, then felt her tongue at the base of my sack, broad and wet, and trailing ever so slowly from front to back. It entered my crack, then withdrew.

Another slow stroke, from sack to crack, penetrating deeper this time. Over and over, she licked me, still sliding the Tenga up my shaft and over my head in a tantalizing, slow rhythm.

Without warning, her tongue went straight to my sphincter and I gasped hard. She pulled my ​cheeks farther apart, and her tongue delved deeper. I swear to god, I saw stars. She made her tongue more pointed and probed my hole, flicking it up and down. She bit the inside of my ass cheek, and I whimpered like a lost puppy. The sensations tearing through my body were obscene and so wrong - but oh, so right.

She began flicking her tongue against my hole in rapid succession, and I knew it was the beginning of the end. She seemed to sense it too, as she began stroking me faster, digging her nails into my cheek. I had been reduced beyond coherent speech, and just let out moans of pleasure as she stroked me at full speed and I careened off the cliff.

My ass clenched hard as I thrust into her hand, spraying cum across my pillow and comforter. She replaced her tongue with her thumb, applying steady pressure to my sphincter as I continued to cry out, my orgasm building in intensity and seed continuing to shoot onto the bed below me. Finally, the waves of pleasure receded, and I collapsed into the mess of my own making.

I tried to steady my breathing, as I felt Jess slide her naked body on top of mine, her nipples trailing up my back, her head coming to rest between my shoulder blades. The weight of her body on mine worked in centering me.

After what could have been 5 minutes or 3 hours, she shifted higher​​​, her breath falling on my ear as she whispered:

"That was one of the hottest things I've ever seen. I'm going to need you to get hard again - I'm fucking soaked". ​

​​​

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u/According-Teacher-38 — 29 days ago