tagAnalA Date to Remember

A Date to Remember


It's a warm Friday morning, a dozen or so hours before our planned date night. We've both been so busy that the week has sped by, a whirlwind of social commitments and late evenings at our respective offices. The time we have managed to spend together has consisted entirely of falling asleep on the couch while trying to make it through an hour-long TV show. The mornings have been rushed, both of us having to get up and moving, with no time for lounging or the special type of pre-dawn intimacy we've developed over the course of our relationship.

I love those mornings; waking up to the feeling of you climbing back into bed, freshly showered and dressed. Dozing off while inhaling the smell of your soap, resting a hand on your neck and scratching my fingers gently through your hair, while you stroke my hands, my arms, my stomach and I feel you breathing gently on my neck. The most perfect mornings are those where we have time for you to wake me slowly, easing into the day with shared laughter over our private jokes.

The gentle laughter and familiar touches are comforting, and at times, arousing. The sensations remind me of other mornings, where your hand rubbing my stomach has dipped low and your fingers have traced over my panties, causing my breath to falter and my hips to reflexively lift. I think of the mornings where strenuous workouts have left my muscles stiff and aching, and you've taken the time to massage me. Of course, I know you don't mind using your hands to help me recover from my workouts. I suspect that it's become a tacit flirtation for me to roll to my stomach and for you to knead the backs of my thighs up to the crease of my ass peeking out from the hem of my boyshort underwear. It's such a delightful tease for me, feeling the relief in my sore muscles and wondering when you'll move upward and grip my ass in your hands.

It's inevitable that you'll spend as much time as you can touching my ass, since it's your favorite part of me. Over the years, you've explored it so thoroughly, I expect you know it better than I do. The moment I feel your fingers move above my thighs, I am reminded of all the ways you've enjoyed my ass, and warmth rushes through my body. I want to shift my position, parting my thighs and giving you access to my pussy, but our position prevents it. With me lying on my stomach and you straddling me with your hips over the backs of my knees, my legs are pinned. I moan and whimper, enjoying the massage and feeling excitement mount inside me.

Not knowing what you'll do next thrills me. I can't comfortably turn to see you, so I can't anticipate your touches. Will you gently run your index finger from my lower back down the cleft of my ass to my swollen pussy? Will you spank me, causing me to yelp with excitement? Will you suddenly yank down my panties and begin kissing and nibbling your way over my bare cheeks? Or will this be a day where practical matters, like traffic and work commitments mean that the massage is the culmination of our morning time together?

I want to know, want to beg you to touch me more, but in these moments, I find submitting to your desires more exciting. I writhe under you, trying to feel if your cock has become hard, but the position is wrong. I wonder if you're remembering other times that have begun like this, or if you're fantasizing about something new. Perhaps you're thinking of something else entirely, something mundane, though given the enthusiasm in your fingertips, I doubt it.

This morning didn't begin with any such stimulation, though I had woken from a dream while you were showering with my nipples stiff and my panties damp. I slid my hand into them, pausing briefly to stroke my painfully swollen clit before parting my lips and slipping a finger inside. I was surprised to feel how hot and wet my pussy was, and I was so tempted to strip bare and let you find me atop the covers, frantically fingering myself. I've often fantasized about you catching me like that, and tried to imagine how you would react.

This was not the day for that type of behavior, and I redirected my energy elsewhere. We both needed to be up, dressed and out of the house for work commitments, so when you came to wake me, I was already alert and had been mentally listing items from my to do list while checking my emails. A few minutes for hugging, kissing, and confirming plans for tonight, and you were out the door.

The rest of the morning flew by, a haze of meetings, emails, projects, and distractions. I left the office as planned and went home to shower and get ready for tonight. I don't ordinarily make this much effort, but after a long week and not much time alone, I wanted to look my best. I had plans to wear your favorite black dress, the one that fit like a second skin, lifting and displaying my ass and revealing all but a few inches of my thighs. I pride myself on the muscles in my legs, and get a real rush from showing them off to you.

I showered and took extra care to ensure that my skin was smooth and soft. I hoped to elicit at least a murmur of appreciation when you ran your fingertips over my thigh later. I dried my hair and let it fall in gentle waves over my shoulder. I was wrapping up my makeup when I heard the front door creak. I was not dressed and was at my vanity in a black lace thong and bra when you entered the bedroom. I felt a frisson of excitement and nervousness as your eyes roamed from my face down my body. still wanted to impress you and felt more than a little self-congratulatory at the desire in your eyes and the smirking laugh that always indicates your approval.

You wrapped your arms around me and cupped my ass before squeezing tightly. I could feel your cock stiffening through your pants, and ran my hand over it before reminding you we had plans. I grabbed my dress from a hanger, stepped into it, and shimmied until it was perfectly adjusted. I could have sworn I heard you groan appreciatively as I moved about the room. I grabbed patent leather black pumps, and bent to slip them on. I made no efforts to hide my intentions, bending at the waist, causing the hem of my dress to slide up my thighs, exposing the bottom of my ass. That time, I definitely heard a groan escape your lips before I felt the thrilling sting of you spanking me. You deftly grabbed my hips from behind and I felt the unmistakable sensation of you grinding your erection against my ass. I bit my lip and moaned softly. Even through our clothes, I could tell you must have been painfully hard. I could imagine how purple the head of your cock would be, as I fantasized about dropping to my knees and taking it in my mouth.

I didn't want to rush tonight though. Reluctantly, I squirmed away and playfully swatted your arm. I strode to the mirror and checked my reflection. My cheeks and chest were flushed from arousal, but that only added to the look. I felt more seductive than I ever had in my life. I was about to step into the hallway and grab my purse when you stopped me and informed me the outline of my thong was clearly visible. I thought I had managed to pick one that was both practical and sexy, but I realized I could see the fabric through the skintight dress. I slipped my panties off and grabbed a new pair. Not as hot, but hopefully less obvious to passersby. I pulled this one up and readjusted my dress before checking myself out in the mirror. It was less obvious, but I could still tell. You assured me it was much better, and reminded me we had somewhere to be and a specific time to be there. One last look, we grabbed our belongings, and out the door we went.

In the car, I shifted nervously. Why had I dressed like this? What if we ran into someone we knew? I tugged at my dress, crossed and uncrossed my legs, and asked you repeatedly if you were sure no one would notice my underwear through my dress. You reassured me seemingly countless times and squeezed my knee as an intimate gesture of comfort. When we arrived at the theater and parked, it was still light out. I felt self-conscious now, walking along the sidewalk. I was sure people were staring. You held my hand and told me I looked fine.

Once inside the theater and seated, I asked again if you thought people would be staring at my panty lines. You repeated that it looked fine and the trailed off. You seemed to be thinking intently. I rose to go to the rest room and check myself in the mirror again when you leaned close and whispered in my ear. You very calmly told me to go to the rest room, but not to check my underwear. You told me to remove them and bring them to you.

I gaped at you momentarily before outwardly collecting myself. Inside, my thoughts raced. Yes, I often fantasized about not wearing underwear in public. I had done it occasionally in my early 20's, loving the gentle feeling of the breeze causing shivers up my thighs in a skirt or enjoying the roughness of the seam of my jeans spreading my pussy. I would rush home to stroke my clit until I came, panting and shaking. But I am older now, and more reserved. Could I really do something like that now?

You took my hand and squeezed it gently before dropping to stroke my thigh. You raised your eyebrows at me as if to ask if I were up to the challenge. I steeled myself and recalled that I had promised myself this would be a night to remember. You had turned the tables on me now, but I decided to approach it as exciting rather than intimidating. I stood and walked out of the theater, giving my hips a little extra sway.

In the restroom, I slid my thong down and concealed it in my purse. I tugged the hem of my dress as low as I could and took my first step towards the hallway. The sensation of air on my bare pussy was overwhelming and my knees nearly buckled. I wasn't sure I was going to make it back to the theater without coming, let alone through a movie. I walked slowly, with no attention to my gait. I wasn't aiming for seductiveness, I was just trying to retain some semblance of dignity. Every step brought a wave of excitement, wetness spreading across my barely concealed skin.

One foot in front of the other until I was back in my seat. I crossed my legs, and slipped my panties out of my purse. I discreetly reached into your pocket, leaving them there. I could tell I was flushed again, and when I looked, your pupils were dilated with excitement. I was surprised, since they typically only dilated that large right before you came. I took it as a sign that this night was going exactly as I had hoped. I tried to slow my heart rate, but didn't succeed. My nipples were hard, and my mind seemed determined to wander to what I wanted you to do to me. You sat stoically, holding my hand. Your ability to remain composed in all situations has always impressed me, and this was no different.

Luckily, the theater was nearly deserted. I felt less self-conscious since there was no one else in our row, which made room for me to enjoy the excitement of being so exposed. The theater darkened and the movie eventually began. I couldn't focus on the action, though. I was too distracted by what had happened so far, my current condition, and where the night would go. I worked hard to keep my hands from drifting to your lap, since all I wanted was to sate my intense desire and lust was impairing my judgement more with every minute.

Near the end of the movie, you shifted to release my hand and rested your palm on my knee. It was innocent to an observer, but it was electric to me. Slowly and discreetly, you began tracing your fingertips over my knee. Still innocent, but I could feel heat between my thighs. With an achingly slow pace, you drew looping shapes up my thigh. I had kept my legs firmly crossed throughout the movie, but now I gently parted them. I worried about doing something truly indecent, but you stopped just short of the fabric of my dress.

For the rest of the movie, you kept on tracing up and down my thigh. Occasionally, you would dip inward, stroking the inside of my thigh and causing me to part my legs further. You never violated the boundary of my dress, though. It was excruciating and thrilling, and I could feel how wet my pussy had become. The inside of my upper thighs was damp from all the excitement. I was torn between keeping my wits about me and wanting to feel you rub my aching, swollen clit until I came. When the credits began to roll, I reluctantly crossed my legs and adjusted my dress before standing to leave.

The walk to the car was interminable. We talked, but all I could focus on was making it home and into the house. A short drive later, the car was barely parked before I was racing to the door. The lock was sticking and my hands were shaking as you stepped behind me and squeezed my ass. I moaned and giggled while wrestling with the lock. It clicked open just as you expertly reached one hand between my legs and slipped a perfectly long finger into my soaking wet pussy. My vision blurred as I wobbled and practically tumbled through the door. I regained my balance and kicked off my shoes. I immediately became the most impatient version of myself.

You calmly sat and untied your shoes while I shifted and whimpered. With your shoes off, I grabbed your hands to tug you upward, but you brushed off my advance and stood, twirling me in the process. I stepped into the living room, with you behind me. You roughly yanked the hem of my dress up, exposing my bare ass. A forceful swat with your left hand before you pushed me over the back of the couch. My ass and pussy were displayed while I could rest my hands on the cushions to steady myself. I couldn't see you but I felt your fingertips run the length of my wet slit before you pushed two fingers deep inside me. I moaned and felt the muscles deep within me contract as you stroked.

"You're so wet," you nearly growled, as I attempted to lift my hips to meet your fingers. I was on the verge of coming, when I felt you shift your hand. I'm disappointed that you've denied me, but then I felt your index finger, slick with my juices, slide down my ass to rest against my perfectly pink asshole. I bet you were admiring it while you fingered me, thinking about pressing your cock against it until you could slide inside me slowly. I felt your finger massaging gently. I was aroused but relaxed, so it would have been easy for you to slip your finger in to the hilt, and I probably would have screamed with pleasure. I wanted something else, though.

I forced myself upwards and stood, turning to face you. I kissed you forcefully, my tongue in your mouth. Then I tugged your hand and led you to the bedroom. I stripped off my dress and bra, standing fully naked in front of you. My breasts were flushed and my nipples were achingly hard. My pussy was bare except for a small patch of neatly trimmed dark hair. Even standing, you could see my lips were swollen pink and shining with wetness.

You undressed quickly, but I was able to reach you and tug your boxers down, allowing your swollen cock to spring free. It bobbed impressively, the head as purple as I had imagined. The foreskin was still not completely pushed back, but I saw precome glistening on the head. I dropped to my knees and licked it off slowly before using my lips to push your foreskin back. I flicked my tongue over your frenulum, and felt your cock twitch as you moaned. I held the head of your cock in my mouth while circling my tongue around it. You thrust your hips forward, but I held them still with my hands as I slowly slid you deeper into my mouth. I paused with you buried as deep in my throat as you could go, and moaned. The effect was as intended, and the vibrations of my throat and tongue caused you to become harder than I had imagined possible. I released your hips and allowed you to rest your hands on the back of my head. Your hips rocked back and forth as you fucked my mouth, watching yourself in the mirror. I looked up and locked eyes with you before taking control again and pulling away. I took your cock in my mouth once more and swirled my tongue around the head. I could sense you were frustrated, but I wanted this to last.

I climbed onto the bed on my hands and knees and crawled toward the headboard. I knew you wanted to come, but I wanted to give you every bit of enjoyment I could before you exploded. When I reached the pillows, I lowered my chest to the mattress while remaining on my knees. I reached behind myself and grabbed my ass with both hands, spreading it open. I expected you to react immediately, but instead you rubbed a flattened palm along my ass, down over my pussy.

"What do you want me to do?" You asked teasingly.

I whimpered. We had never talked much during sex, so when it happened, it was especially thrilling. I stepped up to the challenge.

"I want you to rim me."

You groaned appreciatively and buried your face in my ass. I immediately felt your tongue, so warm and soft, circling my tight asshole. I relaxed into the sensation and felt my pussy become hotter. My muscles contracted as your tongue stroked insistently.

Your enthusiasm for all things anal was never secret, not from the first time we slept together and you surprised me by licking me until I came. It was a feeling I loved instantly, and I was delighted every time you flipped me onto my stomach, hoping to feel your beard stubble as you spread my cheeks. Tonight was the best it had ever been, as your tongue explored until I began to sink into the mattress. I had to let go and use my arms to prop myself up, but without missing a beat, you used both hands to grip my ass firmly and spread it open. For good measure, you slipped lower and ran your tongue along my slit causing me to shiver and moan before refocusing your attention.

I was close to coming, and you burying two fingers in my pussy while your tongue probed my ass sent me over the edge. I collapsed forward with a guttural scream. I lay there momentarily, enjoying the waves of pleasure that rolled through me, when I heard the scraping of a drawer opening. I didn't need to open my eyes to know that I should remain face down. If you had it your way, that was just the preview.

I remained relaxed and comfortable as I felt you slip a finger into my pussy, swirling it gently. You have perfect hands, strong with long fingers that are both elegant and masculine. At this moment, with you stroking my g spot, I want to pull your hand to my mouth and lick my juices from it. I resisted my impulses, and submitted to what I hoped you planned to do next.

I shivered from anticipation as I felt you remove your fingers from deep inside me and slide upward until I felt the pad of your middle finger rest against my bare asshole. I giggled a little and wiggled my hips. I felt a gentle pressure as you pushed one finger inside me. You massaged me as you pushed deeper inside and I could feel your first knuckle, then your second. Soon you paused, finger buried as deep as possible. I felt my muscles squeezing you tightly, and I moaned your name as you began to slowly pump your finger in and out.

I heard rustling and a quiet click as you removed your finger. A moment later, I felt you massaging lube over my pouting hole. With two fingers, you worked more lube inside me. I was nearly purring from enjoyment, when I felt your weight shifting. I tried to crane my neck to see what you were doing, but before I could reposition myself, I felt the unmistakable smoothness of silicone. I was willing to bet it was one of the anal training butt plugs you bought me after we began dating, but I was curious as to which size. The smallest one is so slender I'm sure it could slip into even a very tight asshole with no more than a little discomfort, but the largest one requires practice. I was hoping that you would begin with the middle one, which stretches me enough to feel pleasantly full and provides just enough pain to be exhilarating.

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byMagicalKitten© 4 comments/ 13236 views/ 14 favorites

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