I Confessed My Secret Date with an Older Woman

I’m going to tell it exactly as it happened, without embellishing it, because there are things a man needs to confess even if it’s to strangers. For months she and I wrote to each other without ever seeing each other’s faces. I never heard her voice, never truly saw her eyes, only words on a screen that grew hotter with every message. The messages started as jokes, then flirting, and from there they moved on to describing in detail what we would do to each other if we had one another in front of us. She told me how she would slip her hand inside her pants while reading me, how she would come thinking of my cock burying itself all the way inside her, and I sent her photos of my hard dick for her. As time went by, instead of tiring of her, I wanted her more.

We both had partners. We both knew this should not happen. Maybe that’s why, when she finally proposed we meet, I didn’t hesitate for a second.

***

On the day of the date I hadn’t slept a wink. I drove for hours to her city, my head spinning, asking myself questions that had no answer. What if she didn’t like me in person? What if I regretted it? Despite my nerves, the trip felt short.

I parked at the address she had given me, a street set apart from the center, lightly trafficked, one of those streets that seem taken from a movie about lovers hiding from prying eyes. I got out of the car and waited on the sidewalk. I checked my phone: it was exactly time.

In the distance, a female silhouette appeared. I didn’t know it was her until she got close: short dark brown hair, huge sunglasses, a shoulder bag and a long light gray sleeveless dress. My heart was pounding out of my chest.

She stopped in front of me, took off her sunglasses and smiled.

—Hi, handsome —she said.

We exchanged two kisses on the cheek. She smelled good, of something warm, and suddenly my nerves vanished.

—Let’s go to your car —she asked—. Half the neighborhood knows me around here and I don’t want to give anyone anything to talk about.

We settled into the seats. I started the car and began following her directions.

—You didn’t do yourself justice when you described yourself —I confessed—. In person you’re much more attractive than I imagined.

—Are you always this flattering?

—Always. Don’t you like it? You’d be the first woman I’ve ever known who’s bothered by a compliment.

She laughed. While guiding me toward her house, she told me how hard it had been to decide to see me in secret. We reached her street and she pointed out her entrance, but she didn’t let me stop there.

—Keep going, go around the block. We’ll park on the street behind.

The plan was simple and discreet: she would go upstairs first and leave the door slightly open; I would go up after, a couple of minutes later.

***

I entered her apartment and she was already waiting behind the door. She shut it quickly. We stood staring at each other in silence, not really knowing how to begin what we had both been imagining for months.

I took a step, put my hands on her waist and brought my mouth to hers. Our lips brushed, teased, and when she parted them slightly my tongue sought the wetness of her mouth. We kissed like two kids in a corner of the schoolyard, with a hunger that had nothing to do with our age. I bit her lower lip and she returned it with a sucking pull that made my skin prickle. My hands slid down her back until I grabbed her ass over the dress, squeezing it with both hands, and she let out a moan into my mouth. I felt her belly pressed against my fly and felt my cock start swelling against her. Because that was what we were: two people approaching sixty kissing with the urgency of those who have just discovered desire.

She pulled away and took my hand.

—Come on, let’s go to my room.

She led me down the hall to the bedroom. It was a large room, almost all white: the walls, the bedding, the cushions, the curtains covering a balcony. The bed had an old black-bar headboard and, unable to help myself, I imagined her tied to it, legs spread and her cunt dripping. On a small table there was a bottle of rum, two glasses, a metal box, a lighter and an ashtray. She had everything ready.

She turned toward me and pinned me with a suddenly serious look.

—Listen carefully. It took me a lot to decide to be here with you today. My partner knows nothing about this and I want it to stay that way. In your emails you told me you were discreet and responsible. I hope those weren’t empty words. Don’t hurt me, and I’m not talking physically.

—I’m not that kind of man —I told her, smiling—. I prefer making love, not war.

She switched off the ceiling light and turned on the table lamp. That warm light changed everything. She opened the metal box, took out one of our cigarettes, the kind we liked, put it between my lips and brought the flame close.

—Let’s not rush —she murmured—. We have all night. Let’s make this unforgettable.

***

I took a couple of drags while watching her gather the skirt of her dress up. I passed her the cigarette and she inhaled deeply. With a quick motion she pulled the dress off over her head and there before me was her mature woman’s body, generous and full. A semitransparent black bra through which her dark, hard nipples could be made out, and a tiny thong of the same color that barely covered her cunt. She was the living image of temptation.

She took the cigarette from my mouth, took another drag, and in an authoritative voice gave me an order.

—Get naked. I want to see what you’re offering me.

I liked her game. I’m not used to taking orders and precisely because of that it lit me up. I played along: I took my shirt off slowly. She came closer, stroked my chest and offered me what was left of the cigarette.

—Keep going —she said—. So far I like it, but I want to see your weapons.

I took off my shoes without bending down and started unfastening my belt with calculated slowness. Her eyes did not leave my hands.

—Faster, you’re making me sick with want.

—Not so fast. The big prize is for the end.

I pulled my pants down to mid-thigh, just enough for her to see the underwear stretched over the bulge. She came over and grabbed me shamelessly, squeezing my cock over the fabric and feeling it grow under her fingers. I wasn’t fully hard yet; she tried to slip her fingers inside and I stopped her cold.

—Hold still. The show isn’t over yet.

She looked at me with a displeased face and pulled away. She didn’t like that I took control away from her, not for a second.

I finished taking off my pants, stroked myself over the fabric with both hands, slowly, enjoying how desperate she was becoming. And when I could take it no more, I tugged the waistband down and showed her my cock, hard, thick, the tip already shining with fluid.

I moved closer, took her hand and guided it to my dick. I felt her resistance: she didn’t want me dominating her, but she couldn’t resist touching me either. She closed her fingers around the shaft and began stroking me slowly, feeling me from top to bottom, drawing back the foreskin, playing with the soaked glans. I held her face, drove my tongue deep into her mouth and let her pump me while the cigarette buzz climbed through both of us.

Then, without warning, she squeezed my balls hard enough to make me grimace in pain. She looked at me with a wicked smile.

—Don’t you ever contradict me again —she whispered—, or you’ll have a bad time.

***

She reclaimed control in one swift motion. She went to the bed, swept the cushions aside with one slap, unfastened her bra and let it fall to the floor. Her big, heavy tits were freed, with stiff nipples pointing toward me. She sat on the edge.

—Come here. And kneel.

I put a cushion on the floor and knelt in front of her. She grabbed my chin, brought her face close to mine.

—Don’t forget: if you’re here it’s because I decided it. I’m in charge here. You’re my toy.

She spread her legs. My gaze locked onto that little scrap of fabric barely covering her cunt, already darkened by a damp stain. She took my head with both hands.

—Now show me what you know how to do with that tongue.

I pleased her slowly, licking over the fabric, soaking it even more with saliva, nibbling at the lips of her cunt through the thong. I traced her groin with the tip of my tongue until I felt her shudder. I dragged my flat tongue over her mound, went back down, licked her again over the fabric while she pushed her hips against my face. I let her believe she was in charge, that she had the control, that I did nothing without her permission. Her moans grew, her body surrendered, and the smell of her wet cunt had my cock dripping between my legs.

And when she finally pulled the thong aside and offered me her sex unimpeded, her pink, open cunt shining with slick, I held her wrists with one hand and caught her by surprise. Her disbelief left her unable to react. I buried my whole mouth in her pussy, sucking on her lips, sliding my tongue in as far as it would go, going up to her clit to suck it hard and then back down to fuck her with my tongue. She tried to close her legs and I sank my teeth into the inside of her thigh. I freed her wrists only to shove two fingers into her at once while I kept sucking her clit, moving my fingers upward, searching for the spot that made her writhe. Her legs trembled, she tried to break free, but pleasure had left her weak. I felt everything clenching around my fingers, felt a hot spurt wet my chin, and she kept coming again and again while I gave her no mercy. I don’t know whether she had one orgasm or several in a row.

When she started shifting uncomfortably, I pulled back, my mouth shining with her cum.

—Now it’s time to show you who’s in charge.

I rose, grabbed her by the ankles, spread her legs wide open, and drove my cock into her in one thrust, all the way in. Her scream was a mix of surprise, pleasure and a little pain that probably echoed through the whole building. Her cunt was so wet that my dick sank in without resistance until it knocked against her womb. Her role had just changed: she was no longer the mistress of the scene, but the slut letting herself be fucked. She looked at me unable to speak. Maybe she hadn’t expected that, but she was enjoying it.

I fucked her hard, relentlessly, pulling almost all the way out and slamming back in, setting the pace with my palms against her thighs. Her tits bounced with every shove. I grabbed one and brought it to my mouth, sucking her nipple while I kept fucking her. Little by little the pain turned entirely into pleasure: her hands clung to my arms, her legs opened for me and wrapped around my hips, pulling me in deeper.

—Harder, bastard, fuck me harder —she panted—, like that, like that, don’t stop.

I took her by the hips and pushed her farther to the center of the bed. I put her legs over my shoulders and entered her again in that position, much deeper. Every thrust tore a cry from her. I could feel her cunt squeezing my cock like a soaked fist. When I could hold back no longer, I pressed my chest to hers, she asked me in my ear to empty myself inside her and I did, unloading stream after stream of hot semen deep in her cunt, holding her tight while she exploded in another orgasm that made her dig her nails into my back.

We stayed like that for a good while, my cock still inside her, feeling it soften while my load trickled between her ass cheeks. Our bodies covered with a thin layer of sweat, our breathing ragged, and she was laughing softly against my neck.

***

Afterwards we showered one after the other and went back to the room. She had left a bucket with ice and some soft drinks on the table. I poured myself a straight rum and, a little later, she appeared wearing another thong, this time red, and some mid-heel sandals. She turned all the way around so I could look at her and came over asking me to pour her a rum with lemon.

—Do you like it? It’s been a while since I wore it.

Without getting up, I drew her toward me, put my hands on her hips and buried my face in her belly. Feeling her soft skin and her fingers tangling in my hair was a different kind of pleasure, calmer. I nibbled at the skin above the waistband of the thong, ran my tongue down her groin until I brushed the fabric and she jolted.

She sat on my lap with the glass in her hand, wrapped her arms around my neck, gave me a small kiss and asked for another cigarette. While she smoked, I stroked her breasts, pinching her nipples between thumb and forefinger until they were hard again. Then she stood up and went out for a moment.

—I have a surprise for you —she said from the hallway—. Well, for both of us. You’ll see.

***

She came back with the laptop, put on some music and got me out of bed.

—Music makes everything more intimate. Come on, I feel like dancing.

We danced pressed together, in silence, her arms around my neck, her face resting on my shoulder. I bit her neck like a vampire and she shivered. Her hips moved, rubbing against my crotch, and I felt my cock, tired and all, waking back up against her belly. Our bodies were talking, not words.

—Does your wife know you’re with me? —she asked in my ear.

—No. For now I’d rather it stay that way. Someday I’ll tell her, but right now I want to enjoy the extra thrill that infidelity gives us.

She took me to the edge of the bed, sat me down and knelt between my legs. She started playing with my dick without rushing, just for the pleasure of touching it, running her hand up and down, teasing the tip with her thumb. There was nothing left of the dominant woman from a little while earlier. I stroked her cheeks, made a slight gesture with my head and she, understanding me perfectly, gave me a conspiratorial smile before taking me into her mouth.

Time stopped. She took my whole cock into her mouth until I felt it hit the back of her throat and left it there for a few seconds, looking up at me from below with glassy eyes. Then she started moving her head up and down at a slow pace, sucking hard, letting strings of saliva escape and slide down her chin to fall onto her tits. She took my cock all the way out to run her tongue under the glans, to suck each of my balls one by one, and then swallowed me again to the hilt. The skill of her tongue, the softness of her lips, those naughty sideways glances... She took my hand and placed it on the back of her neck so I could set the pace. I began pushing her face against my cock, fucking her mouth, and she accepted everything, swallowing her saliva and moaning with her throat full.

I resisted coming as long as I could, but the idea of finishing in her mouth finally won. I let out a growl, my legs trembled and I gave in. I felt my cock throbbing in her mouth, shooting stream after stream of semen onto her tongue. When I opened my eyes, she was smiling at me, her mouth full, and without taking her eyes off me she swallowed every drop with an exaggerated gesture. Then she cleaned the tip with her tongue and squeezed the base with two fingers to wring out the last drops.

—Sweetheart, lie down and rest.

I lay down. She stroked my face, my neck, my chest, and between the exhaustion and the warmth I almost fell asleep.

***

Later we sat down and really talked. There’s nothing like the intimacy of an affair to loosen your tongue and make you honest.

—And you? —I asked her—. Will you tell your partner you cheated on them?

—Why would I tell them something that would only hurt them? I don’t even know how long this will last between us. Besides, like you, what’s forbidden turns me on. How boring life would be without crossing the occasional line.

She fixed herself another rum and lit another cigarette. She passed it to me and, out of curiosity, asked a question I hadn’t expected.

—Have you ever had anything with another man?

—No. A guy doesn’t attract me, doesn’t do it for me.

—And if it were someone who looked completely like a woman? Would you do it?

I took my time answering.

—It depends. If they looked and behaved like a real woman, what difference would the rest make? On all fours, what’s the difference?

I saw her take the last two drags with a certain anxiety. She handed me the cigarette and stood up.

—I’m going for a moment.

She took quite a while. When she returned, she came in completely naked and sat beside me.

—Do you want to take me from behind? Imagine what we were talking about.

She put her hand on me. At my age, things take time; there isn’t the vitality there used to be, but what her hand couldn’t do her mouth did. She bent down, took me between her lips again and spent a long while sucking me patiently, without rushing, until she felt me grow and harden for the third time that night. She took a tube of cream from the nightstand drawer and handed it to me.

—Are you sure? —I asked.

—With this it’ll be easy. Rub it on yourself and on me. It stings a little at first, but you’ll see right away. And don’t worry, you’re not the first.

She got on all fours at the edge of the bed and looked at me over her shoulder, waiting. The sight of her generous hips, of her big white ass opened before me, of the wrinkled dark little hole waiting for my cock, aroused me at once. I coated my cock well with the lubricant until it was shiny and slippery. Then I poured a good stream into her ass and spread it with my fingers, sliding them between her cheeks, circling her anus with the pad of my thumb before pushing. I prepared her with one finger, slowly, sinking it in little by little, listening to how she guided me.

—That’s it, that’s good. Little by little.

I slipped in a second finger and began to separate them inside her, opening her up. She let out a long gasp and pushed her hips back, asking for more. She hugged a cushion and buried her face in it. Seeing her like that, a woman nearing seventy, a grandmother and Sunday mass regular, with her ass in the air waiting for me to fuck it, made me wonder where her limit was. I suspected that for a woman as free as she was, there wasn’t one.

I rested the tip of my cock at her little hole and pushed carefully. The ring resisted, tight, until it gave and the head went in with a wet sound. She moaned into the cushion.

—Wait, wait —she panted—. One moment.

I stayed still, with only the glans inside, and stroked her back until I felt her relax. Then I began to push more, millimeter by millimeter, feeling her ass swallow my cock whole. When I was all the way in, with my hips pressed to her cheeks, pleasure clouded me completely. Her tight ass around my cock was a sensation unlike all the others, narrower, hotter. Seeing her submissive, surrendered, face crushed into the cushion and ass in the air for me, woke something darker in me.

She, who had wanted to be the dominant one, had ended up the one being dominated. I began to move slowly, pulling almost all the way out and driving back in to the hilt. Little by little I sped up. My thrusts became stronger, more brutal, with my hands dug into her hips to pull her against me. I smacked her ass, leaving a mark. At first her sounds were those of satisfaction, she moaned and asked for more, but as I let myself go, her protests grew. She lifted her head, babbled incoherent phrases and threw me a few insults —bastard, son of a bitch, slower— which I took, better or worse, as part of the game, and kept fucking her ass without letting up. I grabbed her hair and yanked her head back while I drove into her.

For a man my age to keep a third erection that night was almost a miracle. The miracle was her, insatiable. Unable to hold back any longer, with the final thrusts deeper, I finished with a growl, emptying what little I had left into her ass and collapsing over her back. I pulled my cock out and watched a thread of semen escape her open anus and run down her perineum.

***

We stayed motionless, breaths ragged, a huge silence between us. The room smelled of sweat, alcohol, tobacco and sex; between us we had turned it into something else. I sat on the edge of the bed and stroked her back, slowly, from shoulders to legs. She didn’t move. Her breathing was calm again.

She turned her head toward me and looked at me hard.

—You went too far. You treated me in a way I wasn’t expecting, you hurt me.

—Don’t complain so much —I shot back, cocky—. You asked me to do it.

—What you did has nothing to do with what I asked you for.

I tried to draw her toward me with a smug smile.

—Come on, don’t complain, I know you liked it.

She didn’t let me finish. She slapped me before I saw it coming, followed by an awkward silence.

—And you? Did you like it? —she asked.

I stood there looking stupid. She got up and left the room. The blow didn’t hurt; what hurt was the way she gave it to me. I had wanted to act like a tough guy and she knocked the wind out of my sails in a second.

When she came back, she approached more calmly.

—It’s late. What if we go to sleep?

—Okay. I want to leave early tomorrow, I’ll try not to wake you.

We got into bed, gave each other a goodnight kiss and each settled in our own way.

***

That’s all. I’m telling it because, months later, I still think about that night more than I should. If she ever reads this, she’ll know perfectly well I’m talking about us. And she’ll also know where to find me.