She looked so beautiful sitting across the table from me – her lips red, brown eyes accentuated by dark eye-liner, cute hair cut in a bob. Still the cute girl-next-door look with which I was familiar, but with just the right amount of added sexiness.

Her name was Robyn and it was our first time hanging out alone outside of the office. There’d been some light flirting over the months since she’d joined, but it wasn’t until we matched on a dating app that things moved to another level.

As the office manager she sat at the front desk, looking 23 despite being 10 years older. Because of her fresh-faced look I’d always thought of her as being fairly innocent, and was shocked (pleasantly so) at how dirty some of her messages were. As I sat in the restaurant, watching her so daintily sip her wine and cut her steak, one message in particular stuck in my mind: “maybe if the date goes well I’ll let you fuck me in the ass ;)”.

She was talking now, telling me a story about someone at her previous job, but I was struggling to concentrate. All I could imagine was how she would look without the short black cocktail skirt she wore, what her moans would sound like while I was inside her, and how soft her skin would feel under my fingertips. Could this night really end with me thrust deep inside her ass? I adjusted in my seat, making more room for my hardening cock.

Robyn finished her story, but I missed the punchline in my dreaming and now she was looking at me expecting a response.

“You look very beautiful this evening,” I managed in the end. She blushed and sipped her wine coyly. “Thanks.”

“You look really good in that dress” I continued, pressing the advantage.

“I was worried it might be too slutty?”

“No…just the right amount.”

We finished our meal with further flirtation, and while we waited for the bill she sat back in her chair and contemplated me.

“What now?” she asked.

“How about a walk?”

I’d chosen a restaurant at the Waterfront and as we walked into the cool night I slipped my hand into hers. It was as smooth and delicate as I had pictured and we walked in comfortable silence along the row of boats bobbing in the water among the shimmering lights.

Our walk took us to the end of the pier, where we stopped and leaned against the railings. She looked up at me – her eyes were two dark pools I wanted to disappear into, her lips full and irresistable. No words were needed. I bent towards her and felt her soft, warm lips against mine. She tasted very slightly of strawberry, and as I pulled her body closer to me I felt her tongue slip into my mouth and caress my own.

It was a long time we stayed standing there, the passion of our embrace increasing with each passing moment. As our bodies pressed together I ran my hand down the back of her dress, clasping the firm curve of her buttock. She writhed under my grip, body rubbing against my throbbing dick. I was enjoying the moment, but my crotch was desperate for release.

Instead I kept exploring her body with my hands. Around her ass, onto the smooth exposed skin of her bare leg, then up and under her dress. She moved her body away from me then, not to get away, but to allow more space to touch here; her lips were still glued to mine.

I brought my hand around the front of her leg and found the elastic of her underwear, felt the clammy wetness as I pushed them to one side, and finally found my finger nestled inside her soft, wet pussy.

Her first gasp of pleasure was heaven to my ears – a soft sigh of relief mixed with a low moan of satisfaction. Her fingers clutched at my neck as I began to move around inside her. She adjusted her stance, standing with legs further apart to allow me deeper into the centre of her body. Her moans were increasing as I slid in and out and she buried her head in my chest.

My middle finger was now buried in her up to my knuckle, and when I next thrust it inside her I let my index finger enter her too, sliding in effortlessly. She gave a slight cry and looked up at me, mouth open, eyes hungry. I bent down and once again tasted her soft lips and hungry tongue.

After several more thrusts I withdrew my fingers and ran them up her swollen lips in search of her clit. Her body shivered involuntarily as I found her nub, and she bit down on my lip while I rubbed it up and down.

The pleasure was taking hold of her now – as I rubbed up and down she forced her pelvis into my hand. Eventually her teeth released my lip and she clung to me, trying to stifle her moans in my shirt. Once more her fingers dug into my hair as her climax exploded within her.

I kept rubbing her wet clit, slowing the pace as her breathing returned to normal, eventually leaving her slumped in my arms. Withdrawing my hand I slid her panties back over her soaking cunt and gently ran in over her thighs. Once more I looked down into those beautiful dark eyes.

“Take me home and fuck me,” she said. I didn’t need to be told twice.

As we walked back along the pier my dick continued to throb against my pants, aching for release. She nestled under my arm as we walked and then said, “I think you’ve earned your reward.”

“What do you mean?” I replied innocently.

She looked up at me with a mischievous grin, “You know what I mean.”

I almost exploded right there.

Fortunately her apartment wasn’t far, so no more than half an hour later we were entwined on her couch; my shirt was off and her hand was finally wrapped around my cock. I’d pulled down the top of her dress and was fondling her small breasts when she released me and stood up

“Give me 5 minutes to freshen up and then come into my room,” she instructed, walking towards her bedroom. “And knock before you enter.”

I watched as she disappeared behind the door. Even with her dress disheveled she looked as desirable as any woman I’ve seen.

I sat alone in the lounge, my engorged member periscoping out of my opened pants, precum dribbling onto my stomach. In readiness for the main event I removed my remaining clothes and slowly stroked myself to maintain my firmness. How much longer did I have to wait?

When I judged the time was up I crossed the room and knocked on her door. There was a brief sound of movement and then her voice, “Come in.” I pushed open the door and was greeted by the most arousing sight I have ever experienced.

She was completely naked, kneeling on the bed on all fours, her head facing away from me. Her bedside light was on, giving enough glow to keep the ambiance while still allowing me to take her all in.

Her legs were shapely and smooth and between them I could see the lower lobes of her pussy peeking through. Above her thighs her cute, rounded ass cheeks were parted, framing her perfect, puckered anus. Her back was arched and her tits hung lightly from her chest. She considered me over her shoulder, watching as I examined her body.

“You want to fuck me in the ass?”

I had no words. Like a mute I nodded and approached her bed.

As I knelt behind her on the bed my eyes were glued to her asshole, looking so unassuming and small – this orifice she wanted to pleasure me with, to sheath my dick in. I would consider myself average-sized, but even so was skeptical she could fit me in. Resting my weight on my knees I placed my hands on her lower back.

“Don’t forget to use lots of lube” she instructed.

Lying beside her was a tube of it and I squeezed a generous portion onto her crack. Using my finger I swirled it round her hole, feeling the ridges of it under my touch. When all the fluid was distributed I pressed my finger into her pursed anus. She moaned at that and rocked back toward me. I watched as my finger disappeared into her ass, and then reappeared as she rocked forward again. She continued this movement a few more times while I countered her motion with my hand.

“Put another one in,” she moaned and she rocked back and forth.

The second finger met some resistance as I tried to enter her, but the lube, together with her movements, meant it was very soon inside her as well.

My dick was oozing precum and my balls were aching with desire as we continued our dance and when I could hardly bear it any longer I hear her say, “Now fuck me.”

Without hesitation I withdrew my fingers, grasped my cock and pointed it at her target, shuffling forward on my knees to approach her. With one hand on her back I placed my swollen head on the entrance to her ass, my fluid mixing with the lube already on her.

I pushed firmly, feeling the resistance of her body to me entering her. I felt her push back against me like she had on my fingers. The muscle was giving way now as I pushed harder. From beneath me, Robyn gave another moan, pleasure mixed with pain, and then her body yielded and my head was inside her. The pleasure I felt was overwhelming, and I waited a moment to compose myself before I felt her once more pushing back against me and felt the full length of my shaft become enveloped in her tight ass, my balls resting on her firm cheeks.

Then I began to fuck her.

I started slowly at first, keeping my head inside her while the rest of me thrust and withdrew, gripping her by the hips to pull myself into her and then out. She responded to my rhythm, matching my thrusts, driving herself into me, with each push burying me inside her. My whole being was focussed on the pleasure I was feeling, relishing the tightness that surrounded my member.

I could hear myself moaning now, and my moans mixed with hers. Watching her bobbing back I couldn’t believe this was actually happening. That my sweet, naive-looking colleague was so adept at being fucked like I’d wished to fuck so many other girls. There was no romance in our actions now, we’d been overtaken with desire and a primal yearning for the ultimate pleasure.

Beneath me I could see her rubbing between her legs with one hand, supporting herself on the other. From her moans it sounded like she was close to climaxing again, but I wasn’t able to concentrate. I could feel my own climax building now, building from my balls and moving up my shaft.

“Where should I cum?” I gasped, unsure how much longer I could keep going.

“Inside me!” was all she could get out over the slapping of our flesh.

The feeling moving up my dick was starting to take over, the pleasure focussed at my centre was radiating throughout my body. Desperately I pounded into her, my orgasm swelling more than I’d ever felt before. I couldn’t breathe as my entire body went rigid, almost comatose with rapture.

And then finally I was cumming, each thrust spurting bursts of semen into her, further lubricating each penetrating lunge. It was several moments before my orgasm began to dissipate and my rhythm began to slow. It was then that I noticed how Robyn’s body had sagged, no longer propped up on her elbows, but lying with her face in the bedding, a contented sound issuing from her throats as I pulled myself into her wringing out the last of my pleasure.

Once content I let myself fall out of her and collapsed beside her on the bed, exhausted and satisfied. We lay like this for some time, kissing and caressing one another.

By the time I left the following morning I’d emptied myself into her two more times – once in her pussy, her knees folded up against her chest; and once with her lips wrapped around me,

jerking me into her mouth.

I arrived home satisfied with our evening, keen to see her again, and curious how I’d ever be able to look at her the same way at work again.