She was an OKCupid date, about 21, petite with an innocent-naive vibe. Slender and pretty. I was 23 at the time and unsure what of what I wanted.
We met at a cocktail bar and were flirting from the start, holding hands within the first 20 minutes. She’d grabbed my hand after a few obvious brushes of her hand with mine. So undercutting the doughy-eyed girl look was a drive to get laid, or touched, or something.
I could’ve been projecting, but she also rested her other hand on my thigh, so signs were pretty obvious. I enjoyed the fact that she was confident without the experience. And I was confident she had little experience from the way she said “I’m sorry, I don’t have much experience on dates, is this too forward?” It wasn’t.
We made out there in the bar like barbarians. I got lipstick smudged on my face and we left, some in-the-right dickheads cheering as we left.
On the train back to mine she hugged in close to me, and we made quiet conversation about family and avoided sticking our tongues in each other’s mouths. At my stop, we got out, my hand resting on the small of her back as we made our way towards mine. I was about 15 minutes walk away and we had to go down some small roads. Down one back passage, well maintained but dark, she stopped and pulled in close, looking up at me and biting her lip.
“You’re not a bad man, are you?”
I cocked my eyebrow “No. I only do bad things to people who like it”
“Oh,” she pressed in closer “that’s good, I guess”
“Tell if you’re wanting a bad man tonight”
She nodded slowly. I put my arms around her, and got so close our lips were brushing.
“Are you comfortable telling me to stop?”
She drew back a little and smiled wryly. “Of course, silly, otherwise I wouldn’t be down a back alley with you!”
I smacked her ass and kissed her deeply. “You’re mine then. Just a little bit further…” We walked on.
As soon as we got inside the door of my 1-bed, I pushed her against the wall, got in close to her ear. “I’m going to fuck you.” I placed her hand against the hardening bulge in my pants. She gasped – I’m not huge, mind you, I just didn’t think she was expecting me to approach her quite like this. She squeezed lightly and I continued “I’m going to play with you until you’re soaking wet, and then this cock is going to go into you until I’m satisfied. Do you understand?”
“Yes sir. Please sir” she was looking at me with those doughy eyes again, pupils so dilated that the irises were mere slivers.
I ran my hand up the inside of her thigh, caressing until I was just brushing against her panties, her dressed lifting up against my wrist. “You’re going to get this cock rock hard, and then I’m going to take it and slide it right into here” – I pressed firmly on her mound and clit, cupping it. The dress made it a little awkward so I hitched it up further until it was over her ass.
“Um…” she was breathing heavily and looked uncertain. I put my hand back on her thigh but left her dressed still hitched up. “Uhhh -” she bit her lip over another smile “please use me sir. I’m yours sir.”
“Good girl” and I picked her up. She looked at me, mouth open, breathing heavily. I made our to the bedroom.
Fortunately I had tidied up earlier. Bed was made, piles of clothes and papers and miscellaneous crap squared away in the proper place, or otherwise shoved into a closed space. So I laid her down on my bed and didn’t feel self conscious.
I lay right next to her, hand on her upper thigh, continued in her ear “you’re so fucking hot. I wanted to get you in bed from the moment I saw you tonight,” I paused, “earlier, in fact. When you were talking about your volunteer work for the Red Cross. Er – not to be unsexy, but hand sanitiser is in the top drawer.” Her eyes widened, but she grabbed it. Both of us sanitised and air pungent with alcohol (I know, I know, but it wore off quickly), I pulled her panties off – purple lace as I found out – and socks too. She seemed… dazed and happy? Uncertain but excited about what was happening, I thought. I stood up.
“Be a good good girl and these off,” I said, gesturing to my pants. I took off my top.
“Yes… yes sir!” She sat up and fumbled with my button and zip pulling down both jeans and boxers. My cock was semi erect and suddenly right there in her face. She looked at it for a moment, her hands on my waist, my bottoms round my ankles, which I stepped out of. Those big round eyes of hers pierced mine as she got the tip of my cock in in her mouth and ran her tongue all the way around the head. Again, then licking the underside and sucking. As I stiffened, she pushed in deeper.
“Ungh. Such a good girl.” She replied with an interesting throaty affirmation, and took it all inside her mouth, then throat. I gasped, and so did she when she pushed me all the way out.
“Ugm, I’m not sure this is going to fit, sir” she was now staring at my absolutely average sized cock, stroking it with her hand. Sweet little lies. “Are – are you going to use me now sir?”
“Strip.” She did, pulling her dress over her head and throwing it on the floor, followed by her purple bra. She was toned and slender and wonderfully pretty. I told her this last part. She broke character, looking a little bashful, though I’m sure she’d been told it a million times before. Just… maybe not in exactly this context. I brought her back in “Lay back down. I’m going to go down on you now, and I’ll be very unhappy if you cum. Do you understand?” She looked taken aback, but she nodded and did as she was told.
I lay in between her legs, hooking my arms under her thighs, my hands on her waist. She was completely shaven. I started by kissing her thighs, alternating between them, breathing hard on her clit when I passed. I did this for about a minute, in which she got increasingly restless, bucking her hips lightly towards my mouth. I kissed her clit through the hood and brushed it with the inside of lip. She moaned and she pressed my head down – though she was a good girl and didn’t do it too hard. I brushed harder, and we both increased in tempo until we found the right rhythm.
Sooner than I expected, she pushed my head back. “I’m going to cum sir. Fuck me please sir.”
I wasn’t as hard as before, so as I lay beside her and leant over to get condoms from the nightstand, I told her to do the obvious. She quickly got me rock hard again with her tongue, and I rolled the condom over it.
She got on her back, I lifted her legs into the jackhammer position. She was muttering ‘please, please, please….’ repeatedly – so rushed I could barely make it out. I rubbed the head of my cock around her entrance – the condom took some of the wetness out so I used spit to make it easier. I slowly entered her, the condom pulling back a bit but ultimately she was hot and tight and wet. She’d stopped her muttering, looking at me wide-eyed, moaning.
I was all the way inside her.
And I fucked her.
She’d already been close, so she came pretty quickly. Or I think she did from her facial expressions and the way she loosened up slightly after some seconds. But I continued to slam her, and she was pulling me in, so I didn’t stop.
The hard wet slapping noise filled the room. I wasn’t close, despite the effort. We changed into the – what do you call it? Spork position – right angles to each other. I put my hand on my mound and clit and pressed in as I penetrated her. She tightened up again and started to push my hands away but I grabbed her hands with my free one.
“Please – ungh – sir, it’s too much.”
“Don’t you want to… want to.. Unm”
Her tightening had pushed me over the edge. I tensed, cumming, grabbing her arms and pulling myself into her as deep as I could go.
We lay like that for a few moments, giggling a little. I eventually pulled out – to both of our dissatisfaction – and went to get towels and to throw the condom away.
“Do you want me to… anything else at the moment?” I asked, laying my hand on her belly.
“God no. I might become catatonic if I were to cum again.” she said. Her voice got small, “Cuddle me?”
“Gladly”
We spooned until we got sleepy. She stayed the night.
Source: reddit.com/r/sexystories/comments/rv0nor/first_date_mf