My awesome date tonight (F/M) (xpost from r/dirtypenpals) | 2016

(True story. Thought you would all enjoy. Originally an update to my own post on DPP. reddit)

I'll tell you what happened on my date:

I met her at a speakeasy-type place, a bar-within-a-bar. Quiet. Dark. She was 34, blonde, curvy in the right places, wearing a low-cut blouse and a tight black skirt. We sat and ordered drinks and talked; she was a little nervous at first but the drinks arrived and she relaxed (we both did). We talked about everything: Music, movies, our past relationships, family, politics. It was a good conversation, no lulls. She ordered another drink. We kept talking. She ordered a third, then went to the ladies' room. When she came back, I noticed that she'd undone one button on her blouse; her lacy bra was showing, along with her more of her creamy skin. I couldn't help but stare.

She finished her drink, and I asked if she wanted to go for a walk. We're in NYC, it's a beautiful warm night, cool for July. She said yes. I paid for the date (always) and we left. Outside on the sidewalk, she hooked her arm into mine and we walked. I felt her rub her soft breasts into my bicep when I made her laugh. At an intersection, I unhooked my arm and pointed to a tall building; this was done all so I could wrap my arm around the small of her back and feel the curve of her ass.

We walked a little more and I suggested grabbing a bite to eat. She said yes. We went in and ate a little. She ordered a glass of wine and said, 'Ask me any question.' 'OK, I said. Tell me about your first kiss.' She laughed and told me a story about kissing an older boy when she was 12. I told her about getting French kissed at 14. And suddenly the talk started to get more sexual. She asked me when I lost my virginity (late, 22); I asked her about hers (17, back seat of a car). We asked each other about our first oral sex experiences, giving and receiving. I started to feel a little warm and couldn't help but stare at the little bow on the front of her bra, and that little sliver of pale skin beneath it. She drank another glass of wine and said she was getting drunk, she was having too much fun and didn't want to go home yet. Neither did I.

The sex talk escalated. Threesomes. Same-sex experiences (hers). Kink. Under the table I felt her foot rub up my leg. She leaned over when she spoke, revealing more of her breasts. I asked her if she had ever slept with anyone on the first date. 'No!' she laughed. And then winked at me. It was time to go. She paid the check this time (but I offered) and we left.

Outside she basically threw herself at me, a long deep slow wet kiss. People walking by on the street. Neither of us cared. My hand went down her back, caressing her ass, and she pressed fully into me. 'I'm having a fun night,' she said. 'Me too,' I responded. 'Walk me home, it's not far' she said. I put my arm around her waist and we headed down 8th Avenue.

At the intersection of 8th and Jane, we stopped for the light, and she began sucking on my earlobe, breathing into my ear and basically driving me crazy. 'Easy,' I said, 'you're going to make it tough for me to walk.' 'That's the idea,' she said and ran her hand down my ass, cupping it. Fuck, I thought. I gotta get this woman home ASAP.

Two more blocks. Every thirty seconds we stopped to paw each other and shove our tongues down each other's throats. My cock was stiffening with each step. 'It's just right there,' she said, and then laid on the killer: 'But you can't come up.'

My cock deflated. All this buildup for nothing. She must have seen it on my face. 'I told you I don't sleep on the first date,' she said, biting my lower lip. 'I get it,' I lied. 'No big deal. I had fun.' She dragged her hand down my chest and cupped my cock. Yes, I was surprised. 'I didn't say the night was over.' She squeeze my dick, which sprang back to life. It was as surprised as me. 'There's a private garden for the residents. Through here.' She took out a key and led me to a gate. Unlocked it. I pressed my cock into her ass (and I'm thinking about it now and I want to cum from the memory alone). The gate opened and she led me in.

The garden was barely lit. She led me over to a little bench, hidden away behind a huge bush. She sat me on the bench, lifted up her skirt and straddled me, kissing me hard. She unbuttoned my shirt to my waist and ran her hands along my chest. I reached around and clutched her bare ass cheeks, felt the string of her thong, pulled on it. She bucked. My cock was completely solid now, raging steel.

She unbuttoned her blouse and opened her shirt, then lifted her beautiful left breast out of the bra. Her nipple was hard, huge. 'Suck it,' she commanded. I pressed my lips to her supple flesh and sucked, swirling my tongue around her nipple. She moaned, gasped. 'God!' She began to writhe against my cock. I sucked harder on her nipple, bit it, kissed it, licked it, sucked the other hard nipple through the lace of her bra. She held her breath and then released in a shudder. I reached under her thong strap and ran my fingers along her soaking, soaking pussy. 'Oh, my God!' she whispered (I'd totally forgotten that we were right outside of someone's window). She bucked against my cock, pressing her pussy into it, hard against hard. I clung to her ass and drew her in to me. I sucked her tit, bit her nipple hard... and then she came. She came about as hard than as any woman I've been with in my 45 years: Her fingernails dug into my neck, her other hand yanked at my hair, she pressed me into her tits until I couldn't breathe. Then she relaxed.

Holy fucking fuck.

Before I could think, move, ask a question, she kissed me hard again, unstraddled me and reached for my cock. My pants were wet from her pussy. 'Your turn,' she said. Dear God, I thought, what now? I was about to find out.

She pulled her skirt down and moved next to me on the bench, kissing me and caressing my cock through my pants. She moved her hand up along my bare chest, playing with and pinching my nipples. Yes. Yes. Yes. She sucked on my earlobe again. 'So I don't sleep on the first date,' she said. 'But I'll make sure you remember it.' She suckled my earlobe long and hard, and then reached down and unbuckled my belt, unbuttoned my pants and unzipped my fly. My cock strained against my boxer briefs. She rubbed it hard, and I was so hot that I almost came right then and there. 'Would you like me to suck your cock?' she whispered. I couldn't even speak, I just nodded mutely.

She reached down, and pulled my cock through the opening in my shorts. Feeling the cool air against its hardness made me nearly cum again. But she wrapped her fingers around it and squeezed. 'I love sucking cock,' she whispered, jerking me up and down, slowly at first, then faster. She kissed me again, softer this time, her tongue licking against my lower lip. She kissed down my chest, sucking and licking my nipples, still jerking my cock. Fuck. And then she dropped her mouth over it at once and SUCKED and I felt like I had just been shot through with 100,000 volts. Her lips went up and down, up and down on my shaft; her tongue darted around my head and frenulum. She reached through the legs of my boxers and grabbed my balls, moaning as she did. She sucked fast, she sucked slow. She sucked on the head alone (good Christ amazing), and then took me all in. All in. Her throat closed around my cock and I did everything in my mortal power not to shoot my load because it felt so fucking good. She didn't let up, just kept throat-fucking me. I grabbed her ass hard with one hand and her hair with the other and held on for dear life. After what seemed like a decade she came up for air. My cock was slick with her saliva and she jerked hard. Brought her lips to mine and kissed me. 'Do you want to cum now?' she asked. 'Yes and no,' I said; it was the truth. I wanted to cum so badly and yet I never wanted it to end. So she obliged, going down on me one more time, pumping my shaft with her soft lips, then burying my cock in her throat.

It was all I could take. I had to cum. I tapped her on the back and I felt her nod her head and I tightened every muscle in my body until I couldn't hold it any longer and --

WHOOOOOOOOOSSSSHHHHH!!! Like a fucking busted New York City fire hydrant on the hottest day of the summer. She kept her head on my cock, my head in her throat, taking every last bit of it, shaking as she swallowed it all. I pulled on her hair; I dug my fingernails into the fabric over her ass; I wanted to scream as loud as I could but only let out a whispered yawp as the orgasm just. Kept. Going.

And then it was done. She slowly lifted her head off my still-hard shaft like a vacuum cleaner, her lips and tongue getting any stray drop of cum. She kissed the head. Stroked it once or twice. Gripped it hard. 'Nice cock,' she said. I couldn't even respond.

She buttoned her blouse up and straightened her skirt. Then took my softening cock and tucked it back into my boxer briefs. She zipped up my pants and buttoned them. 'I had a lovely night,' she said. I still couldn't speak. 'I hope we can do it again sometime.' I nodded. 'Tomorrow?' I finally managed to get out.

TL;DR - Daddy got his cock sucked tonight and his mind blown tonight.