Tuesday: Kissed Three, Fucked One [m/f] | 2016

So I'm still relatively recently single (less than a year), but putting a toe into the dating pool. Pursuing potentially serious-ish options (something beyond the usual realm of FWBs or one-night adventures). I'm 37, fit, blonde-ish brown hair. Green eyes. Decent sized hands... With that in mind, here's my story from yesterday.

I met Lindsay for lunch.. it was our third date (first was lunch as well, then an afternoon in a park). She's 30, dark-red hair cut short, Amelie style. Thin, with perky b-cups and amazing hips and a perfect ass. She's quirky, with a quick smile and a bounce to her step. She met me with a kiss and put her hand through my arm and we walked into the hipster vegetarian restaurant that just came to town. Easy smiles, quick conversation. Flirting, light pressing of feet and knees. Sidelong glances. After lunch we walk the neighborhood, ducking into doorways, making out like teenagers. Grinning. But it ends - we both have to go back to work and that's that.

Since things with Lindsay are just starting, I had simultaneously agreed (some time ago) to meet up with Amy for dinner last night. Amy is tall, with short blonde hair. Curvier than Lindsay, also more assertive. Experienced. Present. In her late 30's.

Amy and I had had quick after-work drinks a few weeks back - an incredibly pleasant 30 minutes of conversation with some genuine moments of connection - that can be so rare and fleeting in such settings. We went to a Greek tapas place in the trendy restaurant district and drank rose and it became clear that the connection was real. And as we talked about our families and plans and upcoming travel, the food disappeared. Subtle flirting. And a sweet but simple, subtle, good night kiss.. and plans to meet again after she gets back from a work trip overseas.

I rode my bike home. 9ish. Smiling, but horny as fuck. And when I get home and check my phone, sure enough - there's a text from Molly. Molly is my newest FWB. A dark haired, dark nippled animal-loving 40-something. We'd fucked for the first time about a week ago - but here she was again. Asking if we could play. And, of course, I said yes. She told me to bring condoms, so after a quick stop at 7-11 I was on my way..

I knocked on the door and she opened it in yoga pants and a t-shirt. No bra. No panties. I said hi and pulled her in for a kiss. Ran my hand down her back, cupped her ass, spun her around and playfully pushed her towards the bedroom.

She had lit candles. Made the bed. And fell backwards, legs spread. I climbed on top of her and pressed my thigh between her legs, rubbing her pussy.. my hands pushing her t-shirt up. Kissing down her neck. She moaned. She wanted my cock. Begged me for it. I pinned her arms down and looked down at her.. aching.

I stood up and undressed quickly. Tugged her yoga pants off and worked my way up her legs to her pussy. Licking, flicking, teasing. Feeling her moan. Tasting her salty sweetness. She pulled me up. "Cock. Now." I grabbed a condom and slowly, inch by inch, slipped in. Watching her face. Eyes meeting. Kissing deeply. Then I fucked her hard, deep throbbing strokes. She writhed, moaned, pushed against me. I pinned her arms, then let her go - flipped her over and took her from behind. Tits dangling. Grabbing her hips.

I warned her I was cumming and we exploded together. Moaning. Collapsing on her bed. While her pomeranians scratched on outside of her bedroom door... Slowly coming back to our senses.

I needed that.