This was some time ago – I was in my mid-30s, and still enjoying the free and easy/commitment-free bachelor life. Dating was a luxurious mixture of the bar scene (not always a favorite given my introvert tendencies), occasional blind dates with friends-of-friends and/or their coworkers, and the awkwardly fun and diabolically frustrating dating sites.

I agreed to meet a woman after trading emails with her via a dating site. It was a very chilly Saturday night. She lived in Rockville and I was then living near Tysons Corner, so we “split the difference” and met at one of her preferred places in Bethesda. The restaurant was busy, especially since cold nights like this usually meant people going into hibernation mode and staying in with a bottle or three of wine rather than daring frostbite for cocktails. I was a little early since 495 is always a crap shoot, and I gave myself plenty of time to arrive (I hate being late). I texted the date to let her know I was already there and began nursing a drink to ease the meeting-someone-new nerves and warm up a little. She arrived a few minutes late and then filled the next 90 minutes with small talk, funny stories and the typical socially-awkward-getting-to-know-you conversation inherent with any first online date scenario.

As time passed, the bar area filled up more than when I first got there. On one side of me was a pair of women, best friends from the bits of their conversation I overheard. The one closest to me had one of those beautifully unique and contagious laughs that was impossible to ignore, no matter where you were in the crowd. She was also exercising a slightly distracting habit of bumping her shoulder into mine whenever she leaned back in even heavier laughter.

Meanwhile, the tone of my date was suffering a bit from increasingly harder to hear each other ambient room noise, and a severe lack of chemistry. As any veteran of the dating sights will tell you, there are clear omens of the “dead in the water” date. In this case, it was periods of awkward silence, the inevitable checking of the cell phone, and both of us surveying the crowd to see what else was going on. It’s nothing to take personally, that’s the nature of the beast with dating – sometimes online interest and chemistry doesn’t always translate in the real world. Eventually, I went out on a limb and asked about the obvious flatlining of our encounter, to which she agreed that the “spark” was absent. We agreed on a “nice to meet you/good luck with your search” ruling from the dating gods, and she bundled up and headed out.

I’m usually much better at planning ahead, but I spent the better part of the day doing a massive amount of household chores and cleaning, and ran out of time for any kind of substantial meal before going out that evening. As a result, I effectively downed two-and-a-half drinks on an empty stomach and was a little buzzed. Considering the minimum half-hour drive home to contend with, I decided to be responsible and ordered glasses of water and some small plate appetizers to “soak up” the alcohol.

I people watched as I refreshed myself – there were at least two other first dates, several established or married couples, and one table filled with a group of friends in the middle of their routine bar hopping. The two women next to me had settled down a bit, but were as planted in their bar stools as I was. After a few more unintentional shoulder bumps, the one with the wonderful laugh turned to me and observed my current predicament.

“Hey there,” she asked in a voice that was half songbird, half gin and tonic, “What happened to your date?”

“She took off a little while ago,” I replied.

“That’s a shame,” she said, “You two looked cute together.”

I shrugged, “Yeah, but chemistry wasn’t there.”

She laughed again, playfully nudged me with her shoulder. “She wasn’t upset that I was trying to get your attention or something like that?”

“Now that you mention it, I was wondering if you were up to something.”

She laughed again, leaning back in her chair. Her friend was chatting with a group on the other side from us, so I had her full attention. With a little food in me and enough time passed to ease off my buzz, I accepted her offer for another drink.

An hour passed as we reviewed each other’s vital information – what we did for work, where we grew up, how many relationships and/or marriages under our belts, favorite hobbies, etc. Her name was Sandy, and she was six months past her divorce that ended a staid-together-for-the-kids marriage. She lived a few blocks away in her newly leased apartment and normally found herself most Saturday nights either in the restaurant with friends or the odd online date herself. She was about my height, dark but highlighted blonde hair, eyes changed from sea blue to green to light brown depending on the light, and a figure given way by her perfectly-chosen, tight sweater. Sandy was the perfect blend of shape and curves (i.e., generous bust, still defined waist, perfectly imperfect stomach, and very grabbable hips and ass). I couldn’t identify her perfume, but it was light and not so flowery that I needed Allegra. She was a bit proactive about her touchy-feely habits than I’m used to, but didn’t mind either.

I elected that the hotel down the street would work out as an alternative to not driving home, so we continued to talk, flirt and drink. As the alcohol collected in our systems and the attraction grew more evident, the touching gently turned into longer, and more intimate contact. Sandy’s friend had long wandered off by now and the crowd was starting to thin. Our drinks had long since been consumed, melted ice and all. Still not entirely sure where things were going, I told her that I was planning on getting a room at the hotel down the street thanks to my intoxicated state.

Sandy had a smile on her face – the kind that instantly tells you there’s something going on and that you’ll probably like it. She said she was ready to take off and invited back to her place. As I contemplated what that meant, we looked into each other’s eyes and ever so smoothly tilted our heads into a long, deep kiss. Her style wasn’t as strong as mine, as I could feel my tongue “leading” hers. I took the opportunity to slide my hand from the small of her back to caress her ass, and elicited a half gasp/half pleased moan from her. We settled our tabs, made way to the restrooms for a quick pit stop and stumbled out into the night.

It was bitter cold outside and I wrapped my arm over her shoulder in a useless attempt to share warmth since we were both wearing leather jackets. Fortunately, my car was parked in a garage that opened in the morning and her apartment tower was a short walk away. By the time we got to her building’s lobby, we were running to get warm again, and the elevator was thankfully ready and waiting for us.

A short elevator ride up, accompanied by an equally fun but brief make out session, we walked onto her floor and into her apartment. She only moved in a month ago, as evidenced by a few stray unpacked boxes and unhung pictures. She clicked on a radio already set to the classic rock station and gave me a quick tour of her abode.

In the smaller than it should be kitchen, I noticed a set of shelves with a lot of bakery supplies. Sandy said she did a lot of baking – both for herself and competitions. She was at the counter mixing some fresh drinks as I eyed our tight quarters. She glanced behind me and smiled again.

I sidled up behind her, wrapping my arms around her waist and pressed against her back. Admittedly, I was already a little hard in anticipation of how the night was going. I felt her freeze slightly, but not sure from my sudden movement or noticing my unmistakable arousal. I felt her relax and finish pouring the drinks as I nuzzled her neck and gently brushed my hand against her breast. She nearly purred.

We sat down on the couch, shoes on the floor, sipping drinks and sometimes touching or holding hands, sometimes letting them wander. The conversation wandered from previous subjects to how the actual evening deviated so far from our separate expectations (i.e., she hanging out with her friend, me having a no frills first date). Sandy asked if I did this kind of thing often, and I told her that picking up women in bars is something I was never good at (which is true to this day). I asked her in return, and she said that I was the first man to get this far with her since her husband. Sandy admitted (turning a little bit pink) that except for a nearly worn out vibrator hiding in her nightstand, she was long overdue for a good orgasm.

Without missing a beat, I set my drink down next to hers, gently grabbed the back of her head and leaned into a deep kiss that made the ones at the bar and in the elevator seem innocent by comparison. Her arms wrapped around my back. We took turns kissing, nuzzling each other’s necks, playing with our ears. Her hands went down, occasionally sliding into my jeans, while I slipped one of mine up her sweater to feel the generous curve of her breasts. She wore a v-neck sweater that offer just enough cleavage to entice me down and kiss. As I did, she leaned her head back, enjoying what I was doing. Her one hand reached around to my front and ever so gently felt how hard I was, then leaned away from me.

Before I could ask, she held up one finger to say “just give me a moment” and disappeared into her bedroom. Mere minutes later I heard her call to me.

As I walked into the bedroom, she had lit several candles and was waiting on the bed, now wearing a black tank top and panties. I don’t know if it was what she had on or the dim lighting, but her curves looked even more inviting as I gazed at her. When I got to the foot of the bed, she crawled forward and effortlessly unlatched my belt and pulled down my jeans as I took off my own sweater and t-shirt. She let out a nervous giggle as she stroked my hard cock through my briefs, even touching the small spot of pre-cum that had formed with the tip of her finger. She stood up on her knees while still on the mattress. We kissed again, this time my body completely up against hers. I could tell her panties were slightly damp up against me, and she gently wrapped her fingers around my now rock hard cock. I pulled her tank top off over her head and felt her breasts against my bare chest. Her erect nipples danced across my pecks. Sandy then leaned back, pulling me up and on top of her.

For what seemed like an eternity, we kissed, necked, licked and sucked all over each other’s chests. Her breasts were a wonderland for my mouth and tongue to explore, kissing and tracing the tip of my tongue over every curve, sliding onto her nipples. My hands dove into her panties, feeling the curve of her ass and the perfectly shaved wetness between her legs.

While nuzzling her breasts, I began moving down on her, only to feel her hands grab me as if to say “wait, not yet.” She immediately went down on me, kissing and licking the length of my shaft. She explored every nuance and detail of me, even gently taking each ball into her mouth to suck on. Finally, with fingers wrapped around the base, she began rhythmically taking me in and out of her mouth. The warmth and wetness of her mouth was like silk around my manhood, and drew out my first moan of the evening. She took her time down there, making sure to taste and explore every bit of me. I could see her rubbing her hand inside her panties as she sucked on me, causing her own moans to vibrate on me. Finally, she pulled me wet, warm and very hard cock out and tenderly pressed it to the side of her face, her eyes closed, smiling and still caressing it with her hand.

She rose back to kiss and I helped her pull off her now definitely damp panties. As we kissed, my cocked pressed against her, just above a wet and expectant pussy. Again, I made to go down on her, but she stopped again, then rolled over and pulled out a condom from the nightstand. Without missing a beat she ripped open the wrapper and quickly put it on , stoking my cock as she slid it down.

She laid back with her legs spread apart and I rolled on top of her. Carefully, I guided the tip of my cock down along her lips, very moist and warm. I felt her shudder as I pass over her clit and she gasped as I firmly began sliding myself inside her. Soon we were moving back and forth as I slide in and out. I couldn’t help but stare her gorgeous breasts moving back and forth with my every thrust and her face meld from one countenance to the next. Eventually I stopped, turned her over and entered from behind, grabbing her hips so I could be faster and more forceful. She got on her knees and I grabbed her breasts from behind, squeezing and holding them as I continued moving inside of her.

Somehow, she knew when I was ready to, and made stop and pull out. Over her, she quickly pulled off the condom and stroked my slick cock until I came all over her stomach. She pulled me closer, and rubbed my still throbbing cock onto her, rubbing it in the warm, salty emission covering her lower abdomen. She gestured the bathroom and I got to clean myself off and bring back a warm and wet hand towel to take care of her. We spend time holding one another, trading off more time having it in different positions, and eventually falling asleep sometime in the early morning hours.

Morning arrived with us curled around one another, still naked. As we awoke, we merged into a spooning position with her back to me, with my cock grown hard again as it pressed and rubbed against her ass. My hands glided over her form, from gently holding her breasts and playing with her nipples between my fingers, to sliding down her stomach and fingering her wet clit and pussy. She managed to get ahold of another condom, and without changing positions, we went another round of me entering her until I came hard again, this time inside of her.

As we basked in the afterglow, I began taking a look around the room, finally noticing several family pictures. I couldn’t help but notice in a few were what must have been her daughters, but they were easily well into their teens and taken not too long ago given how Sandy looked in them. When Sandy noticed me staring, she offered they were indeed her daughters.

I paused for a moment, then asked “They’re lovely. You must’ve had them very young.”

Sandy grinned a bit, “Not young. I’ll bet you don’t know my age.”

“Are you daring to guess?”

“Absolutely.”

I thought for a moment. “If I had to guess, I’d say very early forties.”

Sandy beamed a bit more, “If only. Would you believe fifty two?”

“Seriously?”

“Seriously,” she purred. “ bother you?”

“No,” I replied, “Besides, it doesn’t change anything about the past night.”

We eventually arose and got cleaned up. I had to head home, both amused and turned on by having had such a good time with a woman who was in her teens when I was born, yet was every bit as attractive and alluring as anyone half her age. We traded cell numbers and playfully texted back and forth over the next week, having to pass on an immediate get together because of her family obligations. We met again when her same friend from night wanted to go line dancing. I nearly said no since a really bad dancer (and wasn’t a big country fan), but Sandy insisted since she wasn’t much of a dancer either. We spent most of evening the bar as her friend danced with pretty much everyone, then eventually went back to her place for more intimate fun.

As time went on, our texting slowly died down, my work took over and I assumed her own life went off in whatever direction it went in. I still think of her every now and then since she was amazingly fun to with. I sometimes wonder where she is and what happened to her.