My First (and Worst!) OKCupid Date

Worst First Date

When you finally decide to take the plunge and leap into the online dating pool, you don’t expect your first experience there to be your worst … but that’s just what happened to me.  Read all about it in my Singles Warehouse post!

Now, ladies and gents, just remember: if your date “has something to show you” in his or her car, run like hell … or at least be ready to.

First Date Weekend

optionsWithout my 9-5 and without the Architect in my life, I have a fair bit of time on my hands. It only took me a couple minutes of thinking to decide it was time to meet some new folks. Although I consistently get a lot of interest from the fellas on OKCupid, I was thinking more about ladies this time. After a little bit of back and forth messaging over the last couple weeks with several people, I had first dates set up with nine different people … and four of them were this weekend.

On Friday night, the Programmer and I went to a group gathering at a local pizzeria. I had been chatting with the Stamp Licker (which reminds me: although some of these professional labels are correct, not all of them are, by a longshot, and I (naturally) reserve the right to call each person anything I damn well want) online for a week or two, even though she first messaged me in May. I knew the Stamp Licker would be at this gathering, but she didn’t know I would. The look on her face when she recognized me was delightful. “Aren’t you…?” she said. “Yep,” I told her, and took the seat next to her to chat for a half hour or so. That conversation went pretty well … but it didn’t matter, since she and boyfriend are off to another state far far away in a couple weeks. Right then. I took the Programmer home afterward, and the combination of his tongue and fingers and a new toy of mine almost killed me with orgasm after orgasm of insane intensity. My muscles are STILL a little sore from all of that (says SDAW, with a wicked grin on her face).

Saturday, Harry Potter (yep, I can call them whatever I want, I said) and I were to meet at 5pm over at my favorite local bar. This particular place is often suggested to me by others, which is amusing, since it’s often my first suggestion. In this case, he had picked it. I arrived an hour and a half early, thinking I’d get some work done on this-a-here borrowed laptop … but a few of my friends were sitting in a booth in the corner. I sat with them, figuring as it became closer to 5, I’d pick out a table of my own to sit with Harry Potter and chat. But Harry was a good 45 minutes early himself … and had also brought friends. We ditched them, respectively, he grabbed a fresh beer for each of us, and we sat down to talk. It was instantly clear that Harry was overwhelmed by me and my open, friendly personality. I just wasn’t sure if it was good overwhelmed or bad overwhelmed. The more we talked, the more I realized it had to be the latter. Dear sweet little Harry was a virgin with zero dating experience. He was terrified. I made up some excuse that I had to get going, and he was out the door before I had even finished bussing the table.

I sat back down to finally get to work. But then another group of my friends arrived, bit by bit, until there were twelve or so of us, gathered around the table, playing games and creating our own game. I was in the midst of drawing a “Sand Witch” card for their set when I got a text message from a gal I’d been chatting with on FetLife: “What are you up to tonight?” We’d been saying we should meet up for quite a while, it was fitting together our schedules that had stopped us. I suggested we get together around 9pm. “Great,” she said, “how about ________?” I laughed and told her I was already there, come whenever. She arrived just as my friends and I were wrapping a game – perfect timing! I said my goodbyes, and sat down with Eve (as in Adam and), yet again with a fresh beer. Eve was wonderful. Beautiful with a wild blond mane and crooked smile, open, warm, soft-spoken yet strongly confident. We were having a great time, until the boys showed up – two single fellas, to whom we appeared to be two friends without a date, I’m sure.

They sat down and chatted us up about every boring topic you can think of. We endured them for a bit and moved on to find another place to sit, no doubt bruising two male egos in the process. After a long, long conversation ranging from exes to jobs to family to current partners, Eve and I admitted it was late and she had quite a bit of driving to do. Standing outside the bar, I leaned down to hug her goodbye. There was a good 7 inches’ difference in our heights; probably more like 9 with the shoes I wore – and it occurred to me, a moment after she walked away without a goodnight kiss, that said kiss was MY responsibility, simply because of the height disparity. I always seem to freeze up when it comes to making a move with a girl – which is ridiculous, considering how shy I’m not with just about any man. Sigh. I texted Eve and apologized for the slip. She texted back with a smile: “we can take care of that next time.” My heart fluttered.

This afternoon, I met up with the IT Guy for brunch at 1:30. Just to continue the trend of the weekend, a table at the restaurant was occupied by yet more friends of mine, and the IT Guy waited politely while I said hello. IT Guy’s accent charmed me, as French accents tend to do; softening all the hard edges of his English and making his speech sound like a slow song. We talked about any- and everything; I finally had to cut the conversation short and declare that I had other things to do this evening. He was clearly interested in seeing me again, and then he suggested that I come over to his place and wait for the appliance repair guy with him tomorrow morning. Hmm. Like many of my dates, he was confusing my openness about sex with my willingness to fuck anybody at any time. Ah, no thanks. I told him I was free on Saturday during the day, and we made another lunch date … and we’ll have to see how that one goes.

I wore the same trusty denim skirt to all four dates.  It’s a dark-wash pencil with buttons down the front, and it’s positively awesome on me.  And I’m exhausted from all of this meeting new people. First dates mean being on my toes in more ways than one, and I find myself longing for the comfort of an old lover this evening. There’s just something about being with someone who already knows a little bit about what to expect, I think.  Maybe I’ll see what the Communist is up to tonight…. he hasn’t seen that denim skirt yet.

A Date with the Programmer


When you’re in this chair, I’m the boss.

The Programmer and I had plans for Sunday night, but I was in an awful mood.  I told him so over IM.  “Me too,” he admitted.  He suggested we meet in the middle for a hug and a grilled cheese sandwich.  Of course nobody ordered the grilled cheese.  And instead of just the hug, we headed right on back to his place.

I first met the Programmer on a dating site a few years ago, and I didn’t know it, but I was to learn all kinds of new things from him.  We went to bed together on our first date, and there was the first surprise: he wore a chastity device.  He produced a key, and in between sexy kisses and touches, he explained to me who kept his keys and why today was a very rare exception – he really should never keep one with him.  The Programmer didn’t do vanilla sex.  He wanted me in charge in every way.  He was my first submissive … and I wasn’t even a Domme yet!  The Programmer helped change that as we got to know each other, and I discovered that not only did I have quite a flair for domination – I was good at it! – but I enjoyed it thoroughly.  It turned me on to see him struggle against restraints; to watch him trying as hard as he could not to beg me; to then deny him any release at all.  I was a secondary partner of his; we saw each other every few weeks.  On the day he handed me his key to keep, I said casually while slipping it on a chain around my neck, “I’ve been thinking that perhaps it’s a good idea if you never orgasm with me.”  He moaned instantly in tortured arousal.  “Never,” I would whisper in his ear while we were out and about, and I’d feel him shiver at that single word.  We drifted apart but remained friends as things in our complicated polyamorous lives changed and changed again.  Circumstances were right for us to begin seeing each other again last year, and since then we’ve done some great  things for one another.  In fact, I’d say Sunday night was possibly our best work ever.

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A Date with the Architect

May 17 with the Architect

Just us and the big beautiful outdoors.

The Architect knocked on my door precisely at 6:00 on Thursday and handed me a grocery bag.  After a sweet kiss hello, I finished cleaning the strawberries, and we gathered up fruit, cheese, and crackers and stepped out the back door.  We spread a blanket, took off our shoes and opened our beers.  The breeze was perfect and the sun was warm.  After a few bites, we laid on our backs and looked up through the softly swaying leaves of the trees.  The sky was a perfect blue with not a cloud in sight, and just as I was about to tell him how great this moment was, the Architect squeezed my hand and whispered, “This is wonderful.”  This is one of my favorite things about dates with the Architect.  Just being together is what we both love.

As the sun went down, the breeze got chilly, and when I slipped my icy bare foot underneath his sock, the Architect gathered our picnic and brought me inside.  He stopped me from cleaning up the kitchen with a kiss that had my head swimming.  He led me to the bedroom and laid me gently down, running his hands up and down my body over my clothing.  He kissed every inch of skin he could get to without undressing me, while I writhed and moaned softly underneath his lips.  “Architect,” I breathed to him, calling his name, telling him I didn’t want to wait any longer.  He took my clothes off one piece at a time, bit by slow bit, kissing everything he exposed. He stood up to take off his own clothes, and I smiled to see his cock was already thick and hard.

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SDAW on Twitter

  • Totally happyexcited these days about a new lover. The Artist is such a win. 2 years ago
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  • ... just sort of wind up feeling like personal failure, no matter how clearly it isn't. I'm a little heartbroken today. Wish it'd go away. 2 years ago
  • I'm good at breaking up. I've done lots of it. But these, the ones where it's not because you don't love each other... 2 years ago
  • RT @gcollins11: The Tigers are 'rebooting'? WTF are they, Windows Vista? 2 years ago