Doug the sailor, his wine, and his shag carpet

I didn’t want to delay meeting Doug (the sailor) because continuing a text and phone relationship before meeting face to face? We all know what can happen.

I’m in a very busy period of work right now, we are in the midst of technical deployments and coming up to a big deadline, so a Friday afternoon which was quiet was a perfect time. I took a half day vacation day and decided to meet Doug at the west end of our city where he docks his boat.

I had it all planned. Leave before my city’s notorious traffic kicked in, spend a couple hours with Doug, drive back into the Center of the city for dinner with a girlfriend at her place, then go home to meet Jake.

What could possibly go wrong?

The drive to the boat was perfect. I took two work calls and made excellent time. I was super organized with two different outfits in my trunk (my orange bikini in case I lost my mind and a casual skirt to wear if I wanted just the bikini top), and my iPad in case the date went horribly wrong and I had to kill time in a cafe somewhere.

Doug looked like his pictures and he greeted me heartily with a smile, kiss, and a hug. He chatted away as we walked along the dock to his boat. He likes to joke (exclaiming “here it is!” as we walk to a dinghy).

He’d done two sweet things. First, he brought flowers from his garden. Peonies – my hands-down favorite, which he didn’t know. Second, while he’d asked what I like to drink (if you’re curious: bubbly, extra dry rose, dry white, or if beer, bud light lime), I didn’t expect him to have bought all of it. Just so I could have what I wanted.

He poured me a drink, gave me a tour (I use that term loosely; it’s a small boat) we sat on the back and started to talk. He’s not well-educated; I found myself cringing internally at some of his language (nothing terrible, things like using “must of” instead of “must have”). He’s a smoker, but managed to hold off for quite a while. He smokes these funny skinny “women’s” cigarettes because he says he’s trying to quit. Probably like every other smoker.

The word that mostly comes to mind with Doug is FUN. He makes a lot of jokes, he likes to have a good time. He’s retiring in less than two years with a full pension from his union job, and will probably sell everything and move to the Caribbean. He doesn’t strike me as a complicated guy. Which has its appeal in some ways.

He told me I’m the first woman he’s met since he last became single about a year ago. He’s never been married, no kids, but he’s had some long-term relationships.

I can’t even remember what we talked about. But time flew. He suggested we go for a walk to get some food and before we left I told him I wanted to kiss him. Which we did. And it was good. He giggled and told me I was making him horny. He said I was a good kisser.

We left to get food – on our way out he introduced me to his friends who had boats off the same dock. While we shared our plates he asked me questions about some of my OK Cupid questions. Sex, naturally. We had some good laughs.

We went back to his boat, he poured some more drinks at which point I realized I was not going to be able to drive when I was supposed to leave. I had to sober up before I could drive. I texted my girlfriend to let her know. Doug and I started kissing in his boat. He reached down and put his hand between my legs, stroking me through the fabric. He took off my shirt and latched his mouth to my nipples.

He got very excited. He led me the few feet to where the platform bed was in the nose of the boat. There were new cushions on the bottom, still wrapped in plastic. But the rest of the space – remember it’s from the 1970s – was covered in carpet. I commented on it and he laughed about it while removing my pants, saying he was gradually getting rid of it all.

I realized he was about to enter me without a condom – so I stopped him and he had to root around in the shelves to find one. I could tell from how long it took he wasn’t a sex-in-his-boat-pro, or hadn’t been for a long time.

Unfortunately, the sex was rather uneventful for me. For Doug, it was great. The most memorable part was him pulling out and I could see the condom was gone. He said it fell off. He wasn’t constantly hard so it seems plausible, but I was not impressed. The next day I told him it was uncool and asked when he’d last been tested. He said it had been a year since he’d had sex and he’d had a full physical within that time.

Doug was on cloud nine; he felt amazing and kept telling me as much. I was happy to have provided such a good experience. I was surprised at myself for having sex with him, but in retrospect I know it was a combination of alcohol, fun, and knowing he was in no way a player. I sobered up, rejected his multiple requests to have me stay the night and hang out with his friends, hopped in my car and took off to my next destination.

Next Post

15 thoughts on “Doug the sailor, his wine, and his shag carpet

  1. Your stories don’t make me laugh normally but this one did. Very different from anything you’ve told us before. Sounds like something from a teenage sea cadets summer camp.

    Serious question though. You’ve found yourself in a few awkward situations now. Why do you not carry condoms yourself. I wouldn’t dream of having sex with someone I didn’t really know without one?

    Anyway I like this story and I think even you were taken by the novelty of it.

    (Sorry for punctuation. I’m on my phone).

    Ps. What was his OK Cupid %.

    • Yeah this was different for sure and it did have me laughing. The carpet was ridiculous.
      And the condoms? Yes it’s an excellent point. I haven’t had first date sex in not sure how long (yes I could just look at my posts to figure it out). But carrying them make a lot of sense.

  2. When my brother was trying to quit smoking, he would buy down to the store brand in quality and then taper further down with Virginia Slims. Weird, but it seems to have worked.

  3. Sounds like you made his day indeed! I always carry condoms with me. But I’ve had the same 3 in my purse for months now. Lol! I’m going to guess that you made it home in time to see Jake. And I’m sure if you did it was a much more satisfying encounter.

  4. I won a carrier bag full of condoms in a raffle recently. If I lived to a hundred and fifty I would never use them all. Still better than winning the first prize of an inflatable sheep (don’t ask). Seriously it sounds like you made an old man very happy lol.

  5. I had a good chuckle at this – it was like you wre doing him a favor with the sex. I loved it.

What do you think?