Unlike when I Googled “What to wear to a threesome,” or, later, “What to wear to a foursome” (equally unhelpful), Googling “What to wear to a sex date,” offers up numerous articles on the subject. For the most part, these articles recommend to avoid overly complex underwear, tricky clothing closures and heavy makeup.
[Side note: There are also some good articles on bringing up your menstrual cycle on a sex date, as I was still spotting a week after my period.]
In arranging my sex date with Jon, I had asked him for his preference among black, navy, pink and purple. He chose purple, so the lingerie choice was made. I then decided on thigh-high, black stockings (sexy and easier to deal with than tights), a black leather skirt with a big zipper running down the back (very easy to unzip and remove) and a velvet top (who doesn’t love touching velvet?). Unfortunately, since the light in the room was harsh, we kept the lights off, so the lingerie big reveal was less revealing, but he still appreciated the bra and panties (and me!).
Just prior to my arrival at the hotel, Jon texted me the room number and I went directly upstairs and knocked on the door. As much as I had been looking forward to our date, I was equally nervous since we’d only had one previous (relatively short) date. However, after about 20 minutes or so, I felt reasonably relaxed as we started to talk, sip some wine and began to kiss. Since we had the whole day, we were able to take our time and not feel rushed to have sex.
He was very giving and patient and I found myself able to truly enjoy being with him. He initially went down on me and I surrendered enough to have an orgasm; not the most intense one, but I was pleasantly surprised it happened at all, after my experiences with Hank, Kevin and Dan. We then engaged in 69, which I also enjoyed, especially in being able to give pleasure to him. Actual intercourse was a bit more complicated because he was not used to condoms and had some difficulty with his erection, but we did manage to connect in the end. But again, I was really delighted with how comfortable it all seemed given our limited knowledge of one another and how new this still is to me. As it is, Jon was only the second man with whom I have had intercourse since this all began (the first was Jake).
As we lay in bed, we drifted between verbal intimacy and physical intimacy, with Jon bringing me to orgasm several times throughout the afternoon. We also listened to music and shared fantasies and fetishes. He expressed interest in being spanked and trusted me to spank him since I had learned some techniques at a D/s class in the past. After I stopped spanking him, I asked him what he thought and he revealed that he had an erection (score one for Jeannie). In return, when asked and I admitted that I had not had my nipples bitten, Jon happily obliged, ultimately bringing me to orgasm (score one for Jon).
Eventually, it was nearly time to go, so we took a brief, sudsy shower together before gathering our things and heading out. Among our various conversations, I expressed how sexy I thought his invitation was and explained that if it hadn’t been so sexy, I likely would have declined due to the newness of our relationship. In the spirit of full disclosure, Jon revealed that he had Googled, “How to ask for a sex date” (score one for Google 😊).