my first time with another woman, part 2

My memories of that first time are sometimes vivid and otherwise sketchy. I remember we had arrived early afternoon the day before the convention. We’d agreed to unpack, freshen up, and then wander over to the convention center to get early registration.

Chandra knocked on the adjoining door between our two hotel rooms, and I opened it. She stood before me perfectly naked.

I remember the moment because this was different from all the common undress that girlfriends share in high school locker rooms, college dorm bathrooms, makeshift dressing rooms for bridesmaids at weddings. Chandra’s bald nudity at the adjoining door of my hotel room that day was unabashedly sexual and laser-targeted at me.

Her lithe beauty shocked me even as I relished it. Her legs were shapely and long, her hips wide. She had petite breasts, round, the size of oranges. She had brushed her hair from the trip, and it now fell perfectly around her face, inward arcs touching her jaw line.

She stood in the doorway as if it were a picture frame and perhaps that’s why this is so indelible in my mind.

I know that one of my many attractions to her was about her “unapologetic life” — she did things boldly without looking back, without justification, without shame. My whole upbringing had been broiled in shame, especially the teaching that sex was shameful.

Here, Chandra stood, her body proposing sex with me and without apology or shame. Framed by a doorway, she was the picture of what I wasn’t.

These days, when I occasionally reflect on my affair with Chandra, I see this snapshot in my mind’s eye.

---

I was eager for whatever was next, but also nervous in doing this forbidden thing which I’d never dared do before. In my nervousness I often make funny. And this is what I did as Chandra stepped through the picture frame.

“What?” I asked. “No flowers, no wine? A girl needs to be properly courted.”

She looked surprised, but then played along. She thought for a moment, a crooked smile on her face. She went back into her hotel room and soon came back with items in her hands. She held out to me a complimentary copy of Orlando magazine, the cover photo featuring a botanical garden attraction. “Here are your flowers,” she said. And she held out to me a tiny bottle of Chablis from the room mini-fridge. “Here’s your wine. Consider yourself properly courted.”

“Makes me feel very special,” I said.

“Actually, I’ve been courting you a long time.”

“Two months.”

“Much longer. You have no idea.”

It was something like that. She would later tell me she had seen me early in the year at some open house, and I had been in her sights ever since.

---

Looking back, there were vibes in this with her that I see now but probably was only faintly aware of then.

Chandra was a lot of things I was not — put together, elegant, powerful, bold, authoritative. I was klutzy, disorganized, and compliant. She was neat and tidy; I was messy. She had sexual confidence. I had sexual repression. Chandra represented a lot of things I wanted to be.

There was also that which is now obvious: Chandra was dominant. I was distantly aware of my submissiveness at the time, but I wasn’t yet mapping dom-sub as significant traits in people or as a sexual dynamic in me. But clearly Chandra dominated me relationally and I submitted to it eagerly. It’s obvious now.

This with her happened perhaps for those hidden reasons. Or perhaps just because we both were in lust for each other.

---

After the “flowers and wine,” Chandra had stepped naked into my room, and I said something about not getting the memo for the dress code for the party. Ha, ha.

I remember snippets of our words, but not most of them. I don’t recall if she again played along with my nervous humor. But I do remember that at some point she said, “I want to undress you myself.”

I hadn’t known anyone whose lust for me was so apparent, so forward.

I was in T-shirt and jeans, probably the least sensual outfit to get out of, certainly not gracefully. But Chandra pulled my tee over my head, sending my red hair everywhere, and unbuttoned my jeans, sliding them down over my hips. I was left in a bra and panties (this was back in that bygone era when I still wore a bra and panties, sigh) and Chandra played with me that way for a while, caressing me through my underwear and teasing herself with my body.

Eventually she unclasped my bra and slid it from my shoulders. She squealed “Oh, god!” as she saw them revealed. She cupped them, squeezing them with delight.

I’m sure I had blushed and stood passively in her objectification of me, but I loved it.

She got me out of my panties — well, I don’t remember that specifically, but she must have, for I somehow wound up in bed completely naked with her tongue inside me.

---

I can’t honestly say I remember specifics of our lust-making that afternoon. But one thing I recall is saying to her, “I’ve never done this before.”

“I know,” she replied. “That’s why I want you.”

---

This wouldn’t be my only sex with Chandra, of course. We literally shared the same bed throughout the convention. (We actually attended the convention too, somehow squeezing in time for business between our dalliances.) And after this convention week, Chandra and I were together on occasion over following months. So there are other memories of our intimacies, and that afternoon is mixed among them.

But I remember some specific things from that first afternoon:

I remember she held my hand, guiding me down between her legs, and she talked me through the process of giving her oral sex.

I remember how wet she got, how it pooled at the entrance of her pussy. She was messy that way in sex, so different it was from how tidily put together she was in public.

I remember how Chandra took to calling me “babygirl” in our sex together that first day, and then calling me that on the floor of the convention, making me blush.

I remember she had a special way of kissing my nipples, taking them between her lips, sucking, and swirling her tongue around them.

I remember discovering that when Chandra made me come, it was different in nature from what I’d experienced a few times with men — richer, deeper, and more complex somehow.

And perhaps what I remember most of that first afternoon with Chandra is how soft her pussy lips were on my tongue.

It was like this all week at the convention.

---

Even then, I knew better than to believe Chandra was in love with me. I knew I was her conquest, one of many. And likewise, coming back from that convention week, I realized I wasn’t “in love” with her either. I think I learned you can have a euphoric sexual experience with someone without actually being in love with them.

Once back in our day-to-day business lives, we found ways occasionally to be together. Chandra found a coffee shop some forty-five minutes away where no one would recognize us. When schedules would permit, we’d go there for coffee and kisses. Later, she would rent us a room in one of the hotels there.

Once, I met her husband. It was a real estate banquet, a charity event. Chandra and her husband attended. I was there representing my business, along with Carol, my assistant, and David, one of the new agents I’d hired. I didn’t see much of Chandra all evening, but at one point she found me. She introduced me to her husband, Josh, and told him about my real estate business. We all talked awhile. It was uneventful, although I noticed how he was trim and handsome and seemed as put together as she was.

Shortly after that, she broke up with me. To her credit, she did so in person. A final coffee break with her. She said she needed to focus more on her husband.

---

I cried a little later that day, but truly was rather quickly over her — I think an indication that our intercourse was lust not love. I let go of her rather easily, to be honest.

It always seemed to me there was something mysterious about Chandra. Well, not mysterious, really, but hidden. I had no doubt she seduced women like me for her personal pleasures. But later I wondered if that was more coupled with her husband than anyone knew.

It occurred to me that their marriage might be alternative (this was long before I really knew what “alternative” was). I wondered if Chandra indulged her sapphic pleasures, and husband Josh knew all about them. The possibility then was that in some cases, Chandra would bring the other woman into their marriage to become a threesome.

If so, when I had been introduced to Josh briefly at the banquet, maybe he just wasn’t into me. Maybe I wasn’t his type.

No matter, because there was no way I would have been capable of that back then.

As it happened, Chandra and I had our moment in time, and it was beautiful, and she was for me an important experience in my self-discovery. I shall always be grateful to her for that.