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.

12 thoughts on “my first time with another woman, part 2

  1. Hi shae… you might do a bit of editing on this post…the name of Chandra’s husband appears differently in spots. Just wanted to point it out in case you unintentionally strayed from anonymity…

    Liked by 1 person

  2. I found myself comparing Chandra to Amanda, in some ways. I see similarities. They both seem quite socially adept, dedicated, organized, and, to use your term, “well put together.” But, in Chandra’s case, you seem to have been a temporary playtoy. You are Amanda’s playtoy, as well, but obviously, to me anyway, Amanda holds your happiness, fulfillment, contentment, and well being in high priority. That’s not necessarily a common trait among all doms/dommes, only the good ones. As stated in one of Dylan’s 1979 tunes, “You’re gonna have to serve somebody.” This is especially true of you, shae. Regardless of whether you are involved in BDSM, someone is going to dominate you. That will be required of anyone desiring to retain your interest. This is not a criticism. It is, in fact, the shining aura completing your substantial, and rare, inner and outer beauty. I am quite glad that Amanda is the person dominating you.
    “(this was back in that bygone era when I still wore a bra and panties, sigh)”
    I am glad that you are wistful about wearing a bra and panties. I am also glad that you are never allowed to do so, and I hope that you never are, not even just once.
    I wish for you that, for the remainder of your days, you are owned, by a responsible and caring person, thoroughly, publicly, and openly dominated, sexually objectified, humiliated, embarrassed, exposed, shared, used, whipped, and roughly taken, exactly as you have chosen to be. I hope that you will always be just as humiliated and embarrassed by the above as you are now, i.e. that you never become jaded. I also hope that you continue to be made just as conflicted, wet, satisfied, and fulfilled as you are now. But, of course, that is Mistress Amanda’s call.
    To many, I would not seem to be wishing you well, but it is what I wish, for someone of whom I have become rather fond.
    I see that I have run rather far afield. Mea culpa.

    Liked by 1 person

    1. Silkenlash, methinks you have found the voice with which to talk to me, dominant and assumptive, reminding me of my place and purpose. You expected this would thrill me submissively. And you would be right in that.

      I struggled a bit in accurately reporting Chandra’s personality. You are right she is like Amanda in some ways. I perhaps have a weakness for professional women who bed me. They both have an air of business formality which is authoritative, though Chandra’s approach is to work around people and Amanda’s approach is to work with people. The two of them are different physically — Chandra being slender and Amanda being more voluptuous. And Chandra was not dominant in any sense of D/s dominance — that is, her interest was never to own me, but to get me into bed. Amanda’s dominance is that of literally owning a person… All in all, yours is a really good comment, and now interesting for me to ponder on more.

      Yes, I was Chandra’s playtoy and am now Amanda’s playtoy, but that’s hardly remarkable — I am destined to be anyone’s playtoy. Which goes to your point, I think. Yes, someone is always going to dominate me, as you say — and no, I don’t take it as a criticism, you are exactly right in that. It may be that my affair with Chandra was something of a cautionary tale: it turned out well, even benign, but I am vulnerable “out there” in the wild, so to speak, and I could very easily wind up in the clutches of someone much less nurturing than Amanda. I actually have a keen awareness of these realities of possession and protection in my submissive life.

      You write this: “I wish for you that, for the remainder of your days you are… thoroughly, publicly, and openly dominated, sexually objectified, humiliated, embarrassed, exposed, shared, used, whipped, and roughly taken, exactly as you have chosen to be.” Again, you are speaking in the tones of my love language, knowing I will understand in this that you are “wishing me well.” Your further point is that you wish that I will never become jaded. That is for me the mystery of my slavery perhaps — that in fact, after nearly six years of 24/7 D/s life, I have not really gotten to a point where the important things feel old and common. Being “roughly taken” still feels to me like I’m being roughly taken. Being hung on a wall and made into a planter still feels as objectifying that is. Yes, I am trained, conditioned to certain things, but I am not jaded. Not sure why.

      Ultimately the harshest thing you said to me 😉 was your wish that I will never again wear a bra and panties. I actually have daydreams about the luxurious feeling of soft cotton cupping my breasts. But as long as I am under Amanda, I will never enjoy that. So rest easy in your imagined pleasure.

      Liked by 2 people

      1. Thank you, shae, for taking the time to write such an in depth response. I do, indeed, appreciate Mistress Amanda’s ban on undergarments. I despise bras.
        I certainly do wish you well, in exactly the way that you and I define “well.”
        Have a good, and hopefully exciting, weekend.

        Liked by 2 people

  3. Wonderful writing style to reflect the experience. Your choice of words always come across so appropriately…

    This was a well described ‘awakening’ story. Enjoyable read.

    It’s interesting, this reflecting and calling up memories from years past, and trying to weave them into our current understanding, isn’t it. I’m doing the same thing these days…

    Liked by 4 people

    1. Thank you, Cassandra… I’m a little surprised I hadn’t written about her before, but she is part of my “pre-history” (pre-D/s) that was a swirl of confusion about my beliefs and my sexuality. I’ve needed time to give me more clarity. Good then this has finally come out…

      Liked by 2 people

  4. There are few gifts as great as being able to recall a past lover fondly. The memories aren’t clouded with thoughts of what could have been or caution that your much older self might have given your much younger self. When you’re free to relive the joy and pleasure of those experiences without any lingering anger or resentment, it’s a beautiful thing. I’m glad that Chandra was able to do that for you.

    Liked by 1 person

    1. Thank you, Dave. It’s interesting to go back to that time and back to my experience of Chandra. I think that the passage of time provides greater perspective, and it’s now clear that Chandra “happened” to me at a necessary time in my sexual awakening.

      Liked by 1 person

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