A Sunday ago, Master arranged for me to hang out with his golf buddies at the club. They played a round early in the morning. I went to church, as usual, then joined them in the clubhouse lounge around 11:30.
For some time I have been interested in Master McKenna’s golf life with his friends, curious about their male-bro executive culture on the golf course. I’ve just wanted to know more about this man who rules me, his relationships outside the mansion, and what makes him tick socially.
Of course, that was before my courtesan dates with these men themselves, back when they were still strangers to me. Now, they and I know each other (oh so well), and that makes me all the more interested in this golfing world that bonds them all to each other.
At the same time, because of my escort relationship with the men, this get-together at the club was nervous-making. I have slept with four of them, and the two others are scheduled with me for this summer. How would they act around me side by side with each other? How should I act with them as a group of men who know me… in the biblical sense?
So, this clubhouse “reunion” felt both welcome and weird. It would be a strange vibe. Yet, with a few butterflies, I was glad to be invited into their inner sanctum.
I walked in, and the men, standing around with mugs of coffee, stopped chatting turned toward me, and welcomed me. It was a moment, and there was some clapping. It embarrassed me, but made me feel welcome.
For the most part, the gentlemen were, well, gentlemanly. I mean, it’s a public space, and there are others there the men know socially and corporately as well as women golfers mixing about, so they maintained a a decorum we wouldn’t have had if, say, we’d been at the mansion. Master McKenna had reserved a side room for this, so there was some privacy, but the men remained properly proper. Mostly.
I was still in my Sunday-go-to-church dress, floral with eyelet lace trim, topped with a lavender cardigan. The men probably hadn’t ever seen me so prim, and someone said I looked like a librarian. I commented drolly, “I can honestly say no one has ever said that about me.” There was laughter, and it kind of broke the ice.
There are times when my way with words, my sass and wit, serve me well. Other times, not so much. On this occasion it came in handy, giving me the means to engage in repartee as a way of maintaining my confidence.
Coffee and croissants were provided in back, and Declan Reilly offered to get me something. “Coffee, thank you, black,” I said. It was nice to be served. Though there were two round tables with chairs, everyone remained standing, chatting in random conversations. It was a cocktail party without the cocktails.
Mr. Garcia explained, “We don’t start drinking until noon,” as if that was some moral high ground.
Chaz (Charles Jenkins) quipped, “If we did, we would triple-bogey every hole.”
Gerald teased, “Of course, Mark does that even when he’s sober.”
McKenna grinned widely, and everyone chuckled.
Like that, the group engaged in good-natured ribbing, shots fired across the bow at each other, but I could feel friendly warmth among the men. I had seen this before when they have been at the mansion, but now it affected me more because of what I now am to them. It made me feel secure, not only in th experience of the full group itself, but with each of the men individually. They respected each other, and while I was merely the escort that I was to them, they included me in their mutual appreciation.
Indeed, there was no open, explicit chatter about my sexual experiences with them or about my escorting services. If there had been, I’d handle it in some way, but there wasn’t, not in front of them all together.
Yes, at times one or another would pull me aside to talk with me more intimately and would refer to our time together, recalling something of our shared sexual experience. But that was done with me warmly, even nostalgically. More on that later…
For me, one oddity of this occasion at the club was to stand among multiple men who each have had me in bed. A traditional escort has repeat clients, but she doesn’t socialize with, say, six of her former clients all together at a public mixer. This group thing was a rare and strange dynamic.
Part of the vibe I felt was about each of the men knowing I have slept with each of the other men. They were all aware that the others have had a similar intimate knowledge of me. To put it bluntly, each knew that the other men have likewise pleasured with my breasts, explored my pussy, and, just to say it, entered my vagina. I knew they each were thinking of me, at least some of the time, in those very sexual terms.
Further, I was sure they have talked among themselves of their experiences with me, compared notes. It’s what men do, or so I assume, at least in regard to a woman who has this designated purpose with them. Indeed, I knew this for a fact — in my times with them, some of the men requested things they only could possibly know from another’s experience with me.
This felt a little embarrassing to me, so I was lightly blushing much of the time. Yet I managed to assume an acknowledgment of what I am, suggesting socially that I am well aware of their sexual attraction to me and know my erotic affect upon them. Maybe it’s the only way a woman can survive in an environment of dripping testosterone — to use it for leverage. To be clear, this was real for me, not acted or reached for. However, it was a choice I made — to confidently “wear” what I am to them as a woman of their desire.
I’m probably making too much of that, but it was very much my swirl of feelings that day at the club.
Another choice I made ahead of time was to connect with each man individually. Call this “escort networking” or “client cultivation,” if you will, but it’s not disingenuous on my part, for I really do care about each of the men. Also, I figured my best way of coping with the whole group of men socially was to connect with each of them personally.
All to say, as the men had their own side conversations in twos and threes about their golf games, about business matters, sometimes about mutual friends, I prompted a few private chats on my own.
Mr. Garcia, one of the men I have not yet been with, had heard me say I had come to the club from church, and he was curious about that. I think most of them find it unusual that I go to church, being of the lifestyle I am and doing the escort service I do with them. But it seems Mr. Garcia attends church too, and we wound up in an interesting conversation about, of all things, faith versus morality.
Circling over to Declan (Reilly), I asked about his family, how Aiden was doing in college, and also about Barbara. I know more about Declan than any of the men there, even though I have not “been with him” yet. I will have a busy summer with Declan and, now it seems, his wife Barbara.
In conversation with Bill (Holt), we talked about his recovery from divorce and moving on from his ex-wife. Those details will remain private here, but he is doing well in that regard. He continues to say his time with me was notably helpful to him in that way. Which thrills me deeply.
Occasionally one or another of the men asked if I wanted something from the snack table or from the bar. I felt they were serving me almost as a kind of royalty. I remember thinking, This is what it feels like to be a courtesan in a royal court. It felt nice, warm, even if I knew they were taking care of their woman of pleasure.
But, as I alluded to, the gentleman were gentlemanly… mostly. Sometimes with me privately the men were more explicit. This never felt crude or rude to me, although it was pointedly sexual.
In a side conversation, Gerald (Bauer) whispered that “next time he had me” he would want me to wear this same “librarian outfit, because it’s really hot.” I remembered from our time together how he seemed to embody both romantic grace and a kind of wolfish libido. I teased him, “Gerald, I dress like this most Sundays. You should come to church with me sometime.”
Privately, Chaz (Jenkins), referring also to my demure outfit, compared that to the morning I came to his hotel room door perfectly naked. I blushed but managed to reply coyly, “Chaz, had I known that was your request for today, I would have accommodated you. But you never asked. I’d say that was a missed opportunity for you.”
So, I was able to respond in kind, dish it back to them in good humor, assuming my “sexual royalty” among them — again, my sass and flair coming in handy.
As the men came on to me in private sexual talk, I sensed some were actually reminiscing about our time together. Even their explicit language felt to me like they were saying it as a warm, nostalgic memory. And I could honestly respond in a similar way, for my intimacies with each of them were something I too enjoyed and remember fondly.
In some cases, I sensed these verbal intimacies were a way of confirming that I remembered them in some specific experience. Gerald was like this with me. He had me almost a year ago now, such a long time since, and I think he was testing me to see if I really remembered our experience together — or was he just another “client” among many? He mentioned the hotel we had gone to but left his comment open-ended, as if to see if I would fill in some of the blanks. I did, mentioning his colleague by name, whose retirement dinner was the occasion for our date together. I stood close to Gerald, put my hand against his chest, and said, “You know, Gerald, what I cherish that night is you and I dancing. I haven’t been dancing since.” Which was true. His face lit up.
A couple of the men anticipated my next courtesan engagement with them, saying they wanted to do this or that with me next time. Alan (Devers) asked me if my “escort services included…,” and he proceeded to list several “activities” he had been considering. I have not written yet about Alan, but he treated me literally as an escort-whore for hire. So be it. Even among the men at the club he seems aloof, although he connects well with Bill Holt. (But everyone connects well with Bill.) Here he was asking about my “menu of services.” I answered Alan, affirmed his lust list, and added with a wink, “Now I have something more to look forward to next time, Alan.”
I didn’t get much reaction. That’s who he is.
Meanwhile, Chaz was enjoying my sass and spunk. In one of his teases, he led me on, commenting, “When we were together, I don’t think I played with your tits nearly enough. I’ve made a note for next time.”
I replied, “They’re glad to hear that, Chaz… they’ve missed you.”
Part of the unusual dynamic of being an escort is that you are “suddenly sexual” with a stranger. You move from “What kind of business are you in?” to “How do you want to fuck me?” in ten seconds.
I have experienced this with four of the gentlemen so far, meeting them for our date early evenings and finding myself in bed with them later that night. Those men are no longer strangers, now lovers of a kind, and it will be interesting to see what kind of experience our “second date” becomes.
But two of these men I hadn’t slept with yet. Being around them Sunday made me feel that anticipation of soon being “suddenly sexual” with a stranger.
Of course, Declan is not a social stranger to me. Still, the kind of acquaintanceship I have with him is “friendly distant,” as if he is like someone else’s uncle whom you know from family BBQs and would never imagine having sex with. Although now with Declan I do, and being around him that Sunday, I felt it. This was neither dread nor eager anticipation, but my physical response to the realization of our soon destiny together. From a couple of things he said to me, I think he felt this too.
The other man I am still a virgin to was Mr. Garcia, whose divorce process has seemed never-ending but now is final. This social outing at the club allowed me some good time to chat with him and get to know him a bit better. I like him, and I look forward to being with him soon.
Generally, I have been thinking of my courtesan services as “dates” with each of the men, which they are, kinda. Thinking of being on “dates” with Mr. Reilly and Mr. Garcia makes it feel more normative to me. If I were truly in a vanilla life, any date I had with someone I just met would be “a date with a stranger.” So I tell myself. These are the mind games I play in my head. They help me feel less promiscuous.
Then again, with these men, I am a “date with benefits.” And more — I am with them for the purpose of those benefits. So, it still feels odd to think of myself with either of these men in bed. Not because they are undesirable but because they are strangers.
But that’s what it means to live the life of an escort.
The men decided to play another nine in the afternoon, and they took me out on the course to the first tee. They thought it would be fun to provide me with my first golf lesson, and they each took turns trying to tutor me. Of course, they had no interest in improving my golf swing but a lot of interest in putting their arms around me in the process.
It became feel-y and hands-y, and they had their (rather juvenile) fun. Inevitably, men become boys at times. I went along with it, serving dollops of my sass and snark.
Gerald was wrapped around me, trying to hold my body still, keeping me in proper posture as I swung the club. I quipped, “I’m getting the hang of it, but I don’t understand how it improves my shot for you to fondle my breasts while I swing. Is that how it’s done?”
Chaz, pretending to be earnest, explained in detail how having someone hold my tits was “absolutely key” to the whole technique.
“I didn’t realize that golf was such a couples’ sport.”
“Oh, yes,” Chaz went on in playful seriousness, “like in tennis, doubles.”
“And I suppose you’re willing to give me lessons.”
He grinned. “Of course.”
Bill said that I needed to get myself proper golfing clothes. “That’s part of your problem — your outfit is restricting you. You’re overdressed.”
I replied, “If I had a dollar for every time I was told that…”
Laughter. And more teasing fun, which I took in good stride. It was suggestive, but playful, men acting like boys with a MILF-y girl like me.
I looked over at Master McKenna who stood in back of the circle of guys. He was smiling, and as his eyes found mine, I could feel his approval. Among his closest friends, I had done well this day.
But I was terrible at golf. I admitted this to all of them, although it was already patently obvious. Gerald joked, “Good that you have a day job — or should I say night job.”
Bill added warmly, “And you’re very good at that.”
I left shortly after, letting them have a proper golf game. Without distraction.
I drove away thinking about my very odd life. I keep trying to knit it together, my submissive life and my courtesan life, two different things, yet quite symbiotic. I am a courtesan/escort by submissive obedience to the wishes of my owners. Of course, they wish this for me in part because they know this kind of sexual service fulfills me. They know I want this escort thing but cannot on my own give myself into it. So they “make” me do this thing that I cannot personally conscience — yet feel is oh-so-right for me.
And so, I found myself on a Sunday afternoon in the circle of men whom I am servicing sexually. I stood in a social mixer of respectable conversation in an elegant setting. It was an odd but warm, affirming experience, and I felt like I was a real courtesan in a kind of American royalty.
More and more, I am accepting that this is what I am and do. And on this particular afternoon, I found myself appreciated for it.