Tuesday, December 5, 2017

Sugar Couple Journey: Just the Two of Us

Rose texted me early yesterday morning to tell me that she had gotten her period and was out for our date night. She wanted to reschedule for the following week, but our kids have final exams next week, and will be home studying every night. I let her know that DW and I were bummed but that we fully understood her wanting to cancel, particularly since her period was painful on top of happening at an inopportune time. I let DW know and she suggested some alternatives, but nothing was working other than perhaps a night during the holiday break when we could send the kids to their grandmother's house for the night (with the dog, dammit!). I told Rose that we'd get back to her, but we haven't yet decided on anything. I even briefly thought of suggesting we try to hit up Missy for a last minute date, but I decided against it.

Still, DW texted me, "We could still have some fun naked time tonight if you're up for that." And why would I ever pass up a chance to make love to my wife?

After getting the kids out of the house for their evening activities, DW came back home and we just sort of relaxed a bit, taking care of a few things, before I just walked into the bedroom and told her I was dimming the lights.  I actually changed into my pajamas, but she got into bed fully clothed -- I could see her sweater. We watched a documentary that was very interesting, holding hands under the covers and petting the ever-present pooch between us.

After about an hour, however, I wanted to play, so I started gently coaxing the dog to move away so I could get closer to DW. I reached for the button to her jeans, but found her warm skin instead.  Peering under the covers to confirm what I suspected, I laughed and said, "Hey, why didn't you tell me you were naked down there?" "You could've found out yourself at any time," she said. "I was expecting you to be your typical hands-y self."

Encouraged now to continue, I kissed DW and sat her up to remove her sweater and bra. She also wore a camisole underneath and I left that on because it was black and sexy against her pale skin. In the moment, I got an idea: "Hey, you wanna play with that vibrator that Rose gave us? It'll be like our way of including her tonight." We hadn't ever used it since Rose came over, and it sat nice and clean in the cute box it came in. "Sure, OK," DW said. I sat up, took off my clothes, and got the vibrator out from under the bed and the lube from my nightstand drawer. I tested the vibe to make sure it worked.  It had seven speeds and a little LED light in the button to see it in the dark. Pressing the button for two seconds turned the thing off.

I set it on the lowest speed and traced the inside of DW's thigh, slowly inching it toward her pussy. I got in on her clit and held it there. She looked at me with an almost-imperceptible look of "wow" in her eyes and said, "Hm, that feels kinda nice." She took my hand and moved it so that the vibe was where she liked it. "I'm enjoying this," she said. I pushed the button and turned up the speed. "Is that second gear?" she asked, opening her legs a little more. "Mm hmm," I replied, kissing her deeply.  She pulled her top up over her breasts, and started stroking them. Who the fuck was this woman? I asked myself. She never touched herself like this. I wanted part of this too, I decided, and I put the vibe in her hand and suggested she try it out herself. She promptly went into third gear and started rubbing it between her labia and rocking her hips, a telltale sign she was turned on. I pinched and sucked her nipples, something she would normally stop me from doing, but she let me do essentially anything I wanted.

I got up and knelt between her legs, massaging her thighs. She put the vibe on my cock, but I told her that vibrators don't really turn me on.  It wasn't really true: I love ass play with a vibrator, but I wasn't ready for her to do that to me. This was all about her!

I got the lube and put just a little on it and her lips, then took the vibe from her and twisted it around, back and forth, up and down. With her hips rocking more assertively now, I knew it wouldn't take long. As soon as I saw her eyes roll back in her head, I knew she was going to come. "Take it easy, baby," I said, "breathe through it." I wanted the orgasm to kind of roll over her whole body like a wave of warm water, rather than just a quick jolt. But it was too late. Her entire body tensed up and she came really hard. From my angle I could see her pelvic muscles contracting. Fucking turned me on!

I just dropped the vibrator and got between her legs, kissing her all over.  Then I lubed us both up and entered her missionary. It wasn't easy, but I got nearly all the way in, deep enough for it to feel good for both of us. She said it hurt just a little, so I pulled almost all the way out and dropped a little more lube on my cock. That let me slide all the way in this time. It didn't take all that long. Don't know what it is, but having sex with my wife never lasted as long as sex with other women.

Afterwards, I snapped a selfie of us in bed. "No, no, don't do that," DW pleaded.  But I did nothing with the pic right then at there.  We just cleaned up and held each other for a few more minutes before I had to go get the kids.

While in the car, I texted the pic to Rose and said, "Wish you were here!" and thanked her for the vibe again.

I'm really glad we did that, just the two of us. We need to do that more often.


Monday, December 4, 2017

Sugar Daddy/Couple Reader Feedback

My last post generated some dialogue!

First came this from one woman:
I was thinking this with the other post: why not have another man? Give her that at least since she has to have another woman with you. It still sounds like you’re more fixed on your own sexual experiences and getting what you want versus what she wants. You guys should have another guy with you as well. Doesn’t seem fair. Or, let her have another male partner.
I responded with this:
[M]y wife has expressed very little to no interest in having sex with other men. I know she brought up the idea of being with another couple, but she is not serious. You don't have to believe me, but that's the truth.
On the other hand, she wasn't serious about threesomes and look where we are. I just think that the couple idea is something to revisit at a later date. Intercourse still hurts her, she's not skilled at oral, and her interest in sex is only just starting to expand. She's still way out of her comfort zone, but if she were to become far more comfortable (and skilled in bed), I'd be open to it.
Then another woman reader wrote this:
I agree with [the first commenter] about you seeming to be more fixated on your sexual needs. I was listening to the Savage Love podcast and a caller had a question about threesomes (he was married and was about to have his first threesome with his wife mww). Dan suggested that their first couple threesomes should just be focused on his wife....make her the star. He said it takes awhile for some women to feel comfortable watching their husbands fuck another woman. That made me think about you. I'm just suggesting that maybe you could try that. 
Also...I agree with you. Your wife is no where near to exploring sex with another man...not yet. I just think that if the focus is mainly on satisfying her it may help. 
I'm sure it's very difficult for her to watch you fuck another woman.
I truly appreciate both these comments.  Here's what I have to say to the second commenter: For most of the first hour of our first threesome with Rose, we (mostly Rose) were 100% focused on DW. DW was lying naked on a massage table while another naked woman was putting her hands and mouth all over her body -- on her breasts, between her legs, and inside her. This was a deliberate choice Rose and I made ahead of time to make sure DW would get comfortable with this level of sexuality with a woman. If it didn't go well, I was prepared to stop the massage and send Rose home, and that may have been the end of our poly-lite experiment. This was also something I discussed ahead of time with DW.  However, she was all in and fully engaged after that hour, and when things started to turn into a true threesome, I had to slow DW down because she "wanted me to feel good too." As if watching my wife be pleasured by Rose was just meh! As if my throbbing erection at watching this scene was just a coincidence! The longest stretch of time during the three-way sex was my having sex with DW, not with Rose.  And while I was inside Rose, Rose was going down on DW.  DW was most certainly the "star" of our first encounter. Given the fact that she had her period while with Missy, and even though I suggested rescheduling, DW agreed to participate minimally. In hindsight we both  realized that we should have postponed until she could be a full part of everything.

What I'm stressing here is that DW is a full participant in this whole process. The reason why these two readers might be getting the impression that I'm mostly fixated on my own sexual experiences and/or feelings is because, well, this is MY blog, not OUR blog. Of course, it's all going to be from my point of view. Quotes in my posts are accurate, and when they express their feelings I relate them accurately in my writing, but a lot of the time I'm interpreting from my own perspective on the situation. That's kind of unavoidable unless I'm actually interviewing them before, during, or after a particular date. 

As for DW's feelings about watching me fuck another woman, it definitely started out that way, but the discomfort when with Rose morphed into feeling left out when we were with Missy. Now, she says, she's pretty good about it so long as she gets to fully engage with the girl. We'll see how all that goes this week when we see Rose again.

With respect to these readers, a little slack would be appreciated. This is all very new to me and to DW, and we're still learning our way through this. 

IN OTHER NEWS...
I've been asked to be a guest on a podcast about sugar dating. More to be revealed once the details have all been nailed down.



Wednesday, November 29, 2017

Sugar Couple Update: Marriage Counseling Worked!

From my last post, readers may interpret that the whole sugar couple arrangement is in trouble. While DW and I definitely have a disagreement over the money aspect, something that will continue to be discussed and/or debated in the ensuing months, I think it's pretty clear that DW is not ready to give it up yet.

With the kids away at their evening activities, we spoke before heading out for our dinner date. I suggested that before we really got into it, that we spend a few minutes just connecting with each other, the same way we did week after week while in therapy. So we sat next to each other on the couch, holding hands and looking at each other, catching up on the day's events and just checking in with overall feelings. When that was over, DW spoke first. "I'm really pissed at you," she began. Uh-oh, I thought, incoming! 

"I told you that I was willing to give Missy another chance, and I meant it. I was open to playing with her again. I like her, she's beautiful, she's really sweet, and I felt like I was more comfortable than my first time with Rose. But you came in this morning and said, 'I'm cancelling tonight' like only you had the authority to do so, without consulting me about it. I am really out of my comfort zone here, and I'm doing this willingly. I'm having sex -- with a woman -- and talking about things I've never fully been comfortable talking about.  And now, Missy may not even be interested in seeing us again."

It dawned on me that she was looking for some validation for her stepping outside her comfort zone and doing things she has never done before. So I began with that, honoring her for being brave and open and trying new things as a way to create more trust and intimacy in our marriage. But I then zeroed in on my concerns. "Based on the two encounters we've had, I suspect that what you liked most out of them was not having sex with these women, but having sex with me. Incidentally, that was my favorite part too. I really enjoyed having sex with both of them, but really I was just so happy that you and I got to make love -- got to fuck -- after all this time. And I want more of that too."

"So do I," she replied.

"I'll definitely be mindful of my tendency to be authoritarian, particularly around this," I said. I also told her that Missy was understanding and hopeful to see us again, and that Rose had agreed to see us next week.  This made DW happy because she was looking forward to another hot massage.

We got on the topic of money again. "I just wish," DW said, "that we could find someone who just wants to get together for the fun of it." I agreed, but added, "You have to remember that I didn't just come up with this sugar idea out of the blue. I looked around for a long time to see what would work best -- for me at first, but I also thought about us later. The sugar arena is the best, quickest, and most common way to find a companion for us. But don't just take my word for it. Go -- with the free time you have (note: she has none) -- and go look for a woman who wants to meet a couple for sex just for the experience of it. I'll even find the websites for you. The sugar culture has pretty much permeated every aspect of casual sex that you will have a very hard time finding someone right away who is attractive to both of us who doesn't want money."  I added that there were ways to re-frame the money we were spending, but I didn't specifically say that it was about an investment in our marriage. I just let her take it in. 

We also touched on the topic of perhaps finding a couple to play with, but I was, at least for now, against the idea. "If we meet a couple we want to play with that might be fun, but only if you're willing to have intercourse with the guy. And you're not really there yet. And besides, the woman has to be young and cute, so we'll be limited to only certain kinds of couples." I left out the part where she needed to be better at sucking cock, but that's eventually going to come up too.  She agreed to table that discussion for another time.

By the end of the conversation, we agreed that we were excited to see Rose again, and probably would go with her over Missy, but that we still wanted to see Missy again to be sure. I couldn't help but smile to myself. My wife was thinking like I did as a sugar daddy!

We had a nice quiet dinner, free of financial stress, free of concerns about the kids, but definitely with all of the things we have going on in our minds.

That night, DW had a hard time getting comfortable and falling asleep. Like I frequently do, I said, "How about I eat you and make you cum? You always sleep better that way." To my great astonishment, she agreed, and in less than five minutes she had a fantastic orgasm under my tongue. I think she's getting to know her body better! Immediately she rolled over and fell asleep, leaving me to take care of my now-hard cock.

We both slept really well that night.



Monday, November 27, 2017

Post Holiday Skids

The Thanksgiving holidays at our house always leave me feeling great. Family from both sides, including some beautiful kids, and some close friends, all feasting on great food we all prepare and bring together.  We had two dozen this year, a little smaller than usual, but still a crowded house.

DW and I were optimistic about seeing Missy again this week, but that has ended as of this morning. All weekend following the holiday, whenever I brought up that I was excited about our date, I'd see DW's face covered with an obviously forced smile. Finally, I called her on it: "You aren't into this, are you?" I asked.

"To be honest," she said, "not really." She explained that she was having a hard time getting over the money we were spending on it and couldn't separate it from what she felt was prostitution. Definitely it explained her reluctance to discuss any of this with anyone. But I felt it went deeper than money. I believed she didn't really care for having sex with women. Which was understandable and perfectly OK, and I told her that. She stepped gingerly around the issue because "this is something that you need." I asked her if she preferred Rose to Missy, and she couldn't really answer. "I really like both of them," she said. "They're both beautiful and sweet, and I can't really say that my enjoying Rose more had to do with the fact that I was on my period with Missy and couldn't really participate." She said she was willing to give Missy another chance.

But I had my doubts.

As I saw it, it was a lose-lose for me if we gave Missy another shot. If we went ahead with it and she didn't enjoy herself, we'd be out the allowance, and she's already seriously conflicted about the money. If we didn't go ahead with it, she'd be upset that she didn't get her second chance and she'd also be stressed that I'd be foregoing what I wanted because of her.  I'd be on her shit list either way.

As we woke this morning, she was in the same place as she was the day before and the day before. I assured her that we could cancel today if she wasn't in the mood and maybe see if Missy were OK with another delay. "But that's not really fair to her," DW said.

"I know," I replied. "I fully expect her not to respond if we cancel today. I probably wouldn't if I were her."

I also suggested I reach out to Rose to see if she were available on short notice. This seemed to interest DW somewhat.  I then told her I was canceling with Missy.

After dropping my older kid off at high school, I drove back home and sent Missy the text: "DW woke up today in a really funky place this morning, and not at all in the mood to play tonight. I know this is an arrangement and that this isn't fair to you. I'm not sure what else I can do except support her. I hope you can understand. Please forgive the short notice." After sending that text, I let DW know by text and she replied, "OK."

As luck would have it, DW and I had a couple of minutes at home before we headed off to work. She was not happy that I canceled with Missy. "I was willing to give it another chance," she said.

"But you're not in a good place, baby," I replied. "And if you're not in a good place around it, I'm not gonna be able to enjoy myself either."  I also said that I was willing to put it off for that reason alone. "It's gotta work for both of us," I said.

She admitted that she's not sure she's interested all that much in sex with women. Which is what I suspected all along. But she's still mad at me for cancelling with Missy. I think she didn't like that I told Missy some of the truth about why (I didn't address her hesitation around money or around sex with women, just that she was in a funky place around getting together today).

The discussion deteriorated into a bit of an argument, and it's definitely something we'll have to address later while the kids are out.  We have a date night tonight, and I plan to honor it regardless of whether we're having sex or not.

My doubts were confirmed 100 percent. It's a no-win situation for me, and if I'm going to lose, I might as well take the loss that doesn't also involve the outflow of cash she feels is paying for prostitution.  I'm not entirely sure how I can help her overcome that bias -- I've thought about suggesting that she see this as more than about paying for sex, but investing in our marriage, but that feels a little patronizing to me.

On my way into the office I explained how I thought that either choice put me in a bind. I meant that sincerely and that I would rather err on the side of caution and put it off until we connected about it.  Her response was very telling and further confirmed that what I believed was right on:
I don't see you in a bind either way. I don't know where your head is at. I guess I don't understand. I said I would give it a whirl again because I had my period last time and I meant it. I made a promise to you and I said I would do it all, though I have always been upset about the money. That is not the issue here. I was upset about that before we even started and you knew about that and we talked about that at length when we were in counseling. So please don't use that as an excuse. You would have had a lovely time screwing your little Asian petite woman whether I had a great time or not. I was open and willing to try. And who knows, I might have enjoyed it more later.
If that little highlighted part doesn't give her true feelings away then I'm an idiot. And I am not an idiot.

The good news is, DW and I are getting more intimate in multiple ways, and that feels right. If I have to take a little time off from the extra stuff for a few weeks, that's OK. I answered this text very carefully, thanking her for sending it and saying that I would refrain from commenting "because context is important and I don't want to misjudge what you're saying. I am happy to be with you anyway and I think we should spend some time together tonight."

She replied, "Agree 100%." I was 100 percent right.

Stay tuned.

Tuesday, November 21, 2017

Sugar Couple Update: Messing Around With Missy

It's been more than a week since DW and I hooked up with Missy. I know you've all been patiently waiting (some of you less so than others lol). I remember only a few details, while the rest has become fuzzy. This works for me, though, because I'm more interested in the things I've learned than in the things we did.

Missy showed up on time (early, actually), and came to the house wearing a short sweater dress that showed off a good amount of leg and cleavage. She also wore some fierce heels that DW noted to me later were Jimmy Choos. "Someone's got some money to buy her those shoes," DW said the next day, winking.  When she stepped out of them, I noticed she was just an inch or so taller than DW.

We shared a glass of wine in the living room, making small talk. After about half an hour, however, when the talk turned to the ladies' complaints about their jobs, I knew it was time to adjourn to the bedroom.

Missy disappeared into the restroom for an inordinately long period of time, so DW and I just curled up on the bed, fully clothed. "What if she comes out naked?" I asked. "Well, I guess we get naked pretty quickly too," DW said.

Missy emerged fully clothed, which I liked, because I wanted to slip her out of that dress, and did so in short order. I also got DW out of her clothes as well until we were all down to underwear. Kissing began softly. Missy has very soft lips and a gentle tongue, which I prefer to all that hardcore face smashing and tonsil hockey.  She and DW were also very gentle with each other, and I could tell DW was a little more confident in how she handled herself since being with Rose. Unfortunately, because DW got her period a few days earlier, her participation would be limited, but I think we all took full advantage of each other! 

Basically, I had sex with Missy in front of DW, while DW joined in where she could -- to suck my cock a bit, play with Missy's breasts, and stroke herself now and again.

I should pause to note that Missy's body -- I just don't have the words. "Curvy" seems inadequate.  "Busty" is, well, meh. "Flawless" is misleading because everyone has flaws. She had porcelain skin, large, soft breasts, a small and round booty (for an Asian who typically have flatter butts), and legs for days. I thoroughly enjoyed every minute I spent with her.

After we went down on each other -- Missy's very gifted with her mouth, and I nearly came once -- I entered her missionary before switching to her on top, facing me. It's my favorite position and almost always makes me come, but I guess I'm still getting used to a few things. First, wearing a condom. I only wore a condom once with Mel, and once with Aussie. I used them with Chic, but I can't remember how it felt (oh yeah, now I remember!). Second, having sex with someone while DW watches me. I guess I'm still processing it and wondering how she's doing. I don't want to stop mid-fuck to check in with DW, but I guess I did it anyway, by leaning over to kiss her, tell her I love her, bring her into the action.

I got winded too soon. Man I have to get back in shape!  Missy offered to suck me off, so I took her up on it. A very sloppy blow job with great hand action, but still no orgasm. I took hold of my slick cock and stroked away while Missy kept the head in her mouth. That worked, and I unloaded so much it spilled down my shaft and all over me. I have no idea what DW thought about that, but she said nothing then and nothing since to suggest she didn't enjoy herself.

After about an hour of hanging out, we dressed and she left, but not before making our next date for next week, and talking about meeting up during the holidays on a weekend.  Ironically, Rose texted me while I was fucking Missy and asked about getting together too. I knew DW and I would need to have a conversation later about that.  As we were walking Missy to the door, DW looked at me and whispered, "The money, the money!" "Oh, yeah!" I said, and ran back to get the envelope. "I guess we had so much fun, we almost forgot this!" I said, slipping it into her purse and giving her a sweet kiss goodnight.

It took until the weekend before DW and I could find the time to be alone and talk about our experience. "She's very pretty," DW said, "and I like how sweet she is." "Do you prefer her to Rose?" I asked. "I don't know, because I didn't get to do all the things with Missy I did with Rose. I really enjoyed the massage I got with Rose, though." I said that it was clear to me that DW needed a lot of foreplay to get in the mood. She wasn't sure, but I was. "I'm fine with whatever you choose, baby," I said, "they're both great girls, but it's all about your comfort for me." DW didn't really want it to be all about her, but since she was the newbie among the four of us, it was important that we pick the right girl for her, not for me. We'll see Missy again so that DW can enjoy her fully, and we'll see Rose again next month as well.

Wow, I guess I took longer to describe what we did than I expected!

The lesson I learned here is about how absolutely, goddamn lucky I feel to be with a woman like DW. Her courage in taking this step into an arrangement and exploring her own sexuality with women is inspiring to me. I truly wish I'd had the courage to step up and insist on what I wanted when I first set out to do this nearly ten years ago. Maybe those years wouldn't have been so fraught with tension and resentment and depression. I could have avoided all the drama with C/Hayden, Jade, and Leah, none of whom were bisexual anyway. Had I been able to find a partner like Audrey from the get-go, maybe DW would have opened up sooner and a fully polyamorous relationship could have been created. Well, coulda woulda shoulda, right? It doesn't matter. My journey happened for a reason, and I accept everything that has happened since the beginning. I can't guarantee that DW wouldn't have freaked out if I'd insisted on open marriage, and I could very well be a single man right now.  So... acceptance (breathe in, breathe out).

The last thing I want to note is how stunningly beautiful my wife is. She may be north of fifty years old, it may show that she carried two babies in that little belly of hers, and her hair may have gone fully grey at this point, but having her naked next to two other women in this past month has proven to me what I've said since the beginning:
I am truly, madly, deeply in love with my wife, and am still wildly attracted to her.  She may be in her forties, but she takes great care of herself and is simply the most beautiful woman I've ever known.  I get instantly hard when we snuggle close in bed (often, much to her dismay). 
Missy may be in her mid-thirties, and Rose in her early thirties, but they would kill to have a body like DW's when they reach her age. Her skin is soft and smooth, her lips still soft, and her body is firm exactly where it needs to be. In fact, she's in much better shape than Missy is at her age.

Just feeling a great deal of gratitude right now and I wanted to share it.


Wednesday, November 8, 2017

Sugar Dating Validates Feminism

I'm going to get a little political with this post, so please bear with me.

A profoundly moving op-ed piece in today's New York Times, written by author Lindy West, is titled "Brave Enough to Be Angry." The piece centers around the surge in female anger around the way men have diminished, demeaned, and discredited women who have stood up for themselves against abuse, violence, and harassment.  The piece contains the following brilliant observation:
I did not call myself a feminist until I was nearly 20 years old. My world had taught me that feminists were ugly and ridiculous, and I did not want to be ugly and ridiculous. I wanted to be cool and desired by men, because even as a teenager I knew implicitly that pandering for male approval was a woman’s most effective currency. It was my best shot at success, or at least safety, and I wasn’t sophisticated enough to see that success and safety, bestowed conditionally, aren’t success and safety at all. They are domestication and implied violence.
I emphasized that part in bold to point out that it doesn't really matter where a woman is in her life. She could be a college student, an entry-level clerical worker, or a restaurant hostess, or a mid-level manager, or a state legislator, or even an entrepreneur/CEO. A woman's most effective means to gain traction in a male-dominated society is her looks and her sexuality. And, unfortunately, because of the fact that men dominate the landscape, looks and sexuality only go so far, and not even talent or wisdom or political or business connections are guaranteed to help. In fact, sometimes they can even hinder a woman's advancement because of the threats they pose to the male-dominated paradigm.

This dynamic doesn't disappear in the sugar dating environment, either. Plenty of women I've met and talked with over the years, including women with whom I've been intimate, have described instances where men took advantage of them by using their power and/or their money as tools. I had to go back and look at my own history as described in this blog to check my own behavior to make sure I'm not fully guilty of the same level of abuse. I'm happy to say that I've been pretty good about how I've treated women on my journey. I have definitely been angry with a number of women over the years, but I've never used my position (such as it is) to belittle any of them. Most of my anger has been in response to some perceived (or actual) disrespect I've received: Jade's lying, Leah's manipulation, or Red's handling of my financial counter-offer. I took advantage of a couple of women early on to sleep with them without an allowance (Lina, Katie). I slept with a few knowing I'd only see them once, rather than eventually discovering we weren't a good fit.

Where I see sugar dating as a validation of feminism is in how it democratizes the relationship. It "levels the playing field," as it were. Men and women in the sugar community know that there is a knowing exchange between parties that are of equal value. Sure, men (including me) do try to get away with as low an allowance as possible, but there is no manipulation involved if a woman consents to the allowance. It's presumed that she's deliberated her circumstances and decided to accept what the man is offering in a fully informed way. I won't deny that there are exceptions to this, but my take on it in general is that it's a very fair dynamic.  Women feel empowered that they are in charge of defining their value and they have full agency over it. Men who try to violate that quickly discover that they're not going to get laid anymore, so the vast majority of the time, they behave themselves. 

Of course, I don't deny the existence of the fakes and flakes who tend to clog up the sugar website. I remember porn star Kyra's sorry tale of being shorted her allowance.  But again, those are exceptions, not the rules.

Far more often than not, I've heard stories from these women who say they felt like an equal, like a partner, and highly appreciated by their "daddies." I would say that the sugar dating world is one of the only places where a woman can use her most effective currency and be well rewarded for it. On reflection, I think it may even be one reason why I kind of dislike the "sugar" terminology -- "Daddy" and "Baby" absolutely convey a dominant/submissive vibe, but I think those terms are more about the predominant age difference between the parties, and are attempts to be playful rather than establishing some sort of gender-based hierarchy. In reality, the dynamic is much more egalitarian and respectful, and forward-thinking.

Brandon Wade, the founder of Seeking Arrangement who basically invented the modern sugar dating subculture, put it this way in an essay he wrote for CNN in September 2014 (I was with Audrey at the time, engaging in swinging with other couples):
Traditional relationships are based on possessiveness and selfishness. As I look at the future of traditional relationships, I see divorces, heartbreaks and broken families.

But it doesn't have to be that way. By encouraging people to find and negotiate an arrangement, we hope to create modern relationships based on open-mindedness, open communication, brutal honesty and transparent expectations.
Here's somewhere a woman can ask for and get what she wants with complete honesty about how and why she is asking. As a man, I find that disarming but also refreshing. I don't need to do the dance, I don't have to adhere to traditional norms about relationships, and I get to find a partner who feels the same. That partner, amazingly enough, is my wife.  My DW and I nearly lost our marriage and our family because of adherence to tradition.  Now that DW and I are beginning to explore sexuality in this new way, I am literally thrilled at the possibilities.

Monday, November 6, 2017

Frustrating Delays

Next week DW and I were supposed to see Missy for our first time together, but we had to postpone it a week due to an event that we're obligated to attend. It's not an event that I'd normally ever want to attend, and since it was our date night I tried hard to figure out a way not to go.  But when our kids got home a couple of nights ago, we found out the that older one was participating in and leading a portion of this event. So, DW and I looked at each other and said, "Let's let Missy know."

I sent Missy a pretty generic text:
Hey, babe, how are you? So, I hate to do this, but are you available the following week? DW and I just got notice of an event we have to attend. We're so sorry because we have been so excited to see you and play together. Can you please let me know?


Missy was, luckily, available the next week, and she replied that she, too, was looking forward to getting together but "I understand."

It was the "I understand" part that worried me. In my mind, "I understand" conveys disappointment. Think of that TV show when the hero, who's been interviewing for that dream job, gets that phone call with the bad news that he didn't get it, and says, "I understand...thank you for the opportunity." You feel so bad for the guy, don't you?  Well, that's where my head went when I heard "I understand" from Missy.  If she had said, "Yeah, I'm available, it's no problem, thanks for letting me know so far in advance," that would have been cool and would have conveyed something much different and much less loaded, than "I understand."

So, that's when I clarified, and told her the full story. "I didn't really want to share all the details because they might seem manipulative, particularly because they involve our kids," I wrote. "Honestly, we would never have postponed unless we had a compelling reason."  I got no response, but didn't really expect one.

Now I'm in my head and I'm not sure she'll wait another two weeks to see us. I might not if I were her.

A similar thing happened with Toni, who had run into traffic issues a couple of weeks ago and had to postpone meeting us for drinks. As I wrote before, she probably disqualified herself, but I kept the door open just in case things didn't work out for one of the others (I am always, always hedging my bets). Now that things with Missy feel a little weird for me, I'm glad I hedged. Anyway, Toni returned from Hong Kong and then went to Las Vegas for business and pleasure.  Her Instagram was full of pics and short videos of her at various nightclubs (and always with those ridiculous Snapchat filters on her face). But a few of the vids were very sexy, and I told her so. She then texted, "So, should we meet on the 13th?" That was our Missy date day. "Maybe it's better we meet on the 6th," I replied, forgetting we had this obligatory event. "That works better for me," she wrote, "OK!" I told her I'd discuss with DW. Before I did, however, I remembered why the 6th didn't work. And an hour or so later I wrote, "Hey, DW just reminded me that we have a conflict that night. I'll have to get back to you on when we're next available."  Her answer? "I see." I think that's even worse than "I understand."  Not that I'm all broken up about it, but I really hate to be the bad guy.

Over the weekend, Missy and I have communicated a bit, and we're still on for next week, but my chief concern now is my belief that DW will get her monthly in the next week, which would make seeing Missy very problematic. If that happens, I'm hoping that DW will have learned to trust me enough to let me see Missy on my own.

Yeah, yeah, I know I'm probably insane for wanting this. But the upshot of it is that Missy will probably move on if we put her off again, regardless of the reason. Sugar babies count on us to be reliable, and cancelling is seen as a definite no-no. I had a chat with DW about this topic over the weekend, because she and I wanted to buy tickets to a concert and they were about $500 apiece, which is pretty damn expensive. DW suggested we forego getting together with Missy or Rose so we could go to the show. I said, "We might as well tell them we don't want to see them anymore if we do that. We've already canceled on Missy once, so if we do it again, she'll probably bail. This is an arrangement, and it looks bad for us not to hold up our end."  DW understood that but I still think she'd rather go to the concert.  But having had that chat with DW sort of makes it easier for me to broach the topic of seeing Missy on my own.  Long-shot, I know, but I'm not beneath taking long-shots.

POSTSCRIPT: our kid woke up sick today, so we aren't going to the event after all. Still have to stay home and take care of the kid anyway.