Monday, October 16, 2017

Sugar Couple Diary: Meet and Greet Previews

Tonight DW and I will meet two women as potential partners in our Sugar Couple journey:

Toni, who I profiled in my last post, is a late-20s, very tall brunette with blue eyes who lives about 45 minutes away. I first saw her pictures on Tinder, where she also included her Instagram ID. Sending her Direct Messages on IG proved to be very successful in reaching her. She has some very stylized photos of herself on IG, mostly featuring her lovely face with a bunch of Snapchat filters on them. I swear, the filters are so popular on the Sugar Daddy website that I almost want to ignore every one of them. Who can get a clear view of a woman's face with a bunch of bunny noses, puppy noses, or fake eyeglasses?  (OK, old man rant over!) In any event, she identified herself on IG as a "public figure" in the world of fashion, and included a link to her website. I visited the site to see if there'd be any normal pictures of her, and she's still damn cute, but she is a big girl. Physically, she reminds me of KC, who I saw about a year and a half ago right after my failure with Red. Later she posted a normal, full length pic of herself on IG, wearing a form fitting black dress that really accentuated her curvy body. She had a belly, but so what, I do too, and so does DW. Not a turn off, especially when the boobs are as luscious as hers. She will be the second of our two meets, which will happen one after the other. The first meet will be with --

Missy -- a mid-30s Asian woman whose pictures on the Sugar website show both fire and wholesomeness. She's got long dark hair, and lovely face and smile, and a body that knocks me out. "Well," said DW when I showed her the profile, "you wanted someone Asian, and she's certainly pretty." Missy is bi-curious and has had sex with women before, but prefers sex with men. Lucky me!  She seems open and nice, and works with kids like DW, so there will be stuff to talk about.

I set these two back-to-back meets in different locations about a block away from each other. We'll meet Missy for wine at one place, then walk on over to the other place for cocktails and appetizers with Toni.

Whom do I prefer? Definitely Missy, who's petite and Asian, but Toni seems a bit more open-minded and playful, which like as well. Her being taller than I am doesn't bother me. Wanda was the same height.  But it might bother DW. "Still," I told her the other night, "we're all the same height in bed, right?  At the end of the day, however, I think we'll end up with Rose.

So, I then had to handle all the others except Rose. Pettit is still on hold until next month, as is Taylor. Tika is pretty much out since I'm just not excited about her personality so far. Lani never responded to my reach-out, so she's out. There were a couple of others, but no one who wowed me or DW.

This morning, DW reached over and started stroking my dick. While she did that, I asked her what excited her about being with Rose next week. She said she didn't know, but I pressed further. "Do you want to touch her anywhere?" "Her boobs," she said, "she has nice boobs." That was true, as Rose had texted us a full-length nude selfie over the weekend. "I want a flat stomach like that," my wife said. "Me too, and we'll have it next week," I joked.  I asked her if she envisioned herself lying back against me, her legs open, while Rose massaged her pussy and I kissed her neck and stroked her breasts. She liked that! I almost came just envisioning it myself! I got hard just typing this! (I'm seriously in need of sex, man, and I'd like to have it this week. Any hot women reading this in SoCal should message me a guy out!)

More tomorrow after the meets.

Tuesday, October 10, 2017

Sugar Couple Reality: People Mostly Suck

Since last Friday's post, I've spent the better part of a three-day weekend looking at ads and checking out new girls for DW and I to fuck. In fact, DW is now at the point where she really wants to do it soon.  We've watched another threesome video, an episode of Tripl3 Play, which was more hardcore than the Toyride episode.  She just wanted to skip most of the video and get to the sex. Not all of it, however. "I like watching how they end up deciding to hook up," she said. She wasn't knocked out by the fake tits on the girl they chose, but it was a hot scene, which involved the married couple mostly fucking each other while the third got taken care of at the end.

Early the next morning, while DW was at the gym, I was on Tinder, and came across one woman I thought was smoking hot. One thing I've noticed on a lot of these Tinder profiles is that some of the women include their Instagram handles. After getting only one swipe right after six days of this, I decided that if these women were going to include their IG handles, then I was going to send them DMs and try to get their attention. So I sent this one woman, whom I'll call Toni, an Instagram message. "Of course I swiped right," I wrote. I got a big red heart in reply, so I pressed on: "What, if anything, are you seeking on Tinder?" "Nothing in particular," Toni replied, five hours later, "but I'm always keeping an eye out for Mr. Right. In the meantime love meeting new peeps, you never know! Or a sugar daddy, of course, cuz why the hell not? Kidding, haha. Thanks for reaching out."

Like I was gonna let that go without a reply. HA!

"Actually, I am a sugar daddy. I'm in a poly relationship and my wife and we do this together. No kidding." I sent a picture of us together to emphasize.

"What luck," she said. I gave her my number to see if she'd text me offline.  She then asked where we lived and whether DW was "all in, as I would never intrude."  When I told her DW was all in, I got another big red heart.

So began a conversation that has lasted three days, culminating in an agreement that this beautiful, tall (5'11"), late 20s brunette with the big blue eyes will be meeting DW and me next week for drinks.

A new WCSD Journal first!

I tried this one other time Sunday night with another Tinder woman, but it didn't go so well. It was about 2 am when I couldn't sleep. She took the bait and we had a 30 minute conversation, but I left off the sugar daddy part (she didn't bring anything like that up, and if I could find a partner on Tinder who didn't want any allowance, perfect!). She was skeptical from the get-go, and actually called bullshit on me. She'd sent me a connect request, but I didn't immediately see it (it was 2 a.m. for fuck's sake), and from that I think she doubted I was telling the truth. But I did let her connect with me once I saw it, and that allowed things to go on for a little while longer. At one point, however, she just threw up her hands and suggested that if I wanted a threesome it would have been better for DW to initiate it to make it more credible, otherwise I'm just some married guy lurking on strangers' IGs at 3 am. It didn't help that I said DW didn't have IG (who doesn't?) and that if she did connect with her it would be through my own IG.  I knew how it looked to her, and she was wrong about everything, but it sure looked creepy to her. I apologized and disconnected from her immediately.

There were a few more which I'll list here. All of these women are good to go with DW:
  • Rose: I've written about her before, and nothing's changed.
  • Taylor: very cute early 30s brunette, very slim. She has two kids, both of whom live with their father out of state (I avoided discussing that drama like the plague).
  • Tika: A half-Indian, half anglo, mid-20s, very sexy. Caught up to me while I was in the car with one of my kids. DW is reluctant due to her age and the fact that her pics make her look like a Kardashian, but she said yes.
  • Lani -- average looking blonde, mid-30s, with a very long nose and long face. I'm not knocked out by her, but DW liked the fact that she seemed real and natural. I gave her the details on getting together, but she never responded, and I think she'll be out.
  • Pettit -- see last post.

Postscript: You might recall posts where I was sure that Jade was going to become our partner. However, it didn't happen because Jade had to return to New York. That was more than two weeks ago. I put Jade out of my mind and started seriously working on Rose and others. Last week, however, I got a text: "Guess who's back in town?" Jade had resolved whatever issue had forced her to go to NY, and now she wanted to hook up with DW and me.  Now, my better judgment told me to keep that woman at arm's length, but I permitted some contact. I told her that we'd already talked to two women (Rose and RJ) whom we really liked, but if she wanted to be the one, she had to put a profile up on the Sugar Daddy website so we could find her and start a dialogue. I even gave her instructions on how to create the perfect profile that would wow DW.  You might have read that I'm somewhat of an expert on a great profile.  She enthusiastically said she would do it, telling me it was urgent because she really needed the money.  True to her character, however (or lack thereof), it took her until last Friday to get it done, and when I finally got the chance to look at it over this past weekend, it had exactly none of the things I said would work to attract DW's attention. She also lied about her age. Not a mortal sin (except for DW, who hates lying), but she also posted pictures of herself that appeared to show her even younger than her posted age. I thought she looked to be about 21 in her pictures. That would be a more than ten-year lie about her age.  There was no tattoo where I knew one would be, her eyebrows looked different, her lips, and her hair, all looked young. Finally, she said this would be a new profile, but the website showed that the profile had been up for at least a month prior to my asking her to put one up. So, again, she lied. My guess was that she was too lazy to make the changes I suggested and figured that she could use it for someone else in case we didn't connect. Fair enough, I thought, and I texted her to make the changes I suggested and I'd let her know when DW saw it so she could change it back. She promised she'd have it done by the next day.

The next day came and went with no updates to the profile. I sent her a text midday to find out what was going on. I was not happy and I had almost no patience left, but I was willing to give her another chance (like an idiot). She said, "Dude, I'm camping with friends. It's the weekend. Go enjoy your family." That was it. I was done, and I told her so.

"I knew you'd blow this too. Constant disappointment."

In reply came a picture of the desert scene outside the car window, along with a hand-waving emoji.

"'I'm broke as fuck,' you told me. 'I need this badly,' you said. I even gave you a way to do this so you'd WIN, but you went your own way, and you lost. Enjoy being out in that wasteland. Suits you."

"Ok," she wrote, "you obviously don't respect my time."

"You didn't respect my efforts to help you, and you again lied to me. Love ya, but you and I will never, ever work."

"Lie to you, or procrastinate?" she replied. "Listen I'm on a fucking camping trip on 'shrooms. You're ruining my weekend. We can talk tomorrow, regular human hours. Or not. I didn't mean to make you upset. I'm fucking tripping balls bro!"

She just couldn't help herself.  I laughed out loud. "Don't bother. You think I'm going to let a lying, irresponsible, drug-taking mess near the most precious person in my world? Into my home? You really are tripping balls, bro."

Yesterday I got a notice from the website that she'd viewed my profile.  I should have blocked her, but nothing came of it.

This morning, after having time to cool down, I permanently closed the door on an arrangement, but without being nasty and without saying never. Because how often has she come back into my life now?
"I hope you enjoyed your 'trip.' So I just want to be clear. If this were just me, I could handle being in an arrangement with you. But when my wife and I sat down and discussed the qualities we wanted in a partner, the top three were emotional stability, kindness, and financial stability. To us, this was the bare minimum we required to allow someone into our lives and our home. Unfortunately, you have none of these qualities, and the other women we've met have all of them. I've known this about you all along. I blame myself for not trusting my gut and considering you anyway. This is my fault. While this is very likely goodbye, I'm not throwing away your number, because you never know."


Friday, October 6, 2017

Sugar Coupling -- Starting to Normalize

Since the last post where I related the input of our therapist in the ongoing drive toward Open Marriage, my DW and I have remained focused on finding someone suitable. You might recall that we have three potential parters: Rose, RJ, and Pettit. Since that post, the traffic into our email inbox has been incredible, and other potentials have surfaced.  All have some appeal to me, and some to DW, but so far none has matched Rose for overall compatibility.

We could not connect with RJ, either in person or via FaceTime, as she is out of town caring for her mother who is recovering from a medical issue. We were scheduled for a FaceTime call last night, but RJ postponed it again due to privacy issues at her mother's house. We suspected she would do that, and so DW and I crafted a response. We said that we really liked her but that logistically this was not working out for us, and that she should for now focus on caring for her mother. We invited her to reach out to us once she returned, and we'd see if we could meet up.  RJ replied with a simple, "Yeah, OK thanks." I sort of wrote it off at that point. However, while out walking the dog I decided to give it one last try, and I sent a text telling her that, while it was probably a long shot, DW and I could be available for a FaceTime in about 30 minutes. RJ replied immediately, saying that she was not available but that she could take a phone call now. Even though I was not with DW, I decided to call her. She picked up right away, and was out in her neighborhood heading to an evening out with a friend. This was her first evening out since she began caring for her mother more than a week ago.  We talked for about 10 minutes or so, and I found her as engaging on the phone as I thought she was via text. This was a good sign, but I didn't push for anything. She said she'd be back in town early next week, but then was heading back out a few days later on a work assignment. We talked about her work, which I found fascinating. She's turning it into a vacation with her boyfriend, and she expects the two of them to be hooking up with others at least once while they're gone. She has a very healthy attitude about sex, and I think DW would like her a lot. The only thing I didn't like was her insistence that we pay for car service to and from her place and our place, explaining that she saw it as a minimal thing we should be doing as part of the arrangement. I didn't tell her that DW had already ruled RJ out if she insisted on car service every time, as she figured the arrangement money was enough for her to cover the expense of getting to and from our dates. I tend to agree, and I think that sugar babies who ask for "gas money" or car service all the time are less desirable than those with their own transportation. If we were going to meet for dinner and/or drinks and she expected to drink, I would absolutely pay for car service.  It's a minor expense, after all.  But for her to expect it as part of "sugar" etiquette rubs me the wrong way. It's a sense of entitlement that I find unappealing in Sugar Babies.  Honestly I would feel better about negotiating a higher allowance than shelling out dough for car service, or parking at hotels or restaurants, or even shopping for condoms.

When I got home, I was still on the phone with her, and I was going to try to get DW on the phone, but she was neck-deep in some stuff with the kids, so I had to end the call. DW was a bit upset that I had the call at all, but when I told her that RJ had insisted on car service for every date, she let it go. So RJ is most definitely OUT.

Pettit and I haven't spoken for a week, but she's still in the running. I'll probably contact her this weekend to set up a meet after we have our date with Rose.

Rose will be coming to our house in two weeks for our first encounter. Rose offered simply to charge us her massage rate, which is far less than an allowance, but I'm going to have a full allowance just in case things get really heated (and I hope they do). At my request she'll be bringing all her toys, massage table, and other erotic stuff, to loosen DW up and put her at ease. "Let's both make her cum," I suggested.

Having DW at ease is extremely important here. The better she feels about this, the more likely this arrangement is not only going to happen, but also going to continue happening. I have been suggesting that, as a way to get a small idea of what a threesome might be like, we watch a video of a couple engaging in a threesome with another woman. Playboy TV has a couple of series, one called Tripl3 Play and one called Toyride, that feature couples hooking up with single women, either via online meetings or from previous friendships.  We watched an episode of Toyride, about a married couple in an open relationship who goes around the country for Playboy to "research" adult toys and accessories. Every 25 minute episode features them having sex either with another couple or with another woman (haven't seen a male-male-female threesome yet). The couple are attractive but not porn-star hot. She's thin and bubbly, but not that above average.  He's definitely average-looking.  But they're cute together. In the episode we watched, they hooked up with a woman. The cameras maintain a respectable distance, but DW could definitely see penetration and oral sex happening. There's always a point of showing condoms too. She liked it, and for a second I thought I saw her touching herself under the covers.  I was above the covers and got hard watching the sex, but nothing ensued afterward (it was a good thing, as one of the kids knocked on our door and came in to complain of having trouble getting to sleep!).  We'll watch more of these shows, for sure, and I may suggest something a bit more hardcore after we fuck Rose.

The others have been very uneven, from little young girls wanting immediate sex to older (late 30s) unicorns who were probably a little too forward for DW (and wanted to fuck only me right away). So far, no one has really stood out except one, named Becks. She's a Brit with Asian heritage, huge dimples, and a very sexy slender body. Her job has her travelling a lot, so I don't know if it'd be a fit for us, but she's at least got a car.  We're holding off for now until she's back in town.

For now, DW and I are happy to play with each other and get excited to see Rose in two weeks.

Thursday, September 28, 2017

Open Marriage Update: The Therapist Weighs In, and a Boundary is Discovered

It had been two weeks since DW and I had seen our therapist. During that time, we discussed winding down our treatment, as the therapist was completing her practicum and would be leaving that counseling center in a few weeks. In fact, DW suggested we just stop altogether, using the idea of our now semi-open, poly-lite marriage as a substitute. I kept cautioning her that we hadn't been with anyone yet, and feelings were going to come up in that process, so it would be best to hang onto the therapist, at least for a little while.

Predictably, the subject of the money came up during our discussion of meeting with Rose. I had thought about bringing it up ahead of time that I wanted to avoid discussing the financial aspect of the arrangement with the therapist, but I knew that DW had strong feelings about it, and feelings are something we discuss with our therapist, so I just shut my mouth and decided to go with the flow.

We recounted how we had gone home after the last session and talked some more about it and decided to get started right away. The therapist took all of this in, and when DW started talking about her feelings, that she was struggling to wrap her head around how an arrangement is not prostitution, the therapist was given a chance to weigh in. Everyone who reads this blog knows how I feel about this, and I wrote about it in detail years ago.  But DW has what I call an old-school attitude about prostitution, that there's a stigma attached to it that is 100% negative. I disagree, and I brought this up in session. "There are plenty of women who don't view sex work as a negative, or maybe the only choice they have to make a living. But they've figured out how to monetize their own sexuality -- not just their bodies, but their whole approach to sex -- in a positive way.  I've read a lot about this over the years. It empowers them and helps them finance their future. Could be a porn star, could be an escort, or it could be a woman in the sugar lifestyle like Rose. She's a homeowner, she has a business, she has bills to pay, and she's able to use her sexuality, which we can all agree is pretty expansive if her story's true, to accomplish goals. When they get their financial needs they can focus on a building a business, or getting an education, or just living some lifestyle they aspire to where they can meet rich people and up their own games. I don't see that as a negative."  I don't think I convinced either of them, but it really doesn't matter. We talked about going the swinger route, either online or at a club, but the odds of finding someone were just too long.  The therapist got that part, and said something very insightful: "So there's definitely a convenience factor that you're weighing here." "Exactly," I said, "the financial exchange isn't just about paying for sex. If I had a girlfriend or someone I was dating, there's no assurance that she's going to sleep with me no matter how much money I spend. I have to be charming and 'a catch' 100% of the time to convince her that I'm worth having sex with. With a woman like Rose, all that dance goes away. It's a sure thing that we're going to have sex, so long as there's an attraction and some measure of chemistry."  I explained that the sugar website was created to give people who want companionship on both sides an opportunity to meet without much of the game-playing that goes on in the regular dating world. For the man, the financial investment is a way of bypassing seduction and games to cut to the chase of wanting to have sex with or spend time with, someone cute and sexy, and for the woman, it's a way to have the benefits of having a rich boyfriend without the messiness of discussing commitments. 

I then got my phone and pulled up the website to show her. I showed her how the profiles look no different than something on Match or OKCupid. She understood. The problem, I now see, is that DW hasn't gone onto the website to look since I showed her on day one. I made a mental note to myself to make sure she goes back on and reads lots and lots of profiles.

We ended the session on a much firmer footing than before, and DW is excited to get started and to discover stuff about herself. I suggested that our first session with whomever we pick focuses on her comfort level before taking care of me. "I'll have a good time regardless," I said, "so let's make sure a) you feel safe, and b) you feel you're #1. If you're uncomfortable, you only have to say 'time out' and we can stop everything."  In reality, however, I think she just needs to push through her discomfort and go with the flow. It's going to take more talking, and I think it's going to take some explicit sex talk. I want to start by watching some threesome porn (not the hardcore kind, but perhaps the Playboy TV kind that, while explicit, doesn't feature tons of close-ups) to get the dialogue started.

We had some errands to run after the session, and we discussed meeting with RJ before deciding on Rose. RJ had a transportation issue, and asked me to send her a car to take her to and from our first meeting. DW is fine with this on occasion, but if it's going to be something that is needed every time, then it's simply not convenient for us, especially when there's an option that doesn't require it. She believes, and I agree, that RJ would have to be really, really special to warrant the additional investment in transportation.  DW wanted me to tell this to RJ before we met, but I suggested that it would be better to ask that question face to face rather than via text. "She may prove to be really cool when we meet," I said, "and it may not be a problem at that point. Can you be open to that possibility?"  DW agreed to hold off.

Finally, a new girl has emerged. Pettit is a South American beauty in her early thirties with long, dark hair, a curvy figure, and really sensuous lips. She lives close to where Rose lives and has a car. She's an aspiring actress and is in school studying theater. She has an accent, she said, and is trying to lose it to get work. But her English is exceptional.

I showed DW Pettit's profile, picture, and the text messages she sent (though I deleted a few where I knew I was being overly flirty, like when I asked her to send nude pics). DW didn't like the profile, particularly where Pettit wrote about wanting to be spoiled. "She's already agreed to the same arrangement terms as Rose and RJ have," I assured her. "We're not going to take her shopping or on vacation with us." When she got to the text messages, she noticed one message where I called her "cutie." This really rubbed DW the wrong way.  "You aren't in a relationship with this girl, so it bothers me that you're already calling her 'cutie.'" I raised my hands in surrender, trying to make light of it, and said, "OK, no problem, cutie." That didn't go over too well. "I think you've found one of my boundaries," DW said sharply. "I don't want you flirting with anyone until we've at least met them." "Done," I said, "understood. Other than that, do you want to meet her?" 


I sent Pettit a note telling her we wanted to meet her, but that it would be a few weeks. We'd already agreed that there was no rush, so she was fine with this and said she looked forward to it.

I have to keep reminding myself that this entire enterprise will be riddled with land mines. I must watch my step!

RIP Hugh Hefner. Thank you for fighting tirelessly to loosen Americans up about sexuality. You're one of my heroes.

Tuesday, September 26, 2017

Meeting Rose: Wedding Nights, Yoni Massage, and Going with the Flow, Part II

Continued from previous post.

The talk ventured over into how she began sugaring. She revealed that she'd been married at a very young age, and when that ended, she needed funds to buy furniture and move into a new place. Her first marriage had been open, and she said she'd even had a threesome on her wedding night! (At that I shot a glance over at DW, who had this indescribable smile on her face, masking what I thought was a combination of shock and "gulp, what am I doing here?")  At first she thought she could use the site to find massage clients, but it morphed, obviously, into a casual sex thing. "I went on the site, on and off, for like a few years," she said. She then got engaged to a woman, but that broke off, and then had a monogamous relationship with a man that she found completely limiting, so she ended it. Now, she lives with a man in a relationship that has been "fully open from the start." I remembered a lot of this stuff from last year, but I still got to learn a few new things and watch DW's reaction. I followed her lead so that it looked to DW like I was just as surprised as she was, but I shot a wink at Rose at one point so that she knew I was just playing along.   She also told us a story about a recent experience she had with another married couple. They were friends of hers, and the woman was six months pregnant and was feeling horribly tense. Rose brought a female friend (I wondered if it were CJ) and they all took care of this woman and helped have several deep orgasms.

At that point, my lovely wife began to loosen up and talk about what she hoped to get out of the arrangement. God, I love her so much that she's being so willing and open!  I give DW lots of credit, but most of the credit goes to Rose, who was just so reassuring throughout the "date" that I knew DW was feeling at ease. One suggestion that Rose made for our first time together made a lot of sense to me. "I could bring my table, and I could give you a massage." DW revealed that she used to get a lot of massages when she was young, and liked a light touch rather than a deep tissue job. "I can do that," Rose said, "and I also do this thing called a Yoni massage." Yoni is the Sanskrit word for vagina which in Tantra is a sacred part of a woman's body. The massage is not to bring DW to orgasm, although that could happen, but to help her relax and bring previously-suppressed feelings to the surface. It's a process of creating deep intimacy between partners, and I really would love to see DW develop trust for someone other than me when it comes to sexuality.  This, to me, would make the entire threesome journey far more pleasurable and fun for all of us. 

Finally, Rose was very clear with us that she is not going to be a stickler for how many times a month we can get together under the terms of the arrangement. "I just go with the flow, whatever works, even if you want to stop and not see me again, it's totally fine," she said. I wondered why I didn't just dump Mel and continue with Rose. She was so much more my type! 

We finished up with talking about logistics. Since Rose has a roommate she can't have us over to her house. DW suggested our house, which sort of surprised me as this wasn't something we'd discussed. "Makes sense that, if we only have a couple of hours to do this that we don't spend half an hour driving to some hotel that we'd have to pay for. Just seems logical to me." So long as Rose leaves before the kids come home from their activities I'm totally fine with it. 

After about an hour together, we said our goodbyes. Once in the car, DW told me how much she liked Rose, but also wanted to give RJ a chance after she returned from out of town.  She is very excited to begin doing this. I had hopes that we'd do a little playing after the kids went to bed, and I even suggested watching a little threesome porn together, but even though she said yes, she collapsed at 10 pm and slept until morning.  She started giving me a hand job, but I wanted to fuck and there wasn't enough time. She had to start her morning. "Well, ok," I said, "you can give my cock a kiss before you go."  

"OK, I'll kiss your cock," she replied before taking the head in her mouth for a second. That was the first time, in literally years, that I heard DW say the word "cock" in a playfully sexual way. Changes are definitely happening.

Meeting Rose: Wedding Nights, Yoni Massage, and Going With the Flow, Part I

Arrived home yesterday to find the house empty, as DW was shuttling the kids to their evening activities. Mondays have now become our regular date night, and I eagerly anticipated this particular date night because we'd be meeting with Rose. It still feels completely surreal that DW and I are exploring a threesome after all these years of completely broken down sexual relations, but we've done a lot of work on our marriage over the past ten months and our communication and intimacy have dramatically improved since the summer.

When DW got home she told me she hadn't found the time to feed the kids, so we'd be having a late dinner with them after our date.  We got the kitchen ready, freshened up (DW even brushed her teeth and reapplied her makeup -- "It's a date, Porter, gotta look nice for a date!") and headed out the door. The Starbucks was just 20 minutes away in rush hour traffic, so the drive gave us time to catch up.

The night before, I'd had dinner with my buddy and confidant, Luke, and I caught him up on what had developed since our last conversation about three months ago. He was, understandably, both amazed and concerned, but without a hint of judgment, that DW and I might not be on as solid a foundation as I thought we were, and he urged me to be cautious and considerate.  One of the things he suggested was to discuss boundaries.  This was something that had been on my mind, and I had asked DW about what would be OK or not OK in bed with either RJ or Rose. She just didn't know, and hadn't really thought of it. But Luke's twist on it was to have me ask DW about those bedroom activities she would prefer remained exclusively for us.  For example, perhaps DW would not want me to kiss these women on the lips. I liked that approach better, and on the drive to meet Rose, I asked her that question. She was caught slightly off guard. "Honestly, I don't think I've ever really thought about that," she said.

"You don't have to answer now," I said, "just give it some thought to see if there's something you'd like to reserve for just the two of us."

"I don't know," she said, her delivery slowing a bit as she chewed on the thought. "Maybe oral, I guess? Because that's, like, the only way I can have an orgasm?"

You can imagine the panicked thoughts that coursed through my brain at that moment! Whaddya mean, no oral?! But, keeping my composure, I repeated back to her, "So, you would want me not to go down on the other woman because oral is the only way you can come?"

Realizing that her idea was not quite sensible, she said she was just thinking out loud. Just to make sure she realized that such an idea was actually quite absurd, I asked another question. "So, what would you object to if I went down on both of you? That she might also have an orgasm?"

"Well," she said, "we're doing this because you want penetration and I can't give that to you, so maybe you just have intercourse with her."

"So, what she might want is not important to you?"

"I know, I know, it sounds kind of stupid," she admitted. "I'll think about it a little. It may be nothing at all, actually."

We got to the Starbucks on time but didn't find Rose there, though she'd texted me that she'd gotten there early. A quick text and we found each other.  Rose wore a grayish top over white shorts and flip flops, much more casual than either DW or me. I couldn't help but think the wardrobe differences were generational! In any event, she looked as cute as I remembered her from last year, though perhaps a bit thinner, which was fine by me!  She walked over to DW and gave her a hug, and then gave me one. A very good move, I thought, to break the ice right away and make this about friendship rather than something quasi-business-y and semi-awkward.  I opened the door and let them both in.

We found an actual table for four in a Starbucks at 6 pm, which I found astonishing. I wasn't going to order anything, but I got the girls' orders and went to the counter to place them. This was a deliberate move on my part, to get DW to start talking to Rose right away without me there. I don't want to characterize DW as too shy to have a casual conversation, but with me there I knew she'd lean on me to start the conversation.

Once back at the table we made some small talk. We learned that Rose was a homeowner, having bought her first house with her mother's help about six years ago, when she was in her mid-20s. I was mighty impressed, as she was the only other woman I'd met in sugar world who owned property, the other one being Dale. She left her job of five years just over a month ago to focus exclusively on her business, and was able to make enough money to pay her bills and pay for the house.  Her boyfriend and a roommate also shared the house expenses, so it was bearable.  Still, very impressive!

-- to be continued...

Friday, September 22, 2017

The Heat is Turning UP

Since I posted our profile on the sugar daddy website nine days ago, we've been viewed 130 times, been favorited nearly 40 times, and received messages from dozens of different young women. And now, we're down to two POTs in whom DW and I are interested.
  • Rose: readers know a lot about her. At the moment, we're scheduled to meet her for drinks after work on Monday. As I type this blog post, she and I are exchanging "behind the scenes" text messages so that she's informed about DW's journey before DW shares it. I want Rose, with her background as a healer, to be able to coax out of DW some of the pain and other stuff she's been keeping inside. Already Rose has identified one possible area I don't think DW has explored, and perhaps in time we'll introduce that, if Rose becomes our partner. So far, I'm thinking she's a better fit for us than...
  • RJ: I'm running out of names here, there've been so many!! Anyway, RJ is a late-20s brunette in the entertainment business and who lives on the other side of town from us.  She's got really sexy, long curly hair, blue eyes, and is very slim and petite (like DW). She identifies as "queer," which essentially means that she can be any one of the previous letters L, G, B, or T, or all of them, and not being 100% sure is OK. She's had sex with mostly men, and just one woman, but she loved that experience so much she considers herself at least potentially bisexual. She's in a committed but open relationship with a man at the moment. From the texts we have shared, I consider her to be very trustworthy, so much so that I showed the entire thread to DW last night to get her buy-in to set up a meeting with her. What I really like about RJ is her sexual attitude, which I consider to be a bit bolder than Rose, but that is just a first impression (and I haven't fucked RJ like I have Rose). RJ offered to send me pics of her "partner" so that we'd consider a couple swap, but until DW is able to have intercourse and has upped her oral game, I'm leaving couple swaps off the table. Besides I think it's still too big of a step for DW right now.  I haven't shared with RJ the details of our marriage the way I have with Rose, either, because I'm not really there on trust with her yet. But boy, is she cute.
I've told the other POTs that we've settled on two already and wished them luck.

I told DW that we'd find a suitable partner within a week, and we've found two suitable partners in less than 10 days. I know my shit!

DW is still wrestling with the financial aspect of it. Today I suggested that she go onto the website and read a whole bunch of profiles to see how these women are presenting themselves, from their pictures to their bios and wants.  There is sure to be a number of profiles that are lame and/or overtly focused on money, but those are the ones I've ignored anyway as being too much like escorting. I also suggested she then check our professional escort websites to see the difference. She declined that but I'm not letting her off the hook because she needs to see the difference based on facts.  Plus, I think once she meets these two women she'll have a different outlook. I told her to be careful of asking the question about prostitution because she'd likely offend one of them, especially if they don't consider themselves escorts.

Finally, to give her a clue as to the value of the swingers websites, today I created a profile on one of the biggest such websites, and found that there were a grand total of eight bisexual women looking for couples of any kind within 50 miles of our home.  Of those, three were women over 40, which is out for me, and two of them wanted an allowance.  To have only five choices rather than more than 100 will greatly enhance the credibility of the sugar website.  Plus, there's the added burden on the swingers website that there's a recurring monthly membership fee, which both of us find distasteful.  There would be plenty of fun to have if or when DW decides to go the swinging route.

Last night, after showing DW the text conversation I had with RJ, DW struck me as having second thoughts about the whole thing, but it turned out to be just the money aspect of it. I also asked her to play before we went to bed, and she was reluctantly game. We had just got done watching a show on TV that featured some very beautiful women and men with fantastic, athletic bodies, and we were both a little horny. She slipped off her pants and opened her legs. I decided to go down on her to see how receptive she'd be. Within only a few seconds her hips were rocking up and down again and her eyes rolled back in her head. I did nothing out of the ordinary, mind you, but she was very into it. I put a finger inside her once or twice and licked her perineum, and in less than three minutes she came with a loud moan. I love when that happens!  I then lubed us both up and started doing our rubbing thing, but we also tried penetration. I was able to get half of my penis inside her this time, more than before, which was a good thing. She asked if I enjoyed it, and I said, "Of course it does, but not all the way awesome." She said it hurt a little less this time, but this was as far as she wanted it to go.  I pulled out and rubbed on her for another couple of minutes.  Her having had an orgasm a few minutes earlier made her pussy sensitive and she didn't enjoy it as much, but it felt amazing for me, and I came very quickly. I'm a little concerned about how I'll perform when I fuck either Lia or RJ -- ten months without intercourse is a long time!

Rose wants to bring some toys to our first session to help DW over the hump with penetration and to get her in touch with her body's feelings.  I'm really hoping this works out.