Thursday, January 28, 2016

Sweet Sam

In my last post, I briefly noted that I was going to see Sam to make good on a promise I'd made not to cancel on her.  You'll remember that, for a couple of years, I've kept Sam in my back pocket as a possible sugar baby in case I was unhappy with everyone else.  I saw her again last October after a two-year break, and we had a pretty fun time.

I had booked the same hotel where we first got together in 2013.  I had really hoped, and pushed Sam, for a full two-hour date where we could relax and hang out.  Personally I just don't like feeling rushed, in case I want have more fun with her.  Unfortunately, I'd misjudged traffic and arrived five minutes early, and I still didn't have condoms.  I had to spend an additional 20 minutes doing that, so by the time we were checked in, we'd lost a half hour.

One unexpected benefit was that the original room I'd booked was still not made up, so the front desk gave me a better room for the same price.  The room had a jetted tub big enough for two, right in the main room.  I was busy contemplating the possibilities there when Sam sauntered in.  I'd adjusted the lighting to what I thought was perfect, but she immediately started testing all the lights to see which was best.  "You can do that while you're naked," I said.  She was wearing gray sweats and a whitish blouse with a peasant collar, which made her look a little like a chef, especially with her hair pulled back.  "Gladly," she replied, and she let me unbutton her blouse while I kissed her.  She kept craning her neck around looking at the room.  At one point I took her chin, held it there, and said, "eyes on me, please."  We laughed. kissed, and resumed undressing her.  She was wearing no panties under the sweats, which was kind of hot.

Eyeing the tub, she said, "I'm down if you're down."  "Oh, I'm down," I replied.  While the tub filled with water, we started making out on the bed and got completely naked.  I briefly went down on her and she did the same.  The water distracted us a little -- well, it distracted her -- but I found it cute.

We climbed into the tub, having set the jets for the maximum 15 minutes allowed per the timer switch.  Some snuggling and kissing and stroking each other, and we toweled off to have sex.

I have to say, I really enjoy having sex with Sam.  With other girls, the act of sex sometimes gets bogged down in what feels to me like a performance.  There have been a few who just let themselves go and totally enjoyed the moment -- C/Hayden, Audrey, Joni, and CC come to mind -- while others like Staci (loud shouter), Jade (a little controlling), Natalie (must use vibrator), and The Dancer (fake dirty talk) either thought they needed to perform for me or weren't quite as into it as I would have liked. Sam falls squarely into the former category. She's not a big moaner, doesn't talk dirty a lot, and doesn't make a big deal out of how she looks or anything.  But, the way she held so tightly onto me while I was on top of her, the way she would sort of gently moan into my ear, the way she took my hand while I was going down on her and putting it on her breast, all told me that she was really enjoying herself and was completely present with me.  While I was taking her from behind, I slapped her butt to see what her reaction would be. When I didn't do it again, she reached for my hand to signal that she wanted me to do it again.  Her beautiful round ass got pretty pink!

I felt that she was close to orgasm so, picking up the pace, I took her face in my hands and kissed her hard, looking into her eyes.  We both came together, her body twitching involuntarily.  We laughed again, kissed again, and we just lay there holding each other.  She was just so sweet, so affectionate, and seemed so grateful to have had a good time with me, it sort of made me feel a little sad that this would likely be my last time with her.

We climbed into the tub and chatted for another twenty or so minutes before it was time to go. As we dressed, she said she'd like to have this room again for next time.  I don't know what got into me, but I didn't have the heart (or the balls) to tell her that I wouldn't be seeing her again. It just didn't seem right. Both of us had had such a great time together, and there definitely was a feeling of mutual gratitude, not only for the opportunity to have sex with each other, but to be together.  Sam is a bright, sweet, beautiful, goofy, lovable, and sexy woman.  She's so laid back, nothing seems to get to her (unless a dog is hurting), and she just takes everything in stride.  I'm fairly sure that if I had told her that I'd found a sugar baby with whom I wanted to be exclusive, she would have said "no problem" and it would not have fazed her.  But at that moment, it just didn't seem like the right thing to do, when we were both smiling from ear to ear and feeling some sincere affection for one another.

She left a few minutes ahead of me, and I took a moment to answer an email or two before heading home myself.  I'd be home for dinner.  When I saw DW as I walked in the door, I gave her a huge hug.  She looked beautiful and the house seemed at peace.  Or maybe it was just me.

In my next post, I'll update you on Red and other developments.

Wednesday, January 27, 2016

One Last Time With Sam

The fallout of my wimpy panic attack after meeting Red for the first time has manifested in my making good on a promise I made to Sam when I arranged a date with her.  Because she was initially reluctant to meet with me due to several canceled dates,  I promised her I wouldn't cancel again.

She texted me this morning to say she was free today. When she asked if we could end a little earlier, I saw an opportunity to back out,  and insisted on a full two hours with her.  She made a call and pushed back an appointment to later and said,  "I'm ready to see you." I have booked the room at the hotel where we were first together.  "I want you naked immediately," I wrote.  "We can adjust the lighting as we go."

Given that I'm really going to shift my thinking, and focus on Red,  this will be my last time  with Sam.

Thinking About Red

Today is the day of Red's surgery.  I texted her this morning to let her know I was thinking of her and to wish her a speedy recovery.  If you can hold a good thought for her right now,  I'm sure she'd appreciate it.

Updates on her later.

Tuesday, January 26, 2016

Intimate vs. Platonic Sugar

As I have been contemplating the possibilities of entering into a Sugar relationship with Red, it has been on my mind that our dates might not always be sexual ones.  This is different from every single sugar relationship I've had in nearly eight years.  Even the make-out date I had with Natalie a couple of months back had me between her legs, even though we didn't get naked and fuck.

Red goes in for her surgery tomorrow, and she called me this afternoon because I wanted to talk to her before she went under the knife.  I am not ashamed to admit that my eyes lit up when I saw her number on my phone.

"Hi, sweetheart!" she began. "I'm so glad I'm gonna get to talk to you before surgery."  I had sent a text earlier wishing her well and sending healing thoughts.  It also read, "I think you're an incredible woman.  I hope you think I'm the right man for you on the next step of your journey.  Think we'd have lots of fun together."  Confident, but humble.

Red told me that she had been rushing all over the place, rearranging her calendar.  Her project had been successfully put on hold for two months, but there was another project she had been hired to do that was supposed to begin next week.  Clearly, she wasn't going to be up to starting it, but the project directors told her that they'd delay the start until she was ready to begin.  On top of that, she is also having to move her residence, as her lease is up and she can't renew it.  She and her best friend are moving in together temporarily, until she's feeling ready for her own place, and the friend will be taking care of all the moving, including getting Red's stuff out of storage to set up home.  It will not be a perfect arrangement, but the rent was affordable, she said, and she'd be able to get her own place soon enough.  With all that was falling into place, I could not help but be impressed.  "You're getting it done, babe," I said, "but you're leading a charmed life right now."  She said she felt grateful that people were stepping up to help her.

Even with all the help, however, the financial burden this is all placing on her is challenging, even for someone like me, who makes a decent living.  She has insurance to cover her surgery, but the co-insurance payment/deductible is a couple thousand bucks.  On top of that she has moving expenses (first month's rent, security deposit, etc.), probably about the same. On top of that she won't be able to work.  She suggested -- at least I heard it that way -- that these two expenses would leave her flat broke.  Ah, the life of a freelancing sugar baby!

In this light, I believe, she expressed a desire to see me before she went in for surgery.  Clearly she wanted the allowance money.  But I have plans and cannot see her today.   She then suggested we get together a few days after her surgery.  "You're gonna be hopped up on pain meds," I said, "you won't be able to drive."  "Well," she replied, "you can come to where I am, or we can meet somewhere close.  We'll work it out."  It was clear to me that my money was a huge part of the deal for her.  But this is sugar dating, not  Allowances are part of the deal.  If I'm going to have a sugar relationship with Red, I have to keep that in perspective.  There is a great chance that she is sincere in her intentions about wanting to be with me.

"Well, we can deal with that later," I said.  "Meanwhile, don't think of me, I just want you to focus on healing up as soon as possible.  I'm really glad I am getting to know you, though.  I think that, even if we don't get together, there's a lesson for me to learn, and I want you in my life at least until I learn it!"

"Oh, you will," Red said.  "You're a special man, Porter.  I can't wait to see you."

We said goodbye and I wished her luck.

A couple of hours later, I got my test results and they are 100% negative.  Not wanting to wait to tell Red, I sent a text: "Too bad your surgery can't wait till Thu. I want you, in the best way!"

It will be several weeks yet before Red and I consummate our relationship sexually.  Meanwhile, I will be giving her allowances just to get together.  I'm sure I'll get some physical reward for being with her, but I want to stay level-headed about all of this.

I read this story earlier today about platonic versus intimate sugar relationships.  The author works for the Seeking Arrangement website.  In it she writes that there absolutely are sugar daddies who want nothing but a platonic relationship, for a variety of reasons.  One thing she writes with which I disagree is this:
[Y]ou don’t necessarily want to put that you’re only interested in non-sexual relationships on your profile, even if it’s the truth.A Sugar Daddy isn’t looking to have sex straight out of the gate, so meeting him without telling him that isn’t a big deal. If he asks before meeting whether you’ll have sex, say you don’t know. How can you? You’ve never met.After establishing chemistry and once he decides he likes you as a person, he’ll want to spend time with you and help you out, even if there’s no sex. When the topic does come up, then you can let him know you’re not ready [for] or interested in intimacy.
I've seen plenty of profiles from young women that state unequivocally that they are not interested in a sexual relationship, that they just want a platonic benefactor.  Sorry to burst the bubble, but while there probably are sugar daddies out there who are not sexually active, whether it's a physical limitation or a personal choice, it's irresponsible to suggest that these types are anything but the exception rather than the rule.  In my opinion, the odds of landing a generous non-sexual sugar daddy who just wants friendship are about the same as going from high school football through college football to the NFL, or a little more than one in a thousand.  I'm sure that if Seeking Arrangement formally polled their active SD members, fully 99.9% of them would say that no sexual contact with one's SB is a total deal-breaker.

So, while I'm willing to spend platonic time with Red until she recovers, and provide financial support in the meantime, it won't take me long to grow suspicious if she stalls on sex once she's recovered.  Something tells me, however, that won't happen.

Monday, January 25, 2016

Update on Red -- Possibilities

Red has been showing me more of herself in the days since we met.  I'm thinking that she is probably more like herself from a distance, like me.  I don't have a steely exterior like she does; honestly, I haven't really needed it, and I can see how a beautiful woman might need it as protection. Particularly since I've learned a bit about her.

The day after we met, I texted her in the evening to tell her I'd had a "much better" day than the day before, and asked how she was doing.  "Saw my [doc] this morning."  Given her illnesses I understood what this meant.  She let me know that she would have to have surgery.  "It's a good thing," she wrote, adding that it would happen as soon as the doctor could schedule her.  There was a good chance that she'd be out of commission while she recovered, and I wondered how that would affect her timeline for one of her projects. She said it would push things back to the spring instead of now.  

Realizing that Red was revealing a bit about herself, I took an opportunity to reciprocate. "So, I know I made a mediocre impression yesterday. I apologize."

"You're fine."  She was still considering me.  "Would you be open to getting together, even if you can't be intimate?"  She said that she was, which I found very gratifying.  A few sentences later she indicated that, given the fact that she had a rather large deductible for her surgery, she would want the agreed-upon allowance even if we weren't sexual.

I found myself on the horns of a dilemma.  I have never, ever given a potential SB allowance for a casual get-together.  I remember that C/Hayden insisted that the allowance was an investment in her, and if we had sex, it was because she wanted to, not because I was giving her money.  I know that is what SBs say to differentiate themselves from escorts, and I respect it.  However, as an SD I have maintained for years that I wanted a sexual outlet, and every woman I was with knew it.  They knew that sex was part of the arrangement, and if they wanted to call me a "pay-for-play" SD, so be it. I knew better.

But now, I have decided that I need to shift my thinking. Red is not a pay-for-play SB. An arrangement with her could come about as close to being the ideal lover/mistress scenario I have wanted for years. Given the additional years of experience I've had, and Red's previous experience as a mistress, I can see that the pieces are there to create something wonderful. Are we right for each other? I'm not yet sure. But she's a quality woman and I'll be damned if I take a pass on her because I don't yet feel up to the task. With her being right there, I keep her close and I get ready. 

Therefore, I decided to play a longer game, and I agreed to the allowance even if there was no sex.  In the back of my mind I hear that voice warning me that the Sugar Bowl is "fake as fuck," so I'm a tiny bit cautious that she might be playing me, and I'm not quite going all in with her just yet.  I'll keep paying close attention to her actions going forward.

"I'm happy to help," I said, adding, "Here's a completely selfish question: is sex painful?" 

"No," she replied, "I don't really have any [disease-related] issues anymore. Slight fatigue. But I've pretty much cured myself."  The surgery, she added, would resolve her last issue.  I wasn't sure sure if her answering this question meant she was open to having sex with me after her surgery, but I decided that until she showed otherwise, I'd play along.

I then told her that her last name was the same as a former SB, and just to be sure there was no connection, asked if she had any relatives working where Natalie worked. "Not that I know of," she replied, "though I don't know [that] side of my family. I'm raised by mum."

Ah, she just peeled back a layer and now understood why she might have that tough outer layer.  It ain't easy being raised by a single parent.  Couple that with her health battles and business ventures, along with her serious beauty, and she'd have to develop a very tough exterior in order to navigate through life.  After establishing her ethnic heritage, it was time to make a date.  She agreed to have lunch, a week to the day of our first meeting, for sushi, which both of us love.  

Wednesday couldn't come soon enough for me.  

The next day was testing day, and I sent her a picture of my arm with the bandage over the elbow to show that the blood had been drawn.  She revealed that she'd been tested two months before and hadn't had any partners since then.  So, once I get my results back, which could be as early as tomorrow, she'll be free to mess around.  That is, if my bad luck doesn't come back and she gets scheduled for surgery this week.  That is, of course, entirely possible.  As I did with C/Hayden, I will offer any assistance I can as she recovers.  

Last night, we texted some more.  I told her I was worried about her surgery, moved by how much she has attacked her life, but "mostly, though, I've been thinking about kissing you."  She told me she had no plans for the afternoon following our lunch.  Knowing that she would probably play with me, I held back in overtly suggesting a sex date, and instead offered to do "whatever we decide, no agenda."  After suggesting a few outdoor things, we agreed it would be better to keep things indoors. Then I went in for the close: "The view from the 10th floor of [the hotel next to my office] is very nice."

"I wouldn't know," she replied, "I've never been."  So coy.

"Would love to show it to you."

"Is that a restaurant?"  Seriously?

"No, it's a floor of a nice hotel with a view of the surrounding area."

"Bedroom?" WTF?

"Several," I replied.  "If that's not to your liking there are others."  That got a smile.

"My results may be back Tuesday.  If so, I'd like us to spend the rest of the afternoon together.  Thoughts?"

I didn't get an answer.  It was nearly 11 pm so I figured she put the phone down and fell asleep.  In any event, I'll play it by ear and see where things go.  Just wanted to see if she had time that day anyway.

This morning, I thought that in hindsight that I should have been more direct with her.  I was being overly cautious. She had told me on the first day that "in real life" she was a dominant type, but that she was interested in exploring being submissive in the bedroom.  I wondered how she'd respond to me if I took on more of a dominant role in how I set up dates.

I texted her earlier this morning and she did get called into surgery for the day of our date, so she'll be out of commission for awhile.  I've offered help, so we'll see if she allows that level of intimacy.  I'm not holding my breath.

Friday, January 22, 2016

A Paradigm Shift is Needed Now

In the beginning, nearly eight years ago, one of my reasons for becoming a Sugar Daddy was my desire for a sexual outlet, outside of my marriage, because that relationship had seen a significant decline in both the quantity and quality of sexual contact. Not only were my DW and I not making love enough for me, what we did when we made love was boring, dispassionate, and unsatisfying. DW also lacked the skills I wanted in a lover, wife or otherwise.

Through the first year or so of my activity, from May 2008, I selected young women who were easy: agreeable to my modest terms and not at all demanding of me beyond the best sex I could give them and my financial support.  And then in July 2009 I met C/Hayden. A woman younger than I had been looking for, she nevertheless charmed me with her warmth, intelligence, and sexuality. The non-exclusive relationship lasted, off and on, for three years. The first half closely resembled the short-term, recreational (sexual) affairs I'd had up to the point of meeting her.

I took a short detour in late 2010, after a breakup with her, and when we reunited in March 2011, our relationship started to resemble something more long-term. We were still non-exclusive; I occasionally saw other women, while she had her new, serious boyfriend. Within eight months of that reunion, both of us had said "I love you" to the other, although her by text only. While it signaled the beginning of the end for us, reaching that level of emotional connection showed me a different paradigm in the Sugar Bowl: the possibility that an arrangement could be, within its narrowly defined boundaries, be emotionally fulfilling and deliver benefits that the traditional Daddy/Baby arrangement usually did not. Love was possible, and so long as we both were able to keep our wits about us, it could be wonderful. And for C/Hayden and me, it was, albeit so briefly.

In the months that followed C/Hayden's formal ending of our relationship in September 2012, I was emotionally devastated. It wasn't because I was unprepared for her departure, but because I had to come to grips with the complete removal not only of her physical presence, but her emotional presence in my life. And it was permanent and unequivocal.

In the three-plus years since then, I have engaged in a continuous series of connections, both brief and somewhat lengthy, that had me trying to re-create what I'd had with C/Hayden. Only this time, I would apply the lessons I'd learned -- don't fall in love, insist on more vulnerability from her -- and get there faster than I had before. I wanted that emotional, intimate connection, and I wanted it badly. My marriage had started fraying late in 2011, and with that stress, plus hitting my fifties, losing C/Hayden, and immediately hating the new job I'd gotten, I was near despair. When Lola, and then Jade, came into my life in early 2013, the emotional enmeshment seemed to manifest itself early, to my great joy. Lola decided almost immediately, however, that she would reserve that emotion for a man who was actually available for more than a sugar arrangement, but Jade was somewhat younger, more focused on her budding artistic career, and she embraced the connection wholeheartedly. We laughed, fucked, and eventually started talking about real plans to be together. My marriage was at its lowest point ever and I was uncertain if it would last another year. Jade, however, began to have a change of heart, and began concocting falsehoods and displaying some immaturity that really turned me off. After catching her in one too many lies, I was done with her by the end of 2013. Meanwhile, I'd managed to spend some quality time with Sam, who to this day is still peripherally in my life.

After some brief dalliances with Leah and Belle, I settled on Audrey in April 2014. In her I found a partner who was the perfect short-term recreational girlfriend. She was great in bed, she fully participated in our dates, and she was willing to try anything.  Good, Giving and Game. We tried swinging together. By the end of 2014, we were good friends, and cared about each other, but there was no hint of an emotional connection. Neither of us wanted one, really. Meanwhile, I came to a huge realization about my marriage: that I was still deeply in love with DW and I wanted to recommit to our relationship, despite the fact that I would not commit to monogamy (Note: since we've been completely without sex for a year, and almost none for two years, I wouldn't call what we have now monogamous.  Monogamy implies there's sex going on. What we have is celibacy.)

But in March 2015, I made a stupid, indiscreet mistake that cost me my relationship with Audrey. And I was once again on the market. I have been with eight partners since May 2015: Mouse, Staci, College, Sam, Fleur, Rachel, Natalie, and the SB with no name. Other than my two-month stint with Staci, I saw each of these women only once.

The last four of these encounters, however, have been eating at me, calling into question what I was doing and why I was doing it. None of these encounters delivered the true satisfaction I wanted. Sure, I came with all of them (twice with Rachel), but I didn't once feel my heart in any of these encounters.

My heart! Could it be that I wanted to feel something again? Was it no longer enough that I enjoy a sexual encounter with an attractive woman for whom I felt only minimal emotional connection?

As I'm not a believer in accidents, but in the power of the Universe to put in front of me exactly what I need when I need it, I believe today that Red has come into my life to teach/show me something about myself. Her desire for a stable partnership that lasts and provides emotional fulfillment as well as sexual hotness truly resonates with me. When I sent her that text yesterday about what I wanted in an arrangement, I meant it. I was unprepared for Red because I didn't realize how badly I needed it. I was going through the motions like I always do, relying on what has always worked for me to get laid. But with Red, I don't just want to get laid. I want more. Hell, Red doesn't even have to be the one; she symbolizes the one. If she gets to be the one, fantastic. But there are others.

This new desire represents a paradigm shift for me. The fact that I'm getting tested to be ready for a relationship with Red is symbolic of new thinking. Even if she's not the one, getting tested benefits every other potential Sugar Baby.  And I enter the relationship "clean."

It's almost as if I've finally completely healed from a divorce and I'm now ready to date seriously again.  But the question is: am I ready for this level of involvement with a woman who is not my wife? I don't know. Further, I don't care if I'm ready or not. I'll be content to "fake it till I make it."

As I have written before, there are two types of relationships.  In the short-term recreational ones, it's all about keeping it fun, and anything goes to make it fun, including treating it like a long-term relationship.  Love can work, so long as both know the boundaries.  I feel like I'm nearly ready for that kind of arrangement again.

In the next post, I will update you on what's going on with Red.

Thursday, January 21, 2016

Meeting Red and Kona the Same Day

I met yesterday with Red.  The anticipation level had me very hopeful that things would go well.  We had a great phone conversation early in the week, and we seemed to be on the same page about what we wanted.  I thought that we'd enjoy a brief sit down coffee meet, then adjourn to a hotel to play.  I was prepared.

In person, Red exceeded my expectations in the looks department. About 5'7", red hair past her shoulders, brown eyes, and a curvy, busty figure well-accentuated by the beautiful dress she wore and white pumps. It was a business outfit, to be sure, but certainly revealing with its low-cut front. On her face were a pair of very stylish glasses with gray frames. They gave her a very appealing, but powerful look.

We hugged and I bought her a cup of coffee at the coffee shop in my office complex. Being late in the afternoon, I wasn't expecting to see (and didn't) any co-workers while we were there.

The conversation got off to a decent start, talking about our careers and ambitions, but within about 10 minutes or so things somehow started going downhill. She told me about another man she'd met the day before, an Asian man who couldn't hold up his end of the conversation. "After he offered to take me shopping, I just said no and goodbye, then I walked out."

Red then knocked me on my heels with her questions.  It wasn't what she asked, it was how she asked them. She allowed for very long pauses in the conversation, which made them feel like uncomfortable lulls. "Tell me more about you," she said. "What would you like to know?" I replied. "What do you want to tell me?" she countered. Annoying! I gave her some of the basics, answering why I was looking for a Sugar Baby. She already knew the answers, since both my profile and our earlier talk had covered this topic. So why was she doing this?  I answered her questions, and since she had already given me a pretty thorough overview of herself, there really wasn't much I needed to ask her. I said, after another lull where she just looked at me, "You're not an easy read." "Are you intimidated by me?" she asked. "Not at all," I smiled. Just want to know if there's anything else you'd like to know about me."  She then asked me when I'd last been tested. "About a year ago," I said, "probably overdue."  Another shorter pause. "I'd like you to get tested first before anything happens," she said, adding, "We can do it together if you want." "Sure, that's sounds fair," I said. Not much more was said, and I think the whole thing lasted about 40 minutes. We weren't going anywhere to play, and we saw each other, and neither of us had had an experience similar to hers with the Asian man, and walked out. There was nothing left to say at that point. I said, "Well, let's talk more later after the test results are in." I walked her to her car, gave her money for parking fees, which she graciously accepted, and gave me a hug. The fact that she didn't kiss me there told me that there was little chance anything would happen. I left her car after saying goodbye and walked to my car. From my front seat, I texted, "Great meeting you. Still not getting a read on you though." I then added, "If I had to list one of my many flaws, one of them would be that I do not read subtlety very well. Very much hoping to see you again, and I hope you feel the same way." I meant every word of that. Red may have unnerved me with the way she showed up, but I attribute that to my tendency to be shy at first, especially with someone with her looks.

"I enjoyed you by I'm concerned with the [amount of activity you've had]," she wrote. "Seems like you do this a lot and I find that unfavorable."

Wow, that felt like a shut down. I asked if I could call her to talk about that, but there was no answer. We were both driving at that point. I figured I'd hear back later.

Meanwhile, my head was playing games with me. I knew it wasn't a gut feeling, because my thoughts flew all over the place. Eventually, they led me to Kona, with whom I was supposed to meet that afternoon. I looked at my clock and our meeting time was 30 minutes away. I was about 15 minutes from where we'd agreed to meet, so I texted Kona to see what had happened. "Hey, weren't we supposed to meet for coffee today? I never heard from you. I'm close to that coffee shop now. Wanna still meet?" She wrote back and said she'd be there at the designated time.

I got there about 15 minutes early, and since I hadn't heard from Red, decided to forego the phone call and just tell her what was on my mind. "I completely understand how you feel. I also find [my recent sugar activity] unfavorable. I want one stable, emotionally and physically fulfilling relationship. I can get tested, and show you that I'm clean, and we can take it from there. Are you open to that?" She replied that she was. "Great," I said, "I'll get tested as soon as I possibly can, and let you know when I have results, so we can plan another date." "Ok." I made some calls had the test scheduled for two days later and I let her know. The results will be mid next week.

Kona showed up on time. She wore a tight black sweater, a red print skirt that was too short, and black stockings with very high heels. Typical first meet sugar baby attire! Once I saw her face, I was done. Not nearly as attractive as I thought she might be, although she had a decent body. She spoke with a thick accent and it was hard to understand her at times, and over coffee I never gave her any indication that I was interested. She had gray teeth too; completely gross. She had lived in California just four months, having moved from Hawaii, where she'd lived for just a couple of years. She grew up in Shanghai, just like Sha from many years ago. The conversation ended when DW called and wondered when I would be home. I said my goodbyes, got in the car and headed home, telling Kona that I'd be in touch. No way, not after my terrible history with Asian women, was I going anywhere near her.

On the way home I reached Sam and planned a date with her for this Friday, before she headed back out of town again. Why was I doing this? Because I believed that Red would probably decide against a date with me even after the testing came back.

I arrived home at 5:45 to an empty house. One kid at sports till 7:30, the other at a school basketball game, and DW took the dog to go pick that kid up. I decided to do a little checking up on Red to see if there was a public profile. She'd looked me up, so I felt no compunction against doing it too.

I found some very compelling stuff. Red had told me about some of her time as an athlete. I found her personal website, learning her last name (the same as Natalie, interestingly, so it made me wonder if she were also Latina), and learned that she'd accomplished a lot as an amateur, turned pro, but had to quit after she was diagnosed with a couple of debilitating illnesses. I saw parallels to C/Hayden here. The stories were inspiring because she was clearly overcoming them and making them work to her advantage rather than letting them take her down. I had to let her know: "Not only are you unbelievably beautiful, I just read your story and I'm so impressed with your courage." She thanked me and asked how I'd found her. "Not too hard," I replied. I then decided to open up a little. No sense in closing up, especially since I wasn't at all certain she would agree to date me. "I am really good at finding the right things to say five minutes after I leave you. Comes from growing up painfully shy."

"I, too, was shy. I understand that."

"You asked me if I was intimidated by you. It wasn't you; it was your glasses. I know why you wore them today."


"They make you look formidable."

"Thank you."

I didn't mean it as a compliment, by the way. Substitute "formidable" with "bitchy and cold" and you get the idea.

"The face picture you'd sent me before, without the glasses and the gray sweater, gave me a totally different impression."

"Is that a good thing or a bad thing?  What impression did that picture give you as opposed to me in person?"

I sat on that question for a few minutes and thought of the most complimentary words to use that would avoid more questions."

"Softer.  Less formidable. Same with our phone convo."

"Are you uncomfortable with formidable?"  Fuuuuuck!

"My shyness comes out, that's all. Couple the persona with your looks and I lost my voice.  Once I get over the shyness, I'm devastatingly charming."  That made her smile.

"I'm noticing that I'm revealing a lot.  You have a talent for getting people to do that."


"Mm.  I'm off to pick up my kid.  I'll check back in when the results are back.  You'll want to see them."

Readers, you will immediately be telling me that you don't like Red and that I should forget about her.  But I absolutely do not feel that way.  I see from my writing that Red comes off cold and bitchy. Not at all. I got the impression that she knew exactly what she was looking for, and knew the questions to ask to see if she could rattle me (she did) because she wants a man who doesn't get rattled. Do I think that makes her the wrong girl for me?  No. I may be the wrong man for her, but we'll see.

As I see it now, even though I felt prepared to have a meet then play, I was utterly unprepared for her.  After our phone conversation, which was engaging and funny and light, in comes this very serious woman, probing me and looking for flaws. She uncovered many (even the ones I didn't freely admit). The fact that I started texting Kona and Sam right away shows that I ran for the tried and true, the sure things, out of insecurity, not because Red was wrong for me.

More reflections on this in my next post.

Tuesday, January 19, 2016

Two More Down

After my fantastic call with Red, I decided not to prolong the inevitable with two other potentials.

Natalie got a text from me around 10 p.m., after she goes to bed. "Just wanted to send a quick note to let you know that I'm no longer available. I really wanted to make it work, but dates after work hours just doesn't fit in my schedule.  My family needs me to be home nights, and I love them too much to sacrifice that time. I know you understand. Sorry.  I enjoyed getting to know you and our brief time together.  All the best."  I got no response so far today.

The SB who didn't deserve a name got less of an explanation, just: "I've decided to keep looking. No real issues with you, but I just want to be completely satisfied."  She wrote back some rambling, sour-grapes response that she didn't want to be a Sugar Baby anyway because it went against her values. OK.

My next let down is Kona, who will hear from me tomorrow after I confirm with Red.

Reason #4. I Met Someone Else

A few days ago I wrote about a brief introduction to a woman I called Red. I gave her my number but didn't hear from her right away.  A few days later, however, I did get a text and we started a brief conversation, including revealing our real names.  As I was just about to sit down for lunch with one of my kids and a couple of friends, I excused myself and told Red I looked forward to talking with her later.

After the texting exchange I had with Ally when she made that rude ethnic joke, I reached out to Red, but she didn't answer.  She had suggested in our initial messaging a per-meet allowance that was exactly what I would have offered her, so I repeated that I was fine with it.  But no answer.  A couple of hours later I asked if we were still going to chat about meeting.  She replied that she wasn't sure about me.  I then asked if I could answer the question she clearly had.  She then wrote, "I've figured out who you are and I'm not sure why someone with a history of law enforcement is looking for an arrangement." She obviously had me mixed up with someone else and was concerned that I was perhaps looking to arrest someone for soliciting.  "I have zero history in law enforcement. What gave you that idea?"  I then shared the industry I worked in. She replied, "Your number is linked to a company [in my industry] and the "Porter" that works there has a history of 25 years in law enforcement."  "Um, no," I wrote, "I have 30 years in [this industry]."  I asked her to send me the link.  She replied with the name of the person, who shared my first name.  "That's not me," I wrote. She identified the company as one of my former employers.  I Googled the guy's name and pulled up his company webpage.  Different face, bald, different phone number, different part of the country!  I texted her a screen shot, along with a recent pic of myself with my full head of hair.  That was the end of her concerns.  I then asked to see a picture of her face.  What followed blew me away. I may have initially named this girl Red because of the lingerie she wore in her profile picture, but she also happens to be a stunning redhead, with warm and inviting brown eyes.  Flawless and classic beauty! We texted for a few more minutes after she graciously thanked me for complimenting her.  She said she'd had one prior arrangement.  "I was a mistress for a couple years.  It was lovely.  It ended when I moved [to our city]."  She also revealed she was an arts entrepreneur and was successfully building her business. When she asked about my prior experience, I decided to seize on an opportunity.  I had 20 minutes to kill before I had to be somewhere, so I offered to call her so we could talk.  During our chat, I let her know some of my prior experience.  We had some good laughs about a few things. What shot Red to the front of the line, however, was that she explained that she doesn't really like the term "sugar baby" and that she preferred mistress.  Those of you who read this blog from the beginning know that I have never really liked the "Sugar" terminology, but later learned to use them because they generate clicks and site visits (though not many, unfortunately!).

Red revealed that her previous arrangement was more of a relationship, and that she "loved him very much," and was still good friends with him.  He was older than I am and their age difference much greater than mine was with C/Hayden. Overall, she exuded a warmth that I have seen only rarely since beginning my sugar journey.  Most of the girls I've actually met were nice, some not so nice, but only a few -- C/Hayden, Rachel, Dale, Joni, Natalie, and Wanda -- really impressed me with their charm and grace.  As I really want to stick with women who I can see as an equal, Red appears to be that type.

We arranged to meet this week for coffee near my office.  We have agreed that, should the chemistry we felt over the phone be matched when face to face, to continue our date in a nearby hotel.  I'm concerned about the first-time failures I've had.  I will keep my eyes wide open, and I will not be afraid to say no to moving to a hotel if I don't feel 100% sure that this won't be a one-time thing.

WCSD Journal Sugar Update, 1/19/2016

Ally is out.  We exchanged texts and pictures for a week or so, but in the end I got turned off. There were four reasons for this:
  1. I couldn't help but feel that she might be older than she said in her profile.  I Googled her phone number and found out her real name and looked up her website for her work. When it said that she'd been engaged in her highly specialized line of work (something that almost always requires at least a Bachelors Degree if not an MBA) for nearly 13 years, I had to conclude that she was at least 35. She said she was 30.  In and of itself, her lying about her age would not have been that big a deal (I'm lying too), except for the fact that...
  2. I wasn't really all that knocked out by her physical appearance.  I mentioned earlier that she sort of looks like an older version of Sam (who's in her mid-20s) but the more I looked at her face, the less I saw Sam's face, and the less turned on I was. A beautiful face is kind of a must for me.  She was highly sexual so that sort of overcame what I saw as her average looks (I also never thought Audrey had been a serious beauty but her very cute face and her hot sexuality had really sent her over the top for me).  I concluded that her profile pictures were not recent at all (she said they were from a year ago), and that the recent ones she sent me were less than totally flattering (and all the nude ones were shot from quite a distance and in the dark, so it was hard to make out any real details). Over the past weekend she flew out of town to visit and fuck two women and another man (at the same time).  Not criticizing her sexuality, but the idea of fucking her so soon after that was a turn off.  She sent me pics of her and one of the girls lying in bed, right after sex, kissing each other and a close up of them "scissoring" each other. Kind of hot, but also kind of not.  Funny enough, she had flown to where I was with my family for the long holiday weekend, so I could have taken an Uber car to her hotel within an hour had I been able. She offered to give me a threesome with the girl in the picture if I agreed to fly her to our city and give her the same "gift" that I was giving her.  I declined, politely, saying I preferred our first date to be just us.
  3. She seemed to take some pleasure in verbally humiliating and/or abusing me. As I was planning our date, I sought her input on the choice of hotels.  She said where she wanted to meet up, neighborhood-wise, but I didn't like any of the choices there (most were either far too expensive or poorly reviewed), so I asked her if there was any other city she had in mind.  Her other suggestion was too far to drive.  I guess she got annoyed with me, because she then made a derogatory remark about my ethnic background and being cheap.  I tried to dismiss it with a funny response, but it offended me.  Even though I didn't say anything else, she must have sensed that I was miffed and she sent a winking emoji.  I thanked her for that, but the damage had been done. She then sent a text to say that whatever hotel I picked, "make sure it's not one that is gonna give me bedbugs."  That felt like another insult and I was pretty much convinced I was going to cancel.
Last night I texted her that I was out.  I told her I had been initially very excited to meet, but had felt increasingly uncomfortable, less-than, and pressured.  "Not the way I want to begin this.  You need a more high-end guy, and that's not me."  We wished each other luck and moved on.

My gut has perhaps been on high alert of late, given my recent string of disappointments.  But I'm glad that I'm saying no more often than yes.  I really want to find a partner who thinks like me, wants what I want, is easy-going and warm, and sees these arrangements the way I do.

Oh, by the way: for the fourth and final reason, you're going to have to read the next post.

Thursday, January 14, 2016

WCSD Journal Update 1/14/2016

Kona and I were supposed to meet for coffee yesterday afternoon, but I'd double-booked.  A co-worker and I who successfully closed a big deal last month had scheduled a Happy Hour drink yesterday. She's a very cute Asian girl, with a perfect smile and a seriously curvy body, and a single mom, and I'm attracted to her.  So I texted Kona and we rescheduled for next week.  Might still cancel.

Ally and I continue to exchange texts. We're trying to make time to meet, but it's been difficult.  I'm leaving town today, and when I get back, she said she'll be on her period.  Then she leaves for 10 days.  The earliest we'd be able to meet is early February.  I'm not yet taking this as a sign that we are incompatible.  I think it'll work out, but we'll have to get over this hump first.  She has been 100% clear that she will never invite me to her house for a date.  "My space, and I guard my privacy," she said.  It'll have to be hotels.  "Cheap ones," I joked, "with porn on the TV."  She likes that idea and suggested a few in her area that are newer.

Stephanie and I are also struggling to find time to meet.  With her living in northern California, it's probably going to be a challenge, but she's cute enough to check out.

I got a note back from someone I call Red (the color of the lingerie she wears in her profile pic) who suggested terms that match exactly with my standard offer, but she also suggested a casual meet then proceeding to "your place for a playdate" if we click.  As I'm no longer interested in a meet 'n fuck, I'll see if she'd be OK with delayed gratification.

A couple of other girls bubbling under the surface, but nothing to write about yet.

A woman I follow on Twitter, who happens to be an "elite companion" (she calls herself an "intimacy consultant" or something like that) dabbles in porn on the side. I've seen a few of her videos and she is pretty fucking hot.  She just announced that she'll be in town for her shoot beginning next week, so I went to her website and requested a booking while she's here.  Her rate is more than I invest for a date with a Sugar Baby, so I'm hoping she's worth it.  If she gets back in touch, I'll update.

Going offline till next week.

Tuesday, January 12, 2016

WCSD Blog Update 1/12/16

Natalie texted me this morning and wished me well on my out of town trip this weekend, but didn't express any desire to meet up the following week.  Now that the ball is in my court, I will have to make the next move.

Sam and I texted last night and things are still murky, but I know I can call her whenever if I want.

Kona and I are meeting for coffee late tomorrow afternoon by her place.  She agreed to terms, and I tried to give her a few opportunities to back out.  I told her that I preferred women older than her, but she didn't care.  Weird.  I have no expectations that anything will develop there.  My gut isn't yet telling me that I'd be wasting my time.

I postponed my meet with Sofia because my gut was telling me she was only marginally interested. She didn't acknowledge anything, so she's out.

The SB with no name and I had a bit of an argument yesterday.  I haven't yet ended things.  I sent her a link to an article titled "How to Save Money When You're Young, Dumb and Broke." She asked if I considered her all those things, to which I replied, "No, not dumb at all."  She agreed with the rest, and I recommended the article as a pretty good summation of steps she can take to become more financially literate and responsible.  Mentorship, OK?  Her response: "And if I don't will I get a spanking?"  I didn't want to play the game too long, so I sort of pushed the envelope: "No, you'll just have to get on your knees and suck my dick."  This was a mistake, and I see it now.  Should never have gone sexual.  "That could be arranged," she replied.  "Slut," I said.  "I don't see you complaining."  "Meant it as a compliment."  "I enjoyed sucking your huge dick."  Now here's where I got a little upset: "Unlike most men, I am not fond of being reminded about the size of my penis." I'm telling the truth, right?  "OK, but you mentioned your size and girth first before we ever met."  This was untrue and I reminded her of my exact text. "You seem to be in a bad mood," she wrote, "take care."  I wasn't in a bad mood, just sensitive, "Texting sucks," I wrote.  And she agreed.  But that was the last of it, as I got busy and didn't want to continue with a useless argument.

Ally and I tried to squeeze in a coffee date this week, but it didn't work.  I called her and we got out our calendars and now we're inked for next week.  Again, this will be casual and I will not fuck her the first date.  My gut tells me she's the one.  Her pictures have been hot.  Honestly she looks a little like Sam, just a bit older.

Mel asked me, after I texted her that I wanted the first date to be casual rather than sexual, what I had in mind.  I wrote, "A meal.  Preferably lunch."  No answer back yet.

Monday, January 11, 2016

My Sugar Search, Updated

Here's a quick run-down of what's going on:

  • Natalie: sent me a text Saturday morning to say her phone died and she replaced it (hence why I hadn't heard from her all week). She offered to meet me this week on days when I'm not available, so I let her know that.  She didn't respond.  If there is no further communication from her for another week, I'll cut her loose.
  • The SB with no name: sent me a text the other day that she was thinking about me being inside her.  I responded with an emoji.  She'll be gone soon enough.
  • Mel: let her know I was out of town this week.  Because of my recent decision to abandon the meet 'n fuck scenario, I texted her today to let her know that I wanted our first face-to-face meeting to be casual, that I want something lasting and that sleeping together right away has, for me, not been a recipe for lasting success.  So far there's been no response.
  • Sofia: meeting her today for drinks.  Gotta say that while I'm super attracted to her, the text exchanges have been fairly boring.  My gut tells me that she's in a hurry to find someone and isn't too particular about who it is.  Since I'm trusting my gut, I may cancel this one.
  • Young Asian Professional: In finalizing plans for our first meet, which was supposed to replace my meet with Sofia, the YAP asked for $100 just to sit down for a drink.  I have been very clear in previous posts that I do not cough up money to sit down with someone the first time, when we are both essentially auditioning each other.  I don't mind paying for drinks or a meal, but that's as far as it goes with me.  When she told me this, I felt very disappointed. She said it was because she was leaving soon to visit her family in her native country and wanted funds to buy gifts for them.  As I wrote in my post about the SB with no name, I have definite issues hearing about SBs who can't manage their money, and the YAP's reasoning felt like either bullshit or an indication that she couldn't manage a hundred bucks to buy gifts.  Coupled with her being available only after work hours, I decided to jettison this potential and thanked her for considering me, but that I no longer wanted to meet.
  • Anne: no update.  Probably not going to happen.
  • Stephanie: a new potential, from northern California who works in film production.  We want to meet but we're initially struggling to find a day.  After next week this should be less of a problem.
  • Kona: a new potential, an early 20s Hawaiian girl with a ridiculous figure and very pretty face. We've exchanged texts, she's OK with my terms, and we're going to meet this week for coffee. My gut is telling me that she's far more money-oriented than I like, so I'll feel her out at the meet and probably cut her loose once I meet...
  • Ally: a new potential, a very successful late 20s professional who works with money like I do. Her profile was so refreshing: "I don't need my rent paid, car, or school.  I'm a big girl."  She has an MBA and two undergrad degrees, owns a home, drives an Audi, and travels a lot for work.  Her posted allowance expectation was far higher than I was willing to go, but I decided to take the chance.  "I'd like to get to know you better, but my financial offer is not 'substantial,' or even 'high' or 'moderate.'  Perhaps you're out of my league.  Don't want to waste your time." She responded that she was interested and asked for my offer.  Usually I throw out some bullshit that I prefer to discuss that face to face, but with a high-end SB I throw it out there. The worst she can say is "no." I made my offer, and I wrote, "No thank you is a perfectly acceptable answer." She agree to the terms and we started chatting.  (That Chats with Ally have gotten off to a great start. We started with emails, where we traded additional pics.  She's as tall as I am, brunette, with green eyes and a curvy but slender figure. A former model, she's also preparing to open a retail fashion store.  She was the first to go sexual, saying that I had a good chin for giving head.  She wanted to text, so we exchanged numbers. The text conversation was not overtly sexual, but definitely hot and seductive, and lasted for about two hours that first night.  The next day she was off for a day trip to the snow for skiing, so we spoke on the phone while she drove up.  I know, right?  So unusual!  The chat lasted about 45 minutes before I had to go, but we agreed to meet in a week for a drink. There is definite attraction there, but I'm really glad that we're not going to jump into bed right away. I even told her that I don't fuck on the first date, and may even hold off on the second date too. If there's something there, it'll be worth the wait. However, I want to trust my gut more than my head, and my gut was telling me to cancel Sofia and meet with Ally instead.  

Sugar Daddies and First-Date Sex

Those of you who have read my blog all the way through (thanks!) know that, in between the six-month relationship I had with CC, the three-year affair I had with C/Hayden, the ten months I spent with Jade, and the 15 months I enjoyed Audrey, I had a fair amount of one-time encounters. Sometimes, these "one and done" hookups happened on another day after a casual meet over lunch, drinks, or coffee. A few examples include Space Cadet, Kyra, and Cha-cha.  Sometimes, the one and done was an intentional one-off occurrence, like K-Bear, or Nikki, or Chica.  In nearly all these cases I had a decent time but something didn't quite click for me.

But sometimes, I would have what I now call a "meet 'n fuck" that wasn't really supposed to happen that way. Readers might not know it, I prefer a casual meet up front, followed by text or phone calls, before we decide whether or not some physical chemistry exists.  Some of the best sexual encounters I have had began over coffee, followed a week or so later with a hot session.  What I've noticed lately, however, is that the ones where I went in with full intention of a longer-term arrangement but ended up sleeping with them on the first date usually turned out to be a failure.  Here are some that fit this model:

  • Anita -- my first sugar encounter that started with lunch followed later that afternoon with one time sex in a hotel.  I got a case of the guilts afterward and backed off.
  • Susan -- I had initially thought she was an escort, but I had a choice between her and Space Cadet, who eventually won out.
  • Joni -- while winding down from C/Hayden, I had lunch and then sex with this great Jewish girl from New York, who had recently moved to town. Best blowjob I'd ever gotten.  But my head was not in a space to take it slowly and I overwhelmed her with neediness and it fizzled out after the first date
  • Song -- this Korean girl came along at the same time as Wanda.  I had a choice between the two, and Wanda won out because she had been introduced to me by C/Hayden.
  • Mouse -- this cute and smart girl had pictures that were far more flattering than she actually was; she was also a dud in bed, so I decided not to continue.
  • College -- this young girl was supposed to be with me for six weeks before she went off to college, but I didn't want to stretch logistically to accommodate. 
  • Fleur -- this Asian woman was older than she said she was, and a total disconnect in bed.  Buh-bye.
Finally, there was my last encounter with the SB who will have no name.  She was less attractive than her pictures indicated and we didn't really connect in bed. Plus she was a smoker and that totally turned me off. 

Now, to be fair, there were two such meet 'n fucks that lasted.  I had dinner with CC and fucked her the same night.  I had lunch with Audrey and we fucked right afterward (there was, however, a two-month gap in between our first and second dates while I played with Leah and Belle).  But they were exceptional: I had far lower physical standards before my three years with the stunningly beautiful C/Hayden, and the gap with Audrey sort of feels to me like we'd started up again rather than resumed.

One pattern that seems to have emerged in the post-C/Hayden era is that I'm jumping into bed with girls to whom I'm less attracted. Three of them have happened in the past year alone.  I'm really not happy with this.  Also, even though Rachel and I met first for lunch and got together on another day, I was also less attracted to her up front and not too knocked out with her once I saw her naked. Finally, there is a good chance that Natalie and I will not continue due to logistical challenges.

Taken as a whole, I feel like I'm in a rut and I need to take action to get myself out of it.  After reflecting on it over the weekend, I've decided that I will neither suggest nor agree to sex on the first date.  If I feel there's a real connection with someone, I might even delay sex until the (gasp!) third date.  Proceeding more deliberately and carefully seems to me to be more protective of both my psyche and my wallet.  Plus, I'll be leading fewer women on with expectations of something that won't be there.

In my next post I'll have an update on my search for the next Sugar Baby.

Saturday, January 9, 2016

A Re-Post from 2014

Given the feedback I've gotten lately from some readers about how I treat SBs like hookers or de-humanize them, I thought it might be an opportune time to re-post this tidbit from about two years ago.


There are many who argue that this whole Sugar Baby/Sugar Daddy arrangement shit is nothing more than a more subtle form of prostitution.  Essentially the argument goes like this: if a woman agrees to have sex with a man in exchange for money, gifts, dinners, trips, etc., she's a hooker, full stop.  If a man gives a woman any sort of valuable consideration in exchange for sex, then he's a john (I used "hobbyist" in the headline because that's what men who frequent hookers call themselves), full stop. 

I'm sorry, but these arguments are simplistic because those who make them are thinking one-dimensionally.  Further, I would wager that most if not all of them who hold to these arguments with certainty have never been in a Sugar relationship.  As someone who has been with both escorts and Sugar Babies, I know the differences, and they are vast.

First and foremost, when I would engage in sex with an escort, I never gave more than a momentary thought to who they were as people.  For me, they were selling a product and I was a buyer of that product.  Once in awhile, I'd meet an escort and enjoy a bit of conversation over some subject or other, but it was no more meaningful a conversation than one I'd have with the person checking my groceries, or fixing my car at the local garage.  The conversation passes the time, and nothing more, until both of us decide that the transaction has ended (usually when the next person in line gets annoyed enough!).  With my sugar babies, I nearly always spend just as much time (if not more time) conversing than fucking.  This is a huge difference to a hobbyist, who pretty much just gets in, gets off, and gets out.

Second, with nearly every one of my sugar encounters, even the one-offs, it was important for me and her to get to know one another before we hopped into bed.  On her end, she is looking for a man with whom she can feel safe, who shows some measure of charm and who is passably attractive to her. While I wouldn't go so far as to assert that we're looking for shared values, if we discover that there are shared values, it makes things so much better.  Because, in the final analysis we are looking for a relationship, not engaging in a business transaction.  Anyone who has read this blog from the beginning knows that these women are people to me (unless I get very mad at them or feel particularly sorry for myself when I get manipulated by them).  When I saw escorts, they were fuck-toys, some with better personalities than others.  I was with some really sweet escorts, and I encountered some horrible girls too.  But so what?  Here's your money, open your mouth, spread your legs, get me off, and thank you very much!  This was the arrangement, and was always understood.  No escort I ever saw ever complained that I wasn't a gentleman or an otherwise decent customer (especially those I saw more than once or twice).

Finally, while I haven't experienced this yet, I have read accounts of Sugar Daddies who have maintained friendships with their Sugar Babies long after the arrangement had ended.  I would like to have this kind of relationship, particularly with Leah or with C.  There isn't an escort I ever met who hoped to be able to see her customer as a friend after their transaction ended, and as a hobbyist I have never expected an escort to offer me her phone number so we could get together for coffee or a walk on the beach.

But there is an element to the simplistic argument I noted above that does resonate with me: every one of us, men, women, sugar or not, is a prostitute for something.  We have all sold ourselves at some point in our lives in ways we wished we hadn't in exchange for some needed and worthwhile benefit.  Those who reject that argument are liars.  Many of us have worked jobs we hate because we needed the paycheck.  We may have done business with a rude customer because the financial rewards were worth it.  Some women have remained in marriages with husbands who ignore their needs because a) there may be a status element to the marriage, or b) they have no marketable skills and could not survive on their own.  She may even have grown to loathe her husband over time, but because he makes a great living and she gets to have enough time to hang with her girlfriends, at the gym or over lunch at the country club, and they get to travel to nice resorts or on luxury cruises, she crawls into bed with him and puts up with his "three-minute mile" until she can watch The Tonight Show or a DVR of "Modern Family" after he falls asleep.

The final point I want to make is this: sex work need not be bad.  The simplistic argument above implies that it's a horrible thing to be likened to a hooker.  I've read enough accounts of sex workers who feel empowered to use their bodies and sexualities to be able to finance their way through school or make up for a financial shortfall when the job doesn't pay the bills.  If it goes well, everyone "comes" away happy; what could be bad about that?

Readers Get Pissed!

A reader sounds off on my post about the no name SB:
The fact you didn't give her name, to me, shows dehumanization. It's like you don't warrant her as a person. All your other encounters that lacked your expectations were still worthy enough of a name. If you are already planning to cancel it just do it already. Don't wait until next week to come up with an excuse, or string her along since she's already sending messages of wanting you. You were clearly not happy with the encounter and already started writing her off the second you realized she wasn't a perfect body type. I'll ask the same question I asked before in other comments of posts: Are her flaws really negatives? Or are they excuses your mind makes to help you feel better about breaking it off and making it easier on you to do so?
I notice a pattern of you having one dates and then tossing them aside for one reason or another. Try to give them another chance and don't let the previous experience be the judgement of the person, or the activity, alone. It's good that you are seeing the pattern of the one-meet & fuck. Do you think (or see) it changing in the future? Perhaps you jump into the sex too fast? 
The reader is clearly not deciphering my intent here.  My desire is not to reduce anyone to a non-person.  As the fourth consecutive one-and-done Sugar Baby,  it simply doesn't matter what her name is.  She's simply in the wrong place at the wrong time.  My intent here is to show that my consciousness around how I'm treating these people, and how I've been playing the game, has reached a turning point.  Her anonymity is merely symbolic. 

This girl still wants me,  as evidenced by a text she sent that she's been thinking about me being inside her.  Maybe that's just SB seduction talk,  but maybe it's not.  I'm not going to string her along, I'll end it early next week.  I'm like most people in that I don't care to be fired on a Friday night. If there was the slightest possibility that she'd be affected I wanted to avoid that.  I'm fresh off getting deeply wounded by Leah.  I don't want to do the same to another.  Whether I do it immediately or in a week,  I'll take care to do it honorably. 

I will reiterate something I wrote a while back: As a Sugar Daddy, and as a man, I want the best possible Sugar Baby my investment will attract.  That means I'll be meeting with,  and possibly sleeping with,  a number of women before I find the right match.  I don't apologize for how this may look to some;  it is one of the perks of being somewhat desirable in the sugar community.  My latest string of failures,  however,  has me beginning to rethink how I go about this,  and I'll share about that more in depth in another post. But a woman's physical flaws are not excuses;  they are the qualities I find unattractive and supportive of my decision not to continue. 

I find the idea of giving second chances to some girls to be compelling.  Natalie may be one deserving of another chance;  the ball is in her court and she owes me a text to let me know when she's next available. If she forgets or ignores my request,  I'll have something on which to base my decision to move on from her. But with Rachel's or the last girl's flaws,  and sorry if they're physical but that's part of why I'm in this game,  there's no need for second chances.  I'm actually sorry I ignored my initial impression with the last girl, and saw some of Rachel's negatives up front but saw lots more to like.  Sometimes I don't know if I'll like a girl till I see her naked.  Call it a flaw in the program. 

I do appreciate the challenges my readers place before me.  I'm a work in progress and I don't  characterize what I do as exemplary.  They're just my experiences and I'm honored to share them.   

Friday, January 8, 2016

New Sugar Baby Searching

A quick update on what's going on with me in the Sugar Bowl:

  • You know about my most recent adventure with the Sugar Baby who doesn't even deserve a name. Today she texted me that she had fun, with a little smiley emoji, to which I replied, "Yes. Definitely."  Next week I'll let her down with a text that says thanks, but I'm going to keep looking.  Pretty sure she'll be expecting it.
  • Natalie -- This should have been the week for our second date, but she was too busy with work, and I was stupidly obsessed with trying to hook up with Leah.  I texted her earlier this week to find out what next week looked like for her.  No response.  Not sure what that means, but I certainly can use her non-response as a reason for calling it off.  Since I sent the last text, I'll wait for her to respond.  If she doesn't I'll take that as a sign she's moved on.
  • Sam -- She's out of town on a shoot till next week.  She's always a back-up plan if need be. The fact that I keep looking for others tells you a little bit about why she's always a back-up plan if need be.
  • Mel -- I wrote about her a couple of months ago. I'd actually made and canceled two dates with her (mostly because I like other girls more), but she was still open to meeting on just a couple of hours advance notice.  Since what she's angling for is to meet for sex, I'm going to hold off with her because it is so common with me that first-date fucks are one-off encounters.  And I most decidedly do not want one of those until I'm settled into an arrangement.
  • Rachel -- I had one date with her before meeting Natalie, and I decided not to continue because of her physical negatives.  I have not contacted her again in the past several weeks, and I'm sure at this point she knows I've moved on.  While I do not like that I was not up-front with her about it, all in all it seems to have worked out fine.
  • Young Asian Professional -- not giving her a name yet because frankly I can't think of one yet. Early 30s accounting professional and grad student who probably makes more money than I do (or will soon).  Her profile indicates that she's way out of my league, allowance-wise, but I'm the type who believes that one never knows what one can achieve unless one goes for it. So I contacted her two months ago and we exchanged some messages on the website and shared a few pictures.  She's gorgeous and articulate, and I used my charm (read, bullshit) to see how things would go.  She put me off till now because she was neck-deep in year-end work, but when I looked her up earlier this week, she texted me and we're meeting for drinks next week. She has agreed to my terms as well, so despite my somewhat accurate reservations three years ago about me and Asian women (this was slightly before Jade entered my life), I'm hopeful that there might be something there.
  • Sofia -- late 20s South American hottie.  Looks like Sofia Vergara, hence the name.  So far it's been pretty superficial, but we're meeting for drinks next week.  She was pretty assertive in wanting to get together.  Usually a Sugar Baby will do that when she feels a sense of urgency, as in she needs money fast. I have my guard up with her.
  • Anne -- mid-20s blonde from Florida. She has had one arrangement and it was exactly like the ones I have: bi-weekly, semi-monthly per-meet allowances.  She said she enjoyed it and then he moved away.  Seems a little down so I'm cautious.  No meetup set yet.
There you have it. My next post will be about my history with first date fucks.

This Sugar Baby Doesn't Even Warrant a Name

Yesterday I met with and fucked a young woman I'd met on the Sugar Daddy website.  I won't even give her a name, because there is no way I want to remember her.

She and I started exchanging messages a few days ago on the website, and I gave her my cell so we could communicate more efficiently, and because, well, if I want to have an arrangement with someone, that's how I start the process.  She was a cute blonde, in her early 30s, who put "management" as her profession.  The text exchanges did, in fairly short order, start getting flirtatious, and culminated in her sending me two very cute pictures (face hidden, of course), one of her booty and one from the side that showed her breasts.  Let's just say the pictures gave the impression of a very skinny, in-shape woman with some nice curves.  At 5'6" I'd have said she weighed about 125 pounds.  She lived about 10 minutes from where I worked.  We agreed to meet for lunch at a restaurant in my office complex, and I let it be known that I might be interested in taking things further.  I got to the restaurant a little before she did, and I saw her exit the Uber car she took from home.  She wore all black.  She did not look very skinny from a distance, but I attributed that to the thick coat.  She came a little closer and I could see from the leg she was showing that she was most decidedly not skinny, although she didn't look bad at all.  I wondered if the pictures were accurate (and I actually asked her if they were recent, which got a not-too-pleasant response, but more on that later).  We hugged, got a table and started chatting.  She spoke with a lisp.  Definite turn off, but not a huge one.  She said she had attended college in Paris for fashion design, and was now working in retail management for a multi-billion-dollar company that designs and sells high-end accessories (I won't give away the company name).  She came from a wealthy family and lived pretty comfortably.  We had decent rapport.  She wasn't the prettiest girl I'd ever seen, but I liked her and I thought perhaps that there might be something there.  In my gut, however, was that familiar feeling of "Really, dude? You want this one? You can do better!"  In any event, we discussed arrangement terms and she was down.  She told me that she was also down to get together later, as her afternoon/evening plans had fallen through.  I had maybe two more hours at the office and I would be available, and there was two great hotels within walking distance that we could use.  Against the inner voice I decided to go for it.  The cash I'd reserved for Leah earlier in the week was there, why not use it?  I paid the lunch check -- $80 -- and we started heading out to the restaurant.  Looking at her as she put on her coat, I realized that she was definitely not skinny.  She carried her body very well, very much like Dale.  We hugged again and I headed back to my office.

BIG MISTAKE.  I reserved the hotel -- $120 -- and met her there around 4, thinking we'd play for a couple of hours and then I'd drive home.  She walked in on time through the room door I'd left unlocked.  She'd changed into a long sweater, which came off very easily.  I tasted the fresh mouthwash on her breath, but once that was over, the faint odor of cigarettes came through. We got on the bed and kissed a lot more.  A very good kisser.  But I had to ask: "Are you a smoker?" "Wellll," she replied, "I had one. I know I shouldn't smoke, but I was nervous coming here."  I logged it in as a negative.  Her body was very responsive so I at least enjoyed that.  Lots of rocking hips as we made out.  We got naked and I went down on her.  I thought she had a great body, despite her size.  She probably weighed about 145-150 pounds.  Big booty, big thighs, but all firm.  Flat abs and really nice breasts.  She had a great orgasm.  Then she gave me head, which was very nice, but there were a couple of comments about my size.  Another negative, I thought.  And the tobacco taste was getting stronger as time passed.

Fucking her was uneventful.  She didn't come at all, probably nervous, and when she got on top we could not sync up.  She asked me to turn her over and I came inside her that way.  I took off the condom and cleaned up. While in the bathroom I looked myself in the mirror and quietly said to myself, "This won't happen again, no way," and then joined her back on the bed.

Her life, despite outward appearances to the contrary, was a mess.  She had a great job with a high five-figure salary plus bonuses, a nice apartment, luxurious material things, and did a lot of travel, but she was neck deep in debt to pay for it all.  We're talking tens of thousands of dollars in credit card debt. She also has zero savings and is putting aside only the minimum amount into her 401k.  As she is in her 30s, she is way behind having enough to support herself later on.  She is one of four siblings, and while her parents are doing well, that's an estate divided by four once they both pass on.  I wrote nearly six months ago that SBs needed to take care of their money.  I was a homeowner at 28 and started saving for retirement before then.  When DW and I got married it kicked everything into high gear and now we're sitting on more than $1 million (and it still isn't enough given the need to send two kids to college later on).  She is single, doesn't want to get married and doesn't want children, so there is that in her favor in terms of having more for herself, but she needs to get started now.  As someone who works with money, I am keenly sensitive when people don't get started with savings early in their lives.  It has tremendous ramifications that younger people just don't see, or think they can catch up later.  They can't, trust me.

Anyway, my frustration with how she was mismanaging her money, coupled with my dismay that the date was another one-and-done, I was less than delicate in the way I talked to her.  I actually said at one point, "And now you have to fuck me for cash to pay off your debt."  She looked away at that point and I knew I'd offended her.  I apologized for the remark, and said, "I know there are other reasons why you do this. I've just met too many like you who would rather meet men some other way."  She acknowledged that my remark bothered her but she accepted my apology.  We kissed some more and I went down on her again, and she had another orgasm.  I put on another condom and started to lube it up, but she asked me not to because she said that some lubricants irritated her. Knowing what I know about lube, you can't not use it when you're using condoms.  Combine that with my penis and it's not going to be too comfortable.  She wasn't enjoying herself while I was inside her and I pulled out and stopped.  I reassured her it was alright, but inside I was so done with her.  Just before we fucked again, she looked at the clock next to the bed and said, "I have to go in 15 minutes," and that her previously canceled plans were suddenly on again.  I would have been unhappy with a more pleasant girl, but it didn't bother me at all.

She washed up and got dressed.  I kissed her lightly and thanked her, and she left.  I hung out for a few more minutes, got a call from one of my kids who was out of town, and then left the hotel.

So let's recap: bigger/heavier than I prefer, decent body, decent skills, a smoker, and cut the date short.  Depressing, and done.

Driving home I thought a lot about how often I meet a girl and fuck her on the first day (despite the fact that I tell most girls I don't fuck on the first day).  It bothers me that I don't stick to my guns.  In my next post I'll recount how many first date fucks have failed to result in an arrangement of any kind.

Wednesday, January 6, 2016

Leah: Where I Failed as a Sugar Daddy

Leah canceled a date with me for the third -- and last time.  She has been permanently banned from my life, and occupies a prominent, though notorious, place in the dustbin of my former short-term mistresses.  Leah now holds the distinction of being one of my worst experiences, along with Dale and Wanda.

I woke up yesterday morning feeling a combination of elation and dread. I was elated that I would finally get to reunite with Leah, still one of the most beautiful women I've ever seen.  The dread, as I realized later, was my insistent gut telling me that she was all wrong for me, that she would never go through with this, that she would come up with yet another stupid reason not to get together.

Let me list the reasons she gave, either for canceling dates or for resuming an arrangement:

1) My texts were too frequent and it seemed like I was looking for a girlfriend, which she couldn't be.
2) Because she lived with her mom and stepdad, it was now "too risky" to get together with me
3) *my favorite* "I don't feel like it; it's raining"

That last one came yesterday with an "LOL" at the end, which made me think for a second that she might be joking. And I sent a text, "You're kidding, right?  I'm leaving work early and driving 25 miles in this weather to see you today."  After 30 minutes of no reply, it hit me that she wasn't joking. "I can't believe this is happening again," I wrote.

Then she wrote, "I'm sorry, but I guess I'm just over the whole sugar daddy thing.  It was a chapter in my life, but now I've moved past it.  I don't want to do it anymore.  Also I just started seeing someone and I don't want to ruin it."

Mind you, she'd sent me on New Year's Eve a gorgeous nude picture with the caption, "A preview of things to come in 2016."  Further, on Sunday evening I confirmed with her and she wrote that she'd be there.  As far as I was concerned, we were on.  How we went from that to a boyfriend and a complete one-eighty in two days was beyond me, and I called her on it.  "I don't understand why you thought it would be OK to mess with my head."  "Not messing," she replied. "I thought I wanted to."

"You changed your mind five times.  And you thought it was no big deal.  Whether or not you were deliberately fucking with me, I'll never really know. But what you did has really affected me.  It just seems so silly for you to use the weather as a pretext for all the other stuff.  Good luck, I guess."

I wish I could be angry with her.  Her behavior was immature, inconsiderate, and cruel.  What this says about her as a person is obvious. But it's all irrelevant.  I am far angrier at myself for not trusting my gut.  From nearly the beginning, my gut was telling me that it would never happen, never work, and never feel good.  And I distrusted it.  We'd had it good for a few weeks, after all; couldn't we recapture that?  I gave her too much credit because I wanted her to be an awesome Sugar Baby.  And for a second she was.

Like the fateful mistakes I made with C/Hayden, I made some big ones with Leah.  When I realized that I was friends with Leah's mother, I should have walked away. But I had to fuck her.  When I realized that I could not wrap my head around fucking my friend's daughter, I walked away and should have stayed away.  But I had to fuck her again.  When I walked away after fucking her again, I should have stayed away. But I wanted to fuck her again.  When I walked away after her stupid and insincere "too risky" excuse, I should have stayed away.  I should have stayed away!  But, like a fool, I persisted.  And I paid the price.

I need to say that I never regret anything that I've done while in the sugar bowl.  And I've met some really awful women over the past eight years.  But this?  I regret this.  Today I regret ever meeting her, I regret kissing her in that parking lot, and I regret fucking her.  I regret all of it.  And I'm the failure here.  I am.

*     *     *

Shifting gears, I have gone back to SA to find another baby.  I'll share my results in the next post.

Tuesday, January 5, 2016

Strike Three, Leah is Out

I texted Leah to confirm our date for today. Just two days ago she'd said she was ready to meet,  but today was different story.  At first she blamed the rainy weather, but after I dug deeper,  she said she'd started dating someone recently,  and had decided that the sugar bowl was no longer an option for her.

Whatever.  Strike three and she's out.  I wished her the best and deleted her contact information again.  What a disappointment this whole process turned out to be.

Feeling very stupid right now.  I'm going to take a little time to check in with myself and try to see where I fucked up.

Natalie is still there,  so is Sam,  so I can go with either one of them.  Or,  I can start searching again.  That seems like a good idea,  but not just yet.

Monday, January 4, 2016

Revisiting the Leah Saga -- A Sugar Daddy Reflects

My first meeting with the lovely Leah presented me with a dilemma I'd never before experienced. After nearly six years in the Sugar bowl, after several dozen potentials and three long-lasting arrangements (with CC, C/Hayden, and Jade), I had largely managed to avoid collisions between my life as a Sugar Daddy and my vanilla life. One of my unwritten rules was never to engage in extra-marital activity with anyone I knew (co-workers, primarily), but I went deeper than that.  I also had a rule not to engage with anyone who knew someone I knew.  The original intention there was to avoid the temptation to hook up with a friend of a friend.  The scenarios that played in my head revolved around meeting someone at a work party who was hot enough to want to play with.  But the idea of that friend letting my co-worker know that she'd slept with me was too unnerving.

I'd had just such an opportunity back in 2007, about six months or so before I made the decision to become a Sugar Daddy.  One night in fall of 2007, a number of people in my business unit decided to get together just to hang out.  The national economy was already tanking, our business had dropped off sharply, and in the backs of our minds we all knew that, as salesmen, our days were numbered. We would, actually, all lose our jobs about 60 days later.

One of the co-workers who joined us at this hang out was a young Latina girl in her early twenties.  I don't remember what her job was, but she was the talk of the sales team with her pretty face and fantastic figure.  One of my buddies, a co-worker who was present on the day I revealed my sugar relationship with C/Hayden, had a particular fondness for her.  The guy was about five years younger than me and was married with four kids.  He was very successful and lived in a very upscale, very white-bread town about 20 minutes from where we worked.  But he liked to drink.  A lot. And when he drank he'd forget himself.  He had his hands every place on this girl's body he could without it becoming too sexual.  She didn't seem to really mind, but someone else did.  Seems chica had brought someone with her: her older sister.

"Annamaria" was two or so years older and, at least to me, was far more beautiful than the younger one.  I was instantly attracted to her.  She seemed far more intense and a lot more intelligent.  We sat in the bar and talked for about two hours.  I only remember two things about that conversation: first, she openly disdained marriage, and kept pointing to my buddy's activities with her sister as evidence that marriage was meaningless if people just wanted to fuck outside of their marriages all the time. Second, she was unashamedly sexual.  The one thing she said that I will never forget was, "I've got to have my man meat."  I tried really hard that night to restrain myself.  I'd seen some escorts at that point, but I hadn't yet moved into sugar territory -- I hadn't even thought of it.  When Annamaria stood up to leave a couple of hours later with her sister, I knew I wanted to see her again, but didn't really know how I was going to make that happen.  I couldn't ask her sister to hook us up, right?  So I just accepted that this lovely girl was going to disappear from my life forever.

In the intervening two months, emboldened by something I really can't explain, I'd begun pursuing a co-worker.  Her name was B.  She was a Dominican bombshell, probably somewhere in her 30s.  We worked in the same business unit, but in functions that never had us working together on anything.  We flirted a lot, and I wanted to take it further. She actually seemed open to the idea, and we had lunch to talk about it.  I really didn't know what I was doing or how to go about making this happen, and she interpreted that to mean that I was a bit of a scrub, so nothing ever came of it.

In early 2008, I was laid off.  The company "re-hired" me as an independent contractor for some other work, but at about one-third the income.  I didn't want to be unemployed with a huge mortgage, so I took it.  I discovered in my first several weeks that Annamaria's sister had moved into the company's payroll department and had managed also to get a job for her older sister.  I did not want to waste an opportunity to see her again, so I emailed her and invited her to lunch.

Over lunch, I tried to persuade her to have an affair with me.  I promised her nothing in return for her sexual companionship other than my stellar personality.  It didn't succeed.  She wasn't offended, but I could tell that she was turned off by the idea of being some mistress.  For me, however, the whole thing was a disaster.  I imagined that she went to her younger sister right after lunch and told her of my offer.  Right after that is when my lovely DW suggested I find a girlfriend for sex.  But because of how badly things had gone with B and Annamaria, I made it clear that I wouldn't try again to hook up with anyone that close.

Jumping forward six years, sitting with Leah at the coffee shop and learning that she was the daughter of a high school crush of mine, I did not make the connection to my previous experiences with Annamaria or B to warn me off the decision to consider Leah as a potential Sugar Baby.  In hindsight, the fact that I knew her mother didn't put me off wanting to sleep with her.  Was it a disregard for my internal rules?  I'm not sure.  My thinking can be led by my dick as well as the next horn-dog, but I certainly thought it through the entire time, which was one reason why it didn't last beyond a month or so.

And again, in a subsequent post I noted that if DW found out that I was sleeping with a high-school friend's daughter the fallout would not be different than if she found out I was sleeping with someone random.  The result would be the same: divorce.  Thinking about it today, I'd probably have more to worry about from Leah's mother than DW.

In the two months since I'd started thinking about Leah again, a lot has happened.  Sarah was the first girl to hesitate to accept my financial offer, Fleur was horrible, Rachel  rocked in bed but I found Natalie more attractive, and now Natalie's lack of daytime availability is weighing heavily on my decision to continue seeing her.  A few of my readers have weighed in with some strong opinions. Many of them don't like Leah.  Based on my portrayal of her in this blog, I can understand why.  But this is only my side of the story, and while I can be unflinchingly self-critical, I don't particularly like to make myself look too much like a fool or a creep.  I made some mistakes with Leah, I judged her harshly, and because of my "rules" I deprived her of the chance to decide whether or not I was worth having in her life.  And from my perspective, I lost out on a pretty remarkable woman.

I have had two arrangements in the past seven-plus years that I would consider life-altering.  The first was with C/Hayden, and the other was with Leah.  Leah was the first I considered an equal in every way.  I was not used to being challenged on what I believed, and I have approached nearly every subsequent arrangement with a desire to be with someone I saw as an equal.  Audrey and Staci definitely fulfilled that requirement.  Natalie and Rachel too.  Should I get to continue with Leah I will definitely work hard to keep myself open to learning.

Both Annamaria and her younger sister are my friends today. Annamaria is happy in a long-term relationship and her sister is happily married and the mother of a three-year-old. B disappeared in 2008 and I haven't heard a thing from her.