Tuesday, May 31, 2016

Taking a Break

I hope all of you are enjoying happy and healthy times.

Sadly, the family emergency to which I alluded last week has resulted in the death of a family member.  A tragic accident has taken the life of DW's father.  He was a stellar man, a giant of gentleness, a kind and loving soul who made everyone around him feel like family.  We have been making funeral arrangements since his death, and the funeral will be later this week.  He was very well-regarded in his profession, and we expect there to be hundreds of attendees.

For now, I'm going to take some time off to attend to DW, our kids, her mother and sister, and other relatives who are understandably devastated.  He was not my father, but he was a tower of fatherly advice and support for me over the roughly twenty years that I've known him.  I will miss him terribly.

I've spoken to Aussie and let her know that I probably will not be seeing her for a short while. Gratefully, she has been very understanding.  With her working now, there may not be a need for my support. However, I will not be surprised if she decides that she needs to move on and find someone else.

This is not goodbye; I plan on returning to my activities and writing as soon as I can, but I am in no rush.  Grieving our loss, and my commitments as a husband and father, must come first.

Until then, please enjoy the rest of the blog.


Tuesday, May 24, 2016

Going Offline: Family Emergency

Have a family emergency to attend to. Won't be blogging or sugaring for awhile.  Keep me and my family in your thoughts.

Monday, May 23, 2016

Mine is Just One Sugar Daddy's Journey

A reader suggested I write a post with lessons learned, tips, etc.  Every once in awhile, I learn something about myself and I pass it on to you readers, thinking that perhaps someone will derive some benefit from my experience.  That one time, for example, when I opened up to my buddy Luke about how long I'd been engaged in the sugar lifestyle.  Or that time when I explained how men need good bullshit in order to get laid on a regular basis.  Or the seven things that should go into an effective sugar dating profile.

In reality, however, when I look back at the totality of my 8+ years as a Sugar Daddy, one thing is consistently true: I have no idea what I'm doing.  It's true! From being self-assured to being a completely insecure little boy, from a scheming manipulator to a vulnerable man in his power, I swing wildly all over the place instead of playing it consistently one way.  I suppose that volatility is more of a reaction to the consistent drama and unpredictability that accompanies every sugar relationship that I have.  But a lot of it has to do with the fact that I'm just figuring this out day by day.

This blog helps me as a Sugar Daddy, as a husband and father, and as a man, navigate the treacherous road of a compartmentalized life.  I get to read back what I've written, field questions and comments from my readers, and process all of it into posts just like this.

If I could distill my experiences down to a single lesson, it would probably be this: Above all, protect your Self.  Protect what you have, and be hyper-vigilant about what is at stake.  This lesson could apply both to Sugar Daddies and Sugar Babies.  I can honestly say that whenever I lost sight of the stakes, or acted cavalierly about anything, I've paid a price.  Sometimes that price was relatively small, but other times it had the potential to alter the course of my life forever.

Young women in the sugar bowl would be wise to remember that, much of the time, they are dealing with men who are in it more for fun than anything and really aren't very concerned with the damage they create in their wake as they pursue having that fun. Protect your emotional core, your body, and your future.

Men who engage in sugar should always keep in mind that they are dealing with other human beings, and that they should tread lightly in the lives of those others.  Protect your wallet, your family (if you're married), your business, and also your emotional core.

Both sides should be open, but be slow to trust. Be flexible and willing to compromise, but know your worth/value and never compromise who you are.

While it is called "Sugar Dating," it's not just a sweet thing to do to pass the time until it loses its flavor.  Sugar Dating has the potential to be life-altering and uplifting.  Like anything in life, we get out of it what we put into it.

Thursday, May 19, 2016

Sugar DATING -- Works for Me!

As she was a few weeks ago, Aussie will be down the street from my office for a facial early next week, so she invited me to lunch -- I pay, of course! -- which makes me think that we are really dating.  It's our week to get together anyway, so I'll probably see her twice.

I never did this with any previous Sugar Baby on a regular basis.  C/Hayden and I had dinner out three times, lunch twice, and drinks a couple of times.  I had just lunch once with Dale.  Never happened with Jade while we were together.  I took Sam out to dinner once.  I had lunch with Audrey once. And other than my lunch with Dale, these were all on days we had sex anyway.  And I was the one who suggested it.

I'm definitely in uncharted territory, and I love it!


I told Phoebe earlier this week that I was no longer available.  She seemed disappointed: "Oh...OK," she said, but in a few minutes she wished me luck and we were done.

Now that I have no other potentials to play with, it feels weird.  I found myself the other night wanting to reach out to Sam, to Leah, and even to (gasp!) Jade.  Something about needing a little jolt of excitement in flirting with a woman, or just chatting with someone I used to fuck.  Glad I didn't though.

The other offshoot is that I don't get to blog as often because my dates are two weeks apart.  I'm not like some other Sugar Daddies who go through dozens of girls every few months and rotate them (although I'll admit that sounds like a perfectly workable scenario for an old horn-dog like me!).

What else should I write about?

Monday, May 16, 2016

Settling In With Aussie on Date #4

Late last week I had my fourth date with Aussie.  We have now been in our relationship for two months, even though we were apart for the last four weeks due to my scheduling (as well as a brief detour with Gemini).  Despite the delay, Aussie and I still connected deeply, both sexually and otherwise.

I arrived right on time to Aussie's new place, a large, older, multi-building apartment complex located a couple of miles from the beach on a highly busy street with no parking.  She had me pull around the back because, as I found out, there was a massive parking lot behind the building and no reserved spots.  She'd planned to buzz me in so I didn't have to park on the street.  Still I found a spot on the street and walked in through the parking gate behind a car that had just pulled in.

Aussie met me in the parking lot, dressed in shorts and a tank top and looking casually sexy.  She threw her arms around me and kissed me and walked me to her unit, on the ground floor in the middle of the complex.

The place was tiny for a one bedroom apartment.  It looked like a studio that had been remodeled to make it two rooms.  The front part had a nice, but small kitchen, equipped with everything, even a dishwasher.  Next to that was a very small room where she had her desk/office, and a place where eventually she planned to put a large beanbag/couch.  There was no room for much of anything else there.  The bedroom was tiny, not big enough for even a queen-size bed, so she had a full/double instead, as well as a side table or two.  There were no carpets or rugs, so the place felt a little echo-y for me.

Aussie had the music blasting in the front room so no one could hear us.  Since I hadn't been with her in nearly a month, I was not going to hold back, so I was glad for the extra noise buffer.

Aussie was very excited, as I was, to have her own place.  I didn't ask about her rent, but now that she has started working she'd have enough income to pay for it.  As for her work, she'd been at the job for nearly three weeks and hadn't yet been paid.  She was struggling a bit with the legal paperwork so that she could be paid (remember, she is not a citizen and had to get tax ID numbers to be a part of the system).  Further adding to her excitement was the fact that the lawyer representing the bank from which she'd drawn her deposit on the last place, which had fallen through, successfully recovered about 80% of her money.

Now to the good stuff: we were playing about 10 minutes after I arrived.  I'd asked her how she'd managed without me for the past four weeks, and she reached into a drawer and pulled out two very decent looking vibrators.  She started using one of them on her clit while I kissed and sucked her nipples.  I also ground my dick onto her and felt the vibrator as well -- very hot!  After some very wet oral, I entered her and we fucked for a long time.  She had a contraceptive sponge inside her, which was cool, but still I didn't intend to come inside her.  Luckily the towel was handy, as she let loose with a huge squirt about 15 minutes in, coming in waves that had her collapsing on top of me afterward.  I wanted her to suck me off; I hadn't really unloaded that way in a long time.  She took her time and worked on me very steadily, until I was just about to explode.  She got me to the edge, but not quite, several times.  Ecstasy!  Eventually, as I reached the tipping point, I just grabbed my cock and hammered away until I came in her mouth.

We were both exhausted so we didn't have sex again but we held each other, kissed a lot, and stroked each other everywhere.  One thing we talked about which interested me was a disagreement we had over monogamy.  Aussie was clear that she was fine both with an open relationship or a monogamous one, while I couldn't commit to monogamy ever.  "I've never been monogamous in any relationship I've had," I said, "and I'm not going to change that."  She pointed out that, because I was sleeping with her in secret, I didn't have an open relationship with my wife.  True, I countered, but it wasn't as though we'd never talked about it.  This was pretty much her idea from the start, even though she had no idea that it was actually going on.  "Besides," I said, "if I weren't doing this, I wouldn't consider what I have in my marriage to be monogamy. What I have right now is celibacy, and I wouldn't be OK with that without having this outlet to meet my needs."  She agreed and the subject got dropped, but I appreciated the fact that she challenged me.

As I reflected on our date over the past weekend, I realized that Aussie and I could possibly go for a long time.  I am hoping that she and I last for the remainder of this year.  I'd like to take her on a trip with me at some point, though the odds of that happening are fairly slim.  In any event, we really like each other, we are comfortable hanging out, and so long as we're both respectful, there is little chance that this will end anytime soon.

Thursday, May 12, 2016

Aussie Date #4 Preview

This afternoon I'll be seeing Aussie for the fourth time.  Truthfully, I feel so excited to be seeing her again that I can barely focus in the office today.

Phoebe, although I find her very attractive, is now out.  I thought about it, and while I was leaning in this direction anyway, it's clear that I've got a good thing with Aussie.

Last night, as I took the dog out for our evening walk, I started thinking (as I frequently do) about C/Hayden.  For the first time since beginning my relationship with Aussie, I began to compare my experiences with the two of them.  At first I thought it was unfair to be comparing a relationship that lasted three years to one that's just gotten off the ground.  However, Aussie (and I) are in a much different space than C/Hayden was. For one thing, C/Hayden was only 22 when we met and far less mature than Aussie, at nearly 30, is now.  Another thing is that Aussie has so far shown to be far more emotionally open than C/Hayden, as well as far more sexually adventurous, and far more romantic and affectionate. No doubt life experience will allow that to happen more readily, but the seeds for it have to be there from the beginning.  I'd guess that Aussie, at 22, just had a more open spirit than C/Hayden did.  I wonder if C/Hayden, being one of a set of triplets (and for a long time, the tallest of the three), may have had some emotional trauma in her childhood that left her a little guarded. Maybe it was the culture in which she grew up.  I can't be sure, obviously, and it's all just speculation on my part.  But while I can recall that C/Hayden warmed up over time and was very affectionate while we were actually having sex, she was forever somewhat guarded and tight-lipped about her private life. Once she got sick in 2011, it was pretty clear to me that I was going to remain solidly on the outside and was expendable without much notice.  No judgment there, just an observation and comparison.

I don't yet know a whole lot about Aussie, but I do know that her upbringing was fairly fractured and there was divorce and serious estrangement between her parents, and between and among her siblings.  I think that, to some extent, her work in acting was a way to manufacture the kinds of deep relationships she wasn't getting in her life.  Whether that translates into how she holds actual relationships isn't yet clear to me, but I definitely sense gratitude, warmth, and an unselfish attitude. We'll see how things shape up in the next few months.


A reader recommends that I meet with Linda and have drinks or dinner with her, but no sex.  I think that's a wise suggestion, and I'm inclined to agree.  Given what I know, I am not confident that she possesses the tools needed to engage in a successful one-time-only hook-up and then maintain the relationship we have developed over the last year and a half.  I've seen how she spins out after she gets laid, and for the sake of discretion I just don't want to be someone who contributes to that in any way.  I sent her a quick note today, and she was disappointed and worked really hard to convince me otherwise.  I'm not changing my mind, and I gave her the choice to accept it or put our friendship at risk.  She seems to be choosing the latter.  But there are still three weeks to go before I leave, so perhaps she'll come around.

Monday, May 9, 2016

Aussie -- I'm Back on Track

After a month that saw me meeting with eleven different potential Sugar Babies -- and fucking one of them -- I have finally come full circle and found that Aussie is my girl.

Of the girls I met, two rejected me, I rejected seven, and one (Chic) just didn't work out.  I have not yet decided what to do about Phoebe, but my only two choices there are rejection and a one-time fling before rejection.  I'm leaning toward rejection at the moment.

Aussie possesses nearly all the qualities I find attractive in a Sugar Baby: sexually adventurous, emotionally open, physically very attractive, intellectually engaging, and financial somewhat self-sufficient (can't be fully self-sufficient otherwise why need me at all?).  She also has her own apartment, lives relatively close to my office, isn't financially or emotionally needy, and is available enough so that I can have regular conversations without being told I'm being intrusive.

If I had to list her negatives -- and here I'm nitpicking -- I'd say she is slightly plain-looking, and she hasn't yet fully opened up. But again, that's really stretching.  I find her very attractive, just not as attractive as some of the girls I've met.  And we've only been face to face five times (twice just over lunch, and three times in bed), so the emotional connection I want needs time to develop.  The seeds for that connection, however, are definitely there.  What I look for is a willingness to talk about whatever, a sense of gratitude, a slight vulnerability, and a practiced effort to keep ego out of the relationship.  Once I see all those things, I'll see that trust can develop.  Once trust is there, it becomes a real relationship.  At that point, a real emotional connection is possible.

This week, I'll be seeing Aussie at her new place.  I bought her a gift last week because I couldn't meet with her on our scheduled day, so that smoothed things over.  No cancellations this week, however.

I'm supposed to see Phoebe next week, and she still turns me on, but I've already found my girl, so it may just be rotten timing that prevents the Phoebe connection.


In three and a half weeks I'll be flying back east to visit family, but I've also set up a hook-up with Linda.  As I wrote last week, Linda and I have been corresponding for a long time via Google Hangout (I actually first wrote about her in late 2014).  While she and I have a cute flirtation going, of late I've been re-thinking the idea of sleeping with her.  I've been privy to some of her adventures with men, and how she shows up in those situations gives me pause.  I've already mentioned this to her, so even if she reads this there won't be anything new.  She was a long-time SB for one sugar daddy.  Their relationship post-arrangement has been a bit stormy, mostly around what she says has been his erratic and sometimes volatile behavior.  I've mentioned to her that, as a single woman, she needs to stand up for herself and put and end to it, but she won't, saying that it doesn't benefit her to do so.  I guess I can see that, but there's simply no excuse for allowing someone to mistreat you.  On top of that she shows a deep sense of insecurity, as though she's simply not good enough for the men she likes. Linda's a sweet kid, but I don't think she possesses the self-assuredness I like in the women I fuck. I'm not closing the door, by any means, but I'm definitely going to have to think about it. Even if she's three thousand miles away, she will at that point know my full name and that doesn't make me feel too secure.

Thursday, May 5, 2016

The Last Lunch -- For Now

Today I enjoyed the final first meet of my current search, with Phoebe.  She is the last in a long line of potential SBs who have sat across from me, either for breakfast, lunch, or drinks, post-Red: KC, Vee, Aussie, Chic, Sports, Gemini, Alena, Piper, Cecilia, Marlo, Ava, Ari, and Meredith.  That's 14 women in all.  I've slept with three of them: KC, Aussie, and Gemini.  I wanted to sleep with another three or four of them: Chic, Alena, Ari, and Meredith.  Add Phoebe to that list.

We met at the same place where I lunched with KC, Vee, Aussie, Alena, Piper, and Ava. We moved the time up half an hour to accommodate her day, and when we arrived, the restaurant was pretty empty.  Phoebe is a tall and very slender girl in her mid-20s, blonde with green eyes, and a beautiful smile.  I dug her intelligence, and we have a connection in that we're both in the same business. Luckily we'll never cross paths!

Despite being so rail-thin, Phoebe ate a pretty large lunch, which I found wonderful.  I love a girl with a healthy appetite.  Clearly she works out a bit.

Over lunch we chatted about the fact that she wants out of her job and to go to grad school to study psychology. She wants to work with addicts and at-risk kids.  Very cool.

We traded stories, talked a little about sex, and agreed we wanted to see each other again.

I walked her to her car and then kissed her goodbye.  We have been texting since she got back home and realize we can't get together for two weeks.

The question now is: what about Aussie?  Well, we were supposed to see each yesterday after a three-week delay, and I was too busy to see her, which pushes her into next week.  That will be nearly a month since our last date, which is total crap.  

Do I find Phoebe more attractive?  In a way, yes, but again looks aren't everything.  She has her own place, a similar distance away from my office.  

I'd actually be fine with either one of them.  Not sure what I'm going to do.

Monday, May 2, 2016

Two Sugar Meetings in One Day (UPDATE BELOW)

This will be the third time in about four months that I've had two sugar meetings in one day.  The first was Red and Kona, the second Sports and Gemini, and now I'll be meeting today with Phoebe and a new girl (in about 10 minutes).  I don't have a name for her yet, but I will before long.

More to come...


Phoebe had to back out due to a work conflict.  We rescheduled for later this week.

I did, however, get to meet the new girl, whom I'll call Meredith. In her very early 20s, she's a recent graduate of my alma mater, with a degree similar to mine and one that came with a minor in entrepreneurship that makes her quite impressive.  She had last week texted me her first name, which was very unique, so I Googled her first name and our school name, and I found her LinkedIn and Facebook profiles.  Aside from being very slim and pretty, Meredith also worked at some of the campus jobs as I did, so I was thinking that we had a couple of interesting connections beyond the typical SB/SD partnership.  Boy, did I underestimate her!

She texted me at midnight last night to confirm that we were still on for breakfast at 8 am this morning, despite the fact that I'd already told her on Saturday afternoon that I'd see her then.  When I texted her at 7:45 am to let her know I was still expecting to see her, she responded with an apology that I hadn't confirmed her request (at fucking midnight?).  Actually I'd see it at 5 am, but thought it too early to answer her.  Then the morning caught up with me and I was involved in family stuff until I left at 7:15 to take my kid to school across town.  By the time I'd dropped him off it was nearly 7:40 and I had to stop at the ATM for a little cash.  With that in hand, I sent my text.  Turns out she'd gone back to sleep and would be unavailable for an 8 am meet, but asked if we could meet at 9.  I had an important conference call at 10, so I said yes, but it'll have to be quick.

She messaged me ten minutes out that she would be 10 minutes late.  I left my building to walk up the street to the little neighborhood breakfast cafe where we'd meet.  While on opposite corners across the street from each other, I spotted her.  She'd gotten ready in a hurry.  She.  Looked. Unbelievable.

Dressed in a slinky gray dress that hugged her very delicious figure, she looked just slightly overdressed for our meeting.  If that's what she wore to work, wow!

We hugged and smiled and I walked her inside the cafe where we ordered a nice little breakfast.

Not only did she and I attend the same school, we both followed the same academic path, from sciences to liberal arts.  AND we worked at the school paper!  AND we both spent time in college pursuing a passion for music!  AND she was originally from the same east coast state as I was!  So we had a great deal of little connections.  In addition to being seriously gorgeous, Meredith also had the bubbly and lively personality I so enjoy in my partners. From CC to C/Hayden, from Jade to Audrey to Aussie, the ones I find most attractive are the ones who have a positive outlook (my optimism at work here!).  Finally, she was one intelligent girl.  She had, in the past year, developed no less than five mobile apps, but hadn't sold any of them as of yet.  She was busy crashing networking events and unabashedly reaching out to CEOs of tech companies to get to know them. One of those CEOs turned out to be billionaire businessman and Dallas Mavericks owner Mark Cuban, whom she now counts as a friend.  She was offered a CEO position at a tech startup, but on Cuban's advice, opted for a path working for someone else in a lower job so that she could learn from the ground up.

At that point, I realized that we hadn't talked about allowances and that she would reject my offer once I made it, just like Ari a few days earlier.  Girls with friends like Mark Cuban don't hang with Practical Sugar Daddies, and I was at peace with that.

After breakfast I walked her to her car and we hugged.  I told her I'd be in touch and that I really enjoyed meeting her.  I felt a twinge of anxiety at that moment, feeling discomfort at the rejection I knew was surely coming.  But I easily moved through it, knowing that Aussie was still in my corner and Phoebe had also already accepted my offer.  If Meredith was a no, I would still be in great shape.

If or when I get her response to the offer I texted her half an hour ago, I'll blog about it.  Meanwhile, it's back to work!