Monday, February 29, 2016

WCSD Journal Sugar Update: Leap Year Edition

"Where were you on this day last year?" someone wrote on my Facebook feed. "Trick question," I replied, "this day didn't exist last year."

My friend's 80-year-old mother celebrated her 20th birthday today.

This morning, I woke up into those 24 hours I'd lost over the past four years.

OK, enough Leap Day silliness.  Time to update the masses of readers hanging on my every word.

The weekend went by, as did half of today, without any word from her as to whether she is available this week for an evening date.  Perhaps she wasn't really wishing I could be available at those times. Then again -- grad school.  Time is almost never free enough for any kind of dating.  I'm pretty sure she's getting ready for exams.  She's got spring break in about a month, so she'll be more available.

Lunch scheduled with her for tomorrow.  This take-it-slow SB has my attention for now, although I'm not sure I'll let her keep it much longer.  Let's see what tomorrow brings.

Didn't communicate with her much since our lunch last Friday.  Probably need to reach out to her today and let her know I'm still alive and kicking.  Perhaps I'll try to set up a date with her this week.

Second sex date scheduled for this week. Not sure yet I'll keep it, if perhaps I can make time with Aussie instead.  Although I do like KC and want to give her a second date.

Here's a screenshot of a text exchange we had that lasted two days last week that perfectly illustrates why I'm so reluctant to select her:

I hope this puts to rest any hope any of you had that I'd wind up with Sam.

Still on ice.  Not reaching out at the moment.  At some point she'll probably just give up on me, which would be fine.

Friday, February 26, 2016

Lunch With Aussie

This afternoon, Aussie took an Uber down from her neighborhood to where I was working.  She arrived on time, which impressed me.  We exchanged a brief hug and peck on the cheek and I walked her across the street to the restaurant where I'd also treated KC and Vee.

Aussie was a very cute girl, had a great figure, and wore attractive clothes.  I did my best not to look too much, but I noticed that the back of her top was all lace and I could see her back, which featured a long tattoo down her spine.  Oh well, I thought, another tat to add to the massive one on her right hip.

Despite being from Australia and having been the US only two weeks, Aussie had literally no accent when she spoke.  She explained that, as an actress, she adapts very easily to where she is in every given moment, has studied American and UK dialects, and can ditch her natural Australian twang without even thinking about it.  So, for our whole time together she sounded like a typical American girl.  I sort of hoped she'd slip out of it and I could get an earful of her natural voice, but that didn't happen.  In hindsight, I suppose I could have asked.

We had already handled the money particulars, so it was easy just to talk about our lives.  I enjoyed hearing her stories about her working in the US and UK, which eventually led her to move to the US because she was getting more work.  She said she moved into a large apartment with three roommates who were never there.  I logged that detail into my memory banks for later use if we decided to consummate.  I was certainly attracted to her.  She added that her acting resume was already large enough to get her work in the US almost right away, and that she'd give herself three months to make something happen before taking on a throw-away job.  She had a three-year visa so she was able to work and not have to travel back to Australia every three months for immigration purposes.  More good information to know.

We shared some horror stories about the sugar life, and then we got into a pretty serious discussion about our views on the lifestyle.  She agreed with me that these are truly real relationships, but she was happiest about being able to say "cut" when it was over and not have there be drama.  "Yes... and no," I said, which got a laugh.  "I've had my share of light-hearted and inconsequential arrangements, and some of them have been fun and ended without much drama.  But lately I've been thinking that, for me, the meaningful ones are more fun. The drama helps me learn more about myself, the sex gets hotter when there's an emotional connection that comes from what we share, we don't shy away from being vulnerable --"

"Oh yeah, I completely agree," she interrupted.  "When we're together, it's no different than a real relationship.  We're into each other, laughing, getting intimate, sharing feelings and stuff.  It's just that we know it's not going to go anywhere.  I mean, what's the point of the sugar stuff if there's an agenda to turn it into something else?"

I liked where she was going. "I'm not looking for something else," I assured her. "I just think that these things have a beginning and an end, but in between there's opportunity to have something truly real and rewarding, and to come away from it as a better person."  I took a minute to share my C/Hayden experience, and my Red experience ("you're lucky that didn't go farther," she said -- so right!).  I get the feeling that her experiences were far more light-hearted than mine, but I didn't get for a second that she'd shy away from something more substantial.  "Also," I added, "I'm the type of man who, when the 'date' ends, I'm still in contact and staying in touch."  Since she and I had already exchanged quite a few texts over the past several days, I didn't think she'd be opposed to some regular checking in.

I paid the check and we took a brief walk around the block, doing some window shopping.  She said that with her first big acting paycheck she'd buy plane tickets for her family to come visit her, "then I'll come here and buy all this fabulous stuff!"

She ordered another Uber once we got back to my building.  I though of giving her money for the car, but I only had Benjamins in my pocket at the moment.  I resolved that, if I saw her again (and I wanted to), I'd pay for her car service.

While we stood waiting for the car, she caught me looking at her body.  "Are you checking me out?" she asked.  "Yes, without shame," I replied, and she gave me a quick turn so I could take it all in.  "If we weren't out in the street, you'd see how much I appreciate that," I said.

Her car arrived and I walked her across the street to the car.  We exchanged a quick kiss on the lips and she was off.

I'm thinking right now that I'd like to see her again.  Should Leah not work out, I'd pick her over KC anytime.

WCSD Journal Sugar Update 2/26/2016

Well, we I missed each other this week.  I was not expecting it to happen, but at least this time it was for a legitimate reason.

Leah's in grad school.  I have friends and relatives who are either in or have recently finished grad school, so I know the drill.  The drill is, if you want to be successful, everything aside from food, sleep, and studies must take a back seat.  Leah confirmed with me Wednesday afternoon that she was ready to meet me, but then asked if we could meet earlier than 3:30 pm, as in 12 noon.  "'Cause now I have a meeting I cannot miss at 4."

"If you had a meeting that you couldn't change why did you just confirm?"

"I confirmed assuming you could do earlier."

I shook my head.  Two days ago I had just told her that I was rearranging my work schedule to be in her neighborhood at 3:30 on Thursday.  I said I couldn't change on a dime.  Besides, I added, hotel check-in times are around 3 or 3:30, so earlier doesn't work unless she has a place to meet.

We agreed to talk Thursday to see if we could make plans for Friday, which I was hoping to make happen.  She said she would check, but added, "I wish you were available evenings!"

Now, this triggered me somewhat, in that I had a few weeks earlier told Natalie that I couldn't see her because she could only meet after work.  I replied, "I might be able to do evenings once a month, but I wouldn't want to meet evenings every time."

She didn't answer for about ten minutes, which made me wonder if she was annoyed.  "Is this a simple scheduling conflict?" I asked, "Or, is this an example of what you have called 'self sabotage?' I mean absolutely no disrespect, but you can understand my sensitivity given the numbers of cancellations we had before."

"No, no," she replied, "it's truly scheduling.  It's hard because sometimes appointments pop up that I can't predict or cancel."

However, that evening, DW asked for my help picking up one of the kids early from school, so now I was unavailable.  I let Leah know that we should try the next week.  She replied an apology and said OK to next week.  "And worse case scenario I have spring break coming up soon so I'll be available around your schedule."

"I have a full time job and a family who needs me," I wrote, "but you're important to me and I'm willing and able to stretch to see you.  Pick a Wednesday evening and I'll schedule a 'work dinner.'"

That evening DW told me she'd managed to solve the school pick up problem and didn't need me after all.  I texted Leah right away.  "I. Am. Free. Tomorrow!"

"Aww, I just started feeling sick a few hours ago."

"Of course.  Story of my frickin' life."


I reached out yesterday afternoon: "Hope you're having a good week. Sorry I've been busy and it's been hard to get current.  Feel free to touch bases if I'm ever too scarce."

She wrote back about 40 minutes later: "I've been keeping pretty busy.  Any chance you'll be available next Wednesday?" We have a scheduled date.

"It's possible!"

"I like the sound of that.  I can't wait to get my hands on your dick again."

"I know we have an arrangement," I wrote, "and I would fully honor it, but you're not prohibited from inviting me over more often."

"Come over tomorrow then!"

As I was still holding out for Leah's availability I didn't want to commit, so I told her I was busy. "Maybe today?" I suggested, as I'd had another hour left in my work day and could probably fit in an hour or so on my way home.

"I'm out till about 7ish."

"Just keep it in mind," I said.  "You and I every other week, per the arrangement, and off weeks up to you."

She agreed!  "I guess I'll just check in with you whenever I'm horny to see if you're available."

I am learning something about myself via KC, which I'll share later.


We spoke on the phone for about half an hour yesterday as we both drove home from work.  "I prefer this to texting," she said, and I agreed.  We made a date for lunch next week, another casual, no allowance, get to know you lunch.  I suggested we do something different: We'll pick something up to go and then walk around the area, rather than sitting in a restaurant.  She loved that idea.


Meeting her in 10 minutes for lunch.  Will fill you in later.

Tuesday, February 23, 2016

WCSD Journal Sugar Update 2/23/2016

Another potential has entered the picture, and she is a strong contender for backup in case things don't work out with Leah.

"Aussie" is -- what else? -- an Australian girl in her late 20s, an actress who has been in the US all of a week.  She has no car, but she has money enough for an Uber anywhere she wants or needs to go, and has agreed to my financial terms.  (I'm telling you, the lesson I learned after the Red disaster, about making sure everything is handled before we meet, is really paying off.)  We're meeting Friday afternoon for lunch near my office.

Aussie is very cute, with short reddish hair (probably changes color a lot), blue eyes, and a cute pixie-ish face and smile.  She's about 5'6", slim, and petite.  Great body, although she has one massive (but beautiful) tat along one hip.  We haven't spoken by voice yet, and I'm pretty sure I want to before we meet, but I won't require it if there's no time.

Leah and I chatted last night about a few things, most notably her studies. She had a guest speaker in one of her classes who brought up the topic of sexual attraction between a therapist and his/her client and ethics and boundaries. She said that she'd be in big trouble if I were one of her clients. She also thinks her current therapist is attracted to her.  Then I decided to revisit our sexual past, and asked, "Are you able to achieve orgasm through sex, or are you still hooked on your vibrator?"  She replied, "Definitely vibratory at this point, unfortunately. I haven't had much time for sex except that brief relationship I told you about, and even that was infrequent."

"Bring the vibrator Thursday," I wrote, "no sense in you not getting yours. I mean it."

"Well," she replied, "I might feel pressured.  It will come, naturally, over time I'm sure."

"No pressure, babe, not at all. Think of my request as an act of kindness.  Or something...looking out for your needs.  Just thinking of you.  Hopefully our get-togethers won't be infrequent."

She asked if we could get together more often than twice a month.  I wasn't going to go there by text. Perhaps after we are together (IF???) I can bring it up again. But she said she probably didn't have time for more than twice a month anyway and that the allowance was fine as before.

She then confirmed that her Thursday afternoon was free and she'd be there.  "I'm still gonna confirm Wednesday afternoon and Thursday morning," I wrote. "I'm obsessive."

For me, it is now Leah, then Aussie, then KC.  KC drops down because Aussie is more my type. We'll see what happens Thursday, however.  If Leah and I do manage to get together, I will still meet with Aussie.  I told her yesterday that I was down to basically two choices and she was one of them, so if I go with the other she won't be too let down.  She's likely talking to other men anyway.  KC and I have a scheduled date for next Friday, but if Leah and I start up again, I'm going to cancel the date and say goodbye in a nice way.

Other updates:
Sam: still there, we seem to be drifting into a bit of a friendship zone, although I adore her and really enjoy her company.  There is no pressure to resume anything, since it's clear that her travelling makes it difficult.
Sarah: I put her on ice two weeks ago, and stayed in contact for another week, but nothing since.  I don't think I'll reach out again, although I probably should.  She's been sweet and she deserves the truth.
Vee: I'm definitely less interested in her now that Leah might be back, and after Thursday will let her know. I think she might be a little too reserved for me.

Monday, February 22, 2016

Slept On It -- No Change

My desire for a reunion with Leah has not diminished with the new day.  I woke up excited to be seeing her again.  However, I reminded myself of my behavior in the days that followed her original consent last fall to seeing me again.  I got too enthusiastic and felt too nervous to keep my cool.  I'd acted like a 16 year old kid who'd never had a girlfriend before!  With all that has followed since -- Natalie, Red, and now KC -- I have learned some serious lessons about the benefits of communication.  (I have a dear friend who calls texting a "miscreant technology."  I see the humor in that characterization, as texting has come to replace proper, "lawful" communication like phone calls and face to face conversations. He originally refused to use it, but we now regularly chat with each other, albeit briefly until we can talk directly with each other.)  I believe that I'm 100% right about the limitations of typed words and emojis to convey context, feelings, and real truth.  It's why I so often push potential SBs into coffee or lunch dates to discuss the financial perks I offer.  There's simply no better way to gauge a person's level of interest in -- or, for that matter, worthiness of -- the allowance I want to offer.  This is particularly true if the potential SB in question is someone I'd really like to meet.  I have, on occasion used both the messaging function on the Sugar Daddy website, or text messages, to communicate the logistics, but I generally try to avoid it.

Anyway, I will use great care to communicate with Leah this week economically and without a need for a response.  The only time I want a response is when I text her to confirm the day before and the morning of our date.  And when I do that I'll clearly state that I'm looking for a response.  That doesn't always work, I've found, but it's better than being ambiguous about wanting a response.  A generic "let me know" isn't as good as a specific "I need you to confirm with me before I book the hotel room (sorry for being so formal)."

It bears pointing out: I am treading very carefully here. I adore Leah, would love to be with her, and have hidden my Sugar Daddy profile (at least temporarily) until this all plays out.  However, I have no expectations of where this might lead.  She has recently been very flaky, and we have both exchanged some unpleasant words, but there's no denying the mutual attraction.  As I did with Red, I will have a backup plan, and right now her name is KC.

Sunday, February 21, 2016

How Do I Not Look Like a Fool Now?

Last Thursday night, while beginning my evening dog walk, I sent a text to...


Yes. Nearly two years to the day when I ended my relationship with her, more than a year and a half after our last physical encounter, nearly two months after she canceled our third date in a row, saying she no longer wanted a sugar relationship, and even after I permanently banned her from my life, I reached out to her.  "Hello there," I said. "I am over my regret." She thought I was being funny, but I was deadly serious.  "How is this funny to you?" "It was just out of the blue," she replied.  "I understand," I wrote, "but it did take a while to get to this point, and a lot of work.

I got to the point: "Why do you think it is that I can't seem to shake you loose? We were only together for a few weeks."

"I don't know," she said. "I'm open to hearing your thoughts."

"I see that you're honing your therapist's skills," I wrote. "By the way, I wish I knew the answer to that question.  It seems so illogical."

The first part of that text got another laugh. "You're a pistol tonight! Honing my therapist skills."

"'I'm open to hearing your thoughts,'" I repeated back to her.  "MFT 101.  I'd be open to sharing them, btw."

"I would be happy to listen."

At this point, I felt serious skepticism, but not enough to abandon the conversation.

"That would require ears," I wrote, the implication being absolutely clear -- at least I thought so.


"I've abandoned texting for any sort of revealing information," I wrote, the fruitlessness of my revealing texts to Red still fresh in my mind. "Punctuation and emojis are no substitute for eye contact and voice inflection and body language."

"I agree," she replied, adding, "Well I guess we should arrange something."

I suggested a meeting for the next day, but she wasn't available on short notice. I then asked her for times that worked best for her.  I noticed the hour and thought she'd be sleeping. "I realize you might be sleeping my now, but that was a legit question, and I hope you can answer when you're able." Again, my sensitivity about Red's ghosting me, and Leah's previous cancellations, was throbbing in my stomach. "Please -- and I'm practically begging here -- just do not ignore it.  I have zero intention beyond talking.  You have a boyfriend."

She wrote back right away: "I don't have a bf.  Why do you say that?  Do you want to talk on the phone?  I can call you tomorrow."

"You told me in December, on the day we were supposed to meet, that you had started dating someone." It must not have worked out, or she was just casually dating the guy.  "I prefer to meet in person, but if that's impossible for whatever reason, a phone call is fine."  I was tired now and wanted to go to sleep. "Please let's continue the conversation."

She actually responded the next day to my request to confirm our phone call, but she was tied up and suggested a conversation over the weekend. At this point, I'd come far enough that I wanted to talk to her again, and I suggested Sunday (today) at noon.  She agreed.  "Not gonna change your mind again, are ya?" I asked, half joking.  "LOL no," she wrote, "I also have thoughts to share."

I made arrangements with DW to be alone at noon.  At 11:30 I texted to let her know I'd be calling her, and she pushed it back five minutes.

When I called she picked right up.  She was headed for lunch and was just getting into the car.  I knew my time was limited, so I got right to the point.

"Leah, I don't really have an agenda here. I just wanted to share with you why I am struggling so much with, sort of, walking away from you.  It makes no sense why I should want to maintain contact.  But I do.  Somehow, for whatever reason, at some point during the time we were together, you crawled under my skin and you just haven't left.  I don't know what it means, really, but I thought perhaps you had some insight."

"Well," she said, "I regretted cancelling on you that last time. I really did want to see you."

"So why did you tell me about the guy you were dating?  You're not dating him anymore?"

"No that lasted just a little while.  I don't know what I thought I wanted from him. I wanted to see you, but really I felt concerned because you'd told me you were talking to other women."  She explained that she wanted to be with me, but not if I was going to see other girls.  She said it made her feel unsafe.

I didn't know what to make of this, but I stayed with my feelings rather than trying to appeal to her logically.  "Leah, I talked to other girls because I felt unsure that you were serious about getting back together. And in a way I was right to do that, given what happened, but the truth is, none of them really mattered. Why do you think I keep reaching out to you, giving you chance after chance after chance? I wanted to think I had some logical reason for it, because I'm always the logical guy. But it's because of how I feel about you.  I adored you, Leah.  I still adore you. I talked to other girls, and I saw one or two, but I've had no attachment to any of them, not like this."  I was telling the truth. Other than Red I never felt anything remotely like what I felt and feel for Leah.  Not for Audrey, or Staci, or any other.  "If it makes you feel unsafe, Leah, I can do something about that.  If I de-activated my profile so that no one could see it, would that help?"

"Yes. That's sweet of you," Leah said. "Well, I do want to see you again, Porter."

I was floored. "You do? After all that I've said -- and I apologize for that, sincerely -- you still want to see me?"

"You're not the only one who has feelings."

I have no memory of what I said after this.  It was all a blur.  I just remember making plans to get together this week, which is going to entail me having to rearrange my schedule for the week to be in her area.

After hanging up, I went back to the sugar daddy website and I hid my profile.  I decided not to de-activate it entirely until we actually saw each other.  Taking a screenshot, I texted it to Leah and told her that after we got together I'd cancel my subscription altogether, but asked for her understanding that, based on all the previous cancellations and mind-changing, I wasn't completely ready to commit to a 100% shutdown. She understood and thanked me for my honesty.

So we'll see what happens this week.  I have no plans with KC till the week after, so I feel like it's no skin off my nose if she cancels.  As I learned with Red, I am going to continue keeping my eyes wide open and not let myself get totally sucked into anything.

Readers, you will, again, think me totally foolish for even thinking about Leah again.  I am probably foolish.  But with this paradigm shift of looking for something much more real than all the superficial nonsense that has passed for sugar relationships since C/Hayden and I broke up more than three years ago, I would rather go for it and be totally wrong than play it safe and miss out on an amazing opportunity.

I hope to write something more for you later this week after we meet.

Thursday, February 18, 2016

KC Offers Up a Mixed Bag

I'd met KC a little over a week ago over lunch near my office.  I'd found her charming and fun, although I wasn't quite sure I was fully attracted to her physically.  She was taller and appeared much heavier than the girls to whom I'd normally gravitated.

She was undoubtedly sexual, and confidently so, and I found that inviting.  Further, since our lunch, she had reached out repeatedly to say she was looking forward to seeing me again, presumably for sex.  She had her own apartment that was very close to my commute route, which offered up serious convenience. As you've all read before, I like my sugar activities to have as little impact on my work and family life as possible.  Truly a short diversion in the middle of my day.

With the paradigm shift of looking for a long-term mistress playing a role in my decision-making process, however, it isn't all about convenience, but about finding the right combination of the right elements.  KC was attractive enough, sexy enough, intelligent enough, independent enough, mature enough, had her own place in a convenient location, and had accepted the terms of the arrangement. She was a very good candidate.  A big test would be our sexual compatibility.  And, with my new mind-set, I was not going to make this decision after only one time together.  The nervousness/ awkwardness factor had to be considered in weighing whether we were good together in bed.  Had it been my criteria back in 2009 that it had to be awesome from the first minute, C/Hayden and I never would have made it past our first (or even our second) time together.

KC and I had set a date time of 4 pm, which gave us a good couple of hours together.  Even though it rained during the entire drive up from my office, I made it there with about five minutes to spare.  I'd playfully asked her that morning to leave the door unlocked, and for her to be naked and masturbating when I arrived.  The door was unlocked, but she was fully clothed and sitting at her desk, working and drinking a large glass of red wine.  An episode of "It's Always Sunny in Philadelphia" (her favorite show) was streaming from Netflix on the living room TV.  Netflix and chill, I thought.  She was an enthusiastic wine drinker, to be sure, as she sipped on a couple of glasses during our time together and offered me a glass more than once.

I took off my jacket, and lay the money envelope on a small table near her front door.  She finished working and joined me on the living room couch, wearing a white print tank top over a red bra and black Lululemon yoga pants.  She was definitely chunkier than I was used to.  Her body reminded me of Dale, who was curvier and more toned, but similar.  Dale would today be about KC's age, I thought.

We talked about the decor in her place, some previous experiences with Sugar Daddies, her "shitty fuckin' neighbors" -- pretty much anything that came to her mind.  Girlfriend could fucking talk and talk and talk. On and on and on.  And she had that very annoying habit of raising the pitch to her voice at the end of every sentence, as though everything were a question.  "So I walked into the bar? And it was, like, packed with people I didn't know? And I couldn't even find a seat? In like, my favorite and most regular hangout?" You will undoubtedly get my meaning, right?  There were moments when I just looked up at the light fixture in her ceiling, pretending to be thinking about something other than, "Does she ever just shut the fuck up?"  I even asked her to give me the tour of her place, thinking that by the time we reached her bedroom she'd get a clue and realize that half an hour had gone by and perhaps it might be time to kiss me at least.  But no.  Back out to the living room, sitting on the couch, Danny DeVito and cast acting like lunatics about something meaningless, and her sipping more wine.   I searched the coffee table for the TV remote, wondering if the Mute button would work on her.

Finally, I couldn't take it anymore.  Her body was pretty sexy despite her size, and her low cut top revealed enough of her tits for me to want to take off her clothes.  So, I just leaned in and said, "I'm gonna kiss you now."  "Oh, OK," she said (as though this hadn't even occurred to her).

Kissing KC got off to a rocky start.  It seemed that two days earlier she'd had to remove the nose ring she was wearing (which she didn't wear when we met for lunch) because the area around it had gotten infected, and now that spot was sensitive.  I had to be careful with my nose not to bop her too hard (this isn't easy, as my nose isn't small).  But once we got the hang of it, things started to get better.  I detected the slightest tobacco taste on her breath, but it was so small -- much smaller than Jade, or Chica, or even the SB who didn't even warrant a name -- that I did not object, particularly when I tasted the wine on her breath as well.

Reaching behind her to grab her butt, I noticed that her butt cheeks were BIG and round, much bigger than my hands.  I've written before that I'm not much of a fan of big butts.  Even a girl with a sizable booty like Audrey was small enough for me to get a good grip on.  And KC's was pretty soft too.  I worried about what she'd look like naked, even with my tongue in her mouth. But I'd seen pictures of her naked and I remembered that her ass was actually quite hot.  So I just went with it.

KC's hips started rocking hard the minute we started kissing. Definitely turned on, the way College was when we were together, and I found that exciting.  The couch, however, was proving to be quite uncomfortable.  She'd offered to switch positions on the couch, but I just said, "Why don't we change rooms?"  "Oh, OK," she said (as though this hadn't even occurred to her).  I grabbed the lube and condoms out of my briefcase and followed her in.

She started peeling off her clothes, and was out of her pants before I told her to leave the rest on.  We pulled down the covers of the bed and climbed in, me fully dressed, wedding ring on, watch on, wallet in my back pocket (what in the actual fuck?).  The only thing I'd undone were the buttons on the cuffs of my shirt!  Within in few minutes, however, all seemed right with the world, and we were both naked.

She had small breasts for someone her size, a broad back, wide hips, and thick thighs, but she pulled all of it off very, very well.  I liked kissing her a lot, she smelled good, and her skin was nice, so I enjoyed myself a lot.  I got her out of her panties and started rubbing her between her legs. which got her moaning a lot.  A lot.  I went down on her, and she rubbed her pussy all over my face, asked me to finger her ("with two fingers, please?"), and she had a seriously hot orgasm.

When it came time for her to play with me, she took my dick in her hand and said, "Seriously, I hate it when guys send me dick pics, but if you'd sent me a picture of this, I would have touched myself just looking at it."  I laughed.  She was pretty fucking cool. Her BJ skills were adequate, not fantastic, but good, and I let her go down on me for a couple of minutes before I reached for the condoms and lube.  However, she just reached for me and pulled me on top of her.  I got between her legs and she was so wet, I just slipped right in.  When I felt the contraceptive ring, she said, "I need to take that out."  While she did that I put on the condom.

KC was the most vocal lover I'd had, ever.  So much talking -- "Ohhhh FUUUUCK, you feel so FUCKING GOOD, FUCK me!  Fuck me HARDER, baby!"  -- and so much moaning, I thought she was perhaps putting on a show for me.  But the girl was seriously soaking wet -- the sheets proved it -- so I knew she was just in the zone.  Her hips didn't lie either.  I especially like how bendy she was. I got her legs practically behind her head and just pounded her, and she kept up like a champ.  "Don't you fucking stop, don't you fucking STOP," she said, and when she came again, I stopped while she twitched and laughed and said, "Oh, yeah, that was so FUCKING GOOOOOD! Turn me over and fuck me doggy-style, k?" How could I say no?

I spanked her big booty so hard it turned red. Girl liked it rough, and I think that because of her body type, I noticed that the rough sex wasn't as punishing on me as it had been with The Dancer.  I asked her to get on top of me, but she said she had a bad knee and that position was uncomfortable for her, so I flipped her over and entered her again.  There was zero need for lube with this girl, and within a couple more minutes I felt ready.  I pulled out, took off the condom, and unloaded all over her belly and chest.  I was still super hard, so I slipped my uncovered cock back inside her, but just for a second, because I was way too sensitive.

We talked for about half an hour about past experiences, and then fucked one more time before I left, harder than the first time, and with all the same amount of moaning.  We came at the same time. "You can fuck me without the condom, next time," she said.  "I got tested just a month ago and I haven't had sex for two months."  That explained her enthusiasm, I thought. "Maybe," I said, "after we get to know and trust each other more."

There will be a next time with KC.  I like her pretty much all around.  Can't say she is the hottest woman I've ever been with -- C/Hayden literally sucked the breath out of me every time -- but I definitely enjoyed having sex with her.  Maybe it was nervousness that made her talk non-stop, or maybe she just had a lot to say and didn't want just to jump into bed with me.  Maybe next time she'll actually be naked and masturbating when I show up. With a ball-gag in her mouth.

The Long(er) Road to the Paradigm Shift

I was chatting this morning with an SB friend and I admitted that I'd lucked out with Red appearing so soon in my search, but that I was probably not ready for her. The process of finding the right woman to be my mistress was going to take longer than I thought.  I wrote last month that I was going to "fake it till I make it."  Apparently it's possible for fakers not to make it right away!  Who knew?

Anyway, I wrote last about my lunch with Vee. While we had a nice time, and while I'd be interested to take the next step in getting to know her, we had a bit of a rocky text chat the other day:
Me: Hope you're feeling better today.
Vee: Thanks. Still pretty congested.  Woke up at 3 am and couldn't get back to sleep.
Me: I know that feeling.  But I'm usually able to get back to sleep (orgasm)
Vee: I tried.  Twice.  Didn't work.  But I made myself a real breakfast this morning. That never happens.
Me: You came twice and no rest?
Vee: Nope
Me: Too bad I wasn't there.  I've been known to put many a woman to sleep after [giving them an orgasm]
She took offense to the last comment, saying she did not care to get sexual with someone she didn't know, and that she didn't think she was the girl for me. I wasn't the least bit shocked by this statement, because (and I admitted this) I was a bit of a troublemaker and liked to push boundaries, but would respect them now that I was aware of them.  She didn't respond at first, and I thought I'd had another silent treatment on my hands. "I guess that doesn't matter?" I asked. "You're out?"

She wrote back and said that she assumed I'd be out after she revealed that she was uncomfortable.  I decided to be a little assertive while also establishing my own boundaries. "Well, I'm not some pervy old guy who can't keep things respectful and decent while we get to know each other.  You're a nice girl, after all."  She calmed down after that and said she was still interested, and I returned the sentiment.

Vee's very cute, has a wholesomeness about her, is kind, but is perhaps a tiny bit thin-skinned and a little sexually reserved(?) - is she even good Sugar Baby material for me? As I navigate this road of Sugar Baby vs. Mistress, I'm not sure yet if even I'm good Sugar Daddy material for anyone!  But I am definitely committed to finding out!

My next post will be about my sex date with KC.

Tuesday, February 16, 2016

Lunch With Vee

I am so glad that I got to meet Vee today.  She showed up early to make time for parking -- major points there! -- and we saw each other in the building lobby at precisely the right time.  Off the elevator came a very cute brunette wearing a khaki green jacket over a black tank top, skinny blue jeans, and tan suede half-boots.  A perfectly casual get-up which I appreciated.  She had long, straight hair to the middle of her back, and her brown eyes, although indicating Asian heritage, were lighter brown than typical of most Asians.  She must be only half-Asian, I thought.

We went across the street to the same restaurant where I'd had lunch with KC a week earlier.  We got a table right away and ordered pretty quickly.  She ordered black coffee, which I found a little curious given the hot weather.  Vee had an appointment about 45 minutes away, so we'd only have about an hour to chat.

Vee told me before leaving to meet me that she had a sinus infection and was dealing with antibiotics and pain meds so she was a little concerned she'd be a little out of it.  But she was perfectly pleasant and friendly.  I liked her voice too: sort of a Demi Moore-type without being overly raspy.  She had beautiful white teeth, a pretty smile, and really warm eyes.

During the meal she told me her real name, and confirmed that she was half-Asian.  I absolutely loved the ethnic combination; it had real appeal to me on multiple levels.  We talked about a lot of things, including making sure that all the logistical stuff was out of the way. We agreed on money, how often to get together, and where we'd meet for intimacy (her apartment, which she said was "immaculate").  In particular, however, we discussed what she wanted to get out of an arrangement with me.  Having had an eight-month relationship a couple of years ago, she knew that longer-term deals worked better, and she was hoping to make a connection and get help with money, business advice, and have someone intelligent to talk to.  She also revealed an intimate detail about herself which explained (at least for me) why she ordered the coffee.  I won't get into that detail out of respect for her, or for anyone reading this who has a similar experience.

Finally we briefly discussed sex, but I didn't push any specific agenda.  Stuff like that would happen in due time, and I don't know at this point if I we'll get that far.  She would like the arrangement to be more like real dating: going to movies, meals, comedy/music shows, etc.  I made sure she knew that evenings were difficult for me but that I was definitely open to getting together once in awhile on that level.  I found it refreshing that she saw the arrangement as more of a relationship, and the gradual building of a relationship that isn't 100% tied to sex/money appeals to me a lot.

After lunch I walked her back to her car and gave her a hug.  I wanted to kiss her but we had just discussed our mutual dislike for too much PDA.  Still, we were in a parking garage and behind a big concrete post.  I should've gone for it. Oh well.

My next post will be a reflection on the paradigm shift.

Post Red, Some Good Possibilities

In response to several texts and a phone message this morning asking for a response to my concerns, I finally got my answer.  "Porter, what the hell? I'm sleeping.  Why are you blowing up my phone?"

Was she fucking kidding me? I sent her a very serious text asking her to let me know if she's reconsidering and this was how the conversation began?

"I'm not blowing up your phone," I wrote, "I requested a response a couple of days ago and you've been out of contact."

"I think it's best we not move forward. Good luck with your search."

"Perfect," I responded. "I've already moved on, as you have."

A few minutes later, she texted that she hadn't moved on but was thinking about things and was disappointed that I had done so.  "Anyway," she added, "then you blew up my phone. You're too needy for me."  

That got me mad, and I let her have it. "I asked you to do one thing, to let me know where things stood.  Had you let me know you were thinking it over and needed some time, I would have been patient.  But your silence in response told me what I needed to know: that I was no longer desirable. I'm sorry for my part in how this blew up.  We missed a crucial conversation, and I've learned my lesson.  I definitely won't make that mistake with the next one.  Finally, there is a VAST difference between wanting someone and needing someone. I wanted you and I was very clear about that.  I told you I wanted only you, but you clearly didn't want me at a lower allowance."

What a total waste of my time.  This is the 14th (and last) post I've written about her. I'm so glad I kept my wits about me and didn't get in too deep with this girl.  I can't imagine what might have happened had she and I gone down the path, dealing with her obvious feelings that she was settling for less than what she wanted.

Time to start the process again.  Lucky for me there are five women to choose from.  Here's my agenda this week:

Vee: We are meeting today for lunch near my office. She's definitely a contender since she strikes me as genuine and I like the way she looks.  She has a very easy-going attitude, and that's attractive to me too.  She also lives alone, although slightly off the beaten path.  We agree to terms as well. As I've shifted my paradigm, I'm not going to press the sexual issue with her yet, but when the time comes for me to decide, that will be a primary topic of discussion.

KC: We are meeting tomorrow for sex at her apartment.  The attraction is pretty clear and both of us want the same thing.  I can't say she is the hottest girl I've ever met, but I like her no-nonsense attitude.  We'll see if it translates into a good physical connection.

Josie: We are meeting Friday for coffee near my office. I really like her looks, and the fact that she lives close to my office, but I've maintained for eight years that I don't have relationships with moms so this would be a first.  Her text personality is a bit flat so that is a bit of a concern, but I reserve judgment till we meet.

And here are the others:

Sarah: So far I've managed to keep her at a distance.  I don't like that she has a boyfriend, regardless of how far away he is.  Her attention is diverted nonetheless and I will always wonder when I become completely expendable.

Sam: Dependable, and totally sexy, but too unreliable for anything regular.  She's my fall-back girl when nothing else works out.

My last comment about Red: I am very disappointed, and my anger is not sitting well with me right now.  I was not pleasant with DW or the kids over the weekend, even with Valentine's Day and family gatherings taking up much of our time. Red and I both made mistakes.  I'm so glad I gave myself other options, and I wish her well.

Monday, February 15, 2016

And Just Like That...

Red apparently showed her true colors today, and as far as I'm concerned, it is off with her.

I can't blame her.  We missed a crucial detail in our discussion of the arrangement.  In her initial message to me -- in fact the first message she sent -- she asked for $500 per meet, eventually moving into a monthly allowance.  What she never mentioned was how much she wanted for her monthly allowance. I didn't bother asking what she wanted per month because I just said that the per-meet allowance worked for me.  We had an incredible connection, but unfortunately, she had one idea and I had another. When she told me she wanted to become my mistress, she was expecting five dates a month.  Not what I'm able to provide, either financially or time-wise.  She said she was OK with a the per-meet times two, but in the back of my mind, I sensed that she was crushed by this news.  She played her cards close to the vest, but it was apparent almost immediately to me that she was already reconsidering.

The first sign for me was the fact that I wrote her and let he know that I'd de-activated my profile on the sugar daddy website. "I can't expect you to do the same, but if you did I would appreciate it," I wrote. "Either way, I'm so grateful for the Valentine's Day gift you've just given me."

Hours later, she responded with some heart emojis.  Not a word acknowledging my comment. Further, a few hours after I sent that text, I looked at her profile, and the website noted that she had been online in the past twenty minutes.  The account was to remain active, apparently.  As I had clearly not pressed the issue with her, I knew that I could not complain.  But the timing of it certainly told me that not only was she reconsidering, she was actively looking for someone else, and would settle on me in case no one turned up.

The next morning, I sent a good morning text and a chiding remark. "I've concluded that you're not a fan of texting," I wrote, sticking a winking emoji on at the end.  Again, hours later, came back, "Not particularly."  That she still hadn't responded to my text from the day before, I knew that I was right about her. I did not want to be the one to be told, "Sorry, Porter, your offer was just not enough, so I've decided to keep looking."  I wanted to give her an out that would take the high road and give her the opportunity to end it directly.  So I wrote, "Red, I'm truly concerned that we've had this miscommunication about the terms of our arrangement. While I'd be sad, I would fully understand if you told me you were reconsidering a relationship with me. It's more important to me that you're happy and taken care of.  You are a spectacular woman, and I want to be clear that I believe we'd have a great time together no matter the amount of support I provided. If it helps you decide, I am willing to step things up to three times a month.  If this doesn't help, I would appreciate your letting me know now."

That was twelve hours ago, and there was no response. Again, I checked and noticed she was again recently online on the website. The message was clear: she had moved on. I'm glad I found out so soon before anything began, but I'm pretty disappointed that someone who professed so adamantly not to be a game player and to be direct in her communication chose instead to be non-communicative.

I guess the lesson I am to learn here is to keep a very safe distance from your intended SB.  You'll read in all of my previous posts about Red that while I was intensely attracted to her, I kept my eyes wide open to the possibility that I was not the right man for her.  I wasn't totally wrong, but our failure to launch was clearly a product of poor communication.  Fortunately, I have no less than five potentials to choose from at this point: Sam, Sarah, and KC, as well as two others I have not yet mentioned: Vee and Josie.  Vee is a late-20s Asian and Josie a mid-30s white woman.  They're both very attractive and work in businesses related to mine; both are also self-employed.  I prefer Vee to Josie since Josie has two children (similar ages to mine), but she insists she has a great child-care arrangement.  I would be concerned about her ability to keep to our date schedule since she's also a student.  I've got dates this week with both of them for coffee.  I'm also scheduled to have an intimate date with KC in a couple of days.  I'm pretty attracted to her and I appreciate that we have discussed and agreed upon terms.

Saturday, February 13, 2016

It's So On

This morning:
Me: Is it wrong to tell you that I miss you?
Red: No, it's not wrong. It's natural.  We have sexual chemistry.  I've thought about it and I'd like to formally enter a relationship with you as your mistress.  I think seeing each other five times a month would be good.  We can go to lunch/dinners and private play.  I prefer to keep the PDA to classy.  I'm very private with that. My roommate doesn't have a set schedule, so meeting here is difficult.  I am more than happy to put a hotel on my card, provided you reimburse me, so it's not showing on your card history. You're the only one I'm seeing and I ask the same. I'm very direct and I don't play games.  I ask the same.  If I'm not making you happy, tell me what I can do to be better for you.  And vice versa.  We must use protection.
Me: Wow!  That's just awesome, thank you.  I want to see you too.  And agree that we have chemistry.  But five times a month is just more than I've got time for.  I'm really only available twice a month.  How do we resolve that?
Red: Is it an allowance thing?  Did we discuss what I'm seeking?
Me: It's both, actually. You mentioned a per-meet in your initial messages, but not a monthly amount. This feels really awkward.
Red: Don't feel awkward.  I don't.  You prefer the per-meet twice a month?
Me: Only if that works for you.
Red: That works, no problem.
Me: With more, potentially, if circumstances permit it.  Whew.
Red: I understand.
It is on with Red.  She is my mistress.  Over time, I hope we become lovers in the true sense of the word.

The formality of the exchange, as opposed to some playfulness, is not lost on me.  I take it on myself to inject fun and humor into the relationship, and let her follow if she wants.  I'm also not unaware that her financial expectations, being more than double my offer, should have been discussed up front, and that she might therefore continue to look for a more lucrative relationship.  I hope not, and I will more than likely do what I can to invest more as I'm able and as my schedule permits.

We are seeing each other for lunch again next week, and if she's up for sex, again the following week.

For now, I am over the moon.

Friday, February 12, 2016

Lunch With Red

I could hardly concentrate on work this morning, knowing that I'd be heading across town in a few hours to meet Red for lunch.  Three weeks after our not-so-great first meeting, the journey to this lunch date took a few days to settle in, and then I had to contend with moments of self-doubt and anxiety over exactly how I could win this gorgeous redhead over.  After confirming with her that she felt physically up to meeting, I knew I would get another chance.

Fortunately, my boss showed up shortly after I did, so I felt compelled to show that I was being productive.  Making calls, asking him questions, talking over deals we were putting together, I had no trouble telling him that I was leaving early to work from home in order to meet some workers taking care of things.

A fortunate coincidence: the building management hosted a pre-Valentine's Day gathering in the pricey restaurant located in our lobby, and they had Sprinkles Cupcakes provide some beautiful desserts, for free. I saw an opportunity to grab one for Red, some for my family, and score points with all of them.  Red got a gluten-free red velvet one, while DW and the kids were treated to chocolate insanity.

At the appointed time, I gather up my stuff and headed down to the car.  I gave myself an hour to make it, which became fifty minutes when I realized a minute out that I'd left my sunglasses on my desk.  I could not be without shades on a sunny day like today, particularly when I planned to have lunch outside with Red.  Got my boss to run them down to me as I waited parked in front, then I hit the road.

I arrived about 15 minutes early, which was perfect.  Headed up to the restaurant to get a table, as I hadn't made a reservation and this place tended to fill up quickly.  The hostess seated me immediately so that I didn't have to settle for an inside table.

With about two minutes remaining, Red texted me to let me know she was walking and was five minutes away.  I sat facing the street so I could see when she was arriving.  On the table was the box with her cupcake, and in my briefcase two envelopes.  One was a Get Well card containing the cash, and one was a Valentine's Day card.  Both had heartfelt messages expressing gratitude for her starting this new journey with me.

Red came down the steps into the courtyard, wearing a dark blue blouse, faded and tight jeans, cream-colored high heels, and sporting that shoulder sling I'd gotten used to seeing.  She saw me and came into the restaurant's patio, giving me a kiss on the cheek and a big hug with her available arm. She smelled great, looked fantastic, and was all smiles.  I suppressed every urge to act all giddy because I so wanted to play it cool!

We got caught up with her recovery process.  It had been two weeks since her surgery, and she still felt some intense pain, but with medication she could manage.  The meds made her a little loopy, and she told me she was "frickin' high as a kite right now." In fact, at the outset of our date, she popped half a pill because she was coming off the last one.  I offered to drive or walk her home after lunch, but she said she'd be OK.

I showed her the box and asked to open it to get a little surprise.  She looked inside. "Oh my God, is that a Sprinkles cupcake?"  I replied that it was, and she took it out.  "It's gluten-free too," I said.  "I love Sprinkles," she said, and she just dove into it without a second thought.  I laughed as she came away with dark icing and cake all over her beautiful white teeth.  She kept talking like that, mouth full of cake, and I realized that she wasn't kidding about being high.  After that first bite, however, she put it back in the box.

We also talked about her projects, both of which were delayed. Further, she said she was seriously out of money after having the surgery.  I was a little concerned that she might really need more help than I could provide, but she assured me that she wasn't looking for a more lucrative situation.  I kept that in the back of my mind, seeing as I'd seen her on the website not two days ago.  I couldn't really said anything about it since I was doing the same, and she'd clearly be able to see me there, but all the same that knowledge has helped keep me somewhat grounded in reality.  With this recovery, she has also been unable to work -- she works freelance in the legal field, the same as KC, and that she'd be able to get back to it in about two weeks, but it was going to be rough going.

We ordered our meals, which were delicious, and continued the conversation as it turned to the arrangement and our histories.  I very freely admitted that I had been a player for a long time.  "But," I said, "it no longer really held a whole lot of appeal for me.  I'm pretty much done, and I don't want anyone else."  I meant that, even though I continue to meet women.  "You're very patient to wait," she said.  "A man's got needs."  I agreed, but I said that I could wait.  I hadn't had sex with anyone since my last date with Sam, and neither Sam nor KC nor Sarah really appealed to me now that Red appeared to be serious in her intention to be with me.  Red explained that she'd be sexually out of commission for another two weeks, due to both the pain in her shoulder and the fact that the course of antibiotics she had taken to prevent infection had left her "kind of... dry."  "Like I said," I replied, "I'm not in a rush. I'm just glad we're here and talking and laying the foundation."  She said she was hoping to learn to trust me.  "You don't trust me?" I asked.  "I mean," she said, "we're working on it. It's working.  We're starting the process." She was trying to reassure me, and it was working.

As we finished lunch and I paid the check, it was clear that the relationship had begun.  It felt like no other arrangement had before.  Not even Leah, which might have begun as an experiment in this type of relationship but was fatally flawed from the outset. Not C/Hayden, and certainly not Audrey or CC or Jade. This felt, at least to me, like what my life would look like were I single and out in the dating world.

Lunch done, I paid the check and we hung out a little longer.  I was in no hurry to end this date despite having to get back to work.  Red popped another pill -- something for her illness rather than the pain -- and we just kind of gazed at each other.  There was a serious attraction working now.  "I'm very attracted to you," she said, "and I wish we could play today."  She removed her glasses, and I actually lost my breath for a second.  This was the first time I'd seen Red without her glasses in person, and I was literally astonished at how lovely she was.  "Good God, that face!" I said, which made her blush.

Finally, however, it was time to go.  I gathered up all the stuff I gave her, plus my own, since she had only one hand.  We walked around the courtyard of the office complex a bit, admiring the city views and a few landmarks she said she'd never seen before.  "Well," I said, "you've been sleeping for the past two weeks, that's understandable."  She laughed a little too hard.  "You're really high right now, aren't you? Sure I can't drive you back to your place?"  She politely declined, saying that while she was definitely loopy, she was OK to walk the few blocks back to her place.  At some point, I knew she'd invite me over, since her roommate was only there briefly each day to pick up her clothes for the next day, and sleeping at her boyfriend's place.  I could wait.

She walked me down to the parking garage to get my car.  While standing at the car, we finally, at long last, kissed.  Effortless, unhurried, sweet, sensual, and full of longing -- pretty much what anyone would want a first kiss to be.  "Careful," I said, "I can pretty much go all day at this."  We kissed once more and hugged, her bum arm in between our bodies, and said our goodbyes.

As I drove home I realized that the two-week wait to see her again was going to be interminably long. I sent a text to invite her to lunch for the next week.  "That sounds lovely," she replied.


Wednesday, February 10, 2016

Red's Two-Day Delay

Yesterday Red let me know that she was having a very challenging day in her recovery from recovery.  She'd run out of her pain meds and her doctor left for the weekend. Since she needed immediate help she went to the E.R. to get an emergency dose while she waited for her prescription to be filled. On top of that,  she was having a flare up of her illness which only compounded the pain.

Of course I took it in stride.  I offered to bring her the money, or anything else she needed. She responded by sending me a picture of her face,  her purple sleep shades pulled up to reveal her warm,  but tired eyes.  With no makeup she looked about 15, and it totally melted my heart.  I sent a note telling her we'd catch up again later.

About four hours later she texted me.  "I just woke up.  Sorry I missed you today." Again I offered to bring her anything she needed,  but she must have fallen back asleep.

Two hours later I reached out again.  "It's my chicken soup text.  I'm Jewish and this is how I roll." Got a laugh in response. "As I've said, if you need anything I'm here. I know you desperately want to keep your address private because I might be an evil dude, but the offer stands."

That was essentially how the conversation ended yesterday,  although she did ask if I could see her today.  Working out of town,  I replied,  but I'm in town Thursday, I said.

This morning I got a kissing  text, so I immediately picked up the phone.  We talked for about five minutes and she filled me in. She felt better,  slept all night,  and her illness abated.  She said that her pain was manageable and easier than her pain prior to surgery.  I found that amazing and courageous.  I asked if she was sure she could get out tomorrow to meet me,  and I again offered to come by.  "I appreciate that," she replied.  "When we know each other better." "Well," I said,  "that gives me hope." She said that she could not imagine not having new over at some point. "You're so sweet," she said.  "Not sure how you figured that out from a few phone calls and busting my balls over coffee for 20 minutes,c I joked.  She laughed,  thank God! "I read people well.  You're a kind,  generous,  and very sexy man,  and I'm looking forward to showing you how much I appreciate you." She said everything right, and I thanked her.

Next post will,  I hope,  detail our second meeting.

Monday, February 8, 2016

I've Found My Backup Backup

No that's not a typo.

Lemme 'splain: See, Red and I are about to embark on an adventure together. Last Friday night she texted to let me know the outcome of her first follow up with her doctor, post surgery. "Everything was great," she wrote. "They took out the stitches."  She added that she also had a meeting about her project, the one she had to delay due to the surgery, that also went well. Apparently, the recovery time might be far less than she thought.

I asked her if we were still on for our lunch. I got a great selfie in response, striking a tough pose in her shoulder sling and decked out in a black double-breasted blazer, her red hair tossed to one side and sporting those glasses.  Caption was one word -- YES -- with two big red hearts.

"Wow!" I replied, "sexiest woman in a sling. Ever."

She then sent me two more daring photos: the first was low-angle shot from her waist up.  She'd ditched the blazer to reveal a blue blouse that zipped up the front.  Only it wasn't zipped up all the way.  She'd pulled away the neckline to show the top of her breast.  I'd already gotten a good look at what she had up top on the day we met.  Still, I steadied myself for what would come next.  She did not disappoint: a full length shot, facing the camera sideways, wearing nothing but the blue blouse and a pair of black pumps. Legs. For. Miles. That creamy white skin and the red hair! I was fucking done.  This was the clearest signal yet that Red intended to begin this relationship and knew exactly how to keep me buzzed all weekend long.  Though I tried to get one more from her, she was done too.  I'm sort of prepared to spend the afternoon with her, and who knows what will happen?

While it seems that I have things sort of sewn up with Red, I'm still not 100% certain that I'm in.  She hasn't pulled out the fierce side of her since the day we met, I'm being vigilant to make sure that, if she does, I'm prepared.  I don't care much for that side of her, particularly now that she has clearly demonstrated that she is not someone to be fucked with.  If at our lunch she pulls out that icy persona to try to rattle me again, I'll have to let her know that she is clearly superior and that I'm putty in her hands.  If that humor doesn't break her ice, I will probably have to look elsewhere.

Which brings me to my headline!

Today I met another potential, a holdover from when I was previously looking.  I'll call her KC. We met for lunch at a restaurant across the street from my office.  Apparently the drive from her place bothered her, because the first words out of her mouth were, "Well that fucking sucked."  I laughed it off since traffic does, indeed, fucking suck.  She was the same age as Red, about the same height, but a brunette.  However, not slim like Red, but closer somewhat in body type to the SB who didn't even warrant a name.  Very angular facial features, but soft and pretty eyes.  She is definitely not on Red's level when it comes to beauty, but the pictures she's sent me so far were hot and she's very sexual.  I found it very intriguing that she uses sugar dating as her real dating experience.  "The majority of the people on [the sugar website] aren't looking for something serious.  And I'm just not interested in a relationship right now. I like doing my own thing."  Plus there's the financial incentives which do satisfy a current need for her.  She said her overall sugar experiences so far were good.  She works freelance in the legal field, out of her apartment (which she does not share with anyone!). Our lunch today was casual and not at all flirtatious.  It was surprising to hear her say that she was shy, but that is not at all how she came off.  By the end we said we were both interested in the next step, and we made a tentative date for next week.  I can't say I find her attractive in the way I was/am attracted to C/Hayden, Leah, Sam, or Red. But she's at least as attractive as Sarah, and she's at least as intelligent as any of the other women.  In other words, I'd do her, and I think we'd have a great time for at least a few months. That's a good definition for a backup, n'est-ce pas?

So now it becomes a question of who'd be my first backup? Would it be Sarah, or would it be KC? On the one hand, Sarah and I have great rapport, and I like her slim little body and her personality, but with her boyfriend and the fact that she lives off my beaten path, I'm tempted to put KC first.  On the other hand, Sarah is more my body type, she's got a great sense of humor, and her shyness is something I find delightful and sexy.  One of them will be my backup to Red.  More later on who it turns out to be.

The backup to the backup, then, is Sam, on whom I can always count to be available on short notice.

I am definitely not interested in any kind of one-off thing with either of them.  If Red and I sleep together, they're both out.  Red will have a few chances to say yes to sex with me, but if she doesn't want to consummate our arrangement by the third date (tomorrow is our first real date), she's probably not that into me, and I'll probably have to rethink my priorities again. Now the trick will be figuring out how to stall these other women until I see where things fall with Red.

Thursday, February 4, 2016

Lunch With Red, a Preview

Red and I scheduled a lunch date for early next week.  I will be giving her the full allowance we have agreed on and we will not be having sex. As I've written before, all but one of my dates in the past eight years that involved the exchange of money has resulted in my having sex with whatever woman I'm with at the time. The only time that it didn't was in late 2012, when Wanda had a yeast infection and I agreed to postpone the date and leave her with the money.

Such, however, is the beginning of my paradigm shift. All these years I have seen my sugar involvement as little more than a sexual outlet. As my marriage to DW has become less and less sexual -- to the point where now we have gone more than a year without it -- I looked to the sugar life as a way for me to have sex with a woman without any commitments other than the promise to provide her with modest financial support. And, without apologies from me, it has largely been a spectacular success. I have had four arrangements in the past eight years that have lasted at least six months.  CC, my first arrangement, was totally open sexually, totally amenable to whatever we did together, and never showed me an ounce of negativity.  C/Hayden lasted for three solid years (during which we probably spent close to a year apart either through breakups, her travelling, or her recovering from an STI), and felt for a brief while like a real relationship.  Jade and I held on for ten months (with two months off in the middle while I saw Sam) until I could no longer deal with her lying and irrational choices (in other words, the fucking I was getting was not worth the fucking I was getting).  Audrey and I spent 15 months together (with a few months off at the outset while she got her own place) until I destroyed it with my indiscretion.  Sexually, every single one of these women satisfied me completely, and I got to do things I had never (or very rarely) done before.

After a year during which I found myself bouncing from hookup to hookup, I met Red, who in just a few short weeks has literally altered the way I want to think about sugar dating. Her only experience as a companion to a married man was a two-year affair, where she called herself his "mistress." She loved him, and still stays in touch with him although the relationship is long over. In short, I want what she had with her previous lover. Red knows this, and constantly tests me to see if I'm ready for her. I can't say I've performed excellently: I stumbled over my words and made a poor first impression at our first face-to-face meeting, and I still struggle with recognizing her time and place boundaries.

For example, I asked her yesterday to tell me if she wanted me to leave a little extra time after lunch to spend together, hinting that a great museum was nearby the restaurant.  She replied that she was "up/down with the pain meds" post-surgery and couldn't commit to anything. I said that we'd play it by ear.  "I know it's killing you that we can't be together for awhile," I joked, "but we can hold hands, no?" "I prefer not to do PDA," she replied.

This little exchange showed me her certainty about what she wants and that she will defend her physical and emotional boundaries. I've pushed the envelope for so many years, constantly testing the limits of what I can or can't do within the context of a sugar relationship, it's now challenging for me to look at this particular relationship differently. As I wrote before, even if Red and I do not wind up in a relationship, I believe that I'm supposed to learn something from this experience with her. If I blow it, I blow it, but I'll take those lessons to the next opportunity and try to do better.

I may occasionally find myself with more than enough opportunities to play with any woman who will have me, but if I'm going to be serious about success with Red, I have to put that stuff aside while I work on being the best she lover she's ever had.

Tuesday, February 2, 2016

Red's Recovery

I got a text from Red today, a picture that someone had taken of her riding a LifeCycle machine at the gym.  Her shoulder remained in that huge sling, but she had a sweet smile on her face and flashed me a peace sign.  The sling was connected to something called a Polar Care Cube which provides cold therapy to improve healing and reduce pain.

I was happy to see her working out.  "Love it! When do you want to see me?"

"Next week," she replied.

"Pick a day."

"I can't yet, babe Taking it day by day."

I wasn't going to push anything since she was less than a week out of surgery. "OK.  Just thinking of your deductible and wanting to support you."

"You are too kind."  I found this response curious, since in my head, at least, it was the primary reason why she had wanted to see me before her surgery.

"We are doing this arrangement thing, right?" I asked.

"Yes," she replied, "you're thoughtful."

"Well, this is what I'm happy to do!  You're my girl."

So I guess I'll content myself with more texting, and maybe I'll do some more flirting.  Something tells me, however, that she is too busy for that and won't engage for more than few texts.

Meanwhile... I've set a date to be with Sarah for this week.  There's a good chance I'll cancel it but we'll see.  She seems very down to fuck right now.

Monday, February 1, 2016

Backups to My Backups

The Sugar website I use sends me email notifications each time a sugar baby views my profile. I get four different notifications: when a woman simply views my profile, when she views and then requests access to my private photos, when she grants me access to her private photos, or when she sends me a message. The women also get the same notifications.

A few nights ago I received a notification that someone I'd viewed a while back had granted me access to her private photos. Ever the voyeur, I clicked over to see what other treats this woman had behind the privacy curtain. What she showed me was unimportant; I want to focus in this post on what happened next.

Since I was on the site, I thought I would kill some time to see who was online.  Sometimes I see new members, or I see members I chatted with before who were still looking. The first profile that came up was for Sarah, the cute east coast girl who holds the distinction of being the first potential to hesitate to accept my allowance offer after meeting me. It was that hesitation that I used as a reason to reject her and go instead with Fleur.  That turned out to be a huge mistake, which led to another with Rachel, then another with Natalie, and finally another with the SB who didn't even warrant a name. I joked in my earlier post that Sarah's rejection of my offer was perhaps an indication that I was slipping.  Well, four one-off encounters, thousands out of my pocket, and no sugar baby?  I was slipping, and had slipped.  It took meeting Red and sleeping with Sam to get my feet back under me.

Had I pressed Sarah to accept, instead of giving her an out, perhaps I would have had more luck. She was, after all, into me and we had a really good rapport. But enough armchair quarter-backing!

With Sarah still looking, I decided to reach out: "Hey, Sarah, hope you're well.  Looks like I didn't make the best decision, because I'm now available again. If I didn't offend you too badly, perhaps we can talk again? I no longer have your number but you might have mine."  She replied, saying she'd also lost my number. Dubious opening, but I sent her my number anyway.  Within a few minutes she sent me a text.  I asked her if she'd found a job, and she said that she'd been doing well with freelance gigs. She asked how my arrangement life was going.  Didn't waste any time, did she? I let her know that I was frustrated (which was partially true given the delay I have with Red without any real assurance that she and I are going to be together).  She wasn't with anyone, and asked if I'd been upset with her and had canceled for that reason.  "I have definitely thought about you," she wrote.  I asked how things were with her boyfriend, and she replied that they were still going strong, but that he didn't know about her plans to be non-monogamous.  "How delightfully sneaky," I wrote. She tried to draw an equivalent on my eight years of sugaring, but I was having none of it.

Over the next two days we texted back and forth, and we traded some new pictures.  She's still not the cutest girl I've ever seen, but I've met her and she's prettier in person.  We had a phone conversation and it felt really comfortable.  We continued the chat by text after we ran out of time to talk, and things got more sexual than they had before.  In the end, we agreed to meet for an intimate date this week.

I'm not quite sure what I'm doing here.  I've been talking about how I need to shift my thinking to have a relationship with Red, but what if Red's not the girl for me, or I'm not the guy for her? I need to have a backup plan. I'm not justifying it in any other way. With Sarah and Sam as backups in case things don't work out with Red, it saves me the time of having to go back to that website again and look some more.  Hell, I still have four days left on the site before my 30 day membership expires. I may go back and look for a backup to my backup!  It's definitely not the ideal way to go about my paradigm shift, but I'm making progress in focusing on girls with whom I want to have longer arrangements.  As I wrote earlier, "[T]he 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.'"