Monday, November 30, 2015

Quick Update on My Sugar Daddy Doings

Rachel and I had some brief texting before and just after Thanksgiving. She achieved a major educational goal, and she sent me a picture of herself at graduation to share the moment with me. Felt nice to be included in that process, unlike C, who could not bear the thought of my being at her college graduation even though I promised her I'd be completely incognito.

I texted Sarah a couple of days before Thanksgiving to let her know that I had, after some thought, decided to move on after all.  "It was not an easy decision," I wrote.  "In the end it came down to deciding between someone who had hesitated to accept my offer and someone who hadn't. Sorry it wasn't you. All the best to you."  "No worries," she wrote, "I figured as much."  And she wished me good luck as well.

Thanksgiving dinner was a blast at my house, filled with over 20 guests, family, relatives and close friends.  Polished off more than a few bottles of good wine, ate some great food (I'm an excellent cook), and laughed a lot.  Everyone left by about 8 pm, so DW and I had some time to start cleaning up.  The rented dishes, glasses and cutlery were rinsed clean and put away, the leftovers wrapped up and stored, the folding chairs and tables put away in the garage.  We swept up, mopped the kitchen floor, cleaned the countertops, and got the kids to bed around 10 pm.  I was so full of food I had a hard time getting to sleep that night, and we had a busy day the next day.

Late that night I was on Facebook, and I saw that Leah's mom posted what looked like fun pictures of her two kids horsing around, and then a picture of Leah lying on a hospital gurney.  A joke, I thought. But then I started reading the comment thread, and it turned out that Leah's sibling had accidentally dropped Leah on her head, which necessitated a trip to the ER.  Worried, I texted Leah the next morning.  "Hey, it's me.  Breaking my silence cuz I saw the pics your mom posted on FB.  You OK?" She replied that she was, just in a good deal of pain.  "So sorry," I wrote, "but at least I get to ask you if you've ever been dropped on your head."  "LOL," came her reply.  "Good, made you laugh," I wrote.  "I'll disappear (again) now, but I'll re-emerge if there's anything you need.  You're awesome."

Leah wrote back a few minutes later: "Thanks.  Maybe I should reconsider seeing you again."  As it was kind of early in the morning, I needed to read that last line twice to make sure I understood it. Was she serious or not?  I decided to straddle the line. "Do NOT toy with me, young lady.  You know I'm always down for that."  She sent back a winky face, suggesting to me that she wasn't too serious, but only she knows for sure.  "OK," I wrote, "it's entirely up to you.  I'm sure you remember that we did have some fun there for awhile.  I sure do."

So maybe she's down, maybe not.  I decided to refrain from reaching out to her except to check in to make sure she's feeling better. Keeping it light.  Two days later I just texted a hello, asking her if her head bounced when it hit the floor. She thought that was cute. I'll wait another couple of days before checking back in.

On Sunday afternoon I decided to reach out to Natalie.  As I really wanted to meet her before I completely committed to my arrangement with Rachel, I wanted to set up a meet.  Since she had earlier wanted to meet on a Monday I needed to text her now.  I had a scheduled dinner with my buddy Luke, and if Natalie was free Monday, I'd have to cancel my dinner with him.  We had a great conversation that lasted about half an hour, and we agreed to meet on Thursday instead of Monday. I am so excited to meet her, I am having difficulty even thinking about Rachel right now.  Plus, of course, in the back of my mind, I can't stop thinking about Leah and possibilities there.

Natalie has already agreed to my terms, so the meet will be free of that awkwardness.  We'll just be feasting our eyes on each other.  She keeps telling me she finds me very attractive.  Her profile specifically states that she finds men in their 40s and 50s to be much more desirable than men her own age (early 30s).  Personally, I just can't wait to put my arms around her and feel her close to me.

One of my readers wrote me earlier that he's found himself rooting for specific Sugar Babies throughout my blog, and that sometimes he picks correctly.  I wonder for whom he's rooting now.

Friday, November 20, 2015

Rachel Rocks

Here's a taste of the "story of my life."

I'm walking from my office, located in a large complex of five 12-story buildings, to the hotel located right next door.  Had the best deal and was a major chain to boot.  Score. As I'm walking, bag slung across my right shoulder, jacket neatly folded up over my other arm, I feel the familiar vibration of a text message coming in.  As I'm about an hour from Rachel's arrival time, I thinking she is texting me to tell me that she's leaving wherever she is to meet me, can't wait, yadda yadda yadda.  I look down at the phone, swipe the screen, and here's what I read:
Heyy.  Are you still into this and you're just taking space or have you moved onward?  Sorry to be blunt! :-)
It is Sarah, the first potential I met with about two or so weeks ago.  I really liked her, but when she hesitated to accept my terms I sort of did actually move on.  Then her boyfriend came into town and we maintained a safe distance for a week, but during that time I had found Fleur, Natalie, and others.

I am faced with a choice: tell her now, or wait until after I hook up with Rachel.  I decide to wait: "No worries," I reply.  "It's not my style to be silent like that.  If I'd have moved on I would have told you."

So she's put off for a bit, but I'm pretty sure she's done.

I got to the hotel an hour early because, frankly, I felt exhausted, wanted to shower and then rest for a bit.  After checking in, I texted Rachel the room number and offered to meet her down in the bar or up in the room.  She said she'd meet me upstairs.

Rachel then texted me two minutes before she was supposed to show up to let me know she was parking.  A few minutes later there was a very light knock on the door.  As I opened the door she was all smiles, looking as cute as she did the other day.  She wore no makeup at all. She wore black yoga pants, a brown blouse with buttons down the back, and a black cotton yoga top underneath.  She came in, gave me a light kiss and I followed her into the room.

We lay on the king-size bed for a few minutes chatting.  I said, "Y'know, we're gonna have lots of time to talk, like after, so why don't you just kiss me now?"  I had been waiting for days to kiss her, and my expectations were blown away.

Let me take a moment now to say that Rachel has some definite physical negatives for me.  First, she has two large, unsightly tats on her body.  The first is on her upper back and stretches from shoulder to shoulder.  There's an inscription that I can't remember tucked in among a whole hot mess of flourishes. Frankly, it's hideous. The second tat run from her left hip bone to the middle of her thigh. A biblical inscription from the Book of Proverbs amid three large roses, one for each of her nieces.  I know that I've been very descriptive of these tats, but whatever.

Second, Rachel has very soft breasts that have no perkiness at all.  Very sensitive and she likes having them kissed and the nipples pinched and sucked/kissed, but they're floppy and at her tender age, she'll probably need a lift after she has kids.

Third, she has hands and feet that I would call indelicate.  Like she's worked with horses, or done a fair amount of jack-hammering in her life, as well as some serious ballet dancing en pointe. I'm not particular about hands and feet, per se, but I see well manicured nails and smooth skin as a sign of girliness and femininity, both of which I like a lot.  Rachel is not girly in any way; she's womanly, and carries herself maturely and serenely.  She's an earth mother, and I find it wildly attractive.

On the positive side, her bright blue eyes pierce when she looks at me.  Her teeth are perfectly straight and white.  And those lips.  Oh, dear God, those lips.  I said to myself when I met her, I gotta kiss those lips.  I'll bet they're like soft downy pillows that I can rest my lips on for days without end. I did not want to stop kissing her the entire time we were together.

Once we started making out, it didn't take long to get naked. She was eager to take off her clothes, and wasted no time undressing.  I kissed her body everywhere to taste her, to gauge her responsiveness.  Hips were rocking, good sign!  I rubbed her between her legs to feel her wetness, and she did not disappoint.  Eventually I got my face down there and feasted on her.  She played a lot with her nipples, so I started joining her with my hands while I went down on her.  She came at least twice, legs in the air, hands gripping the pillows on either side of her.

When she went down on me, I half expected myself to come immediately with those lips.  She also had a pretty large mouth, so I knew she'd be able to take a lot of me in.  Her talents rivaled Joni's, the girl who gave me the best blow job I've ever had.  But she kept stopping every 30 seconds or so to kiss me.  I sensed that she wanted to be done and have me inside her, but I was not having it. "You are so good at that, baby, please don't stop yet!"  She practically took all of me in her mouth, using her hands expertly.  Her touch was light, but oh my, she knew exactly what she was doing.

When it came time to fuck, I slipped on a condom and said, "No need for lube down there, Miss Wetness."  She laughed, but that quickly faded into moans the second I entered her.  Fucking and kissing, kissing and fucking, missionary, side by side, and cowgirl. She came over and over.  I didn't count, but she said it felt like ten times.

Afterward, we talked about her work.  When I say she's an earth mother, I truly mean it. The woman works with women's health, holistically and organically.  I totally dig that!  And I let her know how much after about half an hour, when I decided I wanted to fuck again.  We used lube this time, but not a lot, and we came together while she rode me.  I pulled her body totally against mine at the end and I felt her breath on my neck.

It was a great first time together, and I'm so looking forward to another date with her.  She appreciated that I slipped the envelope in her purse (and actually had an envelope; her last SD just handed her a wad of cash each time -- how charming).  I showered after she left and quickly made my way to my car and home.

When I arrived, DW and the kids were out to dinner and attending a charity event, so I decided to write all this while I could remember it clearly.

My next step is to meet with Natalie next week.  If we can't get together next week, I'm not sure I'll push to meet the following week, as I'll take it as a sign that our schedules are a little too incompatible.  Next week I'll text Sarah that I'm no longer available.  She won't be happy but she won't show it.  It's too bad, because I really liked her.  I think if we'd managed to have sex before her boyfriend came to town, I might have made a different choice.  But I'm very happy with Rachel; good woman.

Thursday, November 19, 2015

Going Against Type

In my last post, I ended by promising to fill you in on the two newest potentials, Natalie and Leira.

When I saw Natalie's profile on the website, I had an instinctive attraction to her.  Her profile said she taught yoga and worked in "hospitality management."  Her pictures revealed a slender, shapely petite body and a lovely peaceful face.  She was in her early thirties and I knew she would be special.  We quickly agreed to terms, exchanged phone numbers and started texting.

Scheduling has been difficult.  We had a date scheduled for earlier this week (the day I ended up with Fleur), but because of my commitments that evening, I had to postpone.  Natalie had to leave later in the week for a retreat of some kind, and we rescheduled for this coming Monday.  There may be more here, but in a small way I have doubts that things will materialize.  Her home and work are currently out of my way, but when I transfer offices next month she'll be much more conveniently located.

Leira is a mid-twenties goddess: tall, brunette, blue-eyed, and with a bright smile that had me hooked. Her pics revealed a dorky girl with an elegant side.  We also exchanged numbers and agreed to terms and then started texting.  I had a great chat with her during my morning commute, and we made a date for late this week.  Then came a slightly cryptic note from her: "Since it's kinda far off, let's wait till next week to confirm."  Reading between the lines, I joked, "Of course, need to give some time for a more lucrative offer to come along."  She sent back a winky face emoji.  I was doubtful that anything would happen, but I had hope.

On the day I promised I texted her to confirm that she'd be available to meet after work.  "Sorry, but I'm no longer available," came her reply.  Ah, my instincts were correct, and I felt satisfied.  "No worries, babe, but please keep my number handy.  It's been my experience that these things tend sometimes not to last too long.  Richer SDs get bored more quickly."  She replied, "I will, and thanks."

Back to the website I went.  With Fleur gone and with Sarah still doubtful about my offer and with me losing interest in her, I figured it was time for me to check things out some more.  There was still Mel, half Asian and Mediterranean who grew up on the east coast (exactly the same as Jade, actually).  She and I had exchanged some hot conversation (she's fully bisexual) and I'd made and broken one date already, so I scheduled one with her for today as a backup plan.  I liked her pictures, but something told me she was a little less in shape than I like.

In my search I ran across Rachel. She was in her mid-twenties and lived close to where I currently worked.  With my transfer, I'd only be in that town twice a week, but that was enough to consider her. Interestingly, she is also a blonde, blue-eyed beauty, which is totally against type for me.  Readers of this whole blog will note that of all the women I've been with, only CC and Lola were blonde.  Everyone else has been brunette.

I sent Rachel a message and she responded a day later.  She expressed concern over my being married but said she was still interested in meeting. I offered her an opportunity to express any reservations she had, but that I'd successfully managed many years of arrangements around my marriage.  She agreed to meet, so I sent her my phone number and she texted me right away. We made a date for yesterday after work to have a drink.  She lived just ten minutes away.

Rachel met me outside the bar.  She was about 5'5" and had shoulder length blonde hair and bright blue eyes, plus a sweet toothy smile.  I liked her immediately.  We grabbed a table and I ordered wine, but she only wanted water.  I learned that she was beginning a business of her own and currently lived with a parent while she completed some necessary training for licensing.  Her profession really impressed me.  It revealed that she was much more mature that about 90 percent of the women I've met so far (reminded me of C, in a way), and that she had a warm, giving nature.  She called herself a "healing nurturer" and a hippie chick.  I just smiled, impressed and very intrigued. The more we chatted, the more I really wanted her.

I asked Rachel how she envisioned an arrangement.  She threw out a number that was triple what I was willing to invest.  I said, "Well, that's more than I'm willing to go.  That's more of a number that would justify one or two meetings a week, but I'm only looking for twice a month."  I then offered her my standard $1,000 monthly allowance.  "Oh," she said, "I had sort of counted on twice a week, but this works too." I mentioned that non-exclusivity was okay by me too.  She liked hearing that, and said, "I really like the fact that you are so up front about all this.  I appreciate your honesty."  I replied, "Well, I know you're going to think about it, so just let me know one way or another."  Since I had other options, like Mel and Sarah, plus others if I kept looking, I was not going to be broken up if she said no.

I paid the check and then walked outside with her.  We hugged a little and I told her to text me when she had made a decision.  Before I got home, I had my answer.  She agreed to my terms!  "I just really liked you and would definitely like to meet again."  I asked, "Do you want to meet casually again, or go for something more intimate?  I'm fine either way." I meant that, too.  I liked Rachel. She felt really warm and engaging, friendly, and she was definitely stunning.

The next morning, she texted that she wanted an intimate date, so I booked a hotel later in the day for the next day.  I cancelled on Mel again, and she was not happy.  She didn't get me, however, when I wrote that I was "no longer available."  She said, "Well, this is the second time you've canceled on me, so if you want to get together just let me know a couple of hours ahead of time and I'll let you know if I'm available."  I won't be contacting her again.

By this time tomorrow, Rachel and I will have consummated our arrangement.  Once that happens, I'll let Sarah go.  I will still meet with Natalie, if she's available, but I think Rachel's the one.

Sunday, November 15, 2015

The End of Fleur and Al Capone's Vaults

Back in 1986, Geraldo Rivera hosted a one-time TV special called "The Mystery of Al Capone's Vaults."  It was one of the highest-rated TV programs of the year, but was ultimately a total washout, because once the vault was opened, it revealed nothing but dirt and an empty bottle of liquor.

Now I know in my previous post I wrote that I would post the actual text messages between me and Fleur as I broke up with her.  The result, unfortunately, is anti-climactic.  I could have prompted some drama by being overly critical, but I wouldn't have felt good about it afterwards.  The voice inside always tells me that a man must end a short-term, recreational relationship "quickly and honorably."  Revealing how I'd actually felt about our single encounter could have provoked some negative comments from her, and maybe it would have made for fun reading here, but ultimately I think it would have been unnecessary.

So, with all the fanfare of a vanilla ice-cream cone, here are the actual texts between me and Fleur this morning:

So it was all over in about as much time as it took for our entire sexual encounter.  And I couldn't be happier.

In my next post, you will read about my meetings this week with two new girls: Natalie and Leira.

Fleur Fails

Have you ever been in a situation that had initially shown so much potential, but wound up being a total disaster?  That no matter how much hope you had invested in the outcome, it steadily headed in the other direction?  So went my first and last encounter with Fleur, the "29-year-old" Asian woman who I had thought was charming, attractive, and sexually interesting.  I put her age in quotes because there was no way in hell she was 29.  With her long, stringy, black hair that was showing a few strands of gray, her complexion, and eventually, her body, she was at least 40 if she was a day.

Fleur met me at a hotel that was on my way home from work.  I'd given myself an hour to get there, but it took me an extra 10 minutes to arrive, including a stop at an ATM for the sugar.  The hotel had a penthouse bar and she sat on a stool taking in the 12th floor view as I arrived.  I tapped her left shoulder and came around to her right.  When I saw her face, I did my best to hide my shock.  Her pictures were extremely flattering, and the woman I saw was reasonably attractive, though not as attractive as her pics indicated.  Perhaps she was like Ug-Lee whom I had met more than six years ago, who had posted older pictures of herself and lied about her age.  Fleur was certainly thin, in her blue striped blouse, orange skirt and high-heeled shoes, so she hadn't put on a bunch of weight.  But sitting there, with her black horn-rimmed glasses, she looked like an accountant who'd just finished with a long season of tax preparations and wanted now to enjoy a naughty time out.

She'd been nice enough to get me a soft drink -- heading home immediately after our date, I didn't want alcohol on my breath -- and we took a few sips before I suggested we adjourn to the room, which was one floor below.  When she stood up she stood a few inches taller in her heels than I did.  I figured we were nearly the same height, like other girls I'd enjoyed in the past.  She had long legs that her skirt flattered, and she looked curvy enough.

In the room we chatted about her sugar past.  She'd had a long term arrangement with a married man, and had actually met AND FUCKED the man's wife during their time together.  It shocked me and made me more attracted to her, but that lasted for only a few moments.  At the height of my attraction, I leaned in and said, "Kiss me."  We had some good kisses for awhile; she was talented. However, things went downhill from there.

Rolling around on the bed, we got our clothes off.  Her breasts sagged once released from her underwire bra -- gravity and age.  Her skin was smooth, but even in the cold room she started getting sweaty and clammy, and it only got worse.  I decided once she was totally naked that I would not go down on her.  I'd fuck her, but this would only happen once.  She had pretty decent BJ skills, but all I could think about was that old joke: "How is walking a tightrope across a 600 foot deep ravine the same as getting a blow job from Whoopi Goldberg?  For God's sake, DON'T LOOK DOWN!"  So, with my eyes closed, I pictured another girl sucking my dick. It worked.

Eventually, however, I needed to get off and get the fuck out of there.  I slipped on the condom and had her get on top.  She had no rhythm at all.  As I pulled her closer to control the movement, I noticed how sweaty she had become, and I didn't want to put my hands on her anymore.  I rolled her onto her back so I could avoid touching her, but then I really could not avoid her face.  I'm telling you it was a fucking nightmare (literally!).  She was not flexible so her legs couldn't get that far apart.  I knew I had to come soon.  I buried my head on the bed beside hers and pumped away for about a minute, concentrating solely on how her pussy felt.  She was tight, and it worked.  I pulled out, slipped off the condom, and blasted jizz all over her.  I went and got a towel so she could clean off.  

Both of us showered and talked a bit more.  One redeeming quality was that she had the same taste in music as I did, and we had a great time talking about the bands and songs we liked.  I actually liked her as a person, but I couldn't see ever fucking her again.  During the conversation, I gave her a chance to tell me the truth about her age by revealing that my online profile shaved a few years off my real age.  But she maintained that she was 29.  Eventually it got a bit late and I had to go.  We dressed quickly and hustled out of the hotel, riding the elevator down together.  I hugged her in the parking lot and raced to my car, muttering to myself the whole time, "Why? Why didn't you just stop when you had the chance?"

I deeply regret having gone through with this date.  I should have trusted my gut once I saw her in the flesh that she and I should not move ahead.  It would be simplistic to chalk it up to being hard up for sex.  I know I really wanted it to be better than it turned out to be.  And I kept hoping things would improve. But they really never did.  Even being inside her was a disappointment.

Now, I have to break it off.  I can't wait for it to be done with.  And, for the first time, I'm going to post the actual text messages as screen shots so you all can see exactly what transpires. Stay tuned.

Friday, November 13, 2015

Leah Bolts

I didn't quite predict it, but I certainly set the stage in my previous post that there was a possibility of Leah backing out of a renewed arrangement.  I thought it might be because of her reaction to my texting.  And yesterday she did not surprise me.  After I texted her to tell her where to meet me today, she wrote back that she'd thought about it and, because of the fact that she was now living with her mother, it was "too risky" to see me again.  I quickly shot back: "No worries.  I sort of knew this was going to happen.  It's unfortunate that you were put off by my excitement and nervousness.  But nice attempt to blame it on something else.  Goodbye (again)."

After a few hours of deliberation, with the help of a reader, actually, I'd decided to give Fleur a try. As she and I hadn't agreed on terms, I texted her that if she was available we should meet.  She was thinking the same thing, and she offered an allowance that was considerably less than what I was prepared to invest.  I accepted, but I have it in my mind that perhaps she lowballed herself to tamp down any potential disappointment.  Or, perhaps, she doesn't really need that much money.  Either way, I'm not committing to an arrangement just yet.

I met a new girl last night.  Details to follow.

Monday, November 9, 2015

We Get Mail

A reader wrote:
In [the] last month or two of blogs you definitely come off as needy or clingy.
I can definitely see how true that is now.  Not sure where it came from, actually, but it was there. Transitions can do that to a man.  I remember when C left and I hit a milestone birthday and changed jobs, all at the same time.  It hit me hard, and I was practically non-functional for about a month.  I've been two months in a new job that is kicking my ass (in a good way), I'm nearing 12 months with no sexual contact with DW, I have had sex only once in the past two months (with Sam), and I'm commuting nearly three hours a day.  Stress?  Naaah!

This note from my reader definitely woke me up though. I resolved today not to initiate any text conversation with any SB unless it was going to be to set up a date, and to be the first one to put an end to any text conversation.  I did this first with Sam, who was in town and available.  I wanted to create options in case Leah backs out.  I asked if she was in town, and she said she was, but just for a couple of days, which wouldn't work for me.  We established that she'd be in town a day next week and I said that I would text her the day before to confirm her availability.  Then, I said, "Take care, sweetie. XO." and that was it.  It lasted all of four or five texts.

I did this again with another girl, whom I'll call Fleur.  She was a late-20s Asian beauty.  We struck up a decent convo, and set up a date for Friday, and then I cut it off.  "Got to get to work, hun.  I'll confirm with you Thursday afternoon. XO."

And again with another who I won't name because I'll probably dismiss her anyway.  She was a blonde early-30s model, gorgeous, accepted my terms, and agreed to a Friday casual, but too much travel for both of us and I don't think she'll do that regularly.  I told her I'd confirm Thursday, which I will do only to cancel.  I just wanted to get back in the habit of keeping it brief.

Finally, a girl named Mel, late 20s Asian mix. I texted her to ask if she was available this Friday.  She said she was, and I said I'd text her Thursday to confirm.  Took four texts to make that happen.

Sarah is entertaining her boyfriend who is in town all week, so I'm steering clear of that.

So I have a potential date with Fleur or Mel on Friday, or Sam next Wednesday, in case Leah backs out.  I think it was a good day.

Sunday, November 8, 2015

Stuff I (Still) Need to Learn About Sugar Babies (and Women in General)

About an hour ago I almost lost Leah as a Sugar Baby, almost as quickly as I had found her again. The area of conflict came from my sending her too many texts.

Not to get into specifics too much, but after one I sent her earlier today she wrote that she didn't think she could go ahead with the arrangement because it seemed to her that I was "looking for more of a girlfriend," and that wasn't what she could provide.

"That's not it at all," I responded, feeling a little anxious. "C'mon.  I'm just trying to stay in touch and keep you entertained.  Forgive me.  I'm just not great at this."  She wrote back that it was okay, and I promised to stay out of contact with her until the day before our date.

"No," she wrote, "it doesn't need to be like that, I guess not quite so regular though."

"No worries," I responded.  "It's just that I'd asked you to set boundaries, which I guess you're doing now."

Leah brings up a good point though.  If all we are is a sugar thing, should I as a Sugar Daddy expect her to communicate with me whenever I reach out?  If I text her daily to say hi, and she doesn't respond daily, I actually begin to worry that she is losing interest.  So, like a dope, I send more texts, till she gets pissed like she just did.  At this point, I think I've probably blown it and that she will tell me the day before that she's no longer interested.

Right after that conversation, I sent a text to another potential SB, Isabella.  An early-20s undergrad studying French and Art History, she and I struck up a very hot text convo two days ago.  We agreed to meet the week of the 16th, as I was hedging just in case things with Leah didn't work out.  Over this weekend. however, I reached out one too many times I guess.  Was I sending suggestive texts? No.  I was wishing her a happy Sunday and telling her I looked forward to chatting during the week. But tonight I asked her that if I was texting her too much, would she let me know directly or would she just stop communicating.  She started off by saying that some SBs like less, while some like more, and in the excitement of starting something new, sometimes things get a little too out of hand. I interpreted this to mean that she was telling me that I was bugging her.  I then asked her to confirm if I'd taken things too far, and eventually she said that perhaps we weren't as good a fit as we seemed to be at the outset.  I apologized, thanked her for her honesty and then said goodbye.  It was a huge disappointment given how positive things were at the beginning.

Once I got home, I then turned to Sarah, who even though I believed I would probably let her go, was now seeming like a decent choice in case Leah changed her mind.  When she didn't respond right away, however, I started to worry.  While then walking my dog, I started thinking about it, and I began to notice a pattern in my behavior.  I did this with C; she started telling me not to text her during the weekends, and then to text her only once or twice a week.  Part of that was that she was with her BF on the weekends, and that she was busy with work during the week.  But all the more reason to set a boundary around it.  Then Joni told me that I was texting her too much and only wanted to hear from me to plan the next date.  She accused me of wanting a girlfriend and being too emotionally needy. Jade would frequently tell me to leave her alone because she was busy at work. And who knows how many others picked up on it really early, before there were any meetings, and decided I was too high maintenance?  I also probably did it with Audrey, but she never said anything about it. And now these two.  I started feeling depressed.

Once I got back home from the dog walk, Sarah texted me.  I asked her directly: "Am I texting you too much? Are you getting sick of my texts?  I am concerned that in my enthusiasm to attract you, I'm doing exactly the opposite."  She wrote back that she liked my texts and didn't think I'd gone too far. She asked me if I thought she was not texting me enough.  I guess every situation is different, right? I said that I was just going through a bit of insecurity, and she apologized if she was making me feel that way. Sweet girl.

Maybe I'm just in my head.  But it reminded me of sage advice I was given during my single and dating days before meeting DW: when chatting with a woman you are dating or want to date, never have more than a five-minute conversation on the phone.  Spend just enough time to plan the date and then end the call.  Leave her wanting more time with you.  I have not really been following this advice at all.  Time to stop acting like a puppy dog and be a man.

Friday, November 6, 2015

A Sugar Baby Return!


Me: When you say we can definitely stay in touch, is there a boundary you have in mind?  Do you mean, every so often, or whenever we get the urge, or?

90 minutes later

Leah: I'm not sure exactly what you want out of talking to me again.  If you want to start another arrangement I am open to that but I'm letting you know now that my idea of what I'm open to has not changed and now my availability is very limited.  Meaning I won't have time for dinner or going out. Maybe occasionally but I know that's why we ended it last time because you wanted more than just the bedroom [ed. note: actually I ended it because she said she didn't have a serious bf when she did].

Me: I do want another arrangement with you.  I just didn't know how to approach you about it.  I know your availability is limited.  It can be occasional rather than regular.  And I've grown up.  If you have a bf, that's fine.  I'm also ok with just bedroom fun.

Leah: Haha good.  No bf. Probably won't have a bf for a while. No time to date.  So, a big thing that has changed is my living situation.  Obviously we would need to get a hotel.

30 minutes later

Me: I have no problem with that. OMG, is this gonna happen? Pinch me.

One hour later

Leah: :-)

Me: The terms would be the same, ok? I presume you have finals next month and are studying your gorgeous butt off.

20 minutes later

Leah: yes sounds good re terms.  I'll find some time.  :-)

Today, I texted Leah to ask her if she had time for a 5 minute phone call.  Early that afternoon she wrote that she was now available so I dialed immediately.  What a pleasure to hear her voice again!  I wanted to talk directly so that we could nail down scheduling.  It took all of a few minutes and we settled on Friday afternoons on my way home from work.  Our first new date will be next week. "Well, that was a lot easier than I thought!" I said.  I again apologized to her for how I'd treated her and she accepted my apology.  I can't say that we'll have a long time together, but even a short time is worth it to reconnect with her.

Ten minutes later I texted her:

Me: Holy shit, it feels like I just parted the Red Sea

Leah: Lol Yay!

Me: Was this something you had thought about too?  Because I was noticing that you were liking all my comments on FB.  I would have thought you'd do all you could to avoid me.

Leah: Aw, no, I don't hold grudges.  I wanted to remain cordial in case we ever saw each other at some event with my mom or something lol.  I did kind of suspect you were interested though after you made a few comments on FB about me lol "You have a very sensible daughter."

Me: I wasn't [interested] until I saw pics of you on her timeline, and I remembered the brief but wonderful time we spent in your little apartment.  I figured you'd still be with your bf, but when I realized you were living with your mom I knew you were "single" again.  I confess that at that point I had to see you.  But apologies first.  I've never stopped caring about you.

Leah: Well, I'm so happy you reached out!

Now that Leah and I are going to get back together, it means that Sarah and I will not be.  It's as it should be.  We had a fantastic lunch together yesterday, and I texted her afterward that I was kind of high on her.  She felt the same way.  However, we hadn't had that crucial financial terms discussion. She texted me that evening to ask if we could talk and I called her.  I asked her what her last SD had provided, and it was twice what I was prepared to offer.  When I gave her my number, she let out a groan of concern.  I knew at that moment that things would not work out.  I told her to think about it and get back to me.  She then asked if I still required exclusivity. "Of course not," I said, "I realize that my offer is less than what you want, so go ahead and see other men.  It might even be that I'm a temporary sugar daddy until someone else comes along who agrees to your terms."  She didn't quite agree, but I could tell that the wheels were turning and that she was disappointed.  No matter.  Now the issue for me becomes how and when to tell her that I've withdrawn my offer.

The interesting thing for me is that Sarah is the first potential SB who has not accepted my offer after meeting with me.  I must be slipping.

Thursday, November 5, 2015

The Sugar Search Begins Anew!

Last week I renewed my membership on the SD website.  Not really sure what I had intended to do, since my business is still kind of new and my cash flow inconsistent, but I guess I just wanted to see what was out there.

The talent pool continues to be mighty deep!  In my current search field, there are nearly 1,500 available SBs listed.  As I've said in the past, when one filters out the inactives, the ones who are unattractive, the ones who aren't attracted to me, the ones who want single men only, or the ones who don't like my financial terms, there are still at least 50 women to choose from.  I like those odds!

Here are some highlights in the current crop:

  • Belle:  I ran across Belle's listing with great surprise.  I didn't think she'd be doing that anymore. After all, I noticed recently on a website that she also was escorting.  But I reached out to her anyway.  I let her know that we'd been together before and that I'd like to see if we could try again. At first she didn't recognize me, but when I told her that I'd seen her in a local Starbucks, she made the connection.  We actually set up a date for today, but just a few minutes ago she canceled due to a scheduling conflict and asked if we could meet tomorrow.  "No worries," I wrote, "We'll try again soon."  She then told me that she was unavailable after Nov. 19 with the holidays and final exams, then would be on vacation for a month.  "When I come back from that trip," she wrote, "I won't be seeing anyone anymore. New year, new choices." Although I feel slightly disappointed, I wished her luck and she did the same.
  • Sarah: A mid- to late-twenties east coast girl who had just moved here two weeks ago.  I wouldn't say she is the cutest girl I've ever seen, but there was something about her that just drew me in on her profile.  She was artistic and articulate.  She thinks I look like Michael Douglas. Well, that's a stretch, but I'll take it as a compliment!  One afternoon she agreed to keep me company by phone while I commuted the hour or so from my office to my house.  We talked about art, music (she's a writer), museums, and the boyfriend she left behind who will be visiting her next week.  We are going to meet after he leaves, but since Belle and I aren't getting together now I texted her to see if she was available to meet for lunch.  We're meeting this afternoon!  Can't wait to see her in person.
  • Edie: An early 20s Latina who lives right on my route between office and home.  Dark skin, short hair, and bubbly personality.  Very sexual, very cute, loves to send me pics of her body, which is tight and fit. Surprisingly bright too.  We haven't yet made a date, but I'll push for something casual next week.
  • Sports: she's still available and interested in meeting.  I'm less inclined to be with her because she is a bit older, but if nothing else works out I'll consider it.
  • Mel: Curvaceous mixed-race mid-20s, dark hair and eyes.  We're just getting started, but she's pretty hot.  More to be revealed.

There are a couple more who haven't registered anything significant, plus a couple who looked promising but then fizzled out.  One girl I was texting with had an objection to my profile name on the SD website.  She thinks that it sounds like "impostor" and suggested that I may not be legit.  I said it was a deliberate play on words, but perhaps I should rename myself to make it really confusing.  She didn't care for that.  I then gave her my first name and last initial and said, "You have my phone number; google me and you'll see I'm legitimate.  Let me know when you're satisfied."  Never heard back.  Another objected to my playfully sexual comments. "I prefer old school, respectful gentlemen," she wrote.  "Well," I replied, "that wouldn't be me.  I'm just a guy who sometimes can be socially unacceptable, but keeps his heart in the right place.  You're welcome to give me another try."  She asked for money up front to meet for dinner, and I said no, since I don't pay for the opportunity to be auditioned, so that was that.

Finally, there's Sam, who I really like and with whom I have a chill connection, but since that won't be anything regular, she'll just be someone I see occasionally on the side (when the lighting's right).

I will not include Leah in this group.  One, I have no idea if she's even sugaring anymore, and two, I'm not sure she'd agree to see me if she were.  However, I texted her last night to wish her sweet dreams, and that I'd be happy if we could stay in touch. She replied that "We can definitely stay in touch."  Be still my beating heart.

Wednesday, November 4, 2015

Hello Leah

Recently, I re-connected with an old friend on Facebook.  It was Leah's mother, on whom I'd had a major crush when I was 15.  Leah and I hooked up through the sugar daddy website for a couple of months.  She was an undergrad student in her mid-20s, experienced in sugar and living in her own apartment in the center of the city.

It was an intense connection, one I severed because 1) it was hard to let go of the fact that Leah's mom was a friend, and 2) I'd met Belle and she was more desirable than Leah, being closer in age and not related to someone I already knew.  Leah did not like the fact that I ended things, even though she took being dumped graciously.  Three months later, however, I wanted to see her again, and I managed to convince her to see me again.

The day before I last saw Leah, she told me she was dating someone, but that it wasn't serious.  The next day we had a beautiful time together, and she had her first orgasm with me. When I casually asked her about the dude in her life, though, she revealed that she'd made him wait two months before she had sex with him "to see if he was serious." I took that to mean that she was, in fact, in a serious relationship with him, despite what she'd told me the day before.  I got upset and told her that I couldn't see her anymore, which upset her because it had taken some convincing to get her to see me again.  She said a couple of hurtful things, most notably the inconvenient truth that single women who sleep with married men only want two things: to break up their marriages or to take their money.  I turned that comment around on her, accusing her of being nothing more than a prostitute.  It was an ugly confrontation, one that resulted in my leaving her apartment and taking back the money I'd brought over.  I went home that afternoon and unfriended her mom, deleted all of the pictures Leah had sent me over the months (you might recall that I thought she was probably as beautiful, if not more so, than C), and erased her from my memory.

Then earlier this year, one of my oldest friends died of a heart attack at 52 years old.  She was the first girl I'd met upon moving out west, and the first friend I'd made. We were pot-smoking pals all through high school, always close friends, and she turned out to be, on the day after my 18th birthday, the first girl I'd ever had sex with. She also happened to be Leah's mom's best friend all these years.  Leah's mom was devastated and I'd read her heartbroken Facebook posts.  Reading those posts made me want to re-connect with her, but I held off because the wound of the Leah breakup was still a bit too recent.

A few weeks ago, however, I reconnected with her, and we started commenting on each other's posts. I remembered why I liked her so much -- her dark humor, particularly.  But something else was happening.  Leah, her daughter, was liking my comments; she was liking every one of them.  I thought nothing of this at first, but when she started playing off my comments with some of her own, affirming what I was writing, it caught my attention. Was this a subtle sign that there might still be a connection?  Despite what had happened, she was still a really great girl.  Over the months, I have learned to relax a bit and not get so bent out of shape when sugar babies (or anyone, for that matter) says or does something that would otherwise offend me.  I guess inside I realize that most people don't really want to be hurtful or disrespectful.  And Leah was right; her relationship with her boyfriend, serious or not, had nothing to do with what she and I were doing.  My insistence on being the main man in her life, in retrospect, had been childish.

Leah occupied my thoughts for a number of days.  I wanted to connect with her in some way, and I'd even be open to seeing her again.  But first, I knew I had to apologize to her.  I struggled with the decision to reach out.  I'd lost her number, but by looking at old cell phone bills, I was able to locate it.

Armed with her number, I resolved to contact her.  But when?  And what would I say?  I knew I had to apologize, but I feared a cold shoulder, a sure sign that I'd misread her actions on Facebook.  It wouldn't be the first time I was over-enthusiastic like that.

Today, though, I just went for it.  I said hello, apologized for texting her out of the blue, and asked how she was.  To my great pleasure, she replied almost immediately, warmly, and openly.  She revealed that she'd graduated from college and was now pursuing her master's degree.  Because of the cost of tuition, however, she'd had to give up her apartment and was now living at home with her mother and stepdad.  This indicated, though didn't confirm, that she was no longer with her boyfriend from last year.  At her age, why wouldn't she just move in with him, when he lived closer to her school?  It wouldn't make sense for her to be living with her mother.  I didn't ask her that, however; too soon.  I then apologized with all sincerity, saying that I'd been a piece of shit to her and that she didn't deserve the way I had treated her, and I asked her to forgive me.  She replied, "Wow, thank you for saying that. Of course I forgive you.  No worries."  Well, weight lifted, my side of the street cleaned.  I felt very good.

Continuing the conversation, and knowing full well that I might be pushing things too far (when did that ever get in my way?) I eventually asked her if she'd meet me for coffee.  A little time went by, and the story in my head compelled me to follow up with, "Too soon? Probably too soon."  But she wrote back and said, "Honestly I just don't know when I will have the time.  I don't have the time for much of anything these days."  Well, I thought, at least she didn't shut it completely down.  A couple of more texts, but no progress from there.

I feel as though there might be the slimmest of possibilities that Leah would be open to seeing me again.  Perhaps not regularly, but occasionally.  Even grad students need a little relaxation -- I'm pretty sure she doesn't want for male attention -- and I'd be happy to oblige her.

More to be revealed...