Thursday, December 31, 2015

2015 is Ending Perfectly!

Last night, after I had closed the biggest and most lucrative single deal of my career, Leah sent me a picture of her in nothing but a pair of black panties, captioned with "A preview of what's to come in 2016."  To say that I loved the gesture is an understatement. I just melted.

I had forgotten how gorgeous she is without her clothes on.  And in four days I'll experience her first hand.

She seems to have gone all in, so I'm riding that wave all the way to the beach!

Happy New Year Everyone!

Tuesday, December 29, 2015

Leah Date Cancellation #2

Leah had been out of town over the Christmas weekend,  came back last night. I sent her a text this morning to confirm our date today,  and about an hour or so later she responded that she couldn't make it.  She didn't explain why.  I'm giving her the benefit of the doubt as she has cancelled before with an explanation, and she's not the type to ditch and be tight-lipped about it.

UPDATE: she texted and asked to reschedule next week,  saying that something came up with a parent that got in her way. Again,  benefit of the doubt for now.

Still,  that gives her one more chance. Another cancellation and I walk.

Natalie, meanwhile, can't see me till the week of 1/11.

If Leah falls out, I'm pretty sure I'll start looking again.

Monday, December 28, 2015

Sugar Sweetens...but We Can't Live On It

I was asked if I would ever seriously consider leaving my wife for one of my sugar babies. I posted a few days back that I wouldn't.  A reader posted a follow up comment on that post, as follows:
My SD is divorcing his wife. So, we're at a weird point in the arrangement. This may sound odd, but I wish he wanted to stay married. I really encouraged him to work things out. I guess I feel like we can't have a "real" relationship. It's like what you said about switching your mindset. 
As I've written before, there are two types of relationships: short-term and long-term.  Short-term relationships are characterized by "recreation," which primarily means sex, but also other types of fun.  As soon as a problem emerges in the relationship that poses a serious threat to the fun, one of the partners -- more than likely the man -- must end the relationship without hesitation and with honor. By "with honor" I mean that a man must resist the urge to shame, hurt, or otherwise cause damage to the woman when he ends the relationship.  I can't speak for what the woman ought to do when ending a short term relationship, but here is some sage insight that could actually pertain to both men and women during the break-up of a short-term relationship.  I have been guilty of not handling break-ups well whether I was the giver or receiver of the bad news (see Jade, Leah, and C), but I have also been in some cases pretty good about it (see CC, Wanda, Sam, and Staci).  In any case, it's best to use honest communication and not add drama to the situation.  I find it better to place the blame on me rather than the other during a break-up (the old, "It's not you, it's me" cliche).  Sex in a short-term relationship is usually centered on getting something: getting laid, filling a gap in one's life, getting a little temporary closeness.  For me, the sugar bowl has been all about getting laid, and I have unashamedly admitted that I have used my expert bullshit skills to get laid, and I freely admit that anything goes to keep the sex going.

Long-term relationships are a whole different world.  They focus on emotional/spiritual bonding, family creation, and shared values that can last for the rest of one's life.  Sex in a long-term relationship is also totally different than sex in a short-term relationship: they can (and should) both be fun and adventurous and daring, but the primary goal in long-term sex is to express love for one another, to be giving, and to nurture the relationship.

I mentioned in my prior post that it's impossible to turn one relationship into the other.  The reason for this is simple: when one's mindset is on short-term goals, then shifting to the long-term goals of a life-long relationship necessitates a complete letting go of the short-term goals.  Essentially, one must end the short-term relationship first, take some time off to become ready for a long-term relationship, and enter it in a different way.  In my adult life, I know of only one man who has done this successfully.  He met his current (third) wife at a cell-phone store, followed her to the parking lot, took her home and fucked the living daylights out of her over the next three days.  He was much older, and had four grown children.  She was just getting started in her life.  He thought he was just getting into a sport-fucking fling, but as they started to communicate he saw how deeply they were connecting.  He realized that this was a long-term relationship and he had to back up and shift his mind-set.  He didn't know if he was available for a long-term, and he told her this.  As luck would have it, she wasn't sure either, but both expressed a willingness to try to see how things could go. This effectively ended the short-term relationship so they could explore other options.  They both shifted their thinking, approached each other differently, and they've now been married ten years. My main point here is that when a person sees another as a short-term "get," it's impossible to then see them as a long-term "give" unless one is willing to give up getting.

These points lead me to my reader's statement above.  Her Sugar Daddy is divorcing his wife.  It's not yet clear whether he initiated or his wife did.  It's also unclear if he's angling for his sugar relationship to move into a new space.  What is clear, however, is that my reader does not want a long term relationship with her SD.  I think she understands that there's no changing course here.  After a year together with a very specific set of rules, it's not going to work to change the rules and start looking at each other like potential life partners.

Leah had this situation happen to her.  A sugar daddy she was dating wanted to date her for real, but he was married.  She said she only dated single men.  The guy proceeded to leave his wife (they had no kids) and a year later, he contacted her.  They dated for a time (I'll probably find out how long when I see her) but now they're not together.  This could very well be another example of how one can't convert a short term into a long term.  Not without the shift in mindset.  Given that Leah was headed into grad school, it may reveal that Leah wasn't ready for the shift.  I hope to hear more about it when I see her.

Thursday, December 24, 2015

Today...Natalie -- Live-Blogging

8:00 am
In about two hours I will be slipping through Natalie's unlocked door, quietly undressing in the living room, and then sneaking into her bed while she "sleeps" for our first time together.  It's something I've done both with C and Leah in the past, and it never ceases to be totally hot.

I've asked Natalie not to wear makeup or any special clothing other than what she normally wears to bed.  Last night, however, she revealed that she has an early yoga class, so I know she'll be freshly showered.  Sort of not what I wanted, but I'll live with it!

9:10 am
Starting to get the stomach jitters, as I always do before a first date.  Money's handled, stuck snugly in a cute Christmas card; last minute work details completed; about to check traffic to make sure I get there on time or a little bit early. Taking some deep breaths to settle down, but I'll probably ratchet back up during my drive across town to her apartment.  Looking at the water bottle on my desk and wondering if I should have a drink, deciding no, as I'll just have to pee when I get there.

9:25 am
On my way...

9:50 am
Got the address wrong, so I'm still five minutes away.  Derp!

9:55 am
Natalie texted me to park in the driveway of her apartment, as her landlord is out of town for the holidays.

9:58 am
Arrived and parked.  Grabbed what I needed from the car and headed to her place.  Door was unlocked.  Once inside, I went to the living room to undress.  Door to her bedroom was closed, with washing machine going near the kitchen.  I slipped out of my clothes, down to my underwear, then place the envelope with her allowance on top of her laptop in the kitchen.  Grabbed a couple of condoms, the lube, and my phone.  Opened the door to her bedroom.

10:02 am
Natalie is snuggled up under the covers in her dim bedroom, sparsely furnished but for the bed, a small vanity table, a couple of mirrors, a cheap floor lamp, and two side tables on either side of the bed.  I placed the condoms and stuff on one table just as she rolled over to face me.  She gave me a big smile and lifted up the covers to let me in.  She was wearing no makeup, just a little white t-shirt and a pair of boxer briefs.  Cute!

10:03 am
Kissing, kissing and more kissing.  No pretense about what both of us want.  We want to fuck something fierce.  I take her hand and place it on my dick, over my underwear, which prompts an exclamation about my size.  Usually I'm sensitive about that, but for some reason, I let it roll off me today.  Call it being at peace with my body.  I put her hand in my underwear and the exclamations continue, some shock, some pleasant surprise.  More kissing.  Always there was lots of kissing and tongue action.

I slip her out of her top, following with my t-shirt.  Her body feels warm and soft, and I apologize about my cold hands and toes.

Finally both of us naked, and she reaches for the lube, and starts to stroke me and lube me up, presumably for the condom.  "I want to practice safe sex," she says, "is that ok?"  "Of course," I say, "but I kinda want to lick your pussy first, if THAT'S ok."

I haven't gone down on a woman who hadn't shaved her pussy in ages.  Even DW gets waxed around her labia and keeps the hair nicely trimmed.  Natalie is trimmed into a nice shape, but she's hairy all the way down the sides of her pussy.  No matter, but it feels different having to pause occasionally to remove hair from my mouth.  She's a very vocal lover, lots of moaning.  But no telltale signs of climax show up.

I do not get a blow job longer than 10 seconds!  This was a major strike against her.  And she had pretty decent skills.  I didn't want to push it, so I let it pass because I'm having a great time.  On goes the condom and I enter her missionary.  She reaches to the bedside table and produces a small black vibrator, no bigger than the palm of her hand.  She turns it on and places it directly on her clit while I'm inside her.  This is somewhat different, but I'm down and rolling with it.  Not every woman can cum from either oral or penetration, so I admire her for taking charge and making it happen.

Her climax comes just about three minutes later, and it's a doozy!  I am on my knees between her legs, her knees are up on either side of her chest, and I'm holding her butt in my hands, getting very deep inside her.  The orgasm comes like a huge wave crashing on the beach, classic!  "Oh my god, I need to come so badly!" she cries.  As we continue, she remains vocal and passionate, but I could tell she was a little woozy from her orgasm.  I slow things down for a few minutes before going again. When I draw her on top of me, she reaches again for the vibrator.  You go, baby! I think.  She straddles me after a few minutes, sitting on her haunches, flat footed on the bed, to get the vibrator in the right spot.  I reach under her and hold her up and she comes again, falling on top of me. "Happiness is coming twice," I smile, which gets her to laugh again.  I pull her close, putting my arms around her, and unload inside her after about 10 more minutes.  I am literally out of breath (man I'm out of shape!) and dizzy, but I'm so happy!

10:40 am
We talk about many things, but primarily what sticks with me is the discussion about her marriage.  I remind her that I wanted my first allowance to go toward a paralegal so she could file for divorce. She explains that she wants to pay off her credit card debt first, and that the divorce filing is a low priority for her.  "I'm thinking some time in the next year," she says.  "It's just not something I care all that much about.  I have no intention of getting back together with him.  Is that something that concerns you?"

"Well," I say, "it's always been a rule of mine not to do these arrangements with anyone who's married.  But I get from what you're saying that you're completely done with the marriage."  I then tell her that my thinking used to be "No husbands, no fiances, and no serious boyfriends.  But after my time with Leah, and doing some really deep thinking lately, I realize that I'm removing from my partner any say in how she would like to conduct her life.  In other words, if she's in a relationship and she has no issue with being non-monogamous, and wants to be with me, then who am I to stop her?  I still won't sleep with anyone in an active marriage or engagement, but if there's a single woman who wants to be with me and doesn't have a problem with non-monogamy, then I'm fine with it. I ask her, "If you meet a guy you want to be monogamous with, you'd tell me, right?"  "Of course," she replies.  "That's all I want," I say.

11:05 am
We start kissing again, I get hard and get on top of her.  I enter her without a condom, and she does not object.  She's on birth control, and I'm clean as can be, and I'm not worried.  We only go a few minutes before she announces she has to pee.  When she returns we don't resume sex, but talk some more.  Cultural stuff about her Latina culture and my Jewish culture.  Apparently she's had some really close girlfriends who were Jewish.  I tell her that I'm happy because that'll give us more to talk about, and that's become increasingly important to me.  We start to talk about sex again, and I say that I would love to tell her my fantasies while my cock is inside her. She lubes me up and we try doggie.  She gets the vibrator again and comes a third time!  Just before I'm about to cum I pull out, but I time it poorly and I don't climax.  A little frustrating.

11:45 am
We shower off together and then get dressed. She has family stuff in the afternoon, and I need to get home and do some work before Christmas.  We kiss, and hug, and I'm feeling pretty good about our first time.

12:05 pm
While on the road home I reflect on our date.  She's a fantastic girl, a real woman, nothing superficial about her.  A decent lover too -- I'd give her a seven out of 10, marks off for not going down on me. She knows her body well, so I'm not put off by the use of the vibrator when we have sex.  Great body, too!  But something is nagging at me, and I can't yet put my finger on it.

12:30 pm
Just before I get home it hits me: Natalie can only get together after work hours.  I've always maintained, for seven and a half years, a commitment to not allowing my sugar activity get in the way of family time.  Yes, the occasional late night work session isn't all that bad, and I've already been prepping DW by actually working late a few times here and there, but I sort of don't like having to do that.  I like sitting down to dinner with the family every night and putting the kids to bed as often as I can.  So this is something that I think might be an obstacle to a future with her.

Leah and I have our reunion date early next week, during the late afternoon, getting me home by dinner.  I'm cautiously optimistic at this point; either girl would be great.

Tuesday, December 22, 2015

A Reader's Question

A loyal and lovely reader writes:
Do you think if you found a meaningful SB relationship that you would leave your wife for the SB? I know you had fantasies of that in the past, but do you think you'd ever actually do that?? 
Back in June 2012, as I contemplated the end of my relationship with C, I had brief thoughts about this.  I also brought it up again at our next date, when I actually asked to marry me in 10 years. Finally, five months post-C, I thought about what I really wanted.  I wrote:
Over the past several days, I have formed what I think is a pretty clear picture of what I want from the "arrangement."  But before going there, I also had to ask myself what I wanted in my life.  And, if I'm being brutally honest, I had to admit that I wanted something more emotionally meaningful than what DW was offering me.  I had to admit that her emotionally rigidity, and her sexual frigidity, to say nothing of my demonstrated anger and resentment toward her about these things, had ruined any chance I had of a life-long commitment with her.  Did I see myself with her in five or ten years?  No.  I finally had to admit that I wanted out of my marriage.
This thought eventually got me thinking about long-term possibilities with Jade.  A lot good that did me, huh?

A lot has changed in nearly three years.  First of all, the thoughts I'd had about making a future with C were clearly momentary fantasies.  There was no way, with her relationship with her then-boyfriend-now-fiance as solid as it could be, that any type of future was even possible.  Secondly, our insurmountable age difference, nearly 25 years, was why I suggested she find me in 10 years if she found herself single again.  At that point I'd have no issue with the age difference.

Finally, the "what I want" excerpt above sort of went away earlier this year or late last year.  Despite the fact that DW and I have been sexless in our marriage for over a year now, I have no desire not to be married to her for the rest of my life.  In fact, I told her the other day that, no matter how tense things may get between us, no matter how much I might disagree with her on any given subject, there hasn't been a day in all the time we've been together that I haven't been head over heels in love with her, and trusted her completely.  I am at peace with exactly how things are right now, and will be at peace with anything that develops in our relationship, including -- as I've said from very early on in this blog -- the end of our marriage if I get caught.

I don't believe one can turn a short-term relationship into a long-term one without a complete shift in mindset.  And my mind rarely considers anything beyond the short-term, recreational aspects of being in an arrangement.

The answer, therefore, is no, I don't think I'd every voluntarily leave DW for a Sugar Baby.


Sunday, December 20, 2015

Leah Sugar Date Cancellation #1

I was on Facebook Friday night when I read that Leah's mom had a cold.  Leah, sweet thing that she is, posted a note to the comment: "Me too, momma. Me too."  Immediately I texted her: "Are you getting sick?"  The reply was not what I wanted to hear: "Yeah, but I should be better soon. However, there's something else: I got my period today too."

So Leah had to cancel our date for Monday afternoon.  She graciously apologized, and of course I accepted.  It took us a little while to reschedule.  With the holidays and my work schedule, and the fact that she's going to visit her sibling out of state for Christmas, we had to push our date back eight more days.  I usually have a mandatory commitment on Tuesday nights, but with the holidays the commitment isn't mandatory.  

"I still want to see you Monday though," I texted.  "You mean no hotel?"  "Yeah," I said. "No hotel, Meet me for an hour of so.  I'll give you the allowance as a raincheck for the next date."  I wanted to show her that I trusted her and that I meant what I said when I told her that I wanted her.

While Natalie and I initially postponed our date until January, she and I talked on Friday afternoon, and we rescheduled for the morning of Christmas Eve.  Since my work schedule is light this week, I am going to spend the morning with her, then come home instead of going to work.  

If all goes well, I'll have a very enjoyable eight days.

Thursday, December 17, 2015

Natalie Sugar Date Cancellation #1

Today was supposed to be "Fuck Day," when I get to spend quality time with my current Sugar Baby, Natalie.  But we both came down with colds at the same time, and we shared texts within minutes of each other to let the other know we were under the weather.  I told her that, because of the holidays and how busy I was at work, I would probably not be available again until after the New Year, but that if I suddenly found myself with time, I'd still like to see her.  This way, if Leah and I don't click next week (or if she changes her mind for the sixth time!) I might still have a slot for Natalie.  She agreed to this and said that January would probably work better for her anyway.

However, suddenly I felt better this morning.  Sheer will, I guess, because I really wanted to get together with her.  But she responded to my "Good morning, how are you feeling?" text with "I still feel like shit."  So, we're probably done for a couple of weeks.

Meanwhile, Leah finished her final exams and I checked in with her to see how she was feeling.  She confirmed yesterday that she wanted to get together next week.  Since her texts to me were at most two words, I kept it very short and sweet.  "I'll confirm again the day before" is all I wrote.  I'm so expecting her to change her mind again, that I set up Sam as a potential backup for the same day.  She was down for whatever, since we're only getting together when we both find time (and desire).

I swear this Sugar Dating shit can sometimes take up way too much of my time.

Monday, December 14, 2015

On Sugar Baby Failures (And There Are Many)

Scrolling through my Twitter feed I came across a retweet linking to an article called "Seeking Arrangement: On My Brief & Failed Attempt at Becoming a Sugar Baby." Right there in the headline was the recipe for this writer's failure.  The piece documented many more, and in my piece I'll take them on.  Essentially, if one doesn't commit to the process of being a Sugar Baby, she can't be one.

I have successfully "sugared" for nearly eight years.  During this time, I've had four arrangements that I would call "long term."  These are those that have lasted at least six months: CC, C, Jade, and Audrey.  Additionally, I have had five arrangements that I would call medium term, lasting at least two months: Dale, Wanda, Sam, Leah, and Staci.  Finally, the remainder of the nearly 40 women with whom I've had encounters have been one-time-only meetings (or two).  In nearly every case, I've learned something from them, about myself, and about women.  I wouldn't call myself an expert on women (no one is), or even dating them, but I do have a fair amount of experience on which I can draw.

The first thing I would tell this writer is that being a Sugar Baby is not something she should ever have taken unless she could see herself doing it for awhile.  I realize that some Sugar Babies get in the game thinking that they'll only do it for a short while in order to pay off a debt, or save up for a trip.  I'm sure some get what they want and then get out.  But the vast majority get in not having a clue about how to attract the Sugar Daddy who is perfect for them (not necessarily the perfect Sugar Daddy).  

She writes: 
I created a seekingarrangement.com profile, carefully crafting my image as a young writer eager to rely on the kindness of strangers. And, soon enough, the messages began pouring in. What I hadn't accounted for was all the online communication necessary to weed the weirdos from anyone with potential—I can barely manage to keep in contact with the people I love, let alone find time or motivation to talk to would-be sugar daddies. 
Again, experiences vary, but a person who can't manage to stay in contact with loved ones is going to have a tough time with sugar.  Daddies, even though we want something with no strings attached, do not wish to be bothered with babies who have no time to be responsible with their communication. When I send a text or email to a potential Sugar Baby, if I don't get a response within a couple of days, I move on.  It doesn't have to be complicated.  I spend a minute or two reading their profiles, and if I find something I like, I and highlight it and paste it into my introductory note to them.  I frequently close with this: "Just know that 'No Thank You' is a perfectly acceptable answer, and preferable than no answer at all."  With that message, I've communicated two things: one, I have plenty of options; and two, I expect a bare minimum of an answer to satisfy me.  If a woman is serious about being a Sugar Baby, she'll answer me one way or the other.

Second, she met her first potential Sugar Daddy while drunk:
"The fact that I felt willing to [meet someone while shitfaced] explicitly says I was in no condition to do so."
A young woman in New York City, bright enough to know better, meets with a total stranger while inebriated, drinks some more, then, knowing she's too drunk to be responsible, inexplicably accepts a wad of cash from him and allows him to take her to his office/apartment, where she falls asleep and spends the night. That he left her there, unmolested and with her clothes still on, speaks to the fact that he was probably a good enough guy to be a SD, but not smart enough to realize that she was in no condition to make sound decisions.  He made the right choices in the end, but I probably would have walked away and not offered to let her crash at my office.  Her stupidity here is clearly obvious.  I have had experiences with Sugar Babies where I fucked them the first time we met, but I was never drunk off my ass to the point where I didn't have my wits fully about me.

Another mistake:
He'd had fun hanging out and wanted to see me again if I was into it. But I was too embarrassed by the whole thing by this point—the drunkenness, the passing out, the very fact of meeting up with a sugar daddy. It seemed somehow, suddenly, sordid. I vowed not to see [the guy] or use the site again.
Conviction, however, has never been my strong point. 
She is clearly not the SB type.  A person can't play this game being wishy-washy or weak willed. Men who do so without having clearly defined terms and goals are going to get taken advantage of and lose a lot more of their money than they'd intended.  Women can have it far worse (see Cosby, Bill).

Finally, the biggest mistake of all:
When I tried to politely excuse myself from the situation, I was met with more pawing and a side of guilt trip. I am probably going to regret admitting this, but I gave him head because it just seemed like the easiest and quickest way out of the situation. 
Wait, what?  Giving a guy head rather than standing up for oneself and getting the fuck outta dodge is the easier route to take?  The writer just put the money ahead of her safety and her dignity.  It's no wonder she was done with Sugar after that.

Her conclusion:
I feel like I should come up with some moral to this story, but there really is none. As far as takeaways: 1) I suck at being a sugar baby and 2) sugar daddies come in all stripes. Maybe this is my moral: That there is no one type of woman or man using this site, and its silly to make blanket conclusions about them. And maybe that you shouldn't get wasted before meeting a strange man for drinks? But, meh, I can't even say that with much conviction, because it worked out just fine for me. Maybe my moral is just that there doesn't need to be a serious moral served up with stories like this. Sometimes we randomly decide to meet strangers for strange sexual arrangements, and it's really just not that big of a deal.
She's right about her takeaways. She does suck at being a SB.  But she didn't have to be.  Had she thought things out she probably would have had a much better and more successful experience. And had a lot more than $500 to show for it.

Pre-Natalie Jitters, and DW Lends a Hand

Sunday morning found me just as horny as ever.  I looked over at DW and knew that having sex was impossible, not after a nearly 13 month dry spell.  Still she'd been nice enough to give me a hand job a few months back, so I decided to see if she was game.  After some really nice holding each other, I took her hand and directed it down to my waiting hard-on.  "Really?" she groaned. "Okaaaaaay." While she started off kind of half-hearted, I asked for her to do her special two-handed job, which never fails to get me off quickly.  Sure enough, I came in about three minutes.  That's even faster than I can do myself on most days.

While the day went on with a fair amount of stress due to some family-oriented stuff, I was glad to be back home and going through our normal bedtime routines with the kids, who were a little more cooperative than usual.

On Sunday nights after the kids are in bed, I usually confer with DW over some domestic chore to see what her week looks like, so I can plan my sugar activities accordingly (not that she has any idea).  When she told me that she had scheduled an appointment for the night I had planned to be with Natalie, I had a mild panic moment.  I'd already canceled on once, which caused to wonder if an arrangement with me would be too inconvenient. We'd planned this date before Thanksgiving; I imagined that she'd figured I'd had my calendar in order, so me wanting to make a change might not be well-received.  This was the story in my head, especially since not a couple of hours earlier I had texted her to tell her how excited I was to be seeing her in four days.

Right after DW told me about her appointment, I texted Natalie to let her know I needed to make a change.  With Leah's date coming just a few days later, I decided to see if I could move up the Natalie date to one day earlier.

However, all night went by, and most of the next morning, before she responded.  I got more anxious, thinking she'd started having second thoughts again.  But, about an hour ago, she agreed to meet me in two days rather than three.  Success.  She is as excited now as before.

My date with Leah is still scheduled for a week away, and I'm fairly certain it will happen.  If she changes her mind again, however (those of you who are, like me, keeping count, it would be her sixth mind change since I resumed contact with her), at least I won't be surprised.

Wednesday, December 9, 2015

Guilt and Sex

Last night I had a couple of very interesting experiences.  First, I got home from work around 5:45, and would have about an hour at home before I had to leave for dinner with my buddy Luke.  One of my kids was at sports practice, and the other at a holiday party with classmates.  I would be gone before both of them returned home.  I was alone with DW.  I had prepared her that Luke and I would probably shut the restaurant down and hang out for awhile afterward, and that I'd be home around 10:30.  This would give me time to hang with Luke, and then drive the 30 minutes to Natalie's apartment for our make-out session.  In my mind, this was all going to work out perfectly.

But something unexpected happened to me.  In hanging out with DW, who was busy making the kids' lunches for the next day and sneaking bites of mint chocolate chip ice cream, I realized that I was having a good time with her.  It's not unusual for me to feel that way, since I actually do enjoy her company and love her to pieces.  I got to make her laugh, actually, and see her beautiful smile.  Her smile truly lights up her face, and it hit me that I don't get to see it enough these days.  Lots of stress, around the kids' schools and their very busy extracurricular activities, which has her driving all over town a few days a week.  She also has her own business, and unfortunately that stuff takes a back seat while she's being Mom. 

I found myself looking at the clock a lot, checking traffic conditions to make sure I would arrive at the restaurant on time (it was about half an hour away).  Anything, to avoid the growing sense of guilt I was feeling at leaving my house at night, eventually to end up spending time with another woman.  

Finally, with about five minutes left before I needed to leave, I couldn't take it anymore.  "I'm leaving," I told DW, "I'll probably get there a little early, but I don't want to be late.  If Luke is early, maybe I'll be home a little sooner."  I kissed her goodbye and headed out the door.  Walking to my car, it dawned on me that this guilt, in a way, justified why I do the sugar thing in secret.  

When DW first suggested, nearly eight years ago, that I find a girlfriend for sex, she'd insisted on some rules which I'd found ridiculous.  One of them was that I could not go on my dates until the kids were asleep.  That was when they were much younger.  Now one was a teenager and the other a pre-teen. They don't usually go to sleep till around 10, so waiting until then to shower up and leave for a date would be crazy.  But back then, I thought it was nuts too, because once I walk in my house to be with my family, I don't want to leave them.  I love them and enjoy my time with them.  So, thinking this through, it made no sense for me to come home, sit down to a family dinner, help the kids with homework and DW with cleaning up, oversee the kids' bedtime rituals, read stories, then turn out the lights, before showering up and driving wherever for my date, only to come home three hours later and then climb into bed with my wife, who knew I had just been fucking someone else.  A while ago, I saw my rejection of that condition as a protection for her; her feelings could be hurt knowing what I was doing.  But in that moment walking to my car, I also realized that the condition needed to be rejected to protect me as well.  I hadn't given that much thought to how I would feel walking out the door from my family home to a date with another woman.  And it justified for me why, if my sugar activities were ever brought out into the open (as I hope they will someday be), I will insist that DW not know when I'm on a date.  I'll just "work late" a few times a month.  She might know that the date is going on, but she is not seeing me leave to go get laid, and I'm not leaving her to do that.  If I do all that before I get home after work, it all makes much more sense from an emotional point of view.

Dinner with Luke was a blast.  He's a man's man, but because of his work, he's also very in tune with feelings and family.  He has been totally supportive of my sugar activities, but did admonish me when I told him about C and how I'd fallen in love with her.  We drank a couple of glasses of red wine, had some delicious Italian food, and nearly $100 later, I was out the door, on my way to see Natalie.  I showed Luke some pictures of her before leaving, and he was blown away.  Yes, I told him, I am very happy with this one.

I hit the road just before 8:45, sending Natalie a text that I'd be up a little early if that was OK with her.  She said it would be fine.  It took me just under half an hour to get to her place, a guest house apartment behind a main house, just off a main drag in a predominantly Latino part of town.  Parking was up the street, about a two minute walk from her house.  I had snatched a bottle of Cabernet from our liquor cabinet as I didn't want to get there empty-handed (DW would never notice since she doesn't drink).  She greeted me at her door wearing a grey, form-fitting T-shirt, a pair of purple sweats, and pink socks.  I got a nice kiss at the door before she gave me the tour of her small apartment.  It would be fine for just one person, I thought, but she had lived here with her husband before they separated, and I thought it could have contributed to the demise of the marriage being so confined.  I really like my big house!  

After the tour we settled into the couch in her living room and chatted for just a couple of minutes before we started kissing.  This was not going to progress to sex -- I did not have allowance money or condoms -- so all we would do is kiss and touch each other.  I did, however, learn a few things. She told me that she doesn't shave her pussy, and prefers going all natural (though trimmed and not too bushy).  She has a fantastic body, and the professional pictures she'd sent to me were a present she'd given to herself because she was "in the best shape of [her] life."  I would say she was in decent shape but got the feeling that she'd lost quite a few pounds.  No complaints, but her body was only slightly better than Rachel's.  I didn't get her naked, but I was able to get under her clothes with my hands and feel around a bit.  With each step I took I asked her for consent, and she gave it; had to be safe, no matter what. She felt my cock outside of my jeans and remarked, "you're pretty girthy!"  

After about 30 minutes of this, I had her on top of me and we were grinding into each other.  We both really wanted to have sex, but we held off.  I said, "I'm wondering if we can move somewhere more comfortable."  "You mean you want to go to my bedroom?" she asked.  "If it's OK with you." "Yes," she said.

On the bed, we continued the same thing we had been doing, but a little more intensely.  While lying on top of her between her legs, I said playfully, "I want to give you what you want."  I rose to my knees, then lowered my face to her pussy and gave it a kiss over her sweats. She cracked up.  "At least I got to kiss you between your legs," I said.

I looked at my watch and I had five minutes before I had to leave, so we started slowing things down. I thought I might have leaked a little in my pants, I was so turned on.  As I got off the bed, I thanked her for letting me come over, and asked if we'd built up enough anticipation to carry us the next 10 days until we met for sex.  "Yes," she said, "but if I need more kissing, I'll call you."  She thanked me for coming over.

I left her apartment and strolled down her street, with a full and throbbing erection.  My shirt untucked hid it from view, but I knew it was there.  My erection did not subside until I got home. On time!  Once home, I found DW awake, having just gotten the kids to bed.  I washed up and excused myself to prepare for the next day, which actually involved jury duty.  But that was a ruse for me to jack off, which took all of 10 minutes.  The next morning, Natalie texted me that it only took her five minutes to come once I left.  

I think we'll have a great time next week.  Since I'll be neck deep in work and with the holidays coming up, I'll probably convince Natalie to hold off on another date until after the new year.  That way I'll have time to see how things feel with Leah before making a final decision.


Monday, December 7, 2015

A Sugar Daddy's Very Busy Week

Things with both Natalie and Leah are definitely heating up.  I have been pretty much torturing myself trying to decide between these two extraordinary women.  Both of them have fantastic qualities, with Natalie (at this point at least) showing me zero negatives right now.  Leah's negatives have me a bit perplexed, and readers have been messaging me not to go with her.  Let me try to explain why, despite her past transgressions, I am still seriously considering her.

First, and not necessarily most importantly, Leah is about the most beautiful woman I've ever seen. You can read about it in my post of our first encounter.  Second, I consider her to be an intellectual equal. Well-read, wise, curious about the world, and passionate, she matches me step for step.  Third, even though I've used it as an obstacle in the past, our connection through her mom is also a huge pathway to a deeper connection. Even though these relationships are short-term and recreational, there's always a desire in me to be as intimate as I can with my partner.  I know that Leah and I can get there.  I cut it short last time, ended it by surprise, then flipped out on her when she revealed she had a boyfriend.  She was obviously telling me the truth when she said the relationship with her boyfriend wasn't that serious.  They are no longer together.  But my actions made it very difficult for her to trust me going forward. 

Finally, with Leah in grad school and having very little time for regular, reliable meetings, it makes it difficult for me to choose her.  Further, she seems to be seeing our potential encounters, and the seemingly flippant way she changes her mind, as not having consequences for either of us.  But she doesn't know one crucial thing about me: despite the casual nature of sugar, despite the fact that these are finite relationships, for me they are not frivolous or meaningless.  As you have been reading, DW and I haven't had sex in over a year now, and there is no sign that sex is coming back into our marriage.  I have made my peace with that and fully embrace that our marriage is moving into a different territory.  But to reconcile that with the reality that I'm not yet done having sex, I turn to sugar.  These relationships are my sole source for sexual contact and are therefore very important to me.

During the past five days, Leah and I have been exchanging quite a few texts since she told me that now she really wants to see me (despite telling me last month that she found it too risky).  I asked her when her school let out for the holidays.  When she gave me the date, I said I wanted to see her that day or the day after.  She took a day to respond, but she gave me the dates.  She said she wanted to get together during her break.  It took another three days for her to tell me that she wanted to see me the day after school ended, but by that time I'd already made plans to see Natalie on that day. So I had to try to push it to the next week.  I gave her two available days.  Her answer was "Yes."  Confused, I asked, "Which day? Or -- both?"  "Both," she wrote.  "C'mon, really?" I replied.  She said she wanted to see me both days.  I was going to see Natalie so having three dates in a week was just not going to work for me.  "I don't think I can swing double the allowance," I wrote, "holidays."  So we agreed on one day, and we agreed on terms (which were less than our original amount last year, but I'm not saying anything).  

So Leah and I are seeing each other in two weeks.  I have no idea what will happen after that.

Now, Natalie is so far doing everything right.  Over the past weekend we exchanged quite a few texts.  I have begun each day with a "Good morning," followed by how many days until we see each other next. "I love the countdown!" she wrote me last night.

"How else to keep us engaged and building anticipation?  Open to your ideas," I replied.

"Kiss me again."

"I'd love to. How to make time?"  I asked her when her Monday evening was over, and she said 8 pm.

"I'm having dinner till about 9, about half an hour away.  Should I stop on by and we can make out?"

"Yes please."

She sent me her address and two unbelievably sexy pictures she'd had taken with a professional photographer.  "Wow," I wrote, "that's a good way to build anticipation."

"I had some pictures taken to capture this chapter of my life," she replied.  Naked in one, bikini in the other, both showing off her ridiculous figure.

I decided to be a little more playful. "Umm, do you trust yourself tomorrow? I mean, I'm a pretty good kisser."

"I want you to kiss me between my legs."

"I'm very good at that.  Can you stop at just kissing?"

We both fell asleep after that, but this morning at 6 am:

"Why do we need to stop at just kissing, might I ask?"

Well, now I saw that she might have been thinking I'd be available for an allowance-type date.  All I really wanted was to show up at her place and make out.  "I can only stay for half an hour and I wouldn't have the allowance on me.  Wouldn't want to take advantage.  Did I unwittingly create an expectation?"

"OK," she wrote, "come make out with me."

"Great.  That'll be fun.  Plus you get to see me leave with a boner."

"You're going to leave ME with a lady boner."

"At least you get to take care of it right after I leave.  I'll have a long drive home."

So, tonight, after my dinner with my buddy, I'll be driving half an hour to spend half an hour with Natalie, then driving half an hour to get home!  I am going to do my best to keep it kissing only, no getting naked.  My mind is racing with the possibilities.  Think I'll succeed?




Thursday, December 3, 2015

Natalie Needs Me.

All day I eagerly anticipated meeting Natalie.  Sat in my office, trying and failing to busy myself with work to distract me from how excited I was.  After last week's conversation, I just had a feeling that this woman was going to impress me.

With 45 minutes to get across town, my Waze told me it would only take 30 to get to the tavern where we agreed to meet, midway between our two offices.  I texted Natalie on the way: "Let me know how late you're going to be, haha."  It was a Thursday, usually a heavy traffic day, and I wanted to make a light comment to put her at ease just in case she found herself behind schedule.  "I will not be late," came her reply.  Well, I thought, that's a woman who wants to make a good impression!

I made it with 10 minutes to spare at the valet parking stand.  Got out and took my keys, then was called back to the car because I'd left my cell phone. Can you say distracted?

I took a seat on a stool at a long common table, and checked my phone for some stuff.  Ten minutes later came a text: "I'm sitting at the bar, red top, black skirt."  The bar was right behind me, so I guess we missed each other.  I texted back, "Turn around."  She reached for her phone and read the text, then I tapped her on her bare shoulder.  We laughed and hugged.

Natalie is seriously gorgeous.  Dark, straight hair to her shoulders, deep brown eyes, big wide smile with perfectly straight teeth.  Natalie was dressed for work and looked awesome.  I felt a little schlubby in my Ralph Lauren dress shirt and khakis, to be honest; I'd thought about wearing a suit, but decided against it because I was working alone all day.  She didn't seem to care or even notice.

We took a seat at an empty table in the bar and were served right away.  Great food at this joint; have to remember to come back.

We had already come to terms on the allowance, so we talked about where we grew up, went to college, etc.  Natalie is Latina and grew up in a middle class family with four other siblings.  At 14 she was awarded a full scholarship to a very exclusive boarding school about 100 miles away and graduated with honors.  She attended Northwestern, but left after a year because she hated the cold. Transferring to a very small liberal arts school for women in southern California, she finished her degree.  While there she came to the realization that she had no attraction for boys her own age, but found older men a huge turn on (yes I love that about her!).

After college, Natalie worked briefly and then met a slightly older man who would eventually become her husband.  Yes, readers, Natalie is married.  However, she is separated and headed for divorce, and there are no children.  At first my heart sunk, but during the course of the conversation I got a very clear indication that there was no chance of reconciliation and that she had totally moved on.  I still have a little reticence going on, which I'll explain soon.

During her marriage, she left her job and went to graduate school, and had thoughts about becoming an academic, but she decided that the life was not to her liking.  She took jobs in hospitality management and now corporate training, so she's quite ambitious.

Prior to the separation from her husband -- over his substance abuse issues -- she also had a brief affair with a co-worker who was 15 years older than her.  He was in a long-term relationship with a woman but not married, and the affair was torrid, but he ended it because he decided to patch things up with his woman.  She then kicked her husband out of their apartment and decided she was done dealing with his drama.  She got on the sugar website and immediately started seeing a very successful doctor, who unfortunately just didn't have enough time for her.  As she explained it, "I was in need of cash, and sex, and he wasn't available, so that had to end."

Natalie's priorities are very much to my liking.  She said her biggest priority was a regular sexual outlet without the need for a commitment, then money to pay off bills that she incurred refurnishing her apartment.  I'm telling you: she is nearly perfect in every way.  My reticence is around the fact that she hasn't yet filed for divorce.  They separated only three months ago, and my concern is that he'll come knocking on the door of her apartment one night, drunk off his ass, while I'm fucking her, and I just don't need that drama.  Since there is really nothing asset-wise to divide up between them, so I told her I wanted my first allowance to go toward hiring a paralegal to file the paperwork for her. She said she'd take me up on that offer.

We then started talking about sex.  We are completely on the same page there, so far.  She has no boundaries and can't wait to begin exploring what she can do with a partner who is fully present. That would be me!  I told her that there really wasn't much I didn't love to do in bed, she just looked at me and I could see the wheels turning in her head. Yes, she was mine now.

I paid the check -- $110 for four glasses of wine and three share plates, yikes! --  and we took our valet tickets outside.  Once standing in front of the tavern, she leaned into me and we started kissing right there on the sidewalk.  I hid my wedding ring between us so that onlookers wouldn't notice this old man sucking face with this gorgeous girl.  We'd stop kissing for a few seconds, then she'd lean into me and kiss me again.  I know we were both thinking about throwing our evening plans aside and fucking each other, but we managed to keep it sane.  My lips are still kind of buzzing from that encounter. She drove off in her car and I know now that we're both thinking about the next time we're together.

Goodbye to Rachel and forget Leah.  Natalie is the one.  I haven't felt this excited about a new arrangement since Jade, nearly three years ago.  I sense long-term arrangement and real connection here.  More to be revealed...

Wednesday, December 2, 2015

Am I Fickle, or Just a Lucky Dude?

In response to my last post, where I wondered if one of my readers was rooting for Leah, Rachel, or Natalie, a different reader wrote:
I think I pull for the underdog. So, I want you to choose Rachel. Poor girl. You were so crazy about her after your last meeting. I really don't like how fickle SDs are.  
I definitely understand the sentiment.  I was pretty happy with Rachel after our first encounter. Here's what I actually wrote:
It was a great first time together, and I'm so looking forward to another date with her.  ... I'm very happy with Rachel; good woman. 
But I think it needs to be said that Sugar Daddies like me have it very easy out there.  I was chatting with an SB friend the other day that when I do my searches I get over 1,500 hits in my city alone.  I can narrow that down to about fifty women who are actually interested in me and want to date me. That's fifty to one!  When the odds are so stacked in my favor, who can blame me for sampling as much of the candy in the shop as I can handle?

Another reader wrote:
It's almost like you're never satisfied...may I ask what you look for in a SB? I guess I'm curious as to why you would start up something with one SB and still look for others and hook up with other SB's. Give things time with one to grow and see how it goes before ending it and seeking another so quickly. 
I am not fickle, and it's not that I'm never satisfied; I am pragmatic.  With such lopsided odds, what I look for is the absolute best Sugar Baby that my investment can attract.   That means the nicest, most intelligent, most beautiful, and most sexual woman I can find, one who really likes and accepts me, one with whom I have a connection, or at least a spark of potential.  Rachel is a great woman: sweet, intelligent, earthy, and very good in bed. I would say that we had a pretty great overall connection. However, she is not without some definite negatives for me: her huge tats, and she's somewhat out of shape.  I would say that her pictures flattered her greatly and she didn't quite live up to them.  In a way, I see that as kind of a deception on Rachel's part at worst; at best, it's simply an impediment to a true connection.

Given the situation with Natalie, who had at that point been somewhat logistically difficult, I was definitely willing to settle.  And Natalie had always been my first choice.  I prefer brunettes over blondes.  If she is as attractive in person as she is in her pictures, and should there be some actual attraction there, there is no doubt in my mind that I'm going to switch to Natalie.  I'd have to tell Rachel that I'm no longer available.  (I actually really like that line, thanks Leira!)  I'm sure Rachel will be disappointed, and if things don't work out with Natalie I guess I'll be on the search again, but is that so bad?  I usually do a new search every few months, and there are at least 50-100 new women who have signed up since the last time.  In other words, it's not a setback for me.

Besides, let's not forget that there is also Leah, who today told me that she wanted to get together after she finishes final exams.  And let's also not forget about Sam, who will at best be an occasional Sugar Baby but that's better than nothing.

Anyone who reads my blog knows that I've been capable of long-term arrangements: six months with CC, three years with C, 10 months with Jade, and 15 months with Audrey. In between these long-term arrangements, I have always had periods where I search and experiment with a few different women. Eventually I'll settle on one. I feel that I'm close to that point now.  If not, then I'll just keep looking.

One thing I definitely appreciate though: it's the feedback I get from my readers. Thank you so much for following me on my journey.  Keep coming back and telling me what you think.