Wednesday, May 27, 2015

College Returns. I'm Going to Enjoy Teaching Her.

College overcame jet lag to send me two pics today.  One of her in bed (clothed) and one of her (shapely) legs.

I asked for more, naturally, but she demurred, saying that it'd be better that she unwrap herself next week when we met.  I have to agree, at least for now, that it would be better.  But for whom?

Staci sent nude photos of herself right from the beginning, and I was not disappointed when I finally saw her in the flesh.  Perhaps College feels that giving away the goods now might mean I place less value on her as a person.  But seeing Staci naked before I fucked her in no way diminished how impressed I am with her intellect, character, and sense of humor.  I'm just a pervy dude and I like to see tits!  Why not?

Tuesday, May 26, 2015

Back to College in One Week

College comes back from a two-week trip this evening.  Given her jet lag and my schedule, we won't be able to see each other for another week.  She told me she was open to meeting once a week as opposed to every other week, but I'm going to bring an allowance as though we are meeting every other week to our first date, and then give her less the next week if she agrees to weekly.

If, as I hope, the sex with College is awesome, then I'm going to need to do some fancy footwork to keep Staci occupied till College leaves again in mid-July.  If it's not all that great then I can always tell Staci that, "Hey, my schedule looks to be lighter than I thought," and I can propose every other week in June (two dates as opposed to four with College).

In other news, thoughts of Jade and C have been coming up in the past several days. With Jade, I'm somewhat intrigued by the notion of seeing her again.  I wish I didn't have to see her with the shadow of money in play, but that, I suppose, fuels my ambivalence.

With C, all I keep thinking about is her boyfriend, and how badly I'd like to apologize to him for potentially fucking things up.  I violated my rules, twice, with C: once when I resisted ending the relationship when it became clear that she was serious about her boyfriend, and again when I decided to stay in the relationship once it became apparent that real feelings had entered the picture.  Those two decisions to stay with C precipitated all the complicated stuff that made the end of the relationship so difficult, like saying "I love you" and confronting STDs.  Had I stuck to my standards I could have avoided the heartbreak, and probably hurt her less (and it's clear to me now that I did hurt her terribly or she'd have probably found a way to stay in touch).  

These feelings about C's boyfriend came up a couple of months ago, when I got an email from Twitter suggesting I follow some up and coming chef.  Since I follow a number of chefs on Twitter, I didn't think much of the suggestion and immediately began following him.  When I clicked over to his feed, however, the first thing I saw was a clip of a "commercial" for one of his signature products -- that featured C and her boyfriend!  The chef is based in their town, and apparently C and her boyfriend have opened a restaurant that features his menu.  That's all noise, of course.  The real issue is that until now, her boyfriend has been two-dimensional, more conceptual than actual to me.  When I saw the commercial, I saw him move and heard him speak.  All of a sudden, he became a person: a person who has no idea what his woman had done.  And it hit me that I should probably make amends for what I'd done.  It's probably a dumb idea, of course.  I'd only hurt them even without intending to.  And part of me likes that idea, I have to admit.  Like so many of the other thoughts, however, I'll just let this one pass when it's had enough of me and I become bored with it.

Thursday, May 21, 2015

A Sugar Baby Who Doesn't Want to Give Up

I got a text from Jade this morning.  The subject was a pretext for something else.  She asked if I was currently in New York City, because she swore she saw me or my doppelganger there.  "I'm not there," I wrote back, "but he must've been really good looking."

"He was," she wrote.  I accused her of not remembering what I looked like anyway.  "I remember everything about you, Porter."

She asked me how I was and that she'd "made the biggest mistake" in letting me go.  I said that life gives one many do-overs, so nothing to worry about.  She said she wants to talk and meet when she gets back to town next week.

I loved that girl. She drove me crazy, but in a good way.  She lied to me repeatedly about some pretty crucial shit, but character defects like that can be worked on and improved, and trust can be rebuilt.  I know; I've done some pretty crappy lying in my life, and I've managed to rebuild trust with those to whom I've lied.

Am I considering a redux with Jade?  At this point, with Staci rocking my world and College getting ready to do so, fuck no!  Am I open to seeing her again to test the chemistry?  Fuck yes!  Is her boyfriend an issue?  Definitely, so maybe nothing will come of it.  I'm gonna let her try to convince me that she's worth going back to.

Tuesday, May 19, 2015

Married Sugar Babies

Nearly two and a half years ago, I posted my guidelines for my Sugar Babies.  I set the guidelines up according to the age range.  I have pretty much stuck with that over the years, as I find myself consistently choosing younger women between 25 and 30 years old.  However, CC was older, Space Cadet and Lola were older still, and Katie was nearly as old as DW.  The reality is that it's not necessarily the age of the woman, it's the baggage that comes along with being older.

Going back to read the earlier post, I see that the thread that runs through all the age ranges is that I want to avoid -- at nearly all costs -- women who are married or in other significant relationships, including with children.

There are several reasons why I choose to do that:

  • Women with men in their lives -- husbands, fiances, live-in boyfriends -- do not have enough freedom to be flexible enough to accommodate my needs.  I have a pretty flexible schedule, even though I can get very busy, and if it gets too hard to schedule time with a woman (see Elle) I get bored and simply move on.
  • Because I am the one financing the arrangement, I want my fantasies fulfilled.  That is to say, I want to feel like the number one man in her life.  As soon as an important man arrives, her attention is diverted away from me.  (Cue those who decry this choice as hypocritical coming from a married man who has relatively no trouble compartmentalizing his life.  Why can't the Sugar Baby do the same?  Because I don't want one who has to do that.)  
  • Women with men in their lives -- especially those whose men live in the same city as they do -- risk "collisions" between their real lives and their secret lives.  Sorry, that's too much risk for me.  I tolerated it with C because he lived at least 100 miles away, but saw the warning signs when I became more and more expendable.  I didn't tolerate it with Jade, and I smacked down Leah when she revealed she had a new man in her life.
  • Women with young children sometimes have sufficient child care arrangements -- either with the childrens' dads or with others -- that allow for dates with their Sugar Daddies.  But in all honesty, I don't like the idea that I'm subsidizing her raising her child.  Once the relationship ends, and it always does at some point, I may have directly impacted the well-being of those children.  I don't want that burden.
Today, I got a message from a married woman who wants a Sugar Daddy.  We had a very interesting text conversation this afternoon.  The husband is a deadbeat who has no ambition and no drive.  She has a kid from a previous relationship and gets no financial support, either from the kid's father or her husband, so she's got to support the kid on her own.  She keeps all her finances separate from her husband, and he contributes nothing except for rent, groceries and utilities (except that she pays more because of the kid).  Because of all of this she doesn't want to have sex with him.  And she needs money to help pay for the kid.  On top of all this, she smokes.  Could she be any less attractive to me? She's very cute judging by her pics, but I wouldn't go near a woman like her under any circumstances. She complained to me that the Sugar Daddy website produced any positive results for her.  I'm not surprised.  Way too much baggage for any potential Sugar Daddy who isn't totally hard up for sex.  

I maintain my position on married women, engaged women, co-habitating women, or moms.  They are ineligible under nearly all circumstances.

"Don't Wait for Me"

I was supposed to meet Sports today for lunch.  I'd arranged my work day around it.  But she had an unexpected schedule change and car trouble.  Here is the text exchange (edited for privacy reasons):
S: Hi. I'm having quite a trying morning thus far... And it's early, lol.  First of all, I received a message from my [appointment] this morning; [there is] some kind of an issue and [they need] to push my appointment back [during our lunch date], and I also need to be seen in her [other office location, across town].  Additionally, there's some issue with my car, so I'll be forced to Uber anywhere I want to go today.  I don't suppose you're available later in the afternoon, are you?  I'm sorry.  If it wasn't urgent that I [keep this appointment] I would reschedule.[...]  I hope you understand and don't give up on me, but of course, I know you're anxious to make a decision, so I would obviously understand if you just want to go with [another] girl.  I'd be disappointed, but would understand.
Note: none of the other girls thinks that I've decided to keep June and half of July reserved for College; they all think it's a work conflict.  Here's my response:
M: I can't go later today.  Sorry.  I'll still meet with you though.  Let me know when the planets align for you LOL.
S: OK, thanks for understanding and for your patience.  What's your schedule like the rest of this week?
M: Not good.
S: Oh, darn.  So we have to wait until next week?
M: Listen, I know it's hard to convey motive when we're only communicating by text, but the truth is I really have a very busy schedule.  I was hoping to select someone this week because I won't be available between June 1 and July 15.  Selecting someone this week would give us time to have at least one playdate before I go underground.  But, if I don't select someone this week, it just means I'll have to wait until after July 15 to select someone.  I'm willing to wait, as I'm not in a huge rush.
S: I see.  I know you said you're not in a rush, but do you genuinely want to wait until after July 15? We can wait until then for the actual first play date if need be, but I'd love to meet before then.  And then the wait/buildup would that more delightful!
M: Unfortunately, the company I work for is a startup, and we launch in [our city] on [date].  That's going to mean all hands.  I'm absolutely committed to my success with this company, and I'm not giving myself any time for play between those two dates. Depending on how things go, however, I may find myself with additional time.  I'm not going to commit to that now, however.
S: I totally understand.  So, are we waiting until after July 15 to meet then?
M: It looks that way.  I don't expect you to wait for me to be available.  Feel free to choose another.
See what I'm doing?  I'm trying to give her an out.  For some reason, though, she's not getting it.
S: I'd be disappointed if we didn't even get a chance to meet.  Would you still want to meet in July? Or would you just choose [another] girl?
M: I don't know.  You're thinking as though I wasn't interested in meeting you, but I really am. Again, since I'm not in a rush, I'm able to wait.
S: Well, it's not my preference, but if we must, and if you're willing to wait, I guess I can reciprocate. So what now, we just get in touch with each other after July 15?
M: Feel free to stay in touch if that's your desire.  I'll do the same.  Again, please don't feel you have to wait.  I know that women [seeking Sugar Daddies] typically have more pressing financial needs that make a two month wait very problematic.
That last text was more than an hour ago, and no response.  Maybe she finally got it, or maybe she got busy with whatever she was doing.  But the truth is, I'll probably not be interested in meeting her after July 15.  If all goes as I hope it will, College will blow my mind for six weeks, and then I'll go back to Staci for what I hope will be a long time.  

But anything can happen, and if there's one thing true about me in the Sugar Bowl, it's that I hedge my bets all the time.  It's the only way I can assure myself of a companion when I want one.  On the other hand, all of this could completely blow up, but that would just mean going back to the website again, and sifting through another 20-30 women. If that's the worst that can happen, I can live with it!

Friday, May 15, 2015

Staci: Chapter 1

After seeing the pictures and video that Staci sent me since the day we met, I knew that when we eventually hooked up, it would be smoking hot.  I was not wrong.

We made a date around lunchtime at her apartment, located across town from me.  Her one-bedroom place was sparsely furnished with lots of blacks and whites, and was spacious and had a nice city view.  She greeted me at the door in a short silk robe, which revealed her sexy lingerie underneath, and nothing else.

I put down my stuff, not bothering to take out the envelope because I knew deep down that she trusted me enough to not worry about the money.  We started kissing within a few minutes, and I didn't have to wait long before my dick was in her mouth.  Oh my goodness...

Given how I'm prone to superlatives, I won't waste anyone's reading time with how much better Staci was in bed than Audrey, or Leah, or Jade, or even (dare I say it?) C.  She left them all in the dust, as though she studied male sexuality and knew exactly what I wanted at each moment.  She waited until she was grinding herself on my throbbing dick before she sprung on me that she was on birth control and that she was OK with going bareback.  I didn't even hesitate; I knew this girl would not have volunteered to have bareback sex if she a) didn't trust me, and b) was totally clean.  It just wasn't in her to be deceptive like that.  I simply saw how much she enjoyed being with me.  She had multiple orgasms, and I quietly acknowledged how grateful I was to have masturbated four hours earlier, which allowed me to last a long time.

Staci was not a clitoral stimulation type of woman.  She liked to be penetrated.  She told me she never has orgasms through oral, and when she rode me, she didn't rock her hips forward and backward to generate friction on her clit.  She squatted over me and rode me up and down.  Again, she knew exactly, without asking, what I liked.

Afterward, we spent a good hour or so talking.  We traded stories about how we were raised, our marriages, our work, and our passions.  A very well read woman with a dangerous body and unbelievable bedroom skills!  I was/am in heaven!

We had sex one more time before I left.  The envelope was on her couch, and we never talked about it again.  Given my work schedule and the fact that I'm going to be with College through June and into July, this will be our only time together until then, unless College and I don't click in bed (which I highly doubt).

If things with College feel right, I'm going to propose that we get together weekly, for a lower allowance amount, rather than every other week.  This will put a few extra hundred in her pocket, and give us more time together before she leaves again.  We're already talking about getting together while she's back in town for the winter holidays.

More soon!

Tuesday, May 12, 2015

This Sugar Daddy Will Get His Sugar

Since I met her yesterday, Staci has sent me about a dozen pics of her in different states of undress.  I will not be sharing them, as I have learned my all-too-painful lesson about discretion.  I won't know for sure until I see her live in the flesh in the buff, but it looks very much like she has a flawless body. Her breasts are natural, perfect b-cups, with perfect nipples that just make me drool.  Her bottom is similarly perfect, and even her pussy is flawless.  I figured this out by watching the sizzling one-minute video she sent of herself masturbating with her perfectly-manicured hands.  I'm laughing out loud as I type this.  It's almost too good to be true.

Staci and I have a date tomorrow late morning, so this Sugar Daddy will definitely get some sugar tomorrow.  I am over the moon excited about this woman.  She makes Mouse look like a total wanna-be.

This morning, College left for a two week trip and I probably won't hear from her.  When she comes back, we'll immediately make a date and we'll probably see each other at least three times.  I'm going to propose that we get together weekly at a reduced rate, which would put a few hundred more in her pocket before she heads out again.

Also, Sports and I could not get together today, and since I'm booked all week, it's looking less and less like she and I will have a chance.  I'm still holding the door open for her, since I'm so partial to Asians, but after tomorrow's date with Staci, all bets might well be off.

I said no thank you to M this morning as well.  Once she sent me pictures of her body, I was turned off.  Definitely doesn't even come close to Staci's or Sports's.

Finally, a new prospect has entered the picture.  I'll call her Mischa, for no reason.  She lives not far from Staci and shares a house with some roommates, but can host during the day.  She has a dark look that I like, and I'm flirting with her by text, but so far she's been a bit reluctant and distant rather than open and go-with-the-flow, so she might be out before I consider her seriously.

Monday, May 11, 2015

What Sucks (for me) About Being a Sugar Daddy

If you've followed my exploits and read all my post back to October 2012 -- which recounts everything dating back to May 2008 -- you'll know that I have frequented one specific Sugar Daddy website to find most of my Sugar Babies.  I have had fantastic luck there, and don't see a reason to stop.

However, I can only take it for about a month at a time, and then I have to go dark there, for one specific reason: there are just too many Sugar Babies!  I know that really, really sounds like a first-world problem, and it is, but it still makes things difficult.  Part of what makes it difficult for me is the fact that I have a hard time saying no.  Ironically, one of my common lines to potential SBs is "No thank you is a perfectly acceptable answer, and preferable to no answer at all."  It never fails.

Today I met and had lunch with Staci, a lovely woman from Eastern Europe who is in her late twenties, speaks three languages, and works in a field that allows her to be tri-lingual.  She's a brunette and has bright blue eyes, a fantastic figure, and a cute accent.  I have written before that Euro girls scare me a little bit.  A reader asked me why, and I wrote back:
Typically, they just creep me out a little. I'm just not attracted to them. My typical attraction is to all-American, fresh-faced girls next door. Because of that, I'm partial to Asian and Latina girls who are fully Americanized. That means no accents. It's funny; I don't even like watching porn with Eastern European girls. They just look too sleazy for me.
Funny how I wrote this just a month or so ago.  The thing is, Staci is fully Americanized, even with her cute accent.  She's been in the US for more than five years, speaks flawless English, and seems completely different from all the Euro girls I've met in the past.

Staci and I had a great lunch, and we spoke about topics that I have never covered with any potential Sugar Baby before.  We talked about the environment, communication, family (she's been married before and has no children), and the tendency of left-handed people to be eerily compatible with one another (she's left-handed).  We spent the entire meal not even talking about arrangements, and she even consented to taking a walk with me afterward to discuss the financial terms without other ears nearby.

After getting out of the restaurant (unintentionally located on the ground floor of a hotel), we walked around the upscale neighborhood.  She agreed to my terms, telling me that her last Sugar Daddy paid her four times the amount to see him four times as much as I want.  Ordinarily, this news would not exactly have made me feel wonderful, since it was perfectly reasonable to assume that she would continue to look for someone who could provide more assistance.  However, before we'd left the restaurant she'd told me that she'd pulled down her profile.  After I got home I went to the site and confirmed that she had pulled down her pictures, but her profile was still up.  That's the same to me, since most guys I know won't bother to look at a profile unless there's a picture.

We shared a few kisses at her car, and a laugh or too.  I think she's the one.

But here's where things suck.  I also really like Sports, and she really wants to meet with me.  We were supposed to meet last Friday, but she caught cold and had to postpone.  Too bad, because now that I've seen Staci, I'm pretty sure that my search is done.  So I'm telling Sports that she's still in the running, although Staci's more attractive physically, and has a great brain as well.  I'll meet with her because she and I also have hit it off on more than a physical level, but I'm not promising her anything.  I have told her the truth about meeting another woman.  She seems disappointed but level headed about it.

Then there's M, the blonde who was introduced to me via Chrissy, is also very attractive and wants to meet.  She hasn't gotten to the level of Staci or Sports yet, but she's flirty, bisexual (as is Staci), and open to just about anything.  Staci, however, has her own apartment.  This is nearly the clincher for me.

Finally, I sent Mouse a goodbye text today.  No sense in postponing the inevitable.  I was nice about it though, saying that although I really enjoyed meeting her, she'd probably agree with me that we didn't match up well physically.

So, it really does kind of suck that there are too many Sugar Babies to choose from, AND that I'm much too much of a pushover to say no to many of them.

Thursday, May 7, 2015

Back in the Saddle Again, Part II

Once Mouse and I were safely behind closed doors, we started talking to each other again.  (A quick aside: the hotel was the same hotel where I'd had my memorable threesome with C and The Dancer.) The hotel had been renovated and modernized and the room was large and comfortable.  Turned on the A/C, set the lights just right, locked the door, and I slipped the envelope with the cash onto the desk near the door.

As I was slipping off my shoes, Mouse said, "Since it's our first time together and we're just getting to know each other, do you think it's OK to get the money thing out of the way?"  "Already done," I replied, "it's over there on the desk in an envelope.  I always do that sort of thing discreetly, otherwise it feels like a transaction."  "Nice touch," she said.

She walked over to the bed and started to take down the covers.  "Bedbug check, sorry," she joked, but it wasn't really a joke.  You can never be too careful.  Mattress was covered so no issues there. After she slipped out of her dress to reveal her black bra and underwear, we climbed into bed and I said, "All through lunch I kept thinking that your lips looked really soft and that I had to kiss them." "Oh, yeah?" she grinned, "well you'd better do that now before I change my mind."  Very soft lips, and hungry kisses with lots of tongue.  I got between her legs and started kissing her all over, then unhooked her bra.  "These are real," I said, "very nice!"  Beautiful breasts -- ahh, the benefits of a young body.  Mouse's body was far from perfect; she had an hourglass figure, but she was overweight, though not in a bad way.  She definitely carried it well, much like Dale.

We spent a respectable amount of time kissing and exploring bodies, but we were there to fuck.  I was going down on her within a few minutes.  She tasted sweet and she really enjoyed it, particularly when I fingered her.  I noted that her vagina seemed a bit shallow, and I suspected that it might pose a challenge when I wanted to get inside her.  She moaned a lot, massaging her breasts and pulling her nipples, while she held my head.  She was very wet.  When she came, she clamped her thighs around my head and her body stiffened.  I didn't stop licking her.  "Want another?" I smiled.  "No no no," she said, "just one for now.  My turn to do you."

Mouse's BJ skills were adequate.  For one thing, she positioned herself where I could touch her everywhere (nice thinking); for another she was good with her hands and her mouth accommodated me well.  Still, there was the obligatory comment about how "huge" my dick was.  I said nothing but just smiled and moaned my gratitude at how well she was doing.

When it came time to fuck, we got the gear and I lubed up inside and out.  She was nervous.  "I have a small vagina," she laughed.  "Don't worry," I assured her, "it'll fit just fine."

We started in missionary position.  We used a lot of lube, but it definitely took some effort to get inside her.  I had to pull out completely a few times to help her settle down.  Eventually, after a couple of tries, I slid inside her and she relaxed her pussy, but her legs were still a little tense.  That took a few more minutes and me holding her legs apart   She seemed to enjoy herself quite a bit, and we did a fair amount of kissing.  After a few minutes, I pulled out and asked if she wanted to switch positions and take the top.  "Oh, no," she laughed, "I'm not ready for that yet."  What the fuck was that all about? I thought.  Oh, well.  I started wondering if this was going to be a one-off or something ongoing.

I re-entered her and we played some more.  After a few minutes I heard her say something like, "Are you gonna cum for me?"  I ignored her, and just kissed her neck.  When I stopped, she turned her head and whispered directly into my ear what I thought she'd said: "You gonna cum for me, baby? Give it to me.  Give me that cum."  I took this as her attempt to hurry things along.  I wasn't really ready to climax, but I could sense that she'd stopped enjoying herself and that if I persisted she might ask me to stop before I came.  This was when I realized that I wouldn't be seeing Mouse again.  It took about thirty more seconds, but I had a pretty decent orgasm and I pulled out.  All in all the sex lasted about 25 minutes from the first kiss.  Another wasted allowance.

She rushed off the bed, saying, "I really, really need to pee."  Ah, this was why she was hurrying me! "You should have told me before, babe," I said, "we could have stopped and taken a break."  "It's OK," she said as the door closed.  From the sounds in the bathroom, she really needed to pee.  She stayed in a few extra moments to clean up, then came out and put on her underwear.

We talked more about a bunch of non-essential things.  I say they were non-essential because at no time did we discuss getting together again.  In fact, I was surprised she didn't just get out of there as soon as she finished up in the bathroom.  Maybe she was waiting for a cue from me.  I eventually gave her that cue by getting out of the bed and pulling on my underwear, then walking over to the desk and checking the time.  "It's almost four," I said.  "Shit," she replied, "I have to go.  I have to shop for a gift for a co-worker."  Interesting exit strategy, I thought, though it could have been true.

She quickly slipped back into her dress, and we kissed goodbye.  I showered and left about 15 minutes later.

Yes, this was a waste of money for me.  I was happy to have gotten laid, but I could have waited a little longer.  I kicked myself for a few minutes, then turned my thoughts to M and Sports.  Perhaps one of them would be better than this.  I found M more attractive than Sports, so maybe I'd wait until after I met both of them before I decided who would be next.

A quick text to Mouse will be in order to thank her for the chance to meet and play with her.

Back in the Saddle Again, Part 1

Yesterday I met with the woman I call "Mouse" for lunch and possible afternoon play.  I met her at a sushi restaurant in the same area where I had met Ug-Lee five years ago (I can't believe I just wrote that I had a Sugar Date five years ago, but there it is).  Having completely misjudged the time, I arrived half an hour early, so I had some time to kill before Mouse arrived.  I checked some work emails and did some other browsing online before the phone rang with a local number I didn't recognize.  I thought it might be business-related, so I answered it in that fashion.

Then I heard a sweet sound in my ear.  "Hey, it's [real name for College]!  What's up?"  Apparently she'd gotten a new cell phone and decided that one of her first priorities was to call me.  I smiled and told her how great it was to hear from her (which it was), and we chatted for about 10 or 15 minutes before I had to meet Mouse at the restaurant.  College was finishing up her year and studying for finals, and would be traveling for a couple of weeks to visit family before coming back home. She'd be staying with a parent (much to her chagrin) about an hour from where I live, and wouldn't have a car for the six weeks she'd be in town before leaving again for two months abroad.  At first I thought my chances of meeting and hooking up with her would be slim, but she totally made it no problem, and said her parent lived near a mass transit line and she could meet me anywhere I wanted so long as it was close to a stop.  At her young age, she showed serious poise and problem-solving talent, and I felt encouraged to discuss how we'd make it work.  I would set aside the entire month of June and the first half of July to be with her, which would give us three, maybe four dates before she had to leave again.  A dream come true that a potential Sugar Baby only wanted a short-term thing.  Of course, anything could happen: she could change her mind, she could be doubling (or, yeesh, tripling) up, or she could be totally sincere.  I took this all at face value and I knew I'd make sure to give myself backup just in case things didn't work out.  I ended the call by encouraging her to send me photos of herself from her trips (or anytime she wanted) and wished her well on her finals.

Now it was time for Mouse. (A brief note: I gave her the name Mouse because one of her profile pictures had her in Mouse makeup, very cute).  She arrived exactly on time, wearing a pretty sexy black dress that stopped just above her knees, and showed off a respectable amount of cleavage.  She had chestnut brown hair (colored, for sure), dark brown eyes, and red painted fingernails.  We hugged close outside the restaurant, where I noticed her breasts were real (as in nice and soft), before going inside.

Great meal, decent conversation.  I found her engaging and friendly.  She let me order all the food, saying that she wasn't picky at all.  I pretty much found her agreeable to just about anything. I was very up-front and made sure she understood that I believed honesty and transparency were essential to making this successful.  However, I lied to her when I said I'd be taking off six weeks in June and July "to take care of some business" (which was only partially true).  She was fine with it; apparently she made a really good living and had no need for the money, but wanted something to indicate that I valued her, hence the allowance.  At this point I noticed that overall, there was just a hint of weariness, of cynicism, of impatience, as she talked about her life, her work, her previous relationships.  It left me wondering if she'd actually be as engaging in bed as she was over a meal.

I got to find that out.  As we finished our meal, I asked if she wanted to continue our date, and she said, "Up to you."  Not exactly the enthusiasm I had wanted, but I wasn't going to pass up a chance to get laid after such a long dry spell.  I had already pre-selected a hotel and picked up my phone and booked a room right away.  I texted Mouse the address and asked her to meet me there in 45 minutes.

As I got into the car, however, I realized that I'd forgotten to get lube in addition to condoms.  You know my feelings about condoms without lube; they go back to the very beginning of this blog.   So I had to make a stop to pick it up.  She had already arrived by the time I'd checked in, and we entered the elevator to our room together, her conducting business on the phone the whole time, although we both pretended not to know each other until we slipped into the room.

To Be Continued...

Wednesday, May 6, 2015

My Sugar Daddy Activity, Part 1

This week I met L, a cute early-thirties woman who worked in accounting.  We met at a local cafe about a block away from where she lived.  She brought her dog with her, a rather large creature of a breed of which I'm not too fond.  She (the dog) was sweet enough, but tied up at a rather safe distance.

L was tall; in heels she was taller than I am.  Long brown hair, dark brown eyes, nice teeth, sweet smile.  I wasn't all that knocked out, however, despite her Middle-Eastern ethnicity.  She wore too much makeup which was concealing a less-than attractive complexion.  Not acne, just bad skin tone. I looked at her hands and feet and could tell.

She'd had one previous arrangement that lasted about 18 months, so at least she was experienced. But if I had to decide today, I'd probably decide to keep looking.

Next meeting is with the one I called Mouse in my last post.  This might turn into a sex date, and I have the hotel already lined up.

Another update: One woman, a late twenties Asian I'll call Chrissy, turned me down yesterday for an arrangement because my offered terms were too low for her.  I'd started chatting with her last week, but her profile mentioned that she expected quite a large allowance, five to ten times what I was willing to shell out.  As I saw it, nothing ventured, nothing gained, right?  We chatted quite frequently over the next couple of days, and I managed to convince her to meet me if she hadn't found anyone in the next week.  When I contacted her and asked if she'd met anyone, she said no, but that she had thought it over and changed her mind about our deal.  She was so gracious about it, and never once judged my offer as cheap.  In fact, she turned around and referred one of her girlfriends to me -- M, an early thirties health care worker, a blonde Caucasian woman -- and we are going to meet next week.  Other than C's referral of Wanda to me, that was the first time anyone's ever hooked me up with a friend.

Monday, May 4, 2015

My Work Never Ends

A week or so ago, I went back to my favorite SD website to start a new search.  A Sugar Daddy's work is never done.  So many Sugar Babies, so little time!

(a brief aside: I've decided not to shy away from the terms "Sugar Daddy" and "Sugar Baby", even though I find them distasteful.  One reason is because that's what I and they are.  Another is because, like any other writer, being read by others is a huge benefit.  I don't publicize this blog for obvious reasons, but I'd need add language in the headlines or bodies of my posts to attract readers who search using these keywords).

One of the first things I did was to delete my previous profile.  It had been up for seven years and I no longer felt it served me.  There were new things I wanted to communicate.  So I created a brand new profile and uploaded more recent pictures, all behind the privacy barrier.  Once the profile was approved, I started browsing and looking at the availability of women.  I set my search criteria differently, raising up the minimum age to 27 and setting the maximum to 35.  I've written before about why I want to keep a narrow age range,  However, this time I resolved not to be so rigid about it.  If a woman contacted me who was outside the age range then I'd consider her if she could convince me why she was special enough.  I maintained my allowance range, but increased how far away from home I'd wander.  Based on my search criteria I found over 1,100 members who had profiles on the site.  I shook my head at how fortunate I was to be living in a major metropolitan area where there were lots of beautiful women.  I literally had more women to select from than I could possibly want!

After a couple of days, my inbox started to fill up with messages from women who wanted to see my picture.  So I decided to pay for a one-month membership and see where things took me.

Here a few highlights of women I'm actually going to meet, in order of my preference:
Mouse -- late twenties, brunette, works in retail, lives with roommates in same area of town where C was living when I met her.  Looks somewhat like Leah, but bustier and taller.  Gave me her phone number right away, and we've been texting.  We have a lunch (and perhaps after) date for this week.
College -- early twenties, brunette, Latina.  Currently a college student back east.  She'll be in town for only about a month and wants something short term only.  She's got this thick mane of dark hair that drives me wild, and she's very articulate.  Feels really good to have the consent of a woman who only wants a temporary fling.  No having to deceive about my true intentions.  She lost her cell phone and is studying for final exams so we're communicating by email only.  If she doesn't get her cell phone this week, which she said she would do, then I'll probably abandon this one.
Sports -- early thirties, Asian, fully Americanized.  Works out of her home near where Wanda lived, has a roommate gone all day.  We have spoken by phone and she's very sexy.  We have a love a sports in common.  Were it not for her age I think she'd be at the top of this list.
Sweetie -- mid twenties, brunette, unknown career.  Tall and busty, she looks to be a little big, but has a gorgeous face and smile.  Texting only at this  point.  You'll recall my last experience with girls who had gorgeous faces but indeterminate bodies.
Kitty -- early thirties, Asian, not fully Americanized, student.  Been texting her and she wants to meet right away for sex.  Worried that she might be an escort.  Not sure yet, but she's really, really cute.

As I get to know them better, I'll give them names, but for now I'll use these temporary names.

More later.

Sugar Daddy Blues

After the monumental lack of discretion I displayed a couple of weeks ago, which cost me my relationships with both Audrey and Sam, I thought for sure that I'd have to give up blogging about my activities.  I also feared that one of them would retaliate.  Once I stopped kicking my own ass and my fears abated, however, I realized that, despite the fact that this blog is popular for some, it's not as widely read as some others.  Those of you who have read the whole thing have my eternal gratitude, but there are new people joining every day and these readers must not be given full details about any of the lives affected by my writing.

In order to avoid future discretion problems, I went back through every single post and edited them, removing or changing any and all references to the actual ages of any of these women, where they work, what they do for a living, where they might live, where they grew up, where they attend or attended college or school, and the presence or location of any identifying marks or tattoos.  I also changed stuff about their families, my family, my age, my family's structure, and other things.  The intent was to create enough anonymity so that a casual reader could not identify specifically where I or any of these women are, or what we or they look like.  I removed pictures that identified them as well (not all of them).

The result, I believe, still preserves the intimate nature of the writing, as well as communicates my thoughts and feelings, and the sexual circumstances surrounding what I'm doing.

From this point forward, all of my posts will follow in like fashion.