Monday, February 25, 2013


I have been in three significant relationships in my life that lasted longer than a year: both of my marriages, and my three years with Hayden.  In all three of these relationships, I have had more than one sexual partner while being committed to one person emotionally.  With my first wife, most of my cheating was aspirational rather than operational, until after 3-4 years, when I started regularly seeing escorts.  While we dated, however, I made out with two girls and asked two others to fuck me before I got tied down.

With DW, I was monogamous for 5-6 years before I had my first sexual encounter with an escort.  The extra-curricular activity began in earnest, however, after about 8-9 years together, when I began my sugar activities. 

With Hayden, it was open from the start, and I probably had 15 or more different partners over that three year period.  I never really wanted exclusivity with Hayden because 1) the novelty of fucking all these beautiful young women had not worn off, and 2) monogamy isn't my thing, really.

Jade and I are talking about exclusivity.  She wants to build a trusting bond with me, she calls me her boyfriend, and she wants to have unprotected sex.  I'm torn.  On the one hand, I love sex without a condom in the way, I love the feeling of climaxing inside a woman and feeling the slipperiness that happens during my orgasm.  On the other hand, I am terrified of the idea of unwanted pregnancy or a potential STD.   I also last longer when wearing a condom, but that can change over time as I get more used to the feeling of Jade's pussy.  However, there is something really enticing about having that level of trust with Jade, with doing the work that creates a real connection, not just an "arrangement" one.  If I'm looking for a new partner in life, one who is OK with an open relationship.  Then again, Jade does not appear to be that kind of woman.  Even at this level, she wants only one man.  Would she be OK with me fucking, perhaps even loving, other women?

It's great that she wants only me right now.  But I'll tell her that should she meet someone and want to date and have sex with him, I'd want to know, and I would fully expect her to end our relationship.  This is, of course, a subject for a later discussion with her.  But I'm looking ahead. 

We are having lunch this week.  A real date, out in public (in an out of the way neighborhood, of course).  A public display of affection might be involved!

Thursday, February 21, 2013

Catching Up

I saw Jade for the second time yesterday.  I'll get to details on that meet, but first some other stuff.

Over the weekend I was in Las Vegas with DW and the kids.  Luckily, we know people there and lodging is not a problem.  Also, we always have someone to watch the kids if DW and I want to go out. And this weekend, we did.  We wanted time to be alone.  So we had a great dinner at a steakhouse and caught a show (I'm no longer a gambler, for some reason).  We had a great time.  When we got back to the house, though, I wanted to have sex.  Even though I don't aggressively initiate sex anymore, this night I certainly made it clear that I wanted to have sex with DW.  She was not interested -- I know, what else is knew?  But it just got me thinking about whether or not there will ever be an ideal situation that suits her.  I mean, at home the kids sleep far enough away from us that we can have sex with the door open and the sound won't carry.  But in Vegas, the kids are across the hall and sleep with the bedroom door open.  Further, our hosts sleep in the next room.  Forget the fact that there are two huge walk-in closets full of sound-absorbing clothes between our two rooms, DW just doesn't feel comfortable having sex in that house at any time, and we've been visiting there for the entire length of our relationship.  The funny thing is, a couple of days after we returned from the trip, she revealed to me that she was in the mood over the weekend.  So would it have killed her to close the bedroom door, turn on the TV, and be quiet enough so that we'd keep the noise down?  We have kids, so our hosts have to know that we occasionally have sex? (Or is it that, because we have kids, we should no longer have sex?). 

Also, I tried to set a coffee date with Lola to talk to her about possibly moving forward together.  As I wrote before, I have definite ideas about what I want out of an "arrangement" now: I want a real relationship with someone with whom I might actually have a future.  After a couple of texts back and forth over a few days, her response was, "I don't want to do this anymore. Sorry."  She said she had a change of heart, and she didn't want to be secretive anymore.  She didn't want to be the other woman.  She wanted a real relationship with a single man.  Fair enough.  I let her go.  Sort of suspected that's where her heart was in the first place.

For my second date with Jade, I'd located an historic hotel through a hotel website that was listing rooms for $60/night.  I looked up the place on Yelp and found relatively good reviews: "What do you want for $60?  A luxury suite?"  It was a small room, with a comfy king bed, a TV, and free WiFi.  Not much better than that. 

Jade was half an hour late (I built that into our time together, so I was OK with it).  She left the condoms at home so she had to go buy them, so that's what held her up.  She came in with a big smile on her face, which I found so nice.  We had a big hug and kiss, and we kicked off our shoes and talked on the bed for a few minutes.  She was wearing a loose sweater (I think it might have been the same one she wore the day we met) and black pants and boots.  Within a couple of minutes we were making out on the bed.  I slipped her sweater off, and as it was sort of falling on my head, I slipped it on and gave her a big smile.  She laughed her ass off.  "I love that you're so wacky," she said.

Within a minute we were naked and rolling around, kissing and grabbing at each other.  "Please, just fuck me now," she begged.  Again, I slipped my dick inside her without the condom, and we went at it for a couple of minutes that way before I pulled out and slipped on a condom.  There was no oral sex this time, but we fucked in almost every position imaginable, and she came at least twice.  I don't think I lasted more than 15 minutes overall. 

After sex, she wanted to talk about her work.  She was feeling very vulnerable about her chances for success, but I told her that what she was doing was great and that she had a unique chance to do it and get paid for it when everyone else did it for free.  Also, we talked about her moving out of her apartment, but she'll be getting a new roommate so I can't do away with the hotels just yet.  If I can get these rooms at this rate I'm okay with it though.  Finally, I asked her, "Am I your boyfriend?"  "Yes," she said instantly.  "You are my boyfriend.  I'm  your girlfriend, your mistress, your LOVER.  I like that we're lovers, but you definitely are my boyfriend."  Felt great to hear her say that.  We talked about the unprotected sex we'd had.  She said she wanted to work up to it, but she preferred it to sex with a condom.  I said, "It's entirely up to you when you're ready to get to that level, but when you're ready, we'll go get tested together.  And I'll want to see your prescription for the birth control."  "Of course," she said.

She got up to use the bathroom, before coming out to tell me, "You fucked the period out of me, baby."  Needless to say, no more sex, not even oral.  She was feeling gross because she didn't have anything to stem the flow.  I was okay with it.  I knew we'd see each other again.  I even said, "I know you are going to want sex more often than twice a month."  She nodded slowly in agreement, smiling.  "Way more."  "Ask me anytime when you want me," I replied, "but my budget is still $1,000 a month."  "I'm OK with that," she said.  "Not that I think it'll ever happen that you call me for sex out of the blue, but just putting it out there," I said.

I got out of there at the right time and headed home, hungry as hell and looking forward to seeing the family.  But I knew I had a girlfriend I could talk to on a regular basis who didn't care if I texted her every day, who wanted to build trust, who opened her heart, and who didn't really care about the money.  Well, we'll see about that last part, but for now we're really having fun.

Wednesday, February 13, 2013

What I Want

I've seen Jade once, and Lola twice, and quite honestly I am very torn between the two of them. 

Lola, on the surface, has everything I want in a partner.  She's beautiful, age-appropriate, very sexual, open to experimentation, and (seemingly) emotionally available. 

Jade, on the other hand, may not be as extremely sexual as Lola, but she is also age-appropriate, very emotionally open, and also very friendly. 

Over the past week or so, since I (sort of) ended things with Lola, I've been thinking about what it is that I really want in these arrangements.  Today I read a post on another Sugar Daddy blog that covered the money issue.  What role, exactly, does the money play?  How does the SB use the money?  If she's smart, she saves it or invests it in some kind of future-building vehicle.  But, as most of us know, these young women struggle to pay their bills (tuition, car payments, rent, shopping, partying, etc.), and they need the extra cash to keep up with those in her social circle who don't appear to have these problems.  Ideally, I think, a SB should treat the money as a bonus rather than the main reason why the relationship with the SD exists.  Hayden said, very early on in our relationship, "This doesn't work without the money."  At a very young age, living alone in her own apartment, going to a private university, and with me more than twice her age, of course that would be the main reason why she was with me.  But after 18 months together, I only gave her a raise to $500 a visit, and only occasionally gave her cash gifts.  And yet, she stayed with me, laughed with me, had multiple orgasms with me, introduced me to two of her girlfriends by telling them I was "really good in bed."  She opened up her life to me (or at least I thought she did) and she was, if not vulnerable, somewhat less guarded than she was at the beginning.  The money meant far less at the end than it did at the beginning, but it never truly stopped being a factor in what drove the relationship.  In my fantasies, Hayden would tell me that she no longer cared about the money and just wanted to be with me because she loved me.  Of course, this never happened.

As I've gotten to know both Lola and Jade, I found myself falling into the same behavioral traps into which I'd fallen when I was with Hayden.  I started thinking that the connection was really strong, and I didn't bother to tap into their hearts to see what was going on with them and how they were seeing things.  Therefore, it was all projection on my part with Hayden.  It took our last conversation to wake me up and see the relationship realistically.  I was able to put it into perspective and take the things I liked about it and discard all the rest.  That's where learning and healing begin.

Over the past several days, I have formed what I think is a pretty clear picture of what I want from the "arrangment."  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.

But, of course, my kids are too young at this point, and I'm not exiting a marriage with two fragile children to raise.  In five years, they'll both be teenagers, which to some degree is even more vulnerable than where they are now.  In 10 years, they'll both be adults, and even if they're not emotionally prepared for a divorce, they're much less vulnerable than they are now.  So that's my window of opportunity.

Armed with this knowledge, then, it's clear to me that I want something much more substantial in a mistress.  I want a lover in the truest sense of the word.  I want her (eventually) to love me, to tell me that the money eventually doesn't matter, that she'd still be with me even if I didn't give her an allowance.  Of course, I'd still give her the money, but not because it was part of the arrangement, but because I loved her and wanted to take care of her as best as I could.  I wanted someone who might possibly still be in my life in five years.

I know this sounds ludicrous.  If I wanted out of my marriage, then why not wait until I'm single to find such a companion?  Well, because of the reasons I just described above.  What this does, to some, is cast my mistress in the role of homewrecker.  But what must be understood is that my home is already wrecked; I am simply delaying the end because of my children. 

Do I think that it would be better to get out now, thereby giving my DW a chance at having another quality relationship?  Actually, no.  I have had this conversation with her.  She has said repeatedly that she'd never get married again.  My DW has suddenly become old.  I don't know what it is, but she no longer truly cares about either her happiness, her appearance, or her future.  She wants to quit working and be supported, but that's not going to happen anytime soon until my income radically increases.  And, if I leave the marriage, she'll quit working anyway just to get more child and spousal support out of me.  This is why I will stay as long as I can.  I don't want to leave her high and dry, so I'm trying over the next bunch of years to put away as much cash as we can so that when we split it up, we can both retire comfortably. 

So, I know this all sounds radically impossible.  But, as Tom Hanks' character, Joe Fox, memorably says in You've Got Mail: "Well, I'm a guy, so sometimes I want what's impossible." 

Friday, February 8, 2013

The Closure Email

Sent this email to Hayden yesterday.  Not expecting any kind of response, and not really wanting one.  Just wanted to give her my truth and be done with her.

Dear Hayden --

I guess I don't know what's left to say, but hear me out
All of the dreams of yesterday keep breaking me down
A couple of weeks back I sent you an angry text containing five words: "Three years of lies.  Thanks."  Almost immediately, I regretted sending it because I knew that our three years together weren't all lies.  And, since I figured I'd never be seeing you or communicating with you again, I had to apologize, clean up my side of the street, and admit I was wrong to send the text, which I did three days later.  Not long after that, you unexpectedly texted me back and said, "I honestly have no idea what you're talking about."  But of course you did.  And we proceeded to have a short text conversation which for all intents and purposes seemed like the last time we'd ever communicate.
But -- surprise! -- you texted me less than an hour later and asked me for money (WTF!?).  Not only was I glad to hear from you again, I was more than happy to help, so long as you called me.  Two days later, you called me from [your mom's house] and asked me for $1,000 to pay off your student loans.  I was very confused.  Not only were both your parents unwilling or unable to help you, but for some strange reason you couldn't ask your BF for help, because, you said, you'd already borrowed [too much money] from him.  You were, however, quick to point out that you were paying him back.  Your story led me to conclude that you probably hadn't even told him about your financial problems (if you were paying him back, wouldn't he be more than happy to continue helping you?  I mean, that's how credit works!).  I found that interesting, because there was so much you never told him about your first two years together, wasn't there?
I conditioned my assistance on a one-hour meeting so that I could finally have closure.  You hesitantly agreed, and I knew right away that I'd probably hear back from you that you'd found someone else to help you.  And, of course, that's what happened.  From there, however, came a very enlightening text convo, wherein you told me that not only did you not want to communicate with me ever again (where had I heard that before?), but that you'd stayed in the "arrangement" for longer than you'd wanted, for my benefit (gee, thanks), and that you'd moved on months before we finally said goodbye.  You also said that you were finally glad to be getting some of this off your chest.  Interesting, as I hadn't imagined for nearly three years that you'd have lied to me so much that you'd held back stuff like this.  Why wouldn't you just tell me that you'd wanted to move on?  For MY benefit?  Hayden, I never kept it a secret that I'd been sleeping with other women during the entire time we were together.  It was not (and still is not) difficult for me to find a sexual partner, so if you'd told me you wanted to move on, I'd gladly have let you go.  I would have been fine.  No, the real reason why you stayed for longer was because YOU got a benefit.  Money, sex, emotional validation, respect, etc., all coming from yours truly.
One of the last things you "admitted" to me was that you felt "extremely awkward" when I told you that I loved you.  Well, that directly contradicted a lot of things you'd told me before.  So what were the lies and what was the truth?  And no matter what your answer is, Hayden, it doesn't look good for you.  Whatever your answer, you come off looking young, inexperienced, immature, and frankly, cold.
See, I remember almost every important thing you ever said to me, or did with me (it also didn't hurt that I have journaled everything I've done as a SD for the past five years).  Check these out:
I remember in October 2009, when we'd been together for just a couple of months, getting a text from you that you were "dating" someone (I'm pretty sure it was the other SD who you said would pay for your boob job).  I tried to end our arrangement right there.  You might remember that my last arrangement ended when the girl had started dating someone.  However, then I got another text from you (and I wrote it down in my journal verbatim): "Babe, the sex is so amazing, it would be a shame to end it now.  He's not a serious BF."  So, was that really true, or was it a lie?  If it was a lie, then all the orgasms I gave you until then were faked.  But I'm pretty sure you weren't faking, and never did, so it must've been true that you thought the sex was amazing. 
I remember December 2009, when I told you I'd had a financial setback and couldn't see you for a few weeks.  We discussed possible alternatives so that we could continue seeing each other, at which point you said (again, I wrote this down), "This doesn't work without the money."  Pretty sure you were being honest with me then.  I always expressed concern over being able to trust you fully, because the money was always hanging over our heads.  It's the one reason why I wanted closure with you, so that you could say what you really felt without the money being an issue.
I remember how mad you got when, after I'd ended things early in 2010, I texted you a month later to admit I'd made a mistake and wanted to get back together.  You warned me not to do that again.  And, for the rest of that year, other than two nights in March, I stayed completely committed to you.
I remember how understanding you seemed when I ended things again in December 2010, after three consecutive canceled dates.  Of course, in my goodbye email, I'd written some things that weren't true, and I admitted as such a week later when I tried to maintain communication with you.  You were very angry with me and told me to delete your number from my phone and that you were doing the same.  A couple of weeks later, you canceled a coffee date with me to discuss reconciling, writing, "Our 18 months were fun, but now over."  You were adamant about not getting back together.  However, two months later, I reached out one more time, and to my great pleasure, you were open to seeing me again.  The additional $200 a month I agreed to give you was a small price to pay to be in your bed again.
I remember the lunch date we had in March 2011, when I'd learned for the first time that you had a serious BF.  At the time I didn't consider this a lie, but in retrospect I realize now that an omission of a truth is the same thing as telling a flat-out falsehood.  You deceived me, probably because you figured I'd end things if I knew you had a BF.  I was fine with it though: I only wanted you to be happy, couldn't you see that?  Why was it so hard for you to trust me?  I'd admitted my past mistakes and I apologized and I was always as open and unguarded as I could be.  I told you then that I wanted more intimacy in our relationship because I believed it would make the sex better between us.  Really, though, I just wanted you to start opening up and being real with me.  You agreed.  Over the next two months, prior to your leaving for your first trip, we got together four times, and I remember those times being some of the best times we spent together.  I remember that, on that last day in April, when I said goodbye to you, I told you that if this was our last time, I was OK with it, and that you should enjoy your trip and just let me know once you came back what you wanted to do.  I fully expected, however, that we were done.
I remember getting an email from you midway through your trip, when you wrote, "I can't wait to see you again!"  "I can't wait..."  Hayden, you were on a long trip with the love of your life, and you found time to write to me and let me know that you couldn't wait to come home and fuck me some more and spend time together.  You may not have intended it this way, but your email told me that I was important to you, important enough for you to take time out of your vacation with your man.  It was then when I realized that I loved you.
After your return, I had the most wonderful summer.  We celebrated two years together.  The sex was mind-blowing, and got better every time.  You continued your habit of dressing up for me in the lingerie that I'd bought for you.  I remember you told me, "I'm really glad that we're being more open and honest with each other." 
I remember texting you in July 2011, right after I'd left your apartment, telling you, "I love you, angel.  You're so amazing.  I had to tell you.  Now delete this text."  I remember then asking you if you were OK with being loved by two men at the same time.  Do you remember your response?  No?  I do: "Yes, I love it!"   So was that the truth, or was that a lie?  Certainly contradicts what you "got off your chest" last week when you said it made you feel "extremely awkward."
I bought you jewelry for our anniversary (which I never saw you wear again, and to this day I think you probably threw away). 
I also remember a night in November 2011, when I was out of town visiting my parents with my family.  I was out walking my dog on a Thursday night.  I remember it was a Thursday, because I knew I couldn't text you on Fridays when you were with your BF (see, I always did my best to respect your wishes and honor your boundaries and personal time).  I sent you a text, which basically was "have a great weekend, angel."  You sent me two texts in response. The first was, "You too, babe."  The second was "I luv you."  Aside from this being the emotional high point for me in the entire three years we were together, that text was memorable for me because, up until that point, you had never, ever used the word "love" with me in that way.  (Actually, that's not true.  I do remember one text you sent me in mid-2010 when you said, "I care for you, but don't love you.")  You had never even sent me a variation on it -- no "luv ya" or "<3 ya" or "I L U".  You'd called me "sexy" and "babe" but you'd never expressed emotion.  Ever.  A year later, however, and you're telling me you love me.  Of course, I wrote back that I loved you too.
With that text, though, you'd crossed the line you later said that you didn't want to cross.  And I think it scared the shit out of you.  I believe this because, shortly after that, our relationship began to unravel.  It was a night we were supposed to be with The Dancer, but she couldn't make it because she'd gotten her period.  So you and I took the hotel room.   We had just made love, and were lying together in bed, and I said, "Y'know, you can tell me you love me now.  You can say the words."  You quickly responded, "No, I can't. I won't."  I said, "Sure you can.  I wanna hear you say it."  "I won't say it," you said, "it's inappropriate."  I didn't understand, but you kept using that word, "inappropriate."  What is inappropriate about expressing your feelings for someone whom you trust and care about?  Nothing.  But, not wanting to argue with you -- and you were a little upset -- I dropped it.  But, you see, I have a great memory, and one thing I do NOT remember hearing that night was, "I don't love you, Porter."  You only said it was inappropriate for you to tell me you loved me.  And, of course, you were right.  I mean, how can you love your BF as much as you do, but love me too?  And here I was, late 40s, married, and completely unavailable, and really not interested in a long-term relationship with you.  (By the way, I still loved you, because you were so fucking lovable -- or so I thought at the time.)  But that was the beginning of the end, and I knew it.  Our nightmare with The Dancer just confirmed how expendable our relationship was.  With all you'd been dealing with -- your illness, money issues, an apartment you couldn't afford, and a boyfriend you loved and were lying to about your level of commitment (i.e., you were cheating on him), it made perfect sense that I would have to go.
Those last months were increasingly filled with sadness for me, because I knew we were nearing the end.  You had started getting more and more distant, you were frequently getting annoyed with me, and you had cut back communication to the bare minimum.  That's why I brought up winding things down in June, and I said we should plan when it would end.  Had I known that you had already "moved on," as you admitted to me last week, why didn't you have the courage to end it when it made sense FOR YOU to do so?  It couldn't have been just the money.  We were only getting together once a month at that point.  It couldn't have been just the "strong sexual connection" you claimed was the only reason why I was still in your life.  You were likely feeling terribly guilty at that point because you were cheating on the man you wanted to marry.  In fact, you had never once been faithful to him from the beginning, had you?  I remember you telling me that you liked fucking me because you liked the "naughtiness" of it.  You also told me that being with me made your relationship with your BF better.  How, exactly?  I know how it improved my marriage, but how was your having a financial/sexual relationship with a man twice your age making things better for you and the man you loved?  That's something I've always wanted to know.
When you called to say goodbye, you never said you didn't want to stay in touch. In fact, two months earlier, you'd told me that you had considered coming into town periodically, and that you thought maybe it'd be fun to hook up.  I couldn't believe you were telling me this, and I asked you, "Why would you do that?"  Now THAT made no sense, although I wanted to be friends and know you and your life.
But, I never thought that you and I would not be friends, would not somehow figure out a way to stay in touch over the years.  After all, I knew you loved me, at least at some point.  I was good to you.  I respected you, honored your privacy, celebrated your successes, supported you when you were down, gave you gifts, fucked you better than most men did, drank in your beauty, and knew that there was no one out there like you.  I worshiped you.  Yeah, you could say I was obsessed, and that is my one regret.  But I always came from a good and honorable place.  After all, you had given me so much, more than I could ever repay.
Now, unfortunately, so much of it feels like it could be tainted, false, a lie.  I know that my money helped you, and I was glad to help you as much as I could.  I know you enjoyed having sex with me for quite some time, if not all the time.  And I know that my company pleased you.  We had a lot of laughs together, and your smiles lit up my heart every time.  But if, like Wanda suggested, you were just telling me the things you thought I wanted to hear so that I would continue to come back, and if you never really gave a shit about me beyond what I could do for you financially and/or sexually, then it all feels ruined. 
I cannot take the idea of having wasted three years and thousands of dollars on someone who didn't care, who used me, who lied to me. So I won't. Even if you were snowing me a little, I will choose instead to remember those sweet loving things you said as sincere, all those orgasms as real, all of that appreciation you showed me as genuine.  I'm going to chalk up your inconsistent behavior, and your aloofness and occasional hostility and cold bluntness, as a product of your young age, your inexperience with adult relationships, and your immaturity.  Truthfully, I still have much to learn myself, but at least I admit it.
I hope that this long email gives you stuff to think about.  These are the things I wished to get off my chest, which you so casually refused to let me do.  I truly believe you're a good-hearted, wonderful woman, with a great life ahead of her.  I'm thrilled that you're in love, that you're enjoying your life with your BF.  You may choose to forget I ever existed, but I doubt you can.  Despite what you said at the end last week, I was important to you, and you to me.  Our three-year, frequently-interrupted, slow-motion experiment in illicit love transformed both of us.  It made me a better man -- of that I am certain.  I think it affected you too, in a good way.  Someday it may show up in your life.
One last thing before I go: In early January, I found your Facebook page through your BF's Facebook page.  I assume this means that after you read this you will block me from viewing anything having to do with you, including your business page.  Actually, I am OK with that.  It makes sense.
I will miss you, Hayden.  And I will always love you.

Thursday, February 7, 2013

First Time With Jade

Yesterday I met Jade for sex for the first time.  I had been out all day on appointments and got to the hotel right on time to check in, shower up, and rest up before she arrived.  I left the allowance on the side table in a white envelope.

Jade arrived ON TIME.  She knocked on the door, and I let her in with a flourish, which she found cute.  She put down her stuff and within a minute she was in the bathroom freshening up.  When she came out she looked happy and ready to play.  She jumped on the bed and we chatted for a few minutes.  She wanted to know how the end went with Lola.  I told her, but not too much, just enough to make sure she understood that it was now over.

After a few minutes I just jumped in and started kissing her.  I detected a faint odor of cigarettes and asked her if she'd been smoking.  "Pot," she said, "just before I got here."  "You smoked in the car?" I asked.  "I'm so stoned right now!" she laughed.  I didn't quite believe her, as I definitely smelled (and tasted) the tobacco on her.

It took us awhile to get out of our clothes, but she was absolutely stunning.  Not a hard body, but in decent shape.  Her breasts did not feel enhanced although I did see the scars.  I loved her dark, almost purple nipples, and feasted on them repeatedly throughout the afternoon.

She has an amazing mouth!  When she went down on me I couldn't help but compare her both to Hayden and Joni.  Joni gave me the best BJ I'd ever had, but Hayden was also extremely talented at it. Jade put them both to shame!  Spitting, deep throating, massaging my balls, stroking the head -- she had great skills.

When it was my turn to return the favor, I marveled at how dark her pussy was.  Since she was half Asian, I expected dark skin, but again, almost purple!  I tasted the initial taste of urine, since she'd just peed, but that went away quickly.  I tongued her everywhere, including her ass, which made her shudder.  I stuck my middle finger inside her.  Her pussy was tight, and I could feel her pubic bone very close to the front.  I wondered how easily I would fit inside her.

She came within a couple of minutes.  Looking up at her at that moment, I loved watching her body shake and contract with each wave of orgasm.  Intense!  She begged me to kiss her, so I slid up her body and kissed her so she could taste her own pussy.  As I lay on top of her, I rubbed my throbbing dick against her opening, and slowly slid myself inside her.  Again, I'm having unprotected sex... I knew she was on birth control, but we'd already discussed this.  We could get to this point after testing and trust.  What was she thinking?  What was I thinking?

"I should probably put on the condom," I cautioned.  "It's too late now," she said, "just fuck me."  "Umm," I said, "you're pretty high."  I stopped moving inside her and looked her in the eye.  "You wanna come to your senses now?"  "You're right," she said, "get the condom."

I pulled out and put on the condom.  I got the thin kind that feel like nothing, and indeed I didn't detect much difference with the condom on.  Still, with it on, I felt less inhibited and really let go.  She had orgasms in every position -- missionary, cowgirl, side by side, and doggy, at which time I finally came inside her.  I quickly pulled out and disposed of the condom, which was full of my sperm.

Lying in bed together, we chatted a lot about my previous experiences as a Sugar Daddy.  I told her all the "funny" stories (those that involved deceptions by the girls) and the one dangerous one.  I didn't go anywhere near the STI story, as that one was going to remain a secret, but I did go into detail about how hot the threesome with Hayden and the Dancer really was.  Mostly, though, I talked about ending things with Hayden and how I felt like I no longer could trust my instincts when it came to the "connection" between me and the girl.  She said that Hayden seemed really young based on what I'd said.  Funny that my friend Luke said the same thing.  Jade also noted that Hayden seemed kind of cold the way she could just separate the sex from the emotional connection.  Perhaps it was just the recent color added to my Hayden story, but it seemed clear to me that Hayden was more like a guy when it came to casual sex.  When I told Jade about how we both told each other "I love you" she said that Hayden must have been scared shitless since she already had a boyfriend.  The more I thought about it last night after Jade, the more I realized that my earlier interpretation was probably true, but it didn't matter at all at this point.  Hayden was gone forever.  Forever!

Jade and I talked some more, she played me some music that she liked, and I asked her to suck me off.  "Wash," she said, "I hate the smell of latex."  I got up and washed off my cock and balls, then came back to bed.  She gave me an expert BJ again, this time letting me direct her to putting her finger in my ass.  Unfortunately, she didn't get that far, but she did massage my asshole with her finger.  I told her I wanted to fuck her again. "Condom," she said, fully sober!  I put on another condom and we fucked for maybe a couple of minutes.  She got very excited but didn't climax again.  I, on the other hand, actually had no problem coming again!  I pulled out of her and begged her to "suck my cock, suck my cock!" as I pulled off the condom.  "No way!" she laughed.  I jerked off and came all over my hands.  We both had a laugh about my wanting her to suck me off as I came.

I was late and I had to rush to clean up and get dressed.  Jade stayed at the hotel for another half hour to nap and clean up before she took off.

I think that Jade and I are going to have a great time together.  I meet Reena tomorrow.  After our conversation two days ago, however, I'm not convinced that she and I are going to connect.  She came across as a good girl and not very passionate.  Hard to tell though.

Tuesday, February 5, 2013

Goodbye, Lola (for now)

Because I am really attracted to Jade, and think that Reena is also a possible fun playmate, I've decided to end things with Lola, at least for now.

I called Lola today and gave her the news.  Because she was in between places to be, the call was fairly short.  I apologized to her for disrespecting her concern about having unprotected sex with me, and particularly about the fact that I tried to make light of it.  I explained that I had sensed that our connection and level of trust were much stronger than they actually were.  She was trying to be nice about it, but she sensed that I was about to end things because, well, she asked, "Do you not want to see me anymore?"

I explained that I felt like I had destroyed any chance of trust between us through my actions, and that I realized that I was really bad at gauging a woman's level of trust or chemistry with me.  I said I needed to sort through some stuff and take time off from seeing anyone (it was a lie, but I didn't really expect her to believe me anyway).  I said I would reach out to her again in a few weeks.  If sex and/or relations with these two other women don't match what I had with Lola, I'd gladly go back to Lola.  However, I'm not expecting her to wait for me.

 I felt guilty when she said she had just today decided to hide her profile on the sugar website.  Ugh...

Truth is, I really like Lola, but I think Jade might be more fun in the long run.  Plus, the prospect of unprotected sex without having to worry about pregnancy is a real turn on for me.

C'est la vie.

Monday, February 4, 2013

It's Pouring

My membership period on the Sugar Daddy website expires today, so I did what any normal SD does: I went crazy with messages out to as many potential mistresses as possible!  There's always "someone better" available, which is why most people, even if they're straight dating, hold off on taking down their profiles after they find someone. 

I got a lot of responses, both good and bad.  First I heard from Summer, who is mid twenties and owns a boat where she says we would be meeting.  I'm liking that idea.  Summer's extremely sexual, and loves to flirt.  She's bisexual also, so that's something that Jade is not.  But Summer's photos, on the other hand, are not extremely flattering.  She doesn't have the cutest face I've seen, but her body looks pretty nice.  I set up a meeting with her for late in the week, but I might cancel depending on how things go with Jade on before that.  I can't spare all this money to fuck all these girls.

I also heard from Reena, a "marketing entrepreneur."  She keeps a place both in town and about 90 minutes away (probably her parents' place).  She had a bunch of pictures -- bikini ones, party dress ones, face ones -- all with that stupid "lemon mouth" look, and she sent me a bunch more.  Great looking girl, tight body, cute face.  Definitely a WASP-y look about her, which could mean good or bad, just not sure.   We couldn't chat over the weekend, but today we've been going back and forth.  She is also down for the same arrangement as Jade, but she's willing to pay for the hotel out of her share, which is a huge plus in her favor.  I don't know yet if she's bi, but our ongoing texts might reveal something.  Setting up a meeting with her for late in the week.

Finally, I chatted during the Super Bowl with Heidi, a blonde who lacked all kinds of charm.  Her first response to my note was, "How much and where?"  She had completely blown it with that note, so I wrote back, "Wow, charming response. See ya."  This touched off a brief snark exchange, where she wrote, "Simple question, that's what the site is about.  Says so in the description.  So what are you offering and what do you want?"  I replied, "Someone who waits to discuss money until after some rapport is established.  In other words, not you.  Sorry."  She called me an asshole after that and tried to insult my financial status as cheap.  Typically lame. 

Finally, there was Nikki (another Nikki), who was in her early twenties, half-Hispanic and very cute.  Sent me some nice pictures of her in a cute dress and another face shot from her driver's seat (those kind of pics are so common!).  She couldn't host and she was too young.

Anyway, looks like my week is already packed.  I'd better make some money or this will not last long!

Weekending with Jade

Jade and I spent this past weekend doing a lot of texting and talking.  I'm really starting to like her.  I learned that she uses birth control (a shot, not The Pill), and she said that, after trust is established and we both get tested, she would be open to bareback sex with me.  But for now, condoms only!  Of course, I agreed.

Already though, she's having some misgivings about moving out west to pursue her career.  She has a crazy roommate in the same business and the roommate bent her ear on Saturday morning telling her all kinds of horror stories.  I told her to hang in there and rely on her own hard work and making connections.  Trouble is, the roommate is right, and it will not surprise me if Jade finds she has to fuck her way into many advantageous situations.

We have a date for this week.  Because of her roommate I have to book a hotel on top of the $500, which I don't like.  Money is tight right now so I'm a little stressed.  But Daddy must fuck!

Saturday, February 2, 2013

I Was Right, and It's Now Completely Over

Just as I had predicted earlier, Hayden found someone else to loan her the money.  She texted me just before I was leaving my office for the day that her mom had agreed to lend her the money.  "And I'm sorry," she continued, "but I really don't think we should meet."

I was not at all disappointed to hear this, but I continued the conversation for a bit to see what I could get out of her.  "I don't understand why this is so hard for you to see me for an hour," I wrote.

"I don't want to see you anymore, Porter," she replied.  "The last few months of the arrangement I stayed in for your benefit, not mine."  Well, I thought, there's a nice bit of truth, and definitely in line with what Wanda had said last week.

I told her that I'd sensed her withdrawing six months before we ended it.  "Was The Dancer the trigger?"  "My being in love with my boyfriend was the trigger.  I wasn't going to have feelings for you because you were married.  It was supposed to be just for fun," she said, "but you told me you loved me and you took it too far."  She said she was glad finally to get these things off her chest.  I was fine with all of it, really.  There was no sense in rehashing it.

"Have a blessed life."  I wrote.

She then wrote that my telling her I loved her was "extremely awkward" and made things very difficult for her.  Well, that exposed her as a liar for telling me that being loved by me was "great" for her.  Again, Wanda was being proved right.

"I'm sorry that being loved by a good person is awkward for you.  I will always feel that way about you.  Bye."

And with that "Bye," Hayden exited my life forever.  I went to meet with Jade after that.  Since yesterday I've felt relief that it was finally, completely over with Hayden.  She's going to have a great life, and so will I.  I wish her well.

Lessons learned for me.  Do not love your mistress.  It's a recipe for drama and confusion.  And, if your mistress falls in love with someone else while you're dating, end it immediately!

Jade Wins

Met Jade yesterday for Happy Hour at a local wine bar.  She got a little turned around and wound up a block or so from where we were meeting, so I walked over and met her to escort her to the wine bar.  She was dressed in black pants, a thin sweater that was pretty low cut, and boots.  Her long brown hair was very sexy.

We grabbed a couch in the wine bar in the back so we wouldn't be seen.  I ordered her a pinot noir and myself a cabernet.  She also ordered food off the bar menu.  Hadn't expected that, but OK!

Jade had a vaguely Asian look to her but I couldn't pinpoint where.  Thai?  Vietnamese?  I asked her "heritage."  She said she was Eurasian.

The conversation revolved around her career in the entertainment business, and the complete end of my relationship with Hayden (which I'll post about next).  I was in a great mood being with her, and she smiled a lot and touched me often. Good sign.  We also talked briefly about my marriage and why I was doing the Sugar thing.  She said that women change after they have kids.  Don't I know it!

Later, we agreed on the terms of the arrangement.  Twice a month, $500 per visit.  Since she had income from her work and would likely see a lot more in the next year, she wasn't particularly pressed for cash.  I kept checking out her face, which was exquisite.  Her body was slamming too.

Jade mentioned that she had just moved to town two weeks ago after spending a couple of years living in the Southeast.  She hated it there, particularly because people were so fake there, especially the women with their fake bodies.  I mentioned my aversion to enhanced breasts.  She said her boobs were fake, "but they don't feel that way at all.  You can feel them if you want to."  She moved her hair aside to show me.  "I'm so proud of them."  "I'm not gonna feel your boobs in here," I said, looking around, "but I will later."  I leaned in to kiss her just to see if she'd take the bait.  She did.  We had a nice kiss.  Later, the kisses evolved into some serious making out with tongues.  It was hot.

After we kissed the first time, Jade said, "So, you know that because we kissed, I've picked you.  You're it.  I'm gonna take down my profile from the site.  Is that OK with you?"

I wasn't quite sure what to say.  I had Lola to think about, and she was pretty awesome.  I didn't want to disappoint Jade either.  "Um," I stammered, "how about you wait to do that until after we fuck?"  I tried to keep it light and funny, and it worked.  She laughed and said OK.

We hung out for about 90 minutes and then I had to get going.  I paid the bill ($50 for two glasses of wine, a salad, and a grilled cheese sandwich, yikes!) and we left together.  Her car was parked a few blocks away, while mine was a bit closer, so I insisted on driving her to her car.  That way I'd get to feel her tits.

We got into the car and immediately started making out again.  I said, "Now I can feel your boobs."  I put my hand on them over her clothes.  "No," she said, "feel them."  She pulled down her sweater and bra, and I got to touch them.  Holy shit, they felt completely real.  Better than Hayden's swollen globes, and even better than Dale's which were amazing.  I teased her nipple and pinched it a little bit, which she liked.  We kissed for a good minute there, and she reached for my now growing cock.  I tried to slip my hand down the back of her pants but she pulled back.  "Time to go," she said.  "Great, thanks for the boner," I replied.

On the way out of the parking garage, she confessed that she actually three years older.  "Even better," I said, "because at the younger age you were almost too young for me."

I drove her to her car, and luckily, even though there was a lot of traffic, I was able to pull over and park for a second to kiss her again.  We decided to get together next week, and I think that I also decided to let Lola go.  Sorry to say, the unprotected sex incident and her reaction to it and inability to laugh it off sort of gives me the feeling that perhaps we're enmeshed a little too much.  I think it's better to cool it for a while.  Alternatively, I can hang onto her until after Jade and I fuck, because if we're not sexually compatible, I'd still have Lola.  I guess I can hedge my bet for a bit.

Friday, February 1, 2013

Lola vs. Jade

Lola and I had a great time this week, despite having unprotected sex.  A couple of days ago, I had a text convo with her over a few hours' time:

Me: Morning, lover!  I really think I'm going to struggle with waiting two weeks to see you again.

Nearly two hours go by, then:

Me: You must be at work.

L: No, Sorry, Just crazy busy.

Me: It's OK.  Miss u.

L: XOXO.  I told you I'm going out of town right?

Me: No.  For long?

L: I'll be back Monday for my mom's birthday

Me: Nice. Have fun!  Are we out of coutact during that time?

L: I'll be in Baja so no cell service.

Me: Nice.  Safe flight!

L: Driving

Me: Tijuana?

L: Estero

Me: Never heard of that place.  I just dislike Mexico.

L: Its' free

Me: Free is good.  Come back horny, OK?  I masturbated last night thinking of u

L: OK.  And I did this AM.

Me: Was I wearing a condom?  LOL

L: Pretty funny

Me: Gotta laugh at it.

L:  I actually don't think it's funny at all, but I'm glad you do.  At least you find it funny.

Me: Lola, I'm not trying to minimize it at all. 

I then tried to call her on the phone, but got her voice mail.

Me: Can you call me please.

Ten minutes go by, then --

Me: Are you angry with me?

Twenty-seven minutes later --

L: I don't have time for this.  You're fine.

Me: Yes, I'm fine.  Are we fine?

Twenty-five minutes later --

Me: OK, well have a great trip.  I hope to hear from you next week.

I did not like the way she handled this conversation, and I do not like how she is trying to blame me for the fact that we fucked without a condom.  Once I got inside her the second time, she had two orgasms, so clearly she was enjoying herself.  Whatever her issue is, if she doesn't feel like discussing it with me, then we can simply end things.  It was a mutual decision, and it was wrong, but we're both responsible for it. 

What I'm thinking is that we have gotten a little ahead of ourselves too fast.  The way we meshed was nearly immediate, and perhaps she's a little too needy emotionally.

So, today, I'm meeting Jade, a beautiful mixed-race girl in her mid-twenties from my home state.  We share a passion for football and music.  I have cash in my pocket and I'm going to see if she's adventurous enough to escape to a hotel for a quick fuck.  Let's see, shall we?

First Phone Call in Five Months

She called me today, as promised.  Within a minute, though, she had to hang up, as her mother walked into her room.  A few minutes later, she called me again.  Turns out, she's staying with her mom as she recuperates.  I asked why she wasn't in her town.  Her doctor is in northern Cal, she said.  Apparently, she broke her nose six weeks ago, and scar tissue had formed, so it was time for the nose job.  She said her nose was extremely swollen, and she'll be staying with her mother another week or so before she drives back to her town.

This news forced me to change my plan to drive next week to her town to hand her the money in person.  But I wanted to know more about why she felt it necessary to call me for the money.  She said her boyfriend has already loaned her thousands and she couldn't borrow any more.  "I'm paying him back," she said.  I asked her how long she needed to pay me back, and she agreed to three months.  Honestly, I'm not sure I'll see the money again, but I hope she can at least pay back some of it.

Last night she'd texted me that she needed $1,000 to get current on a student loan, and that her father could not help her (and neither could her mother apparently).  I could manage that.  I said, "I'll help you, Hayden, but you need to help me too.  This comes with one small catch." 

"What is it?" she asked.

"I want to hand you this money personally."

"I won't be near you for months."

"I'll drive to you after you get back.  See, I want that one hour of your time that I asked for before you left."

Hayden didn't argue with me about it.  She seemed willing to meet me, but it would have to wait till she got back to her town.  Plus, she was uncomfortable meeting me in her town since she knew too many people and was afraid of being spotted.  So I suggested that we meet halfway, and she could pick where.  I figure it'll be a couple of weeks before this happens anyway.  I asked her if she was going to back out and refuse to meet me.  She said, "Well, I'm really high on Vicodin right now so don't take anything I say seriously...just kidding.  Of course I'll meet with you."

We caught up briefly, and I briefly told her why I stopped seeing Wanda.  We then talked about logistics.  I told her that if I wasn't able to hand her the money, there were only two ways to send it -- by mail or by wire.  She said she couldn't think of what to do, and that she'd text me when she figured it out.  We ended the call, and I told her I missed her.  She replied, "I...can't say anything to that."  What that means, I have no idea, but it doesn't matter.

At this point, I'm half expecting that she'll find another person to loan her the money rather than meet with me.  Which would be fine, I guess.  Still, it would be really great to see her again.  I'm going to really check my hopes and expectations to avoid feeling disappointed.

And Just Like That.... Open Again

I've deleted Hayden as a contact on my phone.  I know her number by heart, but it's the symbolic act of deleting the contact that signals that I'm ready and willing to move on with my life.

Just a few hours ago, I wrote about how Hayden and I texted each other and she said she would appreciate no further contact "anymore" unless she reached out.  Of course, I interpreted that as a nice way of saying she wasn't going to reach out ever again.  I deleted the thread of texts after she wrote, "Take care."

Less than an hour later, however:

H: I know this is really random, but can I borrow some money?

I'm thinking, what the fuck is going on?

Me: Oh, now you have to call me.

H: I can't talk right now because I have cotton up my nose, but I have an overdue school loan bill that I just found out about.

Five months go by without a meaningful word, and now, less than an hour after she says she doesn't want contact with me, she asks me for money to help her with her loan payment.  Why isn't her boyfriend involved in this?

Me: Hayden, when you can speak to me over the phone, let's discuss it.  I am willing to help but it's inappropriate to talk about this by text.

H:  OK I will call you when I can.  I would pay you back.

Me: I know you're good for it, angel.  So sorry you got rid of that beautiful nose.  I loved it!

I'm thinking, something's up that she hasn't asked him, or if she has, why isn't he helping her?

H:  I didn't.  I hit my nose on a shelf and broke it.  So I had to get it done.  :-(  So much for trying to be a handy man.

Me: :-( I'm so sorry

H: It really hurts.

Me: awww.  Leaving my office and will be driving the next 30 minutes.

H: I can't talk on the phone till tomorrow or fri.  I sound retarded right now.

Me: OK, I waited six months, I can wait another day.  I'm sure you sound adorable.

Seven minutes pass,, then...

H: Only for a minute.

Me: What's only for a minute?

H; I can't chat for a minute... Sorry I'm on Vicodin and ambien, a little out of it

Me: No problem, beautiful, just call when you can.

So, now I'm in my head again.  Of course, I'll help her however I can.  But this is going to cost her.  I will get my closure meeting now.  I'll have to drive about three hours to see her, but it'll be worth it.  Plus, I want the money back in like a month.  No sense in creating a new relationship (even if it's just financial) if it won't get me anywhere.  We're not friends anymore.  I plan to find out why her boyfriend can't help her out.