Monday, October 28, 2013

Jade Reunion

Last week I gave up searching for the right girl and decided that Jade, despite her shortcomings, was the best option I had to continue as a Sugar Daddy.  In fact, had she not agreed to continue seeing me, I would very likely be writing my last post right now.

We set a meeting time at 4 pm, and, as is her pattern, she showed up half an hour late.  I had already showered, minted up my mouth, and lay two envelopes (one with the cash) on the beside table.  Jade came in the door, excited and with a cute little voice squeaking, "Hi, baby, how are you?"  Lots of kissing, hugging, and holding each other.  I had missed her a great deal.

Having gotten naked within about three minutes, I kissed her all over and went down on her.  I cannot find the right words to describe what I did down there, but I pretty much devoured her.  I enjoyed every single second of it, feeling her body twitch and writhe when she reached climax.  She moaned and shouted, and even growled a little bit.  Clearly this was a woman who had sorely missed sexual release.  "He can't do this to you, can he?" I smiled up from between her legs.  "No!  Oh, God, I love the way you do that to me!" 

Now it was her turn to do me.  Jade has a habit of shortchanging me on blow jobs, but since she's so good at it, I was going to insist on getting my fill of her mouth.  I have to say, in all honesty, Elle was better at this than Jade is, but I'm willing to settle now.  I thoroughly enjoyed Jade's talents, gladly watching my cock slide into her mouth.

We separated and got into missionary position.  "Go slow," Jade said, "it's been a long time since I've had a cock as big as yours inside me!"  Again with the size comments; am I ever going to escape them?  Unsurprisingly, I slid easily into her.  Since we were going uncovered, I deliberately went slow, for two reasons: one, I didn't want to climax before she did; and two, I wanted to make love to her.  I kissed her breasts, her neck, her shoulders, and stroked her face while I kissed her lips.  Her hips rocked with mine; we had a great rhythm going.

It didn't take long before we were pounding each other.  I had to employ a few distraction exercises to avoid coming, which were successful.  I rolled her on top of me so I could have those beautiful breasts in my face and my hands on her ass.  After a couple of minutes, Jade tried to roll off of me, but I wasn't having it!  Eventually I gave in and we finished off by spooning.  Once she came again, I started feeling a twitch and I pulled out.  Jade had warned me that she was not on birth control at the time, and she didn't bring condoms.  I trusted her, so I didn't make a big deal of this.  I wanted her to finish me off orally, but she refused (!).  She wouldn't stroke me off either.  I didn't really understand, but I wanted to get off at this point.  I did it to myself while she stroked me and rubbed her tits all over my dick, and my chest.  Once I came I was so relieved!  However, a few minutes later, I said, "You need to go back on the pill.  I want to come inside you."  She agreed.

After cleaning up, we talked some more.  Jade's unpaid internship will likely become a paid job in a month or so, but the money will be shit and so will the job.  "Gotta start somewhere," she said they told her.  She and I talked again about her finding a throwaway job serving drinks in a hip bar to make enough money so that she could move into her own place.  I told her that my objective was for her to have her own apartment and be away from this boyfriend she didn't really care about anymore.

I wanted more sex, but she said she was sore and couldn't do it again.  I told her that we would have to work on this, because I simply want more.  She agreed and said she wanted more as well.  She made another comment about my size, but I'm not going to share it because I'm just so sick of hearing them.

Because I had a bit of an agenda with this meeting, I reached over and grabbed the two envelopes.  I handed her the one with the cash in it first. "Don't open this one till you are alone," I said, handing her the other one, "but this one I want you to open now."  She gave me a little smile and tore open the envelope.  The front of the card showed a picture of a little girl throwing her arms around a little boy, who was making a little face.  On the front were the words, "I love you."  She opened the card, which read, "Get used to it."  "Awww, so sweet!" she purred, giving me a hug and kiss.  "OK," I said, "get ready, baby, 'cuz I'm gonna say it.  You ready? Ready? Here we go: I love you." "I love you too," she quickly replied.  We hugged and kissed some more. 

So we love each other.  And I don't think it bears mentioning again, but I'll do it anyway: I am not looking for Jade to be my next wife, any more than I saw that potential in Hayden or anyone else.  I'm not interested in ending my marriage.  I love Jade because she respects me, she wants to spend time with me, and because she's a good person with a good heart.  I want her to be happy.  Also, I have to admit, I want to be seen in public with her, and I want to hold her hand in public, and I want to go on dates with her, like a real girlfriend.  Because that's what she is going to be.  Sugar Baby aside, Jade is my girlfriend, my mistress, my lover.  We have a serious relationship.

And as with any serious relationship, we will have to communicate openly and honestly when problem arise.  This will not be an NSA relationship.  And I couldn't be happier.  I can practice on her how I'd like things to go in my main relationship with DW without there being serious consequences.

Monday, October 21, 2013

No Longer Fighting It

Elle and I are through.  I cannot take the struggles with canceled dates and trying to arrange time to meet her.  We are chronologically incompatible.  I will no longer be her Sugar Daddy.

I haven't yet told her this, however. 

On the other hand, I am also done fighting my very strong ties to Jade.  I contacted her today.  Here's a transcript of the convos:
Me: Are you home now?  Time to chat?
J: I'm back and will be able to talk at 12:30
Me: Voice to voice? :-)
J: yeah
At 12:40 she called me, and we caught up briefly.  She asked me about the end of my arrangement with Sam.  She hates her job, but she knows it's necessary to get ahead in her industry, and she'll be great at it once she gets past the initial pride-sucking nightmare she must endure in the beginning.  As you know, she has a live-in boyfriend, and I've been using that as a way to protect myself against getting too tied up in her life.  But getting tied up in her life is what I want.  Plus, she constantly undermines her boyfriend, and it's leading me to believe that she doesn't really love him.  After all, her nickname for him is Fuckface!

"We were in paradise for two weeks, Porter," she said, "and we had sex only twice in all that time."  "What the fuck is that about?" I asked. "How old is he?"  I thought that perhaps, being somewhat older, his testosterone levels might be low.  You can't have that gorgeous a woman sleeping next to you, walking with you, dressed in bikinis and other skin-baring clothing, and fail to act on your libido -- unless, of course, you have no libido!  But he's 35, so I doubt that's the issue.  I can attribute some of his reluctance to her emotional aloofness.  Based on what she says to me, I can guess that she isn't very nice or warm to him.  But there must be something wrong in this relationship, and regardless where it originates from, it can seriously impact their ability to be sexual with each other.

I asked a very major question at this point, the answer to which would determine my next step.  "Jade, if he were not providing you with a free place to live and supporting you financially, would you be in a relationship with him?"  "No," she said, flatly.

I heard all I needed to hear.  "Jade, I miss you, a lot. I miss having sex with you, I miss your body, I miss your face, and I miss talking to you.  I want to see you, this week.  Would you like to get together?"  "Oh, yes, yes," she replied, and the longing in her voice sounded almost orgasmic.  "And listen," I added, "Let's not spend a whole of time chatting and getting caught up with one another, OK?" She laughed as I continued, "I just want to you to come into the room, take off your clothes and hop right up onto my cock."  "Oh," she said, "you're so done for.  I need you so badly, Porter.  I so need to get fucked.  He just doesn't fuck me."  She also said that I have been the only man she's known who could pull her back from the brink of losing it emotionally, and to call her on her bullshit (which, I have to admit, spills liberally from her mouth).

After ten minutes, the chat ended, but we continued by text.  I let her know that I booked the hotel and we set a time and date.
Me: You will absolutely need a shower when we're done.
J: Music to my ears
Me: If you need to cancel let me know by tomorrow
J: There will be no canceling.  Trust me
Me: So I'm more important than Fuckface.  As it should be.
J: hahahahahahahaha
Me: BTW, I took a trip through your FB page.  You're so beautiful, so special, so sexy.  And, this week, you'll be so MINE!
J: Do you really think that?
Me: Which part?
J: Beyond the beauty, I mean. Sometimes I feel like I sound like a complete whacko.  I wanna be more than just beautiful.
Me: I don't know anything better than being a beautiful person, Jade. But I won't lie: that 26-text long thing you sent me last week was a bit whacko.  But I recognize the pain underneath it.  It just kills me that you feel pain like that, so acutely.  I want to take that all away, if only for two hours.
J: I'll take it.
Me: I'll give it.
So we are getting back together.  I don't know what I'll settle on regarding allowance.  But it probably won't be the same as before, since she has free housing now.  If she leaves him, then I'll hook her up for more.

I can't tell you how happy this makes me. 

Getting Hung Up on A Sugar Baby

My fellow Sugar Daddy blogger, David Montrose, posted a response to a comment I'd made on one of his posts.

I have to say, there have only been two girls to whom I think I'd gotten emotionally connected. One was Jade: this was the first real Sugar Baby I'd had since Hayden, and she was the real deal for me.  Jade was an emotionally available, GGG lover who told me that she loved me at one point.  I grew immensely fond of her in a short period of time, and I think that was part of the reason why I sort of hastily got out of that relationship.  Largely, I have avoided drama with her.  But, the weird thing is, I still want to see her and I find myself staying in contact and looking for ways to get back with her.  In fact, last week I texted her, "I know I made a mistake in letting you go.  Now it's too late cuz you're involved (she has a live in boyfriend now).  Huge mistake."  Where this all goes is currently a mystery to me. 

And, of course, the other was Hayden.  I've written much about my relationship with her, particularly here and here.  I truly did love her, and allowed myself to experience all the joy and pain that comes with loving someone whom I ultimately could not have.  She would never admit it, but she loved me too.  And part of her immaturity around ending the relationship was because she was incapable of loving two men at the same time, particularly one who was not available for her (not that I fault her for that).

I don't know that I have it in me for another emotional trip with a Sugar Baby.  Perhaps just fucking is what I need to focus on.  Being respectful at all times, but keeping it NSA above all else.  Am I capable of this?  Sure.  But I've been actively looking for something else, something that I know isn't there. 

Thursday, October 17, 2013

Postponed Again

Elle, with her new job, just isn't set enough in her schedule to be setting dates with me.  She texted me this morning to let me know that she had to postpone our date tomorrow morning due to a work conflict.  At least she was sweet about it:
I really need the money and your cock, but I have to show up since this job is new.
So I'm back to wondering if all this conflict over scheduling is worth it to me.

Wednesday, October 16, 2013

Elle Date #2: a Preview

Elle started a new job today.  She's digging in deep, apparently: her first shift is 9-5, and then she gets a six-hour break before working again from 11pm-8am.  Her schedule will vary week to week, so there will be no pre-planning our dates until the week of the date when she knows her schedule better.

She asked if I could meet her on Friday morning around 11 am.  Since hotel check-in times are about 3 pm and check out is noon, I have to book a hotel on Thursday afternoon and ask for late check out Friday.  We have a two hour window till 1 pm.  I picked a new hotel which is near my office, so I won't have to miss much work.

Because I have the hotel for the afternoon Thursday, I'm also asking around to see if anyone can meet me that afternoon for a hook-up.  Unfortunately, I've burned a lot of bridges of late (Sam, Jade, Arabia, and others), so I'm not confident I'll find someone.

Crimes and Misdemeanors

I've been a Sugar Daddy now for nearly five and a half years.  May 2008 was my first foray into sugar dating, having a great hook up with Anita.  From there I had a couple of freebie flings, including one with Karen, who gave me my first taste of lying sugar

There have been a couple more instances of lying in the past five years.  None of them were devastating lies, I must say, but all took their toll on the relationship (whether I wanted to admit it or not).  The biggest lie I confronted was the one Hayden told me when she revealed she was in a serious relationship with a boyfriend.  This wasn't a lie of commission.  That's telling an outright falsehood.  No, Hayden's lie was one of omission -- a deception by leaving out a crucial detail.

Karen lied about her age -- a lie of commission.  Hayden didn't tell me for eight months that she was in a serious relationship -- a lie of omission.  This lie, in retrospect, should have led me to end the relationship.  But I had already invested my heart in her, and there was no turning back, I'm afraid.

Other lies I've been told:
Ug-Lee -- first Asian girl.  She was far older and less attractive than her pictures.
Selena -- second Asian girl. Escort.
Old Lady -- far older than she said.
Paulina -- posted a picture on her profile that wasn't her.
Kim -- never told me until we were at the hotel that she didn't like oral sex.  Deal breaker.
Kay -- possible escort.  Wanted more money for sex acts other than intercourse.
Jade -- lied about her age. Said she had taken down her profile when she hadn't.
Chica -- said she wasn't a smoker when she was.
Sam -- lied about her age.

So you see, deceptions exist everywhere, from little white lies to great big ones.  Their size, I guess, depends on my perception.  I can honestly say that I've been guilty of deceptions myself, from me saying I was available for an arrangement when I was only interested in a hook up to my telling Hayden I was breaking up with her because I was concerned about the money when in fact I was hurt by her for cancelling three dates in a row. 

But there are lines to be drawn.  If in my profile I say I don't want a smoker, and a woman comes along who says she isn't a smoker when she is, or if a woman who says she's under 40 is over 40, these are deal breakers.  If a woman portrays herself as a Sugar Baby but is really an escort, that's a big lie.  When these women lie to me, the sole objective is to separate me from my money.  And in nearly every case, they were successful.

I told one big doozy of a lie to Hayden, and I paid the price for it with a four-month exile from her life.  All the other lies I told around arrangement vs. hook-up were harmless, as the worst thing that happened was that the girl left with hundreds of dollars in her wallet.  Oh, and perhaps they had sex that might not have been the best they've ever had (of course, I'm just speculating here; I know I'm awesome in bed).  But that's the risk you take in any hook-up though, isn't it?  In both cases, we lost out by wasting time, but that comes with the territory too.  You have to sort through a lot of potentials before you find the real Angel.

I'm not saying these women were worse liars than I was.  I'm only saying that the price I paid for my lies was far worse than what they paid for theirs. 

The lesson here is: Don't lie.  But, if you're going to lie, try to minimize the damage it will cause. 

Monday, October 14, 2013

Delaying Elle

I couldn't book my usual hotel today for my second date with Elle.  So I went searching for another hotel that was reasonably close to where both of us work/live that wasn't going to cost an arm and a leg.  No dice, unfortunately.  So I texted Elle and told her I was postponing.  I didn't give her a reason other than to say I couldn't make it.  She was understanding and gracious about it.

Sorry, but today is not Fuck Day.

Thursday, October 10, 2013

No Pearl For Me

As I suspected, Pearl was a Euro-girl.  She was Slovakian and had a fairly thick accent, although her English was very good.  She was easily older than 30, and even though she said she was slightly older, she's probably closer to 40.  Great body though.  She said she had experience in fitness training, which was pretty clear.  But totally not for me.

Her dyed blond hair had remnant streaks of pink and purple in it, and her dark roots were showing.  Over her pretty green eyes she wore this multi-layered, copper and black metallic eye shadow that did absolutely nothing for her.  Her eyebrows had been completely tweezed off and she had permanent lines there that appeared to have been faded over time.  Finally, she lined her lips with a dark lip liner that just gave her face an overall severe look.

One of the biggest turnoffs was the fact that she had no clear idea about what she wanted to do with her life.  She lived with her father, paying no rent.  She just left a three-month stint with the civil service, working six days a week and commuting over 35 miles each way for absolutely shit pay.  She said she had been going to a community college because she didn't qualify for a student loan, and was studying design to get work along those lines, but she knew that work in that field requires a bachelor's degree. She isn't going to finish school, but is going to try to find work anyway, at the bottom.  This is a woman who appears fairly comfortable with life at the bottom.  And that's not a compliment.

Update on Goodbye Sam

Yesterday I posted a goodbye text to Sam to end our arrangement and relationship.  Initially there was no response.  Par for the course, right?

A couple of hours later, she wrote back to say she was out of the country and would not be back for a few more days.  She gave me her email address so I could write to her there.

While I was re-writing the text, she texted me again to say that she'd gotten by goodbye text.  Her response was understanding, and she thanked me, and wished me luck.  I was touched by what she wrote.  Since I also wanted to end things on a good note, I decided to email her with an expansion on my text:

You're busy, and I got that: I'm busy too. But it just didn't show me that you were interested in me or our arrangement when I would see/read the way you communicated. In fact, it discouraged me a great deal. In the two months since we started seeing each other, I don't recall a single time when you initiated a conversation. On top of that your normal text responses were consistently one or two words. See, I didn't even know until just a few minutes ago that you were out of the country. That was probably the longest text I ever got from you. It's just not the way I like to conduct relationships like these.

Perhaps you had another SD and didn't want to tell me (maybe you're with him now), or perhaps you really didn't like me after all. Either way, it's not important anymore. You're a great girl and I wish you well. Thank you for your company.
I guess it resonated with her, because she continued to communicate with me:
I'm not much of a texter and no I do not have another sd nor am I here with a man. Simply shooting swimsuits for a catalog with a few other models. I understand my communication is not the best and I feel the timing had a lot to do with it yet that's not an excuse. I wish u the best and again thank you for everything.
I returned her email to agree that timing was horrible.  Plus I wrote, "I am like a lot of SDs in that it's more of a relationship than a twice monthly booty call."  I left off saying that I would be open to working things out if we could agree on expectations.
I really wish things could have worked out with her.  Things started off with such promise, her playfulness and beautiful face and body were about as close to perfection for me as I could have hoped for.  But, at this point in my life, I have to admit that I want more than a hook-up partner.  I want a real relationship with an available woman.  Even if it's going to be a short-term thing, what's the harm in investing in it fully?

New Potential

In about three hours I'll be having coffee with Pearl, a cute blonde who contacted me a few days back on the new Sugar Daddy website.  She sent over a bunch of pictures -- a petite-looking, cute 30ish blonde, with a curvy figure.  She says she looks better in person.  That would make her pretty damn hot.  From her pictures, she looks more like 35 or older, so I'll have to ask her about it. Also, from her name and facial features, it appears that she might be a Euro-girl.  As I define it, that's a girl from eastern Europe, and she may or may not be an immigrant.  Typically I steer clear of Euro-girls because, well, they scare me a little bit.  Her texts, however, reveal flawless English, so I'm hopeful.

I was not expecting to meet another woman now that I've begun something with Elle.  But with Elle's new job starting next week and her ridiculous commute, I have to consider a back-up plan.  Elle told me yesterday that she anticipated her schedule to be similar to what she already has.  To me, that means that she'll have one or two days off during the week (more likely one with an additional day off on Sundays).  I'll probably have to compete for her time on her weekday off, since she'll probably want to see her mother on that day.  The work days for her, with her commute, will be just impossible, given my increased workload.  So, if we can't find a very convenient day to meet, I'll just politely let her know that I'm not willing to budge on my need for a late afternoon meeting.  I presume she won't be available to take time off work with this new job.  Even still, driving back from her work location to town will just make this impossible.

Pearl and I seem to have hit it off, at least via text, so if things feel good at the face to face, I'm going to put it to the bed test.  I'm going to change tactics a little bit, though. I've already told her that I'm looking to meet up 2-3 times per month, but we haven't discussed allowance yet.  My plan is to put it out there and see if she'll consent to three times a month for the same allowance as I'm giving Elle for two times a month.  If not, then I fall back on the rationale that the allowance is for meeting every other week, so some months there would be three meetings.  There would be two such months over the next year, as I see it.  I can't see her objecting to two extra meetings per year in that case.

Wednesday, October 9, 2013

Goodbye Sam

I sent two texts to Sam yesterday:

1. What are you up to, babe?  have you found yourself with some time?

and, two and a half hours later:

2. you know, I'm wondering if we're too busy for each other.  What do you think?

No answer to either one of those.  So, after I complete this post, I'm sending a third:

3. Hi, babe.  Sorry for doing this by text.  I'm afraid this is the end of the line for us.  You have seen over the months that I like a fair amount of communication, but whether you intend to or not, you're just not responsive enough for me.  I enjoyed getting to know you a little, and wish you only the best.  Perhaps you'll find someone else better suited to your schedule and style.  Take care.

Not expecting a response.  I'm disappointed that she turned out to be such a dud.

So, now it's just Elle, and we'll see how that goes.

Crazy Jade

Two weeks ago, as I was holed up in a nice hotel while training for my new job, I was walking to dinner with my co-trainees, when I got a text from Jade:

J: I wanna have sex with u
Me: Sounds great! I'm in [city] at the [hotel].  Come down tonight.
J: What??? How long are you gonna be there?
Me: Tonight's my last night.  Back in town tomorrow.
J: Why didn't u tell me sooner???
Me: Are you coming or not?
J: Yes!!! But I'm babysitting right now.  Can I come down late, like midnight?
Me: I was thinking maybe 10.  Midnight's kinda late.
J: How about 11?
Me: Perfect.  See you then.

Then, a minute later:

Me: BTW, this is your booty call!  No allowance.
J: What do you mean?
Me: You called me asking for sex.  I'm here, come get me.  But I already have a SB.  I'm not an ATM with a cock.
J: ooooof, that didn't feel too good.
Me: a little indelicate, I apologize.  You're still welcome to come down.

I followed up over the next hour or two with a couple of texts, including one where I took a picture of my hotel bed and wrote, "You could be here right now."

Needless to say, Jade didn't come down.  And we didn't contact each other at all until yesterday.  After writing that I might take time off, I decided to reach out.

Me: Hey J
J: Hey P
Me: What are you up to?
J: I'm at [unpaid internship] right now
Me: Any chance they'll be paying you anytime soon?
J: 2 months more...
Me: will it be worth the wait?
J: Yeah. Can't really text now.  Will talk to you in a lil. XO

Two hours later:

Me: In the car.  Talk now?
J: What would you like to talk about?  I can't talk.  I'm still at work.  Besides, I think you're kind of an asshole so I don't really wanna speak to u.  You're a mean human being.  there's plenty of that out there.  I don't need it in my life.
Me: Whoa... I'm not mean at all.  I don't really know what you're talking about.  but I apologize again for being awkward with my words.  I was hoping to clear that up without texting, but I understand if you've moved on.  You're cool and I like u. 

An hour later:

Me: I don't understand you.  Two texts ago, you're giving me an "XO", so I know there was at least some minimum amount of affection there.  Two hours later I'm an asshole.  If you would give me an opportunity to clarify what I was trying to say the other night, you might not think that anymore. Let me buy you dinner.
J: Sorry, I'm in a weird mood.  I wanna show u something I wrote.  I want to see what u think about it
Me: that would be great.  when can you meet me?

What followed was a 26-text long, incoherent, babbling diatribe about the media, about secret plots they are hatching to control all of our minds.  Reading this thing, I really thought her cheese had slipped off her cracker.  I didn't know what to say, so I just said, "Take it easy, babe, and be good to yourself."

Sunday is her birthday, and I'm thinking that some of that nuttiness had to do with an upcoming milestone.  In any event, there is no conceivable way I'm ever going to sleep with her again.  Now my job is to let her go with affection and never contact her again.

Tuesday, October 8, 2013

Time Off?

Yesterday, I bought a free three-day preview membership at another Sugar Daddy website.  I'm not really a fan of it honestly.  I think a bunch of these listings are fakes.  I don't mean escorts/hookers.  I mean fake listings, listings with pictures of girls who don't exist in real life.  Just to get guys to buy the membership.  Gonna cancel that out.

There's another site I might try out: Ashley Madison.  But I've used that site before and I had no success there.  At the time, however, I was ignoring all girls who wanted a Sugar Daddy.  I was looking for a true mistress who wanted a sexual outlet with an available married man.  No go.

Elle started training for her new job yesterday.  Her place of employment is about an hour outside of the city, in traffic, each way.  If she works 8-5 M-F, she'd only be available on weekends or evenings.  That wouldn't work for me, so we'd have to stop after one date.  Damn!

Sam is a decent alternative, but I'm not sold on her either.  She just seems too aloof for me.  I like having contact with my Sugar Baby, and if she isn't going to give me more than a couple of syllables a day, I'm not interested.

I have Aura, I have Jade, and I might have one more.  I'm not particularly excited about any of them. 

I dunno.  Maybe it's time to stop for a little while, build up my new business, and focus on making lots of money.

Friday, October 4, 2013

In Limbo

Having had a successful first sex date with Elle, I've found myself with a bit of a dilemma.  What to do about Sam?  Physically, I find her more attractive than Elle, as she's in much better shape and seems to take pretty decent care of herself.  She is goofy, fun, intelligent, and pretty great in bed.  But her very laid-back personality frustrates me.  She's essentially mono-syllabic in her communication with me -- partly because she's very busy during the day -- at times when I want to hear more from her.  She never, ever reaches out to say hello on her own.  As of today, I haven't reached out to her in two days, probably the longest I've gone even without saying hello, and there has been nothing from her.

Contrastly, Elle's beautiful face and eyes (gorgeous, actually) are wonderful, and her body, while slightly out of shape, doesn't turn me off.  Her excessive body art does not excite me, however.  I am far more attracted to Elle's personality than to Sam's.  Elle is talkative, silly, plain-spoken, direct, and very expressive.  Her texts are long and informative.  She reveals herself -- sometimes even too much -- which disarms me and draws me into her life.  In bed, Elle has far more skill, although her going on and on about my cock was over the top annoying. 

On the fringe issues, Sam is bi-curious, Elle is not (although she has had sex with women many times, she says she is not into girls).  Sam has her own business and shows ambition to do much more.  Elle is going to be a worker her whole life.  Sam is younger and less mature, while Elle has lived a lot of life and offers a wealth of life experience to spice up our relationship.  Sam doesn't impress me as someone who is curious about the world, while Elle seems very open (albeit tempered by her being opinionated).  Elle has an angry side, Sam doesn't seem that way all.

While I dislike the term Sugar Daddy, I have to own that I am one.  And, as a Sugar Daddy, my Sugar Baby (ugh) should express more than a little interest in who I am and what makes me tick.  Being my companion doesn't just mean being the receiver of allowances, gifts, dinners, etc.  It includes listening, sharing, and being open.  I've always been very clear with every potential that I meet that I'm after more than a sexual outlet.  After Hayden, with whom I fell in love, how could it be any other way?

I'm not sure what to do at this point, but I'm clear that having two beautiful and sweet women to choose from as my SB, it's  a good problem to have.

One thing I did decide, however: I'm going to try a different Sugar Dating website than the one I've been using.  A couple of sugar buddies of mine have given me some guidance on a number of different sites.  I know that SBs frequently put up profiles on different sites, so I expect to run into many of them in different places.  But I'm sure there will be plenty of others who don't.  Fresh faces!

Thursday, October 3, 2013

The Long Wait is Over (and it was worth it)! -- Part 2

Last night I detailed my first meeting with Elle, all the way up to our heading upstairs to our hotel room.

The room, as I have described before, suited our needs perfectly.  After she used the restroom (during which time I snuck the envelope under her jacket), she sat on the bed while I took a seat on a desk chair.  No sense in diving in right away.  We talked about her job, which she is leaving in a week or two (which might cause a potentially very bad problem, but more on that later).  She asked me about my marriage, and the inevitable why questions.  I felt and feel very comfortable with Elle, so I found it easy to discuss this stuff with her throughout the afternoon.

After about 10 or so minutes of getting acquainted some more, I asked, "Can I just kiss you now?"  "Of course," she said.  Moving onto the bed, I locked lips with her. She took my face in her hands, which felt very romantic, I must say.  I returned the favor, letting my tongue dance around hers.  All very light touch and gentle.  The kissing grew more passionate, and we got horizontally entwined pretty easily.  Slowly, articles of clothing came off.  We laughed and kissed and talked throughout this whole process.  I told her how her tats were not my style, but that liked hers because they accentuated her arms and shoulders.  (Tangent: unfortunately, she had to show me how out of shape she was by jiggling her triceps.  "Old Jewish lady arms," she joked.  Great, thanks for that visual, Elle!  Despite the fact that she works with addicts and battered women, is a recovering addict herself, and has a great relationship with her family, Elle maintains that she is anything but "a nice girl."  She swore like a fucking sailor over and over again, just to prove it.  Tangent over.) 

Anyway, undeterred by her jiggly arms, we pressed on.  Her front-clasping bra removed, I enjoyed stroking and kissing her small breasts and tight little nipples.  In addition to the arm tats, she also has one on her neck, two at her hips, one on her side which she said she hates, and one on her butt which I hate.  A few minutes later, both of us were naked. 

Now comes the part that, for me, nearly derailed the whole afternoon.  After laughing, smooching, smiling, and having a great time, Elle started commenting on the size of my member, expressing mild concern that it might be big for her.  You all know that this happens to me a lot, so it won't surprise you to read that I resorted to my stock answer, which is to tell her not to worry because a fair amount of lube solves that problem in no time.  At that moment, it seemed that the issue went away, so we continued.

I went down on her.  She apologized that she hadn't waxed recently.  Elle struggles to pay her bills, so what do I care that her vagina was a little hairy?  In any event, she tasted sweet and she enjoyed what I was doing.  She took care, as well, to let me know that she wasn't going to "get off this way," even though she thought what I was doing felt amazing.  I thanked her, saying, "I'm such a goal-oriented guy, that I'd have been down here for half an hour not giving up!"  I fingered her and rubbed her g-spot, which really got her going.  "You don't have to be so gentle, Porter," she said.  "You like it a little rough, do you?" I responded.  So I stuck in another finger, rubbing and pumping, licking away at her clit.  She moaned loudly and rocked her hips, and really dug it, but clearly not anywhere near an orgasm.

I was ready for her to return the favor.  Happily, she paid me back with interest.  After saying, "Let's see how much of you I can get in my mouth (another cock size comment!), she demonstrated that her mouth was, indeed, large enough, and she gave me a totally awesome blow job.  I would say it rivaled anything I got from Hayden, and came close to Joni as being the best BJ I've ever gotten.  At one point, I looked down and she had reached down between her legs and started playing with herself, quite aggressively, I might add.  She was jamming several fingers inside herself.  It didn't last long before she stopped. She looked at me and said, "We always know how to get ourselves off in two seconds, don't we?"  "Did you just come?" I asked.  "Of course, look how wet I am.  She took her wet hand and stroked my cock.  "Now I get to taste myself when I suck on you."  Wow.

I could have lay there with her mouth on me for two hours and I wouldn't have complained one bit.  But I wanted to fuck her.  She was sweaty, her long hair was piled on top of her head, and my cock was throbbing for her pussy. 

I opened up a condom and the lube, applying it generously since she was so concerned about it fitting.  "Go slow, very slow," she cautioned me.  I entered her fairly easily, but seemed to hit a barrier about halfway in.  At the same time, a look of serious discomfort descended on Elle's face.  "It hurts," she said.  So this is where the afternoon nearly derailed again.  We slowly kept going, applying more lube, thinking that as she started experiencing the in/out, she would get wetter and we'd have less discomfort.  "It feels like I'm having sex for the first time," she said.  "When did you last have sex?" I said, thinking that perhaps it had just been a long time, but that wasn't the answer since she'd had sex just a week ago.  "And he was puny compared to you."  Great, more comments about my dick.  This was not turning out the way I liked it.  I said, "I don't want you to think that I'm not enjoying myself, because I am, very much, and I don't want you to think that I'm angling for unprotected sex, because I'm not at all.  But, stuff like this happens because of condoms.  They rub, they catch, and they tear, which is exactly what's happening to you."  She had already told me that she was on the pill, and I wasn't thinking we should have bareback sex, but it was clear why this was happening, at least to me.

I suggested she get on top of me to control the amount of penetration and to control the movement.  At first it went slowly, but my penis eventually got all the way in.  Rather than going up and down, she rocked back and forth, which she said felt a little better.  We managed to have a few good minutes of sex there, with me sucking her nipples and squeezing her nice booty.  But I could tell she wasn't enjoying it all that much.  So I stopped, took off the condom, and we took a break. 

At this point, Elle made more comments -- more like worried concerns -- about whether we were compatible anatomically.  "I have a small vagina!" "Um, I've been with women six or more inches shorter than you, and eventually things work out.  It's our first time.  Let's just take a break and we'll try again in a bit."  My erection was gone by this time, anyway, so we just kind of lay there for a minute or two, talking.

She wondered whether it was the condom.  I said, "I'm clean, I'm safe, but I leave that decision up to you, babe."  She suggested we try it bareback.  I said I would pull out when I come. 

After going down on me again to get me hard (man, she was so good at that!), we applied more lube and she got on top again.  I slipped in easily, as I knew I would.  We went slowly at first, but she was so wet that soon we were fucking pretty roughly.  I'm not thrilled with rough sex, but I enjoyed giving her a good pounding.  Kissing made all that pounding seem loving, though!

I rolled her over and we finished in missionary position, with me pulling out and unloading on her belly.  It was fun to clean her off, especially in that little bellybutton reservoir, which was filled to the top. 

I learned afterward that the guy she slept with last week was a sort-of-new boyfriend.  I made sure to tell her that she needed to let me know if things got serious.  I told her the Hayden story, and wouldn't you know?  Without my prompting her, Elle surmised that Hayden had feelings for me and couldn't manage to reconcile them with her feelings for her BF.  She also didn't like Hayden at all.  I know that Hayden doesn't really come across as very likeable when I tell our story, but regardless of what she or Jade have said, I think Hayden is a pretty amazing girl who lacked the maturity to handle her feelings in a genuine way.  Doesn't mean she's doesn't have a good heart deep down.  At least that's how I'm going to remember her.  Fuck what everyone else thinks.

We both showered up, I watched her pee, we both got dressed, left together, kissed in the elevator, and hugged in the lobby, in front of about a dozen people, before parting.

All in all, a successful afternoon.  We like each other.  There will be another date.

Wednesday, October 2, 2013

The Long Wait Is Over (and it was worth it!)

Today was my first date with Elle.  I waited quite a long time to meet this woman, back almost a month.  We experienced far too many delays, but I held out hope that she would prove worthy of the wait.  Through our texting, we developed what I believed was a very good rapport.  Her background and her work appealed to me, and she seemed to enjoy our conversations.  She possessed something I wanted more than her body.  I selected the hotel on which Jade and I eventually settled.  Elle would be coming from work (and, surprisingly enough, returning to work afterward). 

But before I tell you that story, I have to tell you this story: last night, she sent me a text and specified that she wanted to meet me downstairs in the hotel lobby before going upstairs, adding that she "wanted to make sure that I wasn't a cop lol".  I shot back with what I thought was an innocent enough response, but it turned out to be disturbingly cryptic to her: "Not a cop.  Too heavy. LOL"  She asked, "What's too heavy, you or being a cop?" 

Now, I could have put this issue to rest immediately by taking a quick selfie and texting it to her, or by letting her know that I looked the same today as I did when I originally sent her a picture of myself.  But, the Fates did not allow this.  I was about to have a long evening powwow with some close friends, and it wasn't a social thing.  My phone gets turned off at these times.  So the whole evening went by and I didn't respond.

The next morning, I sent her a good morning text, and said, "see you at 4. Meet me in the lobby."  No big deal, right?  We were on, finally!  Only something was hanging in the air but I didn't know about it.  Ninety minutes before our date was to begin, Elle texted me: "U never answered my question last night. What's too heavy?  You didn't look heavy in your pic."

Hah, I thought, she's worried that I won't look like my picture, and be this heavy dude who couldn't possibly inspire a woman to take off her clothes and express herself.  So, I replied, "Aha, you're worried that I'm a fat guy! LOL I was saying I was too heavy to be a cop. Those guys are in great shape.  I look the same as in my pic. See u at 4."  No response, so a couple of minutes later I send her a couple of question marks.  Again, no answer.  So I snap a selfie and send that.  No response again. 

Now I'm getting a little miffed.  I'd sent over a series of reassuring texts that she'll be meeting a guy who told the truth about himself, but she is silent on her end.  Having been stood up more times than I care to mention, I start wondering if the worst is about to happen.  Given the numerous false starts we've had, it's not an unrealistic thought.  However, I'm smarter than that and I realize I'm in my head, but I hedge my bets just to be sure. "OK," I write, "I'm heading over to the hotel now. If you're thinking at all about changing your mind, please tell me now."  No response.  I get in the car and start driving over.  The drive is across town, in pre-rush hour traffic, about 30-40 minutes.  About 10 minutes in, I text again: "Please don't let me waste my time driving across town and back, ok?"  No response.  Now, my dumbshit brain is in overdrive, and I think that she's going to be a no show.  I keep driving over, though, telling myself that if she doesn't show up, you'll just go home and refrain from unleashing holy hell on her phone.  After all, I'd only be out the small hotel bill and will have saved $600 in allowance and gifts.

About three minutes prior to my arrival at the hotel, the text comes: "Sorry I was working and didn't see your texts.  We're all good, and I'll see you in a bit."  Apparently she doesn't carry her cell phone around with her like I do every second of every day. Relieved, I smile and get all excited again.

I arrive and check in, getting a top floor room with a few of the busy street out front.  I take a quick shower and get dressed again.  The lobby, however, was too small and conspicuous, I decided, and I asked the desk clerk if there was a Starbucks or something nearby.  Turns out there was a funky coffee shop on the ground floor of the hotel building, so I went over there to investigate.  Cute, funky and with a few tables out front on the sidewalk.  Perfect.  I informed Elle of our change of meeting place and headed down there 10 minutes prior. 

She showed up just a minute or two late.  She was dressed in black skinny jeans, a flowing print top, and a little short black blazer.  She had long flowing black hair and a bright smile beneath lively dark eyes.  I stood up and we hugged warmly.  I'd gotten two bottles of water from the coffee shop and offered her one.  We spent about five or ten minutes chatting before heading upstairs...

To be continued...