Friday, August 30, 2013

A New Girl Emerges

In response to my message to her on the sugar daddy website, a girl I'll call Berry contacted me, and we struck up a pretty cordial, playful convo.  She's in her late twenties, blonde, probably Jewish, and from the east coast, not far from where I grew up.  We come from different planets in a lot of ways, culturally and politically, but so far I have enjoyed the energy level and humor.

As she is travelling right now, we don't have the time to meet, but when she gets back, we're going to meet for coffee.


K-Bear met me at the hotel, located in a nondescript neighborhood heavily populated with Asians.  The room was comfortable and catered to the Asian customer (many of the TV stations were Chinese, Japanese, or Vietnamese).

She showed up 15 minutes early.  Good thing I'd gotten there an hour early to freshen up.

The second she walked in I immediately understood why she only sent me pictures of herself seated. She was, as I wrote last post, thick in the thigh, and she had a pretty sizable butt.  I'm not a big fan of big butts, myself, unless they're proportional.  Hers wasn't.  Still, she had a cute face and a nice smile. Her voice had a deeper pitch than I'd expected, and she showed no hint of an accent.  I learned later that she'd been a US resident since the age of six.  She wore a small diamond stud in her upper lip, off to the side.  It made for interesting kisses.  I enjoyed her perfume, which lightly wafted around her.

She joined me on the bed for some light making out.  No tobacco breath, thank God!  After a few minutes, she excused herself to shower up, coming back out in just a towel.  "You're naked!" I smiled.  "Well, once my clothes come off," she said, "there's no sense in putting them back on." Eventually that slipped off and I got to sample her whole body.  If you'll remember from the last post, I wrote that it looked like she had nice boobs.

"Real or fake?" I asked.

"I wish they were real."

I saw no hint of a scar, so I remarked that her doctor had done a great job.  The felt firm, but not too firm like Hayden's.  K-Bear had thick legs and a bit of a paunch, plus her butt was very soft.  Not in shape at all. Still, I had her naked, and the envelope was on the table, so I was committed at this point.  I got naked and turned out all the lights (what is it with you women and lights?).  "Oh, my God," she said as she took hold of my hard dick.  "Told you I was big."  That was the extent of the dick talk.  We kissed some more, lots of tongue.  I eventually kissed her all the way down to her pussy.  She had a sweet, very tight pussy, and I licked and sucked on her for a good long time.  She moaned and rocked her hips a little, especially when my fingers entered her.  It was clear that she wasn't going to come this way, so I gave up and asked if she wanted to return the favor.

Oral sex was not K-Bear's forte, but it wasn't awful.  She gave it her best, and really slicked me up. Enjoyable!

I slipped on a condom and lubed us both up.  It took a little work, but I got inside her.  Her vagina was somewhat shallow, so I never felt like I got very deep inside her.  Nevertheless, K-Bear really, really enjoyed getting fucked.  Her moaning was loud and I was a little concerned about people walking outside the room hearing us.  Over and over again, she kept having orgasms.  I lost count, but it had to be at least 10.  I rolled us into cowgirl position and she rode me.  One of the drawbacks of her having pretty short legs was that she couldn't spread her legs very wide, so I was constantly opening her up to get deeper.  When I grabbed her ass to pump away, she started moaning again.  Her ass was like jelly, but I enjoyed holding on tight!

After another handful of orgasms, she said she needed to pee, but I told her to hang on, thinking that perhaps she might squirt.  I reached around her and rubbed her labia as I pumped inside her.  It didn't take long before I was coming too.  Even though she'd said she wanted me to pull out, I didn't, and had a pretty intense orgasm inside her.  She got off me pretty quickly and went to the bathroom. Guess she really did need to pee!

After sex, we talked awhile. Like Chica, I knew I wasn't going to see her again, so I told her the Hayden story (a little abridged this time to be brief).  She was blown away that I could have a three-year relationship with a girl half my age and actually love her without wanting to have a long-term relationship.  When I found out that K-Bear had only had one serious boyfriend in her whole life -- while she was in high school! -- I realized that she couldn't possibly understand the situation.  She was, even at her age, very immature.

I caught her smiling a little bit.  "What?" I asked. "I wanna do it again," she said eagerly.  Fine, I said, and excused myself to shower up.  She followed after I got out.  Both of us clean, I let her suck me again from a fully flaccid starting point.  She managed to get me pretty hard, but I was sure I wasn't going to come again.  I slipped on a condom and we fucked again for about 5-10 minutes.  More orgasms, more moaning, and very hot!  I came again inside her, and I was done.

I cleaned up and sat in a chair, checking my phone for messages.  As it had been nearly two hours, it was time to part.  She got dressed and I let her out, then I showered and headed home.

All in all, a pretty decent encounter, albeit a one-time thing.  I sent her a text from home: "Very nice time today. Exhausted beyond belief."  About half an hour later she responded: "I had a lot of fun.  I can't stop thinking of your big cock. :-)"

Pretty perfect place to end things with her, don't you think?

Thursday, August 29, 2013

K-bear Preview

K-bear and I will meet for sex later this afternoon.  We had a very frank talk about what we like and don't like.  And she sent me a nice picture of herself, clothed.  In all pictures she's been seated, so I got curious and asked her about her height and weight.  She said she's 5'1" and 120 lbs.  This is about the same size as DW, so she's probably not heavy.  But since K-Bear is Asian, my guess is that she has proportionally shorter legs, and they looked a little thick in the picture.  Still, her boobs look really nice, so I think I'll be pleased.  I texted her this morning to confirm and also asked her what her least favorite part of her body was.  She copped out and answered, "I don't really know.  I'll leave it up to you to decide."

In any event, she only wants $350 so I won't feel so light in the wallet if she turns out to be less cute in person.

I'm not all that opposed to chunky girls if they carry it well.  Dale was definitely on the chunky side, and I have to admit that Sam isn't the slenderest girl I've ever seen.  Both of them have fantastic bodies, however.

More later.

Wednesday, August 28, 2013

A Trying Week, With Some Silver Linings

I have abandoned Rocky as a potential, as she has not responded to several texts I sent her to let me know when she was available to meet.  My last one started out as, "OK, last try..." so it's pretty clear that I'm done after this.

Jade still wants to be with me.  Here's the text convo we had last week:
J: Sex with u is memorable
Me: Oh it is? What do you remember?
J: Very much so yes.  Everything.  The chemistry.
Me: I especially liked the chemistry of feeling my uncovered dick inside you LOL
J: We can do that
Me: No we can't anymore.  You have a bf, and he's not monogamous
J: Yes he is... we had a discussion.  I just told u that so u don't feel bad.  And I just wanted u to wear a rubber because u have a gf!  So, yes...I lied.
Me: I'm not in a position to discuss this right now, hun.
J: LOL... u take everything sooo seriously.  Smoke weed.  It's not that big of a discussion to be had.
But in truth, it is.  If I'm not OK with Chica lying about her smoking, or with Katie about her age, then I'm not going to be OK with Jade lying about why I needed to wear a condom.  I didn't have a problem with wearing a condom, not at all, but I wasn't going back to bareback with Jade no matter what, especially if she had a bf.  Further complicating the matter is that she lives with the guy.  I'd have to be a fucking idiot to hook up with her now.  So she's now gone from my life, for good.

On, the plus side, I am going to meet K-bear tomorrow, after a fair amount of persistence on her part. Truthfully, I want to fuck this cute little Asian girl awfully bad, and her arrangement terms are only $350 a visit.  Pretty nice.

Another girl named Ann responded to my profile on the website and has accepted my terms.  Her last question to me was about protection, which I said was absolutely required unless she was using birth control, that we had both been tested, and that trust had been established between us.

I guess what this means is that I'm not fully satisfied with Sam, so I'm still looking.

Thursday, August 22, 2013

Sam Date #3

She forgot the condoms and lube again.  Couldn't find them at the drug store, and was too embarrassed to ask for them.  So I saved the day.  I should have deducted the $20 I spent from her allowance (maybe next time).

She got there 30 minutes late and quickly washed up.  Came out in her lingerie (black lace with pink trim).  Got on the bed and we smooched for a very long time.  She put her arms around  me, ran her fingers through my hair, stroked my arms and back, nuzzled into the hollow of my neck and shoulder.  Of course I reciprocated.

I got her naked after I got naked, and I touched and kissed her everywhere.  I got between her legs and licked her for a long time.  Her body twitched and she moaned often, but I wasn't feeling an orgasm even after 15 minutes, so I gave it up.  I got between her legs and ground my dick against her pussy.  I managed to get the head in before she said it hurt a little bit, so I lubed up and started over again.  I got all the way in for just a few strokes, and then I pulled out and put on the condom.  Missionary and cowgirl.  The room had a full length mirror by the side of the bed, and she spent a lot of time looking at herself fucking me.  "It looks hot," she said.

I wanted her to kiss me so badly, so she leaned down and gave me a deep kiss.  I wrapped her in my arms and pulled her close, moving her body up and down on me.  "I'm cumming," I said.  "Cum in me, baby!" I unloaded inside her, and I felt her body twitch in time with me.  When I was done, she sat up and her body kept twitching involuntarily.  "You came with me!" I smiled.  "Surprise!" she said, still twitching.  So fucking hot to cum together.

We talked after about her business and our pets.  She had a rough week with the company, but she also made some big strides in getting closer to her goal of opening a pet store.

We only spent 90 minutes together, and it felt like much less than that.  I can't wait to see this girl again.  We crossed the threshold of hanging out to having a relationship.

Monday, August 19, 2013

What Do I Really Want?

In the past two weeks, I've had sex with three different girls who are not my DW.  Sam and I are just beginning a new relationship, Chica was a temporary dalliance, and returning to Jade was a moment of weakness.  In none of these experiences did I come away feeling empowered, validated, or appreciated.  I just felt lighter in my wallet.

The refrain of the Yes song "I've Seen All Good People" is playing on my Pandora as I write this: "I've seen all good people turn their heads each day, so satisfied/I'm on my way."  Why am I not feeling satisfied, and why do I not feel like I'm on my way?  Why do I feel like I'm getting less and less bang for my buck?  Given that the sex has not been all that bad, the obvious question is: What Do I Really Want?

The day I hooked up with Chica marked one year since I'd last seen Hayden in person. I've been thinking about Hayden a lot lately.  Not because I'm pining away for her and secretly wishing that she'd leave her boyfriend and return to me.  No, it's because a year is a good time to reflect, and there was something different in that relationship that set it apart from every other relationship (including the attempted ones) I've had before or since.

Hayden did not provide me with endless hours of intellectually stimulating conversation, although she was very pleasant to talk to.  She did not come to me for business advice.  We talked a lot about her life, her love issues, but increasingly in generalities.  Once she and her boyfriend got very serious, my role in her life diminished considerably.  I'm under no illusion, after all this time apart from her, that she was somehow my soulmate.  From a sexual standpoint, no one pleased me more, and no one was or has been as much fun to be with as she was.  And that's pretty much what it was.  And yet, when I left her apartment, I always felt great, better, happier, fulfilled, validated.

From Wanda onward, I've felt less and less like there is another woman who is going to match Hayden in terms of what she brings to my life.  Is it because of what I'm bringing to it?  I certainly think it's true that if you want something out of a relationship, you have to bring it.  I wanted love and affection from Hayden, so I brought them. When we were together, we had fun, we smiled a lot, we were loving, and we cared about each other a lot.  No matter what she'd say now, I know that Hayden cared about me.  Today, I guess I'm not really bringing that.  Having experienced the brutal way Hayden ended our three year relationship, denying me closure or a chance to put the whole thing into perspective in real time rather than through my own imagination or intuition, I know that I approach these arrangements in a different way now.  As much as I like Jade, or Lola, I am holding back.  I am withholding love, withholding affection, and holding back deep appreciation or caring.  Now, in fairness to these girls, I didn't really start experiencing any depth of emotion with Hayden until we'd been together at least a year.  But I certainly didn't walk out of her apartment at any point in three years feeling nothing more than $400-500 lighter.

I believe I came close to something with Jade, but ended it before it got any more enmeshing.  Part of that was because I wasn't 100% confident that she possessed the emotional stability to keep our lives separated. She'd asked me to be her date at a party, asked me to attend a business function with her.  She called me her boyfriend.  Now, I like looking at fire and sometimes playing with it too, but I know in the back of my mind I can get burned. This is how I approached Jade sometimes (most of the time).

I remember writing this six months ago:
Over the past several days, I have formed what I think is a pretty clear picture of what I want from the "arrangement."  But before going there, I also had to ask myself what I wanted in my life.  And, if I'm being brutally honest, I had to admit that I wanted something more emotionally meaningful than what DW was offering me.  I had to admit that her emotionally rigidity, and her sexual frigidity, to say nothing of my demonstrated anger and resentment toward her about these things, had ruined any chance I had of a life-long commitment with her.  Did I see myself with her in five or ten years?  No.  I finally had to admit that I wanted out of my marriage.
Things have changed for sure.  With things at home slowly improving, and with things out in the field feeling less inviting to me, I have to wonder if, perhaps, an emotional connection is too big a burden to put on my extramarital activity.

Maybe, at the end of all this mental masturbation, I just want a better partner than Sam, or Jade, or Wanda, or Lola. So far, no one has come along to do that.  And so maybe I just need to keep looking.

Saturday, August 17, 2013

Familiarity Feels Good

I arranged to meet Jade at a very out of the way hotel in a neighborhood that neither of us ever visit.  The place was decent, actually: a pretty big room with two queen beds, a clean bathroom, and a working A/C that kept the room nice and cool.

Jade showed up 15 minutes late due to traffic, but we'd been in contact the whole time so I didn't care.  She couldn't get in the elevator to my room because the elevator required the user to swipe his/her room card.  Not having considered that, I had to go down to get her.

She was dressed in a long orange print dress, cut very low.  No bra.  Hair up and wearing wedge heels.  Looking very tan.

Once we got to the room, we started making out pretty much right away.  We talked about life and got current, but for the most part we were there to have sex.  She announced that I had to use a condom this time -- no more bareback with her. Damn!  I hadn't brought them, but she had the box of condoms I'd originally bought on our first date.  No lube, but she assured me that we wouldn't need it.

She also said that she'd just two days earlier finished a course of antibiotics for a urinary tract infection.  "Why am I fucking you, then?" I asked.  She said that she was clean, no more infection, and that she'd gotten it from the switch in her birth control.  "It's common for me to get an infection when I go from pill to shot, or back again."  I was a little leery, but I knew she wouldn't have agreed to meet with me if she thought that I'd get an infection too.  As it was, I knew I wouldn't be going down on her under any circumstances.

But going down on me?  Oh, yeah....

Jade's oral skills had improved over the last couple of months, and she took to the task like someone who wanted to show off.  I got more deep throat sucking than ever before, more spit, firmer strokes, more licking.  She did it all.  I almost came, which would have been fine, but I wanted to fuck her too.

Slipped on the condom and slowly entered her.  Once we got going it felt very familiar and extremely nice!  What was different this time, however, was how much kissing we did.  Before we hadn't kissed much, but Jade was literally shoving her tongue in my mouth.  I love that shit during sex! 

We fucked a good 20 minutes and then I came inside her.  I pulled out and cleaned up, noticing blood on the tip of the condom.  "Babe, you're bleeding," I called from the bathroom.  She checked, and sure enough, she was.  No more sex today!

We talked awhile, played each other some music we had been listening to, and laughed a bit.  I showed her pictures of the other girls I'd met, and even dug up recent pictures of Hayden from her Facebook page.  When Jade got a look at the girl I'd loved for three years, her jaw dropped.  "That girl is fuckin' gorgeous!" she said.  I couldn't hide the smile on my face.  I can't believe, still, that I was lucky enough to have her in my life for so long.

Jade told me she now lives with her old boyfriend, and they have a relationship.  While I didn't say it, this announcement effectively ended any possibility of reuniting with her.  I've broken a few rules (especially recently with Chica) but this was one rule I was, I hope, never going to break again.  I simply don't want to compete for any woman's attention, ever again.  Even though Jade said that she and her boyfriend had an open relationship (to illustrate it, she told me that he was gone for the weekend with "his other girlfriend"), I wasn't buying it.  "Other than me, who else have you fucked since you got back together with him?" I asked.  "No one," she replied, and so I knew she was full of shit.

After two hours together, I had to leave, so I showered up and got dressed.  I told her she had to leave with me, but she wanted to stay and use the bathroom.  I didn't want her to stay even though she said she needed to poop.  Last time I let her stay, she stayed the whole night, rented a movie and ordered room service, on my credit card.  Not OK.  So she left with me.  We kissed goodbye.  She might think we'll be seeing each other again, but probably not.

Friday, August 16, 2013

Jade Returns

Today I will be seeing Jade again.  Yeah, I'm a sucker.  Remember those pictures?  That's why, OK?

Hasta, Chica

I texted Chica the next morning after our epic date.  "I had a great time with you yesterday, but today I'm a little upset."  Got her attention of course.


"Well, I went back and checked out your profile, and you said there that you were a non-smoker.  But you smoke, so that means you weren't being truthful in your profile.  And that bothers me a lot."

Now, her response was such an awful lie, I almost didn't have the heart to call her on it, but I did.  She said something like, "But I'm not really.  I was just so nervous about getting together that I tried it to see if it would relax me.  Sadly, it did."

I wasn't buying it, I told her.  "It's not like you took up cigarette smoking for the first time yesterday," I wrote.

"I really don't know what to say," she wrote.

I let her down easy. "It's OK.  You're cool and fantastic in bed.  But I specifically selected non-smokers in my search because I don't like smoking.  It took me hours to get that taste out of my mouth.  Plus the fact that you weren't truthful is, I'm afraid, a deal-breaker for me.  Call it ironic, but I really value honesty.  I wish you the best."

And that was it.

No Rocky

I canceled on Rocky yesterday.  You'll remember from my post of a couple of days ago that Chica fucked the shit out of me and I was completely spent afterward.  I did not sleep well that night, contrary to my expectations.  I woke up yesterday cranky, hungry, and not at all in my power.

I texted Rocky a note saying I needed to postpone due to car trouble (yeah, I'm so original).  I asked if she were available the following week, but she said she had out of town guests all next week (yeah, I've heard that before).  When I suggested the following week, she did not respond. So I may have blown her off for good this time.  Oh well, I still have Sam, which isn't a bad thing.

Wednesday, August 14, 2013

Fucked to the Point of Exhaustion

I'm currently lying on the bed in our hotel room.  Chica left here about a half an hour ago.  I showered and I'm dressed. but I can't move my ass off this bed right now.  You see, this girl had an absolutely inexhaustible appetite for sex.

She got here about half an hour before I did, and I was on time.  When she came into the room, she put her stuff down and threw her arms around me.  We started kissing immediately.  Things took a turn for the worse right away, as I detected a strong cigarette taste in her mouth. "Are you a smoker?" I asked. "Just a little bit," she replied.  At this moment, I'm still trying to get that taste out of my mouth.  If she smoked only a little bit, then she must have smoked the entire little bit right before she showed up.

But, let's talk about the sex!  Chica has what I consider to be an average body. I didn't mind at all that much, because she carries herself well. She really was a very sweet girl.  And, to my great pleasure, she had amazing oral sex skills. I had to stop her before I went over the edge. I flipped her over and returned the favor. I lost count of how many orgasms she had, but it was at least six.

After oral, I got between her legs and rubbed my cock against her pussy lips.  It felt so good, and I was so close to cumming anyway, I just grabbed my cock and stroked away until I blasted all over her chest. "Well," I said, thoroughly satisfied, "now we'll have to wait a little bit." She did not seem to mind. To my amazement, it didn't take me very long to get hard again. I slipped on a condom and got inside her. we tried a few positions, but the condom was reducing sensation to the point where I was losing my erection. Once I flipped her into missionary, my erection returned and I pumped away and came like an explosion inside her. Literally almost blacked out.

Exhausted, I got off her, removed the condom and passed out on the bed.  I don't cum twice that often, but there was something about her that was incredibly sexy. Maybe it was her young age, or maybe it was the fact that she talked dirty so much.

After a few minutes, both of us felt a little sticky and sweaty.  My cum was all over her chest, after all!  We got up and stepped into the spacious stall shower (the only decent feature about the room besides the very adequate A/C).  To our great dismay, we discovered that housekeeping had not left us any soap, so we simply rinsed off.  We kissed some more in the shower, and I got hard again.  For just a few precious seconds, I was able to maneuver the head of my cock inside her and give her a few strokes.

We got out and started drying off and made it back to the bed.  I threw her down and got on top of her, trying to put my cock in her.  "Oh, no," she said, "not without a condom, ever."  Without missing a beat, I slipped on the second condom and just shoved myself inside her in missionary position.  We switched it up and she got on top of me, reverse-cowgirl position.  "Slap my ass," she begged.  Who was I to say no?  Whack!  Whack!  You know, that shit just doesn't do anything for me, but if it made things better for her, okay.

I knew I wasn't going to cum, so I pulled out and slipped off the condom.  I was pretty tired by this time anyway.

We then chatted for about an hour.  I actually told her the entire Hayden story.  I even showed her Hayden's picture from Facebook. I literally have no idea what I was thinking this whole time, but I did know in my mind that I would never see this girl again.  So, I had no problem telling her all the details of the most meaningful sugar relationship I've ever had.

Then we started talking about her sexual fantasies. Chica really wants to have sex with a girl. I told her I wanted to watch her have sex with a girl or guy. This seemed to surprise her, as she had never had sex with a guy in front of another guy.

All the sexual talk actually got me hard again!  I was pretty fucking proud of myself for being able to continue getting erections.  "Do you want me to suck you again?" she asked.  I gladly let her suck again on my knob, and she obliged me by giving it all she had.  But it was a struggle for her to make me cum again, and her mouth got tired.  When she came up for air, I started stroking myself, and I asked her if she wanted to see me jerk myself off.  She started playing with herself as I did this. I actually managed to have a third orgasm. But now I am completely spent.

If I am going to have any energy at all for Rocky tomorrow, I had better get a great night's sleep tonight. (UPDATE: didn't happen)

Because of her smoking, and because she lied on her profile that she was a non-smoker, I am absolutely certain that I will not be seeing this girl again. But she was a great time, and I don't have a single regret getting together with her.

Today and Tomorrow

Today I will be seeing Chica and diving right into her petite young body.  This is a total splurge on my part, and I know it and own it.  We're not going to have any sort of a long-term arrangement, but I'll be happy to help her save some $$ for furniture for when she returns to college in five weeks.  I managed to convince her to spend four hours with me, dinner included, so that we could fuck several times.

Tomorrow I will be seeing Rocky.  This one has the potential to displace Sam, if the sex and rapport are good enough.  She's actually quite a bit more communicative than Sam, who really is a 1-2 text per day kind of girl, and those are usually monosyllabic.  Shades of Hayden, and it turns me off.

More tonight after my date with Chica.

Monday, August 12, 2013

Chica and Jade

This young Chica has got me a little obsessed.  We've been texting each other all day.  Then, this afternoon she called me.  What a cute voice she has!  Plus she's articulate and intelligent, a college student at a state university.  She's also staying in an apartment for the summer not 10 minutes by car from my office.  I so wanted to drive over there and bang the shit out of her.

She told me she started touching herself during our conversation, particularly when I let her know that I wanted to watch her masturbate and make herself cum.  Plus, she's been extremely vocal in her appreciation for the assurances I've given her that I really like her very, very small breasts.

Normally I would post a pic of her to make my point about how cute her body is, but since she's really young (and I'm going to check ID before I ever lay a hand on her) I will refrain.

Then I was going through old pics on my phone and ran across a couple of Jade that I took on our last date.  One of them was taken right before we fucked and the other right after I unloaded on her.  Hot, no?

I'm having thoughts of taking Jade back but that isn't going to happen.  I don't want to have this girl back in my life because she has the potential for drama, and I don't want that.

Now, Chica is a temporary fling and I can swing having her and Sam in my life.  However, I am also going to fuck Rocky this week, I hope.  If she's better in bed and hotter all around than Sam, then Sam is done.  Rocky may live farther away, but she has her own place.  I save over $300 a month going with her and get potentially better sex.

Good problems to have!

Other Girls...

While I am somewhat satisfied with Sam so far, and like the idea of embarking on an adventure of sexual awakening for her, in a corner of my mind I'm holding out for someone better.

A week or so ago I started chatting with Rocky.  She's an actress, mid-twenties, about 5'6" with natural tits, dark hair, and lovely green eyes.  She's very sexual, and really has definite ideas about what she likes.  I find her very intriguing, but she's more into being fucked than foreplay.  At my age, foreplay is the best thing to prolong my enjoyment, so I truly prefer a girl who likes foreplay.  Sam likes a lot of foreplay too, so there is that.  Rocky and I have a date scheduled for this Thursday, at her own apartment.  We'll meet for coffee nearby and then retire if she feels like taking me home with her.  Because I'm not sure I want to spend the money to be with her, I'm holding her off as a short-notice girl, making up an excuse about having to be available for my kids, who start school this week.

A few days ago, I got a response from Chica, a Latina girl under 20.  Yes, I know, way below my age limit, but she has my attention today because she is only in town for five weeks before she returns to college.  She is very petite, about 5'1", with dark hair, dark eyes, and dark skin.  She sexted me some amazing pics. Very, very small breasts, which I absolutely love because her nipples are so dark, they look like candy to me.  A great ass, and a great figure as well.  She's a cutie pie, and she's unbelievably sexual.  PLUS, she'll accept $300 for a visit to hang with me for over two hours.  She said she loves foreplay, and cums best through oral and fingering.  Yes, that is what turns me on the most.  And she loves being on top when she fucks.  All working for me.  We have a date scheduled for Wednesday afternoon at a hotel (haven't booked it yet; could still back out).

Finally, there's Jade.  She's been reaching out and wanting to get back together.  She said she'd accept $100 less than before because she really needs the help.  I don't know.  I'm a little bored with sex with her, but going bareback is a huge plus for me.  Actually, I'd give her the full allowance if we could meet at her place. I told her that today, and her response was that she was living with her old boyfriend again at his place.  This puts her out of the running altogether, since I do not go with anyone who has a significant other, even if it's a past lover who is still in her life.

Friday, August 9, 2013

Sam Surprises

Yesterday was my second date with Sam.  I went in with guarded expectations, as the first date was, predictably, a bit awkward, but also really nice and playful.

This date was scheduled a bit later to accommodate her crappy schedule.  We set our date for 5 pm instead of my usual 3.  To take advantage of the situation -- as I always do -- I suggested dinner afterward.  She eagerly agreed, and I made reservations at a nice Italian place near the shoreline.

Because I had to make a stop to pick up condoms and lube (she left them at home), I got to the hotel with about 15 minutes to spare.  Didn't leave me much time to freshen up, and Sam was due any minute, so I texted her that we could freshen up together.  A little naked time in the shower?   Could get interesting, no?

Sam showed up just five or so minutes after I did.  The room was just a couple of doors down from the previous room, but in a more secluded corner.  There was no neighbor on the side where the bed was.  Plus, there were a bunch of people at the pool in the courtyard, so we could make a little noise and it wouldn't be heard.  I gave her a big hug and kissed her all over her face, eliciting a few sweet giggles.  She was wearing a Harvard t-shirt and dark shorts with flip flops. Definitely a beach-y look today.  Wasn't sure how it would go over in a fairly upscale restaurant, but whatever.

I suggested a shower together, but she demurred, saying, "I'll go after you."  No worries, I said, and I took off my clothes and climbed into the shower.  Sam peeked around the shower curtain just as I was turning off the water and grabbing a towel.  She wasn't wasting any time with freshening up, which was sensible.

We started making out almost immediately after we were both dry.  Again she started massaging my already hard cock, using a little saliva to make things slippery.  "I like it when you suck me," I suggested.  "I did that last time, didn't I?" she asked.  "A little, and it was great.  More, please!"  She had adequate oral skills.  Not fantastic -- she was no Joni, and not as good as Hayden -- but she was pretty good.  Considering she liked to massage me with her hands, I found it odd that she took her hands away when I was in her mouth.  Again, no complaints, just making an observation.

Her body felt so nice and smooth -- the great benefit of being young! -- so I sat up and switched with her. Remembering that she preferred direct clitoral stimulation, I focused right there.  When I stuck in my finger, it was too much for her, so I pulled that out.  Still, she twitched, and moaned, and rocked and swayed her hips in circles in rhythm with my tongue.  It was hot.  "Wanna try putting it inside me?" she asked.  I wasn't quite ready to give up going down on her, but I obliged.  I got on top of her and kissed her, stroking her face.  I was in a romantic mood, and she was really quite lovely.  My cock was positioned for unprotected entry, and my rocking hips managed to gain entry for the head, but of course we were sensible and I withdrew to put on a condom.

Sex was great -- missionary, reverse cowgirl, lazy dog, finishing up with doggy.  As it was last time, I couldn't tell if she had an orgasm, but she was very wet.  She did tell me later over dinner that she came twice.  "Didn't you feel it?"  "No," I replied.  "Maybe you can tell me next time when it happens!"

We didn't spend much time in the room, as we wanted to get to dinner.  I drove us the mile or so to the restaurant. Finding a parking space around the corner, we walked the block or two.  I looked around at the people to see if there were anyone I recognized.  This was not a neighborhood I frequented, but there were a few families DW and I knew, and I wanted to make sure that I wasn't spotted.  I told Sam I'd be walking a slight distance away for that very reason.  She understood, of course.  As we neared the restaurant, I said, "Let me go in first, just to look around to make sure no one's there that I know."  The place was full of strangers, so all was good.  We picked a table in the back, behind a wall, and I put my back to the door (probably not a good idea).

The dinner was great, although it only lasted an hour, since the restaurant seemed driven to turn the table over during a busy dinner rush.  The food was very good though.  Sam had an interesting palette, enjoying roasted beets and then pomodoro pasta.  She did not join me drinking wine, but I really loved the pinot noir I ordered.

After dropping about $105 for dinner, I took her to the car and began the drive back to the hotel.  On the ride back, I asked her if she had any sexual adventures that she'd like to explore with me.  "Oh, my," she said, stalling.  "Listen," I said, "I'm under no illusion that girls today have pretty much done everything, so it's okay if you can't think of anything."  "Is there anything you'd like to do?" she asked.  Another stall.  "For me, it's not about new things, but about doing things again with someone new."  "Well, I'm sure it's every man's fantasy to be with two girls at once."  Turns out she'd never done that before, had never had sex with a girl, but knew someone who would definitely go for it.  A "supermodel," she said.  Well, we'll see about that.

She is actually quite inexperienced in kinky stuff, but she said she's definitely open to new experiences.  This was a surprise, and in my eyes, a huge plus for me!

Big kisses good night, and off to enjoy the next two weeks before we hook up again.  And yes, we will hook up again.

Thursday, August 8, 2013

Catching Up

I've been off for a little while, dear readers, so please forgive me for lumping in a bunch of stuff here to get you all caught up on my life.

Today I see Sam for the second time, and we're having dinner afterward.  She asked for me to move up our dinner reservation.  Perhaps sex isn't as good as I thought it was.

It's been an interesting couple of weeks.  The day after I saw Sam, I started getting the feeling that perhaps she didn't enjoy her time with me as much as I did.  She is monosyllabic when it comes to texting, and there just isn't a lot of time for talking on the phone, so my head plays games with me and I wonder if I made the right choice.  Given her comment earlier today, I'll see if that plays out in the way we relate to each other later today.

About a week after seeing Sam, Jade texted me and asked how I was.  Of course, she really wanted to know if I'd found someone new, and that question came about a minute later.  "I have, actually," I wrote back. "We just saw each other for the first time yesterday."  She told me she had started dating someone, a guy she'd dated when she lived back east who was now here in our city.  Given the fact that she never had good things to say about this guy, I was surprised to hear this, but given how needy she could be, my surprise was muted at best.  "I thought you were done with this guy," I wrote.  "I will be soon," she replied, "I'm about to dump his ass again!"  "Drama," I wrote, "fun!"  "So you're going to have an arrangement with this girl?"  "It's too early to tell," I said, "but I like her."  That was the last text, and haven't heard from her since.

Meanwhile, my doubts about Sam started to fester even more.  I went back to the sugar daddy website and tweaked my profile a bit.  A few days later, girls started answering my messages or reaching out to me.  They ran the gamut of age and experience, as well as geography.  Those in the next county were immediately out.  Those under 23 were almost immediately out, and those over 40 were immediately out.  But a couple stood out:

Rocky: 26, mixed race (but white), brunette, very fit, about 5'6".  She didn't post her face pics on the profile because, she texted me later, she was a working actress and was being very discreet.  Apparently not working enough, but perhaps enough to keep her public profile clean.  We've been trading texts, and we talked on the phone once.  She lives on the other side of town, and it would probably be a long drive to see her.  However, she had her own apartment, and came across very very sexual.  We shared some fantasies -- she's bisexual and wants to have another threesome.  I made a date to meet her next week.

K-Bear:  She's back.  We scheduled a date for two weeks from today, since she'll be out of town next week.  I'm only giving her a one-time fuck -- she only wants $350 per visit, which is great -- so I'm being cagey with her.

Heather: a real estate professional, late twenties, black, and very beautiful.  Meeting her tomorrow for coffee.

Aura: also back.  She's been reaching out to me, saying she hadn't been having enough fun.  I poked that comment to see if she'd consent to a freebie, but of course that was a no-go.  She meant fucking and money, and that was no surprise.  "I'm a one arrangement at a time guy," I wrote her.  I'll reach out to her again if Rocky and Sam don't pan out, but I really appreciate that she wanted to check in with me.

There were a bunch of others too.  One, in particular, wanted $100 just to meet and was so disrespectful it was a wonder she had anyone in her life, let alone a sugar daddy.  I took the high road with her though, and wished her the best of luck.  Another wrote to me that she thought we'd be a good match.  She was 21, and mentioned in her profile that she had a kid.  I politely wrote back that we weren't a good match because she was too young and had a kid.  My profile clearly stated that I did not want anyone who had a "significant other, including a child."  She wrote back that I was a "close-minded [sic] idiot."  I let her have that blow since there was no arguing with a child like her.  And again, I wished her luck in her search.  A few more are still out there and I'm waiting to hear from them.  If I do, I'll update.

On the home front, DW and I spent a good amount of time together as our kids went off to sleepaway camp for two weeks.  We did a bunch of stuff around the house, went out to dinner a lot, walked our dog together, and were very touchy-feely with each other.  We had sex twice in the first week, but none after that since her monthly showed up.   It's been a great time, and I feel like I've come to a deeper understanding of her as a sexual person.  Which is to say, she's just not there.  This makes it all the more perfect that I engage in this sugar lifestyle.  I'm not retiring anytime soon.

I'm also in the process of changing jobs.  Stressful, as I'm not earning any money these days, but this will be resolved very soon.  More to be revealed there.