Sunday, July 28, 2013

My Journey with Sam Begins

I got to our hotel, near the beach and along a busy main road, about 45 minutes early.  They let me check in before 3.  It was a first floor room in a back corner.  I bought a couple of bottles of water from the front desk and tossed them in the mini-fridge.

The room was big, with lots of floor space around the comfortable king-sized bed.  I set the A/C for a comfortable temp, stepped out of my clothes, and took a quick shower.

When I dried off, I got dressed again and texted Sam to let me know once she was parked, and I would leave the door open so she could just walk in.

Pretty much right on time, Sam walked in!  A colorful knit crop-top was matched with what appeared to be orange shorts (hard to tell in the light), and she wore flat sandals.  Her hair was pulled back and she held it in place with some hairpins.  Hug, kiss, hi, you look great, so do you!

Some small talk about work.  She said she had changed clothes in the car, and that she was wearing business clothes before.  It would have been perfect, I said, that way it would've looked like we were both here for a nooner in the middle of our day.

More kisses, lots of touching.  I was liking where this was going.  She slipped off her sandals and stood on her toes to kiss me.  "I don't like putting my feet flat on the floor," she said with a goofy smile.  Wait, what?  Just one of a few idiosyncratic things that she would utter during our time together.

During one of our hugs I asked if her boobs were natural.  "All me," she replied.  I told her that it was rare to meet a young woman these days who hadn't had her boobs done  "I know, a lot of my girlfriends have had boob jobs."  I also learned that Sam had once been a dancer, which would explain the amazing legs and very tight tush.  "Dancers to me are like crack," I said, using a line I have frequently used in the past when hooking up with dancers.  "Really?"  "Yep," I said, "so I'm already high right now."

She hugged me and then turned away from me, rubbing her gorgeous butt against me, making me a little hard.  I took her hips and held her there.  "Yeah, you're making that happen," I said.  More kissing, light tongue. She smelled like flowers, but I could tell that she'd been out most of the day and the application of perfume had been recent.  No worries.

She excused herself to use the bathroom.  When she came back, she joined me on the bed, on which I lay.  I immediately stood up. "Nope," I said, "not ready to be horizontal with you yet."  I took her hand and we hugged and kissed on the floor, more tiptoeing from her.  "I know, it's weird," she said.  "I just don't like my feet on the floor."

I then took her back to the bed, where, on our knees, we resumed making out.  "I like making out a lot," I said, "do you?"  "Very much."  Back onto the floor, where she unbuttoned and removed my shirt.  I removed her sweater, revealing a black bra underneath.  Her skin radiated warmth, even though it had gotten a little cool in the room.  I held her face and kissed her deeply.  She turned away and took off her shorts, revealing a black and blue g-string.  "No fair," I said, "that was for me to do."  "So sorry.  You can take these off though!"  "I have to catch up to you first," I said, so I jumped off the bed and took off my pants and socks.

Both in our underwear, we continued to kiss, on our knees on the bed.  Finally, I couldn't take it any longer and started to move to horizontal.  We just made out for the longest time, lots of light kisses, not many deep ones, which suited me fine.  Her all-natural boobs were not as firm as I normally like, a lot less firm than my DW's boobs which were much older, but they were cute, pretty large, and fun to play with.

As I moved down her body, she quipped, "This is the part where my panties come off."  I laughed and said, "Uhhh, yeah."  I really dug her goofy sense of humor.  If I had to sum her up with one word it would be playful.  She has a silliness that I find very sexy.  Throughout our time together, she was light-hearted, goofy, witty, and easy-going.  Perfect complement for my own way of looking at things, and a nice contrast from some of my previous girls, who sometimes thought it OK to be porn-star slutty.  I like the sluttiness, make no mistake, but sometimes they took it too seriously, and sometimes came off a little phony.  I have to admit that Hayden, occasionally, seemed a little insincere when she'd act that way.  "I'm your little slut," she'd sometimes say when I was fucking her.  Yeah, she was, but voicing it in that particular way sometimes felt forced.  OK, tangent over...

Sam returned the favor by taking off my underpants and  releasing my already rock-hard cock.  No words of surprise, no gasps, no worries about "will it fit?"  I was relieved.  She went down to kiss the head and lick it a little, but she didn't put me in her mouth right away.  She just stroked it, and every now and then she added a little saliva to slick things up a bit.  She did this extremely well!  Using two hands to massage me in alternating circular motions, massaging my balls (gently), and working her hands up and down the shaft, which I told her I liked better than when she rubbed the head too much, she sent me nearly over the edge.  There wasn't a lot of oral involved, but when it did happen, it was nice.  Since I wanted everything to be organic and, well, normal, I didn't say anything about wanting her to suck me more.  We'll see if she continues the handwork or does more oral next time.

When it came my turn to go down on her, she did let me know that she preferred direct contact with her clit as opposed to her labia.  When I did lick her on her pussy, she'd tense up and laugh.  "Ticklish there?" I smiled.  "Very.  I like it right on my clit."  So, naturally, I obliged.  She moved a little with my tongue and complimented me by saying it felt "really good.  You're very good at that."  I put a finger in her to rub her g-spot (Hayden used to love when I did that), and Sam responded with some moaning.  She was pretty quiet overall though.

After a few minutes of this I was ready and I asked if she wanted me inside.her.  "Oh, yes," she replied.  Having thought ahead, I had both the condom and the lube right at the bedside (Prepared!).  I lubed up my cock first, having read not too long ago that doing so would enhance the pleasure for me and make it feel like I wasn't covered.  Then I slipped on the condom (wow, I hadn't done this in nearly six months!), and then lubed both of us up.

I entered her missionary.  She spread her legs very wide, and lifted them high over my head, holding them with her hands, so I could go deeper.  She felt so great, and the shit I read about lubing inside the condom?  Yeah, it worked.

We played in lots of different positions, including reverse-cowgirl.  I did that once or twice with Jade, but it never felt quite right.  Sam knew had to do this perfectly, and she rode me pretty aggressively, twerking like Rihanna.  It was fun; I spanked her tight ass, and guided her up and down on my pole.  Then she turned around and rode me face to face.  At this point I noticed that she and I were both sweating from this workout.  She had a faint body odor of real workout sweat, and I have to say that I loved it!  Nothing sexier to me than a woman who smells a little bit when she's fucking.  Hayden never had a smell, Lola smelled weird, and Jade smelled sour.  With Sam, it was perfect, and it turned me on.  I kissed her, sucked those luscious tits, and grabbed that ass before exploding inside her.

Sam told me later that she'd had two orgasms, but I couldn't tell when (and frankly, she couldn't tell me either, which makes me a little suspicious).  I'd say overall that she was way up there in terms of beauty and sexiness, but we have a few things to sort out in bed.  I do like that she was not shy, either about her body or her sexuality.  She was giving, fun, playful, and goofy.  Very much like me.  I'd like to see her a little more expressive of how she wants things, rather than letting me take the lead, but that can come with time and communication.

We talked for a long time afterward, about a lot of things.  She then showered up (another thing I liked -- no getting dressed all smelly and then leaving) and took off a few minutes later.  We had almost two hours together, and were sexual for about an hour of that time.  I was very happy with that.  After she left, I cleaned up, got dressed, and left.  We'll use this hotel again, and we can't wait to see each other again.  Definitely a great girl.

Wednesday, July 24, 2013

Today is Fuck Day

I leave in about half an hour to meet Sam for our first "date."  I am actually a little nervous today.  I think she's just stunningly beautiful, and could possibly be more beautiful than Hayden.  I need to see her naked first.

Meanwhile, a new girl named Rocky wants to meet. She has her own place (a big plus), is a little older (26), and is a working actress (well, maybe not so much since she wants $1,000 a month of my money).  I'm still open to meeting new girls, as a hedge against the potential for Sam and I not to hit it off in bed.  I'm still a little surprised that after getting $3,000-$6,000 a month she'll take my offer.

Updates later.

Tuesday, July 23, 2013

This is Gonna Be Good

Quick text exchange between Sam and me today:

Me: Are you clear on the hotel for tomorrow?

Sam: Yes! :-)

Me: Awesome. See you at 3 or so.  I'm clear till 5:30 or 6

Sam: Perfect

Me: Can you think of a better way for us to get to know each other?

Sam: LOL, I can't!


Monday, July 22, 2013

Stressful Weekend

God, this past weekend was packed with so much family stuff, I pretty much OD'd on it.  I had so little time to hang out.

DW and I took a class the other night on an advanced sexual technique.  Believe it or not, this was her idea.  She was tired of not caring about being non-sexual, and she saw that it was damaging to our marriage.  Better late, I guess, right?

Anyway, I was eagerly anticipating this class, but she was nervous and apprehensive.  She had no idea what to expect, but she at least said that she was going to be open to it.

The class was filled with couples and singles (or halves of couples) trying to gain a new perspective on their sexualities or their relationship.  The woman who led it was gorgeous and her face was lit up like a newborn baby's face.  The two hours was spent doing a bunch of guided exercises designed to get us in touch with physical sensations and to get us rooted in the present moment.

I had a great time, and saw the possibilities, not only for us as a couple but for me within my sugar relationships.  But I wanted to give DW the lead on this before I let her know what I thought.  She was ambivalent, not convinced it was for her, and not sure if she wanted to continue the practice.  She was, however, willing to try the exercises at home.  The conversation returned to her sexual desire (or lack of it), and it was pretty clear after five years of this marital crisis that she still gained no physical or emotional pleasure from anything sexual, either with me or with herself.  I told her that it was new to me that even penetration with me wasn't pleasant for her (she even said it hurt).  She no longer liked oral sex, which used to give her orgasms every time, she didn't want to be touched almost anywhere.  That is her current reality.

"So," I asked, very concerned and coming from love and respect, "would you prefer it if I didn't make sexual overtures anymore?"  She said she didn't know.  She likes it when I reach out and snuggle with her in bed, but she didn't want me to touch her breasts anymore.  I said that was my signal that I wanted sex from her, but since she didn't like it, what suggestion would she make for me to let her know I wanted sex?  "How about you whisper in my ear that you really want to make love to me?"  I took that in; let's give it some time and see how it develops.  I did make clear what I wanted: I wanted a wife who adores me, who finds me irresistibly attractive, who can't keep her hands off me, and who still sees me as her champion.  "I'm not that woman today, babe," she said, "that's just not me right now."  Whether that will ever be her to any degree is another story.  I'm just grateful that I have the sugar life as an outlet.

Sam and I are on for Wednesday.  We'll see how things go.

Friday, July 19, 2013

Breaking the Rules (And Fixing Them)

I posted earlier this week that Naira had sucked my dick on the first day we met, and had updated the post to relate that I had broken one of my rules about having sex with DW and another woman within the same 24 hour period.  The rule was set up to honor my marriage to DW and not have my cock inside her within 24 hours of having had it inside another. 

At first I felt pretty bad about this, and felt guilty for not having had the presence of mind to stick to my rules.  I felt out of honor, in other words.  But, in this particular instance, I'd had oral sex with Naira after having had sex with DW.  I see that a bit differently than if Naira had given me the BJ before having sex with DW.  As it was, I wasn't dishonoring the relationship at all if the sex was after DW.

Putting a 24-hour buffer before and after sex with DW seemed like overkill to me.  So I am going to amend the rule: no sex with DW within 24 hours of having sex with another woman. So, I can put a buffer around sex with Sam instead of DW.  If , in the rare instance I have sex with DW the day after having sex with Sam, and then DW wants to have sex with me on the same day, I have to put off sex with DW for one day.  That seems more appropriate.


Down to One Girl

Now that I've selected Sam as my new mistress, I had to let everyone else go.  Yesterday, I said goodbye to Naira, K-bear, and Je, and today I was left with Arabia and Aura.

I sent them each the same text message: "Hi, long text...keeping things real: I met a girl yesterday who I really like and I'm going to go with her.  You're amazing, bright and beautiful, and I really like you too.  You didn't make this an easy decision, please believe that.  I'm holding onto your number in case circumstances change, and I'd like to contact you again if you're still available."

Arabia has not responded, but Aura was gracious enough to thank me for my honesty.  But, she said, she didn't like being someone's second choice.  I asked her the following: "You know, we liked each other and we've had some nice chats.  If I texted you in a week, or two weeks, or six months, and you were not involved in an arrangement, and I said "No looking around, I want you," would you say no?"  Her response?  "I'm not sure."  So I said, "Let's just cross that bridge if/when we get there, OK?"

I'm disappointed that Arabia didn't have anything to say.  She was a great girl, but I think she might have paid the price for being the first girl.  I tried to circle back with her a couple of times, but she wanted allowance money to see me again.  That hurt her chances with me, but I was open to that.

Anyway, I spoke today with Sam and opened up a little about the kind of guy I am.  I said that, while I wasn't the type of guy to leave 15 text messages and a handful of voice mails if I wasn't hearing from her, she needed to know that, in the beginning of the relationship, I tend to be a little nutty about confirming dates and such.  Just until trust is developed.  It's nothing personal, just my shit, and I promised to be gracious and gentlemanly about it.  She appreciated my telling her.

On to our first date.  Great weekend everyone!

Thursday, July 18, 2013

Sam

Let me start by saying that I wanted Sam to be the one.  From the day I first saw her pictures, I wanted her to be the one.  Today, I put that wish to the test.

We met late this afternoon at a coffee shop at the beach.  I walked in and there she was, her tan and toned body in a peach silk top and white shorts, with a pair of wedge shoes on her very cute feet.  She had long, straight, dark brown hair that reached well past her shoulders.  I gave her a little wave as she looked up from her phone. She gave me a very warm smile.  Oh yeah, this is gonna be good.  In her purse, she was carrying a tiny little puppy that could have fit in my two hands.  She was an eight-week-old chihuahua/dachshund mix, and didn't have all her shots yet, so she couldn't even be put on the ground.

Sam is in her mid-twenties, stands about 5'4" and I would say is a solid size 2-4.  She looks like she's in great shape, although we didn't talk about her exercise.  I can't tell if her breasts are enhanced, but this former swimsuit model could very well be enhanced.

The coffee shop was crowded, and both of us were at parking meters running out of time.  I said, "I'm going to buy us a couple of bottles of water.  Then let's get out of here.  I only had one quarter for the meter and need some more change."  She agreed and we took off.

We walked back to where my car was parked, about a block or so away.  I fed the meter and rejoined her, and we walked to the beach to talk.  During the walk, we talked about her business.  Sam works with animals (hence the puppy).  She had been at it for nearly four years, but has been working with animals since childhood.

We also talked about where she lived.  See, Sam lives in my Socal hometown.   She and I also graduated from the same high school (just a couple of decades or so apart).  She lives with an elderly relative, and wants the arrangement money to help her move back out on her own again.  Apparently, her business isn't very profitable.  But she loves what she does and she plans to turn it into a successful business.  I really, really liked how enterprising she was.  She had great ideas on how to grow her business, and she discussed all the barter relationships she'd developed with ancillary service providers to help her manage her costs.

We found a bench to sit down on and talk, and she took the pup out of her purse so she could get some air.  It was at this point that I asked her what her history was with the sugar life.  She'd only had one relationship which lasted about two years.  The guy was single, and while it started out as sugar, it veered into relationship territory.  The guy got a little too needy; would text her 15 times if he didn't hear back from her within five minutes.  I took that note very carefully; I tend to follow with one or two texts after the initial contact if I don't hear.  I intend to ask her if phone calls are better (and does she return them?).

We reached the topic of money.  Here's where things could have gotten a bit awkward.  I actually thought we'd talked about money already, but we hadn't.  I guess there are just too many girls on my radar at the moment!  I asked her what kind of financial arrangement she'd had before.  The guy gave her anywhere from $3,000 to $6,000 a month, and they saw each other up to three times a week.  "So, he was more than a boyfriend, huh?"  "Yeah, he took pretty good care of me," she said. "But I'm totally open to any kind of arrangement.  I explained my terms, and, to my great delight, she was OK with them.  I mentioned to her that my last three-year relationship ended because of a boyfriend in the picture, and I wanted no more of significant relationships, including boyfriends, fiancees, husbands, or even children.  She agreed and said that if she were dating anyone she'd tell me if it got serious.  We were definitely on track.  I liked this girl a lot, she was ridiculously beautiful, and very easy to talk to.  She said, "You texted that you were 'shockingly handsome,' and you were right.  I was so glad.  When you walked into the coffee shop, I was like, 'Yes!'"   Major ego boost.

"So, Sam, I think I'm done looking.  Do you want to give this a try?"  "Absolutely," she said.

Sam is my new mistress.  We had to cut it short because she had a business meeting and the meters were running out, but we had a great time together.  A quick hug and peck on the lips, and we parted ways.

Over the next hour or so, we traded a few texts back and forth to set some sexual ground rules.  No anal, oral was great, and 100% protection, all the time.  Everything else would come organically.  I didn't want to have a heavy sexual text conversation with her.  In this case, I felt at ease with her enough to let the sexual connection come out.  The deal breakers were out of the way, and so we would be fine.

During the evening, I let Naira, Je, K-bear, and a couple of other girls about whom I hadn't written know that I was done looking and had found the girl I wanted today.  I thanked them for meeting with me and I let them all know that, should my circumstances change in the future, I'd keep their numbers handy to contact them again.  No one objected, and all of them were gracious.

Next come Aura and Arabia.  I am not looking forward to breaking the news to either of them.  Both of them tried really hard to get my attention, and had Sam and I not connected so well, I'd have chosen one of them, for sure.  I think I'll be just as straightforward with them as I was with the other girls, and hopefully it won't be a problem.

Sam and I are meeting next Wednesday for our first date.  I haven't been this excited about a new girl since, well, Dale I think.  Keeping my fingers crossed.


Sam: a Preview

The pics of Sam she posted on the sugar daddy website are incredible.  Check these out (edited to remove her face):





I'm not kidding when I say that I want her to be my girlfriend/mistress/lover, if based solely on her body and face.  But obviously, her personality and attention to our arrangement will come into play as well.  And today, in just 90 minutes, I'll be meeting her at a coffee shop, for a chance to decide whether Arabia, Aura, K-bear, Naira and the rest are pale imitations of this girl.  I know I'm probably putting her on a pedestal, but for now, that's OK.  I think I'm present enough to know when she doesn't deserve to be on it.

Will update more later.

Wednesday, July 17, 2013

Aura Moves UP

I had thought I was going to dismiss Aura from my list, but recently she's been showing signs of strength.  The fact that she's a competitive athlete might account for her working really hard to win me over.

She texted me on Monday to wish me a good morning.  This was a follow up to my note to her last Friday that I appreciated her reaching out to me.  "Goes a long way" with me, I told her.  She got the message, apparently.

I texted back that I was a bit under the weather but I was planning to get more sleep and drink more water.  'The pic of your amazing butt doesn't hurt either lol."

Her: Which one?
Me: The one you sent me that goes with your profile pic
Her: Oh, don't recall
I sent her the picture.
Me: You got anything better
Her: Ohhh.  (She sends another picture of her, on her knees, naked, with her ass facing the mirror so she could photograph herself)
Me: Wow.  When did you take that?
Her: A week ago
Me: Beautiful.  Any others?  I'm thoroughly horny now.
Her: Thx.  I'll have to find some.  I try not to keep them on my phone
Me: If I weren't in my office...
Her: LOL.  I'm free later this week!
Me: I'm sure...

Yesterday she sent me another of her naked.  This time she was facing the mirror at an angle, her hair covering her breasts.  Unbelievable body.  But I've seen her up close and while she's curvy, I'm not sure I want to fuck her.  If Sam turns out not to be a good pick, Aura will be my #2.

Naira Goes Down

The past weekend saw me spending the vast majority of my time with DW and the kids, with some birthdays to celebrate, some relatives to see, and some great food to BBQ.  I'm an excellent grill cook, by the way; I've become quite adept at it!

On Monday, Naira and I were scheduled to meet for the first time.  That morning I sent her a text: "Do you ever make out on the first date?"  She said she did, so I texted, "Maybe we'll have to find a place to make out.  My office is right up the street; a three-minute drive from where we're meeting."  She said, "Ok, that's close."

So I had permission to put moves on her, but I wasn't going to pressure her to go beyond kissing.

On most days, my office suite is empty except for me.  Occasionally someone will spend a few hours at work, but usually everyone is gone before 5 pm.  As my date with her was at 4, I packed up 15 minutes early and made my way to the door.  There was only one co-worker left in the suite, and he said he was leaving in 10 minutes.  Great, I thought, I'll have the suite alone to myself when we come back.

Naira was much cuter in person than in her pictures.  She's Creole, has very light skin (which, honestly, could stand a little attention), and a great thin figure.  It was clear that her bra was padding a very small chest, but I never put much value on big tits.  She wore jeans that hugged her narrow hips, and she had a cute round ass that I wanted to get my hands on.

We ordered our drinks at the coffee shop and sat in the quietest corner in the place.  Not much in the way of a conversationalist, but so much had already been discussed over the phone and by text that there wasn't much else to say.  She did reveal that she didn't have a social media profile online.  She didn't like people knowing her business and she much preferred direct contact with people.  She also worked as a hostess, part time, at a restaurant near my house.  It was a restaurant that I wanted to take my family too, so I warned her that I might show up for dinner while she was working there and not to be weird about it.  She said she'd be cool.

We managed to waste an hour at the coffee shop, and I asked if she wanted to come to my office up the street.  She agreed.  She met me in the lobby of the building, but I pretended not to know her and made my way to the elevator.  She got in behind me and we went to my office.  As I predicted, the suite was empty.  She excused herself to use the restroom and came back a few minutes later.  I cleared my desk and straightened up a bit, and when she came back, we started kissing after a few minutes.  Soft lips, a good kisser.  Not much tongue, but that was OK.  I started feeling her tits, reaching around and grabbing her ass.  She didn't resist anything.  I guess she knew something was going to happen.  I put her hand on my already hard cock, and she stroked it through my jeans.  After a minute of kissing standing up, I laid her down on my desk and got on top of her.  I unbuttoned her blouse, undid her bra, and started sucking on her hard, dark nipples.  So cute!  She was sweating a little, and had an acrid smell to her, but it didn't deter me at all.

We stood up and I started undoing her jeans, but stopped just after the first button.  Whoa -- I felt stubble at her belt line. Very coarse stubble.  I was slightly turned off, but not put off.  I asked if she wanted to fuck.  She said, "I didn't come prepared, and I'm on the last day of my period."  Aww, I said, would she suck me off?  After a few minutes of thinking about it, she agreed, but she wanted her allowance.  We'd agreed on $400, but I had exactly $20 on me.  I told her I'd hit the ATM in the lobby once we were done, but that I'd only be able to get $300.  The rest would be when we saw each other again.  She said that, because I couldn't fuck her, I would have to give her more than the $100 next time.  Cool, I thought.

She was the first girl I'd ever met, other than Mary J, who never made any comment about the size of my cock.  Is it a coincidence that both girls were black?

She gave a very good blow job, and I came in about ten minutes, unloading in her mouth. She said it was the first time she'd let a guy "nut in my mouth.  It wasn't that big a deal!" she commented.

After a few minutes of letting my cock return to normal, I went downstairs, got her money and came back up.  I tried to handle it non-chalantly, but I had to hand the money directly to her.  Wasn't my best moment.

We rode down the elevator together, and I kissed her goodbye in there.  Once we left the elevator I moved on alone to my car and she to hers.  We exchanged a smile as we parted company.

I don't think she's the one.  She's not very bright, although she is cute and a little sexy thing.  She'd take less money, but I'm not hung up on that.  But I'm still feeling like Arabia is the one so far, and Sam is #2.  I've decided that K-bear is a no-go at all. Geographically challenging and I don't want to have two Asian girls in a row.  I canceled our meeting scheduled for today and didn't hint that we'd reschedule.  She was disappointed, but I'm not caring that much.

More later...

UPDATE 7/19/2013

In having Naira suck my dick on Monday, I realize now that I broke one of my major rules.  Because DW and I had sex on Sunday night, that means I had my cock serviced by another woman within 24 hours of being with my wife.  A post on this is ahead...

Tuesday, July 16, 2013

A Cautionary Tale

I have so much to go over since my last post.  Let's start with...


















Say hello to "Ana."  Would you look at that face?  This is the face that launched a thousand "Oh, Shit"s.  Actually, is 84.61 Oh Shits to be exact.

Now, I'm not one to show faces on this blog for any reason, but you will soon understand why I made an exception in this case.

Now, I put the name "Ana" in quotation marks for two reasons, both of which will become obvious as you read my story.

I first contacted "Ana" last Thursday based on this beautiful face, and the rest of the profile.  "Ana" was late twenties, petite, Latina, and a behavioral therapist.  AND, she was asking for less than $1,000 a month for an allowance.  She was just about perfect.  Petite girls, however, can't handle my large cock, so I've gravitated to taller girls since Hayden.  I also didn't at the time think anything of the fact that a behavioral therapist needed the supplemental cash that came with a sugar relationship; every woman has her own reasons and her own story.  Anyway, my opening note complimented her face and I left her my cell phone number to receive a text or call.

The next day around 5:00 pm I got a text: "Hi Porter, it's Ana."  I was thrilled to hear back from Ana, so I dropped everything I was doing and returned her message.  She was personable and sweet, and very articulate.  So far, so good.  We were flirty.  Also good.  I asked her to call me. Her reply: "Well, my phone got turned off and I'm using my friend's wifi right now."  I wasn't clear what she meant by this.  Was she using her friend's phone to text me?  And again, the idea of her phone getting turned off was not all that unusual to me.  So many women I've met have some financial need, whether it's immediate or long-term.

We chatted a bit more, and we decided that we'd meet the next day at a place we both knew.  She lived near my office; perfect!  Then I asked when she'd be able to call me.  She repeated that her phone was turned off, and that she was trying to earn money to get it turned back on.  This particular night, she was babysitting for a friend.  Now, she was a pediatric behavioral therapist, or so she said, so I had no issue with her taking care of children.  But I was puzzled, and I asked.  "Babysitting?  Is your patient load down?"  It wasn't, she said, but she only gets paid every month and she had already gotten her check this month.  So her money was already gone, which meant that she was not very fiscally responsible.  This was a red flag to me.

I asked her to send me more pictures.  She said they were all on her cell phone, but she said she'd see what she could find and would email it to me.  I gave her my email address.  When I got it, there was a picture of a dark skinned Latina, lounging on a sauna bench wearing a black bikini.  Amazing picture.  At this point I also got her last name, which was appropriate Latina.

As there wasn't much more to say at this point, I said I'd talk to her later and looked forward to meeting her.  She said that she wanted to know if I'd be OK with helping her get her cell phone turned back on so that she could send me more, presumably racier, pictures.  I asked her how much she needed to get her cell phone turned back on.  "$84.61," she said.  Is that all?  I said.  Sure, I'll give you $100 up front and the rest on our first hook up date.

Then something made me text further: "Just wanted to clarify: I will give you $100 when we meet and the rest when we meet for sex.  Is that OK?"  She then said that she really needed it right away; could I use Western Union?

Now, at this point, I hadn't fully freaked out, but I was feeling some uneasiness about it.  I'd never used Western Union before, and I was not in a place at my home to send her a WU transmission of money.  I suggested she let me pay her cell phone bill directly.  She said she thought that "might be OK," but it would be easier to use WU.  I said, "I don't really know you.  There are scam artists all over the Sugar Daddy site.  Not implying anything, but at this point I'm not feeling all that comfortable."  "Understood," she replied, "I'll figure something out hun. No worries."

I hadn't yet deduced that this was a total scam, and she seemed so nice about it; I wanted to help her.  It wasn't a huge amount of money, so if it did turn out to be a scam, it wouldn't be that bad.  Still, I wanted to try one more time to see if she could prove who she was.  "Here's what I need: take a picture of yourself using your iPod Touch, holding a piece of paper with today's date on it.  Then email it to me.  If your face matches the one in your profile, I'll send you the money."  She said she didn't have a camera on  her iPod since it was an older model, but her friend's laptop had a webcam.  She said she would go for it and send it to me right away.

Forty-five minutes later, no picture.  As it was then 11 pm, I texted, "I'm done.  Going to bed.  If you send me the pic overnight, I'll handle it in the morning."  Never heard back from her.  So, Monday morning, I went to the Sugar Daddy site and reported her profile to the administrator as someone who had tried to scam me.  As of today, the profile is still up and active, so who knows if I got it wrong?  Even if I did get it wrong, let this be a lesson to anyone, SD or SB: do not ever attempt to start off a sugar relationship by asking for cash before either of you has ever met face to face.  It's a recipe for creating distrust and suspicion.  If you need money that badly, go pawn something, ask your best friend whose kids you're babysitting, or turn a trick or two.  But an ongoing mutually beneficial arrangement does not begin this way.

Friday, July 12, 2013

Naira Crosses the Threshold, Then Goes Back Again

I've written before about Naira and shown a pic of her amazing body. Yesterday, she crossed the threshold, from someone I was only considering as a one-time hook-up, to someone I'd actually think about seeing on a continuing basis.  Honestly, it was because she accepted less money than everyone else did, but also because she seemed excited about meeting me.

I was supposed to meet Sam today, but she texted me yesterday when I tried to confirm that she needed to reschedule.  Seems she was supposed to be driving up north tonight to attend a funeral, but the people with whom she was traveling decided to leave at 6 am instead of 6 pm.  No worries, I told her, but I wanted to confirm that she'd be available early next week.  "One hundred percent yes," came the reply.  So, whenever I get that strong a commitment, I'm always in doubt.  Nothing is 100% yes.  I'll just take it as it comes.

Because my plans with Sam fell through, I decided to proposition Naira about meeting today for an actual hook-up.  With that body, who wants to wait?  She agreed, even when I told her that the hotel I usually use had raised their rates and that I'd have to give her less than we agreed on.  She was fine with it, so now she became even more appealing to me!

Then, an interesting thing happened to me.  I held off booking the room; I didn't really know why and I had no funny feeling about it, but I just didn't book the room.  And last night, Naira sent me a text that sparked a whole conversation.  Here's how it went:

Me: Be ready (to play)
Her: I will...Are you excited?  I am ... lol
Me: Oh, yes.  I always love it when I fuck a new girl.  Having you on top of me (her fave position) will be awesome.  I love fucking that way.
Her: Lol oh ok...
Me: you seem a little nervous though...
Her: You meet girls on the site just to fuck them?
Me: not really sure what you mean.  These arrangements are my sexual outlet.  I like meeting new women, but my intent is to fuck them.  If you don't want to have this adventure with me tell me now
Her: Oh ok, so does it always go as planned?

At this point, I dialed her number and we talked instead of texted.  I asked her what she meant by her last text.  She was sort of wanting to know if I'd ever been stood up before, if a girl had committed to meeting me for sex but then backed out.  I said that once a hotel room was booked, I had never had a girl cancel on me, but one girl (Hayden) had canceled three dates in a row at her apartment at the last minute. 

Even having this kind of discussion put me in a very wary mood.  So, I knew what I had to do.  "Listen, Naira," I said, "I usually don't meet girls for sex on the first day.  You had turned me on with your pictures, and I didn't want to wait, but I want you to know that I'm totally OK with meeting non-sexually at first.  In fact, I prefer it.  So let's just call off tomorrow as a sex date, and we'll text each other later to plan something, OK?"   She tried to convince me that she wasn't nervous about meeting me for sex, but I wasn't having any of it.  Any girl who brings up something like being stood up the day before a meeting is hedging her bets in case she chickens out.  So, the conversation ended on a decent note and she was more comfortable meeting for coffee today.  She doesn't live far from me, so I can pick somewhere neutral and we can meet.  I'm thinking the same coffee shop near my office where I've already met Arabia, Gia, and Annette.  They're going to think I'm interviewing girls for a job.  And they'd be right!

I will say, however, that Naira's standing went from #2 to #5 very quickly.

Here is where things stand with me:
#1 - Arabia
#2 - Sam (until we meet)
#3 - K-bear (until we meet)
#4 - Je (I'll go into our first discussion later)
#5 - Naira
#6 - Tee (haven't met yet)

Thursday, July 11, 2013

She Was Not Kidding About "Average"

Honestly, I should have taken Annette at her word when she said she had an average body.  Normally, in online dating-speak, "average" usually means fat, and "a few extra pounds" means really fat, and "heavy" and "BBW" mean obese. I guess, however, that body image is completely subjective. In short, however, I was not at all attracted to her.

As I wrote earlier, Annette has a stunningly beautiful face, and if her body had matched her face, this would be a much different post. I still would have passed on her, however, because in reality, she has zero personality. Her terse and non-revealing text messages really did mirror how she was in real life.  Our meeting lasted only 30 minutes because really she did not have much to say. 

I think I've written way too much about this already, so I'm going to end this post here.  Moving on...


For Someone Who Wants to "Retire,"...

... I'm sure acting like someone who has no intention to retire, aren't I?

Annette and I are confirmed for later today.  Very excited about meeting her and seeing if the bod matches the face.  That face!  So beautiful.

I also wrote a couple of days ago about Naira, the African-American girl with the great body and pretty face.  I wrote her off as too "city" for me.  Basically, she's not a very articulate girl, but she is definitely sweet.  She has been texting me body shots, and I'm pretty hooked.  I want to meet her for sure.



How can I resist that?  Right?

I also sent an email to Sandra, about whom I wrote a very terse "too young" comment the other day. I let her down easy, and even said that I'd be down for a short-term thing (like once or twice) if she wanted, but that I was just more comfortable long-term with someone older.  No response yet, but will update if needed.


Wednesday, July 10, 2013

More Updates

Aura was not the one, unfortunately.  Even though she had a slamming body in her pictures, and even though she claimed to be curvy and girly where it counted, I didn't agree once we'd met face-to-face.

I found her muscular body to be very masculine.  Did I tell you she worked out doing Olympic-style weightlifting and women's rugby?   Like most women who exercise at that level, she lost a lot in her chest, and didn't feel curvy to me at all when we hugged.  It was like hugging a man.

Also, her face was chiseled and masculine as well.  Teeth somewhat crooked, nails cut short.  She was wearing short shorts and she had very shapely legs and a pretty nice ass, but she just didn't do it for me.  We were together for an hour, and even though I knew in 10 seconds that she and I would not work out, I think it's a bit rude to bail right away.

Besides, there were a few moments during our conversation where we laughed together.  But she was a pretty serious girl, and I could tell she was in a pretty funky place in her life.  She was a nursing student, and she had been going to a private college, but could no longer afford it and had to transfer to a state school.  She also had to move back in with her mother.  She busied herself with fitness and training and studying to take her mind off things.  At the end, I walked her to her car and gave her a hug and a kiss on the cheek.  She did not reciprocate.

A little more on Gia, which I neglected to discuss. Again, I saw her walking up and I decided right away that she would not be the one.  She was cute, but in a plain-Jane sort of way that just didn't light me up.  Blue eyes, a cute nose and smile.  She had a tat around her left bicep and another behind her left ear, both of which she said were meaningful to her.  Her boobs were small and I could tell she wore a very padded bra.  Her profile pics were similar to what she was in real life, but she was very sweet.  She even told me that I was much cuter in person than in the pictures.  She had a lot of things to say about Persian men at the outset; apparently they really turned her off, and she actually thought I might be Persian because my hair looked darker in my profile pic (it was two years ago, so yeah), and it is styled in a sort of hip fashion.  It felt nice to hear.  At the end I walked her to her car and we had a quick little peck on the lips and a hug.  I'll let her know next week that it's a no.

Arabia is right back in the race now.  We were texting a little bit this afternoon.  I told her I'd been thinking about her, and she replied that she had been doing the same.  I asked her to elaborate, but I didn't get a reply.  So I followed up by asking her if she wanted me to go first.  She replied that her battery was nearly dead and would be before she got home, but yes, she wanted a surprise message once she plugged back in.  I wrote, "I've been thinking about meeting you at a quiet hotel, where I peel your dress off of you, get down between your legs, and lick you till you explode all over my face."  About an hour or so later, she wrote back that she really liked that.  Then I asked her to tell me what she'd been thinking.  Of course, I expected an oral sex reply: "I want to suck the cum from your dick."  Uh, yeah!  Very high marks for creativity, plus her acknowledgment that she loved cum.  I then told her I wanted to see some of her modeling shots.  She sent over three that featured her very ample breasts.  I really like the way she looks!  In all fairness, however, she really does look a lot like Hayden, so that may be a big reason why I find her so appealing.

Tomorrow I have coffee with a new girl named Annette.  She's a midwestern girl, about 26 years old, 5'6" with what she says is an average body.  She lives near my office, not far from where Wanda used to live.  Her pictures don't really give her away, but she sent me another pic of her face.  I have to say that she has the prettiest face of all the girls I've contacted so far.  Her eyes just melt me, and she appears to have a fantastic body.  Tomorrow will tell.  The physical attraction really needs to be matched by my attraction to her as a person, though, and her brief texts haven't given much away in the realm of personality.  Keeping my fingers crossed.

Friday I meet with Sam.  I already like her a lot, but she's got a geographic challenge being 30 miles away.  I'll hold off till we meet, but something tells me that she'll have to blow me away in all respects to make the final cut.

Back on the Market Update

Today, I had lunch with Gia -- cute, and definitely seems to be on the same page as me sexually, but no go.  She doesn't have that explosive spark that gets me going.

Sandra -- Sent me pics of her body and she has unbelievable tits.  Love Latinas, but still too young.

Naira -- African-American girl who responded to my profile.  We talked on the phone for half an hour last night.  She's a bit too city for me.  She's got an amazing smile, great eyes, beautiful body. But I'm not totally fond of black girls.  Just a personal preference, of course.  Probably a no.

K-bear -- Set up a meeting next Wed in her neighborhood at a local Asian shopping mall.  She's cute, she loves sex, especially oral, so she's a possible.

Sam -- meeting her tomorrow in her town about an hour away.  She's a dog lover which I like.  She's actually three years younger than her profile says.  First time I ever heard of a woman lying that she was older than she was.  Dangerous body.  We talked today on the phone right after she'd woken up about 8:15 am.  Loved her first thing in the morning voice.  Major turn on; made me imagine what it would be like to wake up next to her.

Tee -- Belizean princess, mid-twenties, African roots.  Very cute, lived in this country four years.  I'm very interested in her.

Arabia -- falling off the radar at this point, as I think there are some cuter girls, but I'm keeping in touch with her just in case.

More later.  Going to meet Aura now.

Tuesday, July 9, 2013

Back on the Market...

So, now that my arrangement and relationship with Jade were over, it was time to do some serious looking around.  On the SD website, there were plenty of girls.  My profile had to be updated, so the website administrator blocks the profile for 24 hours while they review it for inappropriate content.  They're really trying to avoid solicitations/nudity, escorts, and the like.

I sent out a bunch of intro messages.  Here a few highlights of the girls I contacted:

Joni(!): She was still in the market.  I fucked Joni last year and got the best blow job ever.  The note I sent said that I'd overcome the emotional needs that turned her off, and wanted to try again.  No response.

Lola(!): She was back on the market, but hadn't been on the site for over two weeks.  She never picked up the message.

Sam: mid-twenties, a dog lover, student and volunteer.  Extremely cute girl next door, with some very dangerous curves.  We have texted with each other since the first day, and we'll be meeting later this week.  Good chemistry so far.

Aura: mid-20's lives about 10 minutes from my house with roommate.  She's an avid workout fanatic, and her pictures reveal a very muscular body.  She says that she's still soft and curvy.  Not sure of her ethnicity yet, but I'm not totally feeling the vibe just yet.  Texts have been kinda cool.

Sandra: very young, early twenties, and aggressively trying to win me over.  Sent over some nice photos.  I'm not going there, although her Latina looks are very nice.

K-bear: Asian, mid-twenties, cute face, probably Korean.  Just exchanged a couple of messages so far.  Hoping for more.  We'll see.

Je: A French girl who lives near the beach.  Her pics have been inconsistent, and her body shot (which she says was a couple of years old) showed that she might be heavy.

Gia: Blond, college student, mid-twenties.  Not sure of her face, but her body is slamming.  Meeting her this week.  Nice chemistry so far.

Mandy: Redhead, flight attendant, blue eyes, late twenties, and very cute.  Her job keeps her traveling a lot, but we might make some time next week.  So far all I've seen are face pics.

Arabia: This is the only girl I've met so far.  She's mid-twenties, 5'8", dark hair, dark eyes, dark complexion.  Middle Eastern and Western Euro.  Full time model.  I know, shades of the lovely Hayden, right?  This was exactly why I wanted to meet her.  We got together at a local cafe, where she got a chai and I ordered carrot juice.  We sat in a quiet corner on their enclosed patio.  She wore a very short horizontal striped dress that was pretty open in the back to reveal a very large tat.  Not attractive at all, I must say, but she was cute.  Had a little hoop in her left nostril.  Nice chest too.  She told me later that they were enhanced but very soft.  Kind of like Jade's, I guess.  We talked and came to terms over an arrangement and discussed a few relationship things.  Definitely an NSA deal.  She lives in her own apartment so that's a good thing too.  On the pill.  Awesome!  Maybe some bareback action in our future.  One thing was that she was definitely not as pretty as Hayden, although she was very cute.  We kissed goodbye and had a nice hug, and texted each other later.  Definitely some chemistry going.

All this writing about various girls reminds of that old tune by the Nails, "88 Lines about 44 Women." 



No More Jade

As I'd written last week, I wasn't exactly sure if I was going to fully retire or find a new girl, but I was pretty sure that I was done with Jade. 

Last week I paid up and upgraded my membership again to the SD website.  I also amended my search criteria to change the age range.  I'd had two different search criteria: one was 22-37, and the other was 18-30.  I got rid of the second one and added a new one, this time with the age range 23-40.  This is in keeping with my rule that I not date anyone younger than 23.

My search results were astounding.  Fully over 1,800 girls fit the description.  Of course, you narrow that down to the first few pages, since I sorted my search according to how recently they'd last logged in.

On my third page of results, 41-60, I spotted Jade's profile.  I wrote back in February that Jade had told me at our first meeting that she was pulling down her profile now that we were going to be together.  The last login date for her was the day after our last date.  Well, I guess she hadn't pulled down her profile and was now looking for someone.

I sorted through my feelings.  On the one hand, I was pretty much done, and the fact that she was also looking confirmed it for me.  On the other hand, I was really bothered by the fact that she'd lied to me.  I guess finding out that someone has lied to me bothers me so much because it brings up the fact that I'm far from Honest Abe 100% of the time.  So I'm getting a dose of my own medicine, in a way.

I didn't need to have a big discussion with Jade about her lying to me; I could process those feelings on my own.  But I had to end the arrangement right away.  Since it was late afternoon and I was getting ready to head home from work, "right away" meant the next day.

I waited until after 9 am, then I began with a text:

Me: "Hey, I wanna tell you something and not have it be a really big deal.  Is that OK?"

Jade (about 30 minutes later): "Sure?"

Me: I've been thinking that it might be time for us to move on, so I went back on the SD website to have a look around.  I saw your profile in my search results, and it showed that you went on the site on the day after our last date.  I'm assuming that you've been on more often than just that day.  I guess we're on the same page then."

Jade: "Yeah, I go on and off.  It's OK.  Good luck."

Me: "Best of luck to you too."

There were a couple of texts over the next couple of days that revolved around wanting to keep things amicable.  I asked if she was OK, to which she replied and asked the same of me.  I told her that I was actually a little sad, which was true.  She wrote, "Why sad?  We can still get together.  We can still fuck each other."  I didn't see that for a few minutes, but when I did, I was surprised and I wrote, "Really?  Why would you want to get together for sex without a financial arrangement?"  See, she was still hoping to get money!  "Who said anything about that?" she asked. "We met on a financial arrangement website."  A few seconds later, she wrote, "Oh, never mind.  Thanks.  Good luck."

And that was that.  I'm actually very happy that things are over between us.  I think the lesson here for me is that boredom should not be ignored, and trust can never be complete with a girl in these relationships.


Wednesday, July 3, 2013

Winding Down

Today Jade and I got together at our usual hotel.  She showed up just a few minutes late.  However, she then proceeded to tell me that she was feeling sick.  No kissing, no oral, she said.  Just fucking.

I didn't object too much.  We had a good time, she came twice and I unloaded on her chest and tummy.  But after about an hour together she then announces that she needs to leave because she had a meeting.   I wasn't all that happy about that, and let her know I was "disappointed."  She took off, I showered and then headed home.

I'm sort of feeling that this might be a good stopping point for me. Either that, or I'm ready for the next girl.  I haven't figured that one out yet.