Friday, January 31, 2014

Star, and the Week in Review

So, I didn't get to see Leah, I had a casual date only with Belle, and today was my day with Star.

Star showed up to our date, at a trendy 24-hour coffee shop near the beach, about 10 minutes late.  She was about 5'7", had long dark hair, wore big dark sunglasses, and was wearing very casual clothes.  She looked slightly heavy, and I was a little disappointed in that, but she had great tits (fake) and a cute smile (perfect teeth), so I went with it and decided to see where the meal took us.

Once seated we spent a few minutes deciding on food, then made some small talk.  With her sunglasses off she revealed lovely hazel eyes, and with her rectangular face and great smile, I really liked her look.

She has three jobs.  Busy girl!  We shared good and bad sugar dating stories, and didn't talk at all about sex.

A bit of a scare, however: while waiting for our food to arrive, I saw (but wasn't seen by) a friend from my neighborhood, exiting the restaurant with some co-workers/employees.  I put my head down and pretended to fiddle with something on my shoe, and then explained to Star why I did that after he walked away.  She smiled and said she understood, and wondered if we should leave and go somewhere else.  Since I know I wasn't spotted, I knew I'd be OK.

After we finished our meal, she excused herself to go to the restroom while I paid the bill.  Of course, I checked out her ass in those tight knit pants!  Very nice, looked like it was firm without being too big.  I pretty much knew I wanted to fuck her.

As she sat down, she had a look of fear on her face.  Apparently, the girl in the booth directly behind her was a friend of hers, and knew that she'd be spotted the second we turned around and started to walk out.  I came up with a foolproof story that revolved around her freelance work.  As we left, she stopped and said hello and introduced me, so the ruse felt convincing.  As we left she breathed a heavy sigh.  As we approached her car she asked if I'd like to come to her apartment.  It was about 20 minutes away, which gave me pause, but I was so horny from this week, I didn't say no.  She gave me a small kiss on the lips -- very soft lips! -- and said she'd text me her address.

I stopped on the way for gas and condoms, and arrived with just an hour to spare before I had to leave to go somewhere else.  She lived in an old apartment building, on a major street, about 20-30 minutes from my house.  I didn't like the sketchiness of the neighborhood, and her building was next door to a mobile home park, with old trailers all over the place.  I have to say, this turned me off.  I found her apartment, which was a first floor unit far away from the street, about halfway toward the back of the building.  She let me in and I was immediately accosted by her dog.  Very cute, but she wouldn't leave me or us alone.  Small apartment, cramped with furniture, candles lit (probably to hide the dog odor), and one small bedroom.  The queen bed was pushed to the corner, no nightstand, a crappy mirror propped up against the wall and an old dresser covered in candles and costume jewelry.  The ceiling fan had one of the three bulbs missing.  I excused myself to hit the restroom to wash my hands, which smelled a little of gasoline.  Had I been totally present, I would have left the money, for which I'd forgotten both an envelope and card, on the vanity, but I forgot. 

Making out was nice, given her soft lips.  A little tongue, not too much, minimal bumping of teeth.  She was assertive and put her arms around me to pull me closer.  Before long we were naked.  Her augmented tits were gorgeous, and she liked when I licked her small nipples.  She was a little heavy, but she definitely carried it well, sort of like Dale.  She took me in her mouth and went to town, deep throating me, sucking me hard and popping me out of her mouth when she released me.  Lots of eye contact.  Felt like being blown by a porn star!  I loved it!

When she was done, she said, "Wanna go get your gear and fuck me?"  I told her I wanted to lick her first, which she gladly accepted.  At first she had her legs too close together, but I managed to push them apart and licked her with gusto.  Her torso twitched frequently, so I knew that she was enjoying herself.  In went my middle finger and I tickled her G-spot.  That seemed to get her very excited, but I could tell she was holding back.  I then heard her say something, but her thighs were sort of clamped around my ears so I didn't hear.  I came up for air, and she said it again, "How about you fuck me now?"

I got out the condom while she got the lube.  We got all ready and I entered her missionary style.  She was very tight and deep, and the deeper I pushed the more she liked it.  She reached down and rubbed her clit with her hand while I fucked her, and within a few minutes of this she came.  I kept at it, but wanted her on top and I pulled out. She gasped as I got up on my knees.  Looking down, I saw spots of blood on the condom.  She saw this and became very embarrassed, but I played it off while she raced to get wipes to clean us both up.  I pointed down at my throbbing erection and said, "What am I gonna do with this?"  "Well, I'm going to suck you off, if that's OK with you!" she giggled.

I got ready and she went absolutely to town, rubbing my balls and stroking me.  It took about ten minutes, but I got off with an intense orgasm.  She took all of my cum in her mouth, but didn't swallow.  Looking at me with a smile, she said, "Wanna make out with me?"  I laughed as she excused herself to go rinse her mouth.  "C'mon, kiss me, baby!" she repeated.

She came back and we snuggled on the bed.  One thing I learned was that she was a recovering addict.  I liked her more after that.  All in all, however, I wasn't quite feeling the vibe with her and knew this would be a one-off fuck.  At one point she asked what C looked like, and I got my phone to show her a pic from her Twitter feed.  I noticed that the time was late and I had to go very soon.  After the pic, I excused myself to go to the bathroom and left the money there, and when I returned, I said that the other awkward part of the afternoon was now under control.  After I got dressed I pretty much hurried out of there.

Not bad for a one-off. 

Wednesday, January 29, 2014

First Date with Belle

Early afternoon sunlight streamed through the high, narrow windows of the Italian cafe I'd selected for my lunch date with Belle.  It made inside feel outside, and with the wide double doors to the restaurant open, the illusion was complete.

"Just parked a block away, be there in a sec," she texted.  I'd arrived a few minutes early, got seated at a tall table near the front door and not too close to anyone who might overhear our conversation.  Another text: "In a red sweater, you can't miss me."  I got up and went outside to look up the busy side street to see her approach.  There, behind a woman wearing a pink dress, was Belle, in her red-knit sweater, black jeans, and high heels.  High.  As she approached, I sneaked a look at her legs. She had wide hips and great thighs, and I wondered what lay behind...

We hugged and she kissed me on the cheek before I led her inside to our table.  Belle had long, straight, dark brown hair, eyebrows a lighter shade of brown and shaped in friendly arches above her brown eyes.  She had high cheekbones, with a little birthmark on her cheek under her eye.  Her red nail polish matched both her lipstick and her sweater.  Great smile, although her teeth were a little crooked and she spoke with the slightest of lisps.

Belle was born and raised near the Continental Divide, and had in fact moved to our town less than a year ago.  She is a student and has one year to go to get her undergraduate degree.  Just like Leah!  She has had only one prior arrangement, with a single man, and she left that after he wanted to take things to a much deeper level with her.  As she explained it, she wasn't ready for a long-term anything, didn't ever want kids (she already has multiple pets), and was having a great time meeting men.  Besides, she said, she was much more attracted to older men who were unavailable.  Her parents were divorced, both remarried, and father divorced again.  But she said she had great relationships with all of her parents and step-parents.  I thoroughly enjoyed talking with her.  Not once did I find her at a loss for words during the entire ninety minutes we spent together. And the most important part: she agreed to my financial terms without a second thought.

Leading up to this lunch, I'd gotten the impression from Belle that she understood that I'd left my afternoon open to have sex with her if things went well.  On top of that, she even made a comment about "Afternoon Delight," and who thinks that means something other than sex?  Unfortunately, she didn't get it.  Further, she was having trouble with arranging her financial aid for school and she had to go take care of that.

As I walked her to her car, she kept leaning her body into mine.  Yes, I realized, she was attracted to me, and was definitely regretting that she didn't free up her afternoon.  We shared a few kisses at her car ("PG-rated," as she described them), and we said goodbye.

I'm now a bit torn.  Leah, clearly, has huge advantages for me, but Belle also comes with significant benefits: she lives only two miles from me, she has her own place, she's a bit older (late twenties), and she seems very, very sexual.  I guess I'll just have to see how she compares sexually to Leah.

Tuesday, January 28, 2014

Leah Cancellation #1

So Leah cancelled our date for today.  Apparently, she got her period last Friday and it hasn't stopped yet.  We're rescheduling for next week.

Meanwhile, tomorrow I'm seeing Belle for lunch, and we've left the afternoon open for whatever might happen next.  I'm going on record in saying that, if she agrees to terms, we'll be spending the rest of the afternoon together in her bed.  Unfortunately, one major obstacle to anything ongoing with Belle -- other than the fact that I'm pretty much set on Leah -- is the fact that she lives less than three miles from my house, and in fact, in my neighborhood.  It's one of my rules that she live less than five miles from my house (if we're meeting at her place).  So, this may be just a one-time thing, but oh, it's going to be awesome if it happens!

Still on with Star on Friday, and that may also turn out nice for both of us, if she agrees to terms.

Monday, January 27, 2014

What Are You A Whore For? Part II

Re-blogged from my friend, Exa Palmateri.  Money quote, an excerpt from her SA profile:
There are no rules. We can make them up to suit our needs.  I am not set on specific allowance, but there has to be a connection.  A monthly allowance is a valuation of my self-worth for offering the best of me towards my Sugar Daddy. I do so without jealousy, selfishness, drama, or the demand of his time.  It is also compensation of my valuable time that I’m investing for someone, while knowing from the start that there will never be a serious future.

I am open to anything that is fun, exciting, pleasure filled, and drama free.  However, I cannot be bought.  If there is NO chemistry this will NOT work for either of us!  I am a very physical person and am looking for that to be part of the relationship, but also like a man that can dazzle me with intellect and experience.  I am looking for a partner in crime who loves creating ADVENTURES!   
Another part that got me thinking was this one:
[Critics of sugar living] have never looked at this topic in more than one narrow minded way.  They see their lives as vastly different than that of a Sugar Baby. It really isn’t though.  [A] "friend” that called me a prostitute: she lives in a big house, only has to work part-time, drives a new car, goes on vacation, has financial freedom to make big purchases, etc.  She does and has all of this under the umbrella of marriage, so in her mind that makes it socially acceptable. I have a committed, caring, arranged relationship with a man, with all of the same benefits and I get called a hooker.
Well, that last sentence is a bit of a stretch.  That married woman "friend" also gets the associated tax benefits, the ability to sue for divorce and alimony if things don't work out, a sense of being a member of a team as well as a community, and can do all of this out in the open because she's wearing that diamond ring.  Sugar babies -- IN GENERAL -- do not have any of these benefits, because their relationships tend IN GENERAL to happen behind closed doors, far away from the prying eyes of the Sugar Daddy's community, friends circle, co-workers, etc.  I see Exa's point in the judgment of others criticizing her relationship as glorified prostitution.  It really isn't.  If I wanted a prostitute, I wouldn't be taking them to dinner, believe me.  Hobbyists who want GFEs from the hookers they "hire" want to pretend at having a girlfriend. For me, and for many other Sugar Daddies out there, the women we spend time with in these "arranged relationships" really are girlfriends, lovers, mistresses, and friends.  We've both actually made the decision to have a relationship, albeit one that's essentially recreational in nature.  As Exa wrote above, "There are no rules."  As long as it's fun and the sex is great, and the arrangement terms are mutually agreed upon, the relationship continues.

I'm secretly in love with Exa, but she doesn't know it yet.

My Week, Modified

I pulled out the sick card on Sunny today.  I'm just not up to another sex date that may be a one-off, when I'm getting very strong vibes not only from Leah, but from Belle.

So, here's my new schedule:

Monday -- off
Tuesday -- date #3 with Leah
Wednesday -- lunch with Belle
Thursday -- off
Friday -- lunch/sex(?) with Star

Friday, January 24, 2014

A Lesson for All Men, Not Just Sugar Daddies

If you want to be successful in your relationships with women, you must first be successful in your relationships with men.

I learned this many years ago, after my separation from Wife #1 and while I was fucking every girl in sight and feeling ashamed of myself for wanting so much sex.  (haha, what a joke that is to me now)

Without a doubt, I knew that someday I'd get married again.  I believe my nature requires me to be in a committed relationship.  But, I had to admit to myself, I had no idea how to "be" with women.  At that time, women were all toxic to me.  They were all fuck-toys, all distractions, and without lasting value.  They were "the enemy."  Understandable, I guess, given the state of my heart back then.

With a good amount of support from some men who were on the other side of whatever dark times they'd each had, I learned that while "understanding" women was something most men wanted to do, it was a losing battle.  In a long-term relationship, the objective was to survive, not be "happy" or feeling like you're on an equal footing with your woman.  In almost every way, women are vastly superior to men.  And since we suck at being in relationships compared to them, we'd better have tools to help us navigate.  Am I right, guys?

Men fuck up all the time.  Women do too, but as I said, I don't try to put myself in their plane.  When we fuck up, we pay a price, especially if we're in a relationship with a woman.  But if we are to be able to handle the consequences in that relationship, we have to be prepared for it.  The best way to do that is to practice with men.

No, I'm not advocating pretending the men in your life are women.  I'm just saying that a relationship with a man is a far safer environment in which to fuck up, learn from my mistakes, and move on from there.  No apologies needed, no forgiveness necessary, just tell the truth, from my heart, and move on.  But that can't be done with women.  They'll forgive, but never forget.  And when I fuck up the next time, she will pull out that list and remind me of all the previous fuck-ups to which she will now add this latest fuck-up.  Some fuck-ups will stay on the list for 15 years, some for a month.  But the list is a living breathing document.  Men don't have lists -- we don't -- so there's nothing to remember, and there's nothing to forgive.

Yesterday I was speaking with Luke, one of my closest friends and confidants, who knew a lot about my relationship with C and was someone on whom I was able to lean when C and I broke up.  I related my experience from a couple of weeks ago when I was able to let C go forever.  He didn't have to say much, but I could hear in his "Wow!" that he was surprised that it had taken me this long to let go of a relationship that, in his mind, was wholly superficial and lasted only 18 months.

I had never told him the full story, until this morning.  I said, "When you approached me to tell me that you and your wife had split up because she'd cheated on you, and then asked me for insight and advice on how to deal with divorce, you were smarting from what your wife did, and you knew DW, and I just didn't know you well enough to tell you the truth.  So, I held back because I didn't think that you'd be able to hear me if you knew.  But your reaction to what I'd told you yesterday about letting go of C made it clear to me that you needed to know everything."  And I told him that C and I had been together for six months at the time he'd first approached me, and that when I finally told him about C, she and I had just reconciled after four months apart.  The "a-ha" light went on his brain and he said, "Now it makes total sense why it took you this long!  I realize that you fell in love with her."  Which, of course, was true.

I didn't apologize, and he didn't forgive me.  We simply aired out the truth, and he thanked me for being honest and acknowledged that he would never had taken my advice had he known I was with C at the time he'd approached me. 

I've done this sort of thing with other men around other circumstances for many years -- because we all fuck up -- and it's helped me deal with the roller coaster of my marriage far better than had I never had that foundation with men.

So -- men -- if you want to practice royally fucking up in a safe way so that you're more able to deal with the times you fuck up with your woman, insist on deep, revealing, intimate relationships with the men in your lives.  Those men who can't handle you in that most vulnerable place shouldn't be in your life.

Thursday, January 23, 2014

My Next Week

Monday -- sex date with Sunny
Tuesday -- sex date with Leah
Wednesday -- off
Thursday -- lunch with Belle
Friday -- lunch/sex date(?) with Star

Somebody call a doctor.

Wednesday, January 22, 2014

Leah and the Second Date

Last week, Leah opened the door to a date without the need for an allowance.  Who am I to refuse that invitation, right?  So I showed up at her apartment at the designated time, and she was 10 minutes late.  I had a few things to do to fill the time, and soon saw her car turn the corner of her street and pull over to the curb.  As she exited her car, I spied her in my rear view mirror: long black skirt, white top, cardigan, flat shoes.  She seemed rushed, so I texted her that I saw her and would be up in a couple of minutes.  She wrote back, "No, just come right up, I can't wait to see you!"  Lucky me!

As I entered the apartment, I was greeted by a low slung ball of fur.  That would be her dog, who had returned from the vet after having surgery on his leg.  He basically stayed in his place.  I made no attempt to touch him because he had such long fur that I was afraid piles of it would stick to my suit.

Setting down my stuff, I took out a card that contained a small gift and a nice message to her.  I wasn't about to take advantage of a "no allowance" date without giving her something to show that I appreciated her.  So it was a gift card that allowed her to buy more books, which, judging from her apartment, she loved to read.  We just grabbed each other and started kissing right there in the living room.  Clearly, she did not overstate her desire to be with me.  I picked her up and she wrapped her legs around my waist.  I took a few steps toward the bedroom, but we got so busy kissing that she eventually jumped back down.  While I lifted her long skirt, she simply shoved it down and it fell to the floor.  Oh, my, did this girl have a fantastic tush!

We held hands walking into the bedroom and fell onto the bed, kissing.  I pulled her white top down to expose her breasts -- no bra -- and feasted on her nipples, which got a few very nice moans out of her.  We were naked pretty quickly, and before long we shared some very nice oral.  She did not have an orgasm after about 15 minutes, but that was OK.  After she went down on me, she climbed on top of me and we had unprotected sex for a few minutes, very slowly at first.  When the pace picked up and she wanted me on top of her, I pulled out and put on the condom and lubed up.  We had very intense sex and I came inside her.  Again, she did not come, but she said she'd gotten very close.  I could not hide a little feeling of disappointment, but she explained that before me, it had been quite some time since she'd had sex and she'd grown very accustomed to her vibrator.  Funny.  But still.  Is this girl enjoying herself?  Seems that way to me, but maybe orgasm is difficult for her.  Next time we're together, I'm going to have her guide me to help her climax.  I do have some skills in bed, but I'm always willing to learn new things!

I cleaned up and came back to bed, taking her in my arms and holding her close.  Very nice to feel this woman's body so close to mine.  Within about ten minutes, I was hard again, so she took me in her mouth again.  Again, she climbed on top of me and we had unprotected sex again.  I switched over to doggy, but for some reason, she didn't seem to enjoy that position and then my erection started to flag.  We went side by side, which I always like, but when I saw her reaching for the lube, saying, "I'm starting to get sore," I pulled out and said, "That's OK, we can stop, I'm not going to come again anyway."

Afterward we talked about a few things we wanted out of the relationship.  Leah wanted stability, and I wanted to be out in public with her.  This seemed to surprise her, as she believed married men always wanted to be behind closed doors.  After CC, C, Wanda, and Jade, I want to have the chance to feel like I'm actually dating someone.  I don't know, it just feels different than being surrounded by four walls all the time.

We talked till it got dark in the room, then I got up to shower.  While standing there under the warm water, I noticed that her bathroom needed a good cleaning, not to mention a few accessories, like bath mats.  My next gift to her for sure (on top of allowance) is going to be something that makes her apartment feel more like home.  Her place is pretty messy and needs someone to come in and clean up.  Another gift for her.

As I prepared the kids for bed that night, she sent me a text to let me know she'd had a great time with me.  I wrote back and said, "We have a real connection, don't we (apart from me knowing your mom)?"  She agreed.  It feels very good to be with her.

Still, in the back of my mind, there is Sunny, who wants to fuck me, and Belle, who is having lunch with me this week.  Further, there's Star, another girl who sent me a message.  I'd traded messages with her last summer and we spoke on the phone once, but for some reason we didn't quite hit it off then.  Maybe things could be different.  Finally, there's still Audrey, with whom I haven't connected since last weekend.  These are always good backups.  I am pretty sure I want to fuck Sunny, so perhaps that'll happen next week.  Not sure.

Reflecting on that last paragraph, it occurs to me that I have a tough time saying no to any girl who expresses interest in me.  I don't want to disappoint any of them, in case things don't work out and I want to get in touch with them in the future.  Still, I think fucking them and putting them off for three to six months might be worse.  What do you all think?

Tuesday, January 21, 2014

What Are You A Whore For? Part I

Welcome to my 300th blog post!

Re-blogging my friend Exa's blog post. Fantastically written, and spot on analysis.  Money Quote:
Escorts and hookers saw sugar dating websites as an extra income stream or perhaps a possibly more steady income stream.  Couple[d] with that, the stigma that men are trying to avoid.  ... They “pose” as a sugar daddy, when they are really a john.  They don’t want to be seen as a man who frequents escorts, yet they want to meet a sugar baby every other Wednesday, at 2pm, at a hotel, for two hours of sex/play, give her $400, have no contact whatsoever until the next appointment…and call that an arrangement. The “pay to play” mentality is like a plague on sugar dating.  Real sugar babies and sugar daddies are constantly fighting against it.  Perfect example.. a search term that brought someone to my blog, “How much do I charge a sugar daddy to skype”? Are you fucking kidding me???  A sugar baby DOES NOT charge for a call like a phone sex operator. Phone calls are about getting to know the other person, to ascertain if there is further interest.  Stop sticking your hand out for “yours”, before you even proven that you have worth.
This is why I rarely ever meet with potential SBs who want money up front to meet for coffee or lunch.  If you want cash up front, go to What'syourprice and see what you're worth.  A potential SB doesn't screen the seriousness of potential SDs by seeing which one of them will offer support at the outset.  If most SDs are like me, they meet and talk with at least three, up to six, before making any sort of a decision.  Some SDs, like me, will narrow down to their best two or three, and have sex with each of them, before making a decision (allowances included, of course!).  Some people think of that as pay-to-play, but when you are in the Sugar Dating arena, sex comes with the territory.  If there isn't sexual compatibility, there's no arrangement.  It's hard to overcome the first-time awkwardness, but if there's a bit of a click in the bedroom, you move onto date #2.

Currently, I'm in a dilemma between Leah and Audrey.  Although I'm strongly leaning toward Leah, Audrey has her sexual advantages (she was orgasmic from the first minute!), and she seems, at least for now, to be more sexually adventurous.  But Leah has warmth, romance, and intellectual talent for days, and happens to be about the most beautiful woman I've seen in years.  Up there with DW and C, no doubt about it.

The last thing I want is a glorified escort, but sometimes a one-off is kinda fun, and I'd rather use the SA website for that purpose, knowing that, in general, the women are of a higher quality, than using CL or some hooker website.  No matter how highly some escorts may be rated on these "hobbyist" sites, you just know that these women have recently fucked dozens of different men.  Pass!

Friday, January 17, 2014

Leah Makes the Booty Call

Two summers ago, I met a woman I called Jugs, and we had a very hot lunch together but didn't end up sleeping together.  During the initial phone call I'd had with her, though, she said that our twice-monthly arrangement might not be enough for her, and that she might just want me more often, just to come over and fuck her.  I'd floated the idea that, if she wanted me to be her booty call, I had no problem with it, but if she would initiate a hook-up, it would be outside the arrangement (as opposed to me wanting to hook up more often than twice a month, in which case I'd gladly add to the agreed-upon allowance).  Jugs agreed to that, but because we never hooked up, I never got to test the theory.  As time went on, I tried that approach with Wanda, Lola, Jade, and just the other day, Audrey.  None of them has ever taken the bait.

Today, however, I sent Leah a text just to wish her good morning and to find out how her final exam went for her winter break course.  In her reply, she tacked on a question to see what I was doing over the weekend.  I am totally booked with family and work commitments, but I made sure to tell her that I'd rather be in her bed. Here's what followed:
L: I was just thinking earlier how badly I want to ride you on my couch.
Me: Wish I could swing the allowance today, but feel free to use me as your booty call whenever.
L: Maybe you can be my booty call next week :-)
(Now, I wasn't sure yet, so I added one more comment)
Me: Then I wouldn't be able to see you for three weeks.
L: No allowance next week. Just fun :-) Allowance is only twice a month, right? :)

So, we have made a date for next Tuesday afternoon.  There will be no allowance, and it will be just for fun.  I'm under no illusion that this sort of thing will happen often, or even more than once.  But I'm thrilled at the idea.

Wednesday, January 15, 2014

Home Front News -- Rule Breaking and Big Breakthroughs

My last post about my marriage could be summed up in this clip:
My DW just simply forgets what it means to be a "wife."  She defines herself as "mother" and "homemaker," but when it comes to her husband, I may as well be her roommate.  The problem is that she filters "wife" through the other categories.  She cooks and cleans, and mothers our children.  And she says that my being more present in the lives of our kids "turns her on."  But it's bullshit.  Nothing really turns her on anymore.  I could be The World's Best Dad, and she'd fall asleep at the drop of a hat after the kids go to bed.
After leaving Audrey, I headed home, taking the time while in the car to steel myself against yet another stressful day.  The kids, who had been gone for two days, would be back temporarily for a couple of ongoing extracurricular activities.  We'd had some modicum of peace in the house until this day, when the kids would bring back with them their usual brand of craziness and chaos.  As hard as DW and I work to rise above it, however, that chaos drives a wedge between us.  After the extracurriculars, which would end about 8 pm, we'd then have to take both of them back to their grandparents' house, get them ready for bed while over there, then drive home again.  We probably wouldn't get home until after 10 pm.

Further, this would be our last day before we spent the weekend at a relationship enrichment workshop.  I don't want to detail things too much here, as the event is very specialized and disclosing it would reveal more about my identity than that which I'm comfortable.  I can write, however, that it's intense, very revealing work, and I was excited and very fearful about what might happen afterward.  If things didn't go as I was hoping they would, this particular night might be the last time she and I would have any chance to be sexual.  I normally have a very iron-clad rule that I do not have sex with DW for 24 hours after a sugar date.  With this urgency, however, I decided to break my rule.  We were both so tired after our evening that we simply collapsed and fell asleep once we got home.

At about 5 a.m., I turned to her and started rubbing her back and making overtures.  While tired, she didn't resist and we had pretty sleepy and boring sex for about five minutes.  So, if this was the last time, I thought, it would be pretty par for the course!

The workshop challenged both of us.  DW had a much harder time of it than I did.  The first day we spent apart on the various exercises, and I enjoyed every minute of it.  When we got home that night, we had an assignment to complete, which I was able to do but she was not.  However, there was one exercise that we had done separately during the day that she now wanted to do together.  And it really drew us closer than we had been in many years.  The next day started with a guided meditation of sorts that lasted about an hour.  During this process I was able to dig deep and uncover some real pain I had still been hanging onto from my time with Hayden.  A suggestion entered my mind to say goodbye to past pain, so that's exactly what I did.  As I sobbed and my body shook, I mouthed the words, "Goodbye.  Goodbye C [her first initial]."  I kept saying it again and again, and eventually I could see her face sort of shrivel up, like a color photograph that fades to sepia tones, and then float away, gone.  At that moment, I felt totally freed from all that pain, and felt free of C.  She was, I recognized, gone forever.

[Note: I decided in this post to use the first initial of the woman I've called Hayden since the beginning for one specific reason: as I formally let her go from my life, I also want to remove the sting of the name Hayden from my consciousness as well.  Reducing her name to a single letter makes it easier for me to let her go.  I also want to stress that I feel no animosity or bitterness in finally letting her go.  I am truly at peace, wish her well, and will, I hope, never have to dwell on any aspect of our time together.]

Then I was overcome by guilt at having hurt DW and my kids during the year or so since C and I split up, when I was reeling from the sadness and confusion.  "I'm so sorry," I cried, over and over.  Being able to articulate this pain lightened my head and my heart almost immediately.  I sat there after the exercise, alternately crying and then laughing out loud with the joy of release.  I opened my eyes and looked to DW, who crawled into my lap and curled up with her arms around my neck, at which point both of us cried.  I hadn't deduced at this point that her crying was because she didn't experience what I had; that, in fact, she felt she had gotten nothing out of the exercise, and was frustrated to the point of despair that she wasn't "connecting with anything" compared to me or other participants in the workshop.  Upon learning about this from her over lunch, I assured her that her process was nevertheless profound and that discovering the degree to which she had been shut down over the years was, in and of itself, a huge leap forward.  We completed the workshop later that day, and at the close, noticed a much softer, glowing face on my beautiful DW.  What this meant, I still needed to see, but I remained very pleased by what I was seeing.

The upshot of this work we did was that DW was indeed softening and becoming much more yielding to my attention (which, I think, had also softened and become less insistent).  I was able to touch her body in ways and places that up to that point had pretty much been off-limits.  Yesterday afternoon, after I returned from my work day and the bed of my latest Sugar Baby, Leah, she announced to me that she would like to put some of these practices to use.  Her coded way of telling me she wanted sex.  Well, it had been scarcely an hour since my last orgasm inside Leah's pussy, and I had no idea how I was going to manage observing my 24-hour rule.  Fortunately, once again, the children proved an excellent way for me to seek cover until I could be ready.  By the time we climbed into bed, DW fell fast asleep.

Some time later, DW rolled over from sleeping on her stomach to her side, and her butt was against my crotch.  She wiggled it back and forth, and coaxed some life into my little friend.  I pulled her close, stroked her from her shoulders to her knees, and we eventually made love.  However, this time, she actually let me go down on her, for the first time in what seemed like a year (at least).  She was already wet, but she didn't come because, she said, she was "just too tired to work up to it."  Again, we had intercourse, but clearly we were making love and not just cleaning the pipes.  When I came, I stayed inside her until my erection subsided.  There has been a major shift, indeed.  It's in our voices, on our faces, and, I believe, in our hearts.

What this means, faithful readers, I don't yet know.  I face a significant dilemma: do I continue with my sugar activities?  Do I stop and focus on my marriage?  Hard to say right now.  For now, I'm taking a wait and see approach.  I don't have to decide today.  If I do, you'll be among the first to know.


Isn't that a shitty title?

See, I've written for many years: blogs, short stories, newspaper articles, and hopefully a book fictionalizing my Sugar Daddy adventures.  Words rarely fail me.  They might jump off the page/screen, they might fall flat, or they might send readers away.  I try to do my best each time.  Today, however, there simply aren't enough words -- perhaps not any words -- to describe fully what I experienced yesterday with Leah.  All the hackneyed cliches about fireworks, or explosions, or fiery hotness, or sensuality -- they all fail.  If I could find the right words to convey, they'd have to invent a new writing award just for me.  So, I simply must struggle through this blog entry with the same old crap.  I apologize in advance.

Today, the morning after my first encounter with Leah, I still vibrate so intensely that I could probably levitate. After it was over, I actually stumbled with nearly every step from her front door back to my car, like a drunk, except fully aware.  I sat in my car for about five minutes before driving off, hands on the wheel, eyes easing shut then whispering open, trying to integrate all my senses to be able to navigate rush hour traffic.

The midday sun smiled on me as I left work early to pick up the necessary gear to keep Leah and me safe from mistakes.  I arrived at her place about 10 minutes early and sat in the car, answering emails and text messages.  I couldn't stand more than a few minutes of that torture.  Leah was in her apartment, waiting, and wanting as much as I was wanting to be together.  I sent her a quick text to let her know I had arrived and asked if she were ready to receive.  About two minutes later I was knocking on the door to her apartment, an otherwise clean mid-century garden-style building with old screen doors and faded beige paint.

Leah answered after I rang the bell.  Right after I saw her, I smelled her floral fragrance.  She wore a short white cotton dress with horizontal black pinstripes, that ended high above her knees.  Walking in, I pulled her close and kissed her.  "You look beautiful, baby."  I set some of my stuff down on the arm of her sofa and looked around.  A lot of floor space, and a lot of empty wall space.  "I moved in just about four months ago," she said.  A dining set with four chairs, a sofa, a chair, three tiny coffee tables, and a medium-sized flat screen TV, connected to Pandora and playing some of my favorite music.  "I listen to everything," she said, "but I really love classic rock."  This hip-hop-era girl, with her curly black hair and busty curves, made steady progress in how much she was impressing me.

I sat down with her on the couch to make small talk for a few minutes about music, but it wasn't long, perhaps 10 minutes, before I said, "OK, I'm gonna kiss you now, because, well, I have to."  From the moment our lips touched we didn't separate for about five minutes.  Just because we needed to get up and go to the bedroom.

I went ape shit in describing the various sexual goings-on with Audrey the other day, but for this blog post I'm not going to do that.  You're all probably feeling a bit disappointed right now, but like I said, I just can't find the words to describe what went on between Leah and me.  We kissed a lot, we got naked, I went down on her, she went down on me in spectacular fashion, I put on a condom, we had sex, I came, we talked after, I kissed her some more, she went down on me again, and we had sex again and I came again, in the space of about 90 minutes or longer.    That is really all I can muster.

More importantly was how I felt when I was with her.  For probably the first time in nearly six years of doing this, I felt I was addressing an intellectual equal.  Leah was an old soul, who understood stuff on a level I haven't seen in peers of mine 30 years older.  On top of that, she was gentle, kind, patient, and honest.  When I asked, she told me that she did not have an orgasm.  "I rarely have one with someone the first time we're together, but with you I came closer than I ever have before."  There was no need to wonder on my end if she was being sincere or not.  I could see it in her eyes, into which I stared, without taking too much time to stop smiling, the entire afternoon.

Leah's sexual talents put her at or near the top of my list in every category.  But what really made her stand out was how she looked.  Other than needing a pedicure, I could not find a single flaw on her.  The reason I kissed her as much as I did was because her lips felt and tasted like juicy berries.  When I saw her breasts the first time, in a texted picture, I was seeing an illusion.  The two-dimensional image did nothing to communicate just how glorious her breasts looked, felt and tasted in the flesh.  She also had no tats!  Anywhere.  "I hate them, actually," she said, "especially on women."  At one point while I was inside her, she got on top of me.  From that vantage point, looking up at her body, I was overcome.  The woman's all-natural body sucked the breath out of me.  I hold her up as proof that there is a loving God.

On the way home, she texted me, "I'm still lusting after you... thank you for making my day incredible."  In response, I wrote, "I knew you were going to be incredible, but I was not prepared for how drop dead gorgeous you are. Thank you for an afternoon I will never ever forget!"

Wait.  It got worse:
Leah: I'll definitely be thinking about it the rest of the day, and probably until I see you again.
Me: Let's just agree to be obsessed with each other for the next two weeks.
Leah: Done!
This morning, as I was writing this post, she sent me a picture of herself getting ready to step into the shower.  I will now have to take care of myself in the only way I know how.  Have a great day, everyone!

Tuesday, January 14, 2014

Audrey, Part III

After sex, Audrey and I took a moment to clean up so we could hang out and get further acquainted.  I returned to the bed to find her relaxed, with the previous sex-demon look on her face replaced with a contented smile.  I snuggled in close and we kissed.  Compliments exchanged, I talked with her about her tats.  The tat near her hip, she explained, was done when she had just turned 18, and she now regretted having it.  She figured at some point she'd get it modified and updated so that it didn't look like that anymore.

The tattoo on her side, however, looked recent.  "This is a religious symbol, you know," I said.  "Are you [of that faith]?"  "I am," she said.  "Oh, me too," I said, "do you belong to a [house of worship]?"  "Yeah, we go to our local [one] once in awhile."  "Which one is that?" I asked, afraid to hear her answer.  When she did, my jaw dropped.  "Holy shit," I said, "that's where my family goes too.  I bet we've bumped into each other there and never knew it." 

The same trepidation I felt at having learned who Leah's mom was had returned.  My rule had always been never to sleep with anyone I knew, or whom my wife knew, or anyone in our community.  Our [house of worship] was definitely within our community!  What if I knew her parents as well? Audrey was just a year older than Leah, and it was conceivable that Audrey's parents were acquaintances of ours.  Once I learned her last name, however, I felt a little better, as I knew no one with that last name (or at least that's what I believe today). 

But Audrey, like Leah, thought this whole "too close to home" shit was hot, and she slid over to me and started kissing me all over.  Taking hold of my cock, she coaxed me back to life.  Soon I was fingering her again, feeling how wet she had gotten.  I climbed on top of her and attempted to enter her again.  As she was on birth control and I had already had one orgasm, I felt pretty confident that it would take me a long time to reach the point where I would ejaculate again.  This time, instead of saying, "Get the condom and lube," Audrey just requested that I get the lube.  I got us both slicked up, and I slid into her.  This time, our fucking was far more aggressive, changing positions multiple times, using the mirror, with me pulling her hair as I slammed her from behind, spanking, pinching her nipples.  She came two more times before I was totally exhausted.  I withdrew and collapsed, out of breath.  "Break time," I pleaded.  Once I caught my breath, however, I was still hard, but thought I would try something else. "Tell me a story," I said, "one that you find totally hot."  I started stroking myself.  She began to tell me a story of a threesome she had had with her previous Sugar Daddy. "Touch yourself," I said, and she opened her legs wide, with her left leg draped over my right leg.  We masturbated in front of each other as she related this very hot story (of course, the details were completely unimportant -- I was watching her play with herself!).  After a few minutes of this, I was ready to cum again, so I pulled her close and came on her chest.

She decided that she'd take a quick shower.  And I nodded off on the bed.  When she came back she said, "I need a nap."  "Join me," I said.  We didn't sleep, however.  We talked a little more, mostly about having threesomes together and trying some anal play next time.  Would there be a next time? I thought.  I hoped there might. 

I got up to shower off too, and when I returned, I asked her if she needed to use the bathroom.  She said she didn't.  "Go to the bathroom, and close the door," I said.  She didn't ask why, just did it.  I quickly retrieved her allowance and unzipped her purse, slipping the money inside.  Pulling on my pants, I said, "OK, you can come out whenever you want."  She came out and began dressing; once she and I were both dressed, I looked over and her and there was this look of "Well...?" on her face.  "Oh," I said, "taken care of, in your purse.  I typically have a card or an envelope, and I leave it on the bedside table, but this time I forgot it and I didn't want to have an awkward moment handing you a wad of cash."  "Sweet of you, Porter!"  "Yes, it is!" I said.

We left the room together and shared a kiss on the balcony.  I got in my car and drove home.

Over the next three or so days, our communication with somewhat limited, as I was away over the weekend.  Yesterday, however, we chatted by text.  I told her about my amazing weekend (to be revealed later), and how sex with DW showed some promise.  Her reply was generally supportive, but I thought I'd detected a hint of jealousy and I asked her about it.  "No, I'm not jealous," she wrote.  "Something tells me that you have a pretty insatiable appetite for pussy."

"Yes, but I am coming from a place of total sincerity when I tell you this: Until you tell me otherwise, I'd like you to be my primary sexual partner.  The other being my wife of course."

"I'd like that too.  I see a few wild threesomes in your future too."

"Of course," I wrote, "I also need to tell you that this week I will probably have sex with one other girl, but I think it'll be just a one time thing.  This is part of my having total openness with you."

"That's fine, thanks for letting me know.  I do appreciate that."

Continuing the openness vibe, I wrote, "I get the impression, though, that you have a high threshold for satisfaction.  You seem submissive, but you know what makes you feel good and you ask for it.  Powerful.  I hope I'm worthy."

"You are definitely worthy.  Haha.  It was so hot."

"Your fave part?"

"Cumming together.  And when you went down on me."

"Aww," I wrote, "a romantic at heart."

She asked me the same question.  "Ten thousand kisses," I wrote back, "and going bareback."

"I really love kissing too."

So there's a good connection there.  Again, I wouldn't say she was the hottest girl I'd ever seen, but her sexual openness and adventurous nature certainly strikes a chord with me.  To me, when there's a genuine connection, looks aren't really all that important.  I would not have put Jade at the top of my list of beautiful women, but we did, at least for a while, have an amazing personal connection.

Keeping things open for now with Audrey.  Leah is next (today in fact).  Will update soon.

Monday, January 13, 2014

Audrey, Part II

As I awaited Audrey's arrival at the hotel, I busied myself with my usual ritual: clean myself up (although I had no time for a shower, so I just washed my hands and face and then cleaned up my penis and groin area of sweat, etc.), try to set the lighting right, make sure the curtains are pulled closed (as the room looked out onto an outdoor walkway), adjust the air conditioning to a comfortably chilly level, and set out her money.  I cased the small room.  Typical three-star hotel room, a little small, with light fixtures everywhere outfitted (now) with compact fluorescent lamps instead of incandescents.  The blue bedspread was inexpertly spread out over the bed, as if it had been sat on or fiddled with by someone prior to my arrival.  Three soft, downy pillows in white cases, white sheets tightly covering the king-sized mattress.  Small bathroom, very clean, with a small window featuring privacy glass.  TV, chair in the corner, standard furniture. 

It occurred to me at that moment that I had not thought of a card or envelope in which to put the "allowance."  I had opened every drawer and cabinet looking for an envelope in which to stash the allowance, but only the top level of hotels offer free stationery anymore, and even then that's spotty.  So, for the time being, I left the cash folded in my wallet.  I'd sneak it into her purse when she was in the bathroom.  One thing I did notice which offered a small amount of hotness: the room had a full length mirror at the side of the bed near the bathroom.  If the mood struck -- and with this voyeur the mood would definitely strike -- a little bit of watching ourselves might add some kink to the proceedings!

I sent Audrey a quick text to let her know to park on the street as there was no parking in the very small hotel parking lot without a permit from the front desk.

Shortly after I got dressed again came a text from Audrey that she was parking and would be up in a minute.  I had left the door propped open by the manual door lock so that she could come right in, and I took a peak out the window to see her approach.  A couple of minutes later, she waltzed right in.  We shared a kiss once she put down her purse and she showed me the (large) box of condoms.  "You're set for life!" I joked.  I always prefer a three-pack just in case things don't work out.  Sending her home afterward with 11 or more condoms feels a little cruel of me, but I suppose that's just my overdeveloped sense of fairness (hehe).

After getting her buy-in on the room lighting, I returned to face her and I thanked her for showing up, and for having the adventurous streak to just jump into bed with me.  Repeating her line at lunch about not saying "no" too often anymore since she typically enjoyed most of the things she did, I sensed, and seized, a moment.  "OK, then," I said, inching closer and placing my hands on her waist.  "Let's start enjoying this."

Her 5'1" height was a great attraction for me.  I like small women a lot, and not only was she short, she was petite in build and looked like someone I might have wanted to date in my non-sugar life.  As we kissed, we pulled each other closer so that our bodies were touching from shoulders to knees.  Of course, my body reacted to this woman's touch and her kisses, and it didn't take long for us to collapse onto the bed, me on top and my right thigh insisting on space between her legs.  Our hands discovered each other's curves and angles like two blind people working to open a box of cookies.  Since I knew she had small breasts, I wasn't surprised to feel a very firm bra cup underneath her blouse.  The warmth I touched between her legs demanded that we hasten to achieve nakedness.

I unbuttoned her blouse, which revealed a white strapless bra that disappeared in short order.  Although I was pretty hard at this point, I got harder seeing her small breasts and pink nipples which were already erect.  I was hungry and started to devour her body.  Next off were her jeans and then her panties, followed quickly thereafter by all of my clothes.  I noticed a large tattoo on left side, and realized she and I might be of the same faith.  I smiled!

Audrey's earlier bubbly personality and loud voice vanished once we were naked.  Her flushed cheeks, dilated pupils, and quick breathing -- not to mention a look of utter urgency on her face -- told me that she had moved to another level.  I did not believe at that moment that she was drifting upwards into some Tantric climb up her chakras from the root chakra into samadhi.  No, she had descended into a pit of fire, a once-smoldering but now fully engulfed inferno of carnality and debauchery.  I thought I was hungry; Audrey looked like she might tear me apart at any moment.  Despite her obvious appetite I determined to go at my own pace; her pleasure seemed rather assured, so I decided to focus on mine.  What, you were expecting some kind of tender, romantic journey?

As I continued what felt like ten thousand kisses, I moved down to her pussy to taste her.  She was already wet and she smelled sweet and musky at the same time.  My cheeks brushing against reddish stubble of perhaps a couple of days, I pushed my lips and tongue into her and nibbled and flicked at her clit.  Her clipped breathing told me I'd done the right thing.  Then again, I wasn't really in doubt.  I opened her like a ripe fig and feasted, reaching upward to squeeze, then pinch, then caress her nipples.  Moans.  Yes, moans, that's what I wanted to hear!

Now, I know it's cliche to ask the question, but when in the middle of an extramarital sexual encounter this hot, it's customary to ask your partner if she's enjoying herself.  So, after I stuck a finger inside her and massaged her G-spot, the situation begged the question.  "Ya like that?"  "Oh my God," she said, "that feels so fucking good."  As I finger-fucked her, I resumed licking her clit.  It didn't take long before she demanded, "Don't stop, I'm gonna cum!"  It needs to be said that her legs could not have been farther apart without their being behind her head, giving me full access with my face and hands to enjoy the vibrations of her orgasm.  Audrey climaxed the way Pentecostals found Jesus. In other words, she spoke in tongues.  No, I'm just kidding here!  But my cock got even harder when I felt and heard her orgasm.  And I managed to escape without having her thighs clamped down on my ears!

Stroking her inner thighs and kissing around her pussy, I brought her back to earth.  She wore a beaming smile.  Without a word, we switched positions and I eagerly anticipated feeling her mouth on me.  She produced an elastic band from her wrist.  "Ah," I laughed, "look how prepared you are!"  "Yeah, my hair tends to get in the way sometimes!"  Pulling her hair into a crude bun, she knelt beside me and took hold of me, kissing the head and licking the shaft.  I took my right hand and caressed and squeezed her tush, slipping my fingers in between her legs to finger her again.  She licked and sucked my balls.  My, I thought, I couldn't remember the last time a woman did that to me!  She massaged them too, and I opened my legs to give her greater access, which she must have interpreted as an invitation to get in between my legs and proceed.  I lost contact with her behind but surrendered myself to her blowjob skills.  Holding the back of her head I tried to fuck her mouth, but winced at the scraping of her teeth.  Ouch!  All in all, 'A' for effort, 'C' for execution.

It was time.  My cock throbbed and we could not separate our faces for all the kissing.  I rolled her onto her back, head on the pillows at the head of the bed, and got between her legs, kissing her tenderly, licking her nipples, nibbling at them with my lips.  Audrey dug her nails into my shoulders, and I wondered if she were marking me.  I hoped not!  I positioned my cock and put the head of my cock inside her.  "Go get the condom," she whispered.  "Huh?" I pretended not to hear. "The condom," she repeated, "and lube."  "Of course, babe.  Be right back," I said.  Undeterred by the break in our rhythm, I got up and tore open the condom box and opened the lube bottle.  I stroked a little of the Astroglide on myself before putting on the condom.  "Lets the condom slip up and down on me while I'm inside you, so you actually feel my dick fucking you and not a piece of rubber," I explained."  "Good thinking."

When I entered her, it took a few seconds but with a little extra lube, I slipped in, balls deep.  Going slowly at first, we increased speed and kissed constantly.  It didn't take long before I felt a twitch and I released a little jizz into the condom.  I pulled out for a second before going back in.  I was so hard, I knew I'd come again.  With her legs spread so wide, and with her being so small, I was able to take hold of both her ankles and hold her open and thrust very deep into her.  She grabbed her breasts and moaned some more as I fucked her harder.  "Oh, yes, do that, don't stop.  Don't fucking stop!  Oh, yeah, I'm gonna cum again!"  I typically don't really like fucking really hard for a really long time, but this time felt different and I saw absolutely no reason not to accede to her demand.  She again announced that she was coming, and I decided to join her.  As soon as I knew she was mid-climax, I let go and exploded inside her, falling onto her and burying my face in the crook of her neck.  More and more and more kissing!  So fucking hot, even with our mouths dry from all that heavy breathing!    Without words, she and I both decided I should pull out, so I took hold of the base of the condom and withdrew.  The condom was full of cum and I jumped out of bed and took the mess into the bathroom.  I grabbed the washcloth I used before and wiped myself clean before rejoining her on the bed.  Phew!

to be continued...

Saturday, January 11, 2014

Audrey, Part I

As I exited my office building for the walk to the Mexican restaurant, I zipped up my jacket against the afternoon chill.  Funny how it warmed right up once I emerged from the shadow of this towering behemoth, and I felt instantly overdressed.  I could hear my mother's voice in my head, "It's always good to have jacket handy, just in case."  Thanks, mom.

Had I paid attention at all, I would have realized that the restaurant was literally a two-minute walk from my office, and I might have picked a less conspicuous place.  Once I arrived, I saw about half a dozen tables occupied, and a lot of open space, so I didn't really think it was a bad idea after all.

I texted Audrey to let her know I had arrived, and she replied that she was ten minutes away.  Waiting in front of the building, I checked email, Facebook, the Sugar Daddy website -- anything to occupy my busy mind.  I was determined that, today, I was going to get laid, but I wasn't exactly sure how I was going to fit it in with my schedule.  I had a late afternoon appointment at the garage, from which DW was supposed to pick me up.  I sent DW a text to let her know that I might have extra work this afternoon and that my appointment might be an hour late.  I had already set it up at the garage that I would bring in my car at the last possible moment, but that I would try to bring it in earlier.

Audrey texted that she had parked.  I made my way to the restaurant's rear entrance to see if she were in the parking lot.  Nope.  Back to the front.  I saw a petite, auburn-haired girl walking up the street, wearing a crop top and black jeans.  She had pretty wide hips in proportion to her shoulders.  I hope this isn't her, I thought, but as she got closer, I realized it was her. At first I didn't think she was cute, but after she removed her sunglasses, I suddenly noticed that, hey, pretty fucking adorable.  Big brown eyes underneath that hair, fair skin, and showing off that pierced navel.  Cute tush too.

The restaurant was not crowded, and we could seat ourselves anywhere, so we picked a table way on the other end where there weren't any people.  It turned out to be a great choice, as you'll find out in a minute.  The tables were not clean, but I didn't bother to ask for a wipe down.  Who knows if they'll use a clean towel, right?  The Yelp reviews I'd read prior to picking this place, with three or fewer stars, were starting to come to my mind as Audrey and I made small talk.  Wow, she has a pretty loud voice, and she doesn't seem to notice it at all, I thought.

Audrey's work is brand new: she just finished school, and now she said she wants to go to grad school and maybe do something else.  "So you're the restless type," I said, "someone who gets bored easily."  "Not really," she said, again, too loud.  "I just am not sure yet what I want to do."  At her age, she seemed a little old to be still searching, but okay.  I liked her hair and her smile, so I focused on that.  Plus I was really interested in hearing about her "wild side."

The meal was disgusting -- overly cheesy, indistinct spiciness, not at all appetizing, like some well-intentioned person said, "Let's take all the good things about Mexican food and put it all on one plate at the same time, all mixed together."  I finished less than half of it.

Audrey and I spoke about the arrangement and she agreed to my terms.  I was batting a thousand this week, four-for-four!  Even with me speaking in very quiet tones, she still had not figured out that she was speaking far louder than she needed to, and I was actually getting irritated, so I gestured to her to take it down a notch.  "I'm sitting right here," I said with a smile.  She didn't really get it, because she was still too loud.  I was sort of done with this place, but not done with her.  I wanted to talk about sex, so I brought up some experiences I'd had, and asked her to do the same.  She seemed like a very game girl, and seemed to have as much of a passion for sex as I did.

"Listen," I said at last, leaning toward her. "I want to pay the bill, take you somewhere close, and fuck the shit out of you."  Her ever-present smile disappeared, but in a good way.  "Are you down?" I asked.  "Yes," she replied.  Her smile was now gone, and I detected an ever-so-slight flush come to her cheeks.  Was she embarrassed, or was she now completely fucking turned on?  "You're sure?" I said.  "I like that you're up for this spontaneous proposition."  She said, "I've learned that if I say yes to something that sort of makes me uncomfortable, I end up having a great time anyway.  It's pretty much like every time I tried something sexual that scared me, I ended up loving it."

I told her I needed to book the room and get some cash, but gave her the name of the hotel I'd had in mind, just about 10 minutes away.  It took no time to get the bill paid.  I walked her to her car, where we shared a pretty hot kiss, and then ran back to my office to book the room, shut down my computer, and get the hell on the road.

On the way to the bank, I texted Audrey and asked, "Did you get totally wet when I told you I wanted to fuck you?  Because your face completely changed at that moment.  I thought you were totally turned on."  "Yes, I was," she replied, "I am. :)"

Navigating mid-day traffic nearly drove me nuts.  It took me thirty minutes to go about three miles to get to the bank.  Once I got there, however, I was in and out in no time.  Another five minutes or so to the hotel, parked, registered, and got to the room.

Audrey showed up about 15 minutes later, after she got condoms and lube.

to be continued.

Friday, January 10, 2014

In the Cold, Cold Light of Day

Me: Morning!
Leah: Good morning! :)
M: so I've had a chance to sleep on things...
(three minutes later)
M: ... and since I woke up hard and thinking of you, I'm convinced that we should move ahead
(seven minutes later)
M: what are your thoughts?
(four minutes later)
L: I touched myself yesterday...and this morning...thinking of you and what I want to do to you.
M: so you're not interested...
M: you know, my car could just magically steer itself over to your place right now.
L: I definitely want to see you again, absolutely.  But I can't get rid of the feeling this is a betrayal to my mom.  But then again, you two aren't close friends or anything.  If I was 100% sure she would never find out I would be OK because I know this would hurt her... I don't know, I'm torn.  When you said yesterday we should do this one time and not agree to any sort of arrangement after that, that's a good idea.  A one-time thing I could deal with.  And then maybe go gradually from there and see how we feel.
M: I can definitely understand your feeling that sleeping with me might possibly violate some unwritten code.  It certainly falls into the category of taboo.  But I think "betrayal" is kind of a strong word, don't you?  I'm perfectly fine with taking it one step at a time.
L: Okay, let's do that. Calling it taboo is so hot ;)
M: I'm still in my car...

Thursday, January 9, 2014

MUST READ: A WCSD Journal First!

The anticipation over meeting Leah this afternoon did not overwhelm me.  I'd been thinking more about Audrey and Sunny.  Even though Leah has her own apartment, her young age gave me pause.  But we were meeting today, and I'd seen some pretty nice photographs to know that she was a very lovely girl.  Being Sugar Daddy to a early 20s woman had some serious appeal for me.

I arrived a few minutes before our 4 pm meeting time.  I picked the same neighborhood coffee bar where I'd met Arabia, Gia, Naira, Heather and Annette.  The cooler weather ruled out a table on the outdoor patio, and the inside was very crowded, so I picked a table to avoid losing out on one once she arrived, and waited.

Leah showed up at about 4:05, so not too bad.  I saw her enter from my vantage point.  She had cut her dark, wavy hair, which in the pictures appeared to be well past her shoulders, but now it stopped right at her shoulders.  She wore a light colored top and longer skirt.  The top showed off her very beautiful breasts.  Her dark eye makeup reminded me of someone (well, Hayden at first), and she had a vaguely middle-eastern vibe going.  I liked her right away.

We stood in line and made some small talk.  She was majoring in psychology, and is taking a winter break online course before returning to classes part time in two weeks.  She's also interning once a week.  Currently she has a lot of free time, but once she returns to school, she'll only have a couple of free days per week.  No worries, I thought, I only needed one!

We found a different table, farther away from the door, a little less conspicuous.  She excused herself to use the restroom but returned quickly.  During her absence I sent a text to my friend, Exa, to say Leah was hot.  She drank her coffee through a straw, which I found endearing and little quirky. 

Continuing with the small talk, I said, "So, you grew up in (the adjacent) county?"  "Yeah," she replied, "and [the town where I grew up]."  "Wow," I said, "where'd you go to high school?"  She mentioned a rival high school.  Interesting, I said, "you're from my town.  I went to [my high school]."  "Really?" she said, "and you're [my age]?"  "Yeah," I said.  "Well, you might actually know my mom, because she's the same age as you."  I asked her last name, but she wouldn't tell me.  She then said, "You're [my real name, first and last], right?"

I sat up straighter and narrowed my eyes a bit, looking at her face to see a resemblance to anyone I might know.  It didn't fully register that she'd known my full name, but I was surprised.  I thought about her actual first name.  When it hit me -- when I'd put two and two together -- my hand shot to my face and covered my gaping mouth.  My eyes shot wide open.  "Oh, my God, I do know your mom!  Is she [mom's maiden name]?"  Leah shook her head in denial, but the facial resemblance totally gave her away.  "Your name is [her full name], isn't it?  I know it's true, because you look exactly like your mom."  Leah admitted it was true, and we both sat there and stammered, stunned, not knowing what to do next.

I briefly entertained the idea of leaving right then and there.  After all, I actually knew her mom.  I told Leah that her mom and I been in classes together, and we'd had crushes on each other.

Her mom had the most amazing tits I'd ever seen, and I couldn't help but stare at them whenever I talked to her.  One day, late in the school year, I went to talk to her and never even bothered to look at her face, and went straight to her tits. She wore a dark brown polo shirt, unbuttoned to her cleavage.  When my eyes had found their target, I saw a tiny little sign sticking out from between her breasts.  On the sign was written one little word: "hi."  I looked up at her face and she was smiling her cute little smile.  Mortified, I turned and walked away, but not before a guy behind her started cracking up, saying, "You are so caught!  You're so busted!"  This makes for such a poignant story for me, because I haven't changed one fucking bit! When Leah had earlier taken off her jacket, I caught a glimpse of her cleavage and smiled to myself, and thought, wow, I'm still doing this, just like I did with [Leah's mom]!  And I hadn't even yet made the family connection!

Granted, I hadn't seen her mom in many years, but we had gotten reacquainted on social media, and we communicated with each other once or twice a month.  She had divorced Leah's dad, a total asshole, a long time ago and had remarried.  But he was a full-blood middle eastern guy.  I now understood how I'd picked up on Leah's look right away.

Leah sat there, appearing to be fully composed, but then she said, "I really don't know what to do now.  I got on the site thinking no one would ever know I was doing this, and here I am sitting with a high school friend of my mom's."  (UPDATE: Having read this last sentence, it occurs to me that Leah absolutely knew who I was before she ever set foot in the door).  We agreed that we'd have to process this huge surprise and really evaluate if we should just say goodbye and forget we'd ever met.  I kept asking her how she felt about it, and she kept saying that she was processing it.  She'd told me earlier that she'd found my pictures attractive, and now she was saying, "I think I'm even more attracted to you now knowing who you are."  I couldn't lie to her; I found her unbelievably hot, and her being this woman's daughter just made her hotter to me.  (What is it with me and ratcheting up the risk like this?  Unprotected sex, public displays of affection, and now my friend's kid?  Yikes.)

After a few minutes, we sort of calmed down and just started talking.  Neither of us wanted any pressure, so we just moved past it.  I reminisced about her mom, and her mom's best friend, to whom I'd lost my virginity.  I also told her about one day when her mom, her friend, and I were at the friend's house enjoying the jacuzzi.  I think we were about Leah's age at the time.  After we got out and toweled off, we'd moved into the friends's bedroom and sat on the bed, just talking.  I gave her mom a bit of a back rub, but nothing more.  Her husband, Leah's dad, showed up about 15 minutes later, and when he saw the three of us emerging from the bedroom, I saw his face kind of fall and his demeanor immediately go from friendly to sullen.  Apparently, he was not only an asshole, but a jealous asshole.

Most of the rest of our meeting is kind of a blur, because being in the coffee bar, it was actually a little difficult to talk about the arrangement stuff.  I did, however, learn that Leah's last arrangement had lasted two years and was with a man her dad's age.  I now understood her thing for older guys -- making things right with her asshole of a father).  She also told me that her mom knew about her sugar activities.  "She saw that I wasn't working, so she knew there must have been some way I was paying for school and my rent and my Audi.  She thought I might actually be escorting, and she was relieved when I told her I just had one Sugar Daddy."  No one else in her family knew.

After about 45 minutes, I decided that we needed to leave the coffee bar and start processing this meeting on our own time.  She agreed and I walked her out to her car.  When I got to her Audi (a white one, second time this week), we sort of grabbed each other and started kissing.  A little at first, but she opened up her mouth and pulled me closer to her.  It was so hot, but I suddenly became aware that I was in a public parking lot, kissing a young woman, wearing my wedding ring!  Idiot!  I broke free, kissed her cheek, and said I'd talk to her later.

After a few minutes in my car, I sent her a text: "I'm absolutely sure that I want you."  Her reply: "I want you too."  I called her and we chatted some more.  Felt better to talk this way, safely in our cars with no prying eyes or ears around.  It was clear, I told her, that the attraction between us was very strong, and she agreed.  "I'm so attracted to you, Porter."  I mentioned concern that I had about what would happen if things ended badly between us. "I mean, we both have a lot at stake, and we've been in these situations before, but let's remember that we're also human and not immune to making errors in judgment."  She was puzzled that I was playing the end of things before they even began.  "No, that's not what I'm doing," I said. "I'm just sharing with you what's in my head.  In my gut, I believe we'd be discreet, safe, and mature about this.  You're very mature for your age."  "Actually," she said, "I'm three years older."  "Huge relief!" I laughed.  "Why did you lie about your age?"  "Well, men like younger girls."  "Listen," I started, "for a guy my age, a really young girl is just too fucking young!"  I told her my rule about dating women at least Hayden's age.  "So," I said, "should we give it a try?  See how things work out?  Maybe stay non-committal about it until we've satisfied our curiosity and checked what's in our guts?"  "You mean, like, just one time?"  "I dunno," I said, "maybe a couple, three times, and if things feel awkward and uncomfortable we can just say goodbye and good luck."  We agreed that this would allow us to satisfy our attraction for one another and determine if we both possessed the maturity to hold things together.

So, dear readers, a WCSD Journal First!  I am going to have a mutually beneficial arrangement with the daughter of a high school friend.  I have no idea what I'm doing.  I'm a little scared about it.  I'm going to be very careful, but I'm absolutely going to fuck this beautiful woman.

On Tap For Thursday

Today, I am meeting with Leah.  Leah is an early twenties brunette, with an amazing body and beautiful eyes.  She is younger than I prefer, but she has a thing for married men and has her own apartment.  She's also agreed to terms.

A couple of days ago, she emailed me a pic of her fully nude shot from the side.  She hid her breasts, but I could tell they were fantastic in other pictures.  We haven't talked about sex too much, but that will change today. I'll get a good feel for how she is around me and I'll be able to tell fairly quickly if she's into me and not just the allowance.

Will update on her later.

Meanwhile, all day yesterday, Audrey and I exchanged texts and got very sexual.  This is the girl who claims to be a "girl next door" with a wild side, so I wanted to push her boundaries.  Here is a text transcript:
Me: So you're my little nympho, are you?
A: haha yeah
Me: What makes you a nympho?
A: I love sex and everything to do with it: toys, porn, threesomes, bdsm...
Me: You're bi?
A: Yes
Me: I'm a voyeur, a watcher.  Maybe you and your gf could put on a show for me.
A: Perfect, I'm very into exhibitionism.  I love when people watch.
Me: :-) Every gf I've ever had says she likes to have people watch, but they get stage fright when I sit there and watch, stroking my dick. LOL
A: Haha poor you.  I've been obsessed since I checked out a swingers club.
Me: Always wanted to visit one
A: It was strange but fun
Me: I've had one threesome in my life and it was the most extraordinary experience ever
A: I've had a few.  My fave.
Me: Two guys or two girls?
A: Two girls
Me: Do you live alone? (haha, I'm going in for the kill now)
A: No, roommates. 
At this point her phone was going dead so we took it up again about four hours later, after I'd returned home from my meeting with Sunny.
A: Hey just got off work.
Me: What is your work? (she'd said she was a student)
A: I'm a [profession]
Me: Ah. That explains [a lot].  Don't [people in your profession] make a pretty decent living though?
A: Thx.  It's pretty good.  I wanna go to grad school though.
Me: Oh right.  So, are you evening dates only, or do you get some days off during the week?
A: I'm off Fridays and some Tuesdays
Me: Challenging.  But not overly so.  You don't work at [nearby location] do you?
A: Lol no.  
Me: Would be awkward to have you [working on my wife] LOL
A: Ha probably
Me: I could be free Friday for a meet
A: I'm free Friday
Me: Lunch, or ???
A: Yes let's do lunch.  I can meet anywhere.
Me: How about your place? ;-)
A: Wishful thinking, but I can't host at the moment
Me: There's always someone there?
A: Not always, On fri there will be.  Plus I'm not gonna invite over someone I've never met :-P
Me: I understand, I was just kidding.  You're the one I want to meet.  Nothing turns me on more than a girl who looks like a good girl but is a little slutty deep down.
A: Perfect.  I think we'll get along then.
Me: You like it rough and loud or slow and romantic?
A: OMG rough!  Haha slow and romantic, no thanks
Me: Hair pulled, slapped, fingered till you squirt? :-)  BTW, nothing wrong with slow and romantic.
A: Nothing makes me hotter than having my hair pulled while getting fucked hard. I'm super into restraints too.  And ur right, nothing wrong with slow and romantic, just not for me.
Me: So doggy is your fave position?
A: IDK if I have a fave position, but doggy is up there.
Me: Would you ever do a video (privately)?
A: Maybe, once trust is established.  Taking pics is fun, haven't done a video yet.
Me: Yeah, just probing your boundaries.  I take it you're not into anal. I love pics too.  God I'm ready to meet you now.
A: I like some anal play, finger or small toy only.
Me: K, I'm totally hard right now, thanks!
A: No prob :-)
Me: :-) Feel free to share whatever pics you have.  I'm a very grateful SD LOL
A: That's funny.  You read my mind. I was just going through my pics
Me: Can't wait...
The first pic was of her booty shot, wearing a sexy thong.  She followed with her on her knees, wearing nothing but a G-string, then one of her in a bra, pulling her panties down to reveal her shaven pussy.  A bizarre tat on her right hip. Very bizarre.  Very standard piercings.  She has very small breasts, so I texted, "By the way, don't hide your boobs, I love small breasts. Loooove them!"

The next was of her fully naked facing the camera at a slight angle   She has a very cute body.

I can't wait to meet her Friday. I'd say that she leads the pack right now, but I am concerned that we wouldn't be a good fit sexually.  She turns me on like crazy, but her size (5'1") is a bit small and I'm afraid my cock would be too big for her.  Further, I don't like rough sex that much.  I prefer the slow, tender, romantic sex that Hayden and I used to have.  But everyone's different.  I don't mind pulling her hair and slapping her ass, so long as she likes kissing too.  We'll just have to see.  But I'm of the mind right now that I'll be fucking this girl soon.

It Might Always Be Sunny!

Yesterday I met with Sunny, one of my potentials.  Her profile showed that she was in her early thirties and a blonde.

We met in her neighborhood at an organic food café.  I picked the place; I'd wanted to go there since Elle had suggested it as a meeting place some months back (a quick aside: Elle has deleted her profile from the Sugar Daddy website).

I arrived on time, got seated, and waited for her arrival before ordering.  I wasn't going to eat, as I'd had a pretty big lunch, and I've been overeating lately and gaining weight.  She arrived 15 minutes late, calling from the street in front of the café to let me know she was walking in.

Sunny clearly cares about her appearance.  She showed up wearing a black lacy top and black jeans and no heels.  She has a nice figure, curvy in the right places and definitely not overweight.  Not a lot of makeup either.  I got up as she walked over, gave her a hug and a kiss on the cheek, and she then excused herself to use the restroom.

We ordered once she got back and started chatting.  She asked me immediately about my ethnic heritage and told me hers (eastern European mix).  She thought we might be from the same geographic region given our facial features, but she and I do not share anything, as far as I can see (that means, she's much better looking than I am).  She was born and raised in a neighboring state, and now lives in Southern California working as a consultant.  She has her own apartment that wasn't too far away from where we were, which I found very positive.  I think I've grown very tired of hotels, although the historic one I've been using still has its appeal to me.

Sunny is actually in her late twenties.  I didn't ask why she exaggerated her age in her profile by only a year, but no matter.  She's also really a brunette, not a blonde, but that didn't matter to me.

We chatted about relationships (what else?) and she revealed that she'd been three years out of a serious relationship with an older man who'd had kids.  She said she's moved into a new phase of her life where she is focused on career and having fun, and sex is a huge part of that for her.  She said she's not dating or hooking up with anyone, but going out a lot with her girlfriends and looking for a Sugar Daddy.  She accepted my allowance terms and we got that out of the way, which made me happy because I was starting to dig this girl.  We talked a lot about sex as well (of course).  Since we were in public, it was a lot of quiet talk, but it got hot nonetheless (or maybe because we were quiet)!  She said that she was enjoying having sex with girls, and had had a foursome (three girls) with her last Sugar Daddy while on vacation with him.  I told her I'd done it once and would love to do that again.  She also said that she loved to masturbate and did it at least once a day.  Wow, this girl and I were a lot alike!

After about 45 minutes, I had to leave to get home, so I paid the bill and we started to walk toward the door.  It had gotten chilly outside and she didn't have a jacket, so I pulled her close to me and walked her across the street to her car.  Of course I was going to kiss her!  We said a quiet goodbye and I lightly kissed her lips, which turned into a very hot, open mouthed kiss with a good amount of tongue action.  She wasn't aggressive with her tongue, but just firm enough to make it very sexy. I really wanted to feel her mouth on my dick at that point.

I definitely think Bobby is a backup at this point.  I'm aching for the sun!

Tuesday, January 7, 2014

Update on The Dancer

I finally heard today from The Dancer.  You might recall that she had reached out to me on LinkedIn, and then we exchanged messages there.

She texted me as I was sitting down to dinner with the family.  When I had a free moment, we took a few minutes to reconnect, and she asked me about my writing project.  I told her that I would be able to talk to her in half an hour when I was in my car.  She replied that she'd have a few minutes and to call her.  I said I would, and then asked her to say hello to "our mutual friend."  She said she would.

That was probably a big mistake.  A few minutes before I was leaving she texted me: "Actually, something came up.  Maybe another time."  I wrote back a few minutes later: "Later this week, perhaps?"  No answer.

When I got logged into LinkedIn tonight, I noticed that The Dancer had viewed my profile.  I looked a little further and noticed that we were no longer connected.  Perhaps she'd communicated with Hayden and something had been said.  That's what probably "came up."

Oh well.  Not that I really needed her for the project.  Serves me right for trying to bridge the gap, though, even just a little.

Potential Updates

Since yesterday's post, there have been some updates on potentials.  Here they are:

Bobby: just met her for lunch.  Sent the text I said I would send in my last post.  Here it was: "Great meeting you (actual name).  My allowance offer is $1k for twice a month, quite a bit less than the last guy.  Not sure if that satisfies, just wanted to put it out there.  Once I am in an arrangement I'm very reliable so there's that to consider. If not that's ok too.  Have an amazing day."  She replied that this would work for her.  Very cool.  I like her.
Sapphire: emailed me this morning to let me know that she was not interested in another married Sugar Daddy.  No worries, I replied.  She was too young anyway.
Sunny: Meeting her tomorrow afternoon.  After a phone call yesterday afternoon, we exchanged text messages last night. 
Me: I still can't believe that you brought up sex before I did!
S: Ahahaaa I win ;D
Me: Something tells me this would be a win-win situation
S: I have a feeling it just might be
Me: Just a quick question: are you avail during the day, or would our dates be evenings only?
S: Days are open.. I do freelance (usually from home) so I make my own sched.  Always good to plan a day or so in advance tho
Me: Of course :-) A booty call is kinda money sometimes...
S: LOL..I'm super flexible ;D ha but yeah, my sched is open in pretty free flowing
Me: My calendar is usually open too.  Sex in the morning is so fun ;-)
S: Ha yes! And best way to start the day ;D Plus better than a masturbation sesh for the day ;)
Me: See ya tomorrow then? ;-)  And to steal from Woody Allen, "Don't knock masturbation.  It's sex with something I love."
Me: Someone * HAHA
S: Yes, someTHING I <3 (texts picture of what looks like a small vibrator and her laptop)
Me: What the hell is that?
S: A vibrator and an ipad ahaaa! Best masterB combo... nothing's better than the real thing tho
Me: Hahaha! Do you use porn?
S: Yes love from time to time
Me: A girl after my own heart.
S: <3 <3 <3
Me: Say you're bi and I'm yours
S: Just jumpin in that game last cpl years...have some good stories for u
Me: You're awesome.  And sufficiently nasty
S: Ha u have no idea yet
Me: Lol.  Try me...
S: I will when we meet...all about fun n happiness
Me: Sounds great.  Maybe we meet closer to your apt.
S: Lol maybe.  (The place where we're meeting) is actually super close to my apt but we'll meet n feel it out...
Me: I was only half-serious sexy.  Very tempting though
India: Did not respond.  She's not interested.

Some new potentials:
Daisy: mid-twenties, a nanny, latina girl with blonde hair, great tits in her pics.  We are supposed to meet next week, though I may not make it that far after meeting Sunny (or, if she doesn't work out, Bobby).
Leah: early twenties, 5'4" white girl with huge brown eyes.  A student who really really wants a married Sugar Daddy.  She reached out to me, and her pics were amazing.  Can't say anything's going to come of it, but the pics got me very interested in her.
Audrey: mid-twenties, 5'1" white girl with light brown hair.  Very petite, student.  Very girl next door, but she says she has a wild side, so I'm intrigued.  She lives pretty close to my home so there's that risk, but we're at least talking about meeting at some point.
Belle: late twenties, 5'7", full time student.  Dark hair and eyes.  Very cute.  Very detailed profile.  To which I responded in detail.  Really seemed to hit it off.  We're going to meet next week sometime.