Friday, February 28, 2014

Sugar Baby or Hooker? Sugar Daddy or "Hobbyist?"

There are many who argue that this whole Sugar Baby/Sugar Daddy arrangement shit is nothing more than a more subtle form of prostitution.  Essentially the argument goes like this: if a woman agrees to have sex with a man in exchange for money, gifts, dinners, trips, etc., she's a hooker, full stop.  If a man gives a woman any sort of valuable consideration in exchange for sex, then he's a john (I used "hobbyist" in the headline because that's what men who frequent hookers call themselves), full stop. 

I'm sorry, but these arguments are simplistic because those who make them are thinking one-dimensionally.  Further, I would wager that most if not all of them who hold to these arguments with certainty have never been in a Sugar relationship.  As someone who has been with both escorts and Sugar Babies, I know the differences, and they are vast.

First and foremost, when I would engage in sex with an escort, I never gave more than a momentary thought to who they were as people.  For me, they were selling a product and I was a buyer of that product.  Once in awhile, I'd meet an escort and enjoy a bit of conversation over some subject or other, but it was no more meaningful a conversation than one I'd have with the person checking my groceries, or fixing my car at the local garage.  The conversation passes the time, and nothing more, until both of us decide that the transaction has ended (usually when the next person in line gets annoyed enough!).  With my sugar babies, I nearly always spend just as much time (if not more time) conversing than fucking.  This is a huge difference to a hobbyist, who pretty much just gets in, gets off, and gets out.

Second, with nearly every one of my sugar encounters, even the one-offs, it was important for me and her to get to know one another before we hopped into bed.  On her end, she is looking for a man with whom she can feel safe, who shows some measure of charm and who is passably attractive to her. While I wouldn't go so far as to assert that we're looking for shared values, if we discover that there are shared values, it makes things so much better.  Because, in the final analysis we are looking for a relationship, not engaging in a business transaction.  Anyone who has read this blog from the beginning knows that these women are people to me (unless I get very mad at them or feel particularly sorry for myself when I get manipulated by them).  When I saw escorts, they were fuck-toys, some with better personalities than others.  I was with some really sweet escorts, and I encountered some horrible girls too.  But so what?  Here's your money, open your mouth, spread your legs, get me off, and thank you very much!  This was the arrangement, and was always understood.  No escort I ever saw ever complained that I wasn't a gentleman or an otherwise decent customer (especially those I saw more than once or twice).

Finally, while I haven't experienced this yet, I have read accounts of Sugar Daddies who have maintained friendships with their Sugar Babies long after the arrangement had ended.  I would like to have this kind of relationship, particularly with Leah or with C.  There isn't an escort I ever met who hoped to be able to see her customer as a friend after their transaction ended, and as a hobbyist I have never expected an escort to offer me her phone number so we could get together for coffee or a walk on the beach.

But there is an element to the simplistic argument I noted above that does resonate with me: every one of us, men, women, sugar or not, is a prostitute for something.  We have all sold ourselves at some point in our lives in ways we wished we hadn't in exchange for some needed and worthwhile benefit.  Those who reject that argument are liars.  Many of us have worked jobs we hate because we needed the paycheck.  We may have done business with a rude customer because the financial rewards were worth it.  Some women have remained in marriages with husbands who ignore their needs because a) there may be a status element to the marriage, or b) they have no marketable skills and could not survive on their own.  She may even have grown to loathe her husband over time, but because he makes a great living and she gets to have enough time to hang with her girlfriends, at the gym or over lunch at the country club, and they get to travel to nice resorts or on luxury cruises, she crawls into bed with him and puts up with his "three-minute mile" until she can watch The Tonight Show or a DVR of "Modern Family" after he falls asleep.

The final point I want to make is this: sex work need not be bad.  The simplistic argument above implies that it's a horrible thing to be likened to a hooker.  I've read enough accounts of sex workers who feel empowered to use their bodies and sexualities to be able to finance their way through school or make up for a financial shortfall when the job doesn't pay the bills.  If it goes well, everyone "comes" away happy; what could be bad about that?

Wednesday, February 26, 2014

Heavy Hearted

It's rare that I actually grow to dislike a woman after I've had sex with her.  In recent memory, I can think of one -- D (Jade), whose lying and unflagging narcissism got so under my skin that I told her off in spectacular fashion a couple of months ago.  If I go through the others with whom I even had a one-time thing, there are only a few: Paulina, who showed such promise but turned out to be a total dud; Karen, who lied about her age; and Song, the Korean girl who was just so crazy.  For all the others, I only have pleasant memories that overshadow any of the reasons why I'm no longer with them.  The ones I really disliked were the ones I never slept with.

In this context, my heart has been heavy the past few days because I realized I must end my arrangement with Leah.  In fact, in hindsight, I never even should have kissed her that fateful day last month.  She has all the qualities I prize in a Sugar Baby: beauty, intelligence, clear goals, self-reliance, compassion, a lack of neediness, and passionate sexuality.  We are connecting on a deep level, emotionally, intellectually, and sexually (although I figured by now she'd trust me enough to be able to reach climax).  But there's a huge barrier between us: her mother, who is a high school friend of mine and with whom I still have occasional contact through Facebook.  I cannot escape this barrier or get around it.  Every time I look at Leah, I see her mother's face.  I had one opportunity to see Leah's mom in a swimsuit, and I can recall that her body then, at age 23 or 24, looks like Leah does now.  It's just too weird for me.  Also, that Leah and I are having unprotected sex is so foolish for me, I simply have to end this before we get too enmeshed with each other.  I imagine that if we were still together in a year and I tried to extricate myself from the relationship, it would be so much harder to do it. Ending now avoids tons of emotional damage down the road.

So, ever the cautious bet-hedger, I will wait until after I sleep with Belle before I take care of Leah.  if Belle and I don't work out, I still have Audrey.

Friday, February 21, 2014

Date Scheduled with Belle

Next Friday afternoon, I'll be walking most discreetly down a street in my neighborhood, less than a mile from my home, to gain entry into Belle's apartment, populated with a large dog and two cats.  I have to admit that the proximity factor and the pets are major negatives against Belle, though neither have anything to do with her.

But seeing these pictures I am struck with how fucking hot she is.  I can't wait to see her and touch her.  I hope that our obvious connection at lunch will translate in the bedroom.

Much more to be revealed, I hope!

Wednesday, February 19, 2014

The Bloom is Off the Rose

I highly prize punctuality everywhere in my life.  As I see it, if I'm not early, I'm late; there is no such thing as "on time."  I asked Leah before I left for her apartment that I was leaving my office and to have a parking pass on her windshield for me.  Further, I showed up at Leah's five minutes early and texted her immediately that I was downstairs. She responded a few minutes later -- after the appointed hour, by the way -- that the parking pass was on her windshield.  I took care of my car and walked up the stairs to her door.

Since she had studies to attend to after our date, I knew we'd have just a limited amount of time, so it bothered me a little that she'd had her phone on silent (not vibrate) and did not get my text right away.  I say "a little" because it wasn't a huge offense to me; we'd make up for it in other ways.  She greeted me at the door in a lavender satin nightie, as if she'd been sleeping in all day.  Except of course, she'd arrived home only a half hour earlier from school.

After a nice kiss and a warm hug, I kicked off my shoes and she started fiddling with her TV to get some music going.  While her back was turned, I retrieved the allowance envelope and placed it on her dining room table.  We went into the bedroom to play.

Before having sex, however, we engaged in a little practice I picked up from the relationship workshop I attended with DW last month.  We sat, cross-legged, on the bed, fully clothed, looking into each other's eyes, and asked each other three questions in turn.  I'm not going to reveal the exact questions, but they touch on sexual fears, fantasies, and ideals.  As I saw it, Leah struggled with articulating her fears, or perhaps she didn't quite understand the question, but once she asked me the question and heard where I was taking it, I saw the light go on in her head and I gave her some time to go into it after all the questions were asked.  The fantasy question was very enlightening; Leah's fantasy involved a committed relationship, even marriage, and deep trust with her man so that she could have an orgasm.  It revealed to me that her ability to achieve orgasm was actually something she struggled with more than she'd let on.  She was deeply afraid of being vulnerable, as her superficial answers around her fears indicated.  Her answers around her sexual ideals involved more what she didn't like versus what she actually liked.  In the light of day, I believe that extricating myself from this relationship, when it's time, will be more difficult the more enmeshed we get.

Sex was delicious, of course.  Unprotected, she put me inside her after going down on me in her slow, sensual way.  I didn't get to go down on her, but I didn't really mind it today.  We went very slowly, and at times I wondered if she was enjoying herself.  I deliberately slowed down the pace because I could have climaxed at any point and didn't want it to end.  So once I finally did, I popped on her belly again like last time.  We cleaned up and snuggled together and talked about the questions and answers.  Not much more to reveal than what I observed above.

We had sex again a little while later, but neither of us came.  I showered up -- and she'd bought me some masculine body wash this time instead of my having to use her flowery girly stuff -- got dressed, and took off for home.  One of the first thoughts I had, bizarrely enough, was that I should give Belle a call.  Weird!  What this told me was that a) I was feeling too vulnerable with Leah -- and I had revealed quite a bit of myself during our questions -- or b) the bloom had dropped from the rose in our relationship and it no longer had the sweet smell and beauty it once had.  In hindsight, I think it's probably both.  Later on, in listening to a male friend of mine talk about how none of the things in his life are delivering the satisfaction they once did as he approaches middle age, I was struck by the same insight as it pertained to my time with Leah, D (Jade), Audrey, Star, and Elle.  In fact, I think that perhaps the entire sugar enterprise was feeling a bit old and stale to me, and I wondered if perhaps I was finally feeling like it might be time to hang it up.  More to be revealed there, but this is where my heart is right now.  I'm seeing Leah and all the others as a distraction in my life, keeping me from focusing on more important things.  Sugar Daddies are typically more together in their personal and professional lives and have the space to entertain these young girls, but I'm using them as replacements for what's missing.  It doesn't feel good, at least right now.

Tuesday, February 18, 2014

Leah -- One Month Anniversary

Leah and I got together a month ago on January 14, which made Valentine's Day our official one-month anniversary.  We will be together this afternoon for the fourth time, and I couldn't be more excited.  So excited, in fact, that I have butterflies in my stomach!

Still, ever the hedger, I am still in contact with both Belle and Audrey.  More and more I've felt like Leah and I might not be as sexually compatible and I am with Audrey.  Since I haven't yet had sex with Belle, I don't know if we're compatible at all, but next week I should know the answer to that question. (Note: I did find out that Belle lives just over a mile from my house.  The building is on the corner of two very busy streets, so I know I'm going to have to be very careful when walking in and out of her building to make sure I'm not spotted by anyone I know.)

Friday, February 14, 2014

Happy Valentine's Day

To all of you who have faithfully been reading my blog, Happy Valentine's Day!

To Leah, Audrey, and Belle -- you're all in my thoughts.

To D (Jade's first initial) -- I wish you the best.

To C -- I will love you forever, even if you wish I never existed.

And, to my beautiful DW -- my secrets and all they signify do not alter for one minute or one iota the fact that you are the love of my life!

Thursday, February 13, 2014

No Sugar Activity This Week

Since it's Valentine's Day tomorrow, I decided to take this week off from sugar and devote my attention solely to my DW.  It's paid off.  Lots of kissing and holding and touching and making love (although she still hasn't taken the oral plunge -- and probably never will).  I'm in love with her, and this has only deepened my feelings.

Last night she and I hired a babysitter and we went out on an eight-couple date night to a local restaurant.  Of the eight couples, six are married, and the other two are in serious long-term partnerships.  Ages ranges from mid-40s to mid-60s, professions all over the map, so lots and lots to talk about.  Private room, lots of wine, great conversation, and a great big bill ($2,100!).  Still, a great time, and I'm a little hungover and full of food.

Next week I'm supposed to get together next Tuesday with Leah, but Belle wants to meet too.  I managed to push Belle back to the following week (the week her next semester starts) so we haven't yet nailed down a date, but I plan to do that today.

This morning I woke up and thought about Audrey.

Thursday, February 6, 2014

Great Third Date, but Leah Still Doesn't Get There

Busy week!  Haven't had much time to blog or read my other fave blogs.  I had a date earlier this week with Leah, our third.  I'd spent most of the day out in the field, which turned out advantageous for both of us.  She'd asked if I could arrive earlier than our scheduled 3:30 time, and I was able to make it to her place a half-hour early.  That, at least I'd thought, would give us extra time to hang out and play more, but she told me that she had studying to do, and that we'd only have about two hours, the typical time.

Earlier in the day, I asked her if I needed to go buy more condoms, or if we had any left.  She replied that we had a couple of condoms left, but that she was fine having sex without any protection.  She trusted me, she said, and I "just felt so good" inside her.  I wasn't going to object, but I made a mental note that I'd pay close attention to my body to make sure I withdrew well before I got close to climax.

When I arrived, I noticed that all the street signs around her place warned that parking was limited to two hours unless one had a special parking permit.  I sent up a text to her to see if she'd had a permit for me.  She said that I should meet her downstairs and she'd give me one from her car.

I was surprised to see her walk outside wearing a black and white polka dot sundress.  It revealed a lot of her skin, particularly her legs.  At 60 degrees outside, jacket weather, it was definitely not the kind of weather that suited a sundress.  Had she worn that dress to school today?  Must've given those pimply-faced boys a nice thrill!  She got the permit from her car and walked it over to me.  I gave her a quick peck and walked back to my car to hang the permit from my rear view mirror.

Once inside, I peeled off some of my clothes and took off my shoes.  We fell into each other's arms and started kissing like we had been separated for far longer than two weeks. Our bodies touched from our noses to our knees; I couldn't pull her any closer, although I tried!  When I felt that my dick was hard enough, we moved into the bedroom.  She turned to me and said, "I was going to surprise you with what I was wearing, but when you texted me that you needed a parking permit, I threw on this dress."  So explained the dress!  "Go ahead and put it on," I said, "I'll wait out here in the living room."  I closed the bedroom door.  As she changed, I checked a couple of emails from work and turned down the volume on my phone.  Again, I forgot to seize the moment and deposit her allowance -- safely tucked inside a sweet and sentimental Valentine's Day card -- somewhere conspicuous.  I got another chance later.

She called me into the bedroom.  When I opened the door, she stood there in a black teddy, sheer from her breasts to her waist, with black panties and black pumps.  Dear readers, I've said it before but it bears repeating: Leah has a jaw dropping beautiful body.  If there was anything I could point out as a flaw, it would be that her legs were slightly short in proportion to the rest of her, but it's almost unnoticeable unless you, like me, study bodies in your spare time.

Her clothes, as sexy as they were, were off in fairly short order.  I went down on her first, and again, while she made a lot of noise and her body was quite responsive, she did not cum.  She gave me a fantastic blow job, a little faster and more urgent than before.  She then climbed on top of me and put me inside her.  Oh, heaven, here you are again!

With every stroke, Leah got wetter and wetter, to the point where we could hear the squishing sounds from all her juiciness!  Loved it!  I deliberately went very slowly, because I wanted to enjoy being inside her for as long as possible, and because I read somewhere that if you really want your woman to climax, go slow.  Thought I'd give that a try.  We kissed so much, we held each other so close, we touched each other all over.  We made love, my dear readers!  I rolled on top of her continued the slow touch.  Couldn't resist pounding her a little.  I spent much of my time, however, going as deep inside her as I could and holding there.  She got more and more excited each time, and there was a time or two when I thought she actually came.  Eventually, I started feeling that familiar vibrating at the base of my cock which told me to pull out.  I did and pre-cum dripped out of me onto her belly.  "Haven't cum yet," I said, starting to stroke myself.  When I did climax, it felt like it would not end.  I laughed out loud and leaned over to kiss her sweet lips before excusing myself to get a towel to clean both of us up.

Our chat revolved around a couple of old stories she'd wanted me to tell her about how I knew her mother.  One was the embarrassing story I related to you a while back.  Another was a story about her dad thinking I'd fucked his wife, which I hadn't but, I confessed to Leah, I wished I had.  Leah absolutely had her mom's young body.

We got chilly, so we climbed under the blankets to cuddle.  It didn't take long before we were fucking again, this time much more roughly.  I lubed us up ahead of time to avoid her getting sore like last time.  It worked.  Very hot.  She sucked me off to try to make me cum, but because I was spent from the last time, I didn't cum, and again, no orgasm for her.  I confessed to her that I had hoped she'd feel comfortable enough to climax.  "It takes me a long time to cum," she said.  I replied that I'd have to go down on her for as long as it took.

In my head, the story is that we're not as sexually compatible as perhaps I think we are.  This is why I'm very excited to see how things go with Belle next week.

I thoroughly enjoyed our date, and Leah and I are in like with each other, but that emotional connection needs to be coupled, at least for me, with a really strong sexual connection, or else the relationship won't work for me.