Friday, August 22, 2014


For months (for years, actually), I've fantasized about having group sex with another couple.  I remember talking about it with C after we had our threesome with The Dancer.  I remember a time when my first wife and I discussed it, back in the mid 1990s.  To me, having sex with another couple seemed the hottest thing ever, the apex of sexual exploration.  What could be hotter than watching the woman you love (or at least like a lot) fuck another man or woman?  To this voyeur, nothing!

Audrey and I, since resuming our occasional hook-ups, have discussed this too.  Lying in her grey-sheeted bed after a great fuck, we'd often fantasize about things we'd like to do together.  And Audrey, being bisexual and a nympho, had nothing but enthusiasm for the idea.  It just took some initiative on our parts to make it happen.

My first attempts had me looking on CraigsList.  Everything can be found there, right?  I clicked on "Casual Encounters, and then the link for "mw4mw".  This turned up dozens of postings, some with photos, and some without.  Most of them posted their ages and many of them their specific locations, which made it easier for me to navigate.  But one thing I noticed was that the ads seemed to repeat every day, and that there seemed to be only about 20 couple or so posting these ads, with the occasional new one popping up every few days. I didn't respond to any of them yet; I really didn't know what I would say, since I was completely new at this sort of thing.  Audrey, however, thought that simple honesty and accurate photographs were the best choices.  After all, those choices were what led me to find her!  Smart girl!

In addition to CL, I signed up on a couple of "lifestyle" websites for swingers (one suggested by Audrey).  I uploaded photos, but mostly what I saw on these sites were a bunch of older, fatter, and not very attractive couples.  I actually wanted a hotter couple who resembled the hot girls I'd usually found on the sugar daddy website.  "You're going to have to look at a lot of ads before you find the one you want," Audrey told me.  "Just be patient and one will come along."

I even posted ads on CL, uploaded pictures of us.  Got a few responses, but nothing that jumped out at me. I was close to giving up, the way I sort of gave up hoping that C would arrange a threesome for us.  But instead, I decided to lower my standards and be open-minded.  At my age, was it really realistic to expect and hold out for a very hot couple who would fuck us without a financial incentive, when it took my financial offers to attract the hot women I fucked as a Sugar Daddy?

Once I relaxed the criteria, I noticed that there were far more options.  Eventually, I saw one on CL that really grabbed my attention. The headline read simply: "Lunch."  The ad showed a pair of exposed tits and a cropped blow job shot.  I responded with a nice note and got a response back from the guy (apparently, it's usually the guy who sets these things up).  We chatted for a bit, and we agreed, after sharing a few additional pics to get the girls involved.  I forwarded the email chain to Audrey and she wrote back, "I like them! They seem nice!  Let's meet them!"  The guy's GF responded in like fashion.  And then we revealed real names and shared some details about ourselves.

"B" was in his 40s, married (hah!) and had been with his mistress "J" for about a year.  They were not a sugar couple, but lovers that met through B's work in the healthcare field.  He lived about an hour away and J lived near where C used to live.  J had just separated from her husband, no kids.  B had two kids.

We agreed to meet one afternoon at a centrally located hotel, bring some wine and condoms, and see where things go.I got to the hotel on time, Audrey just a few minutes later.  I saw J wandering in the lobby with her cell phone to her ear.  She looked over at me a couple of times, but I wasn't sure she was who I thought she was, so I didn't approach.  But I was certain that she was checking me out and talking about me with B, who via text told me he had secured the room and was waiting upstairs.  Once Audrey showed up, we headed up to the room...

Answering the door was a mid-40s-looking guy with longer brown hair, dressed in a pink dress shirt and suit pants.  J was sitting on the bed, wearing a pink top and black leggings.  She had long brown hair and a nice smile.  Both B and J spoke with accents, although B's was very slight.  They revealed that they were both Latino.

We shared wine while sitting as couples on the separate beds.  B and J started to snuggle as we chatted.  It took about 20 minutes before I took the initiative and started kissing Audrey.  Within a few minutes we were all naked.  Wow, that was easy!

J had great breasts with dark nipples, but I have to confess that she was heavier and flabbier than I like.  In fact, going back through all the women I've been with over the past six years, J was the heaviest.  CC and Elle were both pretty flabby, but at least they were thin.  Watching J ride B's cock, I could see her belly flab going up and down with the rest of her.  It was not a pretty sight I have to admit, although it was cool to watch her suck his dick like a hungry animal.  I went down on Audrey and made her cum.  J came over and joined us, kissing Audrey while I was down on her.  B stood back and jacked off.  The whole scene was hot as fuck!

I'm not going to give the full play-by-play here, but I remember some great highlights.  J got on top of Audrey and kissed while they scissored each other.  Both of them came really hard.  B fucked J while J sucked my dick (nice).  B fucked Audrey in missionary position next to J and me.  Now, a lot of time has passed since we'd begun, I'd leaked a little jizz inside Audrey pretty early on, and I had to wear a condom, and I wasn't 100% knocked out by J.  I was not 100% hard either, and I tried to fuck J, but I lost my erection.  "Whew!" I said as I pulled out.  "Break time!"  It was swelteringly hot in the room.  I moved to the other bed while the three of them had fun.  Next, Audrey came over and kissed me while B fucked her from behind.  Again, I moved over to the other bed, condom now off, stroking my dick while Audrey climbed on top of B and started fucking him.  She must have had three orgasms.  The guy never got soft, even though he said he came ten minutes into fucking J at the very beginning.  I admired his stamina!  Watching them fuck got me hard, but I didn't want to fuck J.  J saw me masturbating and came over to help, taking my cock in her mouth.  She sucked like a champ, and I enjoyed every second of it.  It had been about an hour since we'd begun and I didn't want to hold back any longer.  I let go a blast of cum that got everywhere on the bed and in J's hair.

B and J then disappeared into the bathroom and fucked in the shower, while Audrey tried to revive me.  No go.  I was spent.  B and J came out and fucked some more, while Audrey and I spooned on the bed and watched.  The moment felt slightly romantic for me, as I held Audrey close, stroking her small tits, and rubbing her body with the other.  She turned her head toward me and we shared a whole mess of tender kisses.  Did we move to a different level?  I don't know; I'm not gong to think about that.

We left before they did, as they were still fucking as we slipped out of the room.  Audrey and I thought we'd see them again, but now I'm not too sure.  I'm not attracted to J so if we did get together, I think I'd avoid trying to fuck her.

We'll see if anything changes in the near future.  But Audrey and I did enter a new phase: the swinging phase!

Thursday, August 7, 2014

Update on My Life, Part 2

As I said in my previous post, I have essentially left the Sugar lifestyle, but did have a couple of slips back in the past five months.  I described two of them, which involved Audrey.  The third one involves Leah.

Right after seeing Audrey again, I'd started to miss Leah.  You will recall that Leah is the daughter of a woman who was a high school classmate and a current friend on Facebook.  I ended the arrangement with Leah because I had been unable to wrap my head around these two facts and feel good about sleeping with her daughter.  Over the next several months, however, it had occurred to me that, perhaps, I didn't really need to do that at all.  As I saw it, Leah's mom and I did not regularly communicate, and it was entirely possible for me to continue seeing her daughter without hurting anyone.  Getting caught with Leah would have, of course, been devastating, but if DW would have found out, it wouldn't matter to her that Leah was the daughter of a Facebook friend or a complete stranger -- I'd be divorced either way.  And, since I'd long ago accepted the consequences of the sugar lifestyle, it wasn't very difficult to make this choice.

I contacted Leah, who was understandably reluctant to hear me out.  I'd written a while back on the blog of my friend Exa, now a well-regarded "sugar matchmaker," that an attempt to reach out to Leah on a platonic basis just a week after ending the arrangement fell completely flat: "... she was cold and distant, insisting that if I wasn’t going to be seeing her sexually, it didn’t make much sense to have a platonic friendship. In other words, no “arrangement” money, no contact."  Still, I pressed on, saying that I wanted to see her, as before, and try to build an actual intimate connection with her.  I said I'd even like to take her out in public on occasion.  She agreed to see me, but insisted on keeping things in her bedroom for now.  Right, I texted her.  Trust to rebuild, things to discuss around that.  No problem, I thought.  She sent me a picture of herself, in a flowery bikini and sarong.  She explained that she was in Hawaii and would text me after she returned.

The day before our scheduled date at her place, I sent her a text I'd simply felt was appropriate: Have you had a significant change to your relationship status since we last saw each other?  She replied that, yes, she was dating someone, but said it wasn't serious.  I thanked her for telling me, and asked her to tell me if it became a serious relationship because "that would, of course, change everything."  She said she didn't understand, but I said we'd discuss it the next day.

Our date was for 10 am the next morning.  She was to leave her door unlocked, and I'd sneak into bed with her.  For the first 45 minutes, we said almost nothing to each other.  Seeing her in a cut-up football jersey, out of which her beautiful breasts fell, I said, "Wow, look at you."  The only thing she said to me was, "Oh my God, I'm coming!"  It was the first orgasm she'd ever had with me.  The story in my head was that she was super-turned on by this morning encounter.  She explained later that she'd stopped using her vibrator so she could experience orgasm through sex.  The only downer about this sexual encounter was that she was insisting on condoms now.

While lying in bed with her, I began asking her about this new guy she was dating.  She said he was 34, Jewish, lived about 45 minutes away, and was going through a divorce.  She'd met him a year earlier on Seeking Arrangement, and that he wanted a real relationship with Leah.  She said she'd consider it if he were no longer married.  He had no kids.  I asked how long she'd been with him, and she said she'd been seeing him about three months.  "Three months?" I said.  "That means you started seeing him right after we last saw each other.  I thought you said you had no room in your life for dating." She confirmed that, but attributed it to her heavy workload at school, which was now over.  "So that picture you sent me from were with him?" I asked.  "Yes," she replied, giggling.  "I had sex with him the first time there."  I scrunched up my face at her and said, "You made him wait two months to have sex with you?  Why?"  "I wanted to see if he was serious," she said.  Well, wasn't it obvious that a guy who divorced his wife to be with her and looked her up again after a year, ready to date her, was serious?  I sat up and looked at her.  "Oh, Leah, this changes everything."

"What do you mean?"

"You told me yesterday that this wasn't a serious relationship.  But it is.  You wouldn't test a guy to see if he was serious unless you were also serious.  You're in a serious relationship!"

"OK," she said, "but I don't see what that has to do with us."

I now understood why she didn't want to keep things in her bedroom.  She didn't want to risk being seen with me.  "Leah, I was clear with you that I never do these things with women who have husbands or boyfriends.  I made that mistake once before and got terribly hurt in the process."

"So, what is it you want from me, exactly?"

"I want to build an intimate relationship with you, to connect on a level that goes beyond our dates.  I want us to care about each other, and share things with each other.  I know that will take time, that we would need to rebuild trust and learn along the way, and I'm willing to put in that time, but your serious relationship makes that impossible now."

"You're married, Porter."

"My marriage isn't an obstacle to what I want, Leah.  You knew going into this that I was married.  In the beginning you opened up to me, no problem, and we really worked on getting to know each other.  Of course, that was before the boyfriend entered the picture."

Leah sat up and raised her voice.  "You're not making any sense to me.  I just want this to be an NSA thing, where we get together and have fun for a couple of hours.  Are you forgetting that we met on an arrangement site?"

"The same site where you met this guy," I interjected.


"I am investing in this, and so I want what I want."

"Good luck with that.  Porter, you're married and unavailable to anyone except your wife.  It's completely delusional to think that you could have what you're looking for with a single girl.  There are only two reasons why a single girl would sleep with a married man: to get his money, or to break up his marriage."

I swung my feet off the bed onto the floor and reached for my underwear, standing up to pull them on.  I smiled.  "Well, Leah," I said, reaching for my socks, "you're just wrong.  I had a three-year intimate relationship.  I'm sure that there was an element of superficiality there, but I'm just as sure that there was a period of time where I had exactly what I am looking for now."  I started putting on my shirt.  "Intimacy is what makes these arrangements enjoyable and fulfilling for me.  Intimacy makes the sex better, and makes us both better people.  I experienced that, and it was awesome."  I was stepping into my pants now.  "If I can't have intimacy, then this --" I gestured to her and the bed and the bedroom -- "becomes just sex for money, and that's exactly the opposite of what I want.  I know you have no interest in breaking up my marriage, so that means all you really want is my money.  You never gave a shit about me.  I'm such a stupid fool.  You were playing me from day one."  I leaned over toward her, as she sat still on the bed.  "And if that's what you want, fine, but it basically makes you a whore."

I strode into her living room, my footfalls thudding on her hardwood floor.  I put on my ring, my watch, stuffed my wallet into my pocket, and slung my briefcase over my shoulder.  And then I had a thought. I grabbed the envelope I'd left on her coffee table and walked to the front door, past her dog.  "Goodbye, Leah," I said loudly, opening the door and letting it slam as I closed it.

A few minutes later as I sat at a red light, I got a text from her. "You're a fucking asshole."  "Yes," I replied, "one with my money back in my 'fucking asshole' pocket."

I later deleted every text, email, photograph, every remnant of Leah that ever existed.  I also unfriended her mother on Facebook.  The last thing I wanted to see was a post with Leah's picture on it. 

If the daughter of a high school friend, with brains, beauty and a winning personality, can brazenly play me like that, then I am absolutely off track in so many ways.  I've written before that this doesn't work without the money.  Even Leah can't manage to transcend that cynical reality.  And so, I stick with Audrey.  She is no great thinker.  She speaks in an annoyingly loud voice.  She's not even a striking beauty.  And that makes things much easier for me to keep things superficial.  As we prepare for our first swinging encounter with another couple, I feel secure knowing that I have no real attraction to Audrey other than her sexuality.  This is as it should be.

Meanwhile, this truly made me appreciate DW in a way I hadn't anticipated.  That afternoon, I raced into the house after work, kissed my kids, pet the dog, and threw my arms around her and kissed her all over.  "What's up with you?" she laughed.  "I just love you, babe."

Update on My Life, Part 1

Hello, dear readers!  It's been nearly five months since I posted anything on this blog, when I said goodbye to sugaring (and I meant it).  In that time I have essentially stayed 100% clear of the sugar world, although I had a couple of slips.  My sex life has definitely deteriorated but there is hope for improvement in a few areas.

I wrote in my farewell post --
with a renewed commitment to working things through with DW, my heart simply hasn't been in it to continue searching for quality girls.  On top of that, the financial toll it has taken on me and my family to continue doing this has been at times very large.  It no longer makes emotional or financial sense for me to continue in the Sugar Bowl.

This year has been the worst year of my career, worse than right after the economic crash of 2008.  My income is down 80% and I just don't have the means to carry on a sugar relationship right now.  So I have focused on career building and relationship building with DW. 

On the career front, I have an exciting new prospect that will take me out of the business that I'm in right now and set me on a path of senior executive leadership in the next five years.  Meanwhile, I am researching returning to school to earn an MBA and further improve on my chances of securing lasting employment at a senior executive level.  I hope that these moves will put me in a more lucrative path toward retirement in the next 15-20 years. 

On the marriage front, DW and I have grown significantly closer.  We are more intimate, laugh more, agree more on parenting and money management, and disagree far less than we did this time last year.  We haven't really improved in the area of physical intimacy, but we've had a recent development that holds a bit of promise.  DW visited her OB/GYN because she was concerned that sexual intercourse had actually become painful for her.  She wasn't getting wet, and not even lubricants were helping.  She told me, "I know you're miserable, and I don't want you to feel that way."  The doctor's examination showed that, indeed, there was a problem, and he prescribed an estrogen-based cream for her to use daily.  We've had sex once since she began this regimen, and it was more enjoyable for both of us.  Nothing earth-shattering, but certainly it felt good to be close to DW again.

Now, I know you're all probably curious to know about the couple of slips I had since stepping out of the sugar lifestyle.  There were three, actually: two with Audrey, and one with Leah.  With Audrey, we had begun a dialogue, shortly after I wrote my last post, about my financial difficulties and how I wanted to see if we could keep things going between us without a specific arrangement.  She was open to a "friends with benefits" type of relationship between us, but still needed occasional financial help.  I couldn't agree to anything significant, but I could scrape together a little cash each time we got together.  I didn't want to start anything, however, until she had her own apartment.  It made no sense to pay for hotels as well.  She finally got a place in mid-May, but wasn't ready for visitors for a couple of weeks.  She had a cute one-bedroom place on the ground floor of a newer complex, with a patio that overlooked the pool.  The bedroom was cozy and she had a nice queen-size bed.  And two cats -- ugh.  One of them just hid under the bed the second I walked in the door, but the other wanted to be my new best friend, particularly when I was going down on Audrey.  I managed to work around it, but I knew this would not be an ideal situation for us.  Still, it was better than a room at the local Best Western.  The second time, however, she asked me to meet her at her parents' house, since she was still packing up some of her things and was going to be alone their most of the afternoon.  We had sex in their spare bedroom, amid computers and very dated knick-knacks.  A very unpleasant experience for me.  I was so turned off that I couldn't even bear to shower in the house.  As I left, I said, "You know I love having sex with you, Audrey, but I don't ever want to do this here again."  She laughed and agreed.

One good thing that came from these two sessions, however, was that our discussion turned to ways we could spice things up.  Audrey was slightly experienced in the swinging lifestyle, and had participated in threesomes with a few couples.  I asked her if she'd be open to hooking up with another couple or doing threesomes with me, and of course, she jumped at the idea.  We haven't done this yet, but when we do it will be outside of whatever time we spend together.  And there will be no financial terms for that fun.

As for Leah, we had one more encounter which I will detail in the next post, as it led to a huge lesson for me.