Wednesday, September 28, 2016

Sugar Date #3 With Mel -- Exhaustion, an Anniversary, Threesomes, and The Number 100

For my third date with the lovely Mel, three days before our one-month anniversary, I booked the same hotel that I used almost throughout 2013 for my dates with Jade and Elle.  The room rates were about fifty bucks higher, but apparently the hotel owners had used the extra money spruce up the rooms.  Nicer showers, refurbished elevator, better wifi, and more energy efficient lighting.  All in a hotel building that was built in 1927.

Texting her the room number as I boarded the lift, I told her to hurry.  From our room  on the third floor, I could see her walking up the street and entering the rear parking lot.  She'd be just a few minutes.  She walked in the door one minute early!

Mel removed her long silk red dress to reveal she had nothing else on.  Certainly not necessary to wear clothing anyway.  "It's too hot for underwear!" she laughed.  "See, to me that's the best reason to wear underwear," I said.  "No one wants to get near me if I've been going commando all day."

I'd already showered, so Mel did a quick rinse off and joined me on the bed. Our hunger for each other was excruciating, and we tore at each other with all we had.  As usual, Mel gave me an epic blow job, using her hands to stroke me and massage my balls.  Since I didn't feel totally fresh I asked her not to rim me this time, but I told her how much I loved it the last time.  With her long hair pulled back I got to watch her devour me with her lips and tongue. When I was satisfied and no longer able to control myself, I sat up and took her in my arms, laying her on her back before attacking her clit. With her knees drawn all the way back to her shoulders I had full access to her pussy and ass, and I licked away with abandon.  She shuddered and twitched, grabbing her breasts and pulling at her nipples.  Without fingering her I brought her to a huge climax, with her clamping her legs around my head. "Uh," I muffled, "can't breathe?"  She laughed and released me.

I slipped inside her easily, going slow and kissing her body all over and I made sure she felt every inch of me.  With me that deep, Mel grabbed me with both arms and pulled me closer.  We stayed in that position most of the time, until she asked to get on top.  Never one to turn down that position, I lifted her up and set her down right on my dick.  We fucked each other furiously, and Mel came over and over again with her familiar "Feck, feck, feck!" chant.  I pulled out after about 15 minutes and she let me come in her mouth.

I was exhausted.  (I'd been fighting a cold for the last day and knew it was coming on.  Unfortunately, Mel's going to get it next week while she's away on vacation.)  "I don't have anything left," I said, "can we just hang out for awhile?" She and I lay there, naked, and talked about a lot.  Her mom and biological father were never married -- in fact, her father was her mom's husband's best friend and they'd been having an affair -- and so she never really knew her dad.  Having Mel in a hotel room that Jade and I had occupied just three years earlier, knowing that Jade, who is also Filipina and Italian, never knew her biological father, was really too much for me. "This is like a total deja vu for me!" I said, "I just hope you two aren't sisters or something."  I didn't have a picture of Jade to show Mel, but there was no way they were related.

We talked about our mutual desire to have a threesome.  I told her I went back to the sugar website to find someone since I didn't want to go to a swinger's website and find nothing but heavy, older women to play with. Any girl who was fit, hot, and down to fuck would probably be either an escort or some other professional girl.  On the sugar website, I actually found one girl the morning of my date with Mel who was into the idea, but it didn't work out.  I figured the chances were that whoever I found would be just a regular girl who happened to be bisexual.  Mel agreed and wanted me to send her pictures of anyone I thought would be a good choice.  So, armed with that vote of confidence, I told her I'd probably find someone in the next couple of days or so.

The night before our date, while out walking the dog, I reflected on the fact that I'd been with 51 different women since deciding to become a Sugar Daddy way back in 2008.  That was quite a lot, but I began to wonder if I could remember every girl I'd ever been sexual with (I defined that as fucking, hand jobs, blow jobs, or genital touching of any kind.  Kissing or making out didn't count). In my mind I started compiling a list.  I have a steel trap memory, and I was able to remember every single sexual encounter I'd ever had, from the first girl I'd ever had sex with when I was 18 (and who died a little over a year ago after a long series of illnesses), through my first wife, through all the street hookers and escorts, co-workers and bar hookups, interim girlfriends, DW, more escorts, and then potential Sugar Babies and actual Sugar Babies, I concluded that Mel was actually the 100th woman I'd ever been sexual with in my life.

When I shared this with Mel, she seemed genuinely moved. "I feel like I won a prize!" she said. Well, she did, but I said, "Mine's the bigger prize, actually."  And I meant it.  The connection between Mel and me feels closer to the one I had with Jade (when things were good) than with nearly all the others.  Of course, I don't think I'll ever repeat what I had with C/Hayden.  A little over a year ago, I wrote:
I could blame all these women ... for all the shit they pulled (Jade, in particular), but the real truth of it is, I cannot see the particular conditions that led to all that happened between C and me happening again.  Back then, I lacked the experience and wisdom to know how the Sugar game worked.  I didn't really know that none of it worked without the money.  I naively believed that real emotions were possible within the context of that kind of relationship.  But after C's departure, and subsequent revelations about her true feelings toward the end of our time together, I find it impossible now to trust any of them fully.  The money does its part, of course.  I can never fully trust any woman who consents to spend time with me only if I invest in their lifestyle/bills/ whatever. 
That remains true today.

So the search now begins for a threesome partner.  I have already spoken to two different women about this and one has already enthusiastically consented.  More about her in the next post.

Friday, September 23, 2016

Loving These Blogs

I ran across these two blogs in my Twitter travels.  I love them both.

The Unexpected Hobbyist is about a man in his late forties who, caught in a sexless marriage, gets a free pass from his wife to have sex with other women.  He then chronicles his experiences as a hobbyist, or a frequenter of escorts.  From there he veers into Sugar, where he meets a special woman.  I believe his posting is largely over after a year and a half, but start from the beginning and read all 197 posts.  He tells a very compelling story, one that I couldn't stop reading for 24 hours until I got through every single post.  After reading it I see escorting through new eyes. But the conflicts he has over what to do about his marriage were most compelling for me (gee, I wonder why?).

Vegas Sparkle features posts from a 28 year old girl who has been corresponding with me for a little over a year.  If you remember the post from a about a month ago, where I apologized for an insensitive Tweet about my impatience with Sam for canceling a date because she got her period, it was prompted by some pretty harsh shade she threw at me for being a dick.  I was a dick, not very considerate, and I sincerely apologized.  She accepted, but she confesses she no longer reads my blog.  She told me today that she doesn't believe I've slept with fifty SBs, but perhaps five SBs and 45 potential SBs.  She's probably right, although I don't really see it as her way. She thinks I dispose of women too easily.  It's not really true, at least for the past two-plus years.   Anyway, her blog chronicles her life in Vegas as a student and worker, trying to find a sugar daddy but not succeeding, but becoming comfortable with her body and sexuality (she is still a virgin though she has given at least one blow job in the past year or so).  I loved what I read, because she has a great imagination and a pretty sharp wit; I hope she continues.  And comes back to reading my blog.

Third Sugar Date with Mel -- Preview

Mel and I have a scheduled date -- our third -- in just a few short days (well, long days if you're me because I really can't wait to see her).  We're meeting for coffee about a block away from our hotel to spend some quality chat time. 

To be honest, it took some convincing for Mel to meet me outside of the hotel room.  It's not that she doesn't want to be seen in public with me.  It's that she has a pretty serious appetite for sex, and who needs to talk when fucking is so much more fun?

"Just a few more days till I get to feel you inside me," she texted a few days ago, throwing in a bunch of emojis to emphasize her excitement.  We have definitely responded to each other's skills in bed.

I replied that I'd been thinking of her at the exact same time, and that I couldn't wait to see her again. "Woo hoo! We're connected," she said, adding, "I love my afternoons with you!"

"If this is how strong our connection appears to be after only two times together," I wrote, "just imagine how it's going to feel after, like, 22 times together."

I think I've arrived at the point where it feels right enough with Mel to discuss a couple of things. First, I want to offer her a monthly allowance.  While I don't think a per-meet arrangement is a bad thing, I can understand how some think it blurs the line between sugar dating and escorting. However, I think it all depends on how a Sugar Daddy holds it.  My entire three-year relationship with C/Hayden was per-meet.  At the time I was making roughly half of what I make now, and cash flow was important for me to be able to support my family.  I managed to be able to eke out enough cash to give her what I could, and C/Hayden was fine with spreading things out on a per-meet basis.  She never once asked if I'd provide the allowance monthly because she knew I didn't see our relationship as transactional.  You can read here how differently I view escorts and Sugar Babies.  Even though this was written three years ago, it still holds true, at least for me.

Second, I want the monthly allowance offer to lead to a discussion of seeing each other more often. Neither of us is seeing anyone else right now, and it might be fun to see her weekly.  And, even though I keep Sam in my back pocket for when nothing else is happening, she's not responding to texts of late so I think she's probably gone for good.  I don't know how Mel will react to such a discussion, but if the monthly allowance discussion doesn't easily lead us there I won't force the issue.

Confession time: I've had such a hot time with Mel just these past two dates that I engage in "self-help" while recalling the sex we've had.  Further, I am fantasizing about certain things I want to do with her, and I have mind-blowing orgasms every time.  I'm getting hard right now just thinking about her.

Friday, September 16, 2016

Another Death in the Family -- A Reflection

My uncle died two days ago.  He was in his mid-80s and had a really aggressive form of cancer that had spread rapidly all through his body.  

I hadn't seen my uncle in more than 25 years, at a sibling's wedding.  It could easily have been nearly 40 years, at another sibling's life event.  I honestly can't remember the last time I saw him.  While he was totally estranged from his siblings for the last 10 years or so, that doesn't tell the whole story.  

We were never really close. Relatives remind me that he and his family were present at summer holiday parties when we were kids, but that probably stopped before I turned 13, about 40 years ago. I didn't get along with his two kids, my cousins.  One was a bully and the other really quiet and retiring.  When my family made the pioneering move out west two years later, leaving literally everyone else behind, visits with relatives became annual, then biannual, then only for special occasions, like when my dad's parents celebrated their 50th anniversary.  I don't remember if my uncle was there, but if so, that would have been nearly 35 years ago.

His death, and the distance in years and miles that were between us all that time, made me think of my secret little life as a Sugar Daddy.  I've created relationships with dozens of young women since 2008, and over time all of them have moved on, or will move on, and written, or will write, many new chapters in their lives.  I wrote a little bit about this a few weeks ago, relating the scant knowledge I had about some of the Sugar Babies I've known over the past eight-plus years.  Granted, none of them ever rose to a level where I could comfortably compare them to my uncle in terms of closeness -- well, perhaps just one, C/Hayden -- but I began to think about where I'll be in my 80s, and whether or not any of these young women will care how I am, or even remember that I was there.  

Would C/Hayden, when she's in her 50s, have a single thought or memory in her head if ever told that I had passed?  Certainly, if any of the Sugar Babies I've known would remember anything, she'd find something in the three years we knew each other to make her think, or (I hope) smile. I know I'll never forget her.

Do I now want to go back and reconnect with my cousins?  They're both in their 50s or late 40s as well, and I've learned over the years that they have kids and jobs and spouses, and ex-spouses.  The answer, honestly, is I don't know.  One of them accepted my Friend Request on Facebook the day after my uncle died, and I've learned that we are polar opposites with regard to politics, which didn't surprise me.  Still, my experience reconnecting with old high school friends and acquaintances, which has been mostly awful (reminding me why I never attended a single reunion), informs my thinking today about my cousins.  I guess it's wait and see for now.

I'd love to reconnect with C/Hayden in 10 or 15 years.  Audrey too.  I prefer my world smaller, don't you?

Tuesday, September 13, 2016

Sugar Date #2 With Mel -- Pets, Showers, Healing, and Rim Jobs

For a change, I was the one who was late.  Mel sent me a text about half an hour ahead of time, right before I left the office, that she'd already arrived and parked across the street from our hotel and was shopping at the mall there.  I sent a text while stuck in traffic that I'd be 10-15 minutes late.

The hotel sits across the street from a landmark shopping mall in the center of the city, where traffic is usually quite heavy and parking a nightmare.  Overnight guests at the hotel must pay about twenty bucks to park at the hotel, and that's on top of the room rate, taxes of about 15 percent, and a five percent "resort" charge (for a hotel that has no resort amenities whatsoever).  Even though I was not going to stay overnight, I could not find street parking, as neighborhood streets all had posted "No Parking Without Permit" signs everywhere.  The parking ticket would cost me more than the room. Ugh.  I had no choice.

I checked in and sent a text to Mel with the room number.  "Hurry," I added.

The room made me smile immediately.  Great appointments, large bed, with funky decor, including a floor to ceiling mirror (that was, unfortunately, not anywhere near the bed so we could watch ourselves).  I'd use this place again, I thought.  I left the door ajar.

Mel arrived about three minutes later, locking the door behind her.  I noticed her sweet perfume as we hugged.  "Sorry, I look like such a scrub," she said, indicating her yoga pants, sports bra and tank top. "Don't be silly, you look beautiful," I said, adding, "just get naked already!"  I turned and started undressing as well.  I turned and she was down to her black underwear, showing off her dark tan and curvy, tatted body.  "I need to rinse off, is that OK?" she said.  "Sure," I replied, "I could use one too, let's go together."

We showered, kissed, and soaped up.  She stroked me till I was totally hard.  After rinsing off, we were on the bed and playing.  She started going down on me immediately. Dear readers, Mel has formidable oral talents!  Such a slippery, slobbery mess.  She kept venturing further down, sucking my balls and stroking me. Not knowing if she'd take the bait, I opened my legs further and slightly tilted my pelvis upward.  She took it, alright!  I got the most intense rim job I've ever had.  Not only was she circling her tongue around my back door, she got most of her face involved.  At one point she came up for air, revealing that her mascara and eye makeup had completely smeared all over her face. She looked like the sexiest clown I'd ever seen!  "You're going to have to wash makeup off from between your legs," she warned, giggling.  She resumed her rimming, and I resumed my moaning and twitching.

Mel got me to the edge of orgasm three times.  The first time I settled myself down, but the other two times I took hold of the hand that was stroking my throbbing dick and stopped her.  "I'm not ready to cum yet," I said. "It's OK," she said, wanting to take it further and make me cum. It was hard to resist her but I persuaded her to let me have a turn on her.  She got up to rinse her face and remove her makeup, then came back to the bed.

I have to say, Mel has one beautiful pussy, and I love eating her out.  She just closes her eyes, putting her hands behind her head like she's going to start doing sit-ups, and slowly rocks her hips in rhythm with my tongue and fingers.  I made her cum three times before giving her time to recover.  "Whew!" she laughed.  "You're really good at that!"

After grabbing a sip of water, she came back to the bed and went down on me again to slick me up. She just got on top of me and put me inside her, bareback.  I wasn't going to complain, was I?  She rode me pretty hard and fast, leaning down to me and putting her face on my shoulder.  I got to the edge again after just a couple of minutes, so I put my hands on her hips to slow her down and exert a little control.  "If you're going to cum just, you know, throw me off of you," she said.  After a few minutes of this really slow, grinding sex, she came again, and it was super intense.  Properly relaxed now, I resumed the pounding.  "Feck, feck, feck," she said, over and over (I realized later that her east coast accent, combined with whatever she'd picked up living on the west coast, created this little linguistic phenomenon).  She came again, at least twice.  As I neared the point of no return, I quickly picked her up off my dick and set her beside me.  "Whoa, OK," she said, as she watched me grab hold of my cock and stroke away.  When I came, the jizz just shot out of me like I'd released a kink in a hose.  It was unexpected, given my meds, but I sometimes ejaculate when my arousal level has plateaued at an intense level for an extended period of time.  "Old Faithful!" she joked.  I babbled something about how good that felt and collapsed, completely spent.

We cleaned up, drank some water, and chatted.  I learned that she's going to start looking for a new job.  "I don't really make that much, and there's really nowhere for me to go there," she said.  She has a five year plan to change careers entirely, during which time she'll study and get degrees in eastern healing practices like acupuncture and Reiki.  I hope to be able to get her part of the way there, I said, which got her smiling and throwing her arms around me.  

Mel also talked a lot about her dog, whom she named after a relative because the dog looks like him. The dog had a couple of cancerous tumors recently, one of which she claims to have healed on her own after attending a Reiki seminar and practicing the little techniques she learned there.

Taking a quick glance at the clock, I saw we only had about half an hour left before I needed to head home.  So we had sex again, this time with me fucking her from behind most of the time.  I pulled out again when I came, leaving a drip or two on her butt.  "Did I miss the show?" she asked, wondering if I'd blasted again.  "Not much of a show this time, I'm afraid," I smiled.

After cleaning up and dressing she was out the door, a little bit richer and a lot happier.  I was feeling so good while I showered, I could help but take my time washing her smell (and her makeup) from my body.

Later that night I sent her a text that perfectly encapsulated how I was feeling with her:

We've decided to see each other every other Monday.  Next date, we're going to take pictures for a swinging website so we can meet available single women for threesomes.  We're also going to celebrate my birthday which is next week.  Finally, I'm going to bring up going with a monthly allowance instead of per-meet.  I'm feeling very good about this girl and hope we can keep things going.

The Latest Downtown LASD Post on Let's Talk Sugar -- Managing Expectations

I love writing! Coming up with things to talk about each month is easy. This month's installment, about managing expectations, came to me after my first date with Mel.

Find the post here.

My next post will be about my second date with Mel and all the fun we had!

Wednesday, September 7, 2016

New Sugar Daddy Posts Coming Soon!

Greetings, dear readers!  It's a beautiful day here in sunny SoCal, and I've been hard at work earning all those ducats so I can continue to lavish affection and Benjamins on my newest Sugar Baby, Mel!

Mel and I connect very well.  As I mentioned in the previous post, she's a low-maintenance kind of Baby, who doesn't want or need expensive gifts, out of town travel, or even super-fancy hotels for our dates.  As a woman with a decent job she makes enough for rent and bills, but when times were tough she got in debt and now needs help to dig out.

Aside: you will recall my feelings about Sugar Babies who can't manage their money, but having credit card debt alone isn't the issue.  With the Baby Who Had No Name, she was so deeply in debt, despite a near-six-figure income, and wasn't taking substantive steps to curb her spending habits so she could live more within her means (sugaring is, despite what many Sugar Babies will tell you, not a very stable source of cash flow).  With Aussie, she was living off of savings until she'd gotten a job, and when she did get a job it turned out to be a really bad choice, and she ended up flat broke.  No amount of sugar was going to help her make better choices around work.  And with Chic, getting her car totaled sort of derailed her to the point where not even my offer to rent her a replacement car added any value.  The issue isn't just having debt, it's not having a solid mindset of being disciplined with money.  Mel, so far, has not shown a propensity for being undisciplined.  Like C/Hayden, she has a dog to take care of, which in my eyes makes her inherently more stable.  Most people don't adopt pets if they lack the means attend to them.

Mel and I have our second date next week, and the third two weeks after that.  Next week I've booked a room at a funky hotel in the center of town that has retro features like mirrored ceilings and reclining chairs.  Should make for a fun experience!

Also, I have my next piece on Let's Talk Sugar coming out next week, covering how to go into an arrangement being open-minded and with no expectations.

Finally, for something completely different: I follow an adult performer on Twitter who produces her own content.  One way she pays herself is to raffle off the chance to do a scene with her, complete with professional camera crew.  I've watched a few of these scenes and she is adept at keeping her partners' faces off camera if that's what they want.  I have no distinctive tats and my voice and body aren't all that unique (I'm very well endowed but that's not unique in porn), so I bought eight tickets. She probably sells a couple of hundred tickets, so I don't have great odds, but it's worth $100 to see if I can meet and play with this cutie pie.  Even if I lose, she'd still do a scene with me for $2,000. Might actually be worth it if I can keep a copy!

Stay tuned!