Friday, October 28, 2016

WCSD Journal Update: Who's In, Who's Out, Who's New

Happy Friday, dear readers! I enter this weekend prior to Halloween hosting out of town relatives, enjoying some great Chinese food tonight, great Italian food tomorrow night, great bagels for Sunday brunch.  Meanwhile, one kid has intense athletics practice and the other some serious plans to indulge a favorite hobby/passion.  DW and I will continue to build intimacy, but we will hold the celibate line ,as we have since January 25, 2015.

Meanwhile, in my Sugar life, the girls are moving in and out of contention.  Here's an update:

Who's In
Mel -- still my #1, still my lover, one of the best partners I've ever had in eight years
Crystal -- holding steady at #2 now that MJ turned out to be a skanky ass escort.  I'm starting to get concerned that her four jobs -- office manager, part time massage therapist, part time makeup artist, and full time MOM -- are going to get in the way.  We scheduled a tentative date for mid week next week.
Harmony -- has moved out of borderline out territory.  This cute Asian bikini dancer has been reaching out since our phone call last week, and asking some great questions designed to get to know me better.  I find both the reaching out and the inquisitiveness parts very attractive.
Jewel -- My neighborhood girl.  She wants to get together for lunch next week and understands the need for a face to face meeting before hooking up.  However, she has some immediate financial needs that are showing up as a sense of urgency in her texts to me. A bit of a turnoff, honestly, but I'll indulge it awhile.
Shelly -- Still liking this MILF.  Trying to make time to see her next week, but not sure yet.

Who's Out
Chloe -- After the total failure with MJ, I spent yesterday in a foul mood most of the time. While sitting at home last night and going through the text messages I've been exchanging with all these girls, I saw that I hadn't contacted Chloe in four days. I figured that was longer than I'd been out of touch with all the others, and I just immediately deleted the entire text thread, losing her phone number with it. If she wants to see me she'll reach out, but I'm just tired of chasing so many. Harmony, with her taking a more active approach, kind of knocked her out, actually.
MJ -- obviously

No one new, thank God.

Last night, Linda expressed some regret and jealousy.  Regret that I might have felt a little upset by her needling me about the MJ disaster, and jealousy that I'm choosing to invest in local talent rather than splurging to bring her out west for fun. I adore Linda, but I told her on Wednesday that she and I were in "the friend zone" and I could no longer see getting sexual with her. I sent her a text last night that made it very clear: "I really don't think it serves you or our friendship to continue to suggest we hook up. Luv, ya, but it's not going to happen."  She replied, "Ouch..." which I hope was just a little bit of a joke.  We'll see what develops next, but I trust our friendship will hold steady.

Thursday, October 27, 2016

It Had to Happen Sometime! Part 2

I had just had the Worst. Fuck. Ever.  MJ, the escort posing as a sugar baby, bid a hasty retreat from my hotel room, never to be seen or heard from again.  Good riddance!

Except now that I was lying there, naked, on the hotel bed in a darkened hotel room, less than thirty minutes after she'd arrived, I was now feeling depressed and dejected.  I'd had high hopes for this girl, and she dashed all of them, like a boss.  I needed to talk to someone about it, but there was no one who could understand. I did, however, have a sugar friend on the East Coast, Linda.  I sent her a text via Google Hangout, the way we always communicated. She asked, "When are we ever going to talk on the phone?"  I was in the mood to talk, so I sent her my number.  She called and we talked for about 20 minutes before my phone nearly ran out of battery.

What I'd hoped for was some sympathy, but instead I got laughed at, for the most part, with a cursory sprinkling of sympathy. "You see?" she said. "You coulda flown me out there and I woulda shown you a great time," but instead I had to fuck some skanky bitch.  While she was on her way to getting drunk, Linda was still right to a point, except that the talent pool in my city is far too deep to look elsewhere for suitable companions.  I just happened, unfortunately, to step in the shallow end of the pool this time.

After the phone call, I washed up thoroughly to get the smell of that rank, stinky pussy off my body. Once dressed, I headed home.  That night, I got myself off watching the video I'd shot of me and Staci, and got a good night's sleep.

My experience with MJ truly ranked as the worst sex I have ever had with a woman.  Even those experiences where I came in 10 seconds (when I was 18 or 19) were better than this.  I was reminded of previous experiences I'd had, ranked as the Bottom Five of Bad Sex:

5. Fleur -- her allowance was far lower than MJ's, and she was actually intelligent and funny, even though she was a total dud in bed (I did come while fucking her though);
4. Paulina -- she was even more of a dud than Fleur, but I did get to come while fucking her;
3. Julie -- an escort who got less money than MJ, but who was a total zero in bed (major deductions for also bleeding on me);
2. Ally -- a Craigslist escort I visited in summer 2008 (never wrote about her) who did nearly the exact same stuff as MJ, plus asked me constantly if I was ready to cum and started booking her next client before I got off the bed to wash up.

I'm not really one to beat myself up too much over bad experiences. I'll feel my feelings, to be sure, but it doesn't take me long to start looking all around for lessons to be learned.  That's one of my takeaways from my time spent in a recovery program. So, if I had to identify any lessons from this experience, one would be that the Sugar Dating website I frequent has more people engaged in a deceptive hustle of some kind or other than I think.  Another would be that if a woman on that site pushes for an immediate meeting for sex, chances are she's probably an escort.  Any woman I encounter in the future who angles for first-meeting sex will be rejected.

I also resolved to make a few changes: First, I will insist with every potential Sugar Baby on a casual, no-allowance first meet. Since escorts and other sex workers live on the clock, this change will weed out nearly all escorts, as well as those girls who want "a gift" to audition me as their potential sugar daddy. Second, I'll update my profile to let anyone who sees it know that a casual, no-allowance first meet comes before sex. As I've regularly shared my allowance terms in text messages, it should be appreciated that I care about chemistry rather than just pussy.  Finally, I downloaded Google Voice today and have added a "burner" number to my phone, from which I'll send texts and make phone calls.  This way, all future potentials will never know my real phone number.  I honestly can't believe I didn't do this a long time ago, but better late than never.

Having purged MJ's texts and pictures from my cell phone, my gaze now shifts to the lovely Crystal, with whom I'll be trysting next week.  I've met her, matched her face and body with her pictures, and created a decent rapport. Should be a lot of fun!

It Had to Happen Sometime! -- Part 1

Worst. Fuck. Ever.

I'd had such high hopes of having a fantastic time with MJ, who met me at a hotel yesterday afternoon.  After all, her profile was great, her pictures were amazing, and she appeared to have a cute sense of humor around our first meeting, declining a lunch because she was "on a diet" (which I interpreted as she just wanted to fuck).  God, was I all wrong about her!

She showed up, on time, dressed in a short black dress and high heels, her long light brown hair down nearly to her waist.  She had very long legs, which matched one of the pictures she'd sent me.  Her face wasn't exactly like the one in her profile pictures, but that didn't bother me too much because those were lit a bit dark and she looked enough like the girl in the pics to satisfy me.  However, I will say that I was slightly disappointed.

It all went spectacularly downhill from there.  After coming in, MJ gave me a hug and asked if I could adjust the lighting.  She wasn't particular, but she didn't want a light on next to the bed.  I took care of it, and then she sat on the bed for a few seconds while we made what felt like a feeble attempt at small talk. She told me that she's studying to get a certification to be a life coach. Honestly, that's all I remember her telling me. "Is there anything you need?" I asked.  "Nope, not really," she replied, "just the money."  Thinking nothing of this request -- it's fairly common for new sugar encounters to begin with her asking for the money -- I handed her the envelope.

What. A. Mistake. (Yes, I know I've employed that cliched trick of punctuation twice in less than 300 words; believe me, there's a point to be made here.)

"Well, I guess I should get undressed," MJ said, standing up and making her way to the bathroom, purse in hand with envelope inside.  Hmm, I thought to myself, this will be a one-time encounter for sure. She's got zero personality.

I didn't take off my clothes, preferring instead to have her undress me.  I was in a playful mood and I wanted to get the most out of this.

After MJ emerged from the bathroom, fully naked except for her shoes (which I asked her to remove), she sat on the bed and we talked for a few minutes. I realized after a moment or two that she was waiting for me to engage.  This had started to feel very much like an escort session.  I felt terribly disappointed.  Should I tell her to leave? I thought. She already has my money, and I'm certainly not going to get it back without an argument. Might as well see what's up, I decided.

I got off the bed and removed all my clothes.  "Wow," she said, "that's a really big dick."  She touched it for a few seconds and I got semi-hard.  She was hesitating for some reason, so I thought I'd get her in the mood.  You have to understand that I hadn't fully decided this was an escort session, so I figured giving her a little of my special oral talents would loosen her up.  I sat up and leaned in to kiss her, getting a very perfunctory kiss on the lips.  "Hmm," she said.  "Let me do you," I suggested. "Oh, no," she replied, "I don't need any, um, head.  Besides, I'm a little close to getting my period, so I don't feel so..." she let her sentence trail off.

Knowing that I wasn't going to give head, I nevertheless persisted with me getting head. She moved her long hair out of the way and started to suck me, which wasn't half bad.  Once I was hard, she said, "Wanna get your, um, thingy?"  "You mean the condom?" I said.  "Well, yeah," she said, "you're hard."  Fuck me, I thought, she's a hooker.  She reminded of a hooker I saw about eight years ago, right as I was beginning my sugar daddy journey, who insisted I fuck her the second I was hard, and also kept asking me if I was ready to cum yet.  "I'm liking what you're doing so far," I said, lying so I could get more sucking in.  She, however, wasn't quite going for it, but she stroked me a lot and it felt really good.  Hookers gotta have good hands, I guess.

After I was suitably hard and, frankly, bored with her hand job, I got up to get the condoms and lube. "No lube," she warned.  "OK," I said, "but you're gonna wish we were using it."  "I use only coconut oil," she said.  MJ was the second girl to tell me that, after Rose brought it up when we were together. I guess I'll look for a really small bottle of it.  Not that I need it with Mel.

Once the condom was on, I asked her how she'd like to begin.  As she requested, I entered her from behind.  Unfortunately, from this position, I could tell she was very close to getting her period.

Stinkiest. Pussy. Ever.

I kept looking down to see if she was bleeding me, which caused me to lose any interest in fucking this dry hole.  I tried other things to arouse myself.  I reached around to stroke her clit -- dry, and her pubic hair was stubbly all over.  I tried squeezing her tits.  They were wonderfully natural and felt great in my hand, so that helped a little.  I noticed, however, that her nipples did not feel as large as they looked in the pictures she sent, further confirming for me that she sent me fake pictures.

I pulled out and had her flip over.  I confirmed that, in fact, the topless girl in the picture she sent was not MJ.  Entering her was more difficult because she also had the Driest. Pussy. Ever.  After less than a minute, I pulled out again and stopped.  I'd had enough.  "It would be nicer if you were enjoying yourself," I admitted, slipping off the condom and placing it on the nightstand. "You're totally dry down there."  "Wow," she said, examining her pussy, "I think you damaged my hole.  It's wide open." "Oh, it'll be alright in a minute," I said, completely disappointed.  I lay down on my back and she offered to finish me off with her hands.  I took her up on her offer because that was literally the only thing that felt good with her.  It took a few minutes and I came.

She got off the bed, saying that she was just going to wash her hands.  However, I saw her take her purse again, which confirmed for me that she was going to get dressed and leave.  Sure enough, about three minutes later, she emerged from the bathroom, fully dressed.  "Are you going back to work?" she asked.  "No," I replied, "I'm done for the day.  But it looks like you're going back to work." "What?" she said.  "Well, you're leaving, aren't you?" I said, resigned to the waste of time and money. "Well, you came," she said.

As I explained to her that this was the worst sugar meet I'd ever had, she tried to explain that she'd never done this before and she thought I just wanted to get together for sex.  "I offered to buy you lunch," I said, "because that's how we get to know each other first. If I'd known you'd be such a bore, I would never have agreed to this." Of course, she didn't like that.  "OK, I'm gonna go now, bye!" And with that, she was gone.

-- to be continued --

Tuesday, October 25, 2016

Settling In With Mel

Mel and I saw each other for the fifth time yesterday afternoon. Apart from the volcanic sex we had, which I hope happens every time we're together, we also reached an understanding about our relationship.

Mel continues to say that I'm the best lover she's ever had.  Judging by how many times she cums when we play it's pretty obvious that she really enjoys herself (and that I've got mad skills in bed!). While lying together in our spacious room on our comfy bed, I called her out on a few things that had been eating at me since our last time together -- which was the spectacular threesome we had with Rose.  I wrote about it a little bit in the follow up post, but I think Mel was not as enthusiastic about how our threesome went, and about having another woman in bed with us at all.

Mel continues to say that she had a good time with Rose and wasn't bothered at all that I fucked Rose after Mel left.  But I made my case anyway. "It just struck me as odd that you would make a comment at all about how Rose can't cum without a vibrator when, at most, we'd see her one or two more times," I said. "Did it really make a difference how she gets off with us?  Or even if?"  Mel then copped to not having the feels for Rose.  "Well, I just didn't get that connection with her like I do with other women."  Of course, I told her that was OK. "We won't be seeing Rose anymore," I told her.  "No," she replied, "if you want us to hook up with her again, that'd be OK, but it just won't be the same as with someone I really like."  I told Mel I appreciated her willingness, but the threesome has to work for both of us or it can't work at all.  Basically, I thought to myself, if I want to fuck Rose again, I'll have to do it on the side (maybe her friend CJ can join us), and not tell Mel about it.

On that front, Mel wants to revert back to condom use if I'm going to fuck other women, and I agree with her.  No sense in putting anyone at risk with all the STDs going around out there.  Mel happens to be a bit phobic of them; as long as I test regularly there should be no problem, but I'll accede to her wishes because I like her and want to continue seeing her.

Mel and I didn't take our own feelings for each other too deep.  It wasn't something we were ready to discuss, though we did look into each other's eyes a lot.  When we had sex the second time, she took me in her mouth completely limp and got me super hard again.  She playfully asked, "Can I sit on you for a little while?"  "You don't even need to ask, silly girl," I said.  It didn't take very long before I was ready to cum again.  This time she didn't take me in her mouth, as she had the first time I came. Instead, she watched me jerk off.  When I climaxed my body went through all the motions of having a huge orgasm, but I didn't ejaculate a drop. 

"Ha!" I laughed, "You finally saw what I've been talking about." 

"Did you feel the same way as if you would have ejaculated?" she asked.  

"Exactly the same."

"Wow, I've just never seen anything like that before."

"Took getting used to for me," I said, "but it's the best 'cuz there's no mess to clean up after."

We had completely run out of time, so we said a quick goodbye and I stayed behind to shower and clean up.

There's no doubt I'll see her again in a couple of weeks.


MJ is failing to impress me. I've never hooked up with a girl I hadn't spoken to first (actually that's not true -- there was The Dancer, with whom I'd only exchanged texts and pics), and I told her I wanted at least a short phone call before we met for sex later this week.  She agreed and gave me a time, but when I called, she didn't answer.  I didn't even hear her voice on the outgoing message; it was just some shitty dance music.  I left her a message, and gave her a time when I'd be available, but she didn't call back.  She texted me this morning and I gave her more times for her to call.  If she doesn't call me in the next couple of hours, I'm blowing her off.

Crystal could have been a backup for tomorrow, but she's not available till late in the day.  We're still set for next week.

Jewel is back in town and we exchanged messages today.  She lives in my neighborhood.  You've read before what I think about having a sugar baby live so close to home.   I'm still concerned about this, but because Jewel can't host, I can have her meet me in another part of town.

Someone New:  Shelly is a mid-30s single mom with a young kid under 10, who lives about 30 minutes away.  Can't host either, but what's different about this girl is that I found her on a different sugar website that I'd been checking out, called Sugar Models.  The site's pretty similar to my regular site, but one neat feature is that daddies can get 20 free messages without paying for a membership. I've been very frugal about those messages, since there aren't a whole lot of women on that site yet. Shelly found me, so I was able to say something like, "Hey, babe, profile looks great! Here's my number if you're interested in chatting further." We've been chatting for a few days now, and it looks like we'll meet casually in a couple of weeks.  She's a tall blonde with blue eyes and a really cute face and a slender body.  I think we'd have fun together.  

Another Someone: Madge is a tall, slender, working fashion model who has no need for my money. She went straight to sex talk from the get-go.  She calls herself very kinky, so I laid out my boundaries right away. Didn't seem to sway her at all.  Early-20s, strawberry blonde to redhead, and a "light smoker," I'm ambivalent about her for a number of reasons.  Despite the fact that she's got an amazing body and beautiful face, she is quite "bushy" and I am just all that turned on by it.  Still she looks like a young Madonna (hence the name I've given her).  If I can get past these little hangups, who knows? As for the sexuality, I like an assertive woman, so we'd just have to see if she's really dominant in bed too.  I do like me some red hair too.

More later!

When to Have Sex with Your Sugar Daddy

My third post at Let's Talk Sugar is up, called "When to Have Sex with Your Sugar Daddy."  The editors did a great job with this one, I must say.


Friday, October 21, 2016

WCSD Journal Update -- Who's In, Who's Out, and Who's New

Now that my lunch with Lauren is over, and my connection with Phoebe is over, it's time for an update:

Who's In:
Mel -- We have a date for Monday afternoon.  She and I both have things to discuss with each other. There will no doubt be some intensity from that, but I hope that it is mildly intense.
Chloe -- I haven't contacted Chloe since we had drinks earlier this week, but I will reach out before day's end.  She is definitely someone I want to see again.
MJ -- We have a date for Wednesday afternoon.  She'll be coming to my neighborhood rather than me going to her, which will save me time coming home.  I sent her a text this morning to get her buy-in, writing, "Should we have lunch first? Or are we just gonna get busy?  Either way is fine with me." Her response was classic: "I'm on a diet."  I looked up some Spanish phrases online and came up with a great response: Voy a devorarte, which means, "I'm going to eat you up."
Crystal -- Having broken bread with this sweet and lovely single mom, I'm more convinced than ever to enjoy some quality time between her legs.
Aurora -- She and I are still trading texts and I'm trying to set up a one-on-one date with her.  Not sure if that will bear fruit, but she definitely looks like she's got the goods to show me a good time.
Harmony -- This cute little Asian doll works as a bikini dancer, and has sent me several great pictures of her body. She's got a tight little booty and small breasts, and looks good enough to eat. Spread some Sriracha on her and let's go!

Who's Out:
Mo -- I'm done straddling the fence with the porn starlet. Given the talent in the Who's In category, I'm unconvinced that I ought to pony up additional funds to spend time with a woman who in real life looks far less attractive than her on-screen persona.
Phoebe -- See my previous post, reflecting on orgasm.
Lauren -- My lunch with her was pleasant enough, but she was not nearly attractive in person than in her pictures.  I learned during lunch that she has trained as a makeup artist, so the pictures she posted on her profile were the best she's probably ever looked.  Her blue eyes are lovely, but Megan Fox she ain't, not by a long shot.  A little too thick, everywhere.  I'll wait a few days and then say no thank you.

Who's New:
Jewel -- Early 20s, brunette college cutie. She and I exchanged initial messages, but she stopped responding so I gave up. Apparently, she didn't, and she reached out today. I left her my number.  If she doesn't text me in a week, I'll know she's a flake, but damn, she's cute.

A Reflection on the Orgasm

When I was about 12 years old, I remember horsing around with a girl I knew, wrestling on my bedroom floor, and giggling.  We were in our swimsuits, having recently just gotten out of the pool and going upstairs to listen to some music.  I hadn't noticed at all that I was that aroused, but when I gained control during the wrestling match and was on top of her, between her legs, I held her there with my entire body.  She was giggling, and telling me to get off of her, but I was noticing something happening between my legs.  I had no idea what actually was happening, but it felt really, really good. Within a few moments, my hips started moving to add some rubbing against her, and it wasn't long before I felt my entire body twitching and tensing, particularly my penis. When I got up after the sensation subsided, I looked down and noticed this white goopy stuff on the outside of my swimsuit and on her stomach.  My friend asked me what it was, but I had no idea.  We just wiped it off with a towel and we went back downstairs.  All I knew at that moment was that I had to experience that feeling again, as soon as possible.

At some point after that I'd discovered how to re-create the circumstances of that encounter with my friend.  Using a spare blanket, which I'd wadded up to resembled my friend's open legs, I'd take off my clothes and rub against the blanket.  In a few minutes my body would tingle everywhere and the blanket and my stomach were covered with this sticky mess that came out of me. Despite the mess, all I could think was, This. Is. Fantastic.

I can honestly say that, since those innocent days of discovery, I've had an orgasm practically every day, and frequently multiple times per day.  The last one was just last night. Because of the meds I take, the mess is almost always gone, but the sensation remains and I absolutely love how my body feels -- before, during and after.  Add the more than 100 women I've been with over the years, and the emotional bonding and connections that inevitably develop (or don't), and the whole orgasmic enterprise gets elevated -- at least in my mind -- to something akin to a spiritual practice.

I wrote the story above, dear readers, as a contrast to an experience I've had over the last 24 hours. You will remember from two previous posts the indecision I was experiencing over whether or not to sleep with Phoebe.  I wrote at first: 
My concern now is that if I drag my feet with her any longer, she'll completely shut me out. The shallow part of me would actually like to fuck her before that happens. 
Then I wrote:
Phoebe may also not be quite my cup of tea, but I am really conflicted over whether or not to consent to an intimate date with her in order to keep her interested a while longer.
Phoebe had texted me on Wednesday morning asking if I'd decided on the tentative intimate date we'd discussed for Friday.  I went more than a day thinking about it, but late yesterday afternoon I decided that it was better to sleep with her than not. I figured that, if she was still in the running for whatever reason, it would be better to sleep with her so I can make a more informed decision. My mind was still considering the fact that I had taken the chance and had lunch with Crystal even though I had preconceived notions about moms, and had been very pleasantly surprised.

So I texted Phoebe before I left the office: "Sorry for the late response; I wanted to see how my schedule for Friday was going to shake out.  Looks like there's time to get together!  Let me know what time you'd like for me to come over."  She and I agreed on a time, she gave me the address, the gate code, and her apartment number, and where to park. It was on, and I was excited!

Then, last night while we each lay in our separate beds, at the end a fairly lively and flirtatious text conversation, she wrote, "Can't wait to have fun with you!" "And multiple orgasms," I wrote back, confident that I was going to bring my A-game.

"Slow down there, cowboy," she wrote, "let's not get ahead of ourselves."

"You doubt me?" I asked.

"I do," she replied.  "I've had like four orgasms my whole life so it's not a goal of mine."

Had you been with me, dear readers, you would have heard the high-pitched "Whaaaaat?" that came out of my mouth at that moment.

"Getting sleepy now," she wrote.  "Night."

I put the phone down, mind racing.  How does anyone get through life having only four orgasms? Did she mean through sex alone?  Did she masturbate and have orgasms that way? If so, could we incorporate masturbation into our sexual activities? Thinking about Mel and her highly orgasmic sexuality, I proceeded to have a restless night thinking about how my encounter with Phoebe might go, knowing that the only orgasm in the room would likely be my own.

When I woke up this morning, my mind was made up: I was cancelling the date, and Phoebe was out. Once I dropped my kid off at high school, I composed the text on my way to the office:
"Sorry for the short notice, but I'm canceling our date. While we've had a decent and easy rapport, your admission last night that you are essentially non-orgasmic was, unfortunately, a deal breaker for me. I know that sounds shallow, and maybe it is, but after 8 years in this lifestyle I know exactly what I want. And that is a highly orgasmic partner capable of completely letting go when we have sex. While I'm sure you enjoy having sex, part of my enjoyment involves my partner having orgasms with me. This is hugely disappointing for me because I was truly hoping to get to know you better, but that won't be happening now. You are probably calling me every name in the book right now, which is fine, but I'm just being honest and letting you know where I'm coming from."
She wrote back that she still enjoys sex regardless of not having orgasms, "but whatever. Please don't contact me again."

My relationship with my body has given me decades of pleasure. In my fifties, when most other men are reaching for the medicine to boost their testosterone levels, I'm still very much like a fucking 18-year-old when it comes to getting it up and keeping it up. I have a sexless marriage with a woman who has zero relationship with her body. I struggled with Leah's inability to come when we had sex, and know that I could not have been comfortable long term with Natalie's constant need for a vibrator to achieve orgasm during sex.  Why in the world would I pick a Sugar Baby who isn't anything except deeply in touch with what makes her body feel good and is open enough to experience the total surrender that can only happen during orgasm?

Women reading this post (and maybe some men) might feel a little (or a lot) like I'm being a dick about this. Could be true. I've read articles for years that asserted that non-orgasmic women were no different than their more orgasmic sisters, and were equally able to enjoy the pleasures of sex in all their forms. I accept that and I'd believe any woman who says that she enjoys sex even though she doesn't come.  But this is my sugar journey, and my partners, while also on their own journeys, are along for the ride with me. I know what I want in a partner, I won't settle for less, but at the same time I make no judgment about those who are not a match.  If that makes me a dick in someone's eyes, then I'm a dick.

Meanwhile, I am seeing Lauren today for lunch, and fucking Mel on Monday and MJ on Wednesday. I hope they will have as much fun with me as I know I'm going to have with them.

Thursday, October 20, 2016

It's Becoming Crystal Clear

I had lunch with Crystal yesterday.  In my previous post I noted that she was a single mother of two, late 20s, and very attractive according to her pictures. We met for lunch at a great place for Mediterranean food, and she arrived a few minutes early.  "I'm always early," she said.  "If you're not early, you're late," I shot back.  "I agree!" she smiled.

Crystal was so cute.  About five-six, long brown hair, blue-green eyes, and wearing a black top that revealed a lot of shoulder (my favorite body part!) and sexy jeans.  She came into the restaurant and gave me a hug before sitting down.  I then had a chance to check her out completely, at least from the waist up. She wore black nail polish (a bit of a punk edge to her, perhaps?), and what I considered to be over-sized false eyelashes.  This is something I just don't understand.  Her eyelashes made her eyes look like Barbie's.  Maybe that was the idea, but are a doll's eyes more attractive than your own? Oh well, it wasn't like it was a deal-breaker!

Frequently during our meal I found myself leaning in to catch what Crystal was saying because she was extraordinarily soft-spoken. She acknowledged it when I brought it up. "I like being soft-spoken," she giggled. "Better than being too loud, don't you think?"  "Uh," I said, "yeah, especially at this moment!"

Crystal has an incredibly compelling story, and I share it here because I think most people, especially women, will find it inspiring. She grew up in the desert southwest with two supportive parents.  At a young age, she met and then married a man five years older, son of wealthy and devoutly Christian parents, and a millionaire in his own right.  He'd already been divorced once.  They moved to the Pacific Northwest, where she had a child with him, and was four weeks from delivering their second child when, via text message, he confessed that he'd been having an affair and was leaving her. Though totally devastated, she kept her wits about her, hired a lawyer, and filed for divorce. More important than his money, she told me that all she wanted was sole custody of their children.  As she saw it, she could go after the money later, as the law in the state where they lived and married had very favorable rules for wives/mothers.

While her ex-husband also filed for full custody of the children he'd abandoned and hadn't seen since leaving the marriage, he didn't even bother to show up for the court hearing.  The judge interpreted his absence correctly, and dismissed his petition, awarding her the divorce, sole custody, as well as giving her permission to leave the state without requiring consent from her ex.  She immediately moved to SoCal and found a great job, which she has now.

In addition to working full time managing a high-end medical practice, she got her massage license and does therapeutic massages part time in evenings and weekends. She even has an online business that generates more income. These three streams of income enable her to have her own two-bedroom apartment, pay for her car, and day care for the kids.  She has an in-home nanny for the kids rather than an outside day care, which gives her the freedom to arrive home by dinner time instead of taking an extra half hour to pick them up from day care. When she works outside the house, or goes out with friends, she has a decent network to watch the kids.  She gets no financial help from her ex, but believes that in time, her lawyer will be able to get a settlement from him that will secure her children a college education.

I sat listening to her, simultaneously dumbfounded, touched, and mightily impressed.  Crystal was one strong woman.  I liked her immediately.  When I told her, right off the bat during our lunch, of my concerns about arrangements with moms, she told me this story and ended by saying, "I have enough money to support my kids, but sometimes I like to buy stuff for myself, or save up to go on vacation with them, or even to  Disneyland." "You are hitting all the right notes with me," I replied, adding that if we were to have an arrangement, I'd like her to have a Wish List with an online store like Amazon so I could buy her gifts.

With her busy schedule, however, I asked if she had the time to take a few hours off in the afternoon to be with me.  "Oh, I just need a day's notice and I tell the doctor I'm taking the afternoon off," she said. "He's totally cool."

We finished up our delicious lunch, I paid the bill, and we walked out to the street.  With her office so close, it would be very convenient to get together on off days just to be together.  While she said she wasn't interested in dating anyone formally, she was open to an arrangement like that. She agreed to my financial offer too.  I took her in my arms and kissed her cheek before giving her a tight hug, feeling her nice, soft breasts against my chest.  Yes, they're real too.

This time around, I'm finding the quality of the women I'm meeting to be pretty extraordinary.  From Bella to Phoebe to Chloe, and now to Crystal, the common thread is of intelligence, beauty, and resourcefulness. I might have decided against Bella, but she nevertheless had qualities I greatly admire.  Phoebe may also not be quite my cup of tea, but I am really conflicted over whether or not to consent to an intimate date with her in order to keep her interested a while longer.

Another hard truth I'm looking at: Mel doesn't quite measure up to these women intellectually.  I like her sweet personality, her go-with-the-flow outlook, and her tenderness and responsiveness in bed, but if either Chloe or Crystal match Mel sexually, I'd have to consider seriously making a change. Further, there's MJ next week which is happening for sure.  Physically MJ is at or near the top of all the women I've met. I haven't sat down with her and had a conversation, and I'm not going to before we fuck.  If, however, she shows me the same level of intelligence and/or spirit as the others I've met I'm going to be faced with a serious (though first-world-problem) dilemma!

Glad This Anniversary Is Just Online

Five days ago marked the fourth anniversary of the West Coast Sugar Daddy Journal.  From its inception on October 15, 2012, I have set out to document my adventures, feelings, and reflections as an active Sugar Daddy, which had begun even four years earlier, in March 2008.

For those of you who have read from the beginning, you've learned how I decided to embark on this lifestyle and how I took my first tentative steps. You've read about some amazing high moments, some devastating lows, some wild sexual adventures, and the sexual scare of my life. You've seen me take breaks from the sugar life as well as go on binges.  I have stumbled, danced, and charmed my way through more than fifty different women in the past eight years, and have examined my emotions and bared my soul to you as often as I felt able.  Through it all, I have tried to remain as transparent as any married man, sleeping with fifty different women, can be in an online journal. I hope that you have enjoyed the journey so far.  There will be, I hope, many more adventures to come.

Thank you to all of you who have become fans!

Porter Edwards

Tuesday, October 18, 2016

Sugar Update: Who's In, Who's Out, Who's New

Like I did in April, I am broadening my sugar baby search. In April it was different because I had been happy with Aussie but had a nagging concern about longevity with her and I wanted to be sure I'd made the right choice.  In that previous journey, I fucked one out of the 13 girls -- Gemini -- who I saw back then.

Today things are different because 1) Mel and I wanted to explore a threesome with another woman. I found Rose, and while I had a great time, I find Mel's assurances that she enjoyed herself to be somewhat unconvincing. It just struck me as odd that she would even bring up issues about Rose's inability to climax without a toy; and 2) there are emotions starting to bubble up from Mel for me. While under certain circumstances I'm flattered if she has feelings for me, if they are left unchecked or not discussed then they could insert themselves into our arrangement in any number of undesirable ways.  Jealousy is chief on my mind.  C/Hayden and I always had a totally open relationship and there was never any hint of that going on. Audrey and I actively sought out other partners to join us and that was a huge turn-on for both of us. Even Staci and Aussie were interested in that sort of thing happening, though the arrangements never lasted long enough for that to develop.

It did occur to me that Mel might be feeling somewhat insecure for some reason.  Here we are, barely a month into our arrangement and I'm talking about bringing in other partners.  Perhaps she's wondering if I'm satisfied with her.  Mel's bedroom talents are near the top of my list, all across the board.  Companion-wise, she's sweet, funny, likable, intelligent, ambitious, and well-read. We have lots to talk about.  There really isn't anything with which I'm dissatisfied. Combined with what I'm perceiving as her slight jealousy around Rose, her affection for me could be a problem in the future. The last thing a married Sugar Daddy needs is a clingy mistress, so I'm always hyper-vigilant about stuff like that.  As I see it, better to err on the side of caution and get out sooner than to hang in there only to see things escalate to the point where I can't easily extricate myself.  So, I guess it's on my mind and I'm taking a wait-and-see approach for now.

Still, there are ladies to see and decisions to make. Here is the list of who's in, who's out, and who's new:

Who's In
Mel -- Of course, goes without saying that she's currently my #1.
Chloe -- I met this lovely young woman yesterday for Happy Hour.  She was 30 minutes late, but the bar was in my building so I didn't have to wait -- I just kept working until I knew she was close. When she arrived, she very nearly knocked me out of my chair. In walked this curvy brunette, hair pulled back into a tight bun, wearing black from head to toe.  Her pictures were somewhat more flattering than the actual woman who showed up -- she was slightly heavier than I would have imagined from her pictures -- but with her gorgeous face and smile, I didn't care at all.  She was delicious.  An east coast native, she moved here just a month ago after completing university in London.  She's both Latina and Middle Eastern, and her vibe is intelligently sexy.  She is a month shy of a mid-20s birthday, and she is far more mature than I'd have given her credit for (probably due to her education abroad). Case in point: the bar did not ask her for ID when she ordered a glass of wine. She just carried herself in such a sophisticated way. Her divorced parents are highly successful professionals and live in different countries, so she goes to visit them periodically. Currently she is working in the fashion industry, freelance, and saving up to get her own apartment, but for now she's staying with a friend. She also has some student debt to cover, hence her sugar activity.  Despite her age, Chloe is exactly the kind of girl I like. I'm definitely going to sleep with her.  We have a tentative date for next week.
Caliente (new name MJ) -- We have a date next week, and we're skipping the formalities.  There's just no way I'm not going to fuck her, as she has the best body since C/Hayden and Leah.  In the flesh I'm hoping she's even hotter.  Whether it goes anywhere after that, I don't know, but I'm definitely going to bring up the threesome thing with her.
Mo -- I'm keeping her in for now, although yesterday I saw pics of her on Twitter of her without makeup and in street clothes that were not flattering. I've seen many articles featuring "Porn Stars Without Makeup" and the reality is far less enticing than what we see on camera, so the jury is still out.  No date set yet.
Lauren -- haven't met yet, but, like Chic, she's a Megan Fox lookalike and I'm keeping her in at least until we meet.  We have a tentative first meet for late this week.
Crystal -- the late 20s mom of two.  We are having lunch tomorrow. She works three blocks away from me which will make the first meet very convenient.  As I've written before, she is cute, so I'm keeping an open mind.  A reader suggested to me today that Crystal might not be using the sugar money to survive, but to spend on herself.  That is definitely possible, so I guess I'll ask her that question as I tell her of my concerns.  It may never go beyond the lunch, but we'll see.
Phoebe -- She is borderline out, but I'm keeping her in.  I like her a lot, she's sexy and cute in a bohemian sort of way, but as a blonde she's not as attractive to me as MJ, Chloe, Mel, or Lauren. That's totally a subjective thing, brunettes are my preference.  She's also totally straight, so there'd be no possibility of a threesome with her.  My concern now is that if I drag my feet with her any longer, she'll completely shut me out. The shallow part of me would actually like to fuck her before that happens. (In case you're wondering, that's a joke.  A little.)

Who's Out
Ankh -- just not feeling it from her, so goodbye.
Raquel -- I don't want an arrangement so far from home
Mara -- Also too far from home
Harmony -- She is borderline out, and could be in if we find time to meet. I am so attracted to Asians but my sexual history with them is spotty at best, disastrous at worst.  She seems very reserved, though with a positive vibe.  Definitely not the playful type, and I confess that I like my SBs just a little slutty.

Who's New
Aurora -- Mid-20s brunette, very curvy, college student, bisexual, and already down to play with Mel and me.  I sent Mel pictures.  Her response was generally positive, but she asked an odd question: "You think she sleeps around on her own?" Seems rather strange coming from someone who is in the sugar bowl.  I wouldn't be surprised if Aurora's had many partners.  I have to remind myself that I am Mel's only lover, so this sort of question could be understandable.  But again, feelings could be involved here.  I've sent Mel Aurora's number.  If there hasn't been contact made in the next week, I'll know a great deal.

My next post will be mostly about Crystal.

Monday, October 17, 2016

Plenty of Sugar Fish Take My Bait

As I started looking for potential threesome partners for Mel and me, a few showed up.  One, who I did not name originally but will name CJ, enthusiastically accepted but then disappeared.  Another was Rose, and we had a great time together.  Judging from Mel's reaction afterward, however, I thought that perhaps Mel was less satisfied.  It's pretty complicated, but I don't think Rose and Mel are going to be a good combination.

One very juicy detail that I did not share with you, however, happened after Mel left and before Rose and I had sex again.  Rose had mentioned a close girlfriend that she and her boyfriend play with on a semi-regular basis. She mentioned that this girl was also in a committed relationship but that her man didn't join in.  "They have more of a don't ask, don't tell agreement."  This got me thinking and I took a wild guess. "Her name wouldn't happen to be [CJ's real name], would it?"  "YES!" Rose laughed, very curious to know how I knew CJ.  "Well, I told you about a different girl who had said yes but then started ghosting me, right?  That was her!"  Rose and I shared a laugh about that one.  I said, "I want you to tell CJ that you met me and that you had a blast. Maybe the three of us could get together another time."  It was something we decided to discuss at a later date, but it's a definite possibility.

Today, Rose told me that CJ simply got really busy and let the conversation drift away.  "I get busy all the time," I said, "but ghosting is just not the right way to handle that."  "She was more 'emotionally' busy, you know?" Rose said, and I understood because CJ's fiance seemed like a bit of a needy type. Meanwhile, we agreed to talk in November a threesome with just us.  It would be interesting to have a threesome with two girls who are already very intimate with each other.

Other than Rose and CJ, there are others. A lot of them are exchanging messages with me on the website, but these are the ones who graduated to texting:

  • Chloe -- early 20s, brunette, gorgeous. We have chatted by text for a couple of weeks, and missed a couple of chances to meet up for lunch. Today, however, she's coming in to have a drink with me.  I was hoping she'd meet me for lunch and then spend the afternoon with me, but that'll have to wait till another day.  For now, she's a must-fuck girl.
  • Phoebe -- continuing to reach out, and has sent some hot pics of her slender body. She's bustier than I thought.  Might have to explore that girl.
  • Caliente -- mid-20s Latina, a dancer, with just about the hottest body I've seen in years, all natural. Trying to set up a date for late this week.  She's a must-fuck girl.
  • Lauren -- mid-20s blue-eyed brunette. Wanted to make a date, but her schedule is very unpredictable (like Chic).  Up in the air, but she's also stunning.
  • Ankh -- late 20s strawberry blonde.  Pierced nose, but very cute and sexy.
  • Bella -- late 20s blonde. Met for drinks last week. Let's just say she's prettier in the pictures.  I was not impressed physically.  Plus, she works for a company owned by a neighborhood friend who lives on my street.  Too close to home.
  • Mo -- sounds like a dude, right?  As Trump would say to Hillary, "Wrong!" Mo is an active porn starlet looking for a Sugar Daddy.  You'll recall my sole experience with Kyra back in 2011.  This girl's about the same age, but prettier than Kyra.  In fact, she's built a little like Dale, the girl I was with after Kyra and who endured me for a couple of months before I went back to C/Hayden. I've agreed to a higher rate with her than with anyone ever, but I've seen her work and she'll be worth it. She is also a must-fuck. 
  • Raquel -- early 20s Latina who lives about 50 miles away near my company's HQ.  Very hot, bisexual, and willing to text me any picture I want.  But seems insincere to me for some reason. I told her that I didn't want an arrangement so far from home, but I'd be open to meeting occasionally if she was down.  She said she was.  Haven't texted her in nearly a week.
  • Mara -- Early 20s mixed-race girl. Tall and thin, cute face and body.  Has sent some hot pics so far. Also bi and open to meeting with Mel.  I don't think Mel would be into her so she's back burner for now. Also lives a little far away.
  • Crystal -- late 20s, brunette, with two young kids. Yes, I've made my position on moms clear for years. Essentially, I feel conflicted about moms because I strongly suspect that my financial support would be used to help their kids.  And when these arrangements end -- as they always do -- my child support would end with it. I don't want that guilt on my head. Selfish, I know, but not without some merit for a married SD with kids of his own.  Still Crystal has her own place, has time during the day to meet, and is definitely cute and curvy.  I haven't had sex with a mom other than DW in over 20 years.  Wonder what she'd be like...
  • Harmony -- mid-20s, Asian cutie pie.  A little straight-laced so far, but definitely cute enough to want to meet.  You all know my history with Asian women -- other than Jade, who is half Italian, it's pretty much be a complete failure -- so I'm reluctant to move ahead with this one.

Of these, there are no real good threesome candidates, and that was the reason why I went back to the website in the first place.  I might ask the "must-fuck" girls if they'd be down.

The other alternative is that one of these replaces Mel.  Yikes, I went there!  Mel, who I adore and who is a fantastic partner in so many ways, showed me that she probably has feelings for me.  I've made huge mistakes with women who had feelings for me -- C/Hayden, Jade, and even Leah to some degree.  And I've made huge mistakes when I've had feelings for my Sugar Baby -- C/Hayden, Jade, Leah, and Red.  These bad experiences have taught me to really temper feelings with a high dose of reality.  So I'm going to have to honor my original self-imposed rule to exit any arrangement where I feel there's too high a level of emotional connection.  I hope Mel can contain it, but we'll see.

Friday, October 14, 2016

Threesome Feedback -- Am I in a Relationship?

I got some great feedback to my last post, particularly the last part, after the sex was over.  (Aside: should I write less about the sex, or is that part also something you guys enjoy?).

From one reader:
Reader: Mel is soooooo bothered you stayed with Rose afterwards.
Me: We just talked. She said she was initially a little bothered, but she got over it.  I appreciated her honesty.  If she's lying, though, whatever.  Plenty of fish.
R: But you don't appreciate that you have a good connection with her?
Me: I love the good connection.  But if she's lying (it's possible) then the connection isn't all that good.
R: So then why would you risk that for some other pussy, you know?
Me: Because. I. Can.  LOL
Of course that last line was a joke.  A little.

Here's part of the conversation I had with Mel via text:
Me: Was re-reading our convo from [the other day].  I'm getting the feeling that perhaps you would not like to see Rose again.
Her: What? No, I DO want to see her again!  She's A LOT of fun.
Me: OK, it's just that you seemed disappointed that she needed help to cum, and that she was not as emotionally open to intimacy [as you].
Her: Of course it disappointing but it's no deal breaker, I'm okay with being selfish a bit hahaha.  And that's all I can expect from her.  But the shelf life of a relationship like that wouldn't last long for me.  But let's have fun with her and stop if it becomes not fun.
Me: I also wanted to be sure you were OK with my fucking her after you left.
Her: Well, I wish I could have stayed!  As long as you guys don't play on a day without me, I'm okay with it.
Me: Okay, that wasn't an option for me anyway.  So, do you want an exclusive relationship unless we decide to play with someone together?  You know how much I adore you.
Her: That would be ideal.  And I adore you!  But should you happen to be curious about someone though, it's okay to explore her.  I just ask you to be safe with me.
Me: I'm only looking for potential partners for us.
Her: You're the best!
When she said that she didn't want me to fuck Rose without her there, I got that she was not OK with leaving Rose behind with me, despite the fact that she also said I could go ahead and "explore" with other women.  This was why I told the reader that she was initially a little bothered.  So I think I'm in a relationship with her, and I think perhaps Mel has feelings for me.  I haven't written this before, but Mel told me a few weeks ago that I was the best lover she'd ever had, after only two times together. "You're the total package," she wrote.  Well, except, perhaps, for the fact that I'm married and unavailable for a long-term thing.  But I'll ride this wave so long as it's a good ride.

The second bit of feedback I got was from a reader via a tweet:

I agree with this reader, actually.  I remember last year when I fucked Natalie that she reached for and used a vibrator while I was inside her.  While in the moment I felt that it was an empowering move for her to take charge of her own pleasure, it was the first time I'd encountered something like that, and I briefly considered whether it would be something that inhibited a long-term arrangement with her.  I think, in hindsight, that it probably would have been something that bothered me long-term. For example, Leah, when we first started seeing each other, never reached orgasm when we had sex because she said she'd become dependent on her vibrator for orgasm.  It wasn't until I circled back with her a few months later when she came during sex; she said she'd cut back on her vibrator because she wanted to have orgasms during sex.  In the end, however, it was not Natalie's use of a vibrator that was the reason I decided against an arrangement, but her lack of daytime availability.  

Not every girl can reach orgasm with fingers, or tongues, or cocks.  Sometimes a girl needs help. With Rose being a temporary playmate for Mel and me, her use of a vibrator doesn't bother me at all. And I think Mel can hang with it too so long as we're not engaging long term with Rose.  This is essentially a non-issue.

I so appreciate the feedback!  Please don't hold back!

Thursday, October 13, 2016

Three Definitely Not a Crowd, Part 2

Mel, Rose, and I rolled around, nearly naked, on the big king bed, kissing, sucking, and licking each other. My fingers found their wet pussies and I slid fingers inside them.  Each of them moaned softly as they kissed and fondled each other.  Rose giggled a lot as their tits rubbed against each other.  No doubt that she was more experienced than Mel in the girl/girl arena.  My cock demanded release from my underwear, and Rose quickly pulled them off me before feasting on my dick.

Rose had fantastic skills, slowly going up and down the shaft, then kissing and licking the head.  Her beautiful breasts were in reach and I gently pinched her nipples to get a response.  She took me out of her mouth long enough to say, "Mmm, yeah!"  Mel, kissing and sucking my nipples, slowly made her way down and took over from Rose.  I love, love, love Mel's oral skills. She started licking and sucking my balls, giving Rose another invitation to suck my cock.  But not before I watched Rose eat Mel out from behind.  Every few seconds, Mel had to stop sucking me for a few seconds, but I didn't mind.  "Um, you've got competition, Porter!" she told me before taking me back in her mouth.  "I would hope so," I replied.

After a few minutes of sheer blow job heaven, I sat up, kissed both of them all over, and lay Mel on her back to go down on her.  Rose kissed Mel and sucked her sweet tits while I devoured Mel's clit. "Wow, she really loves what you're doing," Rose said. "He makes my head explode," Mel replied, adding, "pretty soon I won't be able to talk!" I showed my appreciation for Mel's compliments by sticking my fingers inside her and rubbing her G-spot.  While licking her sweet pussy, I motioned for Rose to join me between Mel's legs and take over the oral while I continued to finger her.  A few short moments later, Mel came in a huge wave, going completely stiff and quivering from head to toe. "There's one!" I laughed, throwing Mel a high-five the same way she did to me on our first date.

Then it was my turn to eat out Rose.  She had a pierced clit, just like Aussie, and it clicked on my teeth with every flick of my tongue.  Rose and Mel were kissing furiously so I kicked it up and fingered Rose too. She rocked her hips and spread her legs as wide as she could.  After a few minutes, I moved aside to let Mel have go at Rose.  With Mel's long hair hiding her face, I had no idea what was going on down there, but I was enjoying kneeling beside Rose's face so she could suck me some more.  Not the most comfortable position so I wasn't totally digging it, and I could tell that Mel's oral skills weren't rocking Rose's world because she stopped rocking her hips.  I think Mel could use some more pussy-eating experience.  I think I could probably teach her a few things.

"Who wants to fuck first?" I asked them. Since Mel and I were together as a couple in this threesome, I elected to fuck her first. I looked at Rose as I slid my uncovered dick inside Mel's pussy and said, "Don't worry, just because Mel and I are bareback doesn't mean I won't wear a condom with you. We'll be totally safe."  I grabbed Mel by her ankles and slammed into her like a freight train while Rose rubbed herself.  I helped Rose by fingering her some more.  Grabbing Mel's tight ass, I fucked her as hard as I could and made her come again.  While she lay there, delirious and receiving affectionate strokes and small kisses from Rose, I grabbed a condom and slipped it on, applying a generous amount of lube (it was the only time I did that as I learned that Rose had some unique sensitivity to artificial lubricants -- her preferred substance is coconut oil!).  It was tricky at first, but I told Rose to kiss me to distract her, and my cock slid in, balls deep, in no time at all.

Rose was very vocal when getting fucked.  Lots of loud moaning, and some hot dirty talk, which sounded way more convincing than KC, whose dirty talk sounded far more forced.  I had her legs way up to her shoulders and I got very deep inside her.  Every so often I'd slow down and pull nearly all the way out, then slip slowly back in, which elicited an "Oh my GOD!" each time.

I knew Rose hadn't had an orgasm, but I wasn't making a big deal out of it because, for all I knew, this would be a one-time thing anyway.  So after five or so minutes, Mel wanted more, so I pulled off the condom and entered her from behind  while she went down again on Rose.  So hot to see that from that perspective.  Mel came yet again, so I pulled out and let Rose suck me some more before I put on another condom asked her to ride me.  For good measure, I had Mel straddle my face and ride my tongue.  I couldn't see anything but Mel's pussy, but I sure heard them kissing and laughing. Laughing? I thought. I'd soon change that.  I grabbed Rose's round butt and started fucking her furiously.   Mel had to get out of the way as I pulled Rose down to me, so we could slam into each other with all we had.

I still hadn't come, and knew that the condom would probably prevent it, so I peeled off the condom again and had Mel get on top of me.  This would do the trick, I thought.  Like I did with Rose, I put my arms around Mel and we got into a furious rhythm. She came again, and soon after that I felt the familiar rush of orgasm coming over me.  I pulled out and started stroking my dick. Rose didn't miss a beat and took me in her mouth when I came, and she swallowed all of what I gave her!

With all three of us smiling and spent, we giggled and cleaned up a little.  Rose went to the bathroom and rinsed off. Apparently she had some skin sensitivities and both latex and lubricant were mildly irritating to her, but she never made it a problem.

We talked about half an hour or so, sharing life stories and different experiences with the swinging lifestyle. Rose had had a rather interesting journey.  Growing up in the San Francisco area, in a very wealthy family, she discovered in high school that she liked girls.  She went so far as to become engaged to a woman, but that didn't work out.  She then met and married a man who she said felt more like a friend than a life-partner.  She divorced him after about a year and a half.  Soon after that she met her current boyfriend.  With their completely open relationship (he is also bi) they have had some pretty wild experiences, and she said that she could never conceived of being in a monogamous relationship.  I found it so refreshing that she had such a healthy attitude about sexuality and commitment.  As I've written before I will never again enter into a long-term relationship if it means I have to be monogamous with my partner. Rose agreed that people should be free to have sex with whomever they wish, and that she could never see herself giving up on sex with women, no matter how much she loved her boyfriend.  I thought to myself, this is someone I'd like to see again, in a threesome or with her boyfriend doing a swap. I asked Mel if she were down for something like that, and she said, "Of course!"  Rose agreed as well, and she agreed to discuss it with him later.

Mel said she had to leave because she a longer drive home than usual.  I asked Rose to stay and asked Mel if she was alright with me fucking Rose some more.  Both were totally fine with it.  Mel dressed and left a few minutes later, kissing both of us on the way out.

Rose and I talked a little more after Mel left, and I said, "You haven't come yet, have you? How can we fix that?"  Rose giggled again and said, "I usually can't come without my vibrator," which she'd brought along.  "You can fuck me from behind while I use it."  She reached into her purse and pulled out a small vibrator that looked like a fat lipstick container.  Coming back to the bed, she spread her legs and wet her pussy with her saliva, then pushed a button on one end of the toy and put in on her clit, closing her eyes.  I totally enjoyed the watching, but knew I'd need a little help to get hard again. Rose obliged by giving me another fantastic blow job.  I couldn't help thinking that she'd be a pretty fucking great Sugar Baby partner, though I wondered if I'd eventually tire of the vibrator requirement. It didn't bother me all that much with Natalie last year.  At least not at the time, but I could see how it might be a barrier.  Still it was worth trying again.

Now that I was rock hard again, I slipped on a third condom, without lube, and entered her from behind. She put the toy right on her clit again and I took her waist and fucked her hard.  She buried her face into the mattress to muffle her loud moaning, but I wanted to hear all of it, so I grabbed her hair and pulled her up.  "Let me hear you!" I urged her.  "Come on that dick, baby!"  It didn't take very long.  "Ohhhhh, OHHHHHH, I'M COMIIIIIIINNNNNG!  NOOOOOOOOWWWW!" She simply rocked her body all over the place.  I had to hold her there to keep her from falling off the bed. She went flat on the bed and I stayed inside her.  The condom was doing its best to kill my erection, so I pulled out and removed it again.  I figured I wasn't going to come again.

I turned Rose over and got between her legs to kiss her some more. After a little while, we started rubbing against each other.  I spread her legs wide and rubbed the shaft of my hardening cock against her lips. We both added some spit to make it a little slippery, which resulted in my slipping right inside her without a condom.  "Oh, God," she said, opening her legs wide.  I made no effort to pull out as she was not protesting at all. About thirty seconds later, however, I did pull out because I realized I was going to come. I left a few tiny drops on her stomach.

Rose got up to rinse off again.  I took that opportunity to slip the envelope in her purse, but her purse was so tiny it didn't fit, so I just left it on top.  When she came out, I told her that I would really like Mel and I to get together with her and her boyfriend at a later date. She said she thought it would easily work. "Mel is so cute and special!" she said. "I loved her body and how responsive she was."

With the sex over, it was time to get home.  The hour had grown late.  Rose and I kissed passionately, and she giggled yet again.  "I had a great time," she said, "we should do this again."  I agreed.

After showering I got in the car and called Mel, who had not yet arrived at home.  I told her what had happened after she'd left.  Mel thought Rose was adorable and sweet, and great in bed. She definitely wanted to see her again.  "What about a couple swap with her boyfriend?" I asked.  "I'd have to see his face first," Mel replied, "I really like good looking men."  I told her I'd have Rose text me a couple of pictures and we'd talk again later.

That night, Rose sent me two pictures: one of her boyfriend, Drew, who had a shaved head and a neatly trimmed beard, with a nice smile and blue eyes. "Beautiful man," she wrote, "sweet guy, great body." The second picture, which I hadn't expected, was of her on her back, holding his hard dick right after he'd unloaded on her chest.

I shared both pictures with Mel the next day.  She surprised me a little by saying that she wanted to hook up with Rose again before doing a couple swap.  "Totally," I replied, "or someone else?"

"If you can find someone else as hot and playful! Even better if there's someone out there who can cum without a vibrator too!"

I founds this last statement very puzzling. "You count that as a negative?" I asked.  I crossed my fingers that Mel did not think I was being argumentative.

"No, who doesn't love a giver?" she replied. "In the big picture of things, I prefer a balance of give and take and she's just way more of a giver, which isn't a bad thing!  But I think there's a slight emotional barrier that prevents her from being able to cum from human touch, and that's okay. It would just be so nice if she allowed us to really return the favor."

"You saw how much she enjoyed getting fucked," I wrote, even more puzzled. "I guess she likes intercourse better than oral anyway, which is not all that different from a lot of women I've been with."

"But did she cum?"

"She did when I was alone with her, using the vibrator while I was inside her. She literally exploded."

"Yes, but I want to see her cum without the vibe."

What was this all about?  I was thinking that Mel was less into Rose than she'd let on.

"Again," I wrote, "I'm wondering why you think that's a negative that she doesn't climax without a vibrator.  Have you noticed how hard it is for me to climax when I'm wearing a condom?"

"Not really a negative," she countered, "I just see her as closed to emotional intimacy."

This convinced me that we'd perhaps see Rose once more and that was it.  "Keep in mind that she is in a committed relationship with another man.  I don't count it as a negative that she is less emotionally available than a completely single woman."

"Honestly I get the feeling it doesn't even have to do with that, and that's OK, it's really not a negative."  But it was.

"I think it's awesome that you and I have an emotional connection, and that's enough for me," I wrote. Plus, there are at least one or two others who would be just as much fun, I think, to get together with."

"Bring on the pussy buffet!"  Wow, I thought, she is done with Rose.

I hadn't considered that as a possibility.  I also wondered if it bothered her that I stayed with Rose alone after she'd left.  More to be revealed there.

Tuesday, October 11, 2016

Three Definitely Not a Crowd, Part 1

Come and knock on our door/We've been waiting for you/Where the kisses are hers and hers and his/Three's company too.

Yes I know that I've totally dated myself with that old lyric from the theme of the 1970s sitcom, Three's Company.  In any event, it is a gentle nod to the wild fucking time I had with Mel and Rose earlier this week.  After Rose left the hotel room, I had to admit to myself that the experience was better by far than my threesome with C/Hayden and The Dancer, which happened nearly five years ago.  Further, although the jury is still out, I don't think this particular threesome will have the same kind of fallout that the last one did.  See here, here, and here for details on that one.

The arrangements for this threesome differed primarily in that I arranged it.  In that way, I assured that stuff would happen at the pace I wanted it to happen.  With C/Hayden, I let her arrange everything because 1) The Dancer was her friend, and 2) I didn't want to seem pushy.  With Mel, however, she is actually bisexual, and was totally into the idea, and was totally glad to let me set it up.

So, I went to the Sugar Daddy website and scoured the profiles looking for young women who noted that they were interested in both men and women. I was completely honest with those who I thought might fit the bill, sending them messages that read something like this: "My SB and I have been together about a month, and we're looking for willing partners to join us in a threesome.  I can't promise that this would be a regular thing, so you're free to pursue sugar activities as you wish.  But we are both lots of fun and it could be something we'd do more than once or twice. If you're game, let us know."

You'll remember from my last post that Rose enthusiastically jumped at the chance to meet up with Mel and me.  I booked a room at the same hotel where I'd been with Sam and Chic.  I made sure to book a room with a jetted tub.

When Mel and I had scheduled our date two weeks ago, it hadn't dawned on me that it was a federal holiday. My company would be closed, my offices closed, etc.  Normally, that's a three-day weekend where my family and I could have some quality time together.  But DW did not have the day off, and the kids had school, so I was on my own.  But how was I going to be able to navigate my day when I didn't have to be at the office?  Easy.  I went to work anyway!

I dressed for work, packed my lunch, and I drove my older kid to school, which was about 15 minutes away from my office. I got to the empty suite around 8 am, and planned to hang out there just for a couple of hours.  I was completely alone, and played some music and did some reading about the upcoming presidential election.  Around 10:30 am, I packed up my stuff and took it down to my car.  From there I walked to the bank where I'd withdraw the funds from my checking account and deposit them into two envelopes for Mel and Rose.  But duh! The banks were closed on this federal holiday!  I had to withdraw the funds from two different accounts via the ATM -- and one of them was a joint account.  I then transferred money from my account into the joint account to cover my tracks as best I could.  DW would probably see the transaction, so I resolved to make that statement a paperless one from now on.

With my money, stuffed into cards, I drove home. DW was actually at an offsite conference until late in the afternoon, so I had until about 2:30 to take care of business before my younger kid got home.  I got home, took a quick shower, had lunch, and hung out.  Unfortunately I was totally keyed up and couldn't relax.  I was nervous about what was going to happen.  I really hoped Mel and Rose would get along.

At around 2:30 I headed to the market to pick up a bottle of champagne (Rose's request), some cups, a few bottles of water, and some gum to hide my alcohol and pussy breath.  I got to the hotel around 3 pm and parked in their parking garage.  As I walked to the elevator that would take me to the lobby, I noticed a whole bunch of jetted tubs sitting in a corner of the garage, along with a large jacuzzi.  Oh no, I thought, they're taking out the tubs.  I got up to the lobby and noticed that the pool was also empty and being worked on.  As I checked in, I learned from the clerk that the hotel was actually getting rid of the tubs altogether because they leaked too often.  Well, I thought, I paid for a room with a jetted tub, which was about $50 more than a standard rate.  Hopefully my room's tub would be working well.

Turns out I got the same room as I had with Chic, which had a tub whose jets weren't working. Oh well, I thought, I guess we wouldn't be using it and I'm out about fifty bucks.  As I contemplated that waste of money, I arranged the room, blasted the A/C, got ice for the champagne, took out some condoms and lube, and then lay down to relax.  I didn't expect Mel till about 4 and Rose just after that.

Mel showed up first, looking gorgeous in a short black dress with cute wedge heels.  She wore no bra and I wonder if she had no underwear on either.  We sat on the bed and kissed for a minute, talking about her recent trip with her mother and younger sister.  She said she enjoyed it but had no relax time at all.  She wanted to go back with people her own age next time.

Around that time, Rose showed up, wearing a spaghetti strap top, a denim skirt, and flat heels.  She looked exactly as her pictures showed, except perhaps just a little heavier.  No matter, she looked really cute.  And she had a great vibe as well, just going with the flow, giggling a lot, and being very sweet both to Mel and me.  She let us know that she was in a significant relationship, but that it was totally open and he even knew she was with us.  I really liked knowing that there were people out there who could have an open relationship and be completely in love with each other.

We were all sitting on the bed chatting for about 15 minutes before Mel excused herself to go to the bathroom.  I took that as an opportunity to start making out with Rose. "Let's surprise her and be totally going at it when she comes out."  I was in between Rose's legs, fully clothed, when Mel came out.  We laughed and she said, "Don't let me stop you!"  I kissed Rose a few more times before she then got up to use the bathroom.  When the door closed, I said to Mel, "Let's get naked and break the ice."  She took off her dress, revealing bright blue panties.  We were entwined and nearly naked, when Rose emerged, giggling some more.  "You have too much clothing on," said Mel, which prompted Rose to take off her top and strip down to her skimpy black underwear.

With us all nearly naked, the fun began!

-- to be continued --

Friday, October 7, 2016

An Interesting Sugar Week!

In my last post nearly 10 days ago, I noted that Mel and I wanted our next date to involve another woman.  I returned to the Sugar Dating website to look.  I figured that among the 1,900 or so women with profiles on the site, there'd be a decent number of them who were down to have an encounter with Mel and me.

I figured right!  I mentioned in my last post that I'd already traded messages with two of them and one had enthusiastically accepted. Unfortunately, that one mysteriously disappeared the second Mel reached out to her.  What I did know of this girl was that she was engaged to someone, but their sex life was very problematic.  He was an abuse victim and she wanted more than he was capable of giving her, so they had an agreement for her to seek fulfillment outside the relationship.  If I had to guess, I'd say that she probably just got cold feet and changed her mind.

But as I have always said, there are plenty of fish out there! In fact, there were at least half a dozen others who were down for a threesome.  One, whom I'll call Rose, is an early-30s yoga instructor who is very experienced with swinging. She texted over a bunch of pictures showing her having sex with other women.  I got curious and asked if she were a porn star, but she said no, she just liked fucking both men and women.  With Mel out of town with her relatives, I wasn't sure if she'd have enough time to connect with Rose, but they managed to make contact yesterday, and now we're totally on.  She lives nearby, so I booked a room at the hotel where I last had sex with Sam and first had sex with Chic.  In about three days, I will fuck both of these hot women, who will also fuck each other.  I'm seriously hoping that this eclipses my threesome with C/Hayden and The Dancer in terms of hotness, because if the last threesome was my last one, it will be forever tainted with the STI Scare of 2012.

Meanwhile, there are also a few, including Phoebe from earlier this year, who want to get together with me. I'm probably not going to get together with any of them, particularly if things with Rose work out and we can make this a semi-regular kind of thing.  It's something the three of us are definitely going to talk about. But with the young ladies who have impressed me thus far -- Phoebe, Rose, Sky (early 30s, east coast, redhead), and Chloe (early 20s, brunette, gorgeous) -- I'm keeping all their numbers because this Sugar stuff is too unpredictable.

Meanwhile, my third post for Let's Talk Sugar is with my editor and should be posted next week. Will link to it when it's up.