Monday, June 29, 2015

Staci Date #2, and New Job Woes

Late last week I had my second date with Staci.  I had cleared my entire afternoon schedule to be with her, but things didn't quite work out that way and I only had about two hours with her. Turned out that it was more than enough time to have as much as as we could.

As you might know, I take meds for my prostate that prevent me from having ejaculations.  The pills have are only good for about 24 hours, though -- if I miss a day, I can ejaculate again, but there will be some negative impact on my prostate.  When we were last together, Staci got to see first hand how the pills affect me, and she told me later than she wanted me to be off the meds so she could experience having me cum inside her.  Given that Staci uses The Ring for birth control, and given that both of us were tested clean, I had no issue with that!

I arrived at her apartment about 15 minutes early and sent a text to ask if I could come up.  She told me she was waiting for me!  She greeted me at the door in a black cropped top and black thong, contrasting nicely against her tanned and toned skin.  Music played from her Pandora account through her TV.  She apologized that she had to handle some personal business before we began.  I sat next to her on the couch while she finished up a phone call with a relative who needed a ride to the airport and then ordered an Uber ride.  While on the phone with the Uber driver, I pulled down on the neckline of her top and exposed one of her breasts and started sucking on her nipple, which got hard in my mouth.  I massaged both of them and worked my hands between her thighs.  She opened her legs, but the call ended before I could take off her panties and go down on her.

Once her business was finished, I grabbed her by the wrist and pulled her toward the bedroom.  My dick was pushing at my pants and begged to be released.  We got naked almost immediately, and I started going down on her.  Even though she said she never climaxed through oral sex, she twitched and moaned a lot while I was down on her.  I stuck my finger inside her, but took it out again when I felt The Ring.  No sense in messing with the birth control, right?

She gave me a sloppy, wet, gagging blow job that I didn't want to end.  But I wanted to fuck her more than have her suck my dick, so I sat up, rolled her onto her back and entered her missionary position. I came very quickly, perhaps after just three or four minutes, but I unloaded a ton inside her.  She got up and cleaned up, and joined me on the bed, where we chatted for a long time.  One thing we sort of avoided -- for the most part -- was talking about relationships.  I felt very glad that the conversation could involve politics, religion, work, etc.

On that topic, I had to have a serious conversation with Staci about continuing our relationship.  I have decided to change jobs again (unfortunately), and our ability to continue depended on where I was going to be headquartered.  Currently, my job takes me all over town on client business, but the job I'm going for now is much more of an in-house gig.  I'll be commuting to the office and staying there all day, then commuting home. When I began this process with CC back in 2008, I was able to get out during the day for client meetings.  That never changed in all the seven years since.  But this new job is far more internet based and phone-based, and there will be very little opportunity for me to leave the office for client calls.  Further, the commute is going to be anywhere from 50 to 75 miles round trip, so getting out in the field is not something I desire on top of that.  If I do get this job -- and it's likely I will -- I'll have a choice between two offices.  One office will allow me to stop by her place on the way home, but the other won't.  If they put me in the office with the longer commute, then I'll have to end the arrangement and find someone who lives closer to my office or at least close enough on my route.  Staci was not happy to hear this, but because of other factors, I'm not going to be making any decision for at least another 30 days, so there will be a few more opportunities to get together.

We fucked again, this time much longer and more intense.  While she was sucking my dick, her doorbell rang a couple of times and she got up to see who it was.  She was able to get whoever it was to "leave it at the door."  We laughed about it because she had a tendency to be a little loud when we played.  In fact, she had orgasm after orgasm, and she was shouting at the top of her lungs "I'm coming again!"  No way her neighbors couldn't hear her, particularly since her bedroom window was open.  I didn't care; no one was going to see me when I left.  She came hard!  At one point her eyes rolled back in her head.  When I came, she asked me to pull out and cum on her stomach.  Even though this was my second orgasm within a couple of hours, I still had a lot left.  She smiled and looked at all the jizz on her belly before getting up to clean off.

Then my phone started ringing off the hook with client calls, so I had to take them.  We spent our last half hour together with both of us on the phone, not talking to each other.  After I showered ofI, we made our next date and then I hit the road for my next appointment.

Staci is one of the finest looking girls I've seen in a long time, her rock hard abs and firm ass making me instantly hard.  Not to mention that she's extremely skilled in bed and just wants to do more with me.  If I get this new job, I will be very sorry to let her go, but this guy's got to have priorities!

Wednesday, June 24, 2015

Great Lunch With Jade

I hadn't seen Jade in more than a year and a half.  Up until recently, it had been nearly a year since we'd exchanged words (when I apologized for being harsh with her when I broke it off).  I honestly can't remember which of us reached out first, but once we started texting each other, we agree wholeheartedly to meet for lunch and see where things were.

She chose a delicious vegan place near where she worked, and we had an inside table where we could speak frankly without a lot of prying eyes and eavesdropping ears.  I didn't know what to expect, but one always has to be as careful and discreet as possible when living in the sugar bowl.

We got caught up: she asked me about my kids and wife, and my job.  She told me about her new freedom.  Last year, she had a great success and it paid off handsomely.  "I just took off after that!" she laughed, heading to Europe and the East Coast for a few months.  She had some dark days just before her success, confessing that she'd been suicidal and that she'd actually written "a few notes" to send to people who mattered to her.  But someone she cared about, a good friend, talked her off the ledge and basically saved her life.  She returned from her trip, and decided to ditch the career path she'd been on despite the success she'd had (too high a price), and try her hand at something else.  She parlayed her extraordinary networking skills and has started repping some talented people.  "I have a bank account with actual money in it, a nice place to live, and a car that runs," she said, adding, "Now I'm totally free to do what I want."  On the relationship front -- a discussion that did not last very long -- she said that she and the guy she was with came to an understanding.  "Do I know he's fucking other women?" she said. "Probably."  "Does he know I fuck other men? Of course!  He's my number-one boyfriend and I'm his number-one girlfriend, but that's as far as it goes."

After lunch, she moved in close. "So tell me about your girls."  I shared my Audrey and Leah stories, with a little editing so that I didn't tarnish my image too much.  I did admit being indiscreet with a photo of Audrey, but told her a different story about how I did that.  I told her about how I discovered Leah's relationship to a high school friend of mine, but I didn't relate the follow up date I had with her after ending things.  She asked if I were seeing anyone special, and I said no.  Indeed, that was pretty much true.  Staci doesn't earn the title "special" after only one date.  Not even C got that honor.  Leah did, however.  Stupid me.

"I think we should be banging each other again," Jade asserted.  "I wish we could leave her right now and just... hahahahahaha!"  She said that, being in her early thirties, she'd hit her sexual peak and wanted to fuck "all the fucking time," accenting her words by pounding on the table.  She said she wanted another arrangement type relationship.  "I remember everything about your penis, Porter.  I told my girlfriends about it!"  "I see," I said, not really sure what to say.  I'd resolved not to go there and say yes to such an offer, tempting though it may have been.  I flirted with it, though: "Let me pay the check...can we go to your place?" "Ah, I can't," she said, "my girlfriend is staying there a couple of days, and I gotta get back to work.  Besides, I'm on my period, so no go."  But she really wants this.  I didn't give her an answer, but we resolved to discuss it.

After I paid the check, I walked her outside and we kissed on the lips (no tongue) before parting ways.

I feel completely torn.  Readers will know the tortured history of my time with Jade, but I'll briefly synopsize it here.  The electric beginning, the totally hot sex, going bareback very early, her emotional vulnerability and neediness, her affectionate personality -- all paired with a neurotic tendency to stretch the truth, deny reality, and fabricate stories out of thin air.  She explained during lunch that she'd gone through a very dark time, but in truth, I did too.  I thought that my marriage was on its way to being over, and I'd gotten back together with Jade because I was drawn in by her warmth, her artistry, her passion in and out of bed. On her birthday I gave her a card and told her I loved her, and she returned the sentiment.  We loved each other, and for the first time I considered the possibility of a real relationship with someone other than DW.  And then shit started going haywire: she lived with a guy, she slept with him, then he hit her, and she didn't leave him.  In fact, she went on vacation with him and slept with him again.  She went so far as to remind me that we'd met on a sugar website.  That really hurt, considering I'd opened my heart.  I started protecting myself and backing away from the relationship, and then she lied (or at least I thought she lied -- we haven't really talked about it) about being in the hospital when her Facebook page revealed something else.  I felt that I needed to put as much distance between us as I could, so I sent her a vicious text to make sure she didn't ever contact me again.

I saw the mistake I'd made and I apologized months later, but I never even thought once that we'd be sitting across from each other again, let alone contemplating a renewed arrangement.  What I believe about myself now is that, despite all she'd done, despite how hurt I felt, my feelings for her haven't entirely gone away.  I was lucky enough, after Jade, to have a good stretch of time with Sugar Babies for whom I felt no affection.  Audrey was great, and I sure liked her a lot, but it came nowhere near anything I'd felt either for C or Jade.  And Leah?  Well, I got sucked in there, but I think a lot of that grew out of my own hope that she turned out to be a combo of C and Jade.  I think that, were I to get involved with Jade again, I wouldn't be able to keep my feelings out of it.  And I think that's a problem, at least right now.  I am happily married and feeling secure there, even in the absence of all things sexual between us.  Bringing Jade into my life now might upset all that, even if what she wants is just a sexual relationship.  Plus, I do like Staci and feel that sex with her would be better, more varied, and less emotionally charged.

I guess I've talked myself out of an arrangement with Jade, at least for now.  But I'll still talk to her.

Saturday, June 20, 2015

If I Didn't Have Bad Luck...

Yesterday was to have been my second date with Staci.  At 5:15 a.m., however, she texted me to tell me that a good friend had a medical emergency and had asked Staci to take her to the hospital because the friend's husband was out of town.

We have rescheduled for this coming Thursday, although my work week is absolutely insane and I'm not sure I won't have to cancel again.

Jade and I are scheduled to meet for lunch Monday afternoon.  I'll update on what happens there.

A reader posted a question on my previous post, asking me if I'd ever gotten an STD from having sex with all these different women.  My answer to her was a brief no, and I'd like to elaborate further here.

About two and a half weeks after my very memorable threesome with C and The Dancer, I got a text from C asking if I'd gotten recently tested, because The Dancer had just informed her that she had tested positive for gonorrhea.  The Dancer had contracted it from her boyfriend, who had contracted it from a man he had slept with.  Tangled web of STD crap, right?  I went and got tested immediately, since I'd recently had sex with DW and was terrified that I might have infected her.  The first lab I went to took blood and urine, but tested me negative for any STD, so I felt relieved.  But C's tests came back positive for gonorrhea in her throat, and she urged me to get tested again in a more thorough way.  I went to another STD clinic which did far more thorough tests, and I was diagnosed with Non-gonococcal Urethritis (NGU), which the doctor said was probably transmitted through oral sex.  I had been completely without symptoms so this came as a complete shock.  But, because of the fact that both C and the Dancer had gone down on me, I was convinced that I had gotten NGU from this encounter.  I took the medications and got more for DW, and $600 later, I battened down the hatches and prepared for DW to leave me, even though I'd been denying having extramarital sex all along.  A few weeks after being tested again by my primary doctor, I came up negative, and felt all was clear.  My marriage, thankfully, survived.

The following year while dating Jade, however, I was feeling some itching and other symptoms and went to my primary care doctor (a different doctor as I had switched in the meantime), and he sent me to a urologist.  I told the urologist my symptoms, and he ran some tests.  I also told him about the previous year's problems.  He said, emphatically, that if I'd had NGU I would have, three weeks after contact, had very likely presented with severe and quite painful symptoms.  He said that, more probably, I had a prostate infection, which, according to many websites I've seen, is actually a non-sexual way to contract NGU.  The urologist suggested that the doctor at the STD clinic had probably misdiagnosed me because he wasn't a board-certified urologist.  Feeling a little more reassured about how careful I'd always been, I took another course of antibiotics for this current infection and the infection went away in a week or so.

Two years later (this year), however, the symptoms returned yet again, this time while I'd been seeing Audrey.  While this time the symptoms were less severe than the previous time, it really started to bother me, and I went to another urologist.  This doctor told me that this particular kind of prostate infection can be chronic in nature unless a much more aggressive course of antibiotics can be administered.  So, instead of a six- or ten-day course, this doctor prescribed me a 30-day course of a powerful antibiotic, and another medication to ease the swelling in my prostate.  I've been symptom-free for months.

So, that's the long-winded answer to my reader's question.  I still get tested for STDs regularly, and so far, no positives.

I try not to dwell on the possibility of bad luck or good luck.  I feel like I do what I need to do (even though I take risks having unprotected sex) to protect myself and my family.  As I'm very careful about the women I choose for these arrangements, I am highly confident that the women are not having unprotected and indiscriminate sex with multiple partners.

Thursday, June 18, 2015

Lunch Postponed

In a not unusual move, Jade postponed lunch today, saying she was not feeling well and hadn't slept in three days.  This text came hours after we'd confirmed our meeting.  That she didn't tell me she wasn't feeling well at the outset this morning is what I'm deeming as "not unusual."

She later invited me for tomorrow, but tomorrow I'm fucking Staci for the first time in five weeks.  I just can't see pushing a sure thing like that aside to have lunch with a woman who has a boyfriend.

Wednesday, June 17, 2015

Lunch With Jade, Preview

This Sugar Daddy has drawn a clear line in the sand when it comes to entering arrangements with women who have significant relationships.  Jade and I have been texting lately, and she has returned to town from a long trip and wants to meet for lunch.  We arranged a meet at a very small, out of the way sushi joint near where she is working for later this week.  With all luck, the place will be completely deserted and we'll be alone to chat.

We have not seen each other since November 2013, and we haven't communicated much since December 2013, until very recently.  There will, I imagine, be much to talk about during an hour or so other than "do we want to try this again".  Jade and I lasted from February to June 2013, then reconnected in September, and I ended it in January after getting fed up with her lying.  My incendiary goodbye text to her brought up a lot of feelings about giving my power away to women. And I feel very strongly that I learned a great lesson about that and have not given my power away in any fashion since then: not with DW, Audrey, not with Leah, and so far not with Staci or College. And I'm not going there again with Jade.

If she brings up the subject of reestablishing an arrangement, I'm going to deflect it for now with something like this. "A lot has happened since we were last together.  I've grown a lot, and you have too.  I think this is a good first step in becoming re-acquainted, and there will be more chances to do that, I hope.  Let's take it slow."  I think she'll go for that.  For me, if there's a man in her life then I'm not touching her at all, so if she doesn't go for that, I'm out fifty bucks and a couple of work hours. No big whoop.

More later...

Monday, June 15, 2015

I'm a College Dropout

College wowed me with her beauty and her intelligence.  At the end of the day, however, I could not see myself contributing to her, plus paying for both a hotel AND a driver, in order to spend time with her, especially when I had someone who had her own place closer to me and who wasn't going to be leaving town in six weeks.  If I looked at it objectively, had College been able to get around on her own, I could have booked hotels closer to me and had her come out to me; that might have convinced me not to drop her.  But drop her I did.

She was gracious about it, though disappointed we weren't going to be seeing each other again.  Staci is close and I can see her anytime I want.

Ironically, however, the "story" I'd told her that I would be too busy during this month and part of next (which was to give me time to play with College until she left for her vacation and then back to school) is coming true for me.  My work has me extremely busy and very unsure of my schedule.  So even though I'll stick with Staci, I'm not sure how much time I'll have!  First World Problems, am I right?

On the home front, DW and I are headed out of town to attend a wedding in a couple of weeks.  She suggested that we get a hotel room at the hotel where the wedding will be held so that we don't have to drive home that night.  The kids will be with a relative that night.  It'll be fun to hang with DW, though I'm under no illusions that the evening/weekend will involve anything beyond a hand-job. My DW has made it clear that penetrative sex "doesn't feel good, it hurts, and I don't like it."  Any suggestions I make to apply extra lube are usually met with eye-rolling and her involving herself in a distracting activity, hardly the invitation I would like.  But that's who she is, and I'm not going to change her.

Jade is back in town after a long absence, has been texting me and inviting me to lunch.  I'm open to meeting, and I think that lunch will happen this week.  I will not engage in an arrangement with her under any circumstances, at least not now, so long as she has a live-in boyfriend.  I will not compromise on that front, ever again.

Monday, June 8, 2015

A Rare SD Cancellation

Atypically, I'm the one cancelling this week, because I'm too busy with work and my kids have a messed up end of school year schedule.  Gotta be a real Daddy this week!

College hasn't responded to my text yet, and I sent it a few hours ago.

Sports is still staying in touch, although I'm less and less interested in her.

Staci may end up being brought back to the front if College gets upset in any way.

UPDATE:  College is OK with the cancellation, but she may be unavailable next week because she'll be entertaining family coming into town.  Harumph.

Wednesday, June 3, 2015

Sugar Daddy Goes to College

The much anticipated meeting with College happened today.  You'll recall that College had gone on vacation for two weeks once her semester ended.  She returned last week, but with jet lag and my busy schedule, it was not possible to make a date with her until today.

Up front, let me say that as much as I enjoyed practically every minute that I spent with College, I'm not 100% sure that I want to continue.  About her, I have no objections.  At all.  She is a very beautiful, sexy, geeky, and bright girl, and the idea of spending six weeks with her having sex once a week appeals to me on nearly every level.  She'll leave in mid-July for a six week trip to Europe before returning directly to school, and we'll probably stay in touch once she gets back (and occasionally by email while she's gone), but I have one principal objection about the practicality of continuing with her.  Right now, she lives with her mother, about an hour away from me, has no car, and so there is the added logistical twists of hotels and car services to consider.  I know we Sugar Daddies aren't supposed to sweat this small stuff, but right now I want every sugar experience I have to be easy and thought free.  I can't rely on her to book the hotels (she doesn't pay her own bills) so it all falls on me to make it happen.  But, I digress.  Let me get to the juicy stuff.

College agreed to meet me for lunch in a small town midway between us.  I had appointments in that area anyway, so it wasn't that inconvenient for me.  We met at a little tavern/cafe serving Mexican and other gastropub fare.  I got there about ten minutes ahead of her and seated myself right at the front window so I could watch her getting out of the car to walk over.  I was not displeased by what I saw.  College was taller than I'd anticipated, standing 5'6" in flats.  Her hair fell well past her shoulders in dark, highlighted thick curls that looked wild and totally sexy.  My fave look.  She had brown eyes, dark straight eyebrows, and a smallish mouth with perfectly straight teeth.  Beneath her silk print blouse was a black bra and she wore brown shorts that afforded a great view of her long legs.  Lean, but not totally skinny.  In shape, but not totally a hard body.  Curvy, but not overly so.

She sat with her back to the window which made it difficult for me to see her face because of the back lighting.  But I managed to enjoy her company nonetheless.  We ordered a decent lunch and I got out of there with a relatively low bill, and I walked her to my car around the corner.  During lunch I booked a room at a nearby three-star hotel and we drove over there about an hour before the standard check-in time.  Fortunately we got a room and I went up a couple of minutes early to avoid the appearance of going up there together.  I got out the envelope with the $500 allowance and placed it near the counter.  She came in, gave me a kiss, and dropped her purse on a chair in the corner before excusing herself to freshen up.  I took that time to place the envelope directly in her purse, then used the bathroom myself after she came out.

We didn't waste a lot of time chatting before we started kissing.  Here's where things got interesting for me.  Almost immediately, College got really, really aroused.  As we kissed I felt her breathing quicken and saw her pupils dilating a little.  Most telling was the fact that her hips rocked and she was grinding into my thigh.  We kissed A LOT.  I felt a strong urge to keep things really slow... not sure why, but probably because I wanted to see how much greater her intensity could get.  As it turned out, a lot!  I undressed her a piece at a time.  Her body did not disappoint: fantastic breasts, so firm, a great round butt (also really firm), and great muscle tone without being too sinewy.  In other words, a very girly figure without being too soft.  I helped her out of her clothes as I joined her piece by piece until we were both naked.  Going down on her, I had to hold her still a bit because her hips rocked a little too much.   I didn't need to finger her to get her really turned on, because she was dripping wet!  She quietly and very gradually worked up to an intense orgasm that tensed all her abdominal muscles (six pack, by the way) and her thighs clamped themselves around my head!

Afterward it was my turn for oral, but not before she got on top of me and rubbed herself on the shaft of my cock.  Her blow job was brief -- too brief, in fact, and gave me pause -- but she was very skilled, working my balls as well as stroking me the whole time.  Afterward she resumed the grinding.  She teased me by putting the head of my cock almost inside her before she broke the intensity to get a condom and the lube.  I got on top at first and we fucked slowly at first, then harder, before she had another orgasm.  Love her body when she comes, it gets all quivery and tight!

We reversed positions.  College doesn't like being taken from behind, which pleased me greatly since I love all that face to face contact during sex.  She and I organically ratcheted up the intensity till she came again.  Her thick mane of hair cascaded all over my face and shoulders, while I got to sample her nipples again and again and clamp my big hands on her firm tush.  With condoms, I'm always good for a nice long fuck, and we went a long time before I came.

After I cleaned up and returned to the bed, we chatted, talked about sexual histories, and laughed a lot.  She snuggled into my side at one point and we started kissing again.  She climbed on top of me to resume the grinding before getting up to get another condom.  I said, "I know my body, babe; I'm not going to cum again for a long time.  Up to you, but if you don't feel like using the condom, I'm okay with it."  She tossed it aside and climbed back on me.  My cock slipped right inside her and she rocked her hips forward and backward while lifting herself up and down.  I wrote in my last post that I was looking forward to teaching her, but the fact was that College had a great relationship with her body and knows what she likes.  I looked up and her, feeling her body tense up slowly, and said, "Do you think you can make yourself come on my cock?"  "Maybe," she whispered, giving me a great smile and kissing me.  I held her ass in my hands, but I let go and said, "I'll follow you."  She rocked her hips some more, gradually building in intensity, but never in speed, before having an explosive orgasm.

I wasn't anywhere ready, but picked up the pace after she came, and when I thought I was ready, I pulled out.  Too early, however; the momentum was lost and I couldn't come.  She took some lube and stroked me, but it wasn't working.  We took another break and talked some more.  At one point the conversation got very hot, and we'd been in bed for nearly two hours, and I found myself hard again.  I rolled her on her back, lubed us both up, and entered her bareback again.  It took about two minutes before I pulled out and came on her belly.

By the end of our afternoon together, we agreed to meet weekly, with a smaller allowance.  As I drove home, I wondered if the logistics of arranging to meet was worth it.  The jury is still out, but I had a fucking great time.

Meanwhile, Staci was supposed to take a vacation, but she got too busy with work and is remaining in town.  Should I decide that College is a one-off, then I'll go back to Staci right away.