Thursday, March 28, 2013


I have written about Reena before and over the past few weeks I've kept in touch with her.  As I mentioned, she travels back and forth between my town and another place about two hours away.  A week or so ago she was alone one night and we tried to set up a cam date using Skype, but it didn't work out because her wireless was acting up. 

This past week, we talked again about meeting up.  She had the night before gone to a very exclusive party, a party where I'd expected her to at least have sex with one girl or guy, but when I checked in with her the next day, she reported she'd pretty much been a good girl (didn't even drink all that much).  She offered to send me pics of her from the party, and just as I had accepted, she sent me a text that she just learned that her previous SD had had a heart attack and died.  I felt so bad for her, she seemed to take it pretty hard.  I figured that out because the next day she texted me to tell me that her mother was in town and staying with her and that she was glad because she "really need(ed) her now." 

Today we checked in with each other.  Her mom is still with her, along with her daughter (!) that she never mentioned to me that she had.  Well, that explained why she kept going back and forth between these two towns. 

I didn't bring up my rule that I don't date mothers, and I'm not sure I will just yet.  I am very intrigued by her and actually want to meet her before I say no to any relationship with her.  I may even fuck her once or twice, but there will of course be no arrangement.  Kids take all the fun out of these things.  I'm not against supporting a person who has financial needs, but the reality of parenthood makes the financial assistance all the more urgent, it seems to me, and that's a bit of drama I'm just not willing to indulge.

I Felt Her Presence

I returned three days ago from my weekend family getaway.  We stayed in a great upscale hotel across the street from the ocean and the marina.  Lots of nice restaurants there, but of course we stuck with tried and true family-friendly places.  The neighborhood was full of young people, and I just knew that Hayden was somewhere nearby.  I have been regularly visiting her Facebook page (limited as it is by her privacy settings).  She posted a picture of her Christmas tree last December, placed right in front of the window where I could see she had an upper floor view of the city.  It was late in the day (the tree was lit up), so I couldn't make out if she had an ocean view, but I could tell there were no high-rises out her window.  My guess is that her view was either inland or parallel to the coast.

Anyway, on the first day of our trip, I went to her page and saw that she had uploaded pictures of her dog and another dog having a walk.  She captioned the photo that she was down by the marina and the farmer's market with a few friends.  In one picture the dogs were on a park bench, and I recognized the bench as identical to the ones in the marina across the street from our hotel.  Now, I'm sure that these benches continue up the shoreline for some distance, but from that picture I knew that I was very close to her in her neighborhood.  I felt her presence all around the area.  It felt extremely weird and a little scary.  What would I do/say if Sunday morning I was out at the marina with my family and I saw her there, walking her dog with her boyfriend?  Would I just pass on by?  Would I give her a long look?  Would I hurry my family out of there?  Would I figure out some way to strike up a conversation as though she were a stranger?  I just didn't know what I would do.  So the entire time we walked along the marina I kept an eye out, looking for a tall leggy brunette with a little white dog.  Fortunately I never saw anyone who matched that description, but it made for a slightly uncomfortable morning walk.  The third day was spent at a tourist attraction, so I was sure we wouldn't have an unfortunate chance meeting.

The trip resurrected a lot of the old feelings of sadness and regret, the anger, the longing, as well as the sexual high.  I found myself rehashing my final email to her, adding thoughts to it about how disappointed I was about how badly she'd handled our break-up.  In the end, I realized that I was more disappointed in myself for allowing this young girl to consume so much of my attention.  I failed to keep my feelings in check, and I failed to follow my own standards to leave if I felt anything resembling love.  After that I felt better, but this is an off-week with Jade and so I'm feeling a bit lonely.  I do, however, feel a lot closer to DW than I have in weeks past, but I am still not making any sexual advances.  Jade is my only partner for now.

Friday, March 22, 2013

Risky, But Wet!

Jade and I got together for the fourth time, again at the low-budget historical hotel.  The rooms have all been comfortable, and the A/C suitably functional.  I got there at least an hour ahead of the scheduled time, so I had time to shower up.  I decided against getting dressed again, so I climbed into the bed and caught a quick nap, occasionally interrupted by the buzz of my cell phone with a text or call. 

Jade showed up on time, and as I answered the door I opened it wide to reveal that I was totally naked.  Thankfully, I've been exercising like a madman for the past three months and have gotten in great shape, so I felt comfortable doing that.  Smiling broadly, Jade threw her arms around me and kissed me, grabbing my butt for good measure. 

Within a minute or so she was naked and on the bed with me.  We caught up while touching and stroking each other.  Of course, I initiated sex, but she quickly caught on and was soon giving me a delicious BJ.  She's very good at it, but I'm used to the longer suck sessions I got over the past three years from my previous GF.  She came up to kiss me, and then she lay down next to me, turning away from me.  "I wanna do it sideways," she announced.  I love that position, so didn't have to ask me twice.

As has been our habit, I entered her without using a condom.  We didn't even talk about getting one out, and we ended up fucking like that the entire time.  Jade came three times, once while I was on top of her.  She was so ridiculously wet.  I asked her twice, "Are you sure you're OK with this?"  And both times she said she was.  After about 20 minutes or so, I came inside her.  She immediately got up to clean up and clean herself out, but she at no time showed any qualms about having me ejaculate inside her. 

We talked briefly about it, and I guess we're going unprotected from this point forward.  She showed me her pills so I know she's legitimately protected.  We're going to get tested after the Easter holiday so that we're 100% confident that we're both clean.  I fully understand the risks involved, but she gets so fucking wet when I'm inside her, it's such a treat!  So long as we handle it responsibly we should be good.  If either one of us fucks someone else, we have to return to condoms.

Jade's a great girl, and I really like her.  There's likely no way we'll last for too long, considering that I'm feeling lately that there's something better to do, like save up cash for furnishing my house and building up more savings.  On top of that, Reena has been contacting me and wants to meet.  I'm really intrigued, and she has agreed to $500 less the cost of the hotel, as opposed to Jade who wants $500 and the hotel's on me.  She is not bi, but very curious, and she has a "friend" who would more than willing to play with us.  This is a plus over Jade.  But I'm certain that Reena is a condom-only girl.  Not a deal-breaker, but something to consider in the overall decision.

I'm off on vacation the next three days.  Coincidentally, I'll be in the same city where my previous GF lives.  I'm certain we won't run into each other, but in my head I think about what I'd say if I bumped into her and her BF.  I'm really good at improvising on the spot, but I'm sure she'd probably do all she could to end the conversation (or literally run in the other direction).  It makes me smile, knowing that she'd think I was stalking her. 

Monday, March 18, 2013


I had a busy weekend this past weekend, and my week last week was uneventful.  Funny thing, I didn't miss not talking to Jade much.  She was busy and I basically didn't hear from her from Friday until this morning.  She called and we caught up, and she told me she "missed my cock."  Not me, just my cock.  Shades of the last girl.

I know I'm really not that good at gauging how strong things are between me and my girl, so I guess what I write here should be taken with a grain of salt, or at least viewed from that perspective.  I'm wondering if these arrangements are only good for the sexual outlet and nothing more.  I enjoy sex with Jade, and have with nearly every girl I've been with over the years. Maybe I'm just stupid to think that there can be something more to a short-term relationship than sexual recreation.  If that's all there is, why am I spending $1,000 a month just to have sex?  Is sex really worth that much to me?  I could put that money aside and re-furnish half my house in a year, the other half next year, and then travel well every year after that and put significant money toward retirement or to pay off my house faster.

Or am I just too impatient and want the relationship with Jade to hurry up and get super-intimate?  In a way, this feels true, and believe that the last GF has ruined me.  However, given how questionable that last relationship feels now in terms of real intimacy, I'm even more confused.

No action plan for now.  Seeing Jade Wednesday.  Will check in after that.

Monday, March 11, 2013

Adult Dating Websites

Ninety-nine percent of these sites -- from Adult FriendFinder to Just HookUp -- are scams.  Most of the profiles are fake and designed to get you to spend money.  Any profiles you see and send messages to are never answered.  My advice to anyone looking to find a hookup partner stay off those sites.  You're better off going to a bar or a party to meet someone than you are in the online forums.  Funny, but Hayden's BF, who does marketing consulting for adult websites, told her that they're pretty much all bullshit.

Seeking Arrangement and Ashley Madison are legit.  It's how I've met most or all of my mistresses, including Hayden. 

Saturday, March 9, 2013

Getting Pissed

The girl can't stop herself.  Hayden, who has repeatedly told me that she wants nothing more to do with me, reached out to me yet again.  This time I received an email solicitation from her through a website related to her illness, asking me for a donation.  I gave her $50 last fall.  Normally I wouldn't have thought twice about sending another donation -- despite everything, I do support her and care about her -- but this was just too much, and the email just sent me right back into my head.

I sent a very quick reply: "Sigh.  C'mon, angel."  That was it.  But in hindsight, I really want to tear this girl a new one for failing to stay away from me.  I had, after nearly six weeks, finally begun to feel some real, sustained relief from the sadness, the longing, and the pain, of losing her.  But now here she was, asking me again for money.  I am certain that the request was fairly automatic.  She just chose everyone on her Google contact list, as well as anyone else who has previously contributed, and the website sent out the email.  But for someone who wants NO relationship with me, she should be smart enough to a) delete me from her contact list, and b) delete me from her previous contributors list.

I'm pretty angry right now and want to send her a warning that if she ever contacts me again for any reason I'm going to expose our relationship to her BF.  I'd never go through with it (unless she taunted me, of course), but perhaps the warning would be enough to convince her that I'm serious about wanting her to remain out of my life, per HER wishes.

Friday, March 8, 2013

An Unexpected Break -- and Reflections on Middle-Aged Sex

Got a text from Jade yesterday that her mother, of whom we had just spoken on Monday, had suffered a medical catastrophe, and was in the hospital.  Jade said she was leaving for the east coast to be with her mom, but did not elaborate as to how long she'd be there.

Today she let me know that her mom was doing OK but was still in the hospital.  I feel as though she'll probably be back in the next week, but I'm taking this as a temporary break in our relationship.

Meanwhile, DW and I are getting along very well, touching a lot more (non-sexually) and I'm feeling less edgy at home than I have of late.  I'm still not initiating sexual contact, although I'm verbally expressing my desire for her, especially when I see her naked.  I remember a wise man once describing the idea of "building sex equity."  Sex equity is a way to touch your wife non-sexually which creates in her an appetite for more intimate contact.  Lots of hand-holding, hugs, shoulder and neck massages, foot rubs, kisses on the cheek, etc.  The more you do, the idea goes, the more she'll want you for sex.  Not sure how much I subscribe to this idea in all cases, particularly when you have a spouse for whom is barely an afterthought.  Further, as I've always maintained on this blog, this is not about the frequency of sex for me.  It is about the quality of the sex we have.  I'm talking about a connection that really can't be described unless I'm in the moment.

The other night I was listening to an old friend talk about celebrating his 21st wedding anniversary, and how he and his wife had had sex that night.  At one point, he said, in the middle of having sex with his wife (who he took great pains to say he still found gorgeous and sexy) it became clear to him that they were no longer having sex, but "making love."  Usually, he said, sex with his wife was "get up, get in, get off, and get out," but this time, he started to notice a real connection with her, one that transcended the physical and went deep into emotional territory.  I smiled at his enthusiasm and passion in telling the story, but couldn't help but feel a twinge of jealousy.  My friend's wife still liked sex, even though both of them were way past 55 years of age.  DW just doesn't feel that way about sex.  She enjoys being close, and I think the "sex equity" work I've been doing is working with her to deepen our connection without the sex.  But I don't think DW is suddenly going to start giving me oral or talking dirty to me or kissing me passionately for any reason.   It's just not the way she is.  For that kind of sexual/emotional connection, I'll content myself with the extra-marital.

Wednesday, March 6, 2013

The Crucial Third Date

Jade and I met a couple of days ago for the third time.  At the same hotel as last time, and I think that will be our permanent home away from home until she gets her own place.

She was, unfortunately, late again, this time something about her laptop which needed to go back to the Apple Store for repairs.  But, she was all smiles as she came in the door, and I forgot about my being a stickler for punctuality. 

She smelled of cigarettes as I kissed her.  "You're smoking again," I muttered.  "Yeah," she said, "I smoke when I'm stressed.  I just moved and my computer's fucked up."  "I don't like the smell on you, babe," I said earnestly, trying (probably in vain) to get her to stop doing it so close to our dates.  "It's in your hair and hands and on your clothes too."  Since my pleas didn't work, I instead reached over and gave her a couple of wintergreen mints from the tin I had just purchased from the convenience store a few doors down from the hotel.  Took a couple myself.

I kissed her and said "Happy one month, lover.  We met on Feb. 1 and had sex on Feb. 6."  "Oh my god!" she gasped, "you're right!"  She threw her arms around me and we started making out, but I wasn't in a hurry to get naked with her just yet.  First we got caught up about happenings in our lives.  She wanted to know more about shit with DW and me.  I politely changed the subject, saying softly, "I really don't want to talk about my marriage, OK?  Let's just be here, together." 

I went down on her and made her cum.  She sucked me so well, and it felt good to be getting a blow job again, but it didn't last long enough for me.  Perhaps she'll ease into a nice long BJ again.

We had sex without a condom for a few minutes before I pulled out and put one on.  She didn't bring lube, but she felt so wet it didn't seem to matter.  We came together for the first time, which felt great! 

We talked for a long time after that, but I really couldn't wait to have sex with her again.  This time, we didn't use a condom at all.  After a few minutes, though, she complained that her pussy was sore and she had to stop.  What happened next was hot and funny at the same time.  Looking down at my hard cock, I said, "What am I gonna do with this now?"  I started stroking it, and she massaged my balls and started talking dirty to me.  She brought up having sex with a woman, which sent me over the edge.  When I came, my jizz shot straight up and pretty much got on everything, and out of the corner of my eyes (as they were rolling back in my head!) I could see her dashing off the bed while I was in mid-orgasm to avoid the deluge.  Fucking hilarious, but it got me thinking right away: does she have some aversion to jizz?  To see next time, I'm going to let her suck me until I cum and see what she does.  I'm not going to announce it ahead of time either: no, "I'm cumming!"

After I cleaned off, she said that she felt stinging inside.  "That's from the latex, babe," I said.  "When you don't use lube, latex can create little tiny tears in the vaginal wall, and friction from sex just irritates them.  Look it up if you want to see for yourself.  That's why I want to work up to no condoms at all."  We then started talking about exclusivity.  I wasn't sure if the word meant the same to her as it did to me.  I told her that if I was going to be exclusive, I wasn't going to sleep with anyone else (except DW, of course), and that I expected her not to have any other SDs.  Of course, I added, if she met some guy and he asked her out on a date and she wanted to sleep with him, she was free to do so, as long as she told me about it.  The only other thing I expected was that if she got serious with anyone she was dating, that she told me so we could end our relationship.  I wasn't going down the Hayden road again, not ever.  She was completely on the same page as me, but she said something that I found curious: "I don't really like men that much.  Men have not been good to me most of my life."  Well, of course, it made sense since she never met her father and her stepfather was abusive.  When she was 17, she told me, she went on a school trip to Europe for the summer which was supposed to last only about a month, but she stayed in Greece and worked in a pizza joint and lived there for seven months, coming back when she was 18.  She said her mother kicked the shit out of her, so she left for good and hasn't gone back.  She hasn't talked to her mother for over two months. I can't fathom that, as I have a great relationship with my parents, who are still married after nearly 60 years.  It does give me pause to some degree that Jade is appropriate for an exclusive relationship. 

After showering up I didn't stay long, but she did say that she was now interested in having sex with a woman and me.  We'd have to talk about that in the future.

She hung out after I left.  We haven't had a ton of communication since then, mostly because I've been busy, but it's a sure thing that I'm thinking about the future with her (and a friend?).

Friday, March 1, 2013

Jade Is So Beautiful

I am seeing Jade again Monday for our crucial third date.  We seriously can't wait to be together.  Here's our texting each other the other day:

J: By the way... is it me or is our sex fantastic?
Me: It's you that makes our sex fantastic
J: It's US.
She calls me "lover," her "boyfriend," and her "sexpot."  She loves that we flirt over the phone and by text. 

More on Tuesday after we fuck.  Great weekend, everyone!