Stiletto Diaries

So I’m Easy. Is There Really Any Virtue In Being Difficult?

Since we moved here I’ve longed for more excitement, and now it’s finally coming around, in droves no less.

Tomorrow morning I am fetching the lovely Mz. F from Pearson airport.  She will be staying with us for a stretch this summer, which pleases me greatly.

On Thursday evening I have plans with Varick.  We’re going to Deja’s to watch Secretary, since Varick hasn’t seen it, and then play afterwards.  He’s a little gun shy about doing a big scene, after what happened the last time, so we’re going to take it easy.  I made it clear at the play party that I do not put any expectations or pressure on him.  BDSM is heavy, especially when you are new, and I don’t want him to be put off forever.  We’re just going to have fun and go with whatever makes him feel good, that’s all I care about at this point.

Jack was being so sweet last night while we were talking about Varick.  He’s happy that I’m being treated well and says that Varick sounds like a very nice guy (they haven’t had a chance to meet yet, but hopefully soon).  He also remarked that he’s glad I’m seeing someone who is good to me, after that string of lackluster encounters.

Speaking of those other boys, Nelek messaged me the other day.  We haven’t talked much since the beginning of May, for the most part because he had a girlfriend and pretty much stopped messaging me or showing any interest in chatting.  I was a little surprised to hear from him, until he explained that he and his girl had just broken up that day.  He hinted around at getting together but I put him off.  I mean seriously, I am NOT your booty call buddy, nor will I be your entertainment between girlfriends (this is the second time he’s done this by the way).  As cute and fun as he is, I’m tired of that game.  I don’t expect him to not date of course, but ditching me completely every time he does?  Not cool.

On Friday night Mz. F has offered to watch the children so that Jack and I can have a night out to ourselves.  He’s made dinner reservations some place nice, but he’s keeping it a secret.  All he would say is that I have to dress up a bit, and that he can hardly wait.  I’m curious, but I don’t want him to tell me where we are going.  I am REALLY looking forward to it at any rate :D

Saturday night is Pride Sex Party at Goodhandy’s.  We were trying to work it out so that all of us could go, but unfortunately we could not get sitting for that night, so Jack has generously offered to stay home and let me take Mz. F and Varick.  I’m disappointed that he isn’t able to come with us, but our regular sitters are out of town and he doesn’t want a new person watching the little ones for such a prolonged stretch the first time.

Neither Varick nor Mz. F have ever gone to a sex party at Goodhandy’s so I’m quite pleased to be taking them there for their first time.  I imagine the place will be extra crowded due to Pride this week, but the more the merrier in my opinion!

I’ve been doing a lot of cleaning and organizing in the house so far this week, and Jack has given me a long list of things to get done before the end of today.  I like having the place tidy and organized before company comes, so that I don’t have to worry about doing much while they are here and can spend time visiting.  Jack only agreed to let me go out with Varick on Thursday night because I swore I would get the list finished.  If I don’t, then I’ll have to cancel, and I really, really, really don’t want to do that.

Blogging might be slow for the rest of the week, since I’ll have company and be quite busy around here.  There’s a good WTF? Thursday post lined up though, so be sure to check in for that (it’ll be password protected because it’s a tad graphic, so make sure to get on the password list if you haven’t already).

*Title courtesy of my junk mail folder

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During a late-night conversation, Nelek and I came to something of a crossroads in our ‘relationship’.  Long after we had said goodnight I lay awake, pondering the direction I’ve been going in terms of polyamory and dating.

“You have feelings for me” he stated, without any uncertainty at all.

“What makes you say that?” I inquired, honestly unsure of how to respond, since it had sort of come out of nowhere

“I can tell, by how you are with me, the way you act when we are together”

Geeze, call me Miss Obvious.  I need to work a little better on those emotional cloaking devices.

The conversation went on and we established that while he certainly enjoyed my company, he’s only interested in something very casual.  I assured him that I am indeed fine with that, and that having feelings for him does not necessarily mean that I was looking for anything more than what we have.  In fact trying for anything more, even if we both wanted that, would be an exercise in futility.  As much as I like him, he’s too young and inexperienced, and I’m too jaded and impatient.  Those are only a couple of the reasons that dating him would result in a bitter break up.

I can’t control that fact that I care for him.  I tend to easily care about people, even if I am not intimate with them, so it only makes sense that perhaps those emotions would be somewhat magnified in a sexual relationship.  It’s also worth pointing out that the current attachment is really just a whole lot of NRE/infatuation and not based on the kind of affection that is developed slowly, over time.

Is it pointless for me to continue seeking casual relationships when I know that at least half the time I am probably going to develop feelings for the object of my lust?  Perhaps it would be in my better interest to only seek persons who are interested in dating more seriously from the beginning, rather than trying to change the rules part way?

Lack of time for secondary relationships was the main reason that I began shying away from them to begin with.  I felt I was spreading myself too thin as it was, and that it was best to only date casually, avoiding any unrealistic expectations of commitment.

That was a different time however, and now I am back at the point where I am confident I could take on a secondary and be able to give them adequate time and attention without overwhelming myself.  That doesn’t mean that I’m not also open to casual dating, I think I’m just beginning to miss having someone to spend time with regularly.

At the same time, I’ve begun to wonder if I’m just being selfish?  I mean, I already have a wonderful husband, great friends, everything else I could ever really need.  Maybe I don’t have any right to want more than that?  Maybe I’m just being…greedy.

See You Again by Miley Cyrus

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On Friday afternoon I was chatting to Nelek online.  If you’ll remember, I haven’t seen him in some time, after the utter disappointment that was our last ‘date’.  To clarify, it went like this:

Drive 1.5 hours in the snow to his house

Watch TV and cuddle on his bed



He falls asleep

I lay there and contemplate smothering him with a pillow

He wakes up the next day as I am leaving

Needless to say I wasn’t really keen to drive aaaaaaaaaaall that way again for such a lame experience.  He’s been promising since the end of February that the next get together would be more enjoyable, and that he would make it worth my while.  I’ve been putting him off since then, which wasn’t hard since I was sick and busy and then sick again and then gone and then back and then sick some more.

Anyway, he invited me over on Friday night, to watch movies and there were certainly hints of more lascivious intentions as well.  Since I didn’t have any other plans and I felt like being a little spontaneous, I accepted and got cleaned up and off I went.

When I arrived at his place we decided to grab something to eat and then bring it back and watch the movie.  Despite the fact that our last date did not go as planned, he’s just so darned cute and sweet, it’s difficult to turn him down.  Plus he’s got a really hot body and such a genuinely great personality, I really like spending time with him.

We got back to his house and ate our food while we watched the first part of Harold & Kumar Go To White Castle, which is the stupidest funny movie ever.  After we were done eating we cuddled up together on his bed.  He’s super touchy-feely, just like me, so we get along well that way.

Before long the cuddling led to groping, and kissing, as it often does.  I nibbled his ear, and then gently bit his neck, which drives him wild, and I could feel him getting hard against my leg.  I love having that effect, hee hee.

Then I was sitting on top of him and we were pulling each others clothes off, and kissing some more, and when I dipped my head to lick one of his nipples I thought he might explode underneath me.  I held down his arms so that he couldn’t touch me as I licked and sucked on one, and then the other, and then his chest and down his stomach.  Passing over his cock, which he could have hammered nails with, I kissed and nibbled his thighs and then his balls while he twitched and squirmed.  I let his hands go so that he could cover his face with a pillow and groan into it when I took him in my mouth.  We didn’t want to disturb his roommate with our antics.

Now, having seen his cock before I already knew that it was quite substantial in size.  In fact, after R I’d say it’s the largest one I’ve had the pleasure of playing with.  It hadn’t occurred to me that a standard sized condom would not be sufficient.  They ARE stretchy, after all.  Sure enough, we ran into a problem when some minutes later it was time to move on to the fucking.  After rolling it on, with some difficulty, I discovered that there was no way it was going all the way on.  In fact, there was at least 2 inches of uncovered penis between the base and where the condom ended.

“That’s really tight” he commented.  Yes, it certainly was.

“Well, next time I’ll know to bring the XL sized ones” I giggled, which made him grin smugly.

Taking stock of the situation I asked if said too-small condom was cutting off his circulation

“No, I think it’ll be ok, and there is no way in hell it’s going to slip off”

Well, alright then, off to the races!

We kissed hard while he pushed into me.  I gasped into his mouth, arching beneath him.

“It feels so good to finally be inside of you” he breathed into my ear as he started thrusting.  I wrapped my legs around him and dug my nails into his back while we fucked.  This only encouraged him and he ground himself against me, hard and deep, so that I felt every inch of him inside of my pussy.

Much later, he came with a guttural moan, and then slowed, and eventually went still, his cock still buried inside of me.  I kissed his chest and gave his chin a playful nudge with my nose.  He just smiled and kissed me, before excusing himself to the bathroom for a moment.

When he returned there was a lot more cuddling, and kissing, and touching of flesh on flesh.  I was laying on my side, head propped up on one hand and my stomach pressed against his.  He planted feather-light kisses down my neck and over my breast.  I let my head fall back and whimpered softly when he took my nipple in his mouth, sucking and biting it slightly.  His fingers found there way between my legs and he rubbed my juices over my pussy lips.

“You’re wet” he remarked with a smirk.

“Very, very wet” as his fingers slipped inside of me.

He teased me until I thought I might lose my mind.  I was on my back beside him and then he was the one propped up on his elbow, looking down at my face and watching me intently while I gasped and begged him not to stop.

He kissed me hard to smother my moaning when I came for him, hips bucking and body spasming.  He chuckled softly with satisfaction when I rolled towards him, my forehead pressed against his chest while I tried to catch my breath.

“You’re shaking all over”


“I hope it was worth your while driving all the way out here tonight”


We were both exhausted and although he had invited me to spend the night, I decided to grab some coffee and head for home.  Neither of us were particularly keen on untangling ourselves when it came time to separate our limbs and sweat-covered bodies.

He walked me out and kissed me goodnight.  I crawled into bed beside Jack an hour and some later.

I’m hoping it won’t be too long before our next evening together.  Perhaps next weekend, if neither of us is busy.  I think a few more nights like that, and he’ll have more than made up for that previous bad date :P

Pony By Ginuwine

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It feels like I’ve had a lot going on this week, until I actually stop and think about it, and then I start wondering, “What the hell have I been so busy with?”

Monday was a holiday here in Ontario; their first ever Family Day long weekend. Family Day is luxury I’d been accustomed to in Alberta for as long as I can remember. We went out for breakfast as a family, lounged about in the afternoon, and then went out for supper as well. It completely threw off my regular schedule however, and so today only feels like Tuesday, which means I feel behind in my week already. Not that I am complaining about the extra day with Jack :)

Nia and I have been hitting the gym four times a week now, which seems to eat up at least a couple of hours on those days. It feels so good to be working out again. I needed to get out of the house this evening, so I treated myself to a new yoga mat and some sexy workout gear. One can never have too many good sports bras or lycra booty shorts.

This weekend I have a couple of dates lined up. Sunday I am having coffee with a friend who I’ve mentioned here before, but who has not been assigned a name as of yet. I did photos for her one Saturday afternoon not long ago, and we’ve hit it off quite excellently. I shall call her Miri, which means ‘mine’ and you can read into that however you will *sly wink*.

Afterwards, I am getting together with Nelek, for coffee and more lascivious things. Due to circumstances beyond my control, I likely won’t be able to spend any time with him again until well into March. Thus, I am going to make the most of Sunday, as they say.

Today was spent indoors, tidying the house while I listened to episodes of Polyamory Weekly on my iPod Touch (a generous Christmas gift from that fabulous husband of mine). Nothing like being elbow-deep in dishwater while Minx purrs on about responsible non-monogamy. She may yet inspire me to try doing a podcast of my own.

Before I leave off for the evening and crawl into bed with Jack, I have a favour to ask! I need some dare suggestions for an adult party. I know I’ve asked for this before, but this time I need them to be short and easily applied to a group of people who don’t know each other well. We’re going to be writing them on slips of paper and giving one to each guest at random. We’ve got things like “Show some skin” and “Introduce yourself to an attractive stranger” but I need quite a few more. So, think about going to a sexy adult party where you might not know anyone all that well. What sorts of dares would you like to see people do? What would you be willing to do? Leave me some comments please :D

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Beer?After the complete flop that was Loki (he was totally non-committal as far as getting together went and I only had patience for that the first week) I decided not to mention new guys, and waste perfectly good names on them, until something had actually come of it.

So, last night I had a date with a new guy, who I’ve been chatting to for a week or two. He’s not exactly local (he’s an hour and a half away) but close enough that we can hang out once or twice a month I think. Plus we can meet in the middle or he can come out here.

He’s younger than me, only 21, which doesn’t seem like a lot since I am only 25, yet I feel a bit like a Mrs. Robinson**. Perhaps because I’ve already lived through an awful lot of experiences in that short time. He seems fairly innocent, which I’ll admit makes him greatly appealing. Not because I want to corrupt him (ok maybe a little) but because that wide-eyed wonder reminds me that there are still plenty of discoveries to be made.

Before I get into the details of our evening out, he gets a name. Nia lent me a book about choosing names based on astrology and personality types. The guy in question is a Taurus (the highest match for my Virgo self, LOL) and so I’ve decided to christen him Nelek, which means ‘horn’ because it’s amusing, and pretty suitable in my opinion.

Anyway, all of that taken care of, on to the good stuff!

Nelek and I had arranged to meet in his city and then have coffee together and hang out. I made it very clear that I didn’t want to attach any expectations to this date because of my personal rule regarding not putting out on the first date. Really, I prefer the initial meeting to be about getting to know each other, without any pressure or presumptions about sex. He agreed with me on all points, and so a time and place was solidified.

Although I had written out directions for myself, I still got lost, and ended up on his doorstep half an hour late. He told me later that he had assumed I was standing him up. I generally do not go into strangers houses, however, his older female roommate was sitting right there and I had to go pee so bad I couldn’t stand it. He let me in to use his bathroom, and to snorgle his adorable lab puppy.

We drove over to the nearest Tim Horton’s and grabbed a coffee and a seat. The conversation was light and entertaining, and he was certainly easy on the eyes. We seemed to hit it off, and had plenty of things to say. There were no awkward silences, which was a bonus.

Eventually the conversation became a little racy for the crowd at Tim’s and we decided we’d better relocate before we started getting stared at (not that I mind). I suggested we check out a sex store, since that seems like a perfect place to go on a first date, LOL.

He directed me to a place nearby. A nice little non-chain place with a great selection. I picked up some penis chocolate moulds for my upcoming party, and we browsed the toys and lingerie. Found out he’s a big fan of costumes, and sexy games. Clearly he needs a little schooling, since he doesn’t know a lot about kink and he’s never purchased a sex toy, but that will come with time.

We left the store and drove around some, just talking and getting to know each other more. At one point we stopped at a park to wander outside but it was far too cold, and so that lasted all of 5 minutes before we hopped back into the truck.

I asked if there were any diner’s open where we could grab some nibbles. He suggested a place he knew and off we went. It was a typical 24-hour eating establishment, but there isn’t much open that late at night, LOL. We flirted over french fries, discussing past relationships and hobbies and all manner of random topics. It was decided that once we were done at the diner, we would find someplace to park and talk some more. I still had time to burn and neither of us wanted the date to end quite yet.

We ended up in an unlit parking lot and sat there chatting for quite some time. There was certainly flirting, but neither of us were brave enough to make a move. Silly really, but after some posturing and nervous glances we managed to get the initial kissing out of the way. After that, the awkwardness melted away and we spent some time making out like teenagers in the front seat. Kissing led to groping, which eventually led to his hand down the front of my jeans while I screamed bloody murder and came all over his fingers. I returned the favour in kind, making him twitch under my touch while nibbling his lower lip.

We were both satisfied and breathless, and since it was well into the wee hours of the morning, I decided I should start the long trek home. I dropped him off and kissed him goodnight before grabbing another coffee and driving back to my place. I crawled into bed beside Jack at 3:30am, exhausted but content.

All in all, I felt it went very well (the fooling around aside). I enjoyed his company very much, and it seems that he enjoyed mine as well. He’s also quite open minded, and willing to try new things. It’s too early to speculate on where this is going, but I’m generally optimistic.

*Steven Meretzky

**A term commonly used for an older married woman who seduces young men.

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