Stiletto Diaries

I’m Not A Whore. I’m A Relationship Technician.

Archive for January, 2006

I found this persons question, and the subsequent comments to be very interesting.

Seems a lot of people agree it really is about living in the moment.

Yes I know that I have STILL not finished all the stories of the threesome weekend, and I do intend to tell the rest of it. But I have other things I want to talk about right now, that can’t wait until later, so try to put up with me until I get back to the good sex posts, LOL.

One of my worst [and sometimes best] personality traits is my inability to take anything at face value. I can’t help but over-analyze everything, picking it apart and examining it piece by piece. I have a hard time just living in the moment. I find it difficult to just enjoy experiences without wondering what it all means.

This is how my brain works. Always has, probably always will. I think, A LOT, about everything, all the time. The thinking only stops when I am asleep.

That is all well and good, except that sometimes I forget that not everyone thinks like me. Some people are able to just take things as they are (or appear to be). They don’t have this unnatural urge to dissect everything that happens to them, they can just be in a moment.

Now there are times that I can stop thinking an just enjoy myself, but as soon as the moment is over, I’m back at it with the thinking.

In case you are wondering where exactly this is going, I’m trying to make sense of it myself so just try to follow along and we can hope that I come to some sort of semi-logical conclusion eventually.

I want people to know that having an open marriage like this is really very fulfilling and wonderful and all that good stuff. It is also HARD and difficult and uncomfortable sometimes. It isn’t always fun, and sometimes I seriously consider putting a stop to the entire thing because I ask myself “Am I really cut out for this? Can I really do this without fucking everything up?”

I think a lot about the practical longevity of this sort of arrangement. I wonder where it is all going and what could be happening five years down the road. I have to keep reminding myself that we are still so new to this and that I should just try to enjoy myself without cluttering it up so much with unnecessary emotional things.

Why must I always be thinking?!?

Take this relationship I/we have with K. He and I talk a lot, get together a couple of times a week, and actually enjoy each others company even when we aren’t fucking. I enjoy spending time with him and I am pretty sure that the feeling is mutual. Still, I know that I am just entertainment until something better comes along, and sometimes that is pretty hard to swallow [although I realize that I could potentially be doing the same thing]. Rationally I know that there isn’t anything wrong with the whole situation. I guess that I just didn’t expect it to feel this way. I don’t know if I really expected anything, I think that I hoped I would be able to not think so much and just enjoy all the fun I’m having.

Sadly, there doesn’t seem to be a way to stop the thinking.

Is it better to not have any expectations in these situations? Is it better to assume that it’s just not going anywhere? That it doesn’t have to mean anything? Maybe even that I shouldn’t allow it to mean anything [at least to me]?

And what if I can’t do that?


I am bitchy and extra-sensitive right now thanks to my period. I probably shouldn’t be allowed to blog for these five days, LOL, but here it is anyway.

Now that everything has more or less returned to normal around here, I can finish the story of our threesome weekend.

I slept very soundly once we went to bed. I woke at around 11:30 am, and stretched groggily, wondering to myself if it had all just been an incredible dream. I curled up next to Jack and nudged him awake. He pulled me close to him and we cuddled and talked for a while. We both wanted to make sure that the other was happy and feeling comfortable with how everything was going. We had a good chat before I decided to get up and get breakfast started. I slipped into one of Jack’s big t-shirts and told him to stay in bed until I came to get him for breakfast.

Then I headed to the next room to say goodmorning to K. He was sound asleep, so I got under the covers and slid over next to him, cuddling up and kissing him on the cheek to wake him. He put his arm around me and we snuggled for a bit, although cuddling with K is more like foreplay, LOL. I told him to save it for after breakfast and that I would come and get him when the food was ready (even though I really would have rather stayed in bed for several more hours, LOL).

I headed downstairs and decided to call my best friend while I was cooking the breakfast. I chatted to her and told her all about what had been happening. She is really supportive of Jack and I, and I like being able to talk to her about anything without having to worry about her being judgmental. I set the table and made coffee and when everything was ready I said goodbye to my friend and went upstairs to wake the guys. I woke Jack up first, and then K, and we all sat down to have pancakes, bacon, and eggs together.

I have to admit it felt a little weird sitting there with the two of them and eating, like this was a totally normal occurrence.

After breakfast was over Jack went to have a shower because he had to run an errand right away. K and I went back to the guest room and cuddled, which turned to groping and then of course fucking. You’ll have to forgive me for not remembering how everything happened, but Jack headed out for a short while and left K and I to hump like bunnies again.

When Jack got back K and I were still in bed, which is where we ended up spending a good part of the day. Rolling around all day with K and Jack was a fantastic way to spend my Saturday.

K had been toying with the idea of allowing me to tie him up. He isn’t into pain or anything, so I wasn’t entirely sure what I was going to do with him once I had him restrained. Not to mention that I am almost 100%* submissive and always prefer to be the one tied down and helpless. Regardless he decided to allow it if I wanted to, and so I got out the leather cuffs (I don’t have enough experience with rope to confidently restrain someone with it who has never been tied up before, and cuffs are just sexier to me anyway). I fastened the cuffs on his wrists and ankles and had him lay on his back on the bed. I used lengths of rope and ran them through the D-rings on the cuffs and then tied him down to the four corners of the bed. I made sure he was comfortable (within reason, LOL) and told him that if he felt uncomfortable/weird/etc at anytime to just let me know.

So now what to do with him? I was seriously at a loss.

You’ll have to check back to find out what happened next ;)

*I say almost 100% because I think that no matter what everyone has dominant or submissive tendencies, but really no one can be one way or the other all of the time.

Jack and I sat down and had a little talk tonight. Naturally he is quite disappointed in me and my apparent disregard for the rules and the well being of our marriage. It has caused him to question my ability to follow the rules in general, which I understand completely.

All I have been able to do is apologize and try (with utter failure) to explain myself, not to mention promise him that nothing like this will EVER happen again.

Being wonderful and loving he has decided that all the internal torture I have been inflicting on myself is more than enough in terms of consequences.

The foundation of this arrangement has been built on our ability to communicate with each other and always be open about our feelings. We can talk about problems without anything becoming heated or either of us going on the defensive.

Trust me when I say that I have learned my lesson. I am not typically one of those people that has to screw up eight or nine times before they ‘get it’. Once it too much in my opinion and I will be following our rules to the letter from this day forward.

Thank you to my commenters for you support and concern :) I love you all and you make this blog worth writing. Pictures and more good smut are on the way, I promise!

I know that some of my tales from the threesome weekend are yet to be told, and I assure you that I will finish the story as soon as I can.

I don’t want to give anyone the impression that once you decide to start playing around outside of your marriage that everything will just go wonderfully and you will live happily ever after. Of course we always strive for that sort of thing, but naturally since we are only human, we are going to fuck it right up once in a while.

I spent some time with K yesterday, and during that time, we broke one of the rules.

The Condom Rule to be more specific.

Jack is understandably angry. I will be the first to admit that it was immature, selfish, and totally irresponsible of me to just go ahead and make an exception in the moment. Especially after Jack and I discussed said rule after the threesome weekend and decided that we had to be more careful.

I know that if our roles were reversed and it was Jack that had broken one of the rules, I would be furious.

All we can do now is keep the communication open and try to work forward from this. I don’t really know what that will mean yet. We are still figuring everything out as we go along. I only know that I feel terrible about the entire thing, and all I can do is apologize and assure Jack that it will never, ever happen again. Hopefully he can forgive me and eventually trust me again.

More on this to come I am sure.

I was feeling like a puddle of goo after my most satisfying orgasm, but the boys were both raring to go again.

So, they decided to take turns fucking my brains out. Kind of like a horny tag team against poor little me.

Somehow I doubt I am invoking much sympathy, LOL.

I don’t clearly remember who went first, or even how many times they switched off. Jack was fucking me for a while, and then K, and then Jack again, and then K again. I didn’t have to do anything except enjoy myself. I mostly laid there gasping for air between screams, my legs hooked over shoulders, around the waist, or whatever other position was decided upon in the heat of the moment. I don’t think I have ever been so thoroughly and completely taken in my entire life.

I felt like a dirty little whore and I loved every moment of it. I adore feeling used, like I am only good for a sex object and nothing more. By the time K climbed on for the last time I was getting tired and sore, but I was in complete submissive mode and just wanted more.

Part of me was like “Oh my GAWD, you’re still not done with me?”, but a larger part of me was like Oh my GAWD, let this never ever end!”

Of course once the men had gotten their fill (not to mention gotten off) and screwed me into complete sexual rapture, they laid down on either side of me and made me feel adored and loved and cared for.

Does it really ever get any better than that?

At some point I think they also spanked me, each of them smacking one of my ass cheeks and making me squeal and squirm between them. Jack could tell that I was really starting to hit sub space and decided I would be totally useless to them if I went off into my own little world. So the spanking stopped for the moment, much to my disappointment, but it was just as well for what Jack had in mind next.

Two cocks and one pussy.

Why not try to get them both in there.

At the same time!

The mechanics of it become kind of mind-boggling.

So after we had all rested and one of the boys had toyed with my pussy and declared that I was ready to go again, we decided to try it out.

Jack laid on his back on the very end of the bed, so that his butt was right on the edge. He had me get on top of him and he slid his cock into me. K stood behind me and tried to push his cock into my pussy along with Jack’s. It took a little maneuvering, and sadly every time K would get in, he would push Jack out. We tried some different things with no success, so then K and Jack switched spots and Jack tried to get into my tight and resistant little cunt while K was already in there. Again every time Jack would get in, K would get pushed out. Apparently there just wasn’t going to be enough room for them to both be in there at the same time.

We abandoned that effort and decided to just do another round of ‘regular’ double penetration. I still can’t believe that I just wrote that sentence and it doesn’t sound weird to me, LOL.

The night was turning into an Iron Vagina triathalon.

Jack laid on his back and I straddled him, letting his cock slip into my pussy. I rocked my hips while K got the lubricant. In a moment I felt him pressing the head of his cock against my ass. I laid against Jack and relaxed. Despite the hours of fucking that had just occurred it was still a tight fit. Jack wasn’t able to do much thrusting from the bottom, but K started pounding my ass again while I squeeled my head off like a cow elk in heat.

Ok I am so sorry for the allusion to a large and very unsexy quadruped, but I have been DYING to use that phrase, and well, I just had to.

Anyway, K fucked my ass until he came in me and we collapsed onto the bed again for more cuddling. I was in such a mindless stupor that I don’t really remember what happened after that. According to a reliable source we fucked some more (just one on one, no more DP of any kind, LOL) and then finally called it a night.

Or morning, considering it was nearly 6:00 am!

K slept in the guest room and Jack and I went and slept in our own bed. We were wishing we had already purchased our king sized bed because then we could have all slept together. But I like to spread out when I sleep and so does Jack (I have no idea about K since I have never slept with him) so we decided to split up for the few hours sleep we were going to get.

The start of the next day will also be the start of a new post, so check back soon :) Hope you enjoyed this installment!

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1. The peak of sexual excitement, characterized by strong feelings of pleasure and by a series of involuntary contractions of the muscles of the genitals, usually accompanied by the ejaculation of semen by the male. Also called climax.
2. A similar point of intensity of emotional excitement.

The three of us were on the couch, completely naked, and watching the DVD that K and I had made. I don’t remember the exact order of things, but Jack and K started to fondle me again, and I was loving every minute of it.

We ended up on the livingroom floor, K with his head between my legs and Jack working on my nipples. If you can get in on a threesome with two men I highly recommend it, LOL. Anyway, K was licking my clit and fingering my pussy while Jack licked and sucked and pinched my nipples. I laid there and just enjoyed the attention, it felt so incredible. I can’t even remember anything in detail because I don’t think I was really conscious. I just remember how good it felt and I don’t even have the right words to describe that in any sort of articulate way.

I felt the orgasm building.

It was so close I could hardly stand it.

Just. About. There…

Suddenly then the dam burst, and I came so hard I think I almost died. I was screaming I am sure, every muscle in my body contracting involuntarily. Jack said he has never seen my back arch like that. It felt like it lasted forever, although I am sure it was no more than a minute. I think I totally blacked out for a split second while the waves of pleasure washed over me. I would say it was up in the Top 5 best orgasms I have ever had. Maybe even the Top 3. K’s fingers were totally coated in my cum.

When I finally stopped shuddering I just lied there in a total daze, panting and feeling dizzy. I think that all the blood in my body rushed to my genitals and left me light headed. Jack and K cuddled me on either side, making sure that I was ok. I was better than ok, I was in a state of total orgasmic bliss, LOL.

We decided that the floor was not very comfortable, so we all went upstairs and cuddled on the guest bed for a while. Now that I was satiated, they didn’t let me rest very long. I was still only half aware of anything besides the tingles running through me after my earth shattering orgasm.

More of the story will be posted soon :) I hope that everyone has a great weekend!

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So K came out of the bathroom…

Jack and I were kissing and groping each other and I thought I could hear K come into the bedroom. I had my back to the door and Jack was doing a good job of distracting me. Jack reached down and pulled my shirt up and over my head. I felt K behind me, he unhooked my bra and let it slide off my breasts.

I unbuttoned Jack’s shirt and pulled it off of him before turning my attention to K. He was kind of standing back from us, but I motioned him over and started kissing him, and then unbuttoning his shirt. One of them went after my belt and then pants, stripping me down. I unbuckled K’s belt, and then unbuttoned his pants and pushed them down. I turned my attention back to Jack and took of his pants as well. We were all naked and K was sitting on the end of the bed, with his cock in my mouth, and Jack was behind me playing with my pussy.

Once he had me good and wet, Jack got onto the bed and lied down on his back. He beckoned me over to get on top and ride him. I obeyed, straddling him and lowering myself onto his rock hard cock. I moaned and started rocking my hips. We carried on for a moment or two, and then Jack suggested that we try double penetration, since he knew I wanted to at least attempt it. K had no objections to that, so he got onto the bed behind us and positioned himself some way so that he could fuck my ass.

I tried hard not to tense up. I was expecting it to be excruciating, but I really did want to see how it felt. I felt K’s dick nudge against my ass and I held on to Jack. I think that he whispered to me to relax, and I did. K was very gentle (as always) and pushed into me slowly, making sure I was ok before he slid all the way in. Once K was in me, he gave me a moment to adjust to the sensation of being so filled. It wasn’t painful, just very unusual; there isn’t really an accurate way to describe it. K started thrusting, very carefully, to see if I would be able to handle being fucked in both holes at once. I whimpered, and then groaned, and before long I was practically screaming. It felt so good and so dirty, I couldn’t even thing straight. Jack encouraged K to fuck me harder and I felt like I might pass out from the pleasure. I didn’t have an orgasm, but it felt so incredible I didn’t even care.

Finally K thrust into me a few more times and came in my ass. He pulled out and got off of me; all I could do was collapse onto the bed beside Jack. Jack asked me if I was ok and I think I mumbles something about being fine, he cuddled me and made sure I was really alright. K lied down on my other side and cuddled me as well. They both stroked my back and my butt and it felt almost better than the fucking. I totally enjoyed being the center of attention, I just lied there and soaked it up.

We were all thirsty, so we went downstairs to get something to drink. It was kind of a strange sight to have two naked men sitting on our couch, but I wasn’t complaining, LOL. I sat between them again and we decided to watch the DVD that K and I had made earlier in the week (since he hadn’t seen it yet). We turned it on and K and I chatted about how strange it is to watch ones self having sex.

Anyway, that is just the very beginning of the evening, and of the weekend overall. Much more to come, but it will have to wait for later! Check back soon :)

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Ah, the weekend…

Were to begin?

At the beginning I suppose, LOL.

Jack and I had a kid-free weekend planned, to celebrate our four year wedding anniversary which happens this month. We rarely ever have a lot of time to ourselves and we have been planning this since November. K got added to the plans last-minute as he only recently came into the mix and Jack was eager to fulfill a particular fantasy of mine. Given that opportunities like this do not present themselves often, we decided to take total advantage of the weekend and fill it with as much fun as we could manage.

We planned to go for a late supper Friday night, and then pick up K on our way home and have him stay over for the night. That was a pretty big deal for me because first of all I have never had Jack meet any of my ‘friends’. And even though he assured me otherwise many times, I still worried that he might have a momentary lapse and maul the guy if he put his hands on me. Secondly, I have never had any of my ‘friends’ over to my house, so I wanted everything to be nice and tidy and impressive.

We got ready to go out for the evening, I was already feeling nervous (of course! I have become this freakish, nervous animal all of a sudden, LOL). We went to dinner, which was fantastic, although it did nothing good for the nausea I had from my nerves. I just felt over-full and like throwing up, LOL (I know, such a sexy picture I got going on here).

When we finished dinner I called K and told him that we were on our way over and that we would be there in about 15 minutes. When we arrived at his place I got out of the car and went in to get him. K was on the phone, but otherwise ready to go. He was dressed nice and looked really good. He told me he was nervous and I said that Jack and I were too, but that I was sure it would all be really good.

We got into the car, Jack introduced himself to K, and we headed for home. K lives WAY too frickin far from us, LOL, and most of the drive passed in a sort of awkward silence. When we got to the house I gave K the ‘tour’ and offered him a drink. Jack had a drink too and we all sat down on the couch and watched something on Showcase. I was sitting in the middle, Jack on my left, K on my right. It was kind of a strange feeling to be there with both of them. I could tell that K wanted to touch me, but he was nervous, maybe about what Jack might do or maybe just nervous in general. I decided to wait and let Jack initiate whatever was going to happen.

We watched and chatted for a while, and then Jack asked me quietly if I wanted to go upstairs. I said that I did, and we got up from the couch. Jack told K that it was ok if he wanted to touch me, and that he wasn’t going to freak out or anything. We all went upstairs and K had to use the bathroom so Jack and I went into the spare room and started kissing…

And that is where I will leave you for tonight ;) It’s late and I need some sleep (since I didn’t get very much on the weekend, LOL). Hope everyone had a great Monday!


what a weekend I had!

*Big Satisfied Sigh*

Every fuckable orifice I have is aching.

I have sore muscles that I don’t get from going to the gym.

I had more orgasms in 24 hours than I average in a week.

More details to come…