Protected: Email to Sir regarding this weeks upcoming “events”

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A sense of peace and contentment

I’m feel largely at peace today for some reason. I don’t feel at peace all that often so I am trying to savor and enjoy it while it lasts.

I feel good that I set boundaries with Jason when told him that I still want to date other people. I don’t really feel the need to fuck anyone else. Honestly, I really only like having sex with one person at a time. Now dating is different. I want to date other people. It makes me feel safe and I need to keep doing it for right now. And if one of these dates evolve into something more? Well, I will just have to figure that out if and when it happens.

Something kind of strange. I find myself thinking a lot about what Jason was like as a kid. Like 5 year old Jason. 13 year old Jason, etc. I mean, I really wish I could see video! This is so weird to me. Someone’s childhood is not usually something I think much about unless the subject is brought up. He has mentioned things in passing and it seemed normal enough so why the fascination? I have no idea.

I even feel at peace with Sir’s current role in my life. I love our outlandish journey and no matter what twists and turns inevitably lie ahead, I know he will always be a profound and influential person in my life.

Sunday afternoon delight

Jason came over around 11.30 am yesterday. He had made reservations for 12:15 for brunch. It takes about 15-20 minutes to get to the restaurant. I asked what him what are we supposed to do with extra time. He said “You are about to find that out”. 

There it was. That urgency. That intensity. His need to have me NOW. I love that. Over the top passion is so intoxicating to me. He looked and smelled so good. There was no chance of resisting him. I remember the vulnerability of that annoying me for a second before he took off my dress and got me back to my room. He pushed me back on the bed with an aggressiveness I haven’t seen in him before although I knew it was there. This turned me on despite myself and he knew it.

I was horny and I knew could do my part. I thought about my recent conversation with Sir about having to struggle to have an orgasm during sex. He said if he tells me to cum when I am with Jason, I should be able to do this just as quickly as I always do for him any other time. This has been a struggle in the past. A mental block. One with a very obvious explanation. I felt like I was betraying my submission and while I’ve gotten progressively better at it, I still struggle. 

As soon as we started, it felt so good and my anxiety about tarnishing my submission was nearly gone. I know this was Sir’s goal from the start but it still makes me sad. But for now, while in this moment, It felt damn good. Jason continued with this new level of roughness. Not painful but aggressive and confirming what I already knew. I’m a bit of a pain slut and his forcefulness was triggering the long dormant pleasure centers in my brain.

I still thought of Sir though. Perhaps I always will. Hearing his voice in my head along with the amazing sensations pulsating throughout my body was all it took. I rolled my eyes back and felt the warmth of the orgasm spread throughout my body. Jason stopped and watched me. “Damn baby, that was intense and quick.”

We got dressed and went to brunch and had a great time. We talked a little about everything. It is easy to be with him. He is charismatic with a hint of mystery. Typical Aries man. We did talk about the situation from Friday night and he apologized again. I told him that I really care about him and that while I am not sleeping with anyone else, I do date. I am not emotionally in a place where I can devote myself just one person. I told him that I hoped that was ok but if it wasn’t, I understand. He said it was fine and this is actually was ideal for him. His daughter and job take up a lot of time and most women eventually need more than he can give. Well, not me! I think we both felt good with how our situation is now but we promised to be open about any changes that may arise in the future.

We walked around the downtown area for awhile and then decided to go back to my place to watch a movie. Of course, not long into the movie, we started fooling around again and that was…well lets just say I enjoyed it 🙂

So, we will continue on as we are. For now at least. When his mom comes up for a visit in couple weeks and can watch his daughter, he wants me to go for an overnight trip to the San Juan Islands. Leave Saturday morning and come back Sunday night. I didn’t say yes or no but the thought of it gives me a lot of anxiety. I don’t know if I want to do that. I guess I’ll think about it and of course check with Sir to see what he thinks. Part of me feels kind of guilty about my continued dependence on Sir but we were in some version of a D/s relationship for years and you just don’t stop that over night. Kink is an addiction and a tough one to kick.         I don’t feel ready to completely let go. This is probably part of why I am so hesitant to get into something serious although it is definitely not the only reason. I don’t want to make any decisions right now. I just want to enjoy the moment and take it day by day.

Friends of the opposite sex

I have a very good friend and coworker named Richard. He is the best salesman I’ve ever come across and I am lucky to have 3 accounts with him. I never worry about them leaving. In fact, they are the accounts consistently growing. So suffice it to say, he makes a lot of money and has a lot of connections.
Despite this, he is not your stereotypical sleazy salesman. He is one of the kindest, most genuine, big hearted people I have ever met. We have become very close as FRIENDS, over the last two years and will occasionally hang out. He is the kind of guy who does everything big. Forget about trying to pay, he absolutely refuses to even entertain the idea.
Once a month, because he works (telecommutes) in a premier suite in an expensive downtown hotel. He invited me and my best coworker out for dinner and drinks. He always says pack a bag and stay over. No worries about drinking and driving. His wife had a stroke a while back and needs 24/7 care so he usually leaves around midnight to go home. We have the suite until 4pm the next afternoon. Fully stocked, room service etc. Everything is top of the line.
Jason asked me what I was doing and I told him. Mind you, while we are probably more than casually involved at this point, we have no commitment. I do admit I have complicated feelings for him and our chemistry is above average but I have neither the time nor the inclination for more than we have right now. He knows this. We have talked about it. My dating profile on the site where I met him very clearly states “Would like to date casually but not looking for a relationship.”
Long story short, he thought it was impossible that I could stay over night in the penthouse suite of an expensive hotel with no strings attached. Basically saying I was either stupid or lying. To say I was pissed is an understatement! First of all, I’m not a naive school girl. This is not my first rodeo. Plus, I have known Richard personally and professionally for over two years. I have zero sexual attraction for him. Not to mention another mutual friend who is female was with us. I have pretty good intuition and am fairly skilled at reading people. Nothing bad was going to happen to me that night.
Then I thought, why am I even justifying this to him? So what if I was going to spend the night and fuck someone else? I am within my rights to do that or anything else I want. I am a single woman who doesn’t have to put up with suspicious, controlling accusations. If I wanted that, I would have stayed married! I love being on my own. I’m not saying I’ll never settle down but as for now? No way. I love my adventurous, unpredictable life. I’m completely honest about that and never pretend to want otherwise.
I know it’s been a big adjustment for Jason to go from being an every other weekend Dad to having full custody of his 12 year old daughter. It’s only been a little less than a year. She sounds like quite a handful on top of it all. So of course, he isn’t as free as he once was and it has put a serious damper on his social life. Trust me, this thing with me would probably have been a nonissue if he didn’t have his kid. This man could easily find a different woman everyday of the week if he wanted to but now most women want more than he can give. I don’t. In fact, it would seem I want less than he can give. Maybe that’s my appeal. I don’t know.
He kept texting me and expecting me to answer right away. Um, I am hanging out with friends. I can’t sit here sexting with you all night!! How rude it is to be texting while out to dinner or interacting with real live people? Wtf? I know he was drinking but he got stupider and more annoying as the night went on. Finally I told him, I’m done texting for the night and put my phone on DND. There were about 8 more texts when I checked in the morning. Drunk and stupid texts. This morning he apologized. He asked if I would talk on the phone (which I don’t like to do) but I did. Sigh. He is a real smooth talker. It’s what he does for a living. He makes me think of the pied piper. I accepted his apology but I’m wondering if this is just another example of the life long pattern i have of ignoring red flags. Once someone has won me over there isn’t much they can do to me turn off. This has led to disastrous consequences in the past. I’m not saying that is what is happening here but I just want to make sure it doesn’t happen again.
He is coming over tomorrow afternoon. I’m not sure what we are going to do yet but do I plan on going over some basic boundaries. Something I haven’t always been great about in the past. I work in a male dominated field, especially in the last two years. I have some very close male friends and in no way would I want to be with someone who was threatened by that or wanted me to only have female friends. Once again, if I wanted that, I would have stayed married.
I’ve been really looking forward to seeing Jason tomorrow. Despite wanting to keep everything casual, I do like him…

How much is too much?

I’m not 100% sure what I think about sending revealing photos. Over the years, I must have sent upwards of 1000 to Sir but other than that, I’ve only sent a handful, mostly to women. I don’t know why but that doesn’t seem as bad as sending them to men. Just another one of my illogical quirks…

I’ve seen Jason probably 8 times and 3 1/2 of these times we had more extensive sexual contact so it’s fair to say I know him fairly well. He has asked me for revealing photos more than once. The first time he asked was about 3 months ago which was before we were together sexually. Sir said I could send one of my nipple ring but said absolutely nothing with my face in it.

He is a man so he loved it of course and wants more. I’m not particularly worried about it coming back to haunt me or anything like that but wonder how much is too much? Is it just as bad to send “tasteful” photos compared to more overt ones? Where is the line and does who is involved change where you draw it or is it the same for everyone? By the way, he has sent me unsolicited pics of himself.

Interesting side note. Jason’s daughter got in trouble at school (and home) for sending a nude photo of herself to a boy she liked. Unfortunately, it didn’t stay with just that boy. Wtf? She is 12 years old!! I guess it happens all the time in middle school. Wow.

Making someone’s fantasy come true

I met with David tonight. When we originally planned to meet, we didn’t realize it was St. Patrick’s Day and everywhere would be unbelievably crowded and not conducive to talking. Finally, I suggested we just get a 6 pack and sit in my car. So we did. Not the classiest date ever but he is as a young guy and as long as he can drink beer on a Friday night, he is happy.

As I believe I mentioned, David recently shared a long time fantasy of serving a dominant woman while simultaneously being in control of another submissive man who is also serving. I told him that when we met tonight that he can give me more details and I would let him know what if any, I would allow.

It’s funny but years ago I remember having this exact fantasy with Sir. I wanted to be the alpha female and in charge of training another woman. While we fulfilled a lot of fantasies, this one never happened. I actually even forgot about until David brought his up.

David and I have become friends in a D/s kind of way so I already know a lot of what goes on in his day to day life so there wasn’t much a need to catch up. Instead, I told to get right to the good stuff.

He had all these ideas and very specific details which included me being very pampered, spoiled and demanding. While it’s not really my personality to sit around doing nothing while being waited on hand and foot, I’m sure I could muddle through it for a few hours 🙂

I listened intently while he went through all the different scenes he dreamed up. He is a good looking guy but the excitement in his eyes made him almost irresistible. I thought again about how that if I was 24, I’d have been completely smitten. He has these large dark eyes that fully give away his emotions. Several times I’ve seen the change in his eyes as he passed through different emotions. It’s fascinating and I’ve never seen anything quite like it before.

A couple of days ago, he sent me a picture of a man he found that was interested in the same fantasy. This guy was good looking as well although VERY young. Even a couple years younger than David. I had mixed feelings about it but after discussing it with Sir, it was decided I should explore further. What could it hurt really? After all, I was in charge.

With my permission David showed this guy my photo’s and he said to him that he really wanted to participate.

I told David I would be up for meeting him but I have rules. I’m not looking for some devil’s threesome and full sexual contact should not be expected. Ultimately, I will have full control over both of them and what I say goes. Fortunately, unlike most men, submissive men don’t have expectations of sex and tend to be happy with what they get. There is a lot of power in that.

Most of the things he talked about were reasonable but that boy sure is kinky! I finally had to shut him up by kissing him which indeed had the desired effect.

I gave him a few dates and times where I could meet so it looks like we are moving forward for now. To be continued….

Back to David’s fantasy

I’m feeling more and more of like my old self. It feels good to stop stressing so much and just live my life. 

With everything going on, I haven’t said much about David lately but we stay in touch on a fairly regular basis. Ever since he shared his fantasy about serving a Dominant woman as well as being in charge of another submissive man whose purpose is also to serve this woman, he has become increasingly fixated on it. He asked if I could meet him to talk more about it so I told him Friday would work.

He said he talked to a few other submissive men about it and wants to know what I think. I told him that I honestly haven’t even had the mental energy to think much about it but I would be open to hear what has found out. Should be interesting…