78. Three’s -not- a crowd?


I feel a bit naughty with how I ended my last post. It sure inferred a lot of stuff with my last line – and I fully intended for that.  I like doing that in a post (maybe I will do it on this one, hint hint).  It is fun to let your imagination run wild, as it is likely more exciting, daring, and shocking than real life.  The problem is, it is reality, not a story. But boy, what a story it could be!

This post may be different from my others. I typically share a situation or feeling and try to take it through to conclusion. I try hard to be authentic, accurate, and open with you, thus probably err on the side of TMI. But even while being a bit too verbose I do try to provide you with a read that has some forward momentum to it. For this post I am far from a conclusion and don’t know where this will go, but it sure seems to be leaning a certain way.  Flooding you with my prose won’t make for a good read so I’ll do my best to revise and edit my pounding out of random thoughts.  You can be the judge if I am successful or not.

If you haven’t read about Kayla, you can do so here and here.

Despite all that Kayla has revealed to me (and I to her), I still can’t let myself think of her in “that” way. I recognize she is an adult, but a young one at that. I am stuck on the fact that if one of my sons had a sexual relationship with a woman who was 25 years older than they are, I would be highly suspicious of that woman. Despite my tendency to assume the best in people, and to not judge them on a single criteria, that tendency is squashed when it comes to the thought of that. I guess since I would not look fondly upon it, it is hard for me to open myself up to the possibilities.

HOWEVER, Mike looks at it differently. The primary difference is that again, I think I see myself as more motherly in my relationship with Kayla. Mike on the other hand, sees her as a “hot young thing” that wants us.   After talking with Mike, I figured before we get to riled up in our differences, let’s find out how she see us. Perhaps she isn’t even interested. Well, that got clarified both yesterday and today.

Mike did say that now that Kayla knows a bit about our dynamic that all rules apply when Kayla is around.   He said he reserves the right to punish me with her watching, but would be mindful of not making Kala uncomfortable. I think that means he won’t actually do it, but he likes the threat of me thinking that he might. Honestly, I like it too. That is, I like the threat that it could happen, but honestly, I don’t want it to.

Sure enough, Kayla came over about 1pm yesterday as she just had morning classes. I jokingly told her she was just a voyeur and came over just to see my tits. Her sly response was “Maybe, but that was just a bonus. Really, I want to talk more.”

So we talked as I went through my daily chores. It was nice to have an extra set of hands to fold clothes and stuff like that. She shared more details about her sexual experiences as well as her views on both relationships in general and her various relationships specifically. I learned that her best friend is 28 and her best friends’ boyfriend is 31. This is the couple that she often joins with in a threesome. I didn’t realize they were that much older than her. Granted, 7 and 10 years isn’t huge, but to me a big difference between 21 and 31. I guess that is my personal hang up.

In turn I ended up sharing more with her about our DD lifestyle. Kayla asked a lot of questions and it got to the point that it seemed pointless to hold back certain things.   While I didn’t tell her everything, such as the relationship with John and Donna, I told her plenty. I ended up giving her the name of my blog and told her that it would completely reveal my DD journey to her (as well as what goes on with John and Donna). I did tell her that I blogged about her and used her real name. Oops, I hadn’t thought about that when I first mentioned her. Anyway, she was fine with that and was anxious to look it up. She got on her phone right away and started reading some of it – enough to make me blush – hey, I never knew that even my boobs turned a bit red when I blush. Is that normal?

Okay, so I am basically fully out when it comes to Kayla and being a pretty straightforward person I just put it out there and asked her if she had any inclinations about sex with Mike and I. She didn’t say no, but she was a bit hesitant. She said the thought did cross her mind but she wasn’t sure what she wanted. She did say she has always liked older people – all her friends were always older, even when she was in high school, I knew that as a freshman she seemed to be friends with most of the seniors, and as a senior, all her close friends were in college or finishing up college. She did say she had a bit of a crush on Mike when she was younger, but hadn’t really thought of him in “that” way.

She of course then turned the tables and asked me what I thought. I told her that I was very fond of her company, enjoy being around her, and think she is a wonderful human being. I told her she was beautiful, both inside and out, however, I am stuck not just on the age difference, but by the fact we have known her since she was so young that I have a hard time thinking of her in “that” way. I told her that it is hard for someone to think of their parents or their kids as sexual beings. Everyone else can be wild sexual beings, but not parents or children.   She laughed as she agreed that she can’t think of her parents that way either. I told her I think of her more as an extension of the family, closer to a daughter than just a babysitter or neighbor. Thus my hang up.

In all the conversation went very well. I did sense that she was unsure, albeit perhaps for difference reasons than me. So, I felt relieved and that there was nothing imminent to justify worrying about this.

When I talked to Mike last night and shared the conversation I had with Kayla, he got pretty excited over the prospects. While Kayla didn’t say she was game, it seemed clear that she likely would be. Now, this could have become an argument between Mike and me, but I kept my cool.   I told him that there is absolutely no doubt or hesitation that I would go along with his wishes as I always fully intend to honor my sexual submission to any of his wishes. (It’s in the contract!)  That being said, I did have reservations.

I explained that while we know Kayla well, we don’t know her that well. I didn’t know about her sex life and while I don’t find it shocking, it does raise safety questions for us. We have kept our “swinging” to just John and Donna. Expanding that opens not only us up to STD’s and the like, but opens up John and Donna. We can take precautions, but, that is a change in our “routine” and we would have to stick with it.

More importantly, as Kayla revealed more things to me I have found her to be a bit needier than I previously perceived her to be. She has some emotional baggage and my arm-chair psychological diagnosis is that some of her sexploration is to fill a need to be loved and accepted. Not to knock people who fit that description, but, I don’t know that I want to invite that type of neediness into my “inner circle.” My life is very good right now, so why potentially complicate it?

My next reasoning is that thus far if somehow any of my children found out about TTWD, I would not feel any embarrassment or shame. A bit uncomfortable yes, but more uncomfortable FOR them because I think they would be the ones more freaked out by it.   However, if we were to have sex with Kayla and they found it, I would feel terrible. This is someone they’ve known for a long time and is more of a peer to them. It would be way uncomfortable for me.

My final reasoning was that it was just too much, too fast. I tend to take a situation, do a deep dive into all the feelings and permutations of what if this, what if that, and then make a decision and move forward. As a submissive I have given up a lot of that in deference to Mike, and it has taught me that I don’t need to be in a rush to decide things. Of course, in our new dynamic it is not about me deciding things but I still get to be an advocate for my feelings.  I feel I must advocate for taking it slow, if at all. Last night after sharing all of this with Mike, he ultimately agreed with me.  Not so much that he saw it my way, but he saw that it was important to me and was willing to go along with it and not push the issue.  Then today happened.

Kayla came over again. Back-to-back visits when she is not there to watch our son is rare, but, Kayla wanted to talk.   I was very open with her and shared every concern I shared here…both about sexual diseases and about neediness.  It was a very emotional conversation for her and while I got to understand her even better, it didn’t change my concerns.  One quick fairly comical aside – At one point when I was talking to her about all the reasons we should cool it and just put off even considering this for some time I told her, “I know it is very hard to come across as the prude when I am standing here with my tits out, but. . . “   Anyway, it got a laugh and helped break a bit of tension that had built up. Maybe you had to be there to get how funny it was. Oh well, next . . .

Then Mike came home a bit early and said he had a few things to finish up but would work out of his home office. Kayla already knew I had talked to Mike about all of this so when she saw him she boldly asked him his thoughts. Mike looked at me and I recognized his face as being the face of “oh crap, I don’t want to say something different than you.”   I told him, “Sir, whatever feelings you want to share about this is fine by me. You know I’ll support you, Sir.”

I thought he would perhaps take the opportunity to say, “Okay, let’s all get naked” but he didn’t. I was relieved when he said, “Kayla, we love you and want what is best for you. We don’t want our sexual appetites to cloud that.  Despite whatever fun or extra connection we could have by having sex, it may end up being a terrible thing for you. Let’s just take our time talking through it, understanding everyone’s needs and expectations better, and see where it goes. No harm in waiting, right?”

Kayla agreed, but reiterated to him what she told me previously. “I am not some fragile flower. I understand the pros and cons here.   All this talk makes it all sound so clinical and planned, which is a big turn is off.   I figure if it happens it would happen when we aren’t expecting it, and I certainly don’t want to have to schedule it. So, fine, yes, let’s just cool it. It sounds like we all want it on some level, so if it happens, it happens.”

Wow. I found her response very erotic! But I found Mike’s response an even greater turn on.

Mike responded, “If it happens, it happens. . . ‘Sir.’”

Kayla and I both smiled and she repeated, “Yes, if it happens, it happens, Sir!

NEXT: 79. Anxiety, Resentment, Jealousy, Guilt.

10 thoughts on “78. Three’s -not- a crowd?”

  1. Two worthless thoughts:

    1- This is the person most trusted with and by the son. Does anyone want to screw up a wonderful fallback for his care? Are orgasms worth trying to find another trustworthy person with her institutional knowledge?

    2- Employer & employee, think real hard on that one. This type of situation makes for great case law.

    I’ll leave with good advice I received as a kid. If you want something, work for it. Then wait 90 days. If, after 90 days, it still seems like the best call then get it.


    1. Yep on all points, and that last point is exactly where I at. Just cool our jets and wait awhile and revisit later so we have time for our minds to percolate more on the pros and cons.


    2. Oh. And not worthless thoughts. I value them as I value any suggestions. Not that I’ll always follow the suggestion, but I still appreciate it none the less. In this case, it hits some of the issues I raised with Mike and Kayla.


      1. I’d always rather have 20 suggestions than 2. Maybe it’s just me but I listen closest to my biggest detractors. They are the ones who will say the things that your greatest followers might be thinking! Openness to input has taught me a lot.


        1. Right on. Mike often calls me a masochist when it comes to feedback. I like feedback, even if it hurts. I am strong enough to discern between what is intended to be helpful vs hurtful and don’t take every detractor as being a “hater.” I tend to be highly self reflective and chances are I am tougher on myself than anyone else and that I already considered whatever someone says. I enjoy it when someone comes up with an angle I hadn’t thought of. Keep any suggestions coming. Will have a post soon on an update re where things stand.


  2. Wow. I know what you meant by Mike’s response. I can understand why you have some conflicting feelings though. I look forward to continuing to follow your journey.


  3. Hi Kayla, since you are going to be reading this blog thought I would let you know that I’m an avid reader of Jen’s journey. I think it’s great that you are open to idea of submitting to Mike, I know that for Jen it’s been an amazing journey that has turned her life into a fairy tale. I do agree however that you should not dive headlong into submission w/o some precautions. It may sound clinical, but there are valid concerns that Jen raised. Just because Mike thinks you are a hot young thing doesn’t mean you should drive a wedge btwn them.

    I understand your concerns Jen about ruining your relationship with Kayla, but you may find that your hangups become irrelevant in the heat of the moment. It seems a certainty now that Mike will provide a scene with you for Kayla’s edification and I’m sure she will wind up over his knee sooner than later. If D/s has helped you overcome insecurities then I am hopeful that the emotional neediness that Kayla projects will be helped as well.

    Liked by 1 person

    1. “It seems a certainty now that Mike will provide a scene with you for Kayla’s edification and I’m sure she will wind up over his knee sooner than later.”

      That’s the way it looks to me also. But I also think that sooner or later Kayla will be over your knee as well, Jen. I know you gave Kayla permission to write her contract any way she wanted/needed, but I think that is what she many need and is looking for otherwise why would she drop in on you so frequently?


      1. She has always visited a lot, but more so lately. Not sure I would take that to mean she wants to be submissive to me, but, anything is possible. I take it as she is still working out what she wants and is hungry for more information about my feelings, Mike’s , and her own. The more we talk, the better everyone is feeling about the possibilities. In all our discussions, we haven’t addressed what her “submissiveness” would be like. She is still contemplating that.


        1. Hello Jen, I have now read every post in your blog at least once most twice and those involving Kayla more. Some observations:
          While you are committed to being submissive to Mike you do have a dominant side that needs expression. You seem to enjoy punishing Donna. I think you said it was a great turn-on or something like that. You also enjoy sex with women. I remember your comment about wishing you had a “strap-on”.
          Kayla knows about your dynamic with Mike and seems very curious and interested. She also seems to indicate that if this goes forward she would need to submit to Mike. She called Him Sir when she said, “If it happens. Sir”. However she also said she never really thought of him in “that way” (sexual way). But it is you she wants to see naked. She tried several ways to get you to undress in front of her. I am sure she will benefit and enjoy her submission to Mike, if that happens, but it is you that it seems she is primarily focused on. So whether she submits to you formally or not it seems it is you she is looking to submit to. I think that’s beautiful. I hope for all your sakes it happens.


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