Here we are. The end of 2020. Just as I believe most people do this time of yeah, I have been doing a lot of reflection about this past year and myself. My career. My relationships with my friends and family. The madness of this pandemic and weeks upon weeks of either total or partial lockdown. My marriage. And yes, my kinks and fetishes. Upon which this blog entry focuses.
Despite pandemic and social distancing, I actually explored myself sexually and spiritually quite a bit this past year. For Christmas last year, Lady Jessica and I’s Christmas gift to each other was a sex retreat and couples building retreat. We went away to it in March, right before pandemic as luck would have it. I mean, RIGHT before. Two weeks later and we would have not been able to go because of lockdown. And it was the results of that retreat that really led to my own exploration this year. Among other things, one something I was able to open up about not only to Jessica but to myself was a kink that I had been playing around with for a long time, that had been causing me a lot of emotional distress. It was escapism, really. But it was making me feel more and more lost and unsure of myself and my own identity. At times it was leaving me feeling helpless and suicidal. It had a lot of connections to a lot of bad stuff that happened to me earlier in my life. In our sessions and workshops with the counselors, we determined that indeed I was using it as an escape. In youth, I had been programmed to believe that was where I belonged. But my adult psyche was fighting it. Part of me knew it wasn’t where I belonged. That was what was causing the internal conflict. The feelings of helplessness.
We also realized that I did have a kinky soul, and a sexual soul, and that I just needed to find my place. We talked about other kinks and fetishes. Ones that I had tried and knew I kind of liked. Ones I hadn’t trued and thought I might like. I was encouraged by both counselors and Jessica to go forth and explore my feelings, and figure out who I was and what worked for not only me, but what jointly work for us as a couple.
So here I am. Thinking about this past year, and that personal exploration. Between the outcomes and discoveries of that retreat, a lot of time to myself during pandemic, and lots of deep talks with Jess I was able to explore myself quite a bit this past year. Some things worked. Some things not so much.
Thinking about the start of my journey, it really goes back to last November (2019). I met a young woman who worked at a Starbucks. We didn’t really know each other. Just costumer-worker interactions a couple of times a week. But we were friendly. I admit I did flirt back when she flirted with me. On one given Saturday after Thanksgiving, Jessica and I stopped in to get coffee while doing shopping. She wrote her number on my coffee cup. Now, Jess has been encouraging me for quite a while to “explore” in what she wanted as an open marriage. I had never been really comfortable with that. For one thing, I am pretty introverted. That kind of stuff doesn’t come naturally to me. The fact I ever landed Jessica in the first place is still a mystery to me. Jess was telling me I should text her. I was like “no way”. Upon saying “of for God’s sakes” she took my phone and texted the number for me. So, yes, Jess was the one who imitated our fling. We met up for a “chill night”. We fucked. We fucked a lot over the course of 6 weeks. She was so cute and so nice. She made me feel like I hadn’t felt in a long time. But, I also struggled with it. Despite open marriage and Jessica’s blessing, it did feel like cheating to me. A lot. And I also struggled with the age thing. So, it ended. It was fun while it lasted. But I feel like it was a bit of a setback for me. It wasn’t right for me. It conflicted a lot with how I saw myself as a submissive and loyal husband in an FLR to Jess. I don’t have any regrets about it. We still talk, in fact. I think she also knew that wasn’t going to go anywhere good for her.
Now we come to February. The infamous Valentines Day cuckolding weekend. So, she’s talked about this a lot. I’ve talked about this a lot. So I won’t go into too much detail here. But, yes, after years of “passive cuckolding” as I like to think of it with Jessica’s work as a porn actress and call girl, this was our first big jump into “active cuckolding”. Something we had talked about for a long time. Something she was never sure she would be able to do. The weekend was incredible, but also riddled with pitfalls that we both fell into. I hadn’t expected she would choose my buddy as her first partner. I wasn’t expecting how well he would take to it, and take to “mild humiliation” of me as I sucked his cock both before and after. Despite what we thought had been a lot of communication between us leading up to it, we still found ourselves unprepared for some of the emotional fallout. We had done way too much way too fast, probably. And the pre-communication between me and him had only involved a couple of house over drinks and apps in the hotel lounge before hand. She wanted it to be a surprise for Valentines Day. It was indeed that. But, despite these pitfalls we fell into, it was in fact a great weekend. But our lack of preparation did cause a setback in progressing in that lifestyle. That plus, you know, pandemic. But, the more I thought about it, the more I liked my role in this cuckold spectrum. I had known I liked the idea of her having sex with other for quite some time. I loved hearing about it. I loved watching videos of her. This was just the next logical step for me.
This summer was the first time I ever submitted to another domme. Mistress Anna, who also happens to be my boss. Terrible idea, which is why I’m not her sub anymore. But, it was what it was. And for a while, it was pretty great. She was the domme that Jessica was never comfortable being with me. Had no problem inflicting pain and humiliation on me. She loved that she had this secret and this power over me. And to be honest, she still has that power. My longest duration of locked chastity ever was under her. She took delight in wearing my key, and teasing Jessica that I had giver her ownership of my cock so easily. She took delight in how easily she could get me to betray Jessica. Lady Jessica and Mistress Anna had joined forces in the control over me. Loved using a remotely controlled lovesnse anal plug on me. And, honestly, it was kind of awesome. It tickled a submissive part of me that hadn’t been touched in years since Jessica was a hardcore domme over me. But, it did come to an abrupt end. She had gotten the better of her senses, knew how bad and how dangerous this was. And I knew she was right. We still have that playful teasing and she still has that mild control over me, but that’s as far as it can go. We’re okay. I love working for her. I love this job. When I started a year ago I wasn’t sure how I would take to this civilian life. It was a big change for me. But it’s been a great change. I am eternally grateful to Mistress Anna. Not only for those weeks of being my dominatrix and humiliatrix, but also just for giving me this chance and this opportunity. It’s all good. It was a mistake, but no regrets as we have both been able to find our footing once again.
Meanwhile, Jessica and Jake had started seeing each other again. Jessica had determined Jake was “in our bubble” and safe, and all three of us had found our way around and out of those earlier pitfalls. While Mistress Anna kept me locked and teased Jessica about owning me, Jessica and Jake had found their way into each others arms and beds. There I was once again seated firmly in the cuckold spectrum. And I loved it. I love how well he fucks her and satisfies her with his huge cock. And to be honest, I love I am comfortable going down on that cock myself and it being “just something we do”.
In September, I had gone to that lifestyle beach party with Jessica where I had met Sarah, which I blogged about earlier. I like Sarah a lot. She’s pretty. She’s funny. Despite our age difference, we have a lot in common and mutual interests. But, the more we talked, the more I found myself finding excuses to avoid taking it to the next step with her. I think part of it was hesitation based on learning experience with the girl I wrote about in the beginning of this article. Taking a step into a sexual relationship with someone other than my wife is hard for me. And couple that with the fact she is married and looking for a bull, and my lack of confidence in being able to be a bull. I ended up telling her I wasn’t sure if I could be what she was looking for. Her response was basically “just give it time”. We’re friends. And to be completely honest I am loving our friendship. I have no idea if she and Jessica are right and it’ll “just take time,” I kind of doubt it, but we’ll see. But I’ve gained a friend. Which isn’t easy to do at my age.
So, as I’ve talked about leading up to this blog entry, I’ve realized that I am a pure cuckold, and feel very comfortable in that role. And I am a loyal husband in a female led relationship-p. Jessica believes I have become less submissive as I’ve grown into this relationship. And maybe she’s right. She usually almost always is. I think in some aspects I’m not the sub I used to be, but yet still very submissive in other ears. but female led relationships doesn’t necessarily mean I need to be deep in this sub space all the time. It’s about putting her needs above my own, and supporting her life and her lifestyle. So I am a bisexual, submissive-ish cuckold in a wife led marriage. It’s taken me a LONG time to get to this point. But I feel like I really am in that safe place to land spoken about earlier in this blog. It’s a very good feeling. 2019 ended with a lot of uncertainty and turmoil for me. When I through my badge across the table and said “I quit:, I had no fucking idea where I was going to land. I was hurting. I was lost. It was a giant leap of faith in myself, A leap that turned out to be desperately needed. It spurred a career change that put my wife’s mind at ease. Made out life easier. A career I realized I actually like. But in that leap, and through that couples retreat, it did get me to take some chances and start discovering who I am. It took 365-ish days. But I’m in a good place now. And I am confident even better things will come next year.