Picking up where we left off . . .
Jen: So Kayla, speaking of semen… you did sort of mention semen…. let’s end this with questions about sex. What do you think about your sex life?
Kayla: It’s great, it’s plentiful, it’s great, it’s adventurous, it’s great, it’s fun, it’s great. Did I say that it was great? I enjoy sex. I enjoy being sexual, and I enjoy that Mike enjoys all of that from me. I am eager to please him in all ways, and sex is just one more way.
Jen: How adventurous were you before our relationship? Tell us something about your first time and any other notable experiences before we so thoroughly corrupted you.
Kayla: Maybe I was the one that thoroughly corrupted you?
Kayla: Let’s see. My first girl experience wasn’t much. I kissed a girl when I was a freshman in high school. She was a senior. We kissed and rubbed each other over our clothing, but it didn’t go any further. We did it a couple of times but then she got scared and said she wanted to stop.
I was fine with that. I had my reservations and wasn’t bummed out by her wanting to stop, but I would have taken things as far as she was willing. I didn’t think of myself as bisexual or gay. I loved guys. It was more like I was experimenting with a friend. But the thoughts of sex with another girl didn’t turn me off, but it didn’t turn me on like guys did.
My earliest sexual experience – outside of touching myself or the “towel“ fun I previously mentioned – was when I was in middle school. Seventh grade. That would make me 12 or maybe I had turned 13. How much detail do you want? I could probably give you enough for an entire post. I’ll cut to the chase. It was in a treehouse with an older boy. A freshman in high school, so like 15. Really big stuff for someone in seventh grade. Anyway, the short of it is that I got naked for him and let him touch, I then got dressed and he got naked for me and let me touch. My first handjob. And he came! Success! Ha.
We never got together after that. Funny aside but he later came out as gay. So I guess I was so bad I turned him gay? And also, since we didn’t mess around after that one incident, maybe it counts as my first one night stand (laughing).
Jen? Your first one-nighter? So there were more?
Kayla: Uh… no actually. Oh, wait, one. Yeah, and that one I don’t even remember his name. I was about 19 or 20 and it was at a party. And that was a for-real one-nighter. Live and learn.
Jen: And your first time having sex?
Kayla: I was 16. He was 19. I met him at a church retreat, but my first time didn’t leave me screaming, “Oh, God!” (laughing).
The retreat was in the woods and there were a bunch of cabins. He was one of the “counselors” and, me being me, I befriended the older crowd who were all the counselors. I was attracted to him and the short story is that he led me off to some unused cabins far from the main area and we had sex. He brought a condom, so in hindsight, he was totally prepared. I knew as we were walking there that we were going to mess around, but I didn’t think we would have sex.
Jen: Why do you think you weren’t thinking of sex?
Kayla: Inexperienced I guess. But it wasn’t like I thought we weren’t going to have sex. I just didn’t evaluate the situation one way or the other. It was like, “Yea, this ‘man’ wants to fool around with me.”
I had boyfriends and had kissed and touched and been touched before. But it was always up to the guy regarding how far things went. I was always pretty passive. I wanted to please and was too afraid to make a move they didn’t want. I figured if they wanted it, they would, well, it sounds bad, but, just take it. Not in a rough way, but just, well, initiate it. Maybe that’s a better word. Initiate it. Yes, much better. Initiate, not take. I have never felt someone “took” something sexually from me. I’ve been fortunate that I have always been in a position to freely give, but they had to initiate.
Jen: Going back to that experience in the treehouse, did he initiate it?
Kayla: Oh, he did, for sure. But I was for sure cool with it. I wanted to please, even then. And he sort of jokingly said something like, “I’ll show you mine if you show me yours.” That’s all it took. I was like, “Okay.” He said, “You first.” I took my shirt off. Very compliant. In hindsight I could have just snickered and said, “You wish” and that would have been the end of it. But I am glad I didn’t. I don’t regret the experience.
Jen: What was that first time in the cabin like?
Kayla: The guy was nice. He wasn’t aggressive but didn’t have to be. I didn’t resist anything, but he was clearly the initiator. He totally pulled my pants and panties off, and after some foreplay, he pulled his pants down and well, did the deed. My mind was not into the sexual pleasure of it. I mean, parts of it felt good but my mind wondered and focused on the parts that were a bit uncomfortable or mundane.
I was feeling some new sensations in my vagina and some nice swirls in my belly, but what I remember thinking of the most was the floor and the ceiling. Yep. Floor and ceiling, not fireworks and over the top passion. It was an older unused cabin. The planks that made up the floor were very rough, I kept thinking, “I am going to get a splinter!” And I remember the ceiling. I can picture it today. Old planks of wood with occasional water stains. No denying it, I was not that into the sex and it was more like he was having sex with me than I with him. He didn’t mind.
It seemed like he lasted a long time. I would think about what I was feeling down there…combination of discomfort and delight…then think about the floor that was scratching my back, then think about the ceiling – almost like looking at clouds and imagine a bunny or funny face. I was doing that with the water stains. OH, and then back to the feeling between my legs for a moment, then back to staring at the ceiling. As he got close I started to focus on his breathing. I liked that part more than anything. He let out the cutest noises that got louder and louder. I didn’t fully understand it but knew that it was a sign he was enjoying it. I liked that part more than anything. Then he came.
Jen: Did you go off to the cabins with him again after that.
Kayla: Yes. Twice more. Also, it became the first time I gave and received oral sex. He went down on me and afterward asked if I wanted to go down on him. Again, that’s all I needed. I was totally compliant as long as I didn’t have to initiate stuff. He asked. That was good enough for me. I mean, I wanted to, I just didn’t want to have to initiate it. I know that was the insecurity in me. I felt I didn’t deserve to ask or to presume he wanted what I wanted. I only wanted to do what he wanted to do, so all he had to do was ask.
Jen: And your initial thoughts about oral sex?
Kayla: Receiving? Loved it. I mean, really loved it. No thoughts of the floor or ceiling during that. He made me have an orgasm. And while it felt incredible for me, I remember how happy it made him. As someone who wanted to please, in my mind, I was like, “Oh, I get it. I need to orgasm to make him that happy.”
At that point, I think it was important to my psyche that my sexual pleasure was about the other person and not about me. I told myself that my orgasms were for him. In reality, believe me, they felt good to me. I enjoyed them and wanted more of them, whether with a guy or by myself. But I think at that point in my maturity I couldn’t admit that I owned my sexual desires or pleasure. Maybe it was guilt or shame? Not sure, but the way I reconciled my reluctance to accept my sexual desires was to rationalize they weren’t for me but for the person I was with. I think that’s how I started finding my joy through their joy.
Jen: And what about giving oral sex?
Kayla: As I said, he had to ask – but only had to ask once! (laughing)
I remember that pretty vividly too. If he loved my orgasm from eating me out, he took it to another level when I gave him head. And his reaction during it all was totally turning me on. I didn’t have an orgasm but I remember being very turned on after he finally came. I was as out of breath as he was and I was wanting to go again. I think if he lasted a little longer I would have cum. To this day I’ve always been orgasmic when giving head.
Jen: So did you swallow?
Kayla: Yes. I didn’t even think of it as an option. I mean, I guess I would have spit it out if it had tasted gross. It was fine and went right down. No big deal. In hindsight, he either didn’t cum a lot or it just slid right down. The swallowing seemed uneventful at the time.
Jen: What was your biggest takeaway from your cabin experience regarding your sexual evolution? Any regrets?
Kayla: Biggest take-ways from the camp were – Oral sex? Totally rocks. Penis-in-vagina? Over-hyped. But the most significant takeaway is that I actually had the ability to make someone feel that good and that someone could also take pleasure in me feeling that good. No regrets. He was a good guy to lose my virginity to.
Jen: Interesting. Even now you explain it in a way that is very focused on the other person. Your ability to make THEM feel good. THEIR finding pleasure in your feeling good. All seem like submissive thinking.
Kayla: Totally. As I said, I was very compliant. I was fortunate I generally hung around decent people. Any of the guys, from the treehouse to the cabin, to first girl-on-girl kiss, could have asked me to do anything and I would have complied. In reflection, it is easy to joke about, but no joke, I am lucky. I don’t think I was ready for anything beyond what actually took place in each of those situations. Of course, in hindsight, I think they weren’t either, which is why things happened the way they did.
Jen: What of your first time with a woman, beyond the kissing and over the clothes stuff.
Kayla: Shouldn’t I share my first threesome experience with two guys? I mean, if we are going about this chronologically?
Jen: I don’t think my readers would object. Do tell
Kayla: I was 17 and was dating a 20-year-old. I met him in high school and he went on to college. He seemed like a “man” and it was a big deal that I was dating someone in college. We were having sex pretty regularly and all was good on that front. His brother was my age and in my grade. I was talking with my boyfriend and he told me his brother was a virgin. I said something like, “maybe I could hook him up.” My boyfriend said, “You’d do that for him?” I was puzzled and was like, “Sure, why not. He’s cute, he looks like you.” My boyfriend then said, “Can I watch?” I was like, “What? Wait? Watch what?”
Then it got awkward. I had said, “Maybe I could hook him up,” which I meant to mean maybe I could find him a girlfriend. But my boyfriend thought he heard me say, “Maybe I can hook up?” which he interpreted as me saying, “Maybe I can hook up with your brother?”
Again, being the pleaser I was, and not finding the prospects the least bit objectionable, after a good laugh I told my boyfriend that if he wanted me to, I would do that. Turned out that for my first time with his brother it was just me and the brother, no one watching. But the next time it was all three of us — and no one was just just watching! Yep, I had a threesome with two brothers.
Jen: Was it a recurring thing?
Kayla: No. The threesome was just that one time. But I did have sex with the brother again. That’s another story, but the short of it is that I bet I was the last girlfriend he shared with his brother (laughing).
Jen: What of your first time with a woman
Kayla: That would be my friends I was living with right before I moved in with you. I met her in my first year of college. The short story is she wanted to surprise her boyfriend with a threesome and I said: “Count me in.” So my first time with another woman there was also a man involved, but eventually, just the two of us would get together. They asked me to move in, which I did, and well, that’s where I was when this older couple took advantage of me, brainwashed me, made me join their marriage and be their sex slave. Um, er, ah. I mean, that’s when you confided in me about your dynamic and well, here we are today.
Jen: And THAT’s the story of Kayla!
That will be the end of these interviews. But I will post a quick rundown of where things are with our “Circle of Trust” couples since I haven’t shared much about them in a long time. Oh, and of course, I still need to do a post about our Immersion 2020.
It’s so strange. Our Immersion was just a few weeks ago, but it seems like a long time ago. It was right on the cusp of our country taking COVID seriously. We were being foolish as we were doing the exact opposite of social distancing. Thankfully it was still within a limited number of friends, but still – dumb, dumb, dumb! Anyways, we survived it unscathed and uninfected. Which is the goal of any orgy! It will be nice to remember the good ol’ days of a few weeks ago.
Hope you enjoyed the 4-mega posts with Kayla!
NEXT: 346. Immersion in the Year 2020 P.C. – Swapfest
3 thoughts on “345. Kayla Part IV – Stories of first times”
I enjoyed learning more about Kayla. You and Ruck are a pretty special couple. I am very interested to know aboutKaylas first discipline from both you and Rick. I’m eager to know her thoughts and feelings before and after the sessions. Thank you for sharing your Kayla with us ❤️
What an amazing journey! And you wonder why I say that you rock? All of you do!
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