Tag Archives: first time

345. Kayla Part IV – Stories of first times

345

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?

Jen:  Touche’.

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!

 

 

 

 

 

343. Kayla Interview Part II – Kayla Ours, the new addition

343

Let’s dive right back in where I left off on the prior post.

Good thing many of you are isolated with nothing to do but read stuff like this because this is a long one.  I hope you enjoy it as much as I enjoy sharing more about my dear Kayla!

Jen:  Kayla, let’s fast forward 2016 when you became a part of us.   What were your thoughts about us before the events that led us to where we are today?

– – Kayla reminded me of a post she did on this blog.  I had forgotten.  Instead of repeating things, it turns out the answer to this question is covered in that post.  Check it out herePost 182.  Hello, my name is Kala. —

Jen:  Things moved pretty fast with us.  According to things I blogged about, it was October 2016 when I first told you about the “new” lifestyle we adopted.   About a month later, we were making plans for you to move in, which you did right after Christmas.
You went from the babysitter to a submissive in a triad with a married couple in a months time.

Kayla:  A month? That would be ridiculous, like, I was some kind of desperate and needy whore.  It was clearly six weeks!   Yeah, kinda fast.  A lot of thinking can get done in six weeks.  It really isn’t that fast.  And hey, I thought of myself as being more than just the babysitter.

Jen:  I didn’t say “just” the babysitter.  But sorry, you are right, you were much more than that.  It makes for a better narrative for my kinky readers.  But still, that was fast, wasn’t it?

Kayla:  I get it.  I know both of you thought fondly of me and I was always welcomed as part of the family, not just the babysitter.   I believe everything was just perfect timing for where I was in life, what I was needing and hoping for, and what you all were able to provide me.  I so much wanted to be a part of the two of you, beyond just a young family friend.  I had zero reservations.  Did you?

Jen:  Hey, I am the interviewer here.  I think I blogged plenty about some of the things I went through at that time.  (There’s probably about ten different posts about this beginning from Post 79. Anxiety, Resentment, Jealousy, Guilt to about Post 101 Compersion with a side of Submission and Spanking.  Probably more after that as well).

– You can read those if you want the answer to Kayla’s question. Let’s move on. –

Jen:  Speaking of a good narrative for my kinky readers, you told us before your first orgasm was to thoughts of Mike.  Please elaborate.

Kayla:   Yes, pretty sure my first real masturbation and orgasm were to thoughts of Mike.  It wasn’t thoughts of sex with him, at least not at first.   Him just hugging me, which he did in real life, as well as thoughts of him just caressing my arm, which he did NOT do in real life.  Yes, the thoughts of a sexy man caressing my arm was enough to make young Kayla all warm and tingly inside. (laughing)

Jen:  In other words, no different than what it takes to make you that way today?  (more laughing).

Kayla:  I go way beyond warm and tingly today, but yeppers, it doesn’t take much, even today.   But those pubescent fantasies in my head eventually evolved beyond him caressing my arm.  At some point I imagined him disciplining me – as in spanking me.  Not at all in a kink way but like a real disciplining from someone who might spank their kids.  After running those thoughts through my head, well, I’d get all the tingles down there.  At first,my mind would shift to just focusing on the tingles and not thinking about Mike or about being spanked.  But that eventually changed.

Jen:  Why do you think that fantasy appealed to you?

Kayla:  I don’t know.  It’s hard to explain why something makes you feel a certain way, especially at that age when you can’t even comprehend what may be behind certain feelings.  But if I were to guess, I think I wanted his attention and for him to care enough about me to want to help me.  A fantasy of him being stern with me and spanking me was how those feelings were manifested. 

Jen:  At that time, did you ever think about what those fantasies might mean?

Kayla: Don’t forget, I was like 11 or 12 when those thoughts started creeping into my fantasies.   And a twelve-year-old isn’t going to self analyze.  Heck, most adults don’t even do that.  People aren’t like you, Jen, striving to get to the bottom of every feeling.   Most people are too afraid of what they’ll find.   But at that age, it wasn’t about fear or anything.  You just sort of feel how you feel and are confused by it.  At that age I lacked the ability to try and reconcile that confusion.  It’s called puberty!

I really didn’t understand sex or have a desire for it.  I would vacillate between being scared by those fantasies and being turned on by them.  I didn’t have thoughts of penis-in-vagina sex or penis-in-anything sex.  I recall that following my spanking fantasies, my earliest thoughts regarding anything remotely related to actual penetration sex was having fantasies of him knowing I touched myself.  I can’t remember the actual details of the fantasy, but it was basically like in my mind I would tell him that I do it and he would spank me for it.  Kind of messed up.  Part pleasure, part guilt, part older man fantasy.  And I didn’t even know the term at the time, but in hindsight, part submission fantasy. 

I also remember thinking how mortified and embarrassed I would be if I actually told him I touched myself.  But I also distinctly remember being turned on by the thoughts of being so mortified and embarrassed.  In your words, I guess I was pre-wired to be turned on by making myself vulnerable.  But I never fantasized about actual PIV or even oral sex with him.

Jen:  I think having mixed feelings of guilt and pleasure regarding sex is normal at that age.  It can be so confusing.   Even for adults who attach a lot of guilt to sex.  Did you feel guilty about those fantasies?

Kayla:   No.  I never associated those feelings with guilt or of them being naughty.  Maybe it goes back to my mom’s reaction when she walked in on me after a bath as I was rubbing myself rather aggressively with a towel.  She set the tone that it wasn’t a big deal, but something that was personal and private.  I do remember feeling a bit scared about my fantasies, like, “What does this mean?”  “Am I normal?”  “Is this weird?”   But I think every kid goes through that when it comes to everything, let alone something dealing with sexual desires. 

Jen:  As you said, a lot of adults still deal with those questions, especially when it comes to kink.   Do you remember your first orgasm?  You’ve said it was about those thoughts with Mike.

Kayla: I like to think my first was over thoughts of him, but honestly I am not 100% sure.  I think I had some mini-orgasms before I had the first big “O” regarding my fantasies about Mike.  I  just didn’t recognize them as orgasms until I had a really intense one.   Are we supposed to be talking about this?  I was like 11.  Mike had to be what, in his late 30’s?

Jen:  It’s your fantasies we are talking about, so spill the beans here.  What was going on regarding those mini-orgasms.”  Set the scene!  My readers like filth.  And the details of this will be news to me and well, I like filth too!

Kayla:  Okay.  My first sexual experiences may not qualify as sexual experiences.  I mean, can you have a sexual experience without knowing what sex is?  Is sex defined by the area of your body that is being aroused or is it defined by intent?   Don’t you have some committee that determines these things?

Jen:  Hum… I’d have to check with the kink authorities on that.  But continue.

Kayla:  Ew.  I don’t like to think of it as sex and I definitely don’t like to think of it as kink.  My earliest memories of anything we would call remotely sexual was when I was like eight-years-old for god’s sake!

Jen:  Okay, okay.  I’ll rephrase.  What was your first experience where today, you recognize it as something that felt good in a way that today you would equate to a sexual feeling?   Better?

Kayla:   Uh, that’s not much better, because there is nothing at eight years old that felt like what sex feels like today.  But I will quit arguing the point and answer your question.  I vividly remember it because it is actually one of the few mother/daughter memories I have where her actions may have had a positive influence on me.   It was the incident with the towel that I mentioned a few questions ago.

I remember drying myself off with a towel and liking the feeling when I dried between my legs.  I probably was even younger than eight but it was never more than just a passing thought of, “Oh, that felt pretty good” and I’d move on to dry the rest of my body.   But at some point, maybe when I was eight, definitely no more than nine, instead of just a quick wipe with the towel and fleeting thought of, “that was nice,” I decided, “Hum, I should give that another wipe.”   A few baths later and it became many wipes and eventually full on rubs.   Over time I spent more and more time drying between my legs than I did the time before.  Eventually, I would put the towel between my legs with one hand in front of me and one behind and sort of ride the towel like a horse.  A horse that moved rapidly back and forth under me, haha.  It became a bath-time ritual.

I didn’t equate what I was doing to anything sexual.  It just felt good, really good.  It’s like, you know how the warm sun can feel good on your face when you walk outside?  That’s not a sexual feeling, it’s just a good feeling.   It was like that, except it wasn’t my face that got warm.  Ew, did I just say that?   Anyway, I had no clue what sex was and didn’t equate it to anything other than just a good feeling.   And when I did it, I would just reach some point where I was like, “Okay, I’ll stop now.” Time to finish drying or getting ready for bed or whatever.  Never another thought about it.   

Then one day my mom walked in on me, humping away at this towel that was buzzing back and forth between my legs. 

Jen:  How did I never hear this story before?

Kayla:   It’s to your credit that you never asked me about my sexual experiences in second grade!  What kind of perv would that make you!    (laughing)   But for real, I thought I told you about this.  I guess not.

Jen: So how did your mom react and how did you react?

Kayla:  I was cool.  I was like, “Oh, hi mom.”  I didn’t even know enough to think what I was doing was a big deal.  I don’t think I even stopped.  Maybe I slowed down a bit.   And the fact I don’t clearly remember much about her reaction sums up her reaction.  She didn’t have much of one.  She just calmly said, “If you’re going to play between your legs its best done in private, so lock the door when you do that.”

And two things stuck with me.  For a long time, I thought “play between your legs” was an actual phrase meaning to rub or touch yourself down there.  And in my mind, it was just play.  I didn’t know it could be sexual, because I didn’t even know that term.  More importantly, my mom’s reaction was such that it did not equate what I was doing with something should evoke shame or embarrassment.

But I guess as a kid you still sort of pick up on certain things.  While I felt it was normal enough to keep doing it and not feel guilty about it, I not only now knew from my mom that it was supposed to be a private thing that I did behind locked doors, but somehow I also knew it wasn’t something you talked about.  Fortunately, I didn’t go around to my friends and ask them if they also played between their legs.  I was already a bit of the weird kid anyway.  That would have been disastrous.

Jen:  So did you do it more often after that?

Kayla:  Eew, no.  I am telling you, it wasn’t a sex thing!  It was just a way to feel extra good after a bath.

Jen:  But you certainly didn’t stop doing it?

Kayla:  Hell no. 

Jen:  So let’s switch gears.  You said you were a weird kid.  In what way?

Kayla:  There’s the 10-year old Kayla answer and the current Kayla answer.  Which perspective do you want?

Jen:  Too much to ask for both?  Let’s start with kid-Kayla.

Kayla:  Kid Kayla thought everyone else was weird.  Well, I mean, I knew I was the oddball, but I felt I was odd because my supposed cohorts were weird.  I didn’t like kids my age.  I think it goes back to me wanting to be as small as possible so as not to upset my parents.  Be that perfect kid, be mature, be thoughtful.   Not that 14-year-olds are any of those things, but at age 10 I modeled myself after what I thought a 14-year-old should be.  I befriended older kids and they seemed to accept me.  Probably because in my mind they were the “better” kids in terms of the “right way” to be.  I admired them, looked up to them, emulated them.   That made it easy for me to be their friend because they liked how I treated them.  

As I got older, my friends always stayed older.  As a freshman in high school, my friends were seniors.  And the following year when many of them went off to college, their new college friends became my friends and so when I was 16 I had friends who were 20 to 23.

Jen:  Okay, what does the current Kayla think about why Kid Kayla was like that?

Kayla:  Honestly, it wasn’t until the last year or so I’ve figured that out, thanks in large part to you.  It was a self-esteem thing.  I was never truthful with my feelings as a kid.  The truth was too frightening.  A mom who cared more about drinking than about me.  More about making our lives miserable than about me.  A dad who may have tried his best, but couldn’t compensate for all that was missing for me.  I was fortunate that the way I reconciled this turned out to be somewhat productive.  Instead of acting out and being a wild child, I worked harder to be what I thought was the best child. 

At that moment I felt like I had high self-esteem.  I just “knew” I was a good kid, even though it wasn’t enough to bring about change in my mom.  But I know now that our self-esteem depends on how truthful we are with ourselves.  Because I was avoiding my true feelings and pretending that what I was doing was actually making a difference.  Not just pretending my actions helped my parents, but pretending my actions were helping me.  I was pretending I wasn’t being emotionally neglected.  And all the things I was doing to cope with that was not really addressing that.  When we aren’t truthful with ourselves, our self-esteem goes down.

I now know that is what led me to turn to alcohol as well.  You could say it was genetics, and maybe that played a part, but for me, I think it was the environment.  I didn’t feel good about myself because I didn’t know myself, I never faced my emotions.  As I felt those emotions coming to the surface I had to work harder to drive them down, and drinking helped do that for me.   Fortunately, I had you all to stop that from ever reaching a critical point.   

And that is why, as a child, I loved being around you guys.  I felt loved, I felt respected, I felt valued.  Not just from the two of you but from all three of the kids.  It was such a warm and nurturing environment.

Jen:  Thank you for saying that.  At the time, we knew things weren’t good for you on the home front.  We didn’t know all the details, but knew we were your respite.  And it wasn’t like you were just a charity case.  We truly loved having you around.  You were so good with J and T1 and T2 enjoyed your company.

Let’s fast forward to the day I shared with you that me and Mike adopted Domestic Discipline.   It really seemed to connect and resonate with you.  Things happened so fast from that day forward.  Why was that?

Kayla:  Well, first, maybe it helps to understand I already knew I was bisexual.  I had been with other girls, and at the time was living with a friend of mine and her husband and we would have threesomes.   While I was basically a “friend with benefits” to them, I found I liked the idea of being part of three.  I don’t know why.  Two friends are just better than one, right?  And then, of course, there’s the sex.   But it was more than that.  I just really liked being part of three.  However, I was not really that close to them.  I was definitely not in love with them.   Deeply in-like?  Is that a thing?

Jen:  It is now

Kayla:  So I was already predisposed to love the idea of being in a thruple.  Then you add in the fact that by far the two of you are my favorite couple.  Like, “favorite” didn’t even come close to describing it.  I idolized your relationship.  So the thought of being any part of it as an adult, not just a babysitter or kid?  Count me in!

And I was feeling a lack of control at the time.  I wanted to still be the perfect daughter but was drinking more and more myself, and I would feel guilty about that.  It was this loop of working hard to be perfect to cover up my feelings of being neglected, drinking to cope with my true feelings, feeling guilty about drinking, thus, once sober, working even harder to cover up my feelings.  And the loops got bigger and bigger.  I wanted off that roller coaster.  

And I was just getting ready to finish up my undergrad and was facing a decision to get a job, go to grad school, or move back home.  I didn’t feel prepared to make that decision, mainly because of my drinking.  I was feeling very anxious about that.  Everything about the two of you just felt right.  It felt safe, it felt sane.  I was attracted to the two of you, you to me, and it all just felt so right.  I really was in awe and so excited.

Jen:  Beyond the more meaningful relationship with us, what were your thoughts about DD?

Kayla:  It also resonated with me.   Perhaps because of my earlier fantasies, but also because I had always been so self-disciplined for all the wrong reasons, I loved the idea of striving to be self-disciplined as a way to serve someone else.  It’s like I had this power of self-discipline and could finally use it for good, and in return, focus that discipline on what is truly good for me.  I just knew the two of you had my best interests at heart. 

Jen:  Thank you.  We did, and we still do.

There’s so much more we could cover.  And I received a few emails with questions specifically for Kayla.  Some were practical things like how finances work, others about where she sees herself in 5 years, 10 years and beyond.   And then a few sex-related questions.   So — we will just have to do a Part III!

WONDERFUL NEWS
And the answer to some of those questions are revealed in some wonderful news that Kayla shared with us.  Should I wait for Part III to share it here?

Yes, I should. 

 

But, I won’t.

There will soon be a new addition to our family!

How long should I let that sentence linger?

A little longer?

Longer still?

Okay, long enough.

No, it’s not what you think.  Hum.  I really should save this for another post.

 

Okay, okay.  I will say it here.

The new addition isn’t really new, just new in name.

Kayla asked us, and we agreed, if she could legally change her last name to ours. 

Her name will soon officially be, Kayla Ours!   

Just kidding.  You know what I mean.  Her last name will be our last name.   It was something she thought of and very much wanted.  I will elaborate more on that in the next post.

What, you thought maybe the news was something different?

Next: 344. Kayla Interview Part III

225. Pansexual, a skinny dip, and my “first time.”

225

I’ve shared a couple of stories of my youth — Post 64. Strip Quarters and Post 73. Pube Shaving Party.  Since I’ve brought up naturism, in my last two posts, now seems like a good time to share one more story of my youth.  Before I do . . . 

NUDIST VS NATURIST
I learned from E, the preferred term is “naturist” not “nudist.”  To some, nudity connotes sex, whereas naturist connotes nature.  “Naturist” was coined about 125 years ago by those who partook in the nude lifestyle.  “Nudist” was a term created about 90 years ago by media.  Focusing on nudity gave it a more prurient connotation, at a minimum to sensationalize it, at worst to vilify it.  The words are often used interchangeably now, but E is sensitive to the differences in what they mean to her, so, I too will use the word naturist.   

Naturism can go deeper than simply rejecting clothes.  It can encompass how we embrace nature.  E said her parents have a minimalist lifestyle, concerned about keeping a “reasonably small carbon footprint.”  They don’t shun electricity or modern advancements – they own a car and have all the modern conveniences.  They keep their possessions to a minimum and focus on conservation and recycling.   

We haven’t met them yet as they live in another state.  It is possible we may meet them at the naturist resort we are looking into.  It will be an interesting introduction for us, to say the least.

YOUNG JENNY GOES SKINNY DIPPING
In my prior post I shared my fondness of being naked.  That fondness plays a role in my first orgasmic sexual experience (not counting masturbation).  I think I mentioned before, but if not, I had sex with a girl before I had sex with a boy.  By the time I had sex with a boy I was a very experienced virgin – but that will have to be another story.

The sex would have happened without the skinny dipping, but I wanted to share the full story to illustrate my penchant for baring it all, even when I was younger.  

It was the summer between 8th and 9th grade.  I was 13, Amy was 14.  She is just two weeks shy of being a full year older than me.  With my birthday being just before the cut off to start school, and her age is just after the cut off, we were in the same grade despite an almost one year age difference.  I was often the youngest in my class, she the oldest.  Not a big deal, but it can be at that age, especially when it comes to physical maturity.  Adding to her 11 month head start, she was an early bloomer, I was a late one.  Yeah, she had boobies way before me.   

Amy’s parents had a really nice house with a large pool in their backyard.  The backyard was secluded, at the top of a steep hill with no houses behind it.  The two houses on either side were offset such that they didn’t have much of a view of the pool, and any potential view was obscured by many trees.  They had a gravel driveway, which, while out of view, was actually close to the pool and made enough noise that you could always hear any car driving up.  The perfect storm for clandestine teenage activities. 

We had seen each other naked countless times throughout childhood.  Amy was well aware of, and subject to, my proclivity to be in the buff.  I would often swim naked when her parents and brother weren’t home and even stay naked after the swim.  For years she refused to doff her swimsuit.  One day she finally relented.

From then on it became routine for us to swim naked if her parents were at work and her older brother wasn’t home.  It was comical because each time we heard a noise she would scurry to put her suit on.  Well, it wasn’t long until her brother caught us.  He was with a friend who parked at the curb and walked up to the house, thus we didn’t hear them.

He was 18 and had just graduated high school.  He was a “man” in my mind, plus was Amy’s dorky older brother.  No one was interested or thinking anything about sex (at least I wasn’t and I don’t think he was).  I wasn’t embarrassed, but Amy surely was and was yelling, “Don’t tell mom and dad, don’t tell mom and dad!” I calmly walked over, naked as can be, and talked to him and his friend.  I bargained with him not to tell.

He said no to my offer for him and his friend to simply join us in our “clothing optional” swim (much to the chagrin of his friend).  But, it didn’t take any convincing to get him to accept the offer of feeling free to watch me that day or any other day.  That, plus, he had to agree to not tell anyone else or invite any other of his friends over.

I was happy because it meant more opportunities to be naked as we didn’t have to worry about her brother being home.  By the way, in retrospect the thought of this horrifies me.  I put myself in a very vulnerable situation being naked in front of two 18-19 year old guys.  Even though I had every reason to trust Amy’s brother, I didn’t even know his friend.  In hindsight I was foolish and very fortunate that they both ended up being deserving of that trust.

At first Amy decided swimming naked in front of her brother was too much for her, so she kept her suit on.  Once again, eventually she said, “What the hell,” and went naked.  At first we got a lot of attention, her brother and/or his friend  would hang out by the pool and watch.  But eventually they tired of it other than an occasional peek out the window.  

MY FIRST “REAL” SEXUAL EXPERIENCE
If you’re keeping score, both Amy and I had boyfriends in 8th grade that we allowed to feel us up.  She had even let her boyfriend suck on her breasts — I was the prude who hadn’t gone that far.  Ha!   Beyond that, there was some rubbing of privates over the pants, but neither of us had “touched dick” nor been fingered (other than by our self via masturbation).  And we had both experienced orgasms, but again, only through masturbation.  Okay, back to the story. . .

After one of our swims, Amy and I were in her bathroom drying our hair.  We had bottoms on but no tops.  We were talking about things we often talked about – such as boys!  The conversation turned to another common topic of ours – our breasts.  More precisely, her abundance and my lack of.  This was a normal conversation for us to have.  It was not sexual.  We always openly talked with each other about our bodies, even about masturbation.

At some point I asked her if I could feel her boobs.  I was just curious.  I had actually done this once before, about a year or two earlier, but they were much bigger now.  She said yes, so away I went.  Unlike before, this time I really went!  She stood in front of me as I played with one, then the other, then both at the same time.  Squeezing, poking, prodding, and pressing and pulling her nipples between my fingers. 

I don’t know how long I did it for, but it surpassed the length of time to qualify as platonic.   While my eyes were focused on her breasts, I became aware of her breathing as her chest would slowly expand and contract, and the sounds of inhaling and exhaling grew louder.  I finally looked up at her.  Her eyes were closed, lips were pursed.  I clearly excited something inside her.  

I smiled.  Even though it was not my intent, I knew she was feeling something sexual.  I kept playing with her breasts until her eyes opened.  When she saw me looking into her eyes she quickly got embarrassed and said, “Okay, enough of playing with my boobs, let’s get dressed.”  I could tell she was uncomfortable so I didn’t say anything about it.  That was that.

The next day we were hanging out in her room and Amy says, “Hey, it’s not fair you got to feel me up.  I want to feel you up now.”   I took it as her just teasing me and said, “I did NOT feel you up, I was just curious to know what they felt like.”  She continued teasing and said “yes you did, yes you did.”  I finally said “Fine, then if it will shut you up, then go ahead, feel me too.”  She did.

She also felt and felt and felt.  Needless to say, she also excited something in me.  I started to feel her up too.  We played with each other’s breasts for quite a while.  I actually don’t remember who went first, but at some point we began sucking on each others breasts.  And that was that.

That night I remember masturbating to thoughts of Amy.  The first time I ever had such thoughts.  I didn’t feel bad for thinking this way.  It was the early 80’s, I didn’t know anyone who was gay or bisexual, or even really know much about the terms.  I didn’t even connect my feelings with any of those terms.  It wasn’t about feeling “that way” about girls.  It was simply feeling that way about my friend Amy. 

The next day, at Amy’s, we stayed in her room the entire time.  We got naked, kissed for the first time, fondled, and fingered until each of us had an orgasm.  This was the first time that, other than through masturbation, we had been brought to climax.  We went on to frequently have sex, eventually advancing to oral sex as well.  And that was that.

PANSEXUAL
Amy and I continued having sex throughout high school and college.   All along it was important to me to make the distinction in my mind that I wasn’t attracted to girls, I was just attracted to Amy.

Only recently has it dawned on me that such a distinction is stupid.  Why did I feel it was so important to make this distinction?  I mean, I didn’t like every guy I saw, but I never felt compelled to make the distinction that any attraction to a guy was about the person versus the gender.  That was just too obvious!  So why then was it so important for me to make that distinction about Amy?

I think that it is simply due to the negative baggage society puts on us when we are attracted to the same sex.  As if you are attracted to one person of the same sex you must be a sexual deviant that wants to have sex with every person of the same sex  – thus, my distinction was important to me.  This is, of course, just societal bull shit.  

As I eventually came to understand, my sexual attractions, men or women, are based on the person, not the gender.  And it is fortunate we now have a name for this – pansexual.  No negative connotations, no negative societal bull shit baggage.  We didn’t have that term back in the early 80’s.  Pansexual!   That’s me!

Next: Post 226. Kink Research

62. Sexual Adventures of Pre-DD Jenny

Feel
Mike gave me the suggestion (or is that an order?) to write about my sexual experiences in my younger daze, um, I mean days.   I might as well start from the beginning, way back to my virgin days.   Yes, hard to imagine, but I was once a virgin.

I joke that by the time I had sex with a guy (at age 17) I was a very experienced virgin.  By the time the “magic moment” arrived I was well versed in mutual manual and oral stimulation – both with guys and yes, with girls (actually, girl, as in singular).   My first sexual experience was in 1984, before it was an in-thing to be bisexual / lesbian.  Not to say it is always accepted today, but it was not talked about back then and definitely not something you wanted people to know about.

I’ve know my best friend for life, Amy, since kindergarten.  She lived just a few blocks away and we were extremely close.  So fast forward to when we were 15.  We had seen each other naked countless times so it wasn’t even a thing.  Amy had a swimming pool in her backyard and it was pretty secluded, so one of us, not sure which, got the idea to skinny dip.  We would get freaked out every time we heard a noise that sounded like a car pulling up or a car door closing.  We would run and grab our suits and then laugh when no one was there, then get naked again.

One day we were finished with a swim and we were in her bathroom drying our hair.  We both had shorts on but no tops.  I commented about her breasts, which I’ve done before, regarding her abundance and my lack thereof (she developed quite early and rapidly).   She made some comment about me being obsessed with her tits because I always stared at them and talked about them.  Guilty as charged!  I said something about them looking so squeezable or something like that and she said something like, “Well, give them a squeeze and see.”   It wasn’t a sexual thing, it was just playful and innocent, or at least seemed that way.   Well, apparently I groped her for several minutes in a trance like state.  We were real quiet while I squeezed and gave her a major feel up.  Her nipples got big and when she noticed it she broke the trance by covering her tits with her arms and moving my hand away and saying “enough!”  We then both just laughed and I said something like, “Yep, they are squeezable.”  That was that.  Nothing more to it.

It wasn’t much longer after that day that Amy and I were talking about masturbation.  That was a common topic for us as we would tell each other about our favorite things to hump and pretend.  She told me that ever since I “felt her up” (as she referred to it), she realized how good it felt to play her nipples.  I was quasi-offended at her statement that I “felt her up” and part-joking/part-serious said that “I did not feel you up! I was just curious!”  Amy then said something like, “Well, I am curious too.  Can I feel yours?”   So, I let her.  It wasn’t long before we both had our hands in each other’s shirt.  This curiosity turned sexual.

Without going into all the details, the curiosity that we satisfied that day with a mutual grope session turned into greater curiosity and greater satisfaction on subsequent days and weeks.  While we took it slow, it eventually led to us exploring many facets of lesbian sex.  Neither of us felt bad about it.  We both liked boys (a lot) and both felt like we weren’t “having sex with another girl.”  We were just having sex with each other.  It was nice that we never attached anything negative to what we did.  I think that healthy beginning, added to my zero sense of shame, set the stage for a positive outlook on all things sex and my sexuality.

I’ve got a lot of Amy sex stories, not all involving just her and I messing around.  We also roomed together in college.  I could fill several posts with our many adventures. Perhaps another time, and I’ll stick to the stories that occurred at age 18+.   It’s kinda’ creepy thinking about who might be getting aroused by stories of my early pubescent romps (yes, I am talking to you, you sick f*ck!).   Just kidding.

A word from Mike:   Hello all, not sure what to add, but Jen asked that I occasionally share my reaction to a post.  Not much for me to react to as these stories are old news to me.  Jen had confided in me about her and Amy back when we were in high school, and the story of their initial fun together is tame compared to other stories.  We have nicknames for some of those stories such as “Strip Quarters,” “Night Swimming,” “Pube Shaving Party,” and “Reunion.”  I’ll let Jen reveal those in time.   I’ve never known Jen to be shy in the bedroom, but even after all these years and 25 years of marriage, the last year and half have definitely taken things to an entirely new level of exploring.   I am a lucky guy.

Next:  63. Ice, Ice, Baby Redux – A Solution!