30 Days of Kink: Day 5

What was your first kinky sexual experience?  If you haven’t had one yet, talk about what you hope to have happen.

I guess my first truly kinky experience was near the end of my freshman year.  I was 15, and was the first-chair flutist in the varsity band.  Yes, I was a nerd.  I still am.  This should not be news to any of you.

We practiced during class, obviously, and then every day after school, from 3 to 6.  From the time school let out til the start of practice, we all hung out together and socialized.

Stay with me, here.  I have a point, I promise.

The point is that the band was very close.  We hung out together.  We ate lunch together.  If we had another class together, we’d sit together.  We were always together.

The boy I lost my virginity to was a trumpet player in the band.  And notorious for being a womanizer and a bit of a man-whore.

He was attractive, and he damn well knew it.  He was an asshole, but the kind of asshole you just chuckle and roll your eyes at, but love having around.  When I lost my virginity, it ended up being completely meaningless, and I was an idiot and thought I was in love.

*Side note:  I heard he’s gay, now.  Which would explain awholefuckinglot.*

But there was someone else, outgoing and charismatic in a completely different way.  He was a senior, as well (as was my first boyfriend…. notice a pattern, here?  My attraction to older guys started early).  He was tall, standing at 6’4″, with blond hair, startling blue eyes, and a really sweet smile.  He was attractive, like the trumpet-player, but in a different way.  A more innocent, guileless way, I think.  The trumpet player looked older than his 18 years, while he looked quite a bit younger, despite being so damn tall.

He was the nice guy.  The guy you cuddled with on those cold mornings before first period, the one you talked to and confided in, the one you felt safe with and knew you could trust.

So he was friend-zoned.  Hard.

But he and the trumpet-player were great friends, and it was through them that I met my first boyfriend, as well as the owner of the first heart I ever broke (which is something I actually still regret today.  I was a shallow little shit).

Even through my super-intense four-month relationship (gotta love that first love, right?) I was still close to the nice guy.  We flirted all year, and I truly dreaded him graduating and me having to come back the next year without him there.  I loved him just as I loved my boyfriend.

But then, I had a pregnancy scare, and my boyfriend dumped me (gasp!) and suddenly I was single.

And I’d mentioned before that I had self-image issues as a teenager.  The end of my freshman year was a bit of an eye-opener for me.  It wasn’t enough to overcome my teenage angst and insecurity, but it definitely opened my eyes.

I was devastated, of course, when I was dumped.  Not only did the break-up itself hurt, but the reason for it was another slap in the face.  He thought I was pregnant, which would fuck up his college plans, so he broke it off before I could even take the test.

Ahh, boys.

Anyway, the next day in school, I cried through pretty much every class.

But then I started to notice something.  All of my guy friends (at this point, I had way more guy friends than girl friends) were suddenly super fucking attentive and uncharacteristically compassionate, and at any given point throughout the day, I was wrapped in the arms of one of them while they comforted me.

Like, whoa.

But I was upset, hormonal, and just an idiot in general because of my age.  I didn’t think anything of it.

Until the next week.  When I still had all of these guys hanging on me, offering comfort and companionship.  And then it started getting awkward.  I still wasn’t even remotely over my first boyfriend.  And boys were just popping out of the fucking woodwork, man.

I really, really broke the heart of someone I cared about.  It was the last time I talked to him, and I still feel bad about it, 14 years later.  By the end of the second week, so many guys had asked me out, I was just disgusted with the gender in general.  I wanted nothing to do with any of them.  I was still emotional, still reeling from the break-up, and would still randomly break down crying.

So one of my friends (incidentally, one of my boyfriend’s and the nice guy’s friends, as well), who’d helped me write my very first song, who was the most talented fucking piano player I’ve ever met, even up to this point, who was sweet and kind and caring, approached me one day and asked if I wanted to watch a movie with him after school.

And I blew up on him.  Everything I’d been feeling, everything I’d been trying to control, just exploded.  I took a sick, perverse satisfaction in the way his face changed as I yelled at him, publicly humiliating him, saying every hurtful thing I could think of to him.  A dark thrill ran through me when I saw the color rise in his neck and face, and I saw his eyes start to water.

I stormed away, and he never spoke to me again.

But through all of this, the nice guy kept a distance.  He wasn’t one of the dozens that asked me out, or offered to hold me, or anything like that.  At first, I thought it was because of his friendship and loyalty to my ex.

I didn’t think much of it, and ended up dating someone else a week later, and life went on.

Then, a month before the end of school, I broke up with my next boyfriend and found myself single again.  And I found myself sitting on this little half-wall outside the band room, leaning against one of the columns, reading, alone, when Nice Guy walked up.  He asked if our teacher was inside, and I told him no, but that was all the interaction I was expecting.  We were still friendly, but hadn’t really spoken since the break-up.

So it surprised me when he stood next to me, leaning against the column, and asked what I was reading.  He hadn’t been that close to me in a long time.

We started talking, and at one point, he put his hand on my shoulder in what was supposed to be a casual, friendly move.  But his fingers lingered just a bit too long, and that was all I needed.

There was this staircase outside the band room that led to a storage area above the room.  An awning stuck out in front of it so you couldn’t see the landing at the top of the staircase until you were almost standing directly underneath it.

We went up there and started making out.  And I’m not exactly sure how it happened (this was 14 years ago, y’all) but somehow all 6’4″ of him was lying on his back on the landing, and I was kneeling beside him, pinning his wrists above his head with one hand, while pulling his shorts down with the other.  I kissed him, then reached down and gripped his cock hard enough to make him gasp and whimper into my mouth.

And I was instantly wet.  That was the first time I’d really experienced what pain does to sweet little boys, and I was hooked.  I kept hurting him until he started struggling, trying to pull his arms down, but I immediately let go of his dick and put all of my weight on his wrists, telling him to stay.

He was leaking precum, so I put some on my finger and fed it to him.  He was reluctant as hell, but didn’t protest.  For a moment, I kept my finger in his mouth, pushing it further and further in, sliding it across his tongue, getting it wet.  I remember my heart pounding.  I knew what I wanted to do, what I was going to do, but I didn’t know how he’d react, or how I’d handle his reaction.  I didn’t know what BDSM was, or what the hell I was doing.  I just knew what I wanted, and I knew him well enough to know I’d be able to get from him.

Once my finger was wet, I reached back between his legs, further down than he was expecting.  That’s about the point that he started struggling again, telling me to wait, wait.  But I kissed him, effectively shutting him up as I slid the tip of my finger inside him.

The feeling of my finger in him made him start struggling in earnest, and he relatively easily got an arm free and grabbed my wrist, telling me to wait.  But I just smiled down at him, kissed him again, and said, “No.”

He was still holding my wrist as I slid my finger all the way into him.  It was my first time penetrating a boy, and I was immediately addicted.

Once it was all the way in, I knew he wouldn’t struggle anymore, and let his other hand go.  I started jerking him off, slowly fingering him as I did so.  He came pretty quickly.

I let him up, let him clean himself up.  We hugged and kissed again before walking back down the stairs.  We didn’t really talk about it, didn’t bring it up after that, and never got the chance to do it again before he graduated.  Although, about five years later, I ran into him again by chance.  He was the branch manager of a bank, and we immediately exchanged numbers and set up a date.

In the end, he and I weren’t compatible, but it’s still something I remember fondly.

New Rule

So I’m still freaking bummed about the nerd.

Like, seriously bummed.

Zane is still very promising, and I’m looking forward to seeing how that pans out.  As of now, he’s the only one of the original three that is still a viable option.  I haven’t been able to play with him since last Saturday, and he’s going out of town next week (he travels for work) so it looks like next weekend is the earliest I’ll be able to see him.

In the meantime, I actually have two other options (both considerably younger than I am… what’s with all these adorable little babies running around lately?).

One of them may pan out, but it’s doubtful.  It looks like he’s more of a weekend-type player than a 24/7 sub.  So I don’t have high expectations of him.

The other, I’m cautiously optimistic about.  He’s twenty years old (twenty years old!) and a virgin.

Not an anal virgin.  A virgin virgin.  Like, an actual virgin.s5AQTIk

Yeah, I could work with that.

And based on the very little I know of him at this point, he seems like someone I could get along with outside the bedroom, which is super important to me.

He’s a preschool teacher (and I have a preschooler that I never shut up about) so there’s that.  From the way he describes himself on his profile, he’s a big guy, so it’s less likely that kazander’s size will intimidate him, the way it did with the petite nerd.  I’ve always had a thing for taller guys, anyway.  Being shorter than I am doesn’t disqualify anyone (zane is a tad shorter than I am, and he’s the one I’m most hopeful about), but those tall guys just catch my attention.  He seems very eager to please and will go out of his way to be of service.  He read my blog post bitching about the lack of Queen of Diamonds stuff, so he went and searched for some things, even messaging someone on Etsy to ask if they could make something for a Queen of Diamonds.  I thought that was very sweet of him.

But again, there’s the inexperience thing that I’m a bit worried about.  I told him about the nerd and my heartbreak there, and made it very clear to him that I am not the least bit interested in him if forced bi becomes a limit.  He assures me that he can handle it, so I’m cautiously optimistic.

And to prevent the thing with the nerd from happening again, I’ve created a new rule.  On the very first play session, there must be two types of interaction with kazander.  First of all, they must interact on a social level.  That means before I take the new boy back to the bedroom, we must all sit and chat for a few minutes.  I understand that it’ll probably be quite awkward, so I’m not expecting a four-hour conversation, but there’s got to be something.

Secondly, there must be a level of sexual interaction between the two of them.  On the first day.

I’m not going to get emotionally invested with someone, only to find out a month later that I’ve wasted my time and have to give up my toy.  Again.

Originally, I was planning on making the new boy give kazander a blowjob, even if only for a few minutes.  But then, after talking to kazander, I figured I’d probably have to amend that a bit.

I keep forgetting that kazander is still a tad reluctant to do the whole forced-bi thing.  He’s a bit nervous about it, so I have to take that into consideration.  And he empathizes with the idea of a completely inexperienced sub being made to give him head.  He said it’s like throwing a kid into the deep end of the pool before figuring out if the kid can swim.  And I get that.

So I changed it a bit.

There will be some sexual contact, without question, because I’m not willing to repeat the mistake I made with the nerd.  The minimum is a handjob.  Depending on how things go, depending on how kazander and the other boy are doing, and depending on my mood, that may change.  They may even fuck, I don’t know.  We’ll see.

So I’m looking forward to see if he works out.  I’m hoping I can meet him soon.