Well, dammit

The nerd came back over last night.  Due to both of us being supremely busy this past week, this was only the second time we’ve been able to play.

Still, it was fun.  I pushed his limits a little further than last time.  I started out by tying him spread-eagle to the bed and fingering his ass a little bit.  He was still super enthusiastic about anything having to do with anal, and that was totally fine by me.

I tied him down on his back, and made him look me in the eye as I fingered him.  He’s still practically a virgin, so he was unbelievably tight, and it didn’t take much to elicit a sexy reaction from him.  Within minutes, he was panting and gasping, and I was loving every minute of it.  It’s still such a novel thing for me, for it to take so little to get him going.  What kazander and I consider a good warm-up is about all he can handle.

So after a little bit of fingering, I switched to his vibe.  He tensed and arched his back as I slid it in.  Even as slender as the thing is, it’s still a bit much for him.  So I took it slow.  Sure, I love causing pain, but I want him to enjoy anal.  There’s plenty else I can do to cause him some pain.

Once it was all the way in, I left it there, without turning it on, and found other ways to amuse myself.  The wartenberg wheel was pretty fun, especially around his groin.  When I ran it lightly over his balls or up and down his shaft, he’d gasp and hold his breath, his entire body tense and his hands balled into fists.

Freaking adorable.

I also introduced him to my flogger, using it just a bit on his inner thighs, just enough to leave a few nice red marks, and make him squirm a bit.

I always love tying a boy spread-eagle on the bed, because they just look so cute when they squirm in their bonds.  It’s hard to explain, but just the way they writhe, the way their legs bend and tense as they twist their bodies, the way their hands ball into fists, the way they try so hard to bring their limbs together, trying to protect themselves…

God, that’s the best.  And the nerd certainly didn’t disappoint.  He’s just so adorable, and so little!  I didn’t realize that he’s so much shorter than I am.  I’m not insanely tall, at 5’9″, but I’d worn heels both when I first met him, and when we played the first time, so I couldn’t accurately judge.  But this time, I was barefoot, and when he took his shoes off, and I approached him, I saw that I’m a good half a head taller than he is.

So he’s significantly shorter than I am (I’m guessing 5’5″, maybe 5’6″), he’s only 23 (a baby!), he’s unbelievably shy (so cute!) and he just has this adorable, lost-puppy type of face.  God, I just want to chain him to the foot of my bed and keep him as my pet.  Maybe even give him a butt-plug tail.

Yeah, that would be awesome….

Anyway, where was I?

Ah, spread-eagle.  Right.

So after the flogger, I turned the vibe on medium and started fucking him with it.  And the way he writhed was just freaking awesome.  He was panting and moaning and straining against the cuffs, my panties were immediately soaked.

I untied him and told him to get on all fours on the edge of the bed.  He’s not ready for my strap-on (dammit) so I had to settle for holding the vibe in place with one hand, and using the other to grab his hip as I thrust into him.

And wow, he loved that.  That was the least shy I’d ever seen him.  He went nuts, pushing back against the vibe, rocking his body back and forth so I’d fuck him even faster, mewling and moaning like he’d been fucked a hundred times before.  There was nothing shy or reserved about him.

Like, whoa.

At one point, I reached down and gripped his dick, playing with it a bit while I fucked him.  And within seconds, he’d reached the edge, and I had to stop.  He was totally, completely loving every moment of it.

But after awhile, it started to get to be too much for him, and I saw him starting to wince in pain.  I wasn’t done with his ass by a long shot, so I decided to give him a little bit of a break.  There was no reason to push him to the point where it would be too much.  Not yet, anyway.

So I went back to the flogger, letting him deal with the pain of that.  My flogger is leather, and rather thin, so it’s light and stingy, and it doesn’t take much to leave little red marks.  So I spent a few minutes testing his pain threshold, bringing him to a few more edges, and verbally humiliating him.

But there was something else I was eager to try, something he’d mentioned the day after our first play, so I tied him back down and blindfolded him.

I knew he was ticklish from our first time playing.  But he told me that having his nipples licked was actually his biggest weakness as far as being ticklish goes.

Go figure, right?  But I was definitely going to take advantage of that.  He’s not a masochist, and I wanted to bring him to the point where he’s profusely begging for mercy.

So I went to it.  Since he was blindfolded, he had no idea it was coming, and his reaction was everything I’d hoped it would be, and more.  I combined that with reaching across and tickling his sides, and that was just all kinds of awesome.  I loved it.  It’s been awhile since I’ve been able to play with an extremely ticklish sub.  It’s something I plan on taking advantage of quite often in the future.

I gave him a break, and turned my attention back to his ass.  I used another toy on him, a soft rubber one with balls that start small and gradually get bigger.  He can handle all but the biggest relatively easily.  I pushed the biggest one into him without any hesitation.

He was panting and squirming, trying his best to handle it.  I said, “Aw, what’s the matter?  Does it hurt?”

He said, “Yes.”

“A lot?”


“Would you like a distraction?”

He was about to ask me what I meant, but I started tickling him again and he lost all ability to speak.  And tickling him with the toy all the way inside him was even better.

Still tickling him, I reached over with one hand and started jerking him off.  It took literally seconds for him to reach the edge, but this time I told him to cum.

And good God, he made a mess.  Ah, the benefits of youth.

It was at this point I discovered another weakness, quite by accident.  Of course, most men are incredibly sensitive after they cum, which is awesome, and something I enjoy taking advantage of.  But he’s more sensitive than most, and when I rubbed the head of his dick, he went nuts.  It was amazing, and I spent a few minutes doing that before finally letting him relax, removing the toy and blindfold, and uncuffing him.

So all in all, it was fun.  But today, while we were texting, something rather disappointing came up.

Forced bi is a hard limit.

Well, dammit.

That’s the whole reason I started looking for a sub.  I wanted to add another boy to my marriage, and Dominate the two of them together.  My fetlife profile explicitly states that I am not even a little bit interested in straight men, or men with forced bi as a hard limit.  And in all of our conversations, he said that it was something he was willing to try.

So part of me was pissed that he changed his mind.  But I took a moment and thought about it.  He’s brand-new, after all, and really doesn’t know what he likes.  Sure, when he had absolutely zero experience, the idea of it may have been hot.  But now that he’s gotten his toes wet, he has a little bit better idea what he can and cannot tolerate.  So I expected his interests to change.  I just didn’t think it would change that quickly, and without even trying it (throughout all of our conversations, he kept saying he was willing to try anything once).

He said it’s something he’s not mentally ready for, which leads me to hope that he’ll eventually get there.   So I’ll give him a few months, and hope it happens.  If it doesn’t, I’m going to have to let him go, which I really don’t want to do.  He’s pretty much perfect in every other way, but if he can’t/won’t do forced bi, then that means I’ll have to get another sub for it, and I just can’t have three subs right now.  That’s too much.

I still have the other sub I’m looking at, zane, and am planning on playing with him sometime next weekend.  And zane has enough experience to know, without a doubt, that forced bi is absolutely doable.  So if the nerd doesn’t work out, I still have options.

I really hope the nerd works out, though.  I don’t want to have to let him go.  I think he’d be a perfect fit for what I want, and I think, once he gets over his shyness and kazander’s overall intimidating nature, he and kazander will get along pretty well.  I’m definitely keeping my fingers crossed.

9 thoughts on “Well, dammit

  1. That’s disappointing for sure. I hope it turns out to be a big case of nerves and he eases into it. He certainly sounds adorable.

    Thanks for sharing your adventures! yum

  2. polthusx says:

    So much for ‘willing to try anything once.’ Maybe he was hoping you’d forget? 😉

  3. Kitty says:

    Oh no! Hopefully it’s just down to lack of experience and social conditioning. I was looking forward to reading more about this guy because he sounds so cute!

  4. Zed says:

    One thing at a time….you sound like you are getting him to do just fine. It is just a kind of freakout, I suspect. Time will dissolve that…and trust of course. x

  5. kwswblog says:

    “The nerd” sounds like he’s super cute in all the best ways, and this was a very hot read. 🙂 Love it!

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