A different approach

This past weekend, the spawn was staying with family, so Kazander and I had the house to ourselves.  Which is a rare enough occurrence that we wanted to take advantage of it.

I spent a big chunk of the morning and early afternoon teasing him and doing some light play, but the interesting thing happened when we decided to take a shower together.

I’d planned to make him cum in the shower, but when he got close, he fell into one of his old habits.  He moved away and said, “Wait, I don’t want to cum yet.”

It’s something that never fails to annoy me, and I usually launch into the same, tired reminder that he doesn’t get to make that decision, he doesn’t get to dictate to me when he cums, and he should be grateful I was in a nice enough mood to allow it in the first place.

We have gone round and round and round with this.  Depending on my mood and the day I’ve had, it’s gotten to the point now where it’s enough to quash my libido and make me completely uninterested in touching him for the rest of the day.

So that spike of annoyance ran through me, and I opened my mouth to voice my frustration.

But then, I had a different idea.

“Alright,” I said.  “Well come here, I want to edge you again.”

I made him bathe me in the shower, then I bent him over and fingered him while edging him two more times.

We got out of the shower and got dressed.  I made him edge again just before we had to go over and spend some time with the family next door.

About half an hour into the visit, I pulled out my phone and texted him.

“Go home and edge again.”

After dinner, we went back home and binge-watched a TV show together.  And at the end of every episode, he had to edge twice.

I think it was around Edge #12 or so that he figured out what I was doing.

“I should’ve just kept my mouth shut,” he groaned as he squirmed on the couch after yet another edge, his cock throbbing.

“Oh?” I asked.  “Did that end up being a bad idea?”

“A little bit.”

“I’m glad you think so.  Edge again.”

He sighed, there was just the slightest hesitation, and then he reluctantly reached down to bring himself to an edge again.

Another five or so edges later, he was frantic and desperate, the begging almost constant.  He kept trying to bribe me to let him cum, and he got a fantastic refresher course on just how relentless I can be.

Another five or so edges later, he couldn’t stop writhing even between edges, absently humping the couch, needing constant reminders not to touch himself.  At one point, I tied his hands to keep them off his cock.

“Please, Mistress,” he begged, his voice strained as I reached down to edge him again.  “I’ll do anything.”

“Will you?”

“I’m sorry, I messed up.”

“Is that so?”

“I won’t do it again, I promise.”

“I almost believe you.  Now hush, I think I can get a few more out of you.”

But the time I finally let him have a ruined orgasm, I was half expecting him to start crying.  But even with not having much relief from all the edging, he was more than happy to not touch his penis for the rest of the night.  And he was decidedly more well-behaved.

We played a bit tonight, and again, I decided to let him cum relatively quick.  But interestingly enough, this time there was no moving away or protesting or telling me he didn’t want to cum yet.

Afterward, I asked him about it, and he said he almost did, more out of habit than anything.  But then, he remembered the way it felt this weekend, and thought better of it.

So yeah, I think that’ll be a much more effective way to break him of that habit.  Way better than spanking him or scolding him.

It’s not a traditional punishment, per se, but it worked pretty damn well.  Yet another useful little tool to put in my tool belt.

A feminine sissy body

What’s sexier than a sissy slut?

Last time I was with Sounder, I noticed something while he was lying on his back, on his pink sissy bed, wearing his pretty lingerie.

He really is looking more and more feminine now that he’s been taking the birth control for awhile. His body looks softer, rounder, with more pronounced curves.

I can already see his tits under his clothes even when he’s wearing his boy costume. And it was so awesome when I realized that his boobs had gotten that big. We were out, having a couple of drinks after work, and he was wearing his normal professional work clothing.

At one point, he stretched in the chair, and I could plainly see the outline of his breasts under his shirt.

It was unbelievably hot.

Of course, that was a while ago, and his body has only gotten more feminine since then.

The most recent things I’ve noticed are his waist and hips. He really is developing a fucking sexy hourglass figure.  I love that I can see that subtle curve in his waist now.  And the longer he’s on the pills, the more pronounced those curves will become.

I mean, look at this picture.  If you didn’t know that this is a biological male, you’d totally look at this and assume it’s a pussy under those panties.

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My sissy is getting closer and closer to permanently crossing that line between masculine and feminine.  She’s getting closer and closer to becoming more girl than boy.

I’m so excited to see how his body continues to change.  Aren’t you excited to see how his body continues to change?

Purple!

So I had to buy a new strap-on after my toy bag was stolen, and settled on a new harness and purple dildo.

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This purple dildo

And as it happens, Sounder bought some new lingerie to surprise me with. Which was purple.

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Isn’t she sexy?

So we’re color-coordinated, isn’t that fun?

And holy shit, my sissy looks amazing with things inside of her.  It makes me want to put even more things inside of her.  Bigger things.

Like my fist.

Yeah, that would be hot as hell.  Let’s make that happen.

The good bottle or the bad bottle?

I love games. Don’t you love games?

I totally love games.

I might have thought of a new game. Figuring out logistics will take some work, but it’s possible.

So Sounder is going to be fucked by Kazander. This we all know.

I was talking to Sounder about that today, specifically about how much of an eager sissy cockwhore he is with me, and how much he dreads being fucked by a man.

What, Jen? What would be awesome?

I’m glad you asked.

Okay, so Sounder has never had a real cock in him. He has no idea what that feels like. He doesn’t really know what to expect.

So here’s what I’m thinking. I’ll tie his wrists to his ankles and lay him on his side.

Like this, except with rope and on his side

And I’ll blindfold him, so he can’t see anything.

Then, either Kazander or I will come up behind him and enter him, careful not to touch him except for the cock.

And then, once one of us is inside him, he’ll have to guess who it is.

We’ll have to be careful, though.

Because if he feels a strap-on harness or bare skin, he’ll know who’s in him. He also knows my touch, so if one of us grabs or touches him, he’ll know.

I’ll have to use a new dildo, too. One right about the same size as Kazander’s cock, that Sounder has never seen. Preferably one of the ones that are supposed to feel realistic.

With him tied up like that, we should be able to get almost all the way in him without touching him.

Hopefully. And that’s where I wonder if it might not be feasible. There’s such a tiny margin of error. If he feels or senses or hears anything else, it’ll tip him off.

But if it goes right…

All he’ll have to go on is the cock inside of him.

If he guesses right, we’ll spitroast him, with me fucking his pussy and Kazander fucking his mouth.

If he guesses wrong, we’ll switch. Kazander will fuck his pussy and I’ll fuck his mouth.

And of course, I love the idea of Kazander being the one in him, and then when he makes his guess, I’ll take the blindfold off, and he’ll look up to see if he guessed right.

And he’ll look up to meet the eyes of the man whose cock is inside him right at that moment. Not only will he realize that a man’s cock is penetrating him for the very first time, but he’ll look up and meet Kazander’s eyes, as he feels his cock filling him up.

Whether or not he guesses right, that could be a fun moment.

Of course, if he guesses right, that means Kazander will pull out of him and start fucking his mouth. So he won’t have to be fucked by a man, but he’ll still be facefucked by one, and he’ll still have to swallow his load, and he’ll get to experience ass to mouth for the very first time.

But then again, that may be too easy. Sounder is very much aware of my love of a good mindfuck. And putting Kazander in him is definitely something I would do, just to fuck with him.

So he would likely expect that.

And besides, it would also be amazing if I’m the one in him, and he guesses wrong, and realizes that he could’ve had me fucking him, and instead he gets to deepthroat my cock (which was just in his pussy) while a man fucks him.

But he may expect that, too. Because putting Kazander in him is the obvious choice. He knows I’m not going to go for the obvious choice, so he may expect that it’ll be me in him.

In which case I’ll definitely need to put Kazander in him.

Really, it’s less about trying to determine what’s inside of him by the way it feels, and more about what he thinks I’m going to do.

It’s like that riddle in Sherlock and Princess Bride.

Did I put my cock in him, or Kazander’s?

“Did I give you the good bottle or the bad bottle?”

You know, except no one dies, and we spitroast a sissy.

How many times will I go back and forth before settling on the answer? What do I think he’ll expect me to do? What does he think I’ll expect him to guess?

Like I said, I don’t actually know if it can be done, but if it can, you’d better believe that’s what I’m going to do, and it’ll be so much fun!

Creating a submissive mindset

One of the things I’ve been asked most often by inexperienced Dominant women is how to create a submissive headspace in their partner.

And yeah, it can be tough.  Real life and its responsibilities can make things difficult, and put a sub’s headspace far from where it should be.

The best way, in my experience, is to appeal to the sub’s lust and desire, and combine that with surprise and humiliation.  This combination creates a firm reminder of his position in the relationship, and the surprise is to jar his head a bit, to break the hold that the real-world bullshit has on him.

Interestingly enough, I was just talking today about something I’ve done to surprise and alter my boys’ headspace, so I figured I’d do it again tonight.

Kazander’s had a rough couple of weeks at work.  Like, rough enough that he may start looking for a new job.  And rough enough that trying to achieve a submissive headspace when he gets home takes a lot of effort.

There are a number of ways to combat this.  But one of the most effective is one of the simplest.  You can’t do it often, or it’ll lose some of the effectiveness, but when it’s done right, it works wonders.

I told him to text me when he was on his way home from work.  As soon as I got his text, I took the kid next door and left her with the SIL, who had agreed to watch her for a few minutes.

Then I grabbed my strap-on.

I was standing there, with the strap-on harness on and lube in hand, when he walked in the door.

I’ve done this to him before, but not for a long time, so he was sufficiently surprised.  After a long day, it was the last thing he expected.

Without a word, I grabbed his arm and pulled him inside.  I bent him over the back of the couch and reached around to unbutton his pants.

“I don’t know if this is a good idea,” he said.  He’d just gotten home from a long day in a warehouse with no climate control.

But honestly, I don’t care.  So what if it’s a little dirty?  There’s this new invention out, brand spanking new, just hit the market today.

It’s called soap.  And indoor plumbing.

And I felt like objectifying him just then.

“Shut up,” I told him, pulling his jeans down and exposing his ass.  And as soon as I did, his lust took over (I know, it doesn’t take much).  When he felt my hands on his thighs, he moaned softly and pushed his ass out, wanting to be fucked.

Such an eager anal slut.

I didn’t say anything as I started pounding him.  In that moment, he wasn’t a man, he wasn’t a person.  He was just a hole for me to take my enjoyment from, and I wanted to make sure he knew it.

The play didn’t last long.  It didn’t have to.  After I’d had my fill of fucking him, I pulled out, spanked him once, then just walked away and left him there with his pants around his ankles.

He sighed and pulled up his pants, his headspace firmly where I wanted it, the rough day at work forgotten.  After we’d cleaned up, he dropped to his knees behind me and asked to kiss my ass and my feet before we went to get the kid.

All in all, it lasted barely twenty minutes.  And he was in a much more relaxed and submissive state of mind the entire night.  Just twenty minutes, that’s all it took.

It’s so simple, but so effective.

Sissy porn stash

It’s been a busy couple of months, but no matter what else is going on, I always make time to enjoy just how sexy and photogenic my sissy is.  And luckily for me, I have my very own personal sissy porn stash.

The last couple of months have been a bit wonky as far as both of our schedules go, but usually, if I’m not there with him on Sissy Sundays, Sounder makes time during the day to take pictures for me.

And they’re beautifully edited, so delightfully slutty, and unbelievably hot.

The pictures I take of him are pretty fun to look at, too.  I’m never ever going to not enjoy seeing him with something inside him.

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Case in point

I mean, just look at that gorgeous, perky ass.  It just begs to be filled.

My favorite, though, is the stuff I can’t share here.  Particularly the videos I’ve taken of him.

Like the first time he came while straddling me, riding my cock.  That’ a fun video to watch.  Or the most recent one, of him on all fours in that sexy lingerie, fucking himself on the dildo, arching his back and pushing against me, wanting it deeper inside him.

The holidays have messed with my ability to fuck that sexy, slutty, eager ass of his.  But it happens, real life tends to get in the way of kinky fun occasionally.

And at least I have some amazing porn to look at until I can throw him down onto the bed, push his legs back, and ram my cock into him over and over again.

A good, thorough fucking

It had been awhile since I’d been able to give Sounder a real fucking.  We were both eager for that to change.

And from the very first moment I bent him over the island in his kitchen, and slid a finger in him, he was every bit the eager anal whore you’d expect a sissy to be.  Pushing back against me, humping himself on my hand, wanting to be filled up, it was really hot.

I always love watching him squirm.

It was especially hot once I got him in the bedroom and started putting toys in him.  I will never get tired of watching him fuck himself on whatever’s in him.

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I can’t wait to take a picture like this, but with a real cock inside him, instead of a toy.

At first, he was so tight.  It had been too long since I’ve really had my way with his pussy, so I was gentle.  I started small and gradually worked my way up in size.  Because I’m so totally nice like that.

All I know is that he’s going to make a man very happy when I put a real cock inside him.  And how awesome are backless panties?  The more he wears them, the more I love them.  So sexy, so convenient.

I don’t even have to undress him, all I have to do is bend him over.

When I finally switched to my strap-on, the look on his face as I filled him up was priceless.  It had been awhile since he’d had anything that big in him.

I turned him onto his back, pushed his knees up, exposing that tight, pink ass, and rammed my cock in.

He looks damn good with something in him, by the way.

I don’t think it was a full minute before he came.  And then came again.  And again.

We’ll definitely have to work on his stamina.  He starts getting exhausted and raw after about ten orgasms.  He’ll have way more than that when he’s fucked by half a dozen men.

Eventually, though, I had mercy on him, and decided to play with my clothespins, instead.  You know, because I’m nice like that.

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Super nice

He really is so adorable when he’s in pain.  And the best part about clothespins is that they hurt more coming off than they do going on.  Makes it easy to drag out the pain, really savor those reactions.

And he’s got a new hypnosis recording to listen to every day.  I’m going to brainwash him into a mindless sissy fucktoy.  He’s going to dream about being gangbanged, he’s going to crave men’s cocks in him.

Eventually, it will even seep into his everyday life.  He’ll be at work and see a hot guy, and an image of that guy bending him over his desk and fucking him will flash through his mind.  He’ll imagine what that man’s cock will taste like.  What it’ll feel like to have it throb in his mouth as it shoots down his throat.

Just a quick flash.  But they’ll start happening more and more, until that’s the norm, until he doesn’t remember what it feels like not to picture men fucking him.  He’ll forget what it feels like not to crave a man’s dick inside him.

It’s going to be so much fun, it really is.