Hell Night

That’s what Sounder has taken to calling it.  And the thought of it has him so much more flustered and messed up than the birth control pills ever did.

Which means I’ve been downright fucking giddy.

What’s super fun is that I installed a countdown app on my phone, counting down the days, hours, minutes, and seconds until Hell Night.  And I do so love reminding him how much time he has left.

Hell Night, which will take place in approximately two weeks, is an afternoon/evening filled with totally amazing awesomeness.

It’s going to start by going to a woman who specializes in MtF makeup.  She’s going to do his makeup and style his wig.

Which would have been plenty unnerving for him on its own.  But hell no, I’m not going to get him all made up like that just to take him home, so no one will be able to see it.

Still, just the makeup on its own has him rattled.  Of course, in keeping with the way his mind works, his biggest concern is “What if it doesn’t look good?”

Of course it’s going to look good.  It looked good when I did his makeup.  And I am by no means a professional.  This woman does this for a living, and is quite good at it.

Oh, and I’m so excited for that.  She’s awesome, I can’t wait to see her in person.  Talking on the phone to her was a blast.  I told her I’d like to set up an appointment for Sounder, and even though I referred to him as my “boyfriend,” she still used feminine pronouns, which had me grinning like a maniac.  Like seriously, I couldn’t have imagined it being any better.  Just the process of putting on his makeup and doing his hair will be beyond epic.

But Hell Night will only just be beginning…

So I have three different activities planned after he gets his makeup done, and looks all beautiful and sissified.

The first activity, I already have planned and set up.  I need to make one more call closer to the date, just to confirm, but I’ve already talked to the folks I needed to talk to, and it’s all set and ready to go.

I originally planned on not telling him, and surprising him on that day.  But his poor head seemed like it was going to explode, and I decided to try to cut him a break.

So I asked him if it would be better on him if I told him.  He said, “Everything you’ve told me so far is all nerve racking and bad, it definitely can’t get worse.”

It definitely can’t get worse?

Oh, honey.  Have we met?

“I’m taking you to Victoria’s Secret to get fitted for your first bra.”

“Oh fucking hell.”

Poor thing, it really just made him more nervous.  I could tell he was toeing that line between “fun” freaking out and actually freaking out.  So I reminded him that I had every aspect covered, that I was incredibly thorough, and that I would take care of him.

And it’s true.  I pulled the manager aside and talked to her about it, and she was very welcoming and enthusiastic, and began relaying a story about a trans woman who had been in for a bra just a few weeks ago.  She didn’t know yet if she’d be working that day, but gave me her name, and told me to call closer to the date.  If she was working, she’d take care of us personally.  If not, she assured me that the other manager would be just as delighted to help us, and to ask for either of them by name.

Of course, if the other manager is working, I’m going to talk to her myself, before I bring Sounder there.  The general public can’t be accounted for, and ignorant people are everywhere (assuming they’d even know he’s not a girl), but with both managers aware and on my side, we’ll definitely be safe from any potential issues.

I’ve also had a chat with one of the security managers, who was very eager to offer any assistance needed outside the store, itself.  He gave me his name and number, and assured me we’d be well taken care of.

But for all the preparation, and the covering of all the bases, I’m really thinking it’s not going to be hugely obvious that he’s not a girl.  I know he’s worried about it, but I really think it’ll be unlikely that people would immediately recognize that he’s not a girl.

It helps that he isn’t huge.  This would be a lot harder to pull off if he was 6’3″ or something, and built like Terry Crews.  In my experience, the sheer size of some men is the biggest obstacle to overcome.  You can put Terry Crews in a dress, and the best makeup artist in the world could do his makeup, and you still wouldn’t be able to convince anyone that he’s not a man.

But while Sounder isn’t Terry Crews, he’s still bigger than the average woman.  Luckily for him, so am I.

He’s toned and slender, and about my height, and I’m no petite thing, myself, so just having me there with him will make him more passable.  Particularly if I put him in flats, while I wear heels.  That’ll make me taller than him, which will further offset his size and make him appear smaller.

Look at that, my big Amazonian ass works to my advantage once more.  God damn, I love being tall.

Once that’s done, we’ll head to a bar/restaurant/whatever, to grab a couple of drinks and maybe something to eat.  I still need to do some scouting, I have some people I can reach out to, to find a place that a) isn’t a complete dive, b) isn’t populated by ignorant, nosy rednecks, c) is open and welcoming to sissies and crossdressers, and d) will not be a likely place to run into anyone he knows (which is surprisingly difficult, actually.  My first three ideas were trashed because the possibility of running into someone he knows is just too great).

And then, for the finale, he’s going to suck his first cock while in full sissy mode.  I’m going to be nice, and not make him swallow probably, but I’ll have to think of something equally humiliating (that won’t mess up his makeup, so cumming on his face is out).

By then, I’m sure he’ll be worn out, and nice and overwhelmed.  He will have had a long day, and will be more than deserving of a reward.  So I’ll bend him over, hike his dress up, and give him a long, thorough, deep fucking.

We found out the other day that yes, he can cum from anal.  Repeatedly.

Recently, we’d been having trouble with anal.  He’d get these terrible, excruciating cramps, and we couldn’t figure out why.

As it turns out, it was his position.  Usually, when playing with his ass, I’d have him lie on his stomach on the bed.  The other night, when I was there, he suddenly rose up onto all fours, and I could immediately tell there was a big difference.

He said it was so much better that way, and very soon lost himself in the sensation.

I knelt behind him, holding the dildo more or less still, and let him fuck himself on it.  It had been awhile since I’d really been able to fuck him good, and didn’t want to push him too hard.  I also wanted him to get reacquainted with the feeling, and to experiment a bit with what felt good.

And holy hell, it was so damn hot watching him impale himself on it.  He rocked back and forth, pushing back against me, wanting it deeper, harder.  At one point, he moved forward until the dildo came all the way out, then immediately backed up onto it again, but only enough that the head went in.  And then he moved forward again, until it came back out.  He did that for a few minutes, moaning and squirming, before pushing back against me again, sliding the dildo all the way inside him, as far as it would go.

Suddenly, he cried out and fell forward onto his stomach, gasping and panting.

“Did you cum?” I asked him.

“Yes,” he answered.  He reached underneath him, expecting to feel a wet spot, but there was nothing there.  “No,” he corrected.

I laughed.  “Good, so it’s your first anal orgasm in awhile.”

“That was the second,” he told me.

“Well get back up here, and let’s go for number three.”

He pushed himself back up and onto my dildo, gasping as it slid easily into him.  And again, I held it still, letting him set the pace, giving him the freedom to explore it, and watching him get more and more worked up.  He pushed against me, he rotated his hips, swirling it around inside him, he bucked and jerked.  Only a few minutes later, he pushed back hard against me for a moment before falling back onto his stomach, whimpering.

It was his third orgasm.  But I wanted one more.  So once again, he pushed himself up, and I pushed the dildo into his sore, throbbing, gaping hole.  I held it mostly still, but I did start fucking him with it on my own.  It didn’t take long before he came a fourth time, getting close to screaming as he fell forward once again.

He was so cute, lying there, still squirming a little bit, and whimpering softly.  I gave him a couple of minutes to recover, running my nails up and down his back.

But I wasn’t done with him.  Fucking him had gotten him nice and overwhelmed.  Now I wanted to overwhelm him from the other side.  I told him to roll over, plugged in my wand, grabbed the lube, and held the wand against him with one hand, while stroking him with the other.

It didn’t take long before that started getting overwhelming.  He writhed and thrashed on the bed, turning to try and get away from me, his hands balled into fists.  At one point, he grabbed one of his pillows and screamed into it, which made me smile.  It was the first real scream I’d gotten from him.

It seemed like only a few minutes had passed before he was begging me to stop.  And his adorable pleas of “No, please,” were so fucking sexy.

I pushed him just a little harder before finally turning the wand off.

So it’s official.  The pills have killed his dick.  He can no longer cum like a man.  He can only cum from being fucked.

Which is fucking awesome.

The next day, he was still feeling the effects of it.  He made the comment that his head was still foggy, and he may have had to call in sick if I’d done anything else.

Which is now my new goal, obviously.  I want to overwhelm him to the point that he needs a full day just to recover.  And really, I came pretty close to it.



If you knew Sounder, you’d know that asking if he hurt himself tackling someone at work, while wearing a suit, is a perfectly legitimate question.

If you ever fuck someone, you know you blew their mind if they’re still feeling a buzz from it 16 hours later.

He’s been sleeping in girls’ pajamas lately, the newest step toward being a full-time sissy, and it’s still a new feeling for him.  Waking up, realizing what he’s wearing, gives him a fantastic submissive feeling.  So naturally I wanted him to sleep plugged, as well.  We’ll see when he wakes up how that feels for him.

My eventual goal is to keep him plugged for a full 24 hours.  And that’ll be fun.

5 thoughts on “Hell Night

  1. Mic says:

    Well, even with the whole sissyfication being not my cup of tea it is absolutely fascinating what’s going on between you guys. And Jen, I am particulary impressed about the efforts you make to ensure that Sounders Hell Night will be an overwhelming experience for him. I said it before I guess but I say it once again: your responsibility and care for your submissives is absolutely striking! Maybe he will have a hard time but it will be an extremely good organized time! 🙂

    • Domina Jen says:

      Thank you! My subs are my favorite people, and no one can ever accuse Sounder of worrying too little, so it’s important to me that I do everything I can to assuage his concerns and keep him focused on what I want him focused on.

      I’ve considered every detail, every angle, every even-remotely-conceivable possibility, and am creating a plan for each. It’s still two weeks until that night, but by then I will have solidified every plan, every contingency, every option.

      So he will not need to worry about those details. He will be able to focus on what I want him focused on, assured that he’s in capable hands, and I will protect him and take care of him.

      • Mic says:

        I read a lot of blogs and homepages about domination and submission, because I’m interested in the lifestyle. And therefore I have to say that it isn’t the standard to assure the subs in the way you do.

        That makes your blog always a pleasure to come to and read about the things going on. And again: thanks for sharing!

  2. collaredmichael says:

    I like your attention to detail! Sounder will have an amazing experience that is about as safe as it can be. I wonder if you might post a picture of his changing body–no face or head shown–so we can see the development of his breasts and hips. I admit to finding this process fascinating!

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