“You can always make it worse”

It started innocently enough.

A conversation about porn.

He’d stumbled across something with a man being forced to wear a wig, and the novelty of it got his attention.  So he started looking into it.  He never realized that forced femme was that big of a category.

His first mistake was telling me about it.

His second was admitting to that the idea made him jittery and nervous.

Oh, it’s on. 

I now knew what I was going to be doing with him.

I spent a good deal of Sunday texting back and forth with Sounder.  The more we talked about the fetish, the more I realized how nervous it made him, and the more I dug in.

And then he signed his death warrant with his third mistake.

This, class, is what it looks like when a boy signs his own death warrant.

This, class, is what it looks like when a boy digs his own grave.

This was going to be too easy.

Like seriously.  It’s almost not fair, how easy they make it sometimes.

We were all set for me to go see him on Tuesday.  And I was going to make damn sure that he would have a whole fucking lot to think about between Sunday and Tuesday.

Most of the day on Monday, we texted back and forth while he was at work, as well as when he got home.  And he’s a smart boy.  He started noticing a pattern relatively early on.

wp_ss_20150825_0010Perceptive, isn’t he?

I want to point out here that he has exactly four hard limits: the “Big 3” (scat, animals, and kids) and anything that would fuck with his career.  Anything else (and I mean fucking anything) is fair game, although certain things might take a bit of “working up” to it (such as a PA piercing, or tattoo, or anything like that).  Still fair game, though.

Oh dude….

A few suggestive scenarios, a few strategically-placed details catered specifically to the triggers that I’d discovered in him, and the inevitability, the finality, of it, was pretty much all I needed.

I’d figured out how to rattle him, how to shake him.  Which, as it turns out, is not something easily done.

wp_ss_20150825_0007Score one for me.

There was so goddamn much going through my head by that point.  Things I could do to him, things I could force him to endure, things I could make him do.  He’d been forced into being bi by a previous Mistress, but his experience was limited to giving blowjobs, so you know I’m going to capitalize on that.  Combining that with the forced femme is just the logical thing to do, amirite?

As the possibilities multiplied exponentially, and he got more and more nervous, it only spurred me on even more.  And he became quite familiar with my ability to take what he feared, take what was in his mind, and make it quite a bit worse.

My head is much darker than his, my experience within forced femme is extensive, and there’s nothing he can think up that I can’t turn around and use to fuck with him.  I can always make anything worse.

And he was learning.  He repeated it again yesterday (Tuesday).

Like really, really cute.

Like really, really cute.

By the time Tuesday evening came around, he was pretty flustered.  I’d brought a wig, some lipstick, and a pair of panties with me, along with my usual bag of toys.

It’s not much, but oh, it was enough.

Almost immediately after walking in the door, I pulled a glass buttplug out of the bag and told him to put it in his freezer.

We chatted for a moment, and he laughed, saying that he hadn’t gotten much “thinking” done that day.  And I absolutely believe him.

When he finished his glass of wine, I turned to him and asked him why he wasn’t naked.

And he got flushed and started stammering right there.

Seriously.  Too easy.

He took off his clothes, and I handed him the panties, telling him to put them on.

And y’all, they look seriously cute on him.  Like really, really cute.

I turned him around, bending him over to brace himself against the dining table, and started groping him.  I reached my hand around and started playing with his dick, sometimes being nice to it, and sometimes being not-so-nice.

The way his knees buckle when he’s in pain is adorable.

After a moment, I went back to my bag and pulled out my trusty Thunderstick, the most amazing thing ever invented, and plugged it in to the outlet behind him.

He reads the blog, and I grinned as I approached him.  “Have you read about this?” I asked him.

He nodded.  “Yes.”

“So you know what it’s capable of.”

He nodded again as I placed it against the head of his dick and turned it on.  I kept the setting low for a few moments, enjoying his reaction to it.

But he seemed to be enjoying himself way too much.  We can’t have that.

So I turned it up.  Not much, but enough.  He started squirming and moaning, gripping the back of the dining chair, rocking back and forth.

Oh, but I wasn’t done.  I turned it up again, leaving the “pleasurable” settings behind in favor of the “torturous” ones.

And I couldn’t help but laugh as his knees buckled, his voice went higher, and the squirming intensified.

“Do you think that’s as high as it goes?” I asked him.

He shook his head.  “No.”

Smart boy.

I turned it up higher, and the intensity was really starting to get to him.  It was seriously fucking entertaining, y’all.

“What about now?” I asked after a minute.  “Do you think this is as high as it goes?”

Again, he shook his head.  “It’s probably not even close,” he managed.

“Well, it’s a little close,” I said.  “There’s not too much left.”

To prove my point, I turned it up as high as it would go and held it firmly against him.  He damn near screamed (which was awesome) and tried to pull away, but I had my other arm around his hip and held him still.

Well, still-ish.  There was no “holding still” at that point for him.

After a few seconds, I took pity on him and turned it back down to the nicer settings, still holding it against him as he writhed and moaned.

Then I wanted to hurt him.  He’d figured out a way to tie a rope from the top of the staircase down to the bottom, and I tied his hands together, keeping them above his head.  It was a bit cramped, but definitely doable.  I started in on him with the flogger.

It’s at that point that I realized I’d forgotten my paddle.  And goddammit, I even thought about it as I was getting everything together, telling myself not to forget about it.

And what did I do?

I fucking forgot it.

Well, that’s alright.  I still had my flogger, and I had my hands.  I could spank the fuck out of him (or not, more on that in a minute).

He gets so delightfully red when you beat him, and within minutes, his whole ass was beat red, and I could see where a couple of particularly hard swats had caused little welts to raise.  Hopefully those wouldn’t go down by morning, but he’s said before that the marks left by beatings usually fade disappointingly fast.

Then, I started spanking himHe tensed up, and I laughed.  “That’s not going to help you,” I told him.

“It’s not intentional.”

I spanked him for a bit, pretty hard, then switched back to my flogger.  I think I switched back to spanking him again at some point, I don’t remember.

But at one point, shortly after spanking him, I felt an odd tingling in my hand.  When I looked, I was shocked to find that I’d spanked him so goddamn hard, I’d broken a few blood vessels in my hand, and the blood was pooling under the skin in two of my fingers and my palm.

And you wanna know the worst part?  He hardly even reacted to the spanking.  It was like it was nothing.  I broke blood vessels in my hand, and it didn’t even bother him.

That is one firm fucking ass.

That is one firm fucking ass.

Yeah, I am definitely bringing my paddle with me next time.  And I think I’m going to buy a much heavier, much more severe one, as well.

But then, I guess it’s fitting.  I tried to destroy his ass last time, so it’s only fair that I try to destroy my hand this time.  Karma and all that.  And I’ve broken blood vessels before, back when I was a martial arts instructor, and it didn’t even hurt, so I just went on flogging him.

I went on for a bit, but every time I looked back to the living room, I saw the wig lying on the arm of the couch, and I really, really wanted to put it on him.  So I untied him and told him to bring one of the dining chairs into the bathroom.

Silly boy thought the chair was for me.  The look on his face when I told him to sit down was priceless.  Sitting down put him right in front of the mirror.  He sighed as I tied his hands to the chair.

“Yeah, you can always make it worse,” he said quietly, looking at his reflection.

I laughed, then went and got the wig and lipstick.  I put the wig on him, and arranged it, and pinned the bangs to the side, out of his face.  The whole time I adjusted it, he kept his eyes down, really, really not wanting to see it.

“Look up,” I told him.  He obeyed, looking at his reflection, at his face framed by the long, curly red wig.

And you know what?  It actually wasn’t hateful.  First of all, I love the color on him.  It makes his eyes look bluer.  The style and length don’t fit him at all, but that’s something that can easily be fixed with a trip to the salon to get it cut and styled.

The look on his face when I told him that was priceless.

“What’s wrong?  You don’t want to go to the salon and get it styled?  We could have a spa day, just us girls.”

He was less than enthused about the idea.

Next I put on the lipstick… and he definitely needs a different color.  All I brought with me was a bright, warm red.  I think he definitely needs something a little cooler.  But after I put the lipstick on him, I told him to look at his reflection again.

“What do you think?” I asked him.

He laughed nervously.  “It looks awful.”

“Oh, no it doesn’t.  You just need a better hairstyle, something that fits your face.  And full makeup.  And your eyebrows waxed.”

He laughed again.  “I’m sure makeup would cover the five o’clock shadow,” he joked.

“Oh, I know how to hide that,” I said dismissively.

He wasn’t expecting that.  And his reaction was adorable.

But as we chatted, he kept avoiding looking in the mirror.  “Does it make you uncomfortable to look?” I asked, grinning.

There was that nervous laugh again.  “Yeah, a little bit.”

“Look.”

I made him sit there for a few minutes, in front of the mirror, telling him all the ways I can make him look more feminine, all the little tips and tricks I’d picked up through the years.  We talked about breast forms and waist cinchers and all kinds of different lingerie made specifically for biological men.

He had no idea that all of that existed.  So that was a learning experience for him.

Finally, I let him up, told him he could put the chair back (but leave the wig on), and we went upstairs to his bedroom.  Once there, I tied his hands behind his back and started playing with his tight, smooth ass.

Oh yeah, I don’t think I mentioned before.  He shaves.  He’s completely hairless down there.  So awesome.

I fingered him for a bit, eventually working up to two fingers, playing with his prostate, gently fucking him.

Then I remembered the glass plug and left him there to go down and get it.  It had been in the freezer for about an hour and a half, maybe a little bit longer, and was nice and frozen.

I walked back to the bedroom, lubed it up, and started pushing it into him.

Ooooh, and he made such awesome sounds!

After a moment, it was getting to be too much for him, and I pulled it back out.  I don’t think he expected it to hurt that much.  I gave him a bit of break, then pushed it about halfway in again, laughing as he squirmed and moaned.  He couldn’t handle more than a few seconds, and once again, I pulled it back out.

“Fuck, that hurts,” he groaned.  I laughed.

“Does that mean I found something you can’t handle?”

He didn’t really answer, and I grinned.  “Well, now I know a good punishment if you fuck up.”

There was that little nervous laugh again.  “If that’s the punishment, I damn sure won’t fuck up.”

“Smart boy.”

I hogtied him and switched to the vibrator, nice and slender, and fucked him with that.  He really does moan so sweetly when there’s something inside him.  It’s adorable.

A bit later, I left the vibrator in him, left him hogtied on the bed, and went downstairs to get my Thunderstick.  I brought it up, plugged it in, and turned it on low, pulling his dick and balls out from underneath him and holding the wand to them.  With the vibrator inside him and the wand vibrating against his dick and balls, he seemed to be more or less enjoying himself.

After awhile, though, being hogtied like that made his back start hurting, so I let him up.

The last time I fucked his ass, he’d been lying on his stomach, and this time, he’d been hogtied.  So I wanted to see his face while he was being fucked.  I tied his hands above his head to the headboard, then went to get the larger dildo.

“Is that what was in me?” he asked, amazed.

“No.  This is what’s going in you now.”

“God, I wish I hadn’t seen that.”

I can always make it worse.

“Please, this is nothing.  I’ve seen real dicks bigger than this.”

I knelt between his legs, lubed up the dildo, and pushed it inside him.  And yeah, I definitely love watching his face while he’s being fucked.  I was much gentler with him this time than I was last time, and fucked him nice and slow.

I grabbed my wand and held it against his dick, his balls, and the dildo inside him.  Then I reached up to twist and hurt his nipples, which always gives some great reactions.  He’d flinch before I’d even touch him.

I figured out how to cause some pretty fantastic pain by holding and manipulating his balls a certain way, sort of rolling them between my fingers.  It didn’t even take very much pressure, and he was jumping and howling and pulling on the ropes.

Then, we started talking again about all the ways I want to use him, all the ways I’m going to feminize him.  There was a picture I showed him on Monday, of a man dressed up in a wig and a dress, complete with stockings, heels, makeup, the whole nine yards.  He was hogtied and gagged on the kitchen island, while two women stood beside him, tormenting him.

Sounder has an island in his kitchen, large enough for him to lie on.  So immediately I wanted to do that to him, and have a party, and make him the centerpiece.

wp_ss_20150825_0006Since public play still freaks him the fuck out, I had a lot of fun with that idea.

So we were sitting on his bed, me teasing his dick, his hands tied above his head.  We talked about that, as well as my desire to get him a wig and then take him to a salon to get it styled to fit his face, and get pedicures, and facials, and have a girls’ spa day.

And the idea of the salon was making him more and more and more rattled.  He asked if we could take “baby steps” instead.

I said, “Why?  It’s like getting into a cold pool.  Would you rather take 45 minutes to ease yourself into the pool, feeling the same shock over and over again as another body part touches the water, or would you rather just jump in and get it all over with at once?”

“That’s not the same thing!”

“Sure it is.”

He suggested maybe getting a few cheap wigs, and seeing how I liked them, and starting from them.  Anything besides me making him go to a public salon and get it styled.

But then I asked, “Which would you rather have happen?  Getting the wig styled, or being the centerpiece at my party?”

Without missing a beat, he said, a little frantically, “The party!  Definitely the party!  I’ll do the party next weekend if you don’t make me go to a salon.”

……… Oh really?

“You’d be okay with the party?  With being hogtied on the island?”

“Yeah.”

“So I can bring people over here and let them humiliate and degrade you?”

“Yes, if you’ll let me take baby steps with the wig.”

Fucking done.

So I’m going to start working on that party.  It’s not going to happen this weekend.  Or next weekend.  It probably won’t happen until after I get back from North Carolina.  But that is absolutely happening.

And that’s fair enough.  I’ll let him take baby steps with the wig.  We’ll hold off on going to the salon indefinitely (for now).

See?  I can be nice.

He says he still feels like he’s getting off too easy (which is true), so I’ll do the party, along with something else that I haven’t quite decided on yet.  I’ve got my party, and he owes me one.  Which is a fucking awesome thing I’ll get to hold over his head for awhile.

Granted, it’ll be a small party, and I think I’ll be nice and only invite females (see, I’m doing that baby-step thing) but it’ll still be a fun way to introduce him to public play and humiliate the hell out of him at the same time.

Win-win.

Oh, and he’s going to start wearing panties.  All the time.

Well, except for when he’s working out.  But there’s an actual, legitimate reason, so I’ll give him that.  And of course, he’ll have a couple of pairs of men’s underwear for doctor appointments and such, but other than that, all he’s ever going to wear is women’s panties.

I untied him, set the wand down, and we chatted for a bit more, then I looked over and saw that it was after 10:00pm.  He gets up at 4, and he hasn’t been sleeping well the last couple of nights (which I may be a bit responsible for…. my bad).  When I saw him try to hide a yawn, I got up and started gathering all my things.  I’d kept him up late enough.

He put some clothes on and we went downstairs, where he pulled out a gift bag and set it on the counter.

Ooooh, I like presents!

When we’d gone to the bar, the first day we met, he discovered that I love margaritas.  So he bought me a huge bottle of really good tequila (that, as it happens, is going to be gone by this weekend.  I stopped by the store on my way home and picked up a bottle of that ready-made, just-add-alcohol watermelon margarita mix… It’s safe to say I’m going to be in a pretty damn good mood every night, even with my mom being here).

He walked me to my car, I hugged him, and drove away.  I’m going to spend some time this evening finding a couple of different wigs for him, checking out some of the crossdresser websites (he was shocked when I was able to rattle off the names of two or three, just off the top of my head), and looking at panties.  And all kinds of clothes, really.

He’ll be fun to shop for as far as clothes.  He’s got an inverted triangle body shape.  He’s got broad shoulders, a small waist, and no hips at all, so I’ll need to keep that in mind when I look at clothes for him.  I need things that will accentuate his hips and soften his shoulders to give him a more feminine shape. Good thing I know just as much about fashion as I do about kink, huh?

So yeah, he’s going to be a lot of fun to play with.

6 thoughts on ““You can always make it worse”

  1. Wow! Absolutely incredible night for him.

  2. Mic says:

    This one was a great pleasure to read. Thank you for sharing it with us!

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