Sissy slut

I’d been wanting to have Sounder’s makeup professionally done for awhile.  The transformation I could see in my head just exceeds my own skills.

So we set an appointment for this past weekend.  And, as I’m sure you all know, I had lots and lots and lots of fun in the days and hours leading up to that appointment.  The poor sissy’s blood pressure was probably off the charts.

He was so nervous and flustered.  It was adorable.

I went to his house, grinning when I saw that he’d moved both his truck and his motorcycle so I could park in the garage.

Clever girl, thinking ahead like that.  Can’t have the neighbors thinking that I’m bringing random sluts to his house.

We had a few minutes before we had to leave, so we made sure we had everything we’d need, and spent a bit chatting.  He poured me a glass of wine, and refilled his own glass.  I couldn’t help but laugh when he pulled a small bottle of liquor out of a cabinet and put it in his pocket.

“You know that’s not going to help you, right?” I asked.

“Oh, I know.”

We got into my car and I drove to the place.  The woman greeted us, and told us that it would be just a few minutes, and she’d be right with us.  I entertained myself by looking at her massive wall-o-pictures, pointing out some of the better ones to Sounder.

Because as nervous as he was about being made into a feminine sissy, and what he would have to do later (oh I had plans for him), there was one thing he was significantly more nervous about:

What if it doesn’t look good?

For weeks, we’d been going around and around about it.  He was wholly unimpressed by the pictures he found on her website and facebook page, and was nervous that she would do a terrible job and he’d look awful.

I pointed out that, if someone isn’t an attractive man, they’re not going to make an attractive woman.  Also, quite a few of the pictures posted were of people who were a bit older than Sounder.

A 65-year-old man is not going to get his makeup done and come out looking like Emilia Clarke.  He’ll come out looking like a 65-year-old woman.  Which, of course, is fucking awesome.

But when you’re a 40-year-old, with just the teensiest tendency to worry awholefuckinglot, and with no “before” pictures to compare, all those somewhat-manly-looking pictures aren’t super reassuring.

More than the humiliation of having to endure it, more than being seen by more than one person that way, more than yet another piece of his masculinity being taken from him, that was what worried him the most.

But I’ve done makeup (mostly on myself) for awhile now.  I’m no professional, but I’m pretty good at it.  And no one has ever studied his face the way I have. He’s got a good face shape, striking blue eyes, and dark hair (which would be covered by the wig anyway).  He’s an attractive man, and I knew, just because I know these things, that he would look amazing as a woman, too.

He still wasn’t convinced by the pictures on the wall, and soon it was time for us to go back.  She told us to get him completely dressed from the neck down.

And that’s when we realized that the fashion choice I made wasn’t the best option.  I told him to bring a short, black bodycon dress that he looks fucking amazing in.  I forgot how heavy and thick it is, I forgot about the long sleeves, and I wasn’t expecting her to have practically no air conditioning.

Because it’s only 111 degrees outside.  Why would you want your place of business to have air conditioning?

Yeah, so oops.  I told him he could change as soon as we got back to his place.  He put the dress on and sat in the chair, facing the mirror.  A moment later, the woman came back and asked me what kind of makeup I wanted.

“Do you want sweet?  Sultry?  Day?  Night?  Glamour?”

“Let’s go with sweet and innocent,” I told her, with a very not-sweet-and-innocent grin at Sounder.

I had to laugh, though.  A minute in, she paused and turned to me, and asked, “Do you want his eyebrows gone?  I have wax, do you want them gone?”

And my immediate thought was, do not wax his fucking eyebrows off, you psycho!  Seriously, I think my heart rate almost doubled.

But no, she meant covering them up with eyebrow wax and drawing a more feminine brow on him.  Which was way better.  She assured me that the wax would come off with soap and water, and he’d be able to be fully back in “guy mode” (or, more accurately, “pseudo-guy mode”) the next day.

She could tell from the beginning that I was running the show.  She directed all her questions to me, she asked my opinion instead of his, and I was the one she primarily spoke to.  But both Sounder and I picked up on the fact that our particular dynamic was not her normal clientele, and that she wasn’t particularly into it.

Which was a bummer, because when I first talked to her (at least, I assume it was her.  I don’t think there’s anyone else), she seemed so into it.  She giggled when I gave her Sounder’s sissy name, instead of his legal one.  She seemed intrigued when I explained what I wanted to do with him afterward.

I’m thinking she might have been fascinated by the idea, but the reality may have been a little jarring for her.  She’s used to men who want the makeup, who are already somewhat feminine in their voice/movements/body language/demeanor/whatever, who are eager and excited to do it.  Sounder was far from eager and excited, there’s very little about his demeanor anyone could call feminine, and he was so nervous about it not looking good, that may have translated into perceived reluctance to get it done.

Oh, well.  So she wasn’t the humiliatrix I’d hoped she’d be.

Less than an hour later, she stepped back and asked Sounder what he thought.  He turned to me, and I couldn’t stop smiling.

He looked pretty.  Downright pretty.

But I knew he was dying in that dress.  So we grabbed our things together and got in the car, where I turned up the ac as high as it would go.

Still, I couldn’t help but pull up his dress in the car and stroke him through his panties.  I drive an SUV, and he pulled his dress back down when we pulled up at a stop light next to another SUV.

“High car,” he said, pointing out that they could look over and see us clearly.

I took my hand away, patting his leg.  “Alright.  But it’ll just look like I’m fingering my girlfriend.”

We got back to his place and I let him take the wig and the dress off.  He hesitated at taking the wig off, because he didn’t want me to feel cheated out of the experience.  But I assured him that I was happy, that he’d be wearing the wig plenty, and right then I was more concerned about him not passing out from heat stroke before I had the chance to completely abuse and degrade him.

And actually, his makeup looked even better without the wig.  Multiple times throughout the afternoon, I’d look at him and just be struck by how much younger he looked.  But the wig aged him.  She had styled it in a way that made him look older.

We’ll have to fix that for next time.

He changed into his pretty, 50s housewife dress and a pair of more comfortable heels.  After pouring another glass of wine for each of us, he went to work in the kitchen, fixing us something to eat.

You know, like a good little housewife.

I didn’t realize that he hadn’t even looked at himself yet, until he’d had a chance to cool down and relax, and we put the wig back on.

The eyebrow wax had come off a bit, but the makeup lady had warned us that was possible if he got too hot.  And I couldn’t fix it.

But even with that, he looked pretty.  He walked down the hall to his bathroom, and came back a moment later.

“I think, as long as we can fix the eyebrows, I’d be comfortable going out in public like this.”

Which seriously made my week.  “Really?” I asked, smiling like a crazy person.

“Are you serious?  I look like a completely different person.”

“You look good.”

“It looks better than I thought it would.”

I was still grinning like an idiot, and shamelessly gloating.  “I told you that you’d look amazing.”

“I just didn’t want to think that anyone could be better than you at anything.”


He can be pretty damn smooth sometimes.

But hell yeah she was better at it than I am.  She does offer a tutorial session, though, and that’s going to be the next appointment.  I’m going to learn how to do that.

And, of course, Sounder is going to learn how to do it.  Every girl needs to know how to do her own makeup.

My phone went off, and I looked down to see a text from Kazander.

“He’ll be here in about twenty minutes,” I told Sounder.

Sounder nodded, immediately downing the rest of his wine.  I laughed.

“That’s still not going to help you.”

“It’s going to try.”

To be continued…..

Overwhelming Sounder

Thursday night I went over to Sounder’s house, with a couple of different goals in mind.

First, I wanted to do his full makeup.  I finally had all the supplies I’d need, and I was looking forward to getting him all nice and pretty.

I got to his house and we spent a few minutes chatting, as we always do.  I asked him if he was ready to become a pretty girl, and he responded by taking a long sip of his drink.

I told him not to worry, that I’d make him pretty enough that a man wouldn’t kick him out of bed, and he gave me this look that said, “Yeah, you’re not helping.”

It was great.

So we went upstairs to the bathroom, he sat down on a chair, and I got to work.  I started with a super-white highlighter, because he’s pale, and went through all the contouring.  Other than the contrast needing to be just a smidge darker, I was really happy with the way the contouring looked.  It softened up his features and made his cheeks and jaw look way more feminine.

I could definitely work with that.

The eyebrows weren’t bad, either.  I didn’t use enough glue (it’s been a long time since I’ve done MtF makeup) so it looked a little “messy,” but that’s an easy fix for next time.  He keeps his eyebrows very well-groomed, as well, which helps.  It’s just one of those things that I’m rusty on, and will need practice.  Lots and lots and lots of practice.

The same with the liquid eyeliner.  I always go for the pin-up look on myself, so winged eyeliner is something that I’m good at — on myself.  I discovered that doing it on someone else is a whole different skill.  And one I’ll need to practice.

But it was fun.  He was sitting there, naked (because really, he just looks better naked), his little clit swollen and dripping.

It took awhile, but I finished his makeup, put his wig on, and his dress, and he just looked so cute.  I couldn’t help it, I immediately bent him over and started playing with his hole.

“Do you want your pussy fucked, little girl?” I asked him, fingering him and playing with his prostate.


“Yes, what?”

“Yes, I want to be fucked.”

He was so cute, and trying so hard not to say it.  But he knows me better than that.

What do you want?”

“Yes, I want my pussy fucked.”

Such a good girl.

I pulled out one of my dildos lubed it up and pushed it into him, kneeling between his legs as he lied on his stomach on the bed, moaning and squirming while I fucked him.

I fucked him for awhile, until it started to hurt, and then I put the dildo away.  There was another goal I had in mind, something else I wanted to do to him.

I’d asked him once what felt good to him, if there were certain parts of his body that were sensitive, certain places that he loved being touched/licked/bitten, and he didn’t really have much of an answer.  His nipples are crazy sensitive, but that’s the only real answer he had.

I got the impression that no one had really spent a lot of time exploring his body, really getting to know it.  He confirmed that when I asked him, and I decided that needed to change.

I told him days previous that I could completely overwhelm and overstimulate him without causing pain at all, that I could make pleasure just as intense (if not more so) than pain.

He said he trusted me, but I wondered if he thought I was kidding or perhaps exaggerating.  I was determined to show him just a hint of what I can do, what I’m capable of, and how relentless I can be.

So I took the dress and the wig off of him and had him lie down on his back, completely naked, and started running my fingers lightly over his body, watching him for reactions, to learn what felt good.  It didn’t take long to learn that he liked when I trailed the tips of my fingers over the backs of his thighs, up towards his butt, and I had him turn to lie on his side so I could access that spot better.

Lying on my side behind him, I was in the perfect position to test out how he liked having his neck played with.  I nibbled the back on his neck, and when he gasped and flinched, I knew I’d hit a spot that would be insanely fun to play with.

And really, he squirmed so nicely.  I paid attention to his body language, his reactions, and his voice, and used that to find the spots that I knew would send chill after chill after chill down his spine.

Before long, it “started” to get overwhelming, and he couldn’t help himself anymore.  He tried to squirm away from me, he tried to push his head to the side to keep me from reaching his neck, he tried turning his body, anything he could to get me to stop.

Silly boy, he knows better.  I wrapped my arms around him, holding him against me, and kept going.  Occasionally I would move to his ear, which wasn’t quite as sensitive, to give him a bit of a breather.

It wasn’t long after that I began to notice a change in his voice.  Normally, his tone doesn’t change much when I’m using him.  He’s always been very vocal, but his voice doesn’t usually get higher, like I’ve seen with many submissive men.

That started to change, the longer I played with his neck.  His voice got higher, and I heard the first adorable little whimpers and whines out of him.

Which, of course, did nothing but fuel my desire and make me want to do it even longer.

He was rock-hard, harder than I’d ever seen him before, and for much, much longer than I’d seen him before.  I would reach back down to caress his thighs and butt, and he’d gasp and writhe.  I’d reach down and grip his dick, and he’d automatically start thrusting, grinding and pumping into my hand.  I’m not even sure it was a conscious decision, I think it was more a reaction to being touched there at that point.

The longer I went on, the more he tried to squirm away.  At one point, he’d turned all the way over, so he was lying on his stomach, his head almost hanging off the edge of the bed.  I was lying beside him, and threw my leg over him, straddling him and using my weight to pin him down.

He’s a strong boy.  He would push up against the bed, basically doing push-ups and lifting us both.  I grabbed the edge of the bed, pulling myself down as he was pushing up, but goddamn he is strong.

At one point he pushed up onto his knees, lifting my entire body completely off the bed.  I laughed.

“Do you really think that’s going to make me stop?”  I asked.

He didn’t answer — I don’t think he could, but soon he lied back on his stomach, still gasping, moaning, and whimpering.

I have no idea how long I’d been doing it when I finally stopped.  I’ll have to ask if he knows.  I’m guessing it had to be at least half an hour.  Probably a lot longer.

I finally stopped, lifting myself off of him and lying beside him, running my fingers gently up and down his back while he recovered.  For a few moments, he just lied there panting, still writhing just a little.

Finally, he took a deep breath and sighed.  I grinned.  “Did you think I was kidding about overwhelming you without hurting you?” I asked as he turned over.

“I didn’t think you were kidding, but I didn’t expect that.”

When he turned over to lie on his back, I grinned when I saw that he was still rock-hard.

It had been a while since I’d let him cum, so I told him that I wanted to watch him jerk off.  He obediently began stroking himself while I watched, and when he came, he made quite a mess.  I was planning on making him eat it (he’s never tasted his cum, or even his precum, before), but took pity on him, and decided to give him something to look forward to next time.  I’d already put the poor boy through enough.

I let him clean himself up and get dressed, and we went downstairs.  I was stunned when I looked at the clock and saw that it was 11:30.  He had to work the next day, so I grabbed my things, he walked me to my car, and I left.

It was a lot of fun.  And I’m still not done exploring his body and finding all the little spots that feel good and can help me overwhelm him.  Next time, I think I’m going to do it again, but I’m going to fuck him while I do it.