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.”

Awww……..

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…..

5 thoughts on “Sissy slut

  1. Ah.., such a teaser! Looking forward to a short wait till the next instalment!

  2. Yes, I agree. A very teasing ending!

  3. Chris says:

    Dear Jen, thank you so much for sharing your experiences! I absolutely admire your way of life, so to say, and your blog, I am a regular reader. What about the effects of the pills Sounder is/was(?) taking, any further progress?

    • Domina Jen says:

      Thank you for the kind words. Sounder is still taking the pills. Progress has seemed to hit a bit of a plateau, but I have an appointment soon to get new birth control, with a higher dose of hormones, so that should kick it up again.

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