It’s pink!

So, as I may have alluded to previously, I recently got to do some amazingly fun, super awesome shopping for my darling sissy slut.

And I picked out the loveliest of lacy pink bedsets, and eagerly awaited the delivery.

The original plan was to not tell him when it got in, and go to his house while he was at work, set it all up on his bed, then leave so he’d never know I was there.  He’d come home, just like any other day, and walk into his room to see it there waiting for him.

He’d know it was coming, of course.  I mean, I’ve only been talking about it for weeks.  Of course he knew it was coming.

But he didn’t know when.  So it would be a fantastic mindfuck.  Not only would there be the shock of the bed itself, but also everything it represents.  It’s the first step in sissifying his entire house, I’ll have him gangbanged on it, when he sucks his friend’s cock, it’ll be on it, every night it’ll be the last thought he has, and every morning it’ll be the first.

That was the plan.  And it was a good plan.  I liked the plan.

However, there’s something about me that my subs know, but my readers likely don’t.

I am a total child when I’m excited about something.

In a good way, mind you.

“Giddy” is definitely an accurate descriptor.  And, for as much as I work to cultivate my super-intimidating-totally-terrifying-evil-bitch persona, “giggly” is just as accurate.  I have literally been known to squeal like a little girl at a Justin Bieber concert (is he still a thing?  Or is that reference obsolete?  Nevermind, I don’t care).

And this applies to every part of my life.  For example, I think there’s been once that I’ve managed to wait until the appropriate gift giving occasion to give something I was excited to give.  And I realized early I had to give Kazander the authority to keep me from giving the spawn her Christmas/birthday/whatever presents early.

Waiting for a particular date or something is easier, because there’s nothing I can do.  I’m excited to go to Cancun this fall, but it’s easy to wait because I can’t just up and go earlier.

Dates are easy.  Things are hard.  Secrets are hard.

Seriously, I’m like a kid on Christmas morning.  Total child.

And I’ve been beyond freaking excited about the bed.  I was checking the tracking info like every twenty minutes.

When it finally got in, I tore into it immediately, saw how unbelievably pretty it was in person, and my excitement went through the roof.

Christmas morning and Justin Bieber concert all rolled into one.

And I couldn’t wait.  I told Sounder right then that it had gotten in.

And man, it is pink.  My sister in law saw it as I put it in the washing machine and said, “What is that?  That is really, really pink.”

Which, naturally, I had to relay to Sounder.

I went to his house with the bedset in the original bag it came in (but I’d taken the picture and label off.  I didn’t want him seeing what it looked like).  Even though I couldn’t keep the surprise, I still wasn’t going to let him see it until it was all set up and beautiful.

I took it upstairs, told him to stay downstairs, and stripped his bed.  And began the thoroughly enjoyable process of transforming his bed from something any masculine man would feel comfortable sleeping in to something indescribably pink, frilly, lacy, and delightfully feminine.

And I’m usually not a perfectionist, but I certainly was that night.  I wanted every pillow perfectly placed, every piece of lace trim meticulously positioned, every detail just so.

So that when he walked in, and saw it for the first time, the image would be forever seared into his mind.

I think I achieved that goal.  Truly, it was spectacular.  I was beaming when I finally told him he could come up, and I watched him walk (much more slowly than he usually walks) into the bedroom.

He looked at it, sitting there in all its pink glory, then took a deep breath and said, “Yeah, that’s worse than I expected.”

I think I squealed out loud.  I know I definitely did in my head.

And he, being the sweet, obedient bitch that he is, picked out a new lingerie outfit to commemorate his new bed.  Something pink and frilly and equally humiliating to match the bed.

So he put it on, and goddamn, it was so fucking hot.  It was definitely the most feminine, delicate, girly thing I’ve seen him in.

And he picked it out all by himself.

Or, perhaps more accurately, herself.

It was time to christen the new sissy bed.  I put him on all fours in the center of the bed, his back arched and his boy pussy out and ready.  It was an incredible view.

I didn’t waste any time, and slid a big cock in him.  His soft moans were so cute as I fucked him.  And then he came with my cock in his ass and his face pressed down in the pink sheets.

It wasn’t my strapon, though.  I didn’t touch him at all as I fucked him.  The only sensations he felt were the the pink bedset under him, the soft lingerie against his skin, and the cock inside him.

And he came, hard and often, like a horny little slut.

Then, when his ass was raw and throbbing, I fingered him to a couple more, grinning as he squirmed and writhed on the bed.

It was every bit as hot and humiliating as I wanted it to be.  And now he has a gorgeous sissy bed.  And I can’t wait to take the next step in sissifying his entire house.

One hell of a surprise

You know what’s really funny?  Scheduling a post to upload, and completely forgetting about it (including forgetting to finish it) until you see all the email notifications the next morning.  I’ve been a bit scatterbrained.

In other news, I’m out of Asheville and made the trip back to the bustling metropolis of Kernersville, North Carolina (population: 24,000).  But there’s reliable internet and air conditioning, and it’s reasonable to assume that, staying indoors, I’m safe from mosquitos and bugs eating me alive in the night.  So now I’m playing catch-up.  If you’re waiting for communication from me, I promise it’s coming.  Before I go to sleep tonight.

Yesterday was intense as fuck, and by the time I made it back to civilization, my first instinct was to find a way to get myself centered and balanced again.

I don’t know if any of you are aware of this, but there’s this adorable, awesome sissy I own, who is all kinds of awesomely awesome awesomeness.  From the very first text he sent me after I told him I’d finally finished with the hippies and was heading to a hotel for the night, he made me smile.

Before losing touch with technology, I’d given him an assignment.  I wanted him to fuck himself, and I wanted pictures.

This isn’t a unique assignment, I often have him do it.  I love the idea of something filling him up, and I’m a very visual person, and I love looking at porn.  So it’s not unusual for me to want pictures of my boys.  My very own personal porn stash, made just for me.

And Sounder has been fighting a cold, and wasn’t 100%, so I knew the pic(s) he sent me would be on the more mild side.

But hell, I wasn’t going to complain.  He’s fucking hawt, and seeing pictures of him naked or in lingerie, with something sticking out of him, never fails to make me happy.

I asked him about the pictures, and he told me that yes, he’d taken them, and asked if I was in a safe place for them.

Which immediately caused me to raise a brow.  He’d never asked that before.  But I shrugged that thought off and told him that I was alone-ish (my kid was in the room with me, but she was otherwise occupied), and that he could send them.

Over the next five minutes, my phone went off 9 times.  And literally, all I could do was sit there, staring at my screen, stunned, my jaw dropped.  I’m pretty sure I was drooling at some point.

Like, holyfuckingshit.

No, seriously, like holy.  fucking.  shit.

Three different toys, one outfit change, in three different rooms of his house.  Like, oh my gawd.

And every one was unbelievably fucking hot.  Like, I want to get them printed and frame these fucking things.

You guys don’t understand.  He even wore the bra I’d left him in one of the pictures.  Two pictures of him plugged, one of him sucking his massive dildo, three of him either on all fours or on his back, fucking himself with a slender blue vibe, and three of him squatting on the floor, fucking himself with the massive dildo, that was attached to the floor with the suction cup on the end (he told me that, because of the size, it’s much easier to manage when he can attach it to something and fuck himself that way, rather than using his hand to push it in).

It was beyond hot.  Like, holyfuckingshit.

He said, “I’m glad you like them, I figured you might need a distraction so I went a bit overboard.”

While he was still fighting a cold.

No seriously, I fucking love this girl.

The first picture he sent, one of the ones of him plugged, he told me he’d be comfortable with me sharing, as long as I blurred the background beyond recognition.

 

2016-08-07_20.45.16

Yay!!!!!

I love everything about it.  I love the way his back is arched, the way his ass sticks out, the way his posture accentuates his feminine curves, the way his hair (which he curled, himself) tumbles down his back, the way the plug peeks out from inside him, the contrast of the black lingerie against his pale, smooth skin (that I immediately want to bruise and mark up, as soon as I see it).

Jesus, there is nothing about this sissy that doesn’t just ooze fuckability.  No one would ever kick him out of bed.

This was the first picture he sent me, and as soon as I saw it, all I could do was suck my breath in a little and murmur under my breath, “Oh, Goddamn…”

So I know the position he’ll be in next time I fuck him.

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…..

Pretty little housewife

With scheduling conflicts and illnesses making for annoying obstacles, it’s been a long time since I’ve been able to spend some time with Sounder.  Tonight, that changed.

And man, I was feeling sadistic, the poor boy.

After a glass of wine, I told him to take his clothes off, and noticed that his chest was red.  He explained that he’d waxed earlier, and didn’t expect it to react that much.

It’s only the second time he’s ever been waxed, so the reaction wasn’t surprising.  Still, I need to get a new wax kit of my own here soon, and I’ll look and see if I can find anything for sensitive skin.  Maybe that’ll help.

The really fun part, though, was just how sensitive the whole area was.  I reached out to touch him super softly, and he flinched away.

That hurts?” I asked.

“Yeah.”

I grinned.  Oooh, this would be fun.

Oh, and as it turns out, my nails, which I usually keep short, were much longer than usual.  So running my nails across his chest was a lot of fun, and his reactions were so cute.  He squirmed and gasped so nicely.

I love bending him over the island in his kitchen and groping him.  It’s a lot of fun, and he makes the most adorable sounds.  Some pleasure, mixed with some pain, and he’s basically (to quote him) a puppy dressed as a baby duck.  It’s that cute.

We went upstairs, and I saw his new dress lying on the bed.  He hadn’t tried it on yet, and I was so excited to see it on him.

And he looks awesome in it.  It’s a lovely retro, pin-up style dress, pink with black polka dots with a halter top.  It’s so cute, and he looks so good in it.  I think I like it even more than the sexy black bodycon dress he has.

After putting the dress on, I told him to put his makeup on, and we both noticed that the makeup looked off.

“I look like Skeletor,” he said.

“You’ve been out in the sun, haven’t you?”

“Well, it is 130 degrees out.”

Pfft.  I don’t even think it cracked 110 today.  But he’s gotten tan.  The foundation is too pale for him.

So I know what shade he needs, and I’ll pick that up.  But we made do with what we had, and he continued putting it on, while I lifted up the dress and set about seeing how well he could keep his focus while being teased, stroked, and fingered.

His reactions were beyond adorable, and as it turns out, fingering him is enough to shatter his focus.  Which, of course, is one of those incredibly useful bits of information that you just store away for some particular scenario that may or may not happen in the future.

No, there’s nothing ominous about that at all.

I made him wear a wig earlier in the day, and he mentioned how hot it was, so I let him go without.  He looked cute enough without it.

But here’s the thing.  I’ve always loved pin-up clothes, makeup, and hair.  Whenever I go out, that’s my own preferred style.  And I think Sounder would look amazing with that style.

He mentioned wanting to cook me dinner, and that’s immediately where my mind went.  He would look so cute in the kitchen, wearing that dress with a retro, frilly apron, with the full pin-up hair and makeup.  Just like a 50’s housewife.

My darling little housewife.  He’d cook for me, and then I’d bend him over the sink while he’s doing the dishes and fuck him raw.  That’s a fabulous idea.

Speaking of fucking him raw, I sure did that tonight.  The poor boy hasn’t been fucked in so long, and his pussy was so tight, I could barely get my cock inside him.  He’ll make whatever man I give/sell his virginity to very happy.

But really, it was the pain I was the most interested in.  And I love how hard he gets whenever I hurt him, I love how he squirms, how he gasps, I love his facial expressions when I hurt him, I love making him scream.

So I backed him into the corner and turned my attention to his nipples and his chest, and I think it’s safe to assume he’s not a fan of me having long nails, particularly when his skin is red and irritated.

Oh, but it was sooo much fun.

Then I told him to lie down.  I took out my wand, plugged it in, and held it against his clit, stroking it, teasing it until it was ultra sensitive, then torturing him with it.

Which is always fun.  And he’s so cute when he begs me to stop.  Really, lots of cuteness all around.

I had to laugh, though.  When I finally stopped with the wand, after, I dunno, maybe half an hour (he still can’t cum like a man), I started pinching and twisting his dick, and didn’t get a reaction.

“Really?” I asked.  “Nothing?”

“Oh, that is so much better,” he replied.  I had to laugh.  He prefers being hurt to being pleasured.  He was completely soft almost the entire time I pleasured him, but it sprang to life when I started hurting it.

So between that, and not being able to cum, vanilla sex is pretty much out of the question.

Oh darn, poor thing.  I guess he’ll just have to get his pleasure from being fucked like the little bitch he is.  Like a pretty little housewife.

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.

 

untitled

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.

Sounder Speaks – A guest post written by the sissy

As Domina Jen said, “just a tiny little pill.”  Not only was this the title of the blog post I had feared was inevitable, but it was representative of how the past several months have gone.  Feminization was never something I had expected, nor was it something I even knew much about, but it started in this same “just a….” fashion and before I knew it I was popping a tiny little pill out on its corresponding day and swallowing it down with a daily vitamin.

“Just a pair of panties” turned into “no more men’s underwear,” while “just try this dress on” evolved into “with the exception of work, women’s clothes only.”  The well-timed texts of “sweet girl,” which seemed playful enough given the physiological impossibility of that truly applying, were soon replaced by the tiny little word of “sissy.”  The realization struck hard; there were no physiological barricades to that title actually applying.

Playful left the building on that infamous night She handed me that first pill.  All of the side effects, which She was kind enough to detail at great lengths, seemed to pale in comparison to the one vision of that small white pill between Her finger and thumb.  All of the tangible fears couldn’t hold a match to what the first pill represented.  Understandably that must sound illogical, but I knew once that bridge was crossed and pill #1 was dissolving in my stomach it would follow in the footsteps of every other step.

As I suspected, minutes after pill #2 began working its way through my system, the fear transitioned to something far more puzzling for someone who had not imagined feminization: “Shit, what if this doesn’t work?”  You see, I don’t like failing at anything, and when you add the additional layer of detecting the enthusiasm Domina Jen had for the process, I began hoping for the results to be even more significant than the details She had used to scare me.

As of this writing, twenty-four hours have passed since Domina Jen studied and prodded me until She confirmed what I had thought, that the pills actually are working.  It was a relief, but it was also a realization that all of the texts that had haunted my mind were going to come true in due time as well.  Then, of course, there was the task that leads us here; after realizing how easily flustered I became when She updated me as to how many people had read the tiny pill post, naturally the next step was to ask me to contribute to the blog as a follow up to the very post that had crushed my nerves just days ago.

No matter what I have prepared for in my head, Domina Jen has a keen ability to take a difficult situation and morph it into something far more unfathomable.  For those of you who have been regular readers to this blog you know of Her requirement that Her perspective boys partake in a bisexual activity.  Now, it is not my “thing,” but I have engaged in it before so I wasn’t all that intimidated by it.  Sensing that, She made the declaration that my particular action would involve the additional layer of doing so while dressed as a sissy.

The buildup to that moment was a level of fear that my body had never encountered before.  Of course, detecting this, She was kind enough to regularly check in to let me know just how many hours I had remaining until it happened.  I’m a very self-aware person and I could feel the trembles, and I was fully aware that I was grasping for and fumbling over words as She applied the makeup to me.  None of that compared to the moment She left me standing alone in the room as She went to retrieve Kazander.  As I stood there staring at the ground listening to every step outside the room my head felt like it was a reflection in a magnifying glass while my stomach was enduring an extreme, never-ending descent on a roller coaster.  Right up until the moment She pressed his cock into my mouth , and I realized it was no longer about me.  That was what She wanted, and knowing She was not going to allow me off easy drove me to meet Her challenge and deliver what She wanted to the best of my ability.

So She continues to increase the pitch on the face of each mountain She leads me up, only to watch me step off the cliff once my mind reaches the plateau.  As She has mentioned, Her next desire is to up the wager on the bisexual action to full-on being fucked; well, truth be told, Her preferred picture to paint for me is being fucked by 4-5 men during one time.  Some of you can probably understand the terror in hearing the cliff notes version of conversations She has as She actively recruits the 4-5 men.  She has me so paranoid of the event that I literally pace in front of my windows waiting to catch a glimpse of Her car pulling up the driveway, hoping to see only one head in the car.

There is an important distinction between stepping off a cliff and being pushed.  None of this has been against my will; this isn’t 1492 after all.  We have crossed lines that I didn’t know I had, simply because I never imagined these lines ever being in front of me.  As has been alluded to here, I’ve been dealing with a perfect storm of health issues that have minimized my ability to withstand the type of kink my world had been centered on.  Although some more “balanced” people would disagree, by opening the door to this new world, Domina Jen has actually done an amazing thing for me.  She gave me something to embrace and dedicate myself to, that injuries really do not preclude my fullest participation.

That is not to say that it hasn’t turned my mind inside out, and that I don’t lie awake at night staring at the ceiling, fearing what could come next.  But isn’t that one of the great facets of having a kinky lifestyle?  I have a Pavlovian response to the text message indicator on my phone, men’s underwear seems foreign, the porn I watch would make my former self blush and turn away. 

So one little pill has evolved into 15, a cock in the mouth is no longer good enough, shopping for men’s clothes is pretty much off limits, and “sissy” no longer stings.  The fears will continue to increase with each “ohhhh you know what….” text and I’ll continue to have the same approach to visiting this site as someone would while opening a pressurized can of Anthrax an inch away from their face.  But that is the path, and this is my role, and far be it from me to take it lightly.

 

Making Progress

I went over to Sounder’s today.  It’s been almost two weeks since he started taking the birth control, and I haven’t seen him in about a week, so I was excited to see if there were any noticeable effects yet.

I wasn’t really expecting much.  It is a low dose of hormones, and it hasn’t even been two weeks.  But I was cautiously optimistic.

As early as a few days after he started taking the pills, he talked about his cock not working as well.  Which was expected.  The estrogen would take awhile to build up in his body, but the progestin would start fucking with his testosterone almost immediately.

So he felt like there was definite shrinkage, as well as it not being able to get hard.  In fact, he mentioned that the only time he could get hard was when I would fuck with him via text.

And that’s a definite win.

He also mentioned the possibility of growth in his breasts, but because he sees it every day, he couldn’t be sure.  But he has gained 4 pounds in two weeks, so that certainly seemed promising.

So I pulled up to his house.  After chatting for awhile, I told him to take his clothes off.  He stripped down to his panties (sexy purple lacy ones), and I grinned.

Yes, there was definitely some growth there.  It was subtle, but there was a difference.

The big difference wasn’t so much the way they looked, but the way they felt.  Sure they were slightly bigger, and he said they felt heavy, but when I reached up to grab one, I was shocked at the difference.

Sounder is fit and athletic, with a sexy body.  In the past, when I’d touch his chest, I’d feel nothing but rock-hard muscle.  So it was an extremely pleasant surprise when I groped his tits and they were soft.  Just like a girl’s.

I spent some time playing with my fun new toys.  His nipples were still recovering from my abuse of them a week ago, so I was gentler than normal, but I just loved the way they felt.

I loved the way they moved when I touched them.  I loved the contrast between the hardness of his arms, shoulders, and abs, and the softness of his breasts.  After getting to know his body so well, it was a little odd to feel something so different, so quickly.  It was more than I expected, and I was beyond stoked.

It won’t be too long before I’ll need to take him to get his first bra.  Now that he has breasts, he’s got to take care of them.  I certainly don’t want them to start sagging.

Finally, I stepped back to look at the rest of his body, particularly at his waist and hips.  “I don’t really see any other differences,” I said, stepping around behind him.

“Well, those 4 pounds had to go somewhere,” he replied.

Again, it wasn’t so much about how his body looked, but how it felt.

I stood behind him, groping him, playing with his clit, running my hands along his body.  Then, I grabbed him by his hips, and immediately noticed a big difference.

Two weeks ago, his hips were lean and hard, just like the rest of him.  I would grab him, and I’d feel his hip bones.

Tonight was a completely different story.  They felt soft, just like his boobs, and there was probably a good half an inch extra there, giving him a more feminine, hourglass figure.  It wasn’t a big enough difference to see yet, but I could definitely feel it.  His hips had never been soft before.

And touching him there, exploring his new body, was so goddamn fun.  His butt looked a bit rounder, too.  A bit perkier.  I immediately wanted to hit it with things.

So, after touching him, stroking him, and fingering him for awhile, I told him to go upstairs, that I wanted him to put on his makeup.

And he’s really gotten good at it.  The only thing he needed help with was eyeliner, which is a massive pain in the ass even for people who have been wearing makeup for years (perfect example: I had to completely wipe mine off and start over twice tonight, and I’ve been wearing makeup 4-5 days a week for the last 15-ish years).

Oh!  But I found a woman here in town, a professional makeup artist specializing in mtf transformations.  I’m so excited, I am absolutely taking Sounder to see her.  I’m good with makeup, but I am not a professional, and I’ve only ever done mtf makeup on one other person, years ago.  Sounder could definitely benefit from an experienced professional.  And for an extra fee, she’ll teach us exactly how to do it, so we can recreate the look whenever.  I’m excited to make that happen.  And I think Sounder will be really surprised to see the difference between what a professional can do and what I can do.

Sure, he looks good when I do his makeup, or when I coach him how to do it.  But with a professional, he’ll look stunning.  I can’t wait.

So he did his makeup, then put on his wig and I just did a basic style, to keep it out of his face.  I need to take him to the salon to get the wig styled one of these days.

After that, he put on his sexy black lingerie, and I bent him over the bed and started spanking him.

I have a bullwhip, that I’ve had for a bajillion years, but haven’t been able to use in half a bajillion years.  I’m damn good with it, though.  My mentor taught me by setting up a row of dominoes on a table or bench, a couple of inches apart, with the different numbers on top, 1 through 6.

Then, he’d call out a number, and I needed to hit that domino, and only that domino.  At first, he started out easy, going in order from 1 to 6 or 6 to 1.  But then he’d make it harder, like wanting me to hit 2 and 4, then the odd numbers.

Still, he wouldn’t let me touch a person with the whip until I could do that consistently.

Which is awesome, and I’m grateful he did that, because it’s so much fun being able to do that.  I can hit the head of a man’s cock over and over and over again.

If I have enough room.  And while I technically can use it in Sounder’s bedroom, I have to stand right against the wall, which doesn’t give me the room to properly aim.

All the more reason to get a dragon tail!

I switched from that to my tawse, and then to the flogger.  And I really laid into him with the flogger.  For as light as it is, it can definitely pack a punch.

His ass was nice and red and warm by then, so I switched it up and fingered him, then fucked his ass with a dildo.

And really, y’all… He looks so cute, all dressed up, in makeup, with his sexy hips and even sexier tits, with a cock sticking out of his ass.  I seriously need to get him fucked by a real man.  Soon.

I haven’t really beaten anyone like that in awhile, and isn’t it weird how you forget how good something feels?  Especially with the flogger, I loved hitting him with it.

The rest of the world just melts away, and there’s nothing but that room, with me, my flogger, and the writhing boy beneath me.  There are no plans, no agendas, no goals, it’s just me beating on someone until they just can’t take any more.

It’s a seriously awesome feeling.

So I’m extremely happy with the effects of the birth control so far, and I am absolutely looking forward to watching his body continue to change.  When I’m done, he’ll be such a sweet, sexy, feminine sissy.