Just a tiny little pill…

It’s almost comically small.  Tiny, white, nondescript, completely innocuous.

So why has Sounder been freaking the fuck out about it for the last three days?

Because that tiny, harmless-looking pill is going to change his life forever.

As in permanently.

It’s never been a secret that I want to feminize him and turn him into a sissy.  And it’s never been a secret that I love a good mind fuck (I mean, we have met, right?).

So I had an appointment with my internist today, and I’d decided that I was going to get a prescription for birth control.

Ohhhh, but not for me.  I don’t need birth control.  I haven’t had sex in… God, I don’t even know how long.  2 years?  3?  I don’t plan on breaking that streak anytime soon.  I’ve always found PIV sex to be boring.

But you want to know what’s not boring?  Turning Sounder into a full-on, permanent sissy whore.

And really, it started off as a passing comment, made almost half-jokingly.  But it triggered a reaction, and created an opportunity that I just had to take advantage of.

had to.  It was a moral imperative.

So all week, I’ve been fucking with his head, making absolute-damn-sure to drive home the fact that he will never be the same again.  After he takes the pill, after the hormones start taking effect, his body will forever be feminized.  Sure, some of the effects might go away if he were to stop taking them, and the progestin stops interfering with his testosterone.

But most effects, like the womanly hips and the boobs, will be there to stay.  From what I read, the effects on the penis and testicles will be mostly-permanent, too.

So some of the possible side effects:

The growth of breast tissue (the biggest reason for putting him on birth control in the first place).

The change in the distribution of fat cells, giving him those soft curves, that feminine figure.  Some men with very few fat cells to begin with will gain a bit of weight as their bodies create those curves.  He has very few fat cells (which makes putting a zipper on him impossible, ugh) so he’ll likely be in that group.

Changes in skin and hair growth.  Body hair will get thinner, finer.  Facial hair will also get thinner.  But the hair on his head may actually start growing more, and getting longer.

Changes in voice.  Some men’s voices get higher.  Sounder is a deep baritone (for now), so it’s likely that it’ll get higher.

Decrease in the size of penis/testicles.  Depending on the interaction between the progestin and testosterone, erectile dysfunction is a possibility, as well.  I have no use for Sounder’s cock, so I don’t need it to function.  It’s eventually going to be stuffed in a chastity cage, anyway.  And when that happens, he’ll be grateful for the erectile dysfunction, because he won’t have to deal with the pain of trying to get hard in the cage (see?  I’m thinking of his comfort here).

And hey, there’s a decreased risk of testicular cancer, prostate cancer, and prostate enlargement.  So it’s super beneficial, right?  It’s all medical and science-y and shit.

So yeah, the last few days have been spent constantly fucking with Sounder’s head.  Pointing out that, once he has tits, he’ll never be able to have normal sex with a vanilla woman again.  Even if his dick still worked, how would he explain the tits?

Although I imagine it would be a lot of fun to bend him over, fuck him doggy-style, and reach around to grope them.  Or having him ride my strap-on, his tits bouncing as he impales himself on my cock.  And I bet a lot of men would agree with me.  Have you seen how popular that fetish is?

So his sex life wouldn’t disappear altogether.

Ooooh!  And I’m so looking forward to taking him to get fitted and buy his first bra.  Because of course I’m not going to let him buy that online.  A girl’s first bra is a significant experience.  And besides, something like 85% of women are wearing the wrong size bra.  He needs to be professionally fitted.

We’re going to gloss over the fact that I know how to measure that and could do so in the privacy of his house.

Because good fucking gawd, why would I do that?  When taking him to Victoria’s Secret, getting him fitted, shopping for bras, and having him try them on in the dressing room is an available option?

Seriously, it’s like people don’t know me at all….

I did find some nice push-up bras to accentuate his cleavage.  I’ll have to wax his chest hair, though.  Hairy cleavage isn’t sexy.  But that’s something I’m more than happy to do myself, in the privacy of his house.  *Evil grin*

And of course, he’ll need to get mammograms.  Because more breast tissue equals a higher risk for breast cancer, and he just turned 40 (and if you remember Pinktober, all women and sissies 40 and older need mammograms) and really I would just love to take him to that appointment.  I’d give up my left tit to watch all that go down.

Luckily, I have an obedient little sissy, and won’t have to give up anything.  I’ll just go with him.

And I love the idea of going to a spa with him, but all the ones I know of are not co-ed, and trying to pass him off as a woman would’ve been difficult.  But with a more feminine voice, a more feminine body, and breasts, it shouldn’t be too difficult.

At least I’m being nice and letting him dress as a man the first time I take him to the salon.  He’s never gotten a pedicure or manicure before, and it’s not uncommon at all for people to get couple’s mani-pedis, so no one would think twice about it.

Unless I decided to say something about it, of course…..

But he’s already nervous about going in the first place, because for some reason he thinks it’s “weird” or whatever for a man to go to a salon.  And when I take him to get his wig professionally styled, that’ll be nerve-racking in itself.  So I’ll shock the ever-living fuck out of him and won’t fuck with him the first time I take him.

No, like genuinely.  I’ll be nice, I swear (Stop that.  I can practically see you raising your eyebrows and doing that nod-and-smile thing you do).

The second time I take him will be a completely different story.  And that’ll be an adventure.

But really, it’ll be awesome.  And tomorrow, when he goes to work, he’ll get to sit in all those important meetings with all those important people, knowing that the tiny white little pill is coursing through his system, silently killing his manhood.

Seriously, that’s so many kinds of fucking awesome.  Like, multiple levels of awesome.

And another bright side is that he’ll look even more sexy in all his women’s clothes.  Which he definitely needs more of.  Yay, shopping!

Eventually, the vast majority of the clothes he owns will be women’s clothes.  Sure, he’ll have the suits for work, and all that, but most of what he’ll wear will be women’s.

Because really, how big of a difference is there between a woman’s T-shirt and a men’s?  Jeans?  Pants, slacks?

Not that much.  I’ll probably allow him to have a few pairs of men’s shorts, though, because it gets to be 120 degrees here in the summer, and there is a big difference between men’s shorts and women’s shorts.  So when he goes out dressed as a man, he’ll have a couple of pairs.

Oooooh, it’s going to be swimsuit season soon!  I need to take him shopping for a bathing suit!  He’s got an amazing body, so you know I’m going to want him in a little bikini.  I mean, there’s just no question.  I wonder if his complex has a pool….

So he’ll have a couple of pairs of men’s shorts, some random men’s things here and there, for when family or friends are in town and stay with him, and his work clothes, but the vast majority of clothing he owns will be women’s.  All of his lounge-around-the-house clothing will be women’s.  Yoga pants, or cute bootie shorts, with tight little tank tops, or loose, flowy nightgowns.  Lots of options.

Eventually he’s going to live 24/7 as a sissy.  And taking that tiny little pill makes that goal all the more real.

So that’s the extraordinarily abridged version of what’s been going through his head the last few days.  And I made damn sure that it was never far from his mind for long.

I went to the doctor and got a prescription for a 2-month supply.  That’s all he would give me, and he was reluctant to do even that, since I haven’t been to my gynecologist in forever (because it’s a pain in the ass with a 4-year-old, and it’s a pain in the ass without a 4-year-old, and I just don’t wanna go.  Oh, but I will definitely put up with the pain in the ass for a year-long prescription of tiny little pills).

That’s the awesome thing about an internist, though, and the reason I use an internist as my primary-care physician.  There’s literally nothing he can’t prescribe if you’re really persuasive.  Antidepressants, birth control, Adderall (you know, speed, but legal, if you have ADD….. or are really persuasive), you name it, I can get my hands on it.

Yay, drugs!

But it works, because it’ll give us two months to try out the low-dose pills I got, and see how we (we meaning I) like them.  If necessary, I’ll get something different when I go see my gyno in May.

So I got the prescription and asked Sounder what pharmacy he uses.  I wanted it to be one by his house, because he’ll be the one to pick up the refills (because I just love the idea of him going to pick them up.  It’s unfortunate that I can’t put them in his name.  Or the sissy name I’ve given him.  That makes me sad.  But don’t worry, thinking about him having to pack them on his carry-on when he travels for work this week makes me happy again).

He was hoping and praying for something to go wrong.  Either I wouldn’t be able to get the prescription (it made me smile and go, “aww,” when he hoped that I wouldn’t be able to talk someone into giving me something I want… I never claimed to not be manipulative, y’all), or the pharmacy wouldn’t have them in stock, or the pharmacy would burn down (which is my line).

But everything went smoothly, and I showed up at his door with the pills in hand.

And they really do look so small and innocent.  It’s amazing to think about the drastic effect such a small, tiny little thing can have.

I could tell he was freaking out, really not wanting to do it.

But when I told him to strip down to his panties, his dick was hard.  So at least some part of him wanted it.

I was nice, though.  I didn’t hold it over him for that long.  I gave him the pill, and he took it, and just like that, he said goodbye to being able to call himself a man.

So I’m excited about it.  Every aspect of it is awesome, and hot as fuck.  And really, he’s such a sexy sissy.  It wouldn’t surprise me if the pharmacy starts assuming he’s Jennifer when he goes to pick up the refills.

Oh my gawd, how awesome would that be?  He’d go up to the counter, to the little pharmacy tech, and say, “I’m picking up for Jennifer ——.”

And the sweet little tech could say, “Sure, Ms. ——-.  I’ll get that for you right away.”

I seriously just squealed like a ten-year-old girl.  That would be beyond epic.  Like, epically beyond epic.

But as much as it’s fucking with his head now, eventually picking them up will become a regular errand, just another part of his routine.  Just like taking the pills will become just another part of his routine.

Some people take vitamins.  Sounder takes estrogen.

Because he’s a sissy.

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.

“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.”


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?”


“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.


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.