Sissy Pill

Throwing my keys into a nearby bowl, I heave my work bag onto a kitchen stool.

“What a day!” I groan, rubbing my eyes.

All I’d been wanting to do since about lunchtime was to get home and put my feet up.

It wasn’t that today had been hard work. It’s just after five odd years slugging away in that bloody office, I’d really started to stagnate.

Nothing was really happening for me there and the management didn’t even care I existed!

Being Lazy, I throw in an oven pizza and ditch my work uniform. Walking around my empty apartment in my boxers, It was nice to be out of those tight pants

Once the pizza was done, I take it over and slouch on the sofa.

Inhale the pizza, and I also guzzle down a beer.

Wiping my mouth clean, I stretch and reach over for my laptop. Flicking it open, I place it on the arm of the chair.

Opening Youtube, I scroll past video after video, until I get bored and settle on any old thing.

With the video playing and my tired brain trying to take it all in, I feel my eyes begin to droop and become heavy.

Getting myself a little more comfortable, I wasn’t bothered if I fall asleep on the sofa.

I lived alone, so it wasn’t like anyone was going to catch me in just my boxers!

Just as my eyes droop, I click on another random video. Half asleep, I wasn’t even paying attention I’d clicked on.

Instantly creepy, but melodic music fills the room.

With the lights off, the laptop screen turns pink and bathes me in its glow.

“You love to please men…..,” the video gently announces.

Feeling super tired and confused, I wasn’t sure what I’d just heard.

I look up at the laptop screen to see a dark purple swirl spinning rhythmically.

“Stop holding back…..,” a strong female voice commands. “Give in to your real truth! Men are your world. They are your everything!”

Mesmerized by the swirling image, I just nod and agree with the commands said to me.

As images flash across the screen, I continue to just stare religiously at the screen and the strange video playing.

“Men want you,” the powerful female voice continues. “They crave you as much you crave them…..,”

Slowly nodding again in agreement, I allow my eyes to follow the swirling images.

“Let them take you….,” it commands. “You lust for them. You lust for their strong male attention.”

My mind is fixated on the screen. I couldn’t stop watching and listening to its sounds.

As the screen fades to black, the words ‘Sissypill.com’ echo around the room. Repeating again and again.

When the video ends and an advert appears on the screen, I snap out of my trance.

Looking around my dark apartment, I was so very confused.

Had I just been asleep the whole time?

“Argh,” I groan, looking at the time on my laptop. “I must have been asleep!”

So confused by what time It was, I violently shut my laptop and amble into the kitchen.

“I can’t believe it's one in the morning??” I whine, so confused about where my night went.

Scratching at my head, I shrug my shoulders. I guess I should go to bed.

Almost in a zombified state, I stumble my way into the bedroom. Throwing myself face-first onto the bed, I wrap myself up and allow my eyes to close.

The next thing I know, I’m waking up in a cold sweat. Super uncomfortable, I’ve got vague words and sounds repeating endlessly in my mind.

Tossing and turning, I keep hearing the words over and over again. It doesn’t stop!

Eventually, the nighttime becomes morning.

The sunrise streaming through my window ends my torturous night's sleep.

Reluctantly getting out of bed, I knew I had to get ready for work.

Looking into my bathroom mirror, I looked at my tired face and for some reason, my reflection seem wrong to me. It looked too masculine.

“Maybe it’s time to have a shave,” I comment, looking at my male face with disgust.

Other than feeling odd about my appearance, nothing else about my morning was out of the ordinary.

Once I’d gotten to work, I grabbed a strong coffee and got on with it.

Around midday, I started having more weird feelings and thoughts.

It started off with me wondering if I’d look good in heels, then It moved on to me lusting over my boss in his tight pants.

I knew something was really wrong when Stacey bent over in front of me. Usually, I’d be all over that, with her tight short skirt.

But like earlier with the heels, I found myself wondering if I’d look good in a skirt. Did I really want to wear something like that? I’m a guy, not a girl!?

As the day went on, the weird thoughts kept coming.

At one point Stacey came over to me and pointed out how feminine I was walking and sitting. She genuinely thought I was trying to take the piss.

I couldn’t have been more confused! Was I doing it on purpose?

That wasn’t the worst of it!

Every time Harry walked by, I hope he’d come over and give me attention. I’d been gawking at him like a horney teenage girl. I just couldn’t stop myself!

After a few agonizing hours, I got my wish.

“Brian,” Harry said with confidence.

His powerful voice was enough to make me jump right out of my office chair. My heart rate doubled!

Turning around excited he was finally talking to me, I swing around too quickly and  I end up on my knees directly in front of him.

Looking up, Harry’s sturdy frame towers over me.

“Are you ok?” he asks, looking down at me with a smile.

I’d never noticed before just how stunning his eyes are. Along with that rugged chin and perfect cheekbones.

With my head at the height of his crotch, I’d also never noticed how much he was packing. Trouser snake for sure!

“Yeah sure….,” I answer, desperately trying to shake my weird thoughts from my head. “What can I do for you, sir?”

 “Good,” he says holding a hand out to help me up.

As his powerful, yet soft hands take hold of mine, I found myself getting a little too excited.

“I need that report by the weekend,” Harry insists, helping me onto my feet.

Being very confused by my thoughts of attraction to him, I stare at him blankly. What the hell is going on with me!?

“Brain!?” he says, but this time more impatiently.”

Not knowing what he’d said to me, I knew I needed to response, and quick!

“I’d bend over for you sir!” I hastily answer, allowing my lust for him to control my tongue.

“Riiight,” Harry replies, giving me an awkward look.

Turning away and biting my lips, I wonder why on earth I just said that!? Why…bend me over!??

“Just get it done Brain,” Harry continues.

“No problem,” I answer, with my face going bright red.

Giving me another awkward smile, he turns and leaves.

Watching him walk away, I couldn’t help myself but stare at his arse. It was perfect, like to perfectly bake buns.

“Argh!” I moan, rubbing my face.

What the hell is wrong with me?. What's with these thoughts and why am I lusting after my boss!?

As the hours of the day continue to tick away, I do my best to hide away from everyone.

It’s like I’ve had a complete personality swap. I kept craving male attention and I wasn’t even sure why!

By the end of the day, I was totally exhausted.

Slowly making my way home, I slam the door behind me and curl up on the sofa.

Trying my best, I couldn’t get Harry out of my mind. I just felt like I needed him.

Giving in, I decide the best thing I can do Is distract myself.

Not finding any solace in TV, I end up cleaning my home.

Starting with the laundry, I end up standing in front of my wardrobe staring at the clothing left by my ex-wife.

It wasn’t a huge amount, but she’d left underwear, work clothes, and workout gear here.

Usually, I wouldn’t even notice the dresses hanging in my closet, but I felt compelled to look at them

I’d always meant to throw it all away, but the small lacey underwear had me massively intrigued.

Picking up the black lacey thong, I hold it against myself.

I wanted to know how it felt to wear it. I had to know!

Swiftly undressing from my work stuff, I stand in front of the length mirror buck naked.

Slipping the soft lacey underwear up my hideously hairy legs, I nestle myself into them.

The soft material felt great on my skin and loved the way the material rode up my backside.

Feeling pretty good about wearing lady's underwear, I wondered how far the rabbit hole went down. Pulling out one of my wife's old works dresses, I lay it down on the bed.

I knew it would fit me. My ex-wife was taller than me and somehow a little wider.

Looking back into the mirror, at my naked body in just lady's underwear, I sigh at the image.

“Brain!” I grumble at my reflection. “Look at all that gross hair! No wonder she left you!”

I honestly couldn’t believe how dirty I felt. How couldn’t believe how I’d let myself get so yucky!

Swiftly getting my disgusting body into the shower, I shaved my entire body smooth. So smooth, I hadn’t a hair on my body from below my eyebrows.

Honestly, as I step out of the shower, I can’t believe how much better I feel.

Instantly more confident in my appearance, I really understood the appeal. No wonder the ladies at my work loved having their legs out!

Once dry, I knew it was time for me to hit the sack. That was what my brain was telling me, but my ex-wife's dress lay on the bed. It was calling out for me to try it on!

Giving in to those urges, I quickly slip my ex-wife's underwear back on.

Feeling good about myself wearing her panties, I grab the matching bra.

Struggling to get it clasped up, I eventually get it on.

I loved how it felt around my back and across my chest.

Being a little tight, it squeezed my body as no other clothing had done before. I can’t believe how right it feels! If I was to take it off, I’d feel naked!

Looking into the mirror, a small part of me knew I shouldn’t have felt so good about what I’m wearing.

This wasn’t the case at all! I’d never been so excited!

“Love it!” I scream out, jumping on the spot.

Searching for my phone, I snap picture after picture of my reflection in the mirror.

Pulling more and more effeminate posses, I end up on all four on the bed.

With my phone on auto-timer, I push my ass up into the air toward the lens.

I hoped the camera would capture just how plump and sexy my behind looked in the lacey underwear.

Reviewing the photo, I couldn’t contain my excitement.

“Oh, my God!” I cry out. “I look so feminine!”

My ass looked massive and so do-able

I knew men would lust after such a picture and I felt so pleased about that.

So pleased in fact, I quickly made a new Instagram account.

Calling myself Smooth Stacey, I didn’t waste any time uploading posts of myself just in my ex-wife's underwear.

My favorite picture was me on all fours. I knew I wanted that as my profile picture and I didn’t even hesitate.

Within moments, likes and comments started flooding in.

Looking through the very positive comments, I couldn’t help but notice all of them from men.

Knowing I shouldn’t feel so happy about the attention I was getting from all these random men, I couldn’t stop myself!

“They love me!” I scream out, jumping up and down. “I can’t believe how many followers I have already!”

As my feet hit the ground, my phone starts ringing.

A little shocked, it becomes apparent that one of my admirers over Instagram wants to do a video call.

I don’t know if it was just the excitement getting to me, but I answered the call without worry.

The person's face appears on the screen and I’m taken back by the regal-looking woman at the other end of the phone.

I couldn’t help but feel jealous of her lush hair and sumptuous makeup.

“Hiya babe!” she squeals.

Allowing her to see my face, I watch as her face scrunches up in disappointment.

“Oh Hunny,” she whines. “Your face doesn’t match that supple body of yours!”

“What do you mean?” I ask, looking at her confused.

“I assume that sexy body you posted in the lacey underwear is not you?” she asks, seemingly now disinterested in me.

“No that’s me!” I snap in reply.

“You’ve gotta work on the rest of your look,” she scoffs. “A little makeup and a wig or something sweety. Men aren’t going to want to see your normal face!”

“Makeup?” I reply, having not even considered that option.

“Yeah baby,” the lady says giving me a smile. “Maybe you should give that a go!”

Looking around my room, I knew my wife had left some here somewhere.

“Sweety,” the lady says, regaining my attention. “Have you tried Sissypill.com?”

“No…?” I say, giving her a quizzical look.

“Oh Hunny!” she laughs. “I think it might be up your street. Go check it out. I recommend a sissy like you getting the sissy vitamins!”

“Sissy like me?” I reply, almost offended. “What do you mean a sissy like me!?”

“You’re posting pictures of yourself online for men…..,” she says, giving me a funny look. “You’re a sissy, right? You want male attention….no?”

Allowing her words to rattle around in my brain, I felt like the answer should be no.

“I do like male attention,” I say back, surprising even myself.

“Just try the website,” she continues, giving me a wink. “We should talk again when you have. I’ve been looking for a new student!”

About to question what she means, the video call is swiftly ended.

Very intrigued by what she said, I go to Sissypill.com.

What I find…. blows my mind!

After about an hour of shopping, I couldn’t wait to get my items. So I get my items shipped the next day.

I couldn’t wait to try the sissy vitamins!

Calming they’d make me irresistible to men, I hoped they’d make Harry at work notice me!

With the rest of the night being one of the most interesting of my life, I had many men trying to talk to me.

It was almost like I’m a teenage girl. I was getting compliment after compliment!

Eventually falling to sleep, I woke the next morning still wearing my ex-wife's undies.

My morning went as it usually did, but I really didn’t want to take off the feminine panties.

Pulling my work trousers over them, I was excited to start my day knowing what I had on underneath would drive me wild.

Every time anyone came over to speak with me, I wondered if they could tell that I was wearing women's undies.

It was even more thrilling when Harry wandered over. I wanted to bend over right in front of him!

I wanted his strong powerful hands rubbing my supple thighs!

Still, even though I wanted it, I knew I wouldn’t get it! His interests weren’t on me.

I watched on with envy, as Harry chatted with the lovely ladies on the floor. I could see what I needed to do!

All those sexy female clothes and sissy vitamins I’d ordered. I’d been eating out of his hands in no time!

“You’ll be wanting me!” I say under my breath, as Harry walks past and doesn’t even acknowledge me. “You’ll be desperate to touch me!

Once work was done, I rushed to get back to my house as quickly as possible. I couldn’t wait to get home and open my packages.

Running up to my apartment door, I see them all piled up outside my door.

Lugging them inside, I grab the largest box and rip it open.

“Ooo,” I say, pulling out a white and pink short dress. “I like this!

As I empty the boxes, minutes soon turn to hours.

With the last box opened, my living room looks like an actress's wardrobe. Wigs, heels, dresses, skirts, underwear, and other naughty items are strewn about the room.

The one thing I was interested in was the sissy vitamins from that Sissypills website. I’d read that after even one dose, you start to physically change and become more attractive to men!

Unscrewing the bottle, I take one pink vitamin and dry swallow it down.

Straight away my nipples start to itch.  

Giving them a satisfying rub, my phone starts vibrating in my pocket.

Swiping it open, I quickly realize that it’s the woman I spoke to last night.

“Hey,” I say, answering the call.

“Did you take one of the vitamins like a good girl?” she asks, not bothering with a hello.

“Yeah,” I say, showing her the open bottle. “Is it supposed to make my nipples feel so hard and itchy?”

“Yup,” she quickly answers in return. “You should find in the next hour that your hair will feel more glossy. Your skin will also start to feel femininely soft and you’ll get deep urges coming from you behind.”

“My skin is softer!” I say, surprised. “My nails have also grown out. Is that normal?”

“Yes my sissy,” she replies. “Now, I’m your new mistress. Mistress Valerie!”

“I need a mistress?” I ask.

“Yes,” she growls. “And call me Mistress!”

“Sorry Mistress,” I bashfully answer.

“Good girl!” she commands. “Now, do you have a man you want to please?”

“How did you know?” I ask, confused at how she knew I was desperate for Harry’s attention.

“A mistress knows these things,” she boasts. “Ok, have you a wig and makeup?”

“Yeah,” I answer, looking around the room for the black wig I’d brought.”

“Do you have a slutty dress?” she continues.

“Yeah, I brought a few,” I reply, holding up a white and pink dress.

“Good,” she cheers, clapping her hands. “Now, I want you to put that on tonight and send me pictures. Tomorrow I want you to wear light makeup for work.

“For work?” I ask, excited but also a little scared.

“Yes!” she commands. “Mistress has spoken! I will speak to you again tomorrow!”

The phone goes silent and I stand in my messy living room with the white and pink dress in hand. I couldn’t wait to get started.

Looking at the short white dress with pink details, I hold it against my body.

“My legs are going to look killer in this!” I cheer. “Hopefully Harry will notice me in this!”

Slipping the dress over the feminine underwear I was already wearing, I pull up some jet-black stockings too. They really complete the look I was going for!

Putting a pink choker around my next, I place the bob-style wig onto my head.

Once I’ve got it perfectly positioned, I rush over to the bedroom. Looking in my mirror, I love the way my dress rustled with movement.

“Bend over baby!” I whisper at my reflection, showing a little leg.

Spending the rest of the night learning how to do make-up and my hair, I send several pictures to Mistress Valerie.

The next morning, I woke up still in my white and pink dress.

Checking my phone, I’d got many messages from so many different men. I felt proud of myself!

Feeling confident, I pop another vitamin.

Instantly, I feel my body changing a little.  My hips are wider and my waist became a little narrower.

Running a hand down my body, I feel sexy in my naughty little dress.

“I’m going out like this!” I say, posing in the mirror and blowing a kiss. “The world deserves to see me looking so beautiful!”

Confidently, I touch up my makeup, brush my hair, and spray some perfume. Slipping into my extra-large white high heels, I stumble at first but soon get the hang of walking.

On the way to work, I got so many compliments on how I looked.

So many men staring! I knew they wanted me!

I knew I wanted them! Back off ladies, Smooth Stacey’s in town!

Once I’d got to work and sat at my desk, the compliments kept coming.

Everyone single one of the female workers in the office had something nice to say.

They loved my dress, my shoes my hair, and even how soft my skin looked.

Everyone kept telling me how proud they are. How I should live my truth and not be worried about what anyone else thought.

Now Feeling extra confident, I couldn’t wait until Harry got in.

He’d been hiding away in his office all morning. One of the girls told me he wanted to see me in his office. I wasn’t worried, I knew he’d be asking to see me privately!

Knocking gently on the door, he ushers me in.

Like a playboy bunny waiting to be picked, I strut into the room and flick my hair back.

“Hello, Brian,” Harry smirks. “I’d heard about this transformation.

Brain gets up from his chair and walks around his long desk. Standing just in front of me, he looks me up and down.

“You do look very nice,” he comments, touching my hair and then my cheeks. “I didn’t know you are transitioning. I can’t believe how feminine your body looks. Even your skin is so soft!

Enjoying his touch, I look deep into his beautiful eyes.

“The girls had said you’d started acting differently recently,” he comments, still touching my face. “This is a very daring look you’ve gone for and if you don’t mind me saying, I love it!”

“Thank you,” I reply with a giggle. “I’ve been waiting for you to notice me!”

“Oh I have noticed you,” he grins.

“You have?” I ask. “Like I said sir, I’m happy to do anything for you! I’m happy to bend over backward for you!”

“You are,” he says, raising an eyebrow.

Gently touching my leg, he ushers me over to his desk.

“Susan,” he commands to his PA over his intercom. “Cancel all my meetings. Somethings just come up!”

“What should I tell them, sir?” The PA asks in reply.

“Tell them I’m helping a staff member take the next step,”