Enslaved Sissy Stories

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Enslaved Sissy Stories
The stories posted here have all reached certain standards of readability and content. I focus on collecting stories that involve humiliation of a young, feminine submissive by a dominant male. As a rule, all the stories posted here are X rated, but they involve more than straightforward non-consensual sex. Instead, these stories will pay attention to the emotional and psychological humiliation of the submissive. More often than not, there is a training or feminization scenario through which the sub learns to submit to and please "real men".

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Riana's Collection of Sissy Humiliation Stories



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A collection of sissy humiliation stories I've read and liked, with strong emphasis on dominant males and submissive boys or sissies.
“On your knees, sissy.” Pointing to a spot on the floor
before him, Sir Michael added “Now.” There was no change to the
tone or volume, but I could hear the power behind his words.
Before I knew what I was even doing, I rolled off the table and
knelt before him.
“Open your mouth.” Just standing there, he warned “Don’t
make me ask again.”
I couldn’t believe what I was about to do. Responding to his
commands almost on instinct, I slowly opened my mouth wide.
Afraid to even touch – never mind taste – his cock, I opened as
wide as I could.
“Very good.” Grabbing the back of my head, he pulled me
roughly forward, forcing his cock into my mouth. Disgusted and
ashamed, I gagged on the torpedo of flesh, sure I was going to
throw up.
“Relax and suck,” he told me, “Relax and enjoy it.” It was
like he had some kind of hypnotic control over me. Despite my
every desire to spit out his cock and run, I felt myself relaxing
and my urge to gag fading. “Good, now suck it. Suck it like a
good little sissy.”
Shaking my head no – as best I could – I pleaded with my
eyes. He could fuck my face, force me to swallow his dick, but he
couldn’t force me to take the initiative. Maybe, just maybe, he’d
tire of my passive acceptance and lose interest in me.
Sir Michael shrugged, his massive shoulders rolling beneath
his shirt. Lowering his coarse, callused hand to my face, he
pinched my nose tightly shut. “Suck or suffocate. Your choice.”
Date: Tue, 24 Mar 1998 20:33:28 PST
From: Sissipus !
Subject: A Sissy Enslaved
A Sissy Enslaved
by Sissipus
* * *
As I stepped into the department store, I had to resist the
natural urge to turn left and head for the electronics section.
Instead, I turned right, penetrating deep into the mysterious
world of women’s apparel. Feeling conspicuous, I tried to look as
if I belonged, relieved that there were no crowds so early in the
day. This was the third time I had attempted this, and I was
determined not to chicken out again.
I knew what I wanted, but not where to find it – and I was
far too nervous to ask for help. Of course, it ended up being in
the last place I looked. Wandering anxiously through the aisles
of women’s lingerie, I tried not to look embarrassed – and failed
miserably. Everywhere I looked, I was surrounded by lacy, silky,
feminine treasures. And I’m not just talking about the plain old
bras and cheap panties you see in most stores. This was a proper
lingerie department, with everything from garter belts to
expensive stockings to the fanciest babydolls and teddies you’ve
ever seen.
Finally, on my third pass through, I spotted the wall
display I wanted, tucked around a corner. The moment I saw them,
my embarrassment faded, replaced by an intense longing. Carefully
selecting three pairs of the fancy, floral-print panties – all in
my size – I carried them proudly to the cashier.
An attractive, middle-aged woman, she smiled as she totalled
up my sale. “That’ll be $13.77,” she told me. “Would you like a
box?”
I was tempted, but told myself this time was going to be
different. In the past, I’d confined my purchases to holidays,
when it could be safely assumed they were gifts for a girlfriend.
Unfortunately, that meant my collection was as limited as it was
small. However, from the moment I had seen the panties in the
flyer, I knew I had to have them. “Yeah, that’d be great,” I
blurted out, cursing myself for my cowardice.
If she suspected anything, the saleswoman was kind enough
not to show it. “Your girlfriend will love these,” she assured
me. “They’ve been very popular.”
Blushing, I thanked her politely and all but rushed out of
the store. The moment I was clear, I collapsed onto one of the
mall benches and laughed. I had done it! I had actually done it!
Now that it was all over, I felt a rush of adrenaline flood my
system, prompting me do something I had never dared before.
Hurrying to the bathrooms, I locked myself in one of the stalls,
stripped off my jeans, and traded my briefs for a new pair of
panties.
“Ohhh, yessss.” Sighing, I softly caressed my satin-clad
cock, loving the feel of the material beneath my hands. The pair
I had on was a kind of peachy-pink, decorated with elaborate
yellow and red flowers. They felt so wonderful, so sexy, I just
wanted to stand there and feel myself forever. Instead, I tucked
the head of my erect penis back down beneath the waistband and
slipped into my jeans.
“Oh, sorry.” Nodding, an imposing, older gentleman stepped
back so that I could escape the stall. He was tall, with dark
hair – probably in his early 40s – but that was all I noticed as
I slipped past him on my way to the door. I was half-afraid he’d
be able to see the lines of my panties, but was too excited to
care. Feeling rather proud of myself, I suddenly panicked as I
felt his hand come down upon my right shoulder.
“Hey!” Spinning, I pushed his hand away and stepped
backwards.
“Just wanted to give you these,” he smiled. “You left them
in the bathroom.”
Snatching the bag from his hand, I silently cursed myself
for my stupidity. After all I had gone through to get them, I had
forgotten my new panties on the floor. “Ah, thanks,” I smiled
back. “Girlfriend would shoot me if I lost them.”
“No problem.” Grinning, he held out his hand to show there
were no hard feelings. Feeling guilty for having snapped at him,
I shook his hand, impressed with his powerful grip. I only hoped
my hand didn’t feel as sweaty to him as it did to me.
“Thanks again.”
Letting go my hand, he just nodded and walked back into the
bathroom.
* * *
After that close call, I spent a good hour wandering the
mall, just trying to calm myself down. Eventually, my nerves did
ease, but the slippery feel of the panties on my cock was just
too exciting to resist. “Go for it,” I told myself as I passed
the drugstore. “Come on – if you can’t do it now, you’ll never do
it.”
I had to admit I made a lot of sense. Clutching the plastic
bag in my hand, I turned into the drugstore and headed directly
for the feminine protection aisle. “Wow.” From one end to the
other, all five shelves were filled with maxipads, pantiliners,
and tampons. Blue boxes, white boxes, pink boxes – who could have
imagined there’d be so many brands and styles! Somewhat
overwhelmed by my choices, I wandered further down the aisle to
the shaving section.
What I needed first was a lady’s razor. I’d tried shaving my
legs before with my usual razor, and the result had been a
bloody, stubbly mess. I had no idea what would be best, but
recognized the name Revlon from their cosmetics. Figuring they
had to know what they were doing, I bought one of their razors
and some extra blades.
Feeling a little more confident, I returned to the other
aisle and pondered my choices. “Those look good,” I told myself
as I grabbed a small, square white and blue box. Tampax Compak
tampons – I knew the name and they came in an easily concealed
box. As far as pads went, I had no idea, so I just grabbed a
rectangular pink box that caught my eye. “Stayfree Carefree
pantiliners,” I read. “Hell, why not.”
Excited, I hurried to the checkout before my sudden burst of
confidence could fail me. Thankfully, the salesclerk was a sullen
young woman who had no interest in striking up a conversation.
Quickly paying her for my purchases, I rushed out of the store
without even counting my change.
“Unghh.” Slamming right into someone, I stumbled back,
prepared to apologize. “Damn, I’m really sorry. I didn’t even
see-” Recognizing the man from the bathroom, I stopped, unable to
shake the fear that I had been followed.
“Get everything you need?” he asked. Winking, he suggested
“I hear there’s a sale on nailpolish in their cosmetic’s
department.”
“Ah, no, that’s okay.” Swallowing loudly, I tried to think
of a tactful way to flee – without looking like I was running
away.
“You’ve never bought anything like this for yourself before,
have you?” he asked. His voice was a smooth baritone, quiet but
conveying confidence and power. “Probably feeling rather proud of
yourself right now, aren’t you?”
“Sorry, but I have to be going,” I replied, lowering my
head. Humiliated, I wanted nothing more than to get as far away
from him as possible.
“Why don’t you let me buy you a coffee? I have a proposition
you might be interested in.”
Shit. Not only had he been following me, he was obviously
some kind of pervert. “Thanks anyway,” I replied, “But I’m in a
hurry.”
“Ah – I see.” Reaching into his suit pocket, he suggested
“Maybe this will change your mind.”
No, no, no! I’d been too excited to notice at the time, but
somehow he’d managed to snap a picture of me in my panties. From
the angle, it was obvious he had taken the picture from above the
stall door. Staring down at the incriminating Polaroid, I
blanched, terrified of what he intended to do with it.
“Just join me for a coffee,” he suggested again. “I REALLY
think we should talk.”
Too upset to speak, I nodded and reluctantly followed him
over to the foodcourt.
* * *
“Yes?” Smiling a beautiful, sexy smile, the tall blond asked
“Can I help you?”
Whoa! Easily six feet tall, with blond hair falling all the
way to her waist, the woman at the door was one of the most
beautiful creatures I had ever seen. She was dressed in a tight,
formfitting pink minidress, with matching two-inch heels. Her
nails were an inch long, and painted a bright, shiny red. Tearing
my eyes away from her ample bosom, I had to look up slightly to
admire her face. Small and round, with a perfect little nose and
sharp, high cheekbones, she was wearing just the right amount of
makeup to highlight her features. “Ah, S-s-sir Mi-Michael,” I
stammered, “Ah, wanted to see me.”
“Oh, you must be his new sissy.” I’d been hoping she was his
wife – or girlfriend – but from the way she laughed I knew she
was to be part of my ordeal. “Please, come right in.”
Stepping across the threshold was probably the hardest thing
I’d ever done, but I really had no choice. Nervous, I tried not
to flinch as she locked the door behind me. “Ah, nice place.”
“Yes.” Placing the tip of her index finger to her mouth, she
carefully looked me over. “Hmm, you’ll do fine, not bad at all.”
Nodding, she told me “Take off your clothes and leave them on the
floor.”
“Right here? Now?” Embarrassed, I had hoped I might be able
to ease into this.
“Now!” Scowling, she knelt down and began undoing my pants.
“And be quick about it.”
It should have been arousing to have such a beautiful woman
undress me, but she was so cold, so businesslike, I was
embarrassingly shrunken and limp. Lifting my feet, I allowed her
to pull off my shoes, which she then tossed in the garbage.
“Might as well take care of this while we can.”
“Ouch!” I winced as she roughly forced my testicles up into
my body. Then, grabbing my limp cock, she pressed it between my
legs and secured it in place with a wide strip of flesh-coloured
tape.
“As long as you are in this house, you will keep that
abomination hidden at all times.” Slapping my ass, she assured me
“You won’t have need of it anyway.”
What had I gotten myself into? Were the half dozen pictures
he possessed really that bad? Unfortunately, I already knew the
answer to that. The whole reason I had been so secretive about my
crossdressing was that my family and friends were all close-
minded, prejudiced, fools. Alone, the picture of me taking the
tampons from the shelf would have been enough to condemn me.
“Yes,” I replied, “He told me that.”
“Good. Follow me.” Turning on her heel, she led me deep into
the house and down the stairs to the cold, dark basement. “Get up
on the table and lie down on your back.”
Nervous, I followed her instructions. The instant I was in
position, my blonde dominatrix shackled me to the table. Thick
iron manacles encircled my wrists, my ankles, my waist and my
neck. Within moments, I found I had lost the freedom to do
anything more than turn my head.
Running her fingers through my hair, she said “Nice length,
good body, but that colour has got to go.” Long, brown, and
usually tied back in a ponytail, I had let my hair grow in hopes
of someday fulfilling my fantasy of crossdressing in public. As I
watched her drag a small basin beneath my head, I began to regret
my decision.
Grabbing my head, she forced it down into the warm water. I
couldn’t see what she did next, but whatever she was doing smelt
awful. When she began working the foul-smelling goop into my
hair, I realized it was hair-dye. It felt strange – and the fact
that it was so obvious a change bothered me – but I was curious
to see how I would look when she was done.
“While that sets,” she said a while later, “We’ll take care
of the rest of you. We’ll start with a good, close shave, and
then move onto your makeup.” Lathering up my legs with scented
shaving cream, she continued up my body to coat my crotch, chest,
and arms. Then, not saying a word, she shaved me clean with
short, expert strokes. Not once did she even nick me, despite how
long and coarse my body hair was. This woman was clearly a pro,
and I was surprised to find myself enjoying this portion of my
servitude.
Before returning to my hair, she applied long, pink
extensions to my nails; pierced both my ears, inserting a purple
hoop into each; made up my face; and rubbed some kind of cream
into my chest, making my nipples stand sensitively erect. For the
most part, this was straight out of my wildest fantasy, but
knowing what it was all leading up to robbed me of the chance to
really enjoy it.
Finally, she finished my hair, styling my newly-dyed tresses
into a long, full, wavy mane of fire. I’d always loved redheads,
and was slightly aroused to find myself suddenly among them.
“Ah, could you loosen my chains?” I asked, hoping my silent
submission would earn me a little mercy. “I can hardly feel my
right hand.”
She just laughed. “If that’s the worst that happens to you,
count yourself lucky.” Still grinning, she said “Now, I’m going
to release you and you’re going to turn yourself over. Obey, and
you’ll be fine.”
What else could I do? Nodding, I turned onto my stomach,
gasping as my nipples came into contact with the cold, hard
surface.
“Like that, do you?” she asked. “I can promise you it’ll
only get better.” When I remained silent, she snapped “Well, DO
YOU!”
“Yes, yes, I like it.” Damn, just when I started to feel
comfortable around her, she’d turn back into the bitch from hell.
She hadn’t done a thing to harm me, but I was already emotionally
drained.
“Good.” Slapping my ass, she told me to relax. “Relax, you
sissy fag, or I’ll make you relax.” Gulping, I did as she
commanded, then winced as I felt her finger worm its way into my
ass. “I’m told these are your favourite brand,” she laughed,
waving a tampon in my face. “Let’s see how you feel about them in
a couple hours.” With that, she replaced her finger with the
plastic applicator, slowly inserting the cotton tampon into a
hole it wasn’t meant to invade.
“Unngghhh!” At first, I hadn’t really felt anything, but now
I felt like I was burning down there. As she pulled the
applicator out, I found I suddenly had to go to the bathroom.
“Shhhh, can . . . can you take it out for a minute?”
“Ha! You have a good sense of humour – for a wannabe slut.”
Toying with the string, she told me “Sir Michael just loves the
sight of a tampon string hanging from his sissy’s ass. Says it
just makes him wanna tear it out and fuck you silly.”
No, this was too much. I was beginning to think it might be
better to just leave and deal with the consequences of exposure.
Unfortunately, that was no longer an option.
“Now, sissy, I’m going to whip your ass until you’re good
and red.” Brandishing a long, black leather whip, she gently
stroked my back with it. “Cry out, and I’ll just keep on going.
Lie there like a good girl, and this will go much easier.”
Nodding, I turned away and bit my tongue to keep from
screaming. “Unnghhh!” Feeling the first, sharp bite of the whip,
I couldn’t help but gasp out in pain. This had never been a part
of my fantasy, but I reminded myself that it was no longer MY
fantasy. Clenching my hands into tight fists, I used my long
sharp nails to distract me from the pain in my ass. Strangely,
the longer she whipped me, the less it hurt. Actually, by the
time she was done, I felt more hot than hurt, and more tender
than sore.
“Mmm, I love a bright red ass on my slaves.”
Darting a glace over my shoulder, I watched Sir Michael
emerge from the shadows. I hadn’t heard him come down the stairs,
which meant he must have been there all the time. It didn’t make
any sense, but knowing he had witnessed my humiliation only
deepened my shame. “S-s-sir. I didn’t know you were there.”
“Why, my pretty little sissy, that’s precisely the point.”
Giving a gentle tug on the string hanging out of my ass, he
grinned. “You can go now, Kara. There’ll be a small bonus for you
in the morning.”
“Thank you.” Giving me one last whipping, she whispered in
my ear “If you want to start out on the right foot, beg to suck
his cock. He likes it when you beg.”
No, there was no way I’d beg for it. I might have to submit
to him, might have to let him rape me, but I would not beg.
Turning my face away from hers, I waited to see what my temporary
master had in mind next.
“On your knees, sissy.” Pointing to a spot on the floor
before him, Sir Michael added “Now.” There was no change to the
tone or volume, but I could hear the power behind his words.
Before I knew what I was even doing, I rolled off the tabl
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