Litorica Sissy
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Litorica Sissy
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Mark pays a visit to a new submissive hotwife.
A young closeted sissy moves in with two men as part of work.
Adam takes Katie home and demonstrates his new power.
A desire of a sissy to be pimped becomes too real.
Consequences to Lori's actions continue.
Sir enjoys my new body, then puts me on display.
An incident leads to dire consequences.
Jen takes Steven to a lingerie shop and humiliation ensues.
Jenny tells her story...and gets a keyholder.
Sir plays Build-a-Bimbo with my body.
Richard becomes Sandra's sissy maid. Sandra sits on his face.
A student is blackmailed and used by an older man.
Mr. Jenkins is up to his usual tricks.
Andy gets caught by his sister in her panties and it's fine.
The tables have turned for Mark and he learns his place.
Jenny is caught on the machine by her best friend.
My wife's old boyfriend is now an expert on race relations.
Sarah the producer does the celebrity special.
Sissy's training continues and she has her first outing.
Just another day at work, or so Jay thought...
Part 4 of the life of pussyboi Max, now officially Maxine.
An intense evening with my wife and her dominant lover.
Rory is put through an intimate situation with a new friend.
A Primal Dom makes a sissy an offer she can't refuse.
A man allows himself to be a coward to another stronger man.
A young journalist accepts an invitation to a strange island.
Marcy's plug puts her in an awkward predicament.
A early morning hookup with a drunk crossdresser.
A Primal Dom makes a sissy an offer she can't refuse.
Sissy gets an unfortunate tray 'upgrade'.
I pledge my fidelity to a real man.
A sissy man meets an old man at a hotel.
Attack of the Futanari Cheerleaders!
Rory wakes her Mistress after a night of fun.
Jayme reflects on her new direction in life.
Naive boy's conversion into girly fucktoy is completed.
Permanent chastity is exciting, but would Rory ask for it?
A not-so-straight guy gets turned out at the gym.
Word starts to get out how I'm owned by Mistress Z.
Jennifer's 2nd day and beyond, with some consequences.
A new cage for Rory, along with a few new rules...
Rory is readied by her Mistress, but for who?
Rory earns her own sub, with a twist from her own Mistress.
Rory dreams of servitude, but does it match reality?
Tom is replaced in a humiliating fashion.
My journey into a life I didn't expect.
A crossdressing sissy gets used by an attractive couple.
Rory meets two Mistresses, controlling her with choices...
A devious Mistress teases Rory, needing permission to cum.
Mistress brings Rory to a bar, but it isn't exactly normal.
Rory's relationship with her roommate deepens, and shifts.
Mistress watches Rory intently, as she is used by a stranger.
Rory is a good girl, but can she handle this BIG surprise?
What happens when your hidden sexual secret becomes known?
Rory's new roommate takes on a new role.
Rory's Mistress needs a birthday present for her husband...
Rory finds a job as a secretary, with strict conditions.
Rory's Mistress finds her a new job, with certain perks.
Rory is exposed, in more ways than one...
Rory is used by Mistress, but not how she expected...
Rory is given new shoes by her Dom, but at what cost?
Going deeper into the warren has never been so much fun.
The Cottage Service with a Polished Edge.
A sissy finds herself under a sadistic cop's thumb.
Tom is subjected to a lot at the Office Christmas Party.
Confessions lead to atonement, or sorts.
Left caged for a month, Rory was going to cum. Sort of...
Rory takes over until she's unlocked. "If" she's unlocked.
A walk on the town after a gift from Mistress...
Rory visits her Mistress for a night of being her good girl.
Bree can't be bought, but can be owned.
A law makes sissies legal property of their master.
This is the Finale, Dan becomes one of the girls.
Tom hears a strange noise coming from Charles' office...
It's the big day for Michelle, but it's fun for mostly all.
FLR couple introduce cuckolding due to underperforming hubby.
Cuck orally serves wife and Master. Mistress has plans.
Naive boy is inspected and put in panties.
Jayme's mom takes him shopping for his new life.
Lori gets punished; Michelle's coming out party.
Amy's date is more than she bargained for.
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The house sissy is baptized by the cum of her fraternity.
Mistress introduces her new sissy maid to the Master.
The house sissy continues her initiation!
House sissy starts to take her role seriously!
Initiation turns out to be more than Andrew expected!
The Wedding. Branded. The sissy slave maid.
Aunt Mo finishes with Suzanne. A visit to the Nunnery. Home.
Richard is given his new schedule as Mistress' sissy maid.
High Heels, Butt Plug & New Schedule For Sissy.
Mistress buys Richard high heels & a butt plug
A cuckolding couple try it for the first time at home.
Orgasms and Bath Ritual For Mistress.
Pain or pleasure? What will Dave choose?
Nicole and Jamie bring it all to a new level!
Middle age subs fantasy girl becomes an extreme reality.
Some dressing and make-up and a three-way.
Erin considers Michelle’s sissy cuckold arrangement.
Sissy gets fucked by Sarah's bull and learns about pain.
Sissy gets put in chastity and turned into a house maid.
Debroah finally agrees to dominate her husband.
A sissy maid plots revenge against a dominatrix in training.
Tom caught cheating on wife. May not like wife’s solution.
The sissy maid serves her mother's dinner guests.
Wimp sissified, blackmailed & transformed for black masters.
Sissy Jenny discovers Mistress Lizzy's for her.
A sissy maid and apprentice dominatrix are punished.
Sissy Slut cuckold. CBT for Blondie.
Wife's sexual frustration leads to her taking control.
Oliver's father has some fun before work.
An unforgettable private party for the Mistress is held.
Oliver's father's humiliation continues.
Jenny continues to prepare with Mistress's help.
Married sissy in for the experience of her life.
The sissy maid is getting prepared for her first day.
A son is forced to become his mother's own sissy maid.
The disturbed man-boy gets into things he shouldn't.
A wonderful night in Hollywood ends very special.
Chantel's first night as the club's new t-girl Dominarix.
Chantel plays sexy like with staff and with her love Carl.
Continuing with Chantel's first day at The Jade Maid Club.
Chantel arrives at The Jade Maid Club.
Chantel, begins her orientation and training.
The beginning of of a sissy's recruitment.
A hot Hawaii Honeymoon and a future together.
The Wedding and a very Special Night of Love Making.
Chantel has her big surgery, true love is shown.
Chantel lovingly tells Mikel what she wants.
Mikel & Chan go a music concert and more.
Chantel and Mikel are a couple in love, fun Christmas Party.
Chantel goes on a date and finds a new Beau.
Chantel meets Jack and things are great between them.
Chantel, works as a classy t-girl escort now, lots of fun.
Sam suggests a way for Jean to cuckold her sissy more often.
Chantel, Helen & Alan Celebrate her role as a transsexual.
Chantel moves on to contracted out maids work.
I begin my career in sissy pornography.
Chantel moves deeper in life as a sissy including slut work.
My new sissy life to my Mistress wife grow more entrenched.
Chapter 2 of this Mistress wife, sissy husband, lifestyle.
How I went from a loving husband and to a sissy for my wife.
Part 6 of Sissy Chantel's journey into becoming a slut.
Continuation of Sissy Chantel's decline into a slut's life.
Part four of Sissy Chantel's decline into a sluts life.
Part Three of Sissy Chantel's decline into a slut.
Part 2 of Sissy Chantel's decline into a sissy lifestyle.
A journey into sissy slut play then sissy lifestyle.
A full shift to pull today and tonight.
Moving on with my life at 'The Agency'.
Another Hookup with Master, Chantel's life begins to change.
Sucking cock, public humiliation and a good butt fuck.
Sissy Chantel serves and services two Dominant men.
Chantel finds sissy fantasy will become her sissy reality.
Wedding plans, a guys Stag and a Gals Staggette.
Chantel & Kerri meet for the partnership & fun at dinner
More becoming a sissy maid & slut vol.14 ch.23
Journey of this Tranny Dominatrix and the men who visit.
More becoming a sissy maid & slut vol.13 chapter 22.
More becoming a sissy maid and slut Vol. 12 Ch. 21 bonus.
More becoming a sissy maid & slut, vol.11 Ch.18-19-20.
More, becoming a sissy maid & slut, vol.10 Chapter 17.
More becoming a sissy maid & slut, vol. 9, Ch. 15 & 16.
All contents © Copyright 1996-2022. Literotica is a registered trademark.
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Femboy sucks dildo in parking garage.
Archie is taken to his first rave as Kelly.
Rory goes to College, and finds help in an usual way.
A submissive returns to his goddess after a year apart.
Denise's high stakes dinner for Joey with special dessert.
Am effeminate young man is mentored by an older woman.
Mistress Kristy's second session with Vic.
Ashley's plans for Dolly are interrupted by Rose's return.
Markus pursues Shireen. Darius fully embraces sissy slavery.
I was looking for a mistress. I guess I got what I asked for.
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Week 3 brings even more humiliation and training.
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Favorited by ruby76 , Renee_B , Jonathan72 and 18 others
Full Scholarship Naive college kid tries to make ends meet, gets in deep.
Made Into His Girl Luke is tricked into chastity by Sissy and her brother Jake.
Working the Holidays Classic Christmas tale of blackmail and forced feminization.
A Slut is Born Young man forced to be a woman
Blackmailed by Mr. B A student is blackmailed and used by an older man.
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ATTN: All characters are purely fictional. All characters are over the age of eighteen. This story contains elements of reluctance and non-consent.
The next 6 days were torture. I was used to masturbating multiple times a day so not only was I horny, every time I started getting turned on my cock would try to grow and cause discomfort in the cage. I did my best to keep everything clean but it proved to be a full time job. At some points I had almost a steady stream of sticky clear pre-cum oozing out of the pee hole. On top of this I realized quickly that I had to sit down to pee and wipe like a girl, which was itself humiliating. Other than that my life didn't change much, it wasn't like I was getting laid before I had the cage. Once again time seemed to move slowly through the week but sure enough it passed and before I knew it I was on his doorstep again.
Upon entering his house for the third time I walked immediately to the bathroom and showered. This time on the counter by the sink there was not only the usual panties, collar and stockings, but also eyeshadow, blush, and lipgloss. In addition to these were a pair of pink lace up high heels that resembled running shoes in my exact size. My mouth gaped. As I applied the lip gloss and blush I couldn't believe I had gone so far for this disgusting man. I told myself I had no choice and if I didn't want to be publicly humiliated I just had to get through it.
I exited the washroom unsteadily wearing the new accessories and was greeted by a wolf whistle.
"What do you say for the new gifts?"
He cleared his throat and I realized my mistake.
"Thank you daddy" I corrected myself.
"Let's get a better view of how it all works together. Do a fashion walk for me." he said sitting on the couch.
I stumbled through my attempt, very uneasy on the heels even though they were chunky like platform shoes.
I walked up and down the living room once more leaning forward on my toes for balance, again stumbling more than once.
"Try tightening your butt muscles and relaxing your lower back. Stand up more straight too." he coached.
No dice. Again I barely made it across the room.
He left the room and returned holding out a pump bottle and something small and pink. It took a second but I recognized it as a butt plug.
"Do you want to put it in yourself or do you want me to help?"
I swallowed hard. It was getting clearer now as if the outfit didn't give it away already. He was trying to groom me. Last week was stockings and a collar, this week it was makeup, heels, and a butt plug. What was next week going to be? I had to take a stand.
"No daddy, I'm not going to wear that" I said as politically as possible.
"Have you forgotten our agreement?"
he asked, "Anything goes for 3 hours a week. You're telling me you want to void our agreement?"
I stood there trying to show no emotion as I thought about what that meant. My end of the deal was clear, do whatever he says. His end of the deal was to pay me but more importantly it was to delete the Grindr profile and not put up a Tinder one. Being in college, everyone I knew was on Tinder so it wouldn't take long for something like that to damage my reputation.
"No" I finally answered understanding the gravity of my situation.
"Then let me repeat my question, do you want to do it yourself or do you want help?"
I took it from him and turned to walk to the bathroom but felt a hand grip my arm.
My heart sank as he guided me to the ottoman and had me kneel on it. I looked at the plug in my hand as he hooked his thumbs under my panties and pulled them down. It was pink, translucent and rubbery, and at just under an inch wide and only 3 and half inches long it so it wasn't very big.
"Use some lube on your hole and on the plug. It'll go in easier." he instructed.
I took his advice and made sure to coat the plug in a generous amount of the slippery gel. I took some more in my hand and reached underneath and behind me. As I did I felt hands grip and spread my ass cheeks wide causing me to panic and jerk forward.
"Relax girl" he said and gave the right one a quick slap, "This will help"
He spread them again and I felt completely exposed as the cool air touched my hole. I rubbed the gel on it carefully not really sure what I was doing.
"Push some in honey. Just your finger tip." he guided.
I followed his instructions and breathed heavily as the cool gel was pushed inside slightly. My finger slipped in a little bit and as I tried to guide more lube in it went past the nail almost halfway in. It felt uncomfortable and slightly painful.
"Look at you, now you're just playing with yourself." he laughed.
I held the plug up to my hole and took a deep breath before pushing slightly. It didn't move very far so I gave it more effort. The tip seemed to slip in and I began to coax it in further but even at its small size it was stretching me uncomfortably. The biker must have been getting impatient because I felt one of his massive thumbs over my finger apply pressure and push steadily. The plug invaded my hole and at its widest point seemed to get pulled inside me with little effort. He gave me another spank and pulled my panties up before helping me to my feet.
"A little uncomfortable but not as bad as I thought it would" I answered honestly.
"You're a little tight. Just means we have to loosen you up. Let's try again, walk across the room for me."
Loosen me up. The words hung over me but I persevered walking steadily forward. As I did I resolved that this was the first and last thing that was going back there. Surprisingly he wasn't wrong about the plug helping me walk in the heels. The uncomfortable feeling in my ass translated to a much easier time balancing and finding my center of gravity. I paced the room twice and looked back at him, feeling pride for a moment before remembering my situation.
"Much better" he complimented, "But still needs some work"
He had me do his dishes, sweep his floors, and then his laundry. There was still another hour and a half left when I found him in the living room, the laptop on the floor in the same spot as the week before. He nodded his head toward it and I found my place on the ground, put my headphones on, and pressed play. I had grown somewhat used to the plug inside me and as the images began flashing I almost became unaware of it. In fact as the music built I found myself clenching on it in beat and felt my cock grow inside its cage. As the words flashed against the screen I kept having to remind myself it didn't apply to me. The phrases were much more obscene than the video from the week prior. "You are a cocksucker" and "You need your ass filled" were repeated moreso than any others.
As I watched I felt my panties being pulled down and a hand pushing my back down, helping me arch. I looked back and he gave me a spank before returning to the couch.
It wasn't long after when I first felt the plug slipping slightly. I clench down and found that I could kind of control it with my muscles and pull it back in, holding it there. This worked a couple times but eventually I couldn't hold it and it slipped out onto the floor. I pulled the headphones off one ear and turned to look at my business partner.
"Hmmm looks like we need to go up a size." he remarked.
"Uhh, no, I pushed it out by accident... it's fine really." I said, sounding more desperate than I meant to.
"Eyes forward. Reach back and spread your cheeks, I'll get it in." he responded.
"No... really, it'll just slip in, I can do it." I pleaded.
I watched as he picked up the plug from the ground and put it on my back as if it were a table before getting up and walking away. I went to reach for it but he turned around.
"If that plug moves, it's going in your mouth." he said in a serious tone.
I focused all my energy on staying perfectly still. He couldn't mean that could he? They did stuff like that in porn but it was always after the camera cut, giving the actors time to clean. His tone showed how serious he was however and I wasn't about to risk it. He returned quickly and I heard him kneel behind me. He fiddled with something for a moment and then I felt something cold and blunt at my hole. At this point he had not picked up the plug from my back yet and I realized he would be inserting a new one. The pressure began slowly and gently but then increased suddenly until I felt a slight pop. There was more pressure after this and I grit my teeth, my muscles contracting until I felt the pressure grow.
"Relax and push out." he said calmly.
"Out?" I questioned and received a quick spank in retort.
I did as he asked even thought it seemed counterintuitive. Miraculously the pain subsided as the pressure grew and he pushed it into me all the way. It felt huge by the time my ass sucked the last bit in and my curiosity got the better of me.
"How much bigger is this one?" I asked, the mix of discomfort and slight pain making my voice waver slightly.
"You'll find out when you take it out later."
I put the headphones back on and focused on images filling the laptop screen to distract me from the new invader. I told myself
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