Sissy Panties Stories
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Sissy Panties Stories
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by maturesubmale_for_F
on Apr 20, 2020
by EROTICbearscribe
on Jan 20, 2020
by maturesubmale_for_F
on Apr 22, 2020
by CrossdresserCaitlyn
on Jun 19, 2018
by maturesubmale_for_F
on May 12, 2020
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The next afternoon, Johanna invited many of the Goddesses of the Council over for lunch. Much to everyone's surprise, Representative Pencalia arrived as an uninvited guest. Pomona prepared a fine meal as the Goddesses deliberated over various issues. Pomona was very accommodating to the guests, serving them tea and salad and shrimp. She even placed cloth nap...
His alarm goes off at 6 AM that Saturday. On any other Saturday he would ignore the alarm and sleep in until 10 or 11, but not today.
Today is Service Day, and he couldn't be happier about it.
He gets out of bed quietly, careful not to wake his wife as he does so, and tiptoes out of the room and down the hall to the empty guest room. His outfit for the day...
1. Becoming a lesbian sissy slut
I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...
Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS.
*****
THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...
Dear readers,
This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one.
Enjoy and please take time to give me some feedback!
Theo
3. Intermission: Further training
Following the loss of my sissy virginity just after I had turned eighteen years old,...
I couldn't wait to get home from work. My wife said she had something special ready for me. A month ago, she'd found out about all my sissy fantasies when I forgot to clear my search histories. Instead of divorcing me, she did more research and decided to embrace me as a sissy. Now every time I get home, I strip off my suit down to my panties, thigh highs, a...
I awoke at 6:00 A.M. and set about preparing for my sissy's surprise. I opened the door to see him there on the bed, his ankles and wrists still cuffed to the four corners of the bed. His head was still encased in the bondage hood and he lifted it as I shut the door and approached the bed.
"I trust my sissy slept well," I cooed as I began to release him fr...
Lunch was a pleasant time. I'd prepared and served the food, but we had sat together in the lounge. The blinds down against the weather and prying eyes. The time had felt much closer to friends chatting over lunch than the Mistress-sissy relationship of our previous time together. Viv probed gently about my desires. Intently interested in where and how I had...
Being feminine is taught. Correcting your nasty masculine behavior with feminine manners and class is what you need. Being a sissy is your new reality. I am going to make you the pretty little girl you have always dreamt of being. You need to be taught ho live your every day life properly. You can only dream of being as sexy, girly and attractive as a real w...
When I woke up in the morning I saw my girlfriend getting ready for work. She sees me awake and reaches out and rubs my penis outside my panties. While rubbing me she tells me if the house was spotless when she got home sissy would get a special treat tonight. She let's go of my dick, smiles and leaves for work.
Still hard I jumped out of bed immediately a...
THE DOMINATRIX ORDER: FEMDOM EROTICA 2
BOUND BY LAWS
BY J.W. SMITH
***
"All Women Are Created Equal" was inscribed on the bronze plated plaque on display in Representative Johanna Aletheia's office. It was the declaration put forth by The Founding Mothers of Femininus, of which Johanna's ancestor belonged to. Johanna was of the oldest lineage of Feminin...
The elevator doors slide shut and Sissy Kimmi taps the special access code into the keypad. Then she presses the "PH" button. In few seconds, she'll be at Mrs. Henderson's place on the top floor.
Mrs. Henderson is not the type of woman who sends invitations to sissies. She's the type who tells 'guests' where to be and when to be there. Her handwritten summo...
I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle...
Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife.
Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves.
Jere...
Special thanks to BrettJ for his keen eye and editing abilities. Couldn't of done this without his help and patience.
======================
Abby was the baby of the family. She had three older brothers; Mark, Mike, and Matt. The boys were 3, 4, and 6 when she was born. Mark, the youngest of the three boys, was the one who started calling her Sissy, and wo...
I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it.
I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...
1. Miss Stern delivers both punishment and pleasure
I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...
It happened during the summer of 2004, when Billy was sent to live with his grandpa. Billy's dad left him and his mother when he was a year old. Susan did the best she could as a single mother to raise him. During his high school years, Billy started to hang with the wrong crowds and got himself into a few minor scrapes. Billy turned eighteen and graduated h...
As I sit here in the outer office space of the company CO, I look like an ordinary male secretary. On the inside I'm wearing a pair of pink lace panties, at my bosses request. You see I'm really a sissy inside and my boss takes advantage of this at every possible opportunity. I've worked here for 2 years now and it wasn't always this way. My boss, Elaine, a...
Since giving himself away in his first prostate exam to his Dominant Doctor Megan he had been prepared for use by an old Master, now Sissy was on her way to be used.
Sissy was breathless as she read the text from Master V, she looked around the small airport to make sure she didn't know anyone, whilst she was looking at her texts. Thank goodness she didn't....
Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...
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A D/S couple experimenting with crossdressing and discipline
Miss Misandry prided herself in her various toys, all designed to bring her amusement, pleasure and lots and lots of fun. Coming home from a shopping spree where she had found herself a new outfit for her favorite toy she threw herself on the sofa, propping her feet on the cushions. Looking around she waited, patiently, and then she heard rustling from the other room. Soon Sissy came out, naked as per her instruction, besides the hot pink cage he had been wearing since the morning.
Sissy approached her, getting down on his knees. He removed her shoes carefully, eagerly starting to rub her feet. Miss Misandry smirked and made herself even more comfortable.
“You’re always on such good behavior when you’re locked up…” Miss said teasingly, wiggling her now free toes in sissy’s face. She sees a blush creeping over his neck and ears and he continues to work on her feet.
“I think someone is hoping for a treat tonight..” Miss says as she detaches her foot currently getting all of sissy’s attention, resting it instead on the top of his cage.
“Miss, only if I’ve earned it of course”
“Of course…” Miss Misandry raises an eyebrow and moves her foot a bit. “…and how are you planning on earning it?”
Sissy pauses for a moment and then moves on to work on the foot currently not resting on his cage which is growing smaller by the minute.
“I will be such a good sissy for you Miss, I promise. I’ll rub your feet and whatever else you might want” Sissy smiles hopefully. Miss clears her throat and gets up from the sofa. She grabs her shopping bag and hands it to sissy who is staying put on his knees.
“You will be wearing this tonight, you’ll be my perfect Sissy Toy all dressed up” She watches as sissy looks down in to the bag and pulls out a soft pink satin dress with a puffy skirt and lacy ribbons scattered all over.
“…you?” Miss smirks and motions for Sissy to stand up. He obliges, still clutching the soft fabric.
“Actually, Miss I can do something else instead, this is…it’s a bit much isn’t it? I mean it’s so girly…” His voice falters when he sees the smirk turning into a broad smile on Miss’s face. He knows he’s been defeated.
“I got you matching panties as well, go put everything on now, shoo shoo” Miss sits back on the sofa. Sissy stands there, considering his options, he sneaks a glance into the bag where, as Miss promised, there is a pair of ridiculously frilly panties. Sissy collects the dress and panties and goes into the other room to put them on, he half expects Miss to ask him to get dressed in front of her but she keeps quiet, playing on her phone.
Sissy stands in front of a full length mirror in the room as he slowly picks up the panties. His cage feels impossibly tighter, the humiliation is making him feel dizzy. He steps into the panties and pulls them up over the cage. He looks in the mirror and his whole face is bright pink, a shade darker than the panties. He turns around and there are so many frills in the back that his eyes instantly goes to his bum. He feels satisfaction mix with the humiliation, he does look quite good in this. Maybe he might as well own it.
Soon he finds himself all dolled up, the dress that Miss picked out leaves very little to the imagination and his frilly panties make the puffy skirt stand out even more in the back, he admires Miss’s choice. Daring to touch his cage through the many layers of tulle and silk. He doesn’t really know why as his cage leaves him frustratingly numb to the fingers but he finds it brings some sort of relief.
“I’m bored!” He hears Miss shout from the other room and he snaps out of it and enters the room where he finds Miss has also gotten changed, she is now wearing nothing but a silk gown in deep red and he sees the flicker of light reflecting off of the cage-key, hanging securely around her neck.
“Well look at you…” she coos and walks over to him. Standing close enough for him to feel her body heat and smell the perfume she put on this morning. He looks down and touches the skirt. She slaps his hands away playfully and walks around him, inspecting her choices carefully.
“That is sort of the point, isn’t it my lovely Sissy Toy?” She says, he can hear she’s smiling but is yet to look her in the eye. Miss reaches over and then she’s on her knees in front of him, lifting his skirts and pulling down his panties, he tries to see what she’s doing but can’t really see for all the fabric, he feels a tightness around his balls and then she stands up.
Miss takes his hand and leads him to the bedroom, perfectly made up as per her instructions. She lies down, spread eagle on the bed and sighs contently. Miss motions for sissy to come join her and he crawls over as she moves so that he’s between her legs. She plays with a silky ribbon on his shoulder before she pushes him down insistingly, he finds himself between her legs, he kisses her thighs, he knows she likes that. Miss leans back, one hand resting at the back of his head and the other one covering her eyes. He begins licking over he pussy, long strokes, short strokes and she moans happily. He can’t help but giving off a moan himself, he just loves pleasuring his Miss.
“Shhh, toys don’t speak.” She teases and pushes her hips towards his face, he sucks on her clit gently, feelings her legs vibrate from the stimulation. He hears a click and suddenly his whole cage begins to vibrate. He gasps and looks up, eyes wide, in Miss’s hand is a small remote control ring, which is now sending pulses down his cock, he groans but turns it into wonderful vibrations for his Miss.
Sissy is now lying flat against the mattress, trying to stem the vibrations hoping it’ll lead them away from his cock which is struggling against the cage.
He feels his Miss come against his lips, her hips pushing up against him in rocking motions. She calms down and he hears another click, she draws him up and he is now face to face with her, he can feel the warmth from her pussy against his vibrating cage and she looks up at him expectantly.
“Fuck me” she mutters and he starts rubbing against her opening his mouth to state the obvious that he can’t in fact fuck her like this, but then she whispers “if you make me cum again I might let you out of that little cage and you can fuck me for real… would you like that?” She asks, sissy feels a bit dizzy with all the different sensations, she pulls her gown further apart and starts playing with her nipples while he continues to grind against her.
Sissy leans forward, so eager to serve his mistress, he sucks on one of her nipples and she moans again. He feels his resolve beginning to crumble as the build up of there vibrator, the heat in his stomach travels downwards and his balls begin to tingle. He lifts his head, scrunching up his face.
“No way are you cumming now…” Miss’s voice echoes in his head and he tries to shake out of it as he feels his cock pulse with an orgasm. Inside the cage it feels different, like he’s not getting the pleasure of the orgasm but his cock is still twitching. Trying desperately to continue the pace to please his Miss as a few drops of cum leaks out of the cage, making it even more slippery between Miss’s legs. She moans and giggles at the fact he’s just cum in his cage and after a couple of minutes she has her second orgasm. Sissy lies down next to her and she props herself up a bit, stopping the vibrating ring and dangles the key to his cage in front of him.
“I can’t believe my toy broke down halfway…“ she tucks the key back behind her gown. “I guess I’ll let you out some other time… Not even a cage stops my Sissy, I’m almost impressed” Miss chuckles to herself as she drifts off to a very content sleep.
Sissy is mostly a well behaved sub. He does what I tell him to and loves pleasing me. He is incredibly enthusiastic. This is what we wanted to try to reign in. He would be my toy for the evening, purely there for my pleasure. He had been away for 10 days on a trip and during that time he had been instructed not to cum. As we both had been riling each other up throughout his time away…let’s just say Sissy failed.
Him being at my mercy for the evening seemed a perfect punishment and a great occasion to turn him into a life size sex toy, vibrations and everything.
I had set everything up. I had picked out his punishment panties for the evening: a padded pair of plush pink panties with bows at the front. I had lube, bondage tape and our beloved vibrating cock ring at the ready.
Now Sissy I believe was very excited about the idea of being tied up and completely at my mercy. He wanted to get started quickly (he is quick in many instances) I didn’t mind to indulge sissy in this – how often will you get a toy so willing to please?
He put the vibrating cock ring on, I had the ring at the ready in my bra. And then dressed up in the panties that I had picked out. Sissy did mention he felt a bit embarrassed about be
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