Sissy Bondage Story

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Sissy Bondage Story
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Femboy sucks dildo in parking garage.
Jake's day off becomes interesting.
Dystopian Sci-fi for the modern submissive femboy.
Sissy tan lines after visiting daddy.
Finger fucked in public was only the beginning.
The sexual adventures of a submissive sissy.
Archie is taken to his first rave as Kelly.
Rory goes to College, and finds help in an usual way.
You do meet some beautiful people out on the open road.
Sissy Adam trained to accept nectar.
Sissy expects another threesome but is gangbanged instead.
Andy begins to accept his sissy side when he meets Anna.
Cassie confronts her attachment when Anna grows distant.
Sissy has a fourth threesome with bondage and beating.
Continuing story of one possibility.
Sissy has a third threesome with painful bareback anal sex.
A submissive returns to his goddess after a year apart.
Dafni struggles to free herself and flee her nightmare motel.
When your life changes and you don't know what to do...
Maid is released from her training machine and put to bed.
Liam get's another night with John and Trevor.
Maid gets cleaned out and shackled to fucking machine.
Denise's high stakes dinner for Joey with special dessert.
A road rage incident leads to life changing events.
Eric was a normal college boy, until an incubus got bored.
The new master gives a tour and duties to his new sissy maid.
Our online lovers meet for the first time for kinky fun.
Miss Sarah's party finally gets underway.
Mike becomes Michelle in this sleepover Sissy tale.
The summer Christmas party gets a little out of hand.
Man is captured to become sissy maid, fuck toy.
Man is kidnapped in to a new sissy life.
The sexual adventures of a submissive sissy.
To avoid being a sissy, I need a friend's help.
Am effeminate young man is mentored by an older woman.
Mia meets an older man in a hot tub.
Part 2 of Straight Boy Fucked By Two Bulls.
Sissy has to lose weight so becomes a cumslut for a week.
Sissy has a second threesome involving rimming and piss.
Husband cuckolded side by side with his wife.
Mistress Kristy's second session with Vic.
Sissy surprised by Mistress' lover.
Madison's humiliation at the hands of Hally goes public.
Straight guy is lead unexpectedly into his first experience.
Mistress brings home a lover to share with sissy.
Sissy slave brings Mistress home for the week.
Michelle's long night continues, but he learns her lesson.
An ex-con's past comes back to haunt him.
Ashley's plans for Dolly are interrupted by Rose's return.
Seductive, sexy and silky sissy teases and tantilizes lover.
Sissy housemaid duties and teased all night.
Grace wants to make Margret’s Dream Come True.
A femboy, a Daddy and a club again.
Markus pursues Shireen. Darius fully embraces sissy slavery.
Trina saves me from Louise's father.
A sissy get trained by an older BBC.
A new Mistress, a new job. How far would Rory go...
Patrick gets blackmailed by a mysterious man.
Work progresses. Even on a days off.
Tommy and James add his dad to the mix.
Learning from the old coworker to have fun solo or together.
I was looking for a mistress. I guess I got what I asked for.
A sissy house 'girl' is used at lunch time.
Accidentally a cheerleader at the basketball party!
First time called a sissy and serving at a party.
College Freshman Sami goes home for winter break.
A house-sitting job leads to a new direction.
Honestly, Kojima probably *did* think of this.
They transitioned me into a sissy gurl for a CIA undercover.
The sexual adventures of a submissive sissy.
Lotty taken for a night out, is shown a lifestyle of fantasy.
Freshmen at college finds anal comes with much more.
Maddie goes from daddy’s girl to whore.
All contents © Copyright 1996-2022. Literotica is a registered trademark.

Send a Private Message to Tiedandgaggedsissy
Hello, i'm Sissy Doll, a 26 year old sissy/crossdresser, I’m owned by my beautiful Mistress and I have a love for tight bondage, forced feminization, pegging, crossdressing, female domination, humiliation and ABDL. You can see me in my #me tags. Feel free to message or ask questions anytime!
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It’s been a few weeks since you told your wife about your fantasies of being a sissy cuck “husband” and now you’re all dolled up, ass plugged and playing with your clitty, meanwhile she is in the other room throwing away all your male clothes to have them replaced with dresses, corsets, panties and heels, but remember sissy.. this is the life you asked for.

Chapters


A fantasy playday gone wrong





The Fantasy Play Day Has Arrived





From Bad To Worse In Less Then A Day





More Complications?





The Conclusion



Here you'll find my favorites Sissy & Femdom stories, the best one I've ever read over the net since many years and believe me, that's a lot ! I'm also a wool fetishist, so you may come accross this type of topic around here too... Hope you'll like it !
Hi my name is "Rick", but some people like to call me Ricky; I ëm 35- years-old, and kind of on the short side, ok the really short side. I stand about 4ft.-7 inches tall and weight about 95lbs. I'm the head or if you want, the president of a small insurance company in our town, which my wife inherited from her late father. It's a small company that my wife lets me run for her as I see fit, while she works at her job, as a paralegal for some big shot lady lawyer in the city. She makes twice the amount that I bring home from the company, but I have fun running the small office, plus it keeps me busy and out of trouble. I have 6 really cute looking ladies that work in the office under me, and I will say they all have a pretty nice looking shape. I should know I hired most of them, except for Jennifer, and Sally, who were with my father-in-laws company, before he died and I took over. All the ladies are in their mid twenties to early thirties. As for my wife Jackie she is 34 years old, and what a knockout shape. She has one great looking body weighting in at about 135- lbs, and her measurements are, 38D-30 ñ36. One draw back is she happens to be lot taller then I am. Jackie is about 5ft-11-inches tall, which is almost a foot and a half taller then I am. So I guess you could say we look a lot like Mutt and Jeff from the old comic strips.
I must confess that lately the wife and I have not been getting along as I would hope, and I have this sinking feeling she has been seeing someone else on the side. I've been trying to find out, whom if anyone, but I still have no proof. I have even asked Jennifer at work for some help finding out whom she may be seeing. I had asked her if she could try and find out if Jackie had someone else on the side for me. You see Jennifer has known Jackie way longer then I have, because she and Jackie both worked for Jackie's father, when they were in their teens in high school. As of now Jennifer has come up with nothing yet, which I guess is a good thing. So I have given up checking up on Jackie for now, and have decided to start looking around myself just in case. So far I have asked out a two of the cute ladies at work, which I know is not a good idea, but I needed some sex, as Jackie seems to have also cut me off lately. Jennifer was the latest one I asked out, I mean she is really cute looking and is about my age, but we never really got anything going between us. I guess you could say both so called dates I had with her; really ended up being more like business meetings then dates. I think the main reason was that we ended up talking about the company, and how she thinks some of my ideas were ruining it. So she started telling me how if she ran the company she would do some things a lot differently. Most of the two dates I had with Jennifer went pretty much like that, with her telling what I should or shouldn't do. I will say this she did have some good ideas. So I guess the time spent with her wasn't all wasted, and you could say it was a couple of fun and interesting nights out, even though I never got any sex out of the deal.
What's got me worried right now is I've been dating one of the other girls in the office, but only a couple of times. I really like her and we have hit it off nicely. Thing is what if this gets a little more serious, and it turns into a full-blown affair? Then what would happen if I break it off with her and she gets mad at me? Then I would have to worry that she may go and tell Jackie about us. Jackie has no clue about what's going on with that girland I. Plus what if this girl finds out about the books, and decides to tell Jackie what she found just to get even with me. Jackie trusts me to run the whole place my way, and has no idea of what I have been up too. To be truthful I've been embezzling funds from the company, well not really embezzling more like taking a little money here and there. I needed some extra cash to have fun, when going out sometimes, and also to buy my self some nice looking outfits.
You see I'm also a crossdresser, and have been since I was 6-years-old. Jackie has known all about my crossdressing for many years, and she is somewhat ok with the idea of me in skirts, as long as I do it secretly at home, or at one of the crossdressers club meetings. But if Jackie found out about my secret stash of money! Oh My! I would be in some really hot water for sure! I mean if she found out about me seeing another girl, plus me taking money from the company? I know she would kick me out of the house and get a divorce, or even worse she could even send me to jail if she wanted too. Then where would I be, maybe some guys babe in jail, and I don't like that idea at all. As it is about 6-months ago I had already stopped taking the money, mainly because I figure I had enough put away, so why push it.
One of the main reason I took the cash was because I don't get that much of a paycheck from the company, and what I get we use to pay all the bills. So by time I pay the bills at home, it leaves me with only a few dollars a week to spend on what I want. So that's why I've been stealing money here and there from the company. Not much money each time, but just enough to keep me going. I have been putting it in a special checking account under my name. The money is just so I can have my own stash for whatever I want to use it for, and when I want to use it. The way I look at it in a way it's partly my money anyhow. Plus I haven't taken that much, maybe about 10 to 12 thousand over the last 3-1/2 years. I sure don't want that to be found out by any of the girls in the office. If they did I know it would get right back to Jackie. That's why I really haven't got to serious with this one cute girl I've gone out with. I can't take the chance that's he would find out about the money.
What got me was getting that little stash of money really wasn't that hard to do, but then making sure no one knew about it, now that was the hard part. Being I run the company and I take care of the books. I did find it kind of easy to hide the fact that I was taking the money from the petty cash checking account. I figured the easiest way was to buy things for cash or a check made out to cash. It was really kind of simple, and actually it all started by accident. Seems one day I ended up with cash in hand after I had made a check out accidentally for more money then the items really cost. I was at STAPLES and had made the check out for $50 dollars more then I needed too. So the cashiers gave me back the change. Wow I said to myself that's kind of neat, I could skim off some money a little at a time like this and have myself a little spending cash.
All I had to do was make out some fake purchases orders that equaled up to what I put down in the accounting books. Then I would take X amount of cash out to spend on the items I needed. After buying what I need for cash I could deposit the extra money into my personal checking account making sure to have some fake recites for the full amount. I wouldn't take much money maybe $30 To $50 dollars at a time. The books would say I bought such and such items at so and so price. I could do this with most of the stuff for running the office, like copy paper, office supplies, printer ink and the copier toner. Then I could also write some larger checks for things that I figured you can't trace, and are used up real fast. So that's just what I started to do, and after a while I had a good size nest egg. I will say I was a little worried, and also a little up set about having to resort to stealing just to have money of my own, but Jackie makes it hard for me to have any cash of my own. She likes to be the one in control of everything, even our money, and makes sure she knows just what money goes where.
Let me fill you in on a couple other things that I'm also keeping from Jackie, which I really don't want her to find out about. Like I had said earlier Jackie already knows about my crossdressing, and that I go out dressed to meetings. The only thing she doesn't know is besides my dressing up as a lady, I have another secret side to my crossdressing life style. It's a secret that Jackie I hope has no clue too. You see just for the fun, whenever I'm in the mood and I have the chance too, plus I know Jackie is going to be away on one of her two-day or more business trips with her boss. I love to dress up as a little girl. I like dressing up as a little girl who would be maybe 3-years-old. Then again there are also some times I may dress up in a cute frilly baby girl outfit, and pretend to be a little baby girl who is about 18-months to 2- years-old, wearing diapers, rubber pants, with a baby bonnets, using a pacifiers, and all that stuff. It all depends on how I feel and the mood I'm in at the time.
I guess you could say that this thing for little girl's outfits started back when I was about 8-years-old. You see my mom uses to dress me in frilly lacey little girl outfits that were designed for a 3-year-old little girl or younger for punishment. She was a great seamstress and could take a little girls frilly dress pattern, and enlarge it to fit me. She kept this punishment up till I was about 16-years-old and in high school. I guess she did it to keep me under control, because after my dad died, when I was about 8-years-oldI I really started getting into a lot of trouble. I pretty sure that's why I'm still hooked so bad on the cute little girl and baby frilly outfits. Plus because of that punishment, I also love to read forced petticoat discipline and punishment stories. These are stories in which some guy or young boy is forced to dress as a little girl, baby girl or even as a French Maid, by the wife, girlfriend, or even the mother. Most stories are about an adult male who was caught dressed, or maybe the wife or girlfriend is getting even because she found he was cheating on her. Then again maybe it's about a teenage boy, or preteen, who is always getting into trouble like I did. So he is being forced to dress as a little girl or even a baby girl by his mother to get him back under control, just like my mom did to me. I sometimes like to fantasies about being one of the guys who is being punished that way. Hey it doesn't hurt anyone and it releases a lot of stress for me. One of my favorite things to do is dress up as a little girl or baby girl in a really frilly outfit, and read these stories while dressed.
Sometimes I even think about maybe recreating parts of the stories that I read. You know try to live out one of the scenes for my self. I'm pretty good with my hands and power tools. I've even made, just for fun, an adult size highchair out of hardwood, with a tray that fits and locks in place. I then painted the chair all white and padded the seat and backrest with thin foam covered in fake pink leather. Plus I even attached straps to it for your ankles, wrists, and around the waist. They're attached to the chair to keep your hands, feet, and body locked in place, making the person in the chair helpless. Once you are strapped in your mistress / mommy / wife, or whoever has complete control over you, and you're stuck setting in a highchair. Right now I have the chair concealed way in the back of the basement, over in the far corner. I made the highchair just so I could try and live out one of the fantasies that I read about in a story.
The one problem I found with that idea was you need someone else to role- play with you to truly have fun using the chair. You really need to have that one extra person you can trust to role-play with you. Someone to play along and strap you in the chair while you're all dressed up, because using the chair alone you just don't feel like its any fun. That's why I have only used the highchair once or maybe twice, mainly to take some pictures of myself setting in it. You see I have no one to role-play with, as Jackie has no idea of this side of me. Plus I already know that she wouldn't role-play as a mommy or mistress, it's just not her if you know what I mean. So now the chair just sets there in the basement covered over gathering dust. Matter of fact I plan on taking it apart soon to get rid of it. At one time I had even thought about selling it on E-Bay, but didn't know how I could ship it to whoever wanted to buy the chair.
The one time that I used the chair to take pictures I had dressed up as a little baby girl, wearing a baby bonnet, with a pacifier stuck in my mouth I took a whole bunch of cute pictures in all kinds of different poses. In one I was setting in the highchair, while wearing a large pink frilly baby girls dress, with a crinoline and cute frilly rhumba panties. I had a baby's plastic bib over my outfit, holding a baby bottle, and eating out of a Disney Princess bowl. Then I took one or two of me just setting in the chair in my outfit holding on to a doll, while still sucking on a pacifier. What's great is I have this digital camera that has a remote control for it. So I can set it up on a tripod facing the highchair all set to take pictures. Then get in the chair making myself all prettied up and ready. All I have to do is then hit the button on the remote, and 10 seconds later poof the camera goes off, and I have a digital photo of a cute looking baby girl in her highchair. Anyhow after I took tons of pictures using the chair, I kept the 12 or so best ones, then I hide the chair away in the basement. This way I know where it was just in case I ever want to use it again.
The reason I built the chair was because of a story I had read, which had this poor guy being treated as if he was a little baby. His girlfriend had him strapped into an adult highchair, and she was feeding him his dinner. Only the girlfriend had put his whole meal through a blender, and turned it into purÈe type baby food. Whether it's being turned into a baby girl, or little girl, or even a French maid, I love reading all those type of stories. They really do turn me on. One of last stories I read was about a guy who was caught playing around by his wife, and because she no longer trusted him, but still loved him. She decided not to divorce him, but to get even some how. So she confronted him about his cheating. He broke down and told her everything, and promised that he would do anything s
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