A Submissive Sissy

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 !


Sweatergirl Story

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Sissy Outing

Jodi sat on the couch looking at her Steve - a true Sissy slave who had been seeing her for three years and craved humiliation and degradation. It was a hot Thursday afternoon in late May in Washington DC. While many of her clients bored her, this one truly let her do whatever she wanted and she took full advantage of the opportunity.

“Sissy, today you are going on a little outing. I was talking to a girlfriend of mine, Beth, who is pretty vanilla, but she was very curious about what I do. I told her about some of my clients including you. She did not believe me that anyone would be so submissive. So I told her I would send you over to visit her. Doesn't that sound like fun?”
Before Steve could say a word, Jodi go on “It sounds like fun to me, Sissy, so it doesn't matter what you think does it?” Jodi giggled as Steve just stood and squirmed.

“Beth is a real estate agent, and she is sitting on new model homes on River Road, just 4-5 miles from here. So you are going to stop in at the model trailer and introduce yourself.”

“I know where those models are Mistress”, said Steve.

“Shall I just drive over there?”

Jodi looked at Steve. “First you need to look like a Sissy, strip you pansy” Steve blanked; he had not realized his Mistress was going to make him go out dressed as a Sissy.

Steve began to protest. “Do you have something you want to say Sissy?” asked Jodi. “If so it better be Yes Mistress or you won't sit for a week”. Steve just looked down at the floor. “Thought so”, laughed Jodi.
She handed the Sissy a lacy pink well padded bra. While doing that she took a pair of light blue wool tights and cut out the entire crotch and rear end. Jodi had the Sissy pull on the tights. His Sissy rear and little wee-wee totally exposed, framed by the wool tights. “It’s such a hot, humid day, so this should be perfect” giggled Jodi as she gave the Sissy a thick fuzzy hairy girl's mohair cardigan sweater. The sweater was cobalt blue mohair with little pink, red and purple fuzzy pom-poms. The neck, cuffs and bottom were much ticked ribbed darker blue wool, the sweater was cropped to hit just at the waist and it had big white clown-like buttons running down the front.
Mistress had made one alteration to the sweater- she had taken pink thick shoe laces and threaded them through the bottom front and back of the sweater from the middle about 5” on either side creating leg holes. The result was that in order to put the sweater on, Steve had to open the top buttons and slip his legs through each leg hole and pull the sweater up like it was a leotard. With the crotch and rear cut out of the panties, the itchy wool was pulled up tight against his ass and wee-wee. If you can imagine it looked like the Sissy was wearing a woolly leotard that button down through the crotch over tights!
Mistress added pink wool crew socks, pink sneakers with lacy shoe laces and thick white woollen mittens with tassels. Mistress wrapped pink tape around the end of the mittens and the Sissy's wrists so he could not remove the mittens. Then she took some thick pink yarn and tied his mitten hands in front of me so that he could just barely move his hands, but could not undo the tape on his wrists.
Pink “wet look” lipstick came next giving the Sissy glossy sexy lips. Jodi stepped back. “What is missing?” she asked herself. Then she turned and grabbed a big pink satin hair bow and clipped it on the top of the Sissy's head. “I think you are ready to go see Beth” laughed Jodi.

Mistress told the Sissy that her friend was a real estate agent and was currently working at a development of new homes out in Bethesda. He had to go out, visit her friend, and gets a signed note from her that he had visited her, modelled his cute woolly Sissy outfit and then come back to his Mistress. Jodi made it clear that she would not let the Sissy back inside unless he had the signed note. Jodi tied a pink little note pad using pink yarn around his wrist. She told the Sissy that her friend should sign the note pad as proof of his visit. Then she put a one heavier coat of pink “wet look” lipstick on his lips, and added pink dangling clip on earrings with little bells on the bottom on each ear.
Mistress asked if the Sissy understood his afternoon's task. “Yes, would you untie my mitten hands so I can drive?” The Sissy asked. Mistress looked puzzled for a second. “I guess you can't drive with your hands tied. So let me help you.” With a wicked grin she handed the Sissy a pink crochet little girls purse. In it were lots of quarters. “Sissies don't drive, they walk or take public transportation”, Jodi said as she laughed, “and that’s how you will get out to see Susan.”You will walk to the Metro station (which was about four blocks away) take the Metro to Frienship Heights stop, 2 stops and then go upstairs and take the bus that goes out River Road. The bus ride should be about 15 minutes, and the development is just below Wilson Lane on the left. There are no finished models but there is a large sales trailer, and that’s where you will find Susan. She drives a black BMW convertible, so if there is any other car parked in front of the sales trailer, just wait until it leaves before going in so as not to bother her while she is busy. I have given you just enough change to for Metro and the bus each way. Lose one of the quarters and you will be walking for quite a while Sissy.”
With that Mistress began laughing. It was about 2:30. “You best get going because Susan leaves by 3:30 and if you miss her you are in trouble Sissy.”
The poor Sissy began to protest. “Why of course you don't have to go, but no note, no returning your regular clothing. I wonder how you will get home and what your reception will be like in your woolly leotard outfit.” And the Sissy knew she was serious.

It was sunny and very hot as the Sissy left his Mistress. By the end of the first block he was very hot and sweaty, and the woolly mohair sweater itched something terrible. It also became obvious to the Sissy just how fiendish Mistress had been. The sweater was designed as a slightly cropped sweater which came just to the waist if one were wearing it normally. But now, with turned into a woolly leotard, the sweater was really stretched and tight between his legs. The itchy wool rubbed the poor Sissy's wee-wee, balls and rear with each step, in fact he could feel the rear of the sweater getting caught between his ass cheeks! And Mistress had cut all the crotch area out of the tights so as the sweater rode up with each step; it was like a girl in tight shorts showing off her ass cheeks! With almost each step the Sissy tried to pull the sweater down with his hands, which were in thick woolly mittens and tied together. If he walked too fast the sweater rose up higher, so the Sissy had to walk slowly much to his discomfort. If that were not bad enough, anyone seeing the Sissy could see his boobs and of course hear the earring bells tingling.
Luckily for the Sissy, not many people were walking around. A number of cars passed as he walked to the Metro, and a few slowed down to gawk. Two young mothers walking with their young children were on the other side of the street. When the Sissy past them they just looked and laughed.
The Sissy got to the Metro in about 15 minutes. His next problem was purchasing a Metro ticket. He walked up to the ticket machine, and standing in front of it, tried to open the crochet purse, but Mistress had tied it close with a knot! There were people in line so the Sissy walked away and stood in corner. He could not untie the knot with his hands in the thick wool mittens (and they were really thick and heavy!) but was able to pull the knot lose with his teeth. Then he fumbled trying to get the quarters out! He finally purchased my ticket and went through the turnstile down to the tracks. While he was aware people were looking at him, no one actually said anything.
But Mistress knew just what she was doing. The Metro station was right near a both a local public and a private high school. And while the Sissy was waiting, lots of students came to the platform. It took a minute for a group to come up to him, making snide comments, and then asking why he was dressed that way. The Sissy tried to ignore them but they would not stop. One of the boys, at over 6” and built like a rock compared to Sissy at 5'6”, pushed him and said answer the question . Just then a train came. The Sissy tried to walk away but this group followed him into the same car. When the Sissy tried to sit down, the same guy grabbed him and said “You should stand so everyone can see your outfit.” Once the train started they again asked why he was dressed like he was. “I lost a bet to some friends and this is the penalty” the Sissy sort of whispered. . They laughed at him, and said it must have been some bet. They made the Sissy turn around and model for a bit. Luckily for him the train ride was just 6 minutes, so when the train arrived at the station, the Sissy walked as fast as he could out of the train and upstairs.
Fortunately the bus he needed was there, but again he had to fumble for change. When he stepped on the bus, the bus driver, a woman, broke out laughing. Again the Sissy mumbled about losing a bet and having to wear this outfit as the penalty. A few other passengers noticed the Sissy, some looking away, a few laughing.
Finally after 15 interminable minutes the bus reached the Sissy's stop. The bus drivers seeing he was going to exit said in a loud voice “have fun!”

Getting off the bus, the Sissy saw the new development site across the road. The bus did not have the ac on, and it was hot and muggy outside. The Sissy was miserably hot and itchy with the woolly sweater caught up his rear exposing even more of his ass cheeks. His earlobes hurt from the dangling ear rings and the little bells kept ringing with each step. The Sissy crossed the road, which was a four lane road with a large grassy island in the middle separating the lanes. The Sissy could not walk very fast for fear that the sweater would ride up to expose even more of his rear. He was hoping Mistress's friend would quickly sign his notebook, so that he could leave. The Sissy knew he had to do the same trip back to Jodi's house. He desperately wanted to leave before rush hour fearing even more people would get to see him in his woolly Sissy leotard. However as the poor Sissy would soon find out, that was not to be.
The development site was one big construction area with new homes being built. The area was dirt as none of the homes were finished, though some appeared to be close. It had been a very rainy spring in the DC area so there was lots of mud and puddles. The sales trailer was set on a temporary parking lot, and to the Sissy's relief, Susan's BWM was the only car there. He walked in to the trailer, which had a main sales room and then what appeared to be a back area with a two offices. No one was in the sales room so he waited for a few minutes. Then Susan came out of one of the offices- she was in her early 30's, 6”, slim, with long blonde hair and quite attractive. She took one look at the sweatered Sissy and put her hand to her mouth. “You must be Jodi's Sissy.” Susan giggled. “I can't believe it. Jodi wasn't kidding about you. What an adorable outfit. Do you have a name?”
The Sissy stood there for a very awkward few moments and then said “Hi, Mistress Jodi calls me Pussie!!!! «Susan roared with laughter. “Pussie, God that’s perfect for you!!!!” He quickly asked Susan to sign his little pink notebook attached to his wrist to prove he had visited her then he would leave. Susan looked at the Sissy, “Not so fast Pussie!!!! I want to get a good look at you. She sat down, had him model for her, turn around a few times. Then she had the Sissy come stand in front of her. She asked if the sweater was as itchy as it looked as she rubbed it. He assured her it was. “Pussie, what do you have on underneath that adorable sweater?” The Sissy told her just a bra and tights with the crotch area cut out. Susan giggled. Then she wanted to know how the Sissy got there. The Sissy told her about his walk, metro and bus ride. Susan could only laugh some more. “Wow! I would hate to be you” said Susan. “You really must have given everyone a most memorable Metro and bus ride. Jodi told me how Sissy and obedient some of her clients were, but I did not believe her... But you are living proof” Then she asked if the Sissy knew his ass cheeks were on display. “Yes, I do” said the Sissy. She pulled the sweater down to cover his ass. Then Susan had the Sissy turn and face her again. “Pussie, what would happen if I opened this button?” As she put her hand on the second button from the bottom of the sweater, the one right over the Sissy's wee-wee.
He quickly pulled back, trying to avoid Susan's touch. “I would be exposed”. Susan laughed again. “Pussie, unless you are a very good Sissy, I promise I will cut off that button before sending you back to your Mistress! Then she took her phone and made a call to Jodi, telling her that Pussie had arrived, and how amazed she was that anyone could be so Sissyish and obedient. Then she laughed again and hung up.
”Could you sign my notebook so I could leave” the Sissy again asked. Susan sat backend, thought for a minute. “Not so fast Pussie, you need to earn my signature and I have the perfect task for you.”

Susan went to a closet and took out a pair of black knee high leather boots that were covered in dirt and mud. “I wear them almost everyday to take potential buyers through the development. Don't you think they need to be shined Pussie?” asked Susan with a giggle. The Sissy just nodded his head. thinking that having to shine the boots would be quite a task, but if that is what he needed to do to get Susan's signature, well ok. “I guess you want me to clean them up” said the Sissy. “Yes.” said Susan. Then she started walking toward the door. “I don't want any mud in the sales trailer so Pussie you will have to shine them outside. Standing outside in the hot sun was not going to be fun in his woolly sweater, the poor Sissy thought, but whatever to get done and leave.
Susan pointed out the door. “I don't want you hanging around here Pussie!!!! Its not good for business for a Sissy dressed in a little girls wool sweater leotard to be around. So what you are going to do is go walk across the road and stand in the middle of the grass island and clean the boots there.” Oh no thought the Sissy, now he would be standing on a 10’ wide island on a major road with lots of traffic shinning boots, dressed in a horrible hot itchy outfit. Before the Sissy could say anything Susan then added “I don't have any brushes or towel, so you are going to have to lick off ALL the mud, dirt and whatever else are on those boots and then spit shine them. Jodi tells me you are good at licking toilets clean so this should be no problem, right Sissy?”
The poor Sissy gasped as Susan just laughed at him. “Get going and make sure the boots are shinning with any bit of mud or dirt before you came back. If I find so much as one speck of dirt, I will not sign your little Sissy notebook. Any dirt and she would not sign his notebook. “I will be watching so you better be an obedient boot licking Sissy.”
The Sissy did not have much choice. He took the dirty boots in his woolly mitten tied hands and slowly walked across the two lanes to the grassy island. There he stood in his thick hot itchy fuzzy sweater leotard, in the middle of a major road on full display with no where to hide. The Sissy's only thought was to get the boots cleaned as quickly as possible. He put one down, took the other in his tied mitten hands and began shaking it to hopefully loosen some of the mud and dirt. As his hands were so tightly tied together with the thick mittens he found they were useless. Then grimacing, he brought the muddy boot up to his face, rubbing the boot on his nose to get off the dirt. That helped loosen just a little of the dirt. Finally, having no choice the Sissy began using his tongue to lick the mud off. Soon his mouth was filled with dirt and mud. The poor Sissy was soon sweating, the sweat dripping down his face and body. As the sweat dripped, it damped the fuzzy itchy mohair sweater, making the Sissy even more hot and itchy. He heard some car horns, and saw a few cars slow down to look at him. . A few people yelled out comments like “You can lick my ass next” or “Do my boyfriend's cock next.”
When the Sissy finally got the first boot clean, he began to spit shine it. His mouth was soon dry, and he could not spit out all the mud and dirt. Satisfied that the boot was perfectly spit shine, the Sissy began working on the second boot. By that time, he was miserable, feeling totally degraded and abused, not to mention hot and itchy. He did not realize it but he was now squirming back and forth to try and relieve the horrible itchy feeling between his legs. As he squirmed the sweater pulled up further into his rear crack, and his cheeks were almost fully on display. He sighed and went to work on the second boot, which looked to even more dirty than the first.

Another 30 minutes of licking, getting mud in his mouth, squirming in the hot sun as the itchy sweater riding up higher into his rear, sweat pouring down, the Sissy finished the second boot.
By that time, the poor Sissy was miserable and felt totally degraded and abused.
Looking up, he saw Mistress Jodi drive up to the trailer. In a few minutes both Susan and Jodi came out of the trailer and walked over to him. They both laughed when they saw what a sight he was, his face covered in mud and dirt, sweating, squirming to try and relieve the horrible itching from the sweater, holding the now shinny boots with what was a most pitiful look. “It sure is hot” said Jodi. “Yea,” said Susan, “definitely NOT sweater weather”, giggling. Then Susan took her boots and to my shock dropped four pair of smaller muddy rubber boots at my feet. “I use these for clients”, Susan said, “don't you agree they should be cleaned as well Pussie? Well I really don't care what you think Sissy; I want them cleaned up before you leave. Its really hot today so your Mistress and I are going to go out to get some cool refreshing sodas while you finish your chores” laughed Susan, tormenting me even more.
Jodi looked the Sissy up and down. “You aren't very excited to see us, are you Pussie?” looking straight at where the Sissy's wee-wee was under the sweater. “That’s rude Pussie!!!!” she said. “You had better get a nice tent up in that sweater before we get back or else. You can rub yourself with those mitten hands or maybe hump the boots- that will be a bit less obvious to the on-going traffic but we best see a nice bump there.”
Then Susan giggle and whispered to Jodi. Jodi got an evil grin on her face. “Great idea Susan, tell the Sissy.”
”If when we return we don't see a nice big sweater tent, you will have to walk back to Mistress's facility, your arms tightly bound behind you and the button on the sweater where your wee-wee is taken off. But that won't be a problem for you, Pussie since if you can't get your wee-wee hard enough to make a tent, that means there is nothing to see!”
With that Susan handed him one of the rubber boots. “Oh by the way yesterday a client wearing one of these boots stepped in some doggy pee and poopoo. Enjoy your treat Pussie while we have our nice cold drinks!”

Jodi and Susan left the Sissy standing in the grass, with two more sets of muddy boots to lick clean. He just stood there for a few seconds watching as they got into Susan's BMW with the top down and drove away without so much as a glance . The Sissy knew he had no where to go. His Mistress's facility was about 5 miles away, and there was no use going there as Jodi had his clothing and car keys. So he did the only thing he could, picked up one of the rubber boots and began to lick it cleaning. Standing exposed on the island, he heard some more cars honking their horns.
He began licking the rubber boot. At least the rubber seemed easier to clean then Susan's leather boots.
Then the Sissy remembered about having to keep his wee-wee hard. His first thought was that Mistress and Susan had gone for a soda so they would be gone for awhile, but then he thought what if they surprised him and come back quickly just to check up. One thing about Jodi was that she never made threats. If she said there would be a punishment or penalty for not obeying her orders, the poor Sissy knew that is what would happen. He did not want to just stand there and play with himself so instead he pressed the boot against the sweater where his wee-wee was and began rubbing against it. He was sure he looked ridiculous humping the boot in the middle of the road, but soon he had a bit of a sweater tent. So he went' back to licking the boots.
On the bottom of the last boot there was what looked like dog poo. The Sissy could not shake it off or rub it off with his tied mitten hands, so he had no choice but to rub the boot against his nose to finally knock the poo off. It smelled and some of the poo stayed on the tip of his nose. The Sissy could not get it off. He was trying so hard to shake it off that forgot about keeping his wee-wee hard.

“Well are you done?” The Sissy had not seen Jodi and Susan who had walked up behind him. He quickly bent down, grabbed the two pair of boots, licked clean, and handed them to Susan. His mouth was totally dry and filled with bits of mud, his face covered in dirt and sweat, dog poo on his nose. “Is that dog poo on your nose?” Susan wanted to know, laughing at him.
Then the two women walked toward the trailer and told me to follow them. The Sissy was hoping that he was now done and that Jodi would drive him back to her house. For the poor Sissy, no such luck.

The Sissy slowly walked to the trailer office. “Stop, Pussie, you are way too dirty and smelly to come in here” said Jodi. Then Susan looked at the Sissy and whispered to Jodi. “Jodi looked at the Sissy, where is your wee-wee? Didn't we tell you to make that little thing hard as a sign of respect?” The Sissy only looked down, having nothing to say. “Take out your wee-wee and balls so Susan can see that they are really there” Jodi said. “Ok Pussie, entertain us, pretend those tied woolly mitten hands are a pussy and put your wee-wee between them and hump until you cum. “The Sissy's face turned red. Susan giggled as she and Jodi sat down to watch the show. The Sissy began humping the wool mittens. Susan went inside, and turned on some music. “Do it to the music Pussie, dance and play for us.” she said. So the Sissy humped to the beat of the music as he did a bump and grind for the women. His earrings were jingling, his wee-wee getting sore from rubbing against the coarse wool mittens, and sweating in the thick itchy wool sweater which was riding further up, exposing his rear cheeks to passing by traffic. “Shake it Sissy” laughed Susan, make that cute rear bounce for us and anyone else who can see you. I want you to cum into those mittens” said Jodi. “Catch every drop in those mittens or else!” It took a few minutes and the Sissy began to spurt. “Get all those Sissy dribbles into the mitten.” giggled Susan.
When he was done, Jodi pushed the Sissy's wee-wee and balls back and rebuttoned the sweater. “Hold those mittens out so no cum drips” said Jodi. Then she got a wet towel from inside the trailer and gently wiped all the dirt from the Sissy's face including the poo on his nose. The Sissy thought this day of humiliation was finally going to end.
But he was very wrong.

Jodi grabbed the Sissy's wrists and began rubbing his c-m covered mitten hands all over his face “A cum facial” giggle Susan. Jodi stood back, “Do you remembered what Susan said would happen if your widdle wee-wee did not show us the proper respect when we came back?” The Sissy could only shake his head. “And you know I always do what I say, isn't that right Pussie”. With that Jodi pulled the Sissy's arms behind his back. She gave Susan a role of masking tape and had her tape the Sissy's arms together; Susan laughed as she tightly bound his arms in back sot that his elbows were touching each other. Then Jodi tightly retied his mitten hands together
Jodi then reapplied some fresh pink lipstick. With the Sissy's arms tightly tied in back the itchy scratchy sweater now was pulled tighter, his “boob” sticking out even further and the coarse wool rubbing even more his wee-wee and rear. “I was going to let you take the Metro and bus back, Pussie” Jodi said, “but not now, now you can walk.”
Jodi looked for a moment at the Sissy. She giggled, whisper something to Susan. Susan went to a closet and came back with some more really coarse thick rope. Jodi tied the rope around the Sissy's wrists, pulled in down, pushing the sweater away and threading the rope so that it was wedged deep into the Sissy's rear end, then she continued to pull it tightly through his legs, tying another loop around his balls, and then up, threading it under the sweater up his chest, “Susan please hold this end for a second” Jodi asked as she stepped outside to her car. Jodi was back in a moment holding a pink leather dog collar with a “D” ring in front. She put the dog collar on the Sissy’s neck, buckling it nice and tight. Taking the end of the rope from Susan, Jodi yanked it hard, pulling it up tighter through the Sissy's rear and tied it to the dog collar ring. “That rope should feel soooooooo nice rubbing up and down between your rear cheeks as you walk” said Jodi. She then carefully pulled the sweater down to cover his rear and front.
Before poor Sissy could say a word, Susan walked up to him. Smiling at him she slowly opened the second button from the bottom of the sweater and spread the sweater apart. “See I was nice to let you cum” said Jodi, “your wee-wee will be less likely to pop out of the sweater now!”
Susan roared with laughter. If that were not enough, Jodi took the Sissy's little crochet purse, walked behind him “Grab the purse with your hands Pussie”. As the Sissy did so, Jodi added”you better have that purse when you get back to my house”. Susan looked “Pussie I wouldn't drop that purse because if you try to pick it up I am sure your wee-wee will just pop out!”
”Ok Pussie get going” Susan chimed in, “I would walk very very slowly with very small steps if I were you Pussie. The sweater is very thick and with small steps your wee-wee should stay inside the sweater. And with your arms bound up in back, if your wee-wee does come out, well there is no way you can tuck it back in!! With that Jodi and Susan each gave the Sissy a hard slap on his rear and laughed.
It took the Sissy over three hours to walk back in the heat. He knew he could not walk on the main roads, so he took the back streets. As Susan had said, he walked with very small steps stopping anytime he felt his wee-wee starting to push out of the sweater. Lots of people saw him, some in cars and walking. A few people came up to ask what he was doing, so again said had lost a bet and this was the penalty. Lucky for the Sissy his wee-wee never came out!
I made it back to Mistress's facility. He was totally exhausted, miserably hot and itchy and yes totally humiliated.
But the worst humiliation was left for last. He rang the doorbell; Jodi came to the door and looked at him. She let him in and took him to the den. There was Susan and another woman. The Sissy gasped, it was Brit, his wife. Britney walked up to him and just looked. “I knew you were into submission, but never anything like this” she said. Jodi has been telling me all about your “interests”. Don't worry, Pussie, I am not going to make you stop this. No, in fact I like the fact your are this submissive. And I can assure you, you will soon realize that today was the least humiliating day of your life”