Making Of A Sissy (Part Four) free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
After work the next day I met with Linda and my sister, Susan. I told both of them that they are more than welcome to come visit anytime they like. I gave my sister the key to my sissy's cage and told her not to share it with him. I encouraged them to call him "sissy" from now on. I told them that they would play an important role in helping me to bring out the inner gurl in my sissy. Over time they would see what I mean. I told them that there would times that I would call upon them to assist in his training. They asked questions about their role and I told thme I needed their help if I was not around or if I just needed a third person during the training. I told them that this weekend I was going to go out and that my sissy would be home alone most of the weeekend.

The weekend was aproaching fast and when I returned home form work Thursday I sat my sissy down in the kitchen and told him that I had a date arranged for Friday night after work. I will be going right out and will return later Friday night, hopefully. He sat there with a disappointed look on his face. I asked him "what was wrong?" I said "you know I worked all week and I deserve some play time on the weekend." He said "I thought we would have playtime here." I said "oh and how are your household duties supposed to get completed if you have playtime?" He didn't have an answer and so I said "now we understand each other."
I asked that he make sure my business suit outfit be ready for Friday morning, since I needed to wear that to work. He asked "what color blouse I wanted to wear with it?" I told him "forget the blouse i will just wear the jacket."

Friday morning arrived and I dressed for the beginning of the work day. A blue business suit with dark blue pumps with knee high nylons. My sissy had made me lunch and I came down to breakfast. Upon eating breakfast, I gave him a kiss on the cheek and reminded him that I was going out after work. Before leaving I jotted down some notes, for the babysitter. I didn't know who would be able to sit the sissy while I was gone for the night. My instructions included showing the sissy a video, from my collection, of a collage of males sucking cocks.

At work some of my co-workers were discussing their usual ritual of going out drinking after work. A former lover and co-worker stopped by my office to ask if I was going to join them tonight. I confirmed I would and he smiled and said "finally." After some joking around it was back to work until the final bell. I called my sister and asked her if she would sit with sissy to keep him company. She said she could. I told her not to let him out of his cage because he was in training.

Once the school was empty I was able to lock everything up and let the maintenance department know that the building was secure. I drove to the bar were the others were starting off their weekend. Upon entering everyone gave me a big greeting as I made my way to the area where my former lover was standing. I walked up behind him and slipped both my arms around his waist from behind. He is an African American man, standing 6' 3" and over 230lbs. Chocolate brown skin tone and so handsome. "Well hello, I guess", he said as he turned to see who was grabbing him. "Heyy", he said as he bentdown to give me a kiss on the lips. "Its nice to see you make it", he said. "Its nice to be here with friends", I said. For the next four hours we made small talk about work, our lives, and about the night. Within those hours many of our co-workers had made their way home. I change our conversation back to when we were an item. I came right out and asked him if he would like to pick up our affair where we had left off. He smailed and gave a slight chuckle. "Well what would your hubby thing about that?" he asked. "Well he doesn't have to know", I siad. He siad "Thats like playing with fire then." I said "no not really because I don't think he would mind." "Well then tell me why did you stop the affair after getting married?", he asked. "To be honest I was doing it for my hubby and today I can honesty say I am doing for my hubby." He had a questionable look on his face. I said "look I wasn't going to say this but my hubby....lets say he had other desires." "He cheated on you?" he asked. "Oh no not that. He desires to be more feminine than a man." I said. He gave a smile and chuckle. "Well now you are looking for someone for him?" he asked. "Nooo just looking for someone who can give me want to want and need." I said. With that said he asked if I "wanted to get out of here?" I gaved him my bag and coat.

I followed him in my car to his place. We entered through the basement door and I followed him to the second floor. I took my coat off and made my self at home. Hech I was here so many times before it felt like home. It wasn't long before we were kissing on the couch. I wanted to move right to some foreplay and started to unzip his pants. He kept pushing my hands away but not forcefully. I was able to get his cock out and I when down on him. OMG I thought, how I miss sucking cock. I told him it has been a while since I did this. He said " you are doing fine baby." I continued sucking the head and down the shaft. After a few minutes I think he could tell I was horny. I deep throated his 8in cock a few times and was stroking the shaft as I edged him with my lips. He said lets move this to the bedroom. Once in the bedroom with undressed each other taking time to touch and lick each other as we did. Once naked we found our 69 position and I was once again sucking his cock. I was on top and my head was working his cock over good. I could feel his fingers and tongue inside my pussy. Damn I had missed this so. He could sense I was very horny and soon he was talking to me and reaching down to push my head down on his cock. I crawled up on top of him and started to kiss him. My legs squeezing his cock which was standing straight up and hard as a rock. I sat up on him and leaned back so my ass cheeks rubbed his cock. He was telling me to slow down he was going to cum too soon. I laughed and said I know you sweetie you have a lot to offer. With that I grabbed his cock and guided it to my pussy. Leaning back my pussy swallowed his cock. I didn't hesitate I just started to ride him. He got right into in once deep in my pussy. We both shared several orgasms in the hours we were together.

At 11 pm I called my house. The sissy asnwered the phone. I told him I was ok but I would be a little late. He asked where I was because it was quiet there. I told him with a friend. He asked if I was having fun and I told him we were. My sister got on the phone and I told her she should go home because I would be late. I asked her what was going on there. She said the sissy was begging her to unlock him. She also told me that she played the video and he seemed uncomfortable. She realized his cage was stopping him from getting hard. She said she had him lower the front of his panty so she could see. She told me that she used a finger to rub his cock inside the cage. She had him lick her pussy and that she could see his limp dick was leaking cum into his panty. I was hesterical and grateful for her teasing my sissy and humilating him.

Same as Making of a Sissy (Part Four) Videos

3 years ago
  • 0
  • 28
  • 0

My girlfriend made a sissypart1

Hey guys this is my first story ....hope you all like it ...When I was 18, in spite of my shyness and not being in anyway incrediblyattractive, I somehow landed myself a girlfriend 2 years older than me. Iwas quite short for a boy then, around 5'7 and very slim having not yetdeveloped much muscle. I had shoulder length brown hair and bright greeneyes and I simply couldn't believe my luck in getting this girl. She wascalled Jess, a beautiful redhead with a body to die for and an appetite forsex...

1 year ago
  • 0
  • 21
  • 0

Sissy Farm Chapter Four

Sissy Farm - Chapter Four By: Beverly Taff List of Characters. Me: Michelle, a natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistres Janet: Headmistress of the young lady's academy; Doctor Shirley Williams: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: My transvestite uncle. Chapter Four When we arrived...

2 years ago
  • 0
  • 21
  • 0

Sissy Farm Chapter TwentyFour

Sissy Farm - Chapter Twenty Four - ByBeverly Taff List of Characters. Me, Michelle: A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Doctor Shirley Williams: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine, AKA Uncle Penny: My transvestite uncle. (Aunty...

1 year ago
  • 0
  • 14
  • 0

Sissy Puppy Fifi Part2

Chapter 2 I tried as best as I could to get comfortable curled up in the corner of the room. At first I kept squashing my tail which either caused the vibrations to start or pushed the plug further inside. I had eventually worked out the best position to lie in when Mistress appeared. "Time for bed Fifi," she said as she attached the pink lead to my collar. I was then led through the house and up to her bedroom. This was a strange feeling to enter her bedroom not in my usual maid's...

3 years ago
  • 0
  • 18
  • 0

Making of My Sissy Part Two

It was then that I pursued my own physical satisfaction from a former lover and co-worker of mine. I always had a thing for black men since most of my life I worked around blacks. It was many years prior to my marriage that I was dating a fellow co-worker, who happened to be black. Everyone at work knew we were dating. Then I met my husband and the dating had stopped and I devoted my life towards my new love. Finding out that my hubby enjoyed playing as a gurl has changed my outlook on my own...

2 years ago
  • 0
  • 17
  • 0

SISSY DANI PART3

CHAPTER THREEMistress Jennifer and Mistress Susan's plans to create an entire"harem" of transformed men and boys continued apace. The lure ofTeasing Tammy (the transformation name of Susan's teen-agedbrother Tommy) proved quite effective. Each of the young men (theyoungest just 14, the oldest 22) the little tease brought back tothe home we all now shared was turned into a different kind offeminized sex-toy, all designed to please the Mistresses andtheir dominant friends.The little...

3 years ago
  • 0
  • 17
  • 0

Making of My Sissy Part 3

One day I was home to see, first hand, how my sissy's day progressed. The day went as I thought it would, well planned and a perfect schedule to keep my little one busy. Then there was a knock at the door. My sissy never went near the door. I watched as the bell rang. Again my sissy never even looked at the door. I asked him if there was something wrong. He said that he doesn't answer the door when dressed as such. I asked "dressed as what?" "This is what you liked and you agreed that you would...

2 years ago
  • 0
  • 12
  • 0

Americas Next top Sissy part 5

Part 5 So Part 5 of my homage to 'America's Next Top Model' forced fem style lol ... hope you enjoy it and please comment. After a humiliating photo shoot the sissies wake up to another elimination. Jim felt better after a night's sleep, only to face wearing the overly feminine pink sissy dress he and the other sissies are forced to wear for the elimination. 'Getting eliminated, maybe that's the way out? At the very least I would get the satisfaction of denying these sick...

2 years ago
  • 0
  • 15
  • 0

A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

3 years ago
  • 0
  • 22
  • 0

A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
  • 0
  • 11
  • 0

I Want To Be A Sissy Part 1

Oh, my goodness! Today is going to be an exciting day. Mistress and I will find out if I can finally fill the C-cup brassiere she desires that I wear. I am so excited! A C-cup means so much to me. I adore my B's, the darling little girls, but a Sissy can be so much more of a Sissy when her cup size says WOMAN! As soon as I finish my morning toilette, Mistress will hook me into the cutest white underwire C-cup bra I have even seen and the moment will be here. I will fill the cups or...

3 years ago
  • 0
  • 25
  • 0

Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

1 year ago
  • 0
  • 16
  • 0

Andrew The Unsuspecting Sissy Part IV

ANDREW THE UNSUSPECTING SISSY PART IV [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUS FAR..... ANDREW NOW DREW: SISSY SUPERSTAR, SOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIALIST, WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR ALICIA NEWMAN: MEDICAL DIRECTOR OF THE...

4 years ago
  • 0
  • 12
  • 0

My sisters their friends and me their sissy Part 2

Part Four Jolt after jolt of electricity passed through my body. Each longer and worse than the one before it. I held my number two hole shut because I believed what Joy had said about losing any of the water. But the pain was becoming almost too much. I knew that in another jolt or two my control would be completely gone and even with the help of the big thing back there plugging me I was certain to lose that water. And there were two gallons in me making me look really pregnant....

2 years ago
  • 0
  • 25
  • 0

Mommys Dirty Sissy Slut part 1

Mommy's Dirty Sissy Slut part 1 by dirteesissy "Answer the door for me, Brother Dearest and make sure to greet my guests Properly!" I headed to the front door, shame filling my heart, as I tottered on 5" stiletto heels. Not the usual footwear for a 20 year old man, but I couldn't have looked less like a male dressed as I was. Chapter 1. Last week my sister, Alicia, caught me masturbating to stories on a website called Fictionmania. In most cases this would have been...

1 year ago
  • 0
  • 11
  • 0

Trucker Daddy gets himself a New Sissy part 1 and 2

TRUCKER DADDY GETS HIMSELF A SISSY BY DEEWET It could easily be the lowest point in Denny's life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truck Stop. He almost jumped out of his skin when someone knocked on the window. Denny...

4 years ago
  • 0
  • 12
  • 0

Andrew The Unsuspecting Sissy Part V

ANDREW THE UNSUSPECTING SISSY PART V [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUS FAR..... ANDREW NOW DREW: SISSY SUPERSTAR, SOON TO BE HUSBAND TO JIM JIM BRECKMAN: BILLIONAIRE INDUSTRIALIST, WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR ALICIA NEWMAN: MEDICAL DIRECTOR OF THE...

2 years ago
  • 0
  • 19
  • 0

Andrew The Unsuspecting Sissy Part III

ANDREW THE UNSUSPECTING SISSY PART III [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUSFAR..... ANDREW NOW DREW: SISSY SUPERSTARSOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIAL WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR NEWMAN: MEDICAL DIRECTOR OF THE MANOR PENELOPE...

2 years ago
  • 0
  • 16
  • 0

Blackmailed Sissy Whore Part one

Blackmailed Sissy Whore Part 1 It's amazing how quickly life can spiral out of control. One moment your enjoying what you think is just a little harmless indulgence in your submissive crossdressing fantasy life when, out of nowhere, your life is turned upside down. It was a Saturday morning in February, 2020. I was a single guy, living the dream. I had a really good job and was living in a 2 bedroom apartment in an upscale complex a few miles South of Pittsburgh. I had transformed...

3 years ago
  • 0
  • 13
  • 0

Maid to Measure or Sissy Slave by Design Part Two

Maid to Measure, or Sissy Slave by Design, Part Two By Mistress Kathrine The room was very bright. It hurt to open his eyes so he tried to cover them with his hand but found he couldn't move it. He started going over carefully the last things he could remember. He was in a beautiful home, Kathrine? No Mistress? Oh if only he could wake up and remember what happened? As his mind began to clear he could start to see more clearly. It looked like he was in a...

1 year ago
  • 0
  • 16
  • 0

Becoming a Sissy Part 10

Apologies for the delay. This is the final part of "becoming a sissy". Obviously, I have packed a lot more into this story, and I apologise if it got complicated with too many characters. I'm thinking of writing another story which will take up from where we are now, but I will make it more focused on one or two characters. It's my first story, so I guess lessons.Over the next five days a plan formulated in Tom's mind. As he thought about it he would have three submissive sluts vying for his...

2 years ago
  • 0
  • 19
  • 0

Andrew The Unsuspecting Sissy Part VII

ANDREW THE UNSUSPECTING SISSY PART VII [email protected] *** A NOTE TO ANDREWS' FANS: I DON'T GET VERY MUCH FEEDBACK, PERHAPS 4 OR 5 PEOPLE WITH EACH CHAPTER. WHILE I APPRECIATE THE SUPPORT FROM THOSE THAT ENJOY THE STORY, I CAN'T SEE CONTINUING THE TALE IF SEEMINGLY VERY FEW PEOPLE ARE INTERESTED. SO, IF YOU ENJOY THE STORY, OR DON'T, PLEASE LET ME KNOW! MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN...

3 years ago
  • 0
  • 14
  • 0

Maid to Measure or Sissy Slave by Deesign Part 3

With Kind Proofing by Vickie Tern Maid to Measure, or Sissy Slave by Design, Part 3 By Mistress Kathrine The morning after Kathrine let Nikki sleep in the Master bedroom with her, she lay thinking about the things she still needed to train her pretty Sissy. Sissy Nikki didn't know anything about Kathrine's plans to marry her, and have a child with her, not yet. She decided it was time to wake her Sissy and get at least the wedding...

1 year ago
  • 0
  • 11
  • 0

A sissy called Jezebel Part XX

A sissy called Jezebel Part XX - Jezebel and hir entire family next attend a family wedding, where the bride is a sissy (of course.) What sexy, submissive traditions prepare the beautiful blushing bride for hir big day? Will our bride vow to love, cherish and (especially) obey, all orders, whims, without any hesitation, from hir goddess/wife/mistress and to her complete and utter satisfaction? There is non-stop teasing in the car about the bridesmaid dress. Everyone knows I adore...

1 year ago
  • 0
  • 11
  • 0

My Sissy Life Part 17

My Sissy Life Part 17 I fixed my make up and went back to cleaning, I didn't want to get into trouble because my chores weren't done. I don't know how I would explain that, 'I'm sorry mother I couldn't finish dusting because I was too busy sucking Jake's cock.'. That is not a conversation I wanted to have. I wasn't sure what was going to happen when Jake babysat me for the weekend. I had an idea that there would be a repeat of what just happened. The rest of the night. I served...

3 years ago
  • 0
  • 19
  • 0

Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
  • 0
  • 20
  • 0

Mein erstes Mal als Sissy Part 10

Fortsetzung von:https://de.xhamster.com/stories/mein-erstes-mal-als-sissy-part-9-708712„Hallo meine kleine Schlampe“, begrüßt er mich nachdem er mich ein Zeit lang mehr oder weniger ignorierte. „Nun kommen wir zu meinem persönlichen Höhepunkt des Wochenendes“, er führt mich nochmal ins Bad und legt mir Dessous in Rot bereit, dazu ein rotes Negligees, die blonde Perücke lasse ich auf und er bittet mich, dass ich mich ganz nuttig für ihn zu Recht mache. Ich freue mich darauf endlich wieder von...

1 year ago
  • 0
  • 34
  • 0

Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
3 years ago
  • 0
  • 9
  • 0

Rubber Sissy Panties Part 2

Rubber Sissy Panties Part II Clark woke up at work. He was dressed in the same clothes as in the previous day, shaven and the clothes were clean and ironed to perfection. He looked at the clock on his computer, and it was 7am, way earlier than anyone else would be hanging around. He raised himself off his chair and walked to the W/C, ready to relieve his full bladder. Not noticing his own behavior, he lowers his pants and sits down on the toilet, and points his sissy clitty...

4 years ago
  • 0
  • 16
  • 0

Blackmailed Sissy Whore Part Three

Blackmailed Sissy Whore Part 3 I did manage to get a little sleep. After Tiffany finally zonked out, and the continual grinding on my thigh and the relentless playing with my nipple rings stopped, I couldn't keep my eyes open any longer. Friday night was the last full night's sleep I had gotten since Marcus took over my computer, and my life. I woke up before my alarm went off, which was a good thing. I was tangled up in limbs so securely, it took me several minutes to snake my way...

2 years ago
  • 0
  • 10
  • 0

Lockdown Sissy part 1

Author's Note: Thanks to those who have reached out to me with story ideas. It's been difficult to get any writing done these past few months, but hopefully my head is finally back in writing mode. I hope you enjoy this nasty little fantasy. Please let me know if you have any thoughts or ideas--either here in the comments or directly at [email protected] xoxox Emshoninque Lockdown Sissy- part 1 I made a resolution to become a better sissy in 2020. It's something that has...

2 years ago
  • 0
  • 14
  • 0

Becoming a Sissy Maid for Mark and Rebecca Part Three Ms Rebecca Shares Her Sexual Research of Sissies

Becoming a Sissy Maid for Mark & Rebecca, Part Three - Ms. Rebecca Begins Sharing Her Sexual Research NOTE to Review Writers: Thank you so much for the incredibly positive feedback. It is definitely motivating me to write more and write faster. Now to part three of our story. "Tell me what you know about males who are feminized so completely they are transformed into a sissy, changed from the less than manly person she had been before coming under the control of a strict...

1 year ago
  • 0
  • 15
  • 0

I Want To Be A Sissy Part 4

After my intense and strangely satisfying lipstick application initiation, all the women and young girls and the male pharmacist drifted off, allowing Judy to take control of her cute little pansy customer once again. I was dumbfounded that the woman I first saw coming towards me with what I thought was disgust in her eyes, was really a rougher, blunted extension of my darling wife, my Mistress Claire. Judy seemed perfectly happy to take command of me and my sissy needs. She proved...

3 years ago
  • 0
  • 15
  • 0

Andrew The Unsuspecting Sissy Part II

ANDREW THE UNSPUSPECTING SISSY PART II ANDREW'S SISSY EDUCATION BEGINS............ [email protected] Mother and daughter chatted while they ate their breakfast. Several sissies flitted about changing flowers and removing dirty dishes. "Mother," said Sarah. "How many sissies call the Manor their home these days?" "Hmmm," said Audrey as she placed her coffee cup in its saucer. I'd have to say with the school, the modeling agency, the internet dormitory, the domestic...

3 years ago
  • 0
  • 13
  • 0

Sissy Prudence Part 2

Sissy Prudence (Part 2) (by Sissy Caroline 22 December 2006) Section 1 "Prudence. Come here at once." Dressed in his maid's uniform, Prudence walked obediently into the room and then knelt down before his mother, his eyes lowered to her feet. He knew he was in trouble because she had called him Prudence. "I have just been talking to Mrs. Smithton, who tells me that she is increasingly concerned about the quality of your work when you are supposed to be performing maid duties...

2 years ago
  • 0
  • 13
  • 0

My Sissy Life Part 3

My Sissy Life Part 3 When I got to my room I saw the Hello Kitty dry erase board on my door. There was a note from my brother that said 'Sissy, I need my jock strap clean by Friday morning.' Oh good, I get to hand wash my brothers jock strap again. Is it Christmas already? Almost every day there is a note on the board from someone telling me that they want me to do something. I walked in my room. I still can't believe how ultra girlie my...

1 year ago
  • 0
  • 18
  • 0

Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

1 year ago
  • 0
  • 11
  • 0

The Slave and the Sissy part Four

Pepper and I knelt on the silky sheets of the bed and studied each-other in disbelief; our cocks rigid and ready for relief. I took her sweet sissy cock in hand as I sniffed and licked at her face and neck; her skin as white and silky as the sheets. She thrust her slippery little sissy cock back and forth between my fingers as I teased her glistening little pink bell-end. Pepper panted with anticipation as she unhitched her crop top; her sweet little breasts stood firm and inviting, my cock...

2 years ago
  • 0
  • 19
  • 0

Mommys Dirty Sissy Slut part 2

Mommy's Dirty Sissy Slut part 2 by dirteesissy Please read part 1 before enjoying this instalment. Chapter 5. After I had finished cleaning Lisa's toilet with my tongue, she had me brush my teeth, as she finished her bath. I dried her with a fluffy white towel before helping her dress. Kneeling in front of her as she stepped into a pair of darling lacy pink thong panties, she bade me to pull them up. I obeyed and was overjoyed to serve her in such an intimate way. A pink...

3 years ago
  • 0
  • 24
  • 0

Becoming A Sissy Slut part 2

I awoke Sunday morning alone in Kassy’s bed, still in the tight mini skirt, my ass was deliciously sore bringing back a flood of memories from last night. I had spent the evening in full drag dressed as a slut and serving my mistress’s rubber cock followed by swallowing my own cum. It was hands down the best night of my life, I had never came so hard, and the rush I felt while serving her was a high that I’d never known. I rolled out of bed and stood up, my wig had fallen off in the night...

4 years ago
  • 0
  • 14
  • 0

A sissy called Jezebel Part VII

A sissy called Jezebel Part VII - Jezebel has finished hir tour with the Head Mistress into the secretive dungeon/reform school below the fair walls of the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. But is the Head Mistress entirely done with Jezebel? Additionally, what ever does one learn in a 'sissy life skills' class? I require the gurls in my harem to crawl on the floor at home and in private at the office. So get on...

3 years ago
  • 0
  • 12
  • 0

Sissy Prudence Part 3

Sissy Prudence (Part 3) (by Sissy Caroline) Section 1 "That's our Sissy Prudence in the garden. Isn't he a delight?" Bridget looked out the window and, despite the fact that boys were not really her interest, she found the sight presented to her was quite exciting. She had never thought that a boy in a dress could be such an erotic fantasy. Prue was working in the garden, which was something he now really enjoyed as a break from his duties inside the house. Not that he was...

3 years ago
  • 0
  • 16
  • 0

Americas Next Top Sissy part 3

After waking up, Jim finds himself in a feminine bedroom with the 11 other naked men. When the Nurse from the previous night enters the room dressed in a leather cat suit and introduces herself as Ms J, she wakes the men wake up and they soon learn to behaviour or implants in their bodies will make them. Now forced to wear ultra feminine clothes and wait holding each others hand for the looming elimination! Part 3 Jim is standing in the middle of the bedroom waiting for Ms J...

2 years ago
  • 0
  • 10
  • 0

A sissy called Jezebel Part VI

A sissy called Jezebel Part VI - Jezebel's inspection has been completed at the Head Mistress's office of the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. Jezebel is taken by the Head Mistress into the secretive dungeon/reform school below the fair walls of Templeton. All sorts of secrets and surprises are revealed. Headmistress Saxon looks at me. "What class did you just miss?" "Deportment, Headmistress." Forty five minutes...

1 year ago
  • 0
  • 18
  • 0

Sharons Mistress Throws a Sissy Party

Sharon’s Mistress throws a Sissy Party(Prior chapter is Sharon’s Sissy Saturday)The next morning Mistress was kind enough to let me sleep in, but an alarm above the door to my little cell went off at 6:30, rousing me from a delicious dream of being naked and fucked in the woods by a handsome, dark-haired man who kept me as his personal sissy slave slut. I woke with the sensation of his hard cock filling my dripping pussy, and I realized I was still leaking cum from my day in the booth. I...

2 years ago
  • 0
  • 25
  • 0

Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

3 years ago
  • 0
  • 23
  • 0

Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

2 years ago
  • 0
  • 22
  • 0

Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
  • 0
  • 11
  • 0

Cometh the Sissy Part 1

Cometh the Sissy (Part 1) Stevie "No. No fucking way." "Ahh, c'mon honey. It'll be so much fun! It's about me not you. I just need you there as, well, sort of a training aid. I promise you that you'll love it." "It's gross, seriously, some fat old man, what the fuck are you thinking about?" "It's about power. Control. Desire. I want to see if I can do it. You'll out all day and I'm doing my online classes and shit, there's only so many dildos and vibrators. I want to...

2 years ago
  • 0
  • 17
  • 0

My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

2 years ago
  • 0
  • 25
  • 0

Americas Next Top Sissy Part 2

Waking on a TV set, Jim finds himself volunteered to be a contestant on a strange show... 'America's Next Top Sissy'. Having been pierced and photographed Jim is left in a dimly lit room with 11 other men all humiliated in the same way. Part 2 Waking with a start, Jim sat up and instinctively covered his naked body as best he could with his hands. After a few seconds Jim realised that he was no longer bound to the gurney but in a bed. With the memories of yesterday fresh in his...

3 years ago
  • 0
  • 10
  • 0

Becoming a Sissy Part 3

Third instalment. Apologies it has been slow until now, but things progress a lot. In part three. We start with Tom, getting some of his background and thoughts on Peter and then back to Peter's voice.Tom's story.Myself and Peter had been friends since we were in school together were we had an interest in supporting common which really kept us as friends for years and years. We finished school, went to college got our first jobs and settled down all the time being in touch with each other,...

3 years ago
  • 0
  • 31
  • 0

Sissy dannis birthday party

My last "true life" story was about how I became Heidi's sissy crossdresser "Danni" - I only explained the initial experience of Heidi coming home to find me in one of her dresses - followed by spankings, punishment and eventually getting pegged by her wearing a strapon. Of course there is MUCH more to what happened next (like being taken out in public and going shopping, to hair salons, etc...), but I'd like to for now jump ahead to what happened to me on my 19th birthday. By then I...

3 years ago
  • 0
  • 21
  • 0

My girlfriend made me a sissy part 2

For those who are reading my story for the first time make sure that you go through part 1I woke up, stretched out and smiled as I felt the familiar sensation of mygirlfriend's panties rubbing on my cock. The feeling instantly brought backmemories of the night before: I had gone to a party with my rather dominantgirlfriend; been coerced into her panties; sucked my very first cock andfound out my girlfriend had fucked another guy whilst I was doing it. Iloved every minute of it, my sissy-cock...

4 years ago
  • 0
  • 16
  • 0

My girlfriend made me a sissy part 2

Before reading this make sure you have gone through part 1I woke up, stretched out and smiled as I felt the familiar sensation of mygirlfriend's panties rubbing on my cock. The feeling instantly brought backmemories of the night before: I had gone to a party with my rather dominantgirlfriend; been coerced into her panties; sucked my very first cock andfound out my girlfriend had fucked another guy whilst I was doing it. Iloved every minute of it, my sissy-cock was rising as I remembered it...

3 years ago
  • 0
  • 11
  • 0

A sissy called Jezebel Part XVIII

A sissy called Jezebel Part XVIII - Ever wonder what the womyns football team locker room is like before the 'Big Game' at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission? Let's find out, together. "Well, looks like you don't actually need the school uniform, it's time for you to get our football team ready for the big game, and then you need to practice with the band, my little majorette." "Yes Headmistress." "How do you...

2 years ago
  • 0
  • 11
  • 0

A sissy called Jezebel Part XIV

A sissy called Jezebel Part XIV - The Headmistress of Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission, reveals even more mind blowing secrets of hir own family history to Jezebel. With that we enter the medical office. Headmistress Saxon says, "The Doctor will be here in a few minutes. So just to fill you in, many of our students were confused about what really happened. The womyn students of both the McCarthur clan and the...

2 years ago
  • 0
  • 11
  • 0

A sissy called Jezebel Part XLII

A sissy called Jezebel Part XLII - A sissy's bitch or what a gurl has to do to get a freaking cuddle around here. (Forgive my little homage to Rocky & Bullwinkle, 'Find out next time......') "Uhm, how did you get into my diary?" I queried Irmagard. "Your sister Abigail generously told me how to pick the lock," she responds very matter of factly. I've operated under the assumption that my sweet sisters were getting into my diary, I just stopped caring that they could read...

Porn Trends