Decade Of Sissy Part Three free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
So, our sex life was still terrific but in a new way. My girl would lay out my panties for the day I will go to work and come home we will then have fantastic sex every evening. Sometimes she would give me blowjobs however most of the times sex would be with A large dildo for both of us. When I would eat her out and pleaser with my tongue I could tell her little pussy was well used and spread large I could put my whole hand in it now with ease. our sexual positions were amazing she always like to take me from behind however she realized if you took my missionary I would cum like a girl. She would pull my little panties to the side exposing my man pussy leaving my hard clit inside my panties she would then pushing to me putting my ankles around her neck and ride me until I would cum in my panties, She would then scoop it up with her hand and feed it to me. On my birthday she told me her present would be her pussy and I can have her anyway that I wanted I was so excited I told her I wanted it the way we used to with her swallowing my come after I put it to her. So for my birthday she took off my panties for the first time in sometime exposing my little clit, And suck me hard I told her I didn't want to come in her mouth but in her pussy. She agreed I told her I wanted to take her missionary so she laid down and I put my penis in there however I could barely feel anything and I couldn't stay hard. She giggled at me and told me it was cause I was gay now and only like dick in my butt in that pussy want to do it for me anymore. She said since you can't stay hard let's go shopping and I'll buy you something for your birthday, so I got dressed I said what are you gonna buy me she told me I'd be surprised and happy. We then drove across town to a lingerie store. We went in there was a sales clerk there she was cute and that her 20s, we saw her looking at various teddies stockings and other sexy outfits. The clerk came over and asked if she could help us. My girl smiled at her and ask if there was a changing room or we could try on an outfit. The clerk said yes as long as you leave your panties on your welcome to try on anything. My girl looked at her and said oh it's not for me to try on it's for him. The clerk turned very red and said I see he can also try on things. My girls and smiled and said don't worry he'll leave on his panties. The girl continue to smile and look at us my girl picked out a few cute Teddy's and some nighties n baby doll outfits and sent me back to the back room. It was a small room that was open with me here's my girl stood there the interest watching me take off my clothes she put her hand on her pants and start playing with her pussy the clerk noticed this but didn't say anything. I put on a few. NightiesI thought they were very nice I put on a baby doll outfit it was short and only covered half of my but my girl grimaced and she came. She then looked over at the store clerk and said would you like to see. The clerk giggled and said sure why not at that point my girl parade around the store including the storefront and the various outfits. The clerk checked me out and looked at my girl she noticed how small my penis was even though it was obvious I was hard my girl then it started to show her how small my penis really was she laughed and turn red or we bought a few outfits that day and the clerk apologize for my small penis to my girl. We got home my girl said it's still your birthday do you still want to see if you can get off and my pussy I was very excited and figured it would not take much I told her I wanted to take her doggy style. So she bent over her great ass in the air I rubbed it and massage it I then put my penis and her loose pussy I was fucking her as hard as I could and she began to giggle saying how much a tickled. I felt very humiliated and went soft again my girl apologized but said she couldn't help it it just tickle too much . She asked me what I could do to make up for laughing at me on my birthday I ask her if I could put it in her but she agreed to then bend over the bed and I slipped into her tiny butt hole and was able to get offshe then reminded me how gay I was that I can only get off with a butt hole.

Same as Decade of sissy part three Videos

2 years ago
  • 0
  • 20
  • 0

DECADE OF SISSY PART 2

So, with all my boxers and briefs gone and replaced by various thongs I was feeling odd but went with it anyway by girl liked it. So i put on a cute pair of thongs and got ready for work. When I got there i was nervous but excited that i was in sexy panties, When i got home my girl was there. she answered the door wearing a lacie and nothing else. she had me strip on the porch down to my panties i got red in the face but it was fun so i did it, we then went in and had a long fuck section. she...

3 years ago
  • 0
  • 50
  • 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
  • 23
  • 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...

4 years ago
  • 0
  • 54
  • 0

Sissys SheCock Training Part Three

Laying next to Mistress caressing and kissing her plump moist wet red lips, slowly stroking my long nails up her stocking clad legs. she trembled as was Thinking what a day it had been so far beyond my wildest dreams, my she-cock rubbing on her sticky thighs as we kissed was making me all hard and horny again, pulling away slightly from our wet kiss breathlessly Mistress whispered lets make sissy aour little cock slut.MMmmmm i whispered back that sounds delicious, cock traing the final lesson....

2 years ago
  • 0
  • 29
  • 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
  • 25
  • 0

Cyber Sissy Part Three

Cyber to Real Time Sissy Part 3 By Miss Vicky "Good, you may begin by repaying my hospitality. I want you to clear the table and rinse the china. You may then put everything in the dishwasher. When you are finished, I will continue your training."I obeyed at once, being very careful with the china. I wondered where Megan was while I was doing my domestic chores. The answer to that came a minute later. I was startled by first a flash then the unmistakable sound of a Polaroid camera...

2 years ago
  • 0
  • 14
  • 0

DECADE OF SISSY

So, I started seeing this girl in my 20s and she was hot and wild in the bed. She was hot tall nice ass great breast stunning in the face, and did i mention a freak in the bed. I noticed early on that she was very dominate in the bed, she was always in charge of the positions and how often. But that didn't matter it was nearly daily. She kept her pussy shaved and had her clit pierced she only wore sexy panties and bras no granny panties or boring bras colors bright pinks and purples were all...

2 years ago
  • 0
  • 20
  • 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
  • 26
  • 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
  • 35
  • 0

Sissy Teaches Me Part Three

Sissy opened her legs a little more as I leaned up to get a better feel of her perfect divide. As I did, I felt the dampness of the towel under my naked ass. It was soaked. I really did cum. A lot.I actually looked down between my legs to see the wetness there between them. The towel was a lavender color, so when I looked, the darker color of the purple showed where my sexual liquid had poured out of me. It was no little spot. It was huge. I had no idea I could cum like that. I had no idea that...

Incest
4 years ago
  • 0
  • 17
  • 0

Making of My Sissy Part Three

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...

4 years ago
  • 0
  • 34
  • 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
  • 20
  • 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...

4 years ago
  • 0
  • 50
  • 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...

2 years ago
  • 0
  • 25
  • 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
  • 19
  • 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
  • 39
  • 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
  • 21
  • 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
  • 20
  • 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
  • 32
  • 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
  • 26
  • 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...

4 years ago
  • 0
  • 21
  • 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
  • 28
  • 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
  • 29
  • 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
  • 22
  • 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
  • 19
  • 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
  • 19
  • 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...

4 years ago
  • 0
  • 35
  • 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...

3 years ago
  • 0
  • 32
  • 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...

2 years ago
  • 0
  • 54
  • 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
  • 21
  • 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...

2 years ago
  • 0
  • 19
  • 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...

3 years ago
  • 0
  • 27
  • 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...

2 years ago
  • 0
  • 22
  • 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
  • 23
  • 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
  • 21
  • 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...

3 years ago
  • 0
  • 18
  • 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
  • 27
  • 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....

2 years ago
  • 0
  • 24
  • 0

Sissy Farm Chapter Three

Sissy Farm - Chapter Three - By: Beverly Taff List of Characters: Me: Michael, (Soon to be Michelle) A natural sissy; Aunty Beverly: My mother's sister. (Who adopted me aged 10.); Janice: My Younger Sister. Chapter Three By the time I had dried my nails and remedied my 'condition' I returned to find Janice sitting on Aunty Bev's bed while Aunty Bev was combing her hair. Janice was obviously enjoying the attention and I could not help but look enviously as the comb...

3 years ago
  • 0
  • 37
  • 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...

4 years ago
  • 0
  • 45
  • 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
  • 20
  • 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
  • 22
  • 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
  • 30
  • 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
  • 19
  • 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...

2 years ago
  • 0
  • 38
  • 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...

3 years ago
  • 0
  • 39
  • 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
  • 34
  • 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...

3 years ago
  • 0
  • 36
  • 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
  • 22
  • 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
  • 27
  • 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
  • 41
  • 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...

4 years ago
  • 0
  • 20
  • 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,...

4 years ago
  • 0
  • 56
  • 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
  • 32
  • 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
  • 26
  • 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
  • 19
  • 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...

3 years ago
  • 0
  • 18
  • 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...

Porn Trends