My Sissy Fantasy free porn video

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My wife has been dating around for years. She loves the feel of different cocks and I enjoy watching her with other men.
Recently, she decided it would be fun to put me in a chastity. She said it was only temporary and if I didn't like it, she'd take it off. After a couple of days, I decided, I'd had enough. She didn't. She said she liked having me locked up and know I couldn't get hard or jerk off. "I'll let you know when you can cum again." She wore the key around he neck like a trophy. Her boyfriends would come over and she would have sex with them in front of me, only I wasn't able to jerk off. After about 4 weeks, I was going crazy and she knew it. Little did I know this was all part of her plan.

One night as she was getting ready for a date, she asked me if I was ready to have the chastity taken off? I was so excited, I instantly got hard. Or course, there were a few things I had to do first. After she shaved her legs, she handed her razor to me and said, "You're turn?" I hesitated at first, but she said, "You want that thing off your little cock don't you?" No argument there. I took the razor and began shaving my legs. When I was finished, she said, "Don't stop there. I want everything shaved. You can leave a little girl patch above your cock, but that's it" My cock was busting out to the chastity. I did as I was told and eventually, I was silky smooth all over.

"Don't you look better! Now go get dressed." I went and put on some jeans and a shirt and came back. She said, not in that. I laid out some nice clothes for you on the bed. I walked in and saw a short, silky black skirt, thigh high stockings, and lacy see-through blouse with a bright pink bra. Again, I nervously laughed. She did not laugh back. "If you ever want to cum again, you'll put those on." I thought to myself, whatever, it's not like anyone will see me. So I went ahead and got dressed. The stocking felt so good going over my smooth legs. Again, my cock pressed against my chastity cage. The bra was tight and uncomfortable. When I put the blouse on, you could still see the pink bra underneath. The skirt felt light and flimsy as if a good breeze could easily blow it up. When I was finally dressed she made me look in the mirror. I actually look pretty good. Next thing I know, there's a knock on the door. Terrified, I start to take off the clothes. She tells me to stop and go answer the door. I refuse, then she looks down at my cock locked up. "You're choice."

As I walk towards the door I could feel the cool air between my legs under my skirt. I look outside and see it's one of her boyfriend's. No way I'm opening the door. Unfortunately, I didn't realize she was right behind me. She quickly opens the door and I just stand there frozen.
Her boyfriend begins to laugh. "So you really did it?!" He begins to look me up and down. "Not too bad. So where are we taking him?

My first thought was, I'm not going anywhere, but back to the bedroom and change. My wife suggested an area known for its gay bars. I immediately said no. I have to draw the line somewhere. She said if I didn't get into the car, they were going without me and that I'd never see the key to my cage again. Reluctantly, I got into the backseat of his car. As we drove she talked about how much fun we were going to have and that deep down she knew this is what I wanted.

We pulled up to the parking lot beside the bar. It was dark outside and I was thankful. She told me to get out of the car. I refused. Next thing I know she rolls down the window, takes the key off her necklace and throws it across the parking lot. "Whatever, it's up to you." They both got out of the car and started heading to the bar. The parking lot was empty, so I got out of the car and quickly started looking for the key. I could feel the cool air underneath my skit as I frantically searched in the dark. As I was bending down, I suddenly heard a voice. "Did you lose something?" I turned around and saw two guys standing there. "Ummmm, no. I'm okay." I tried to pull my skirt down over my ass, but it was too short. I'm sure they got a look. Just then, I finally found it! I picked it up, thanked them for offering to help and hurried back to the car. It was locked. Just then, my wife came walking out of the bar.

She must have been watching the car from inside. She said I might as well come inside and have a drink. She did offer to put my cock cage in her purse if I wanted to take it off. FInally! I unlocked it and handed it to her. It felt so good to finally be free after so many weeks. I followed closely behind her, thinking maybe no one would really notice. It seemed to pretty much work. No one pointed or laughed or anything. I got a couple of looks, but they were more like friendly smiles. We walked over to the bar where her boyfriend stood with several shots. "Bottoms up!" By this time I was ready for a drink and slammed it down. He quickly ordered another round. It was about this time that I noticed the nice guys from the parking lot were sitting at a table close to us. One of them raised his glass to salute us. My wife smiled back and asked if they were friends of mine? I said sort of, that I met them in the parking lot.

As they looked at us, my wife began to rub the top of my thigh. I suddenly realized why wearing a really short skirt was not a good thing. My cock pop up like a jack-in-the-box. I quickly grabbed the front of my skirt and tried to hold it down. My cock was pressing so hard against it that I needed both hands to keep it at bay. I quickly turned towards the bar so no one could see what was happening. That's when my wife's boyfriend said, "You might as well tell him." What, I asked? My wife had an evil grin on her face. Well, she said, I put a little blue pill in your drink. "What!?!" Then she said, "I don't think your little sissy cock is going to go soft anytime soon." Just when I thought things couldn't get any worse, I felt a tap on my shoulder.

I turned around to see the guy from the parking lot standing next to me. "Hi, I'm Steve." He held out his hand and I just stood there in shock. My wife quickly scolded me. "Don't be rude! Shake is hand." I removed my hand from my skirt to shake is hand and my hard cock popped up. He smiled and stared, but was nice enough not to say anything. "How about if I buy you guys a round?" As we chatted, he was nice enough to move close enough to block my raging hard on from the whole bar. The outline of my head was pressing against my skirt and a small stain of precum was beginning to soak through. I felt so humiliated.

Our drinks came and he made a toast. By this time I was really starting to feel buzzed. I raised my glass and my skirt was practically lifted all the way up for everyone to see. Next thing I know, my wife spills her frozen red drink all over me. She just smiled and said, "Oops!" as it dripped down. My new friend took pity on me and offered to walk in front of me to the bathroom, so no one would see my still hard cock. I followed closely behind him as we crossed the bar and went into the bathroom. Luckily, no one was there. I grabbed some paper towels, when all of the sudden, I felt his hands on my hips and the warmth of his hard cock pressing against my ass. I turned and asked what he was doing?

He told me it was okay and not to fight it. He pulled me into one of the bathroom stalls and began reaching under my skirt. My cock was still hard as a rock and I was unable to get it to go down. I told him that this was just a game my wife was making me play and that I really wasn't into guys. As he grabbed my cock he said, "Really? It sure doesn't feel that way." He then told me to get down on my knees and take his cock out. I felt the tight squeeze from his hand reach around my balls. I winced in pain as my knees immediately buckled and I crumbled to the floor. "That's better", he said.

He squeezed harder and said take it out. I quickly unzipped his pants and pulled out his half hard cock. It sprung out of his pants and waved in front of my face. It was thick and at least eight inches. I could see the precum already leaking out of his mushroom head. He told me to open my mouth. I hesitated and again he squeezed my balls, this time much tighter than before. I let out a cry, which I think could probably be heard from the bar. With my mouth still open I felt the warmth of his smooth cock slid in. Finally, I had tasted another man's cock. He grabbed the back of my head and began sliding it in and out. It felt so different in my mouth. I felt my body get warmer as I couldn't help but enjoy this new sensation. Every once in awhile he would take it out and slap it against my face. Then slide it back in. My head began to move up and down his cock on its own. "That's more like it."

Suddenly, I heard the bathroom door open. I started to get up, but he held me down. There was a knock on the stall door. "Oh, Shit", I thought. Then I heard his friend's voice asking if everything was okay. He swung open he door to find me on my knees with his friend's cock in my mouth. Needless to say, he didn't wait for an invitation. He quickly unzipped his pants and pulled out his cock. It was a nice size too with a slight curve to the left. I opened my mouth eagerly as both their cocks slid in. It was like both of their cocks were fighting to get to the back of my throat.

The first guy quickly pulled out and I thought he was going to cum. Next thing I know, he lifts me up and starts to rub his cock against my ass. I begin to pull away, but he's already got both my wrists behind my back. I'm bent over and off balance as he friend continues to fuck my mouth. I feel his warm head pressing against hole. It's wet from me sucking it as it penetrates me for the first time. I moan in pain and ecstasy. He tells me to just relax. I try, but I'm unable. He pushes it in deeper as my cries are muffled by his friend's cock in my mouth. My eyes widen as he tells me, "Half way there." I don't think I can take anymore. He begins sliding it in and out. I look down to see precum running out of my hard cock landing on the floor. His pace begins to pick up and I feel him inching deeper and deeper. I try to pull away to ease the pain, but he grabs my hips and pulls me closer. I can tell he's getting close. In a way, it will be a relief to feel his hot cum explode inside me. He tenses up and plows another inch or two deeper, holding tight to my hips. He must have hit something inside me, because suddenly, my cock began to squirt cum everywhere. It had been so long since I'd cum. I felt the warms of his cum fill my ass while my own cum ran down my legs.

I was so focused on everything else, I almost forgot about his friend's cock in my mouth. Wanting to get out of there I began sucking it harder. I was soon rewarded with the warm feeling of his cum hitting the back of my throat. I pulled back which was a mistake as he began to shoot cum all over my face. It was at this time that I caught something out of the corner of my eye. Someone was watching above the stall. With a cock in my ass and cum running down my face, I turned and looked up to see my wife's boyfriend with camera phone. He had recorded the whole thing. He disappeared behind the stall as I quickly tried to get myself together.

I opened the stall door to go after him and saw three guys standing there. They must have been watching from the door crack. I tried to squeeze by them, but they grabbed me. "Not so fast sweetheart." They pushed me back into the stall. Their cocks were already out and hard as they started groping me. One of them pushed down on my shoulders. My legs we still shaky and I quickly went down on my knees. I could feel the cum dripping out of my ass. They began taking turns fucking my mouth. All I could think about was how my wife's boyfriend was showing her the video. One by one, each of the guy's came. The first one came in my mouth. The second, on my face. And the third came all over my body. The smell of cum was everywhere and I could feel it starting to dry on my skin. As they opened the door, I saw two more guys waiting. This was going to go on all night!

I decided my only choice was to make a run for the door. Which meant heading back into the bar without cleaning up. I pushed my way past the guys who seem quite disappointed. I could feel the cum dripping down me. It was everywhere. I kept my eyes down, as I walked through the bar. I knew people were looking at me, but I didn't want to make eye contact. I finally reached my wife and her boyfriend. She just busted out laughing. "What took you so long? Oh, yeah, I guess this." She was showing the video of me in the stall to a group of guys. I begged her to take me home. "But I haven't finished my drink." I pleaded with her again. "Okay, but you have to do one more thing." She handed the camera phone to the two guys who had taken me the bathroom. "I want a picture of us to remember this monumental evening. Now that I know what a sissy you are, this will be the first of many." At that moment he snapped the picture capturing my dazed look as I realized what my life would be like from now on.

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Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

3 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - By: Beverly 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...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

2 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly 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; Dr Shirley: 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 Bev's...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

1 year ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

1 year ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - By: Beverly 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 Dr Shirley: 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 Bev's brother.) James: AKA. Auntie Jamie, ...

1 year ago
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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
1 year ago
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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....

3 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

3 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

2 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine By: Beverly 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 Dr Shirley: 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 Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Gets A Black Master

Sissy Gets A Black Master I got up wearily from my long and exhausting night being fucked and punished by my new Black Master. As I awoke, I could scarcely believe that all those depraved things had happened to me. One minute I had been merely exchanging emails with a man, who could have been anywhere and the next minute, that very man was at my door, in my home, and then inside my body. Black Master, a man whose name I didn't even know, a man who looked to be about ten years my junior, had...

1 year ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
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Sissy Stepson Part 6 Carolines Sissification

Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I...

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