How I Became A Sissy Husband free porn video

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It all started when I was 18 years old. I used to hang out with my buddy next door and his sister, Sue. One day I snuck into his sister’s room and looked at, and then tried on, Sue's panties, garter belt and stockings. I then kept them on and went home.

I remember one hot summer day, when I was dressed up in her panties, garter belt, stockings, and wearing some high heels I purchased. I heard a car door slam so I grabbed my clothes and ran downstairs to the basement bathroom.

I just barely got the door closed when I heard Jim, who rented the apartment in our basement, coming down the stairs. But before I could lock the door he yanked it open.

Jim was a big 25 year old man who stood at 6 feet 2 inches tall and weighed 185 pounds. I had fantasies about him and would always wonder what he looked like naked. I would masturbate as I thought about him.

Jim looked at me holding my clothes but also still wearing women's under things. He laughed, and then said, ”I am going to tell everyone I can find, what you are doing.” I was mortified.

Jim said, ”But, if you suck my cock I won’t tell, it will be our little secret. I know you want to, so get down on your knees.”

I was so embarrassed and humiliated but also instantly aroused. My dick was hard as a rock and sticking out of the panties I was wearing.

He grabbed my head and forced me to my knees. He remarked about my cock being hard and took that as a sure sign I was his to command.

I did go to my knees as he instructed. He lowered his pants and pulled down his underwear, and out sprang his massive cock.

My goodness, I thought, it was so big. I guessed it was twice as big as my tiny 4 incher. His balls were huge and hanging down.

He told me to hurry, so I opened my mouth and took his soft cock into my mouth. I sucked and soon it was hard as steel. It was the first cock I had sucked. I guessed I was doing a good job because in only a minute he tensed up, grabbed the back of my head and unleashed a torrent of cum. The blast hit the back of my throat and the force made me gag. But he held me firmly to his cock and I was forced to swallow or choke.

He finished then released my head. I backed away; his beautiful cock slipped from my mouth.

That was when his friend Tom came in. “Holy shit, what the fuck is going on here?”

He saw it all.

From that day on, until I left for college, I was their bitch.

Many times Jim made me watch him fuck his girlfriend. When they were finished, I was ordered to clean her messy pussy and his dripping cock of all traces of their love juices. His girlfriend also would dress me in her girly things. Then she would put me over her knees and spank me for being such a sissy girl. But, what they didn’t understand was that I loved it all.

My only regret was his girlfriend never let me fuck her and Jim never fucked me.

Many years later, after I was married to Ann for one year, we were at a gathering. In private, Tom's now wife Pat asked Ann if she ever caught me wearing her things. Ann said she suspected I was a closet cross dresser but hadn’t caught me.

That night Ann confronted me about my past. She said she wanted to know if I still wanted to do all the things Pat told her I had done as a young man.

I confessed that I still had those desires. I told Ann that I had my own girly things stashed away in the garage. I also told her I dressed up and masturbated when she was out with her girlfriends.

Ann told me to get all my sissy things and dress up for her. I was in shock. I couldn’t believe my luck. I remember quickly going to the garage and getting my things.

Ann told me to strip and put on what I had.

I put on my thigh high black stockings, black panties, black bra and black wig and stood before her.

She ordered me to lie across her knees as she sat on the corner of our bed. She then pulled down my panties and gave me a severe spanking. Then she got mad because the spanking hurt her hand. She told me to get her slipper. She proceeded to spank me again until I was crying and begging her to stop.

She then ordered me to stand. My penis was sticking out just begging for release.

She said I could masturbate onto her leg. It only took a minute before I was squirting my pent up cum. I shot six long ropes of my juice all over her legs. She then told me to lick it all up. I hungrily did as she commanded.

She said the spanking was for keeping my desires from her. Ann told me to never lie or keep anything from her again. I was also ordered to never masturbate unless she gave me her approval.

From that day on I was her sissy. She introduced me to a lifestyle of humiliation. She gradually took lovers and had me service their every need. I became her cuckold, bisexual, cock sucking, cum loving, cross dressing sissy. I couldn’t be happier!

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The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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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,...

4 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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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
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 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...

3 years ago
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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
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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...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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How i became a sissy fuckslave pt3

At this point my entire body was in agony, my feet hurt from the ballet boots, my nipples were stretched at least an inch and felt like they were on fire, my balls had a deep ache in them from the weights and ball stretcher, my sissy cunt felt like a gaping hole and hurt like needles were being poked into it.i really hoped Sir would give me a little break before He started working my sissy cunt with His fist but alas this was not to be. He returned just a few minutes later wearing an elbow...

1 year ago
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How i became a sissy fuckslave pt1

How i became a sissy fuckslave.It all started after a series of failed relationships led me alone.Having always been a closet crossdresser, i started dressing more and more often and posting pics and vids of me on a website called xhamster.In time, i started posting vids of me toying my sissy ass, and also gradually building up my fem wardrobe. After several months and many pics and vids, i met a man who offered to train me online.This was mustually pleasurable to both of us and as time went by...

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