Making Of A Sissy (Part Four) free porn video

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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.

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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
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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
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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
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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
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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
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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
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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 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."...

3 years ago
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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
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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...

2 years ago
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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
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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
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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
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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
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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
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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
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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
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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...

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