Becoming A Sissy Slut - Part 1 free porn video

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When I was a teenager, I went through a very tragic moment in my life. My cousin, who was like an older brother to me, passed away and left me in a very dark place in my mind. Seeing as how he was pretty much the only member of my family who I talked to or that paid any attention to me, his loss left a gaping hole in me that I never thought would be filled.

That was until a few weeks after the funeral a family friend, Henry, stopped by my house. Being as he was much older then me and I figured he was there to see my father, who lived with, but was either working late or romancing whatever girlfriend he currently had. When I told him this he shocked me when he said he was there to see me and wanted to see if I wanted to hang out with him. I was in such amazement that I had no idea what to do, but we started hanging out, going to different places, and even just chilling over at his house. Since it was summer I was able to spend more and more time with him, eventually being able to spend the night or the weekend with him. Every time we hung out I would look at him and see his smile, a smile that warmed me to the core, and a smile that would lead to more things. After about a month of spending time with him is when things took a serious twist.

We were hanging out at his house and since it was a hot summer day we were out back and decided to have a water fight. I got him a few times but he had decidedly won since I was soaked from head to toe. We were heading in when a blast from the A/C send a shiver through my body. He told me to go ahead and get a hot shower before I got sick so I made my way to the bathroom trying not to drip water everywhere. When I got there I stripped down and got in, enjoying the hot water compared to the cold wet clothes I had dropped in a pile on the floor. When I went to use the soap and shampoo I was a little confused because all I saw were feminine type products. Shrugging it off I used the soap and shampoo and enjoyed the flowery fragrance they left on me. When I finished I stepped out and dried myself off with the fluffy towel left for me. Looking around I finally noticed that the pile of clothes I had left on the floor were no longer where I had left them. I made my way down the hall to the living room where I saw Henry sitting on the couch, shirtless, watching something on the TV that he quickly paused as soon as he noticed me in the hallway. I asked where my clothes were and he told me they were being dried but he might have something for me to wear in his bedroom.

I followed him and sat on the bed, wrapped in the towel, the cold air starting to put goosebumps on my skin, while he searched through his closet. Finally he produced a large bag and smiled as he showed it to me and then proceeded to dump the contents onto the bed. I was shocked and really confused with what I saw. He told me all he had was his little sisters old Halloween costume that would fit me and what was on the bed started to make sense. There was a pair of black lace panties and matching bra, a plaid mini skirt, a white tie blouse, a pair of thigh high white stockings, and a pair of shiny black flats. I looked at the items and pondered whether to wait for my clothes or just suck it up. Another shiver running up my spine from the cold A/C made the choice rather easier. I bit my lip as I decided to just put the clothes on as opposed to sitting around in the cold in just a towel.

I slipped on the panties first, letting them slide up my legs before standing up to pull them up into place, covering my little cock in the smooth fabric. I could tell by the stirrings I started to feel that I was beginning to enjoy wearing them. Then I slipped on the skirt, the stockings, and the shoes, each piece of clothing becoming easier and easier to slip on as my resistance shrunk more and more. Henry helped put the bra on and finally I slipped on the blouse, tying it in the front. Henry stood back and smiled at me with that same smile that would melt me every time as I showed off for him. He told me there was something missing and dug back into his closet, quickly producing a box that he laid on the bed. I opened the box and inside were a red haired wig and a couple of strange looking mounds. He told me they would complete the outfit, so I let him help me with the wig and even sticking the, what I found out were breast forms, to my chest under the bra. He stood back again and whistled, turning me to look at myself in the mirror. I didn’t even recognize the person looking at me.

He took my hand and led me back down the hall to the living room, sitting down first and then pulling me down practically on top of him. As I landed next to him I had to brace myself, one hand landing on his chest and the other landing on his groin. I looked up at him shocked and apologetic but before I could remove my hand from his crotch he placed his on top of mine and just simply smiled at me. I was still a little confused but relaxed more when I saw that smile, although I could feel his cock growing under my palm. He nodded towards the TV and resumed the movie that he was watching before. I didn’t know what to think but on the TV screen was a woman with red hair and a man in nothing but shorts sitting on a couch.

The woman started rubbing the mans crotch through his shorts and at the same time I could feel Henry moving my hand to follow the same course. He told me to just pay attention to the movie and I watched the woman move faster and faster, so I started moving my hand faster to match. Then the woman pulled down the mans shorts pulling his cock out of his pants and grasping around it, stroking it up and down. I looked at Henry, smiling at me, and decided to follow along, pulling his cock out of his pants as well, stroking it in time with the woman on the TV. Suddenly the woman bent her head down, taking the cock into her mouth with ease, bobbing up and down on it again and again. I was confused but felt Henry’s hand on the back of my head pushing me down towards his growing cock. I can’t say I put up much, if any, resistance as I wanted to please Henry for showering me with such affection before. As my face got closer and closer I opened my mouth feeling the head of his cock pass my lips, the taste of his precum smeared on my tongue. I tried to take as much as I could but gagged time after time only able to get maybe half of it in my mouth. He reassured me and told me we would work on it. Watching the woman bobbing up and down I tried my best to match her speed. Then the man pulled her up and had her crawl on all fours in front of him. I pulled my mouth off of Henry’s cock and looked up at him, seeing him smile and gesture to the floor. With little thought I crawled onto the floor on all fours in front of Henry, feeling my own excitement in my cock as it leaked wetting the panties I was wearing. I felt his hands behind me, sliding the skirt up, pulling the panties down slightly exposing my ass but leaving my cock encased in the black fabric. Then I felt a cold gel pushed inside me by his finger, slowly pushing deeper and deeper. I groaned and moaned as I felt my ass opening and stretching to accommodate his finger. I felt him pull his finger out, my asshole seriously lubed, but leaving me with an almost empty feeling. I could feel Henry shifting behind me and my eyes went wide when I felt the head of his huge hard cock pushing against my hole. I cried out as he tried to push it in slowly, tears forming in my eyes. He placed something under my nose and told my to breathe in hard. I sniffed up as he squeezed the bottle as he pushed it into my nostril. My mind exploded in vibrant colors and any pain I felt seemed to slip away, replaced by a building lust and need. I felt him pushing his cock inside me again, this time there was no pain but rather a growing need to feel his hard throbbing cock inside me. Inch by inch he pushed it inside me, my ass stretching more and more. Moaning and groaning feeling more and more full I finally felt his hips against mine as he buried all of his cock inside me. Pulling back and pushing in again and again, faster and faster, deeper and deeper. His groans and moans made my body quiver with lust, my own little cock slapping me in the stomach leaving a thin trail. Louder and louder I moaned, starting to push back against his thrusts. Grabbing my hips I felt him thrust one last time, his cock growing inside me as he started to shoot his hot cum deep inside my bowels. I moaned like a whore as I felt his seed filling me up, my own cock spewing cum into the wet panties that encased it. He held me there as he shot load after load inside me, finally releasing his grasp as he finished. Still dazed I barely noticed his cock slide out of me, or the plug he shoved into my abused hole, keeping his hot cum in my belly. I was lost in list as I felt his hand on my head, turning it as he pushed his cock into my mouth. My taste buds exploded with the tastes of lube, his cum, and my ass, and as he pushed his cock in and out of my mouth I graciously sucked on it, cleaning it throughly. I felt his hands around me as he picked me up off of the floor and carried me to the couch, putting me cuddled up to him.

As I laid there trying to collect my thoughts and coming down from the lustfully high I was on, I looked up at Henry’s face and saw him looking at me with that great, warming smile. I smiled as well, feeling his arm encircle around me, the heat from his chest, his cum still swishing around inside me. I sighed as I snuggled into him, knowing that from that day forward I was HIS to do with as he pleased.

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So by this time I was a sissy with two lovers Peter and David the brothers next door. They were quiet different from each other, Peter tended to be the gentler of the two. When he fucked me, he would carress my sissy body, lick my nipples and toy with my boi clitty. When we had the house to ourselves we would make a date out of it. We would kiss on the couch and explore each others bodies, he would take me upstairs to the bedroom, I wouold suck his fabulous cock and he would then hike my legs...

3 years ago
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The Making of a White Sissy Slut

The Making of a White Sissy Slut When he replied to my ad online, Steven said he was an attractive, 30- something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I'd said something to offend him and responded by saying, "Well, no one's ever told me that I was unattractive." When I suggested that was because...

1 year ago
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The Making of a White Sissy Slut

The Making of a White Sissy SlutWhen he replied to my ad online, Steven said he was an attractive, 30-something, successful white man who was willing to explore the wild side.  When we met in person, I was more than a little bit disappointed.  Attractive was a stretch of the imagination and I told him so right off the bat.  He acted as if I’d said something to offend him and responded by saying, ?Well, no one’s ever told me that I was unattractive.?  When I suggested that was because no one had...

2 years ago
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The Making of a Sissy Boy Slut Part 1

Watching from the back of the large hall, I thought that the headmaster sounded a little slurred and was concerned whether he would still be able to give me a lift back home once the ceremony had finished, particularly as my father was away working and the night buses were infrequent at best. However, my worries were unfounded as, once all the guests had departed, the headmaster came and found me to tell me that it was time to leave. During the journey, which took about 30 minutes, the...

3 years ago
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Sissy Slut for Master S

Sissy Slut for Master S. I unlocked the hotel room door and stepped inside. The suite had two single beds so I placed my overnight case on the first eager to unpack. First out was a pair of thigh high, black PVC stiletto boots. Next a pair of black fishnet stockings along with the suspender belt to hold them up. My black PVC leotard. Black shoulder length PVC gloves a recent buy and my black rubber hood. The final item to make me look like a complete slut was my take tits! Bondage...

4 years ago
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Sissy Erotica Slut at the Truck Stop

A Night to Remember He loved being a sissy slut. He used to cruise truck stops, feeling the manly musk of sweaty truck drivers and other passengers. This old sissy slut would cruise the truck stop and check out who’s interested in getting their dick sucked in the bathroom, and then right there on the parking lot, he’d suck someone’s hard dick like there’s no tomorrow. He also loved to visit the cruising spots and public restrooms – they’d give him the much-needed pleasure. It was a nonstop fuck...

3 years ago
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The White Sissy Slave Society A Walk into Sissyhood

The White Sissy Slave Society: Sold into Sissyhood By Meeah Soo They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car. It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. I'm very easily intimidated. And there I was in a tiny plaid mini and white...

3 years ago
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Becoming a sissy slut 3

With Horses cum dribbling out of my ass, Michelle and i enter the day spa. A mature tall curvaceous lady greets us and leads us to a beauty treatment area two little thai ladies do our hands and feet , i have false nails glued on and painted white my toe nails are painted red. After this i have my facial hair removed by a laser. We are then told to go to the massage room where we strip and lie naked on the massage beds with a towel over our bottoms. The lady who greeted us at reception walks in...

3 years ago
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Caught and made into a sissy slut

It was for real this time. No fantasy. Reality. I was dressed up in red: fishnet stockings, g-string, and a babydoll. I was wearing a metal chastity cage that was pulling my clit down, and it was a clit, it only half filled the cage. I had a new cock too - a black face dildo which was double-ended. In my new role, I had to jerk it as I was fucked in my pussy and I was being fucked. She had fucked me so hard that I was completely submissive to her, sucking on my gag with wild abandon, a true...

3 years ago
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How I Became A Simpering Sissy Slut Part 2

Author's note: Thanks for all the positive reviews Lady's, Men, and Gurls! It fills me with joy to see that people enjoy my little twisted tale so far, and it makes my clitty hard just thinking about the fact that someone somewhere has wanked to something that I have created. Without further delay here comes part 2! How I Became A Simpering Sissy Slut Part 2 When I woke up I was in a large 4-post bed covered by luxurious pink satin sheets. My head was pounding so hard it...

4 years ago
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Becoming a Sissy Maid for Mark 5

Becoming a Sissy Maid for Mark & Rebecca, Part Five - Ms. Rebecca Tells Mark About Meeting Stephanie and More I continued telling Stevie about Stephanie and how I got to know her and her sissy, picking up from where I had left off with my having just finished sucking Mark to a climax and being told to share the news of my good fortune performing the research he had assigned me to complete for him. "Good girl, Rebecca," he said smiling. "I'm glad you still like sucking your...

1 year ago
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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...

3 years ago
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Sissy Slut Training Rules

There are a few things a Sissy must understand in order to attract, and then keep, her Man. Let’s look at them, these Sissy Rules.1. Men are superior to you. This is rule number one for good reason: it is a simple statement of fact. It’s so important that many questions that a potential Sissy may have can simply be answered with reference to this rule. And from this point on, references to real Men will start with a capital letter. So great is the level of superiority of a Man over a Sissy,...

4 years ago
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My Girlfriend madd Me a Sissy Part3

Here's the 3rd part of my story, I hope I didn't make you guys wait toolong. Hope you enjoy, its best read one handed ;-)My Girlfriend Made Me a Sissy - Part 3-------------------------------------------------I lay on Jess' bed waiting for her and wondering what would happen forages. She was in another room getting ready for her new lover, I wasalready dressed up. Pale blue, see through panties and matching bra, ashort black skirt and a blue vest top. With my make up done to show off mypretty...

4 years ago
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Sissy Slut

Sissy Slut by [email protected] ? I was naked and kneeling in the corner of the room furthest from the door. My head was bowed and my forehead touched the floor. I was shivering in anticipation because I had been that way for what I guessed to be more than half an hour, although it is hard to tell in such circumstances. Finally I heard the door open and the sound of stiletto heels on the painted concrete floor. They came towards me but I did not dare to look up. I knew that to do so would be...

2 years ago
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The Making of a White Sissy Slut

Truth be told, Steven wasn’t gruesome; he was merely average. Average for a white boy unfortunately is just shy of ugly. Thin lips, pasty skin, thinning hair, non-descript features, he was nothing to write home about. I had plans to change that. The ad to which he replied was a proposition to completely transform a white boy into a sexy, desirable, cross-dressing, sissy, and insatiable, cum-crazed whore for black cock. I didn’t pull any punches and he knew what he was in for so there was...

3 years ago
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Sissy Slut Gets All His Holes Filled

He was waiting for me as instructed, dressed in the bag of clothes I had left for him earlier in the week. I entered the motel room to find him sitting on the bed in the mini skirt, sheer blouse, lace topped thigh high stockings and stiletto heels from his goodie bag. With his legs crossed, he appeared to be quite demure but I knew the desperate, horny slut that was raging beneath the surface of his sissy attire. He knew I was the only person on the planet that could satisfy all his perverted...

Crossdressing
3 years ago
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The Making of a Sissy Boy Slut Part 4

--------------------------------------------------------------------------------------------------------------------------------------------- I spent the next hour on my own, cleaning myself up and tidying away the training equipment in the kitchen, until my attention was drawn to preparing my cum meal for the following evening. Miss Marsh had left me with a small Tupperware container, complete with lid so as it could be transported easily during my journey the following night, though I had...

3 years ago
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Mistress sissy slut

Waking up, sometimes, can be rather difficult to do, especially when you know that you were d**gged the night before. Or, at least you HOPE it was only the night before. And this time, it was far worse than the first times. So many things have changed about me from the first time I was d**gged, unwittingly and unwillingly, though as I look back, I can’t really say that I am upset about the outcome of each of these times. Well, I have to admit that I was, kind of, pissed off the first time, as I...

3 years ago
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Spying On My Sissy Slut Husband Part Two

After my last story of how my husband and I became lesbian lovers with him dressed as a female, both of us thought a lot about what was next for us.  I did tell him that I wanted to see him with a man.  Then that got me to thinking about a bisexual couple to play with.  A bi woman for me and a bi guy willing to fuck a crossdresser.  That would be perfect but so hard to find.My husband and I set a date for our attempt to find him a one-night stand playmate to fuck him.  The rules were set.  We...

Crossdressing

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