The Day I Encountered A Sissy free porn video

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It’s a warm day when I arrive, you have followed instructions and have freshly shaved cock and balls, your pubic hair has been trimmed and you are wearing a nice lacy pair of panties. I am carrying a small bag with my equipment!!

Under instruction you undress me carefully, avoiding any contact with my swelling cock or balls. I put a leather collar around your neck and order you on to all fours. You are instructed not to touch your own cock whilst you watch me put my ball stretcher weights onto my balls, almost 2lbs of shiny steel that pulls my balls low. You can see but cannot touch!

Oh where shall we begin in our journey to abuse you and to make you cum like a fountain? You will be 100%Submissive – whilst I am experimental in how I degrade you and use bondage on you for my masochistic pleasure.

Suddenly I reach down and through your panties grab you roughly by the balls and pull you to your feet. I reach into my bag a pull out two lengths of cord, with one I tie your hands behind your back and then I rip of those oh so pretty panties that you love, and you are naked and helpless before me. With the other longer cord I bind and split your balls so that they look like two, increasingly purple coloured, peaches all tight and smooth. I reach again into my bag of BDSM magic and pull out 10 small shiny crocodile clips. One by one these are attached to the rim of your cock head, drawing a little blood as they bite into the tender skin of your dick. It hurts but I have forbidden you to so much as wince. A lot more joyfully painful than those sissy clothespins you have used before.

I leave you to feel the joy/pain for at least 10 minutes before releasing you from the clips and the ball binding.

Next from my bag is a ball parachute. I stand you up with your legs spread fit the parachute, making sure to avoid all contact with you now sore cock, and attach Weights of about 5lbs, which I hold suspended until all connections are secure then I drop giving a sudden tug of some force on your balls, you let out a loud noise for which you are punished with a crack of a little riding crop on your little white ass.



Now swing that weight and let the pull of the weights give you an ache deep in your little abused ball bag. But you have learned not to make a sound!
In the 30 minutes since I arrived you have watched my balls swinging around, slapping the inside of my legs and seen my cock get hard and strong. Oh how you wish that I would hold and gently caress your cock or that you could taste the saltiness of my pre-cum. Not yet…not yet!

I remove the weights and the parachute and untie your hands and order you to wait for me on the bed, on all fours again with your sweet ass in the air and your stretched balls not sure whether they want to hang low or withdraw up into your body for protection. You are facing away from the door so that you are unable to see me arrive in the room or see what I am doing, or about to do.

At least 10 minutes pass and you begin to wonder where I am, you know I haven’t left…you didn’t hear the door, but you are now wondering why the wait and what next? Then you feel me grab your cock and balls plunging them into a bag of ice and I tie that bag tight so that your balls almost instantly shrivel to the size of wall nuts. The ice cold is painful and you let out a wince, which is rewarded with 5 hard cracks of the crop on your ass.

2 minutes achieve the desired effect and any possibility of you cumming too soon has gone and I release your cock and balls from their icy prison.

The next thing you know is ass is being invaded and I tell you that it is a large black butt plug, and with the flick of a switch you realise that it is a gently vibrating plug.

“On your back sissy girl” I order.

Then I again bind your balls tight and tie the two ends of the cord to each of the corners at the foot of the bed. I then take each hand and tie those to the two top corners of the bed. Your are spread eagled with the plug still gently vibrating in your ass and your balls stretched tight. I raise your head on a pillow so that you can see what happens next. I produce my favourite toy, a twelve inch ribbed sounder rod that is 8mm diameter.

Taking hold of your cock I pump some lube in your peehole and gently but steadily work the sound into you. You can feel every rib as it pushes through the meat of your cock and then deeper and deeper. With the sound fully in your cock I sit astride your face and start to swing my weighted balls so that the soft warm touch of my taught ballbag brushes over your chin and your mouth. This is good you think, very, very good.

Time to remove the sound from your cock, release the binding from your balls and pull out the butt plug. But just when you thought release for all that cum might be soon I enclose your sweet little cock in a chastity cage. The dog collar goes back on and whilst you rest on the floor I relax for a while with a nice cold beer.

Time for the fun to resume with a BANG …….

With the butt plug back in, but this time with a much stronger vibration to drive you wild, I roughly push you onto the bed and having removed the chastity cage start to use a pin wheel on your little abused cock. The wheel with its sharp pricks runs up and down the length of your cock and I take care to press harder as I run the pinwheel around and around the head of your abused cock, all the time you feel simultaneous pain and pleasure.

Another break as we cannot have you cum yet. So how about a bit of cock bondage? Lets truss up your cock.

As I release you from the binding cords I once again sit astride your face, with my cock rubbing across your chin, your lips and your eyelids you feel the warmth of my pre cum on you as I take your little dick in my mouth and work around the head with my teeth. Suddenly the butt plug is out and is replaced with first one, then two and finally three fingers. All the while your cock is going deep into my mouth. But do not cum…. Don’ you dare cum or you will be severely punished….. so to save you a good slapping I withdraw and tightly squeeze my thumb over your urethra and put a finger hard on the end of your cock… that cum that is desperately trying to get out is for you, not me.
I let you subside for a while and again restrict your cock in the chastity cage and then order you once more onto all fours and I take my cock, still with the balls weights on, and ram it hard in your tight little man cunt. And as I pound your ass my weighted balls are swinging forward and back and are giving your balls a good bashing. Then just before I cum I roll you over and taking hold of my hard throbbing cock cum all over you…… over your face…..in your mouth…..over your chest until I am completely spent.

Now you sissy girl you can lick my cock clean, a small reward for my pleasure and a bit more cum in your mouth.

Finally girl it is your turn……………………….

I order you on your back with your legs spread wide. The Butt plug is back, with vibrations on full. I take some baby oil and smear it on your cock and I take your balls in my left hand and tug while squeezing hard. Then I take my right hand pull your foreskin back and in a slithery oily grip take hold of your cock. Pulling down on your balls I slide my gripped hand up and down, slowly and gently at first but gradually increasing my grip and the speed increasing it is sliding up and down the shaft of your trembling dick until you can contain all that hot cum no more and it explodes in a fountain all over you.

The relief you feel as your dick shudders and with each shudder a bit more cum seeps out. I take a drinking glass and scoop up your cum as you will need a little refreshment after all that exertion. There’s a good girl now drink that up it’s good for you.

And as I take myself to the shower you are to stay in your own man smell. I pack my bag of BDSM magic remove my ball stretchers dress and, 4 hours after we began, I disappear into the Night.

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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

2 years ago
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Theater sissy

This is a true story. No exaggeration, no BS. Hope you enjoy it.My ex girlfriend Tori and I had lived together for sometime. Our schedules were such that we had one day off together and one day off alone. I loved our together days but my alone days were porn days. And I LOOOVE porn.I would grab my case of beer, pack of smokes, a towel and head for the computer room. I would look up pics, vids, hop in and out of chat rooms. The whole nine. I was really getting into crossdresser vids at this...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

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