Sissy Shopping

"I get a call from a friend of mine that you were buying lingerie. Nothing strange you might say, you have lots, but this wasn't in your size. It wasn't in my size either. Now you are hardly likely to be buying such pretty clothes for just anybody my friend thinks. She decides to keep an eye on you, and watches as you buy a Valentine's card, chocolates and you order some flowers. This is very odd she thinks, who could these possibly be for? Luckily for me, she's a very sharp young lady and enters the florist shortly after you leave. She asks the lady about the flowers you just bought, and knowing your name she pretends to be the recipient and checks the name and address. So who is this girl I think? Who is Samantha? Such a pretty name, but it's not my name. Why would my precious Sissy Katie be sending Valentine gifts to another girl? I decide to find out and I visit her address."

Katie is now obviously shaken and is desperately trying to wriggle her way out, to no avail.

"Sure enough there is Samantha. She is very pretty, I can see why you like her. Older than me of course, and doesn't have my fantastic figure and dress sense. But that's not important. What is important is that my wonderful, my pretty, and my sweet little sissy whore has disobeyed me again. Now what to do with you? I tried to teach you a lesson before without success, so I'm afraid it will be punishment time again. I did warn you. I recorded a lovely DVD for you of some of your more intimate moments with my various male lovers, had a lovely big, red Valentine heart printed on the front with a little message saying how much you wanted her to be a part of your life. It said that you would be visiting soon, dressed just like in the video and that you were to start watching straight away. I wrapped it in frilly red ribbons, put it in a pretty little box with a pair of your frilliest panties and then gave the whole thing to my friend. She popped along to the florist and asked to have it delivered at the same time as the flowers. The florist thought this was a wonderfully romantic idea and agreed immediately."

"Now then, let's think what day is Valentine's this year? I believe it's tomorrow isn't it. Now do you think you'll be able to get to your girlfriends place before the flowers are delivered? Oh don't worry Sissy, I'll make sure you get there. Not sure how you will explain the box though. Anyway, now for the next stage of my enjoyment although probably not yours *laughs*. Okay boys come on in."

Two of the men from earlier enter the room, but this time fully dressed. They hold Katie down as Maria unties her arms and hands one at a time, before cuffing them to a wide leather belt that Maria slides around the sissy's waist. Next she fastens a metre-long leg spreader to one ankle before untying that leg from the stool and moving it far enough to cuff it to the other ankle. The spreader bar is then fastened to the waist belt as well, forcing Katie into an uncomfortable looking position. Her elbows are pointing out and upwards, causing her arms to stick out perfectly for being carried which the two men have obviously been waiting for. They pick up Katie easily, two big, strong butch men easily carrying the dainty fairy of a sissy between them. Katie's beautiful shoes and stockings swing about in the air, her frilly yellow panties poking out under her petticoats. Her legs are bent backwards and upwards towards her back pointing her toes skyward. As this was completed, with Sissy Katie completely under control, Maria walked over to the camera. Bending down to give a brief glimpse of her firm breasts trapped tightly in her corset, she scooped up the camera and turned, pointing it at Katie.

"I don't to want you to miss any of the fun." you hear her saying quietly, just for the camera.

You then watch as she is carried unceremoniously out. Mistress Maria must be enjoying herself with your backside as you feel her once again slowing, creating a slower but more powerful and deeper beat as she continues to fill you with her hard powerful love. Then once again she stops and gives you another powerful blast of cum lube making your bottom wiggle and your anal muscles contract slightly, which is rewarded with another dollop of goo shot up inside you. You pant appreciatively, enjoying the feeling of all that cummy lube going up inside you as the Mistress then slides herself out again, once more giving you the delicious feeling of that cum-like lube running down your ass and tickling your anus. You think there must have been even more this time, or there was still some from last time as you are sure it is running out more fluidly. You feel some reach your stocking tops, just like Katie, before Mistress returns with her next dildo to pleasure you with, and you feel a lot of the gooey lube being pushed back up and in and rubbed over the tip of her cock.

Your attention goes back to the film as you watch Katie being carried outside and dumped in the back of a pick up, completely exposed to anybody who came close enough, before the three of them climb inside the front and Maria begins filming Katie through the rear windows as she struggles against her bonds. Katie is looking quite scared and desperate now, but has no chance against the professional bondage. It turns you on to watch Katie writhing around in her sexy PVC uniform and frilly underwear which you get a frequent glimpse of as she rolls around. The bright yellow frillies show up starkly against the black of the uniform. You push back against the next cock that Mistress has for you, eager for it to enter you and give you another juicy squirt of her loving lube. The penis in your mouth has continued to go slowly deeper and deeper, and you are sure only your horniness can have allowed it to enter your throat the way it has. It has now pushed past the back of your mouth and your head has been forced upwards, with your lips and throat describing a straight line necessary for the deep throating you are now doing. Maria obviously notices you have been forcibly deep throating for a little while and adjusts your head harness and restraints to keep you in this position, without even breaking stride behind you.

Still firmly pushing in to you, the gradual building up of pain indicates this cock is much bigger than all the previous ones and it keeps on stretching you, wider and wider. You start to make little whimpering noises, prompting a slapped ass, until suddenly the end pops in and the force that got the big, hard penis into your ring now slides it home hard, making you squeak loudly as the base of the strap-on hits you. Your eyes bulge as the entire huge cock has gone from being completely outside to completely in within under a second, leaving you shocked and breathless. You silently thank Maria for all the lubricant She has been shooting up your backside all this time out of the end of her very enjoyable strap-ons. These three cocks have been growing steadily in size, and you wonder quite how big will she go with you on your first time?

The pick-up truck now stops, and the two men jump out and walk around, leaving Maria to keep filming. It's quite dark out, and they are obviously somewhere quiet, maybe a car park but you aren't sure. There is music coming from somewhere nearby, but unless Maria swings the camera away from Katie you won't be able to tell. The sissy is quickly lifted from the back of the truck and carried over to a lamp post, the only source of decent light in the area. It's in a slightly grassy area, just next to the concrete of the car park. With Maria following all the action, her two accomplices rapidly and with practiced ease hold Katie firmly while also tying her around the lamp post. Her ankles and wrists are both cuffed behind her, leaving her on her knees once again. In the dark she looks convincing, and after adjusting her wig and tidying her make-up a little they pop a piece of card on string around her neck and then hurry back to he truck. Starting the engine again, they move into a parking space with a good view of Katie, but behind another vehicle so it's not obvious they are watching. At this point you hear Katie say "Okay, now we wait. I'm sure it won't be long and they shouldn't disappoint." the video then clicks off.

A moment later it starts up again, cutting back in. The camera is now pointing at a couple of guys leaving a near-by building, you guess it is where the music was coming from. They seem a little drunk, and, looking closer, you think you recognise the building. It's a near-by strip joint, and reportedly brothel, but considered very rough with fights breaking out often. The two guys are walking back to their car and seem to be complaining about something. Probably just horny you guess after staring at a load of cheap hookers, but not quite cheap enough for these two. They keep walking and come into range of Katie's street light, showing them to be a pair of overweight, 50ish guys, one of which still has an obvious erection from the strippers. One of them notices Katie suddenly and stops, grabbing the other guys arm and pointing. It takes a few seconds to register and then the other guy is also standing there staring at Katie. Dressed in her shiny PVC she shines brightly under the lamplight and the two men slowly approach, looking cautiously around. Getting up close they lift up Katie's head, who tries to say something but can't because of the dental bit and ball gag in her mouth. They say something to each other which you can't quite hear and seem to be smiling as they read the sign hanging around her neck. Maria zooms in and you can also now read: "Free blowjobs for all, feel free to slap just remember to replace my gag after so I can swallow your cum."

The two men look briefly at each other before the one walking stiffly with the erection unzips his flies, pulls the ball gag out and rams his cock in. Katie starts choking almost straight away and tries to move away, but he grasps her head firmly and keeps ramming his cock in. This lasts only a couple minutes before he shoots his load in her mouth. The next guy is ready by this point and lifts up Katie's head to look in her mouth. She obviously doesn't want to swallow his cum and is trying to force her head down so it can drip out. You hear the guy holding her say "Swallow that cum you cunt! You think I want to fuck a mouth with his cum in? Stupid fucking slut!"

He then held her face with one hand and slapped it with the other until she gulped it down.

"Better bitch, and don't be so slow about it next time or you'll get worse than a slap and your pimp will be even angrier."

Obviously assuming Katie was a real girl, and a hooker to boot, he must have thought she was being punished for some infraction, and gentlemen these obviously were, they were happy to take advantage. After checking she had indeed swallowed all the cum he slapped her face a couple more times, this time with his cock, laughing to his friend that this was more the kind of money he wanted to spend on a dirty whore. In his cock went, not that big but he was very rough and Katie started to gag as he wrapped his hands behind her head and forced his cock in, holding her there for some time. Katie was uncontrollably bucking against the post causing her petticoats to fly up and reveal the frilly edges of her knickers.

"Hey buddy, check this out, I think she wants it from both ends!" laughing to each other the first man goes behind Katie, lifts up her dress, pulls down her panties a little and starts stroking his dick, getting ready to fuck her again.

His other hand stroked down her stockinged legs, and must have noticed the dried up cum still there from her earlier gang bang.

"Hah!" he laughed, "Looks like either she got fucked earlier or her pussy got so wet that it ran down her leg! This is great, I've always wanted to fuck one of these French maid girls in the ass, they always sound so dirty when they talk."

Now hard again, he spat on her ass and fingered her sissy pussy a little, before realising she had already been well lubed and used already.

"Damn hoe! Your ass is like a railway tunnel! How many guys have you had in here? Ah, who cares if you have one more then."

With that he slides his cock in, not as thick as Maria's friends but enough to make Katie squeal her little squeaky noises again.

"You know, I think the fucking little bitch likes it!"

"Who cares, she's just hear to get fucked I don't care if she likes it or not."

They continue to pound Katie roughly, when you feel Mistress once again ramming your ass hard after a fairly sustained steady pace. She shoots another gooey load inside you again, and then you feel her pull out. Another strap on shortly follows, and Mistress begins pounding your ass once again as you are now taking a dildo about an inch down your throat.

The two guys in the video finish with Katie, and then pop the gag back in her mouth like it said on the sign. Slumped across in front of the post, Katie looks distraught and scared, obviously with no idea where she was other than being outside somewhere and no longer safely with her former Mistress. At this point the video camera zooms in on Katie's tear streaked face, make-up ruined and smeared with cum as Maria starts speaking softly into the microphone.

"This, Sissy, is where you'll end up if you don't behave. I can treat you very well and give you many amazing experiences, but cross or deceive me and I will visit a wrath upon your life. My two friends here are going to keep an eye on Katie for the next few hours and film any more gang rapes that she endures which will be shown for your pleasure after this little talk. She will then be picked up, taken away and kept quietly until morning. Then, after we verify that the new love of her life has received her flowers and watched the video of her new beau performing so vigorously for me, we will drop off a little cum-stained package in her garden, all beautifully presented with a ribbon tied around her. A ring of the door bell and off we go, leaving poor little Katie to her fate with explicit instructions never to contact me again. I don't know what her new girl will make of it all, maybe she'll be disgusted, maybe she will be turned on and will keep Katie dressed as she is to torture and amuse her. I don't really care, because now I have my new play thing, You. My pretty little Sissy, you are going to bring me so much joy I'm sure. If you don't... Well Katie here could always do with some company but the gents here can be a little rough. One of my previous girls was hurt rather badly when they found out she wasn't really a girl at all. Poor little thing. But I'm sure you'd never do anything silly like breaking one of my rules. Anyway, let's watch Katie's next scene shall we?"

With that the video slowly zoomed back out from Katie's face and then jumped as the time shot forwards 30 minutes. A lone man was walking towards Katie, going through the same drunken surprise, delight and then horny routine as the last two. He is just reading the sign when the video suddenly clicks out again.

"Bad editing" you think being momentarily distracted by the cock in your ass ploughing you. Mistress must really like using this huge strap on you as she has been keeping it going for much longer than the previous ones. Video clicks back in and you are immediately greeted by a view down Maria's top before she moves back a little after adjusting the camera. She's wearing the same top as the one she was wearing for you earlier, and you can see another sissy behind being fucked by a tall black man, taking lots of long, slow strokes. He must have a big cock you think, salivating slightly at the thought. You can't see much of the sissy, only her legs which are wearing stockings and some really cute heels. You start to get very excited again by the view of Maria and this sissy getting fucked whilst wearing your favourite style of ladies heels.

Maria smiles and starts to speak "Hello there Sissy, this is a public service announcement. *laughs* I wanted to interrupt the video of Katie getting raped and covered with cum by all those unpleasant men to show you this Sissy here. You might recognise her in fact. She's been doing really well, and has already taken the hot dripping cum of several men in her sissy pussy and is now getting fucked by one my favourite studs. He has a gorgeously large penis, which has made me very happy on numerous occasions in the past. But for now he's pleasuring this sissy instead. Shall we meet her? Off we go."

Maria stands up, turns around and walks over to the Sissy Fucker Chair, still keeping between you and the sissy. She then turns around to face the camera again and says "I know you'll recognise her, because it's..." she reaches down to pull off the sissy's headphones when simultaneously yours are removed! You then hear Mistress Maria whisper in your ear "You."