tagBDSMSissy Shopping

Sissy Shopping


My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it.


You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year old girl in her livery; navy blue uniform, crisp white blouse with a name tag of Maria, tight navy skirt showing off her perfect ass, black seamed stockings and 5" black heels with ankle straps. She stands taller than you, around 6', and looked young, sweet and innocent, although with maybe just a hint of mischief in her eyes.

"Hi, you look a little lost, can I help?" she asked, in a soft, lilting voice

"Oh, um, I was just looking for some foundation, for my um, girlfriend."

"Ah of course you were, why don't you come with me and I'll help you find the perfect one for you. What sort of skin tone does your, ahem, girlfriend have?"

"Oh well um... I'm not sure."

"Is it like yours maybe? You have such pretty skin, is she as cute and pretty as you?"

"Oh um yes I guess it's quite similar." You say, blushing brightly.

"Perfect. Well you'll need quite a thick foundation I should think, and you look so pretty blushing like that some blusher too. All the boys will be after you, sorry I mean your 'girlfriend' of course."

"Yes, yes that will be great", you quickly reply, desperate to leave and hide.

"No, no, you aren't done yet; you wouldn't want to only look half made up would you? What about the rest of your make up, do you have eye shadow, eyeliner, lipstick, lip-gloss? I bet you don't even have nail varnish do you?"

"Um, well I'm not sure what my girlfriend has..."

"Oh, don't be silly. This isn't for your girlfriend at all; you probably haven't ever even had one. Now answer my question."

"No I'm sorry, I don't have anything." You quietly say, looking at the floor. You notice her fiddling with one of her ankle straps before slipping her stockinged foot out of her shoe. You are still staring as she starts running her foot up her other stocking, then down again, stroking her shoe before slipping it in and out of the gap between heel and shoe.

"Do you like my shoes?" Maria suddenly asks.

"Oh! Um I wasn't, well I..."

"Yes of course you were, you were looking at me playing with my shoes and stockings. You must have a shoe fetish as well as being a sissy, how cute! I wonder what you liked the most? Was it me stroking my stockings? Do you like the seams running all the way up to my suspender belt? Ooh actually today you're very lucky as I'm not wearing suspenders like I normally do."

You look a little disappointed as she said this, then she suddenly said "No, today I'm wearing a fully boned corset with attached 8 suspender clips, do you like the way it gives me this beautiful figure and pushes my boobs up?"

You must have been staring mute at her breasts for only a short moment, although it felt like forever until she suddenly said, "Maybe, maybe you were looking at my shoes? They have such delicate, long, thin, stiletto 5" heels on these. They are my favourite and I always feel horny wearing them. Sometimes I like to play with myself with them, sliding the toes into my pussy to get the soft leather nice and wet before rubbing my clitoris with the points of the toe. Then I slide the other heels into my mouth and suck on them while I fuck myself. I bet you were thinking of something similar, sucking and fucking my shoes."

I stared fixated as she slid her foot back in to her shoe before reattaching the strap and then walked behind the counter hiding everything from me except the by now huge erection trapped inside my silk panties.

"So anyway," she said, "we were working out all the things you'll need to be the prettiest sissy you can be, weren't we?"

She started to select some items from the counters before saying "Oh I know, we have a lovely starter kit here, they are just new in our Pink Princess range. You'd like to be a pink princess wouldn't you Sissy? I think I'll call you Sissy from now on; you look like a frilly, pretty, lacy girly Sissy. And I can see by your crotch that you think so too."

By now you are so desperate for relief you can only agree with anything she says and reply, "Yes that's right."

"What is?"

You blush again, "Um what you said..."

"What did I say? I want to hear you say it, it would make me so wet" she said as she slipped one hand into her blouse making sure I could see she was playing with her nipple. "Tell me what you are," she breathed in a husky voice that goes straight to your crotch and you burst out "I'm a silly frilly girly pretty lacy pink princess with bows in her hair". You have no idea where that all came from, especially the bit about the bows, but it certainly seemed to do the trick for Maria who had closed her eyes and now had her other hand down the front of her skirt. "Say it again... Now"

She looks so sexy playing with herself in her gorgeous uniform. Her other nipple was sticking very obviously out as you say "I'm a slutty pretty sissy princess in silky lacy underwear, a pretty pink girly dress and sexy, slutty fuck me shoes"

"Mmmmmm, God yes." she whimpers as she shudders her way toward orgasm, "Now tell me how you imagine you are being fucked when you are all dressed up."

You quickly tell her without even thinking your most frequent fantasy which springs to mind unbidden.

"I'm on my knees all dressed up in pink with a man stood in front of me, I reach forward and unzip his trousers, feeling his powerful erection through the material as it grows with each caress. The size scares me a little as it jumps out of his trousers, slapping my face suddenly with the full weight of his cock. "Good little girl" he says as he grabs me around my neck and guides his cock towards my lips."

"Yes more, more" she quietly squeals frantically fingering herself.

"He presses his giant cock against my lips forcing his way gently but firmly into my mouth as I stretch it open wide to take him all the way into me. More and more of his hot, thick manhood slides into my mouth, the tip of it pushing into my tongue before being guided upwards towards my throat. I hope he will stop but he doesn't and he pushes up against the back of my mouth threatening to make me gag, before he pulls out and begins to mouth fuck me. He holds my neck firmly and speeds up, filling my mouth over and over with his beautiful penis. 'Good girl', he says, 'suck my cock, you love it you filthy little slut whore.'

Suddenly Maria squealed again, this time without words as she violently came, her panties soaked with her juices. Recovering slightly and remembering where she was, she quickly adjusted her clothes that had become a little disarrayed.

"Hmm," she said, "thank you. Perhaps I can do a little favour for you now? How would you like to come to my place tomorrow night and I'll help you with your make up? Would you like that?"

You can't believe your luck and immediately say, "Yes please!"

"Well let's just sort out everything you'll need from here." she tells you, and quickly rings up a whole load of items including the starter kit.

"Now, what about clothes?" She asks you, "Do you have anything to wear? What about underwear?"

"Just the panties I'm wearing Maria, I'm sorry."

"Ooh you are wearing some now?" She says, reaching across towards your trousers. You back up slightly out of her reach, which causes her pretty smiling face to suddenly become extremely angry. "Don't you dare disobey me!" she says, "you are my little bitch now and you'll do what I fucking say, now as punishment for stopping me looking down your trousers you'll pull them down instead and show me." You gulp and hesitate, looking around to see if anyone was nearby. This prompts Maria to lean forward and slap you hard across the face. "Right you fucking whore, you are going to drop your trousers right now otherwise you can forget ever seeing me again. Now!"

You undo your trousers as quickly as you can and drop them down round your ankles, revealing the pretty yellow panties you have been wearing. "Oh how delightful," Maria giggles, "but you're going to need more than just panties for tomorrow night. It's time for my lunch break. Lets go shopping! You can pull your trousers back up now, although it doesn't look like you've got much to hide." You quickly do so, and then follow Maria out of the store.

She takes your hand and takes you to a nearby lingerie store that seems to specialise in very girly frilly clothing. "Okay you stand here and choose some underwear. I'm going to go and talk to the sales girl." Maria walks over to the counter and starts chatting.

You can't hear her that well, but you make out the occasional words as they look at you giggling. "Tomorrow night" you hear Maria say, shortly followed by "Fucked hard" and "lucky girl".

Maria finishes talking and walks back over to you, and asks what lingerie you've found. You suddenly remember you were supposed to have been choosing something, and quickly grab the first thing that you see and show it to Maria.

She looks at it and giggles, "Ooh they are nice, they even say 'Fuck Slut' on the back. But I think you'd look better in these." She hands you another pair of panties, pink frilly silk knickers with white satin bows around the edges, red hearts sewn around the main part, and pretty letters across the front that spell out "Sissy". "Oh look they're perfect, they have a little hole in the back in case you get lucky and pull a stud to ram his cock up your tight little sissy pussy, how wonderful. It even has more writing on the back, it reads Insert Here." giggles Maria.

You follow Maria around the store and hold on to the items that she picks out for you. One after the other, she picks out some pink, fine stockings, an overly frilly petticoat that looks almost solid frills and a hot pink and black latex nipple-less corset with attached suspenders. This is then followed by a very pretty dress with lots of lace and bows, and a nice puffed out skirt wide enough to take the petticoats underneath. Last comes a pair of 6-inch stiletto heels, patent black leather with pink uppers and a lockable band that goes around the ankle.

You are led by the hand to the back of the store to the changing rooms, and you both walk into the first one, pulling the curtain across behind you. Maria quickly strips you naked, before dressing you in your new outfit. After locking you into your new heels, she positions you in front of the mirror and you see yourself as a completely sissified slut standing with a beautiful young woman smiling wickedly standing behind you. She reaches around your body, and strokes your chest before sliding her hands inside your top and playing with your nipples. Leaving one hand teasing your nipples, she slowly runs her other hand down your body, her fingernails driving you crazy as you feel her tongue licking your ear and kissing your neck. You feel her hand reach your panties and she starts playing with your clitty making you groan with pleasure. "Tell you what, I can't wait to play with you properly, but why don't you put your hands behind your back a moment so I can reach you sissy clit more easily?"

You reach your hands behind your back, grasping for Maria, but she's no longer there until you feel her take hold of your wrists roughly. The next thing you hear is the snick, snick of a pair of cuffs clicking around your wrists! You try and pull away, before realising the handcuff chain is around a pole holding you firmly in place. Shocked for a moment, you open your mouth to ask what is going on when something comes over the top of your head, then pulled in towards your mouth! Maria tightens the gag around your head, fastening the strap firmly and wriggling the gag into position. It's a funny shape, long and round, and you are still running your tongue over it when Maria whispers into your ear.

"Hope you like cocks, you've got a nice big one in your mouth now! Now keep quiet for me, I'll be right back."

You hear Maria move the curtain aside and slip back in to the main shop, returning back a few minutes later with an odd plastic and metal device in her hand. She ignores you as she makes some adjustments to the device, moving some parts along different straps before turning to face you again. "Well this just won't do; girls don't have cocks in their panties do they? Let's just get rid of that."

She then starts slapping you, alternating between your face and cock, hitting you over and over until your erection goes down from all the torment. "Perfect, you look much more pretty now. Stay that way for me for a moment will you?"

She takes the device and inserts your battered penis into a tube, before pushing your balls into a little chamber at the bottom of the tube. It's then closed and sealed before having a pair of small padlocks attached and locked tight.

"Just to make sure you don't forget to visit me tomorrow." Maria giggles, placing a small card in your panties with her address on. "Come over at 8 O'clock, we can have some fun!" She tells you, as she leaves the shop after stuffing your clothes into her bag!

After a few hours of customers laughing and giggling at you whenever they go to try clothes on, with some having a little play and then laughing more when they find the CBT device the shop finally closes. You are released by the shop owner and have to walk home in drag. The shop owner lends you a small, tight dress which reveals more than it hides before kicking you out on the street. She throws your wallet on to the floor next to you, which you quickly pick up, hoping to be able to get a taxi. Looking inside, you sigh as you see the empty place for your credit cards, and no cash either. You put it away and start walking home.

Numerous wolf-whistles and drunken gropes later, you finally slip quietly into your apartment. Tired and exhausted you slump on to the bed, finally taking a look at the card that Maria had put in your panties. On one side was her name and address, and on the other instructions to shave all over before tomorrow. Despite everything, the clothing and humiliation you've suffered today leaves you incredibly horny, and seeing the card sends your hand quickly to your panties, eager for a play. The device around you completely prevents any kind of access however, and just leaves you frustrated all night long as you slowly shave your entire body.

Next day finally comes, and you head in to work still wearing the cage and panties. Distracted all day long, you are a little surprised when you get a phone call.

"Hello there Sissy! Hope you've been a good little girly princess and followed instructions? I bet you really enjoyed your time in the shop yesterday, I was laughing all afternoon thinking of all the things they would do to you! Now for your next task, which will be a lot easier if you've been good and shaved like I asked. I want you to go and buy some hair removal cream, and before you visit me this evening I want you to make sure every last trace of hair is gone and showered away. Oh and bring me a nice bottle of wine too; I like to enjoy a little tipple while playing with sissies. See you later!"

After a trip to the chemist you arrive home, cover yourself in cream and then shower it all off. You put your new clothes into a bag and take a taxi to Maria's. It isn't too far, and you are very quickly at her door, ringing the bell. Maria answers the door, saying "Glad you made it, come on in." as she leads you inside.

She looks even better than the previous day, and you feel your frustration even more as you take in her gorgeous form. Tiny, leather mini-skirt, black seamed stockings, knee-high leather high heeled boots already putting you firmly in your fantasies. Further up you see a tight black velvet corset with pink trim and a black choker around her neck revealed by her hair firmly put up.

"Now why don't you go through there, get some glasses and bring them up to he bedroom. I'll take your clothes and the wine. Oh and make sure you are naked when you get there. I don't want to have to start the evening with a punishment."

It doesn't take a moment to find the kitchen followed by the bedroom, and you walk in to the girliest, frilliest, pinkest bedroom you've ever seen. There is a large mirror on the dressing table, and a huge variety of make up arranged in front of it. Maria is already there on the bed, laying out your new clothes. She stands up as you enter, and points at her feet.

"Stand there. I need to make sure you have followed orders. Well you've obviously shaved but not to the standard I require. Stand with your legs apart, shut up and stay still. I'll finish you off."

Picking up some foam and a cut-throat razor, Maria walks grinning towards you before kneeling down in front of your caged penis. She removes the cage, then slowly, delicately covers you in foam and shaves you. You quickly get aroused from her touch, the feeling of fear and pleasure driving you to distraction. Eventually she is done, and you are now completely smooth. She then stands up in front of you, and without any warning slaps you hard across the face!

"You'd better lose that hard-on quickly, slut, because I'm going to really start hurting you if you don't!" Maria tells you as she continues to slap your face and cock hard. It doesn't take much of this punishment to lose your erection, which satisfies Maria for the moment, at least enough for her to stop hitting you. She then kneels back down and swiftly encloses you again in the cage. "Much better, I don't like to see pathetic dicklets like that. Much nicer all wrapped up. Now sit down here and put your feet up so I can do your nails." Maria takes a small bottle of bright red nail varnish and proceeds to paint your nails, toes first and then fingers. It takes a little time to dry, during which Maria leaves you in the chair with a collar and chain on and secured to the wall.

Ten minutes later Maria returns, and starts dressing you. Underwear first, the pretty pink sissy panties you had purchased the day before, along with your stockings and frilly negligée. Then your dress and shoes, before being sat down in front of the mirror for your make up. Lots of slutty thick make-up, deep red lips glossy and fuckable complete the look along with a curly, frizzy wig to top it off. A pair of falsies are slipped inside your top and held in place by your bra, perking you up nicely and giving you a very squeezable bosom. "I bet any man would love to be with you like this, they wouldn't just want to fuck your mouth they'd fuck you in the ass until you dripped with cum and couldn't walk for a week. Let's go have some play time and I'll take off that nasty cage, maybe we'll have sex and I'll get to fuck you, you sexy little slut."

Maria takes you by the hand and leads you to another room, feeling tipsy after the wine. It's dark inside, and Maria leads you to the centre of the room, guiding you to a chair and sitting you down before kneeling down in front of you, leering as she looks straight in to your eyes, fixing you to the spot. She kisses you along the inside of your legs, running her long fingernails up your stockings giving you a feeling like electric up your spine. Standing up, she straddles you and grabs your crotch, forcing her tongue into your mouth. The feeling is incredible as you feel her invade your mouth as she roughly gropes you, and you move your hand and hold on to her thigh to pull yourself closer. Maria immediately stops playing with you and pulls your hand away, putting it back down at your side. Rubbing your crotch again, she stops kissing you and stretches up, pushing her breasts into your face. You enjoy the feel and smell of her perfect tits in your face and you sigh as you kiss them gently, putting your arm around Maria to get even closer. The moment your hand touches her waist however causes Maria to jump up and slap you again in the face, before shouting at you, making you cringe in front of her angry expression.

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byCandour© 10 comments/ 175466 views/ 105 favorites

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