Anal Training Ch. 05

Story Info
Shopping in lingerie then sucking and fucking fun.
2.2k words
4.61
13.1k
7

Part 5 of the 5 part series

Updated 06/09/2023
Created 01/07/2020
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Hi Slut

Today we go further down the rabbit hole.

Before we do I need you to have the following items ready

- 2x dildos, realistic with suction cups , one bigger than other. I recommend 7" and 9" or bigger

- a small but plug

- a waist cincher or corset.

- a wig

- a make up kit including red or pink lipstick, foundation, mascara and eye liner

- stockings

- a short dress, tight fitting. It should be short enough that your panties can be seen when you bend over.

- high heels, ideally stiletto

- perfume

When shopping for toys, lingerie and make up, wherever possible, you are not going to do this online. You are going to do it in person in your local stores. And when you go out shopping, you will be wearing your panties.

Optional extra - DD or bigger breast forms. I recommend buying bigger e.g. E to F

ā€”-

First Step

As always, I want you clean so have a nice long soapy shower, we want you smelling beautiful.

I also want you hairless below the neck. I recommend gentle hair remover cream for your ass and groin. Shave your legs and armpits.

Next, put on your perfume.

Finally I want you to put on your bra, panties and stockings.

How do you feel pet?

Do you feel sexy? Do you feel like a pretty girl in your stockings and panties?

I bet your little clit is hard!

I bet it and your ass are desperate for attention.

You are dying to play? To fuck yourself or be fucked?

Bad luck, we're not ready to play yet. We're going out...

But first, we need one more thing...

Get your but plug. Lube it up. Slide it in. All the way.

No playing, just get it in. I know you can take it easily now with all the practice you've done....

DO NOT touch that little cock of yours. thats not for playing with today.

Now get dressed to go out. You can put on whatever you want over the top, but the bra, panties and stockings stay on and the but plug stays in. I encourage you to wear a white top, more see through, and tight shorts, that the panties can poke out of the top of... But I don't mind what you wear. If you're scared of people noticing, you can wear baggie hoodie. But we'll know what you're wearing underneath...

First stop, if theres one nearby, the adult toy store.

You're going to ask the clerk what their most realistic dildo is. Get them to show you. I want you to really ask questions about how it would feel. Ask what they recommend for anal play. If you haven't yet bought a suction cup dildo, now is your chance... While you're there look at some of the bondage gear. No need to buy any yet. Just take some time to do some window shopping.

I bet walking round that shop, filled with sexy things, with a but plug in your panty covered ass has you all hot and bothered...

I bet you're struggling to hide that little hard cock straining against your panties.

Ill let you play soon pet, but dont expect to cum anytime soon.

Next stop, the supermarket. Youre going to buy some lube and a cucumber.

Im tempted to make you buy only those two items. That'll get the people at check out talking...

But I also want you to get 3 items from the bottom shelf. I dont care what they are, but you're going to get them from 3 different aisles. When you bend over to get them, bend at your waist, keeping your legs straight. Show off that sexy panty covered ass of yours...

Do you think anyone can see your panties?

Do you think they know that your ass is full and stretching from your butt plug?

Now we're off clothes shopping. Somewhere with nice changing rooms with good mirrors. Somewhere that sells mens and women's clothing, ideally with pretty dresses and lingerie. Keep your new bottle of lube on your person.

Browse the woman's section... take your time, look at all the beautiful feminine clothes. Look at everything you can wear if you embrace your feminine side. If you become the girl you want so desperately to be.

Head to the changing room. Take a dress that you like if you've found one. if you're scared, you hide the dress among some manly clothes.

Strip down to your sexy bra and panties in the changing room.

Admire them in the mirrors. The sexy silky fabric, your stocking clad legs.

Do you feel sexy? Do you feel naughty in lingerie in a public change room?

Time to be naughtier.

You're going to take 3 photos of yourself in the mirror. Smile and pose nicely. Show off that beautiful lingerie youre wearing.

Now I want you to bend over, ass to the mirror. Pull your panties aside so that you can see the but plug. Take another photo. One that clearly shows the plug in your ass.

Now squat down legs spread wide facing the mirror. Reach down and, pulling your panties to one side, slide the but plug half out.

Then slide it back in again. All the way.

Repeat.

Use more lube if needed.

Fuck yourself slowly in the ass in that change room.

Watch yourself in the mirror as you do it.

Look at that desperate slut. Fucking herself in her ass , wearing pretty lingerie, in a public change room.

I bet you are close to cuming with excitement and adrenaline.

You might be caught at any minute.

Such a desperate little slut you are.

My good little fuck toy.

Stop.

Get dressed.

You can try on anything you want to. Try on that beautiful dress you picked out.

How does it feel my pet? Trying on beautiful dresses jn public?

Now put your clothes back on.

Once you have, its time to go. Feel free to buy anything that catches your eye.

If you still need make up then I want you to go shopping for it next.

While shopping you cannot tell the shop keepers you are buying for your girlfriend/wife/etc. You don't have to say its for you, but you mustn't lie.

Now at last you can go home.

~~~~~~~~~~

Are you home?

Good

I want you fully dressed.

Corset on.

Breast forms on.

Dress on.

Heels on.

Apply your make up.

Put on your wig.

Do you feel sexy my pet?

Good.

I want you to take 5 mirror selfies. From different angles. Try different poses, show off your ass, blow a kiss, etc.

Now you may take out your but plug.

If you need to, use a wet wipe to freshen up.

Now we can start to have some real fun.

Take the larger of the suction cup dildos and go into the kitchen. Stick it to the wall at about waste height.

Now on your knees slut.

You're going to suck that cock.

Start by kissing the tip. Then trace your lips up and down the underside. Lick it. Kiss it. Now take it in your mouth.

While you're doing this, slide one hand into your panties, you'll have to lift up your dress. Using one finger, start to gently tease your hole. Soft circular motions...

Take the cock deeper into your mouth. Good girl.

Start bobbing on it slowly going, sucking it like you used to wish someone would suck yours... Now however your place is here, on your knees, giving blowjobs, not receiving them.

Tease your little asshole in rhythm with your mouth moving on the cock.

Smear your lipstick all over that cock.

I want you to take it all the way in, keep going until you nose hits the wall, or until you chin hits the balls.

I know you keep gagging.

But you want to be a good girl, and good girls know how to deep throat a cock!

Keep going. It gets easier and easier the more you do it. Soon you'll barely have a gag reflex anymore.

Keep teasing your ass, you may use two fingers. Increase the pressure. But you may not slide anything in. Not yet.

Is your little cock hard while you suck cock on your knees my sissy pet?

Are you getting close while you gag on it with your fingers pressing into your ass?

Good girl.

See you really are just a sissy slut. Only a real slut would be so close to coming whilst sucking a cock.

Stop!

Get up!

I want you to tidy the kitchen and dust the house, but you're going to set a timer on your phone.

Every five minutes you get three minutes with this cock.

But there is one more catch. Every time the timer goes off toss a coin.

Heads, you spend 3 minutes sucking it with your fingers teasing your ass.

Tails you're going to grind against it, hoist up your dress, turn around and grind your boy pussy against it. Leave your panties where they are. You're not allowed it in your ass... yet. Just enjoy the feeling of the head of that cock pressing against your waiting ass. Teasing your entrance.

Keep going, following the heads and tails toss, until the kitchen is beautiful.

Do not cum.

I'll see you when the kitchen is clean and the dusting done...

Is the cleaning all done? Have you been a good sissy house maid? I think you may have to get a sexy maid outfit to work in soon.

And have you pleasured that dildo cock thoroughly?

Do you want to cum now sissy?

Good girl.

But no touching that little cock of yours.

Good girls cum from being fucked.

Get the dildo from the kitchen, and your second one.

Now on you hands and knees.

Carrying one dildo in you mouth and the other in between your thighs, crawl to the nearest doorway.

Crawl my little pet slut.

I want you to stick one dildo either side of the doorway.

Both a little over a foot off the ground. the larger one a little higher than the smaller

Lube up the small one.

Now position yourself between them slut. Wrapping you mouth around the larger cock. Guide the smaller one to press up against your waiting ass.

Using your fingers rub some more lube onto your waiting ass. Rock forward, take the big cock into your throat... now rock back and slip the other into your ass....

How does it feel slut. Pinned between these two cocks? As you can see, if you want to take one one of your throat you will have to take the other completely into your ass... if you want to fuck your ass you'll have to fuck your throat too...

Start fucking slut.

Ride that cock.

Suck that cock.

Don't touch that little clit-cock of yours.

In fact, tuck it between your legs.

Keep riding and sucking slut.

Harder.

Faster.

Imagine what it would be like if they were real. To have you ass/pussy and mouth used. To be fucked both ends at the same time. To be spit roasted between 2 cocks.

Harder slut.

Keep your little clit tucked between your legs.

Faster.

Ride those cocks. Rock back and forward. Sucking and fucking.

Give in to your slutty self.

You're getting close aren't you slut.

Good girl.

Keep going.

Harder.

Faster.

Deep in your throat.

Deep in your ass.

You love pleasing 2 cocks. You live to serve, live to be fucked.

Cum for me my pet.

Cum with a cock in your ass and in your mouth. Feel your little dick squirt hot cum down your thigh. Keep riding. Just a little longer.

Enjoy your orgasm as your rock back and forth. Your sissygasm.

Only a sissy cums like that. Only a real slut comes like that.

One last thing to do slut...

Reach between your legs and scoop up a handful of cum.

Smear it over the cock in front of your face.

Then lick it clean. Licking first then deep throating. Suck your cum off that cock...

My my my... we really are a desperate cum slut.

What a pretty little whore.

What a good little cocksucker.

Good girl. You can relax now.. You can take the cock from your ass..

Use your fingers to scoop up then lick clean any remaining cum.

You're going to stay as you are now for one more hour. Dressed like a little slut, the taste cum on your lips, with smears of cum down your thighs.

Once your hour is up you may shower and clean yourself up

---

Repeat the same tomorrow but with the big dildo in your ass.

Soon you'll be ready for the real thing. To dress up in sexy lingerie and get fucked and filled with cum at both ends.

----

Some tasks until next time my pet

- practice your make up

- you may not cum without a cock/dildo in your ass

- whenever you cum you must lick and swallow some of it

- I want you to take photos of yourself in lingerie in at least 3 different changing rooms or public bathrooms

- Take a photo POV style of you sucking your dildo like it was a real cock

-Take a photo of yourself fucking your dildo on the wall doggy style

- Write a list of men who might let you suck their cock

- buy some bondsge gear: cuffs, collars and leash, ball bag (preferably pink and fluffy)

- buy a sexy french maid outfit

- you can always buy more lingerie, dresses, skirts, costumes and make up

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  • COMMENTS
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5 Comments
AnonymousAnonymous9 months ago

Would love some more chapters!

AnonymousAnonymousover 1 year ago

As a sissy in training, this story has my little clitty dripping! Loved it

SissySlutUK222SissySlutUK222almost 2 years ago

When i read the list of stuff i will need, and already have it all, it makes me a little proud.

SissySlutUK222SissySlutUK222almost 2 years ago

As a sissy who has done her anal-training, I can officially say I like this,

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