Anal Training Ch. 03

Story Info
Continue your training. Become the sissy slut.
1.7k words
4.47
29.8k
16

Part 3 of the 5 part series

Updated 06/09/2023
Created 01/07/2020
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Hello pet. Welcome back.

Are you ready for the next stage in your training?

Good.

You're such an eager obedient pet aren't you? Such a slut.

Today you are going to need the following items

- Bra and panties

- Stockings, ideally with suspender

- Butt plug

- Vibrator/dildo

- Lipstick

- Perfume

You will also need plenty of time. I'm not going to let you just fuck yourself until you cum today. Oh no. Today you must be an obedient sissy slut the whole day before you cum.

I also expect, as always for you to be nice and clean.

You will also be naked and ready before we start any training session from now on.

Are you ready?

Good girl.

Lets begin.

Put on your stockings and suspender. Do they feel nice sliding up your legs? Do you enjoy their soft silky feeling?

Once they are on, rub your hands up and down over your new stockings. Savour the feeling of them.

Next put on your sexy bra.

Now walk up and down your room.

No, don't walk, strut! Do you feel sexy in your little outfit?

I know, you cant wait to put on your panties. Soon I will let you.

Get on your bed.

On your back.

Legs spread.

Trace your hands and down the inside of your thighs. Trace up and around that little cock of yours, but do not touch it. Continue down, around your balls, then down further toward yours ass. Gently trace your fingers around your hole. Nice and slow. Trace tight circles with just a little pressure. Linger there for a while... then back up and around your cock.

I bet your little penis is nice and hard for me.

You're so horny. So desperate.

Now grab your vibrator.

Turn it on.

Trace it up and down the inside of your thighs. Trace it up your cock and tease its head with the vibrations. Move it in slow circles around your cock. Find the point the vibrations feel best.

Hold it there for a minute. Enjoy the feeling of the vibrations.

Slide the vibrator down between your legs. Slide it down to your waiting ass.

Hold it pressed firmly there. Pulse it gently against your hole.

Don't try push it in. Just gently pulse it against your ass.

Savour the pulsing vibrations.

Good girl.

Now, slowly slide it the vibrator back up to your hard cock. Find the place it feels best. Hold it there again

With your other hand gently lube up your ass. Circle it as I have taught you. Little tight circles, gently stretching your opening. Start to slide your finger in. Slide in and out. A little but deeper each time. Slowly, in and out, deeper and deeper. keep up the circling motion. Each time you pull it out, massage a tight circle round your little hole. When you're all the way in keep moving your finger in a circle, gently stretching your ass.

Good girl, pet.

Keep holding the vibrator against your cock.

Keep fucking your ass slowly with your finger.

Are you getting close?

You want to fuck your ass with the vibrator now don't you? You want to be fucked in your little boy pussy?

Good.

But... not yet...

You will not cum yet. If you're getting too close take the vibrator off your little cock.

However if you do cum from just your finger in your ass... that's ok. That will just show you how much of a slut you are.

You would of course however start todays training all over again tomorrow.

Now

Get your butt plug. Lube it up.

Get on all fours pet. Ass in the air.

Such a cute pose. You're such a good girl.

Keep teasing your cock with the vibrator.

Push the butt plug up against your waiting ass. Start to push it in. Gently use it to fuck yourself. Deeper and deeper until its all the way in the base.

Now you may stroke your little cock. Jerk yourself off while the plug stretches your ass.

Do you want to cum for me?

STOP!

Take your hand off your cock.

You're still not allowed to cum yet.

Put your panties on.

Over the stockings.

Over the butt plug.

Over your desperately hard little cock.

You're going to go and do some chores for me.

I want you to go and clean the house. Like a good maid. You're going to clean the kitchen, vacuum, and the scrub the floors on your hands and knees.

And... you're going to do it all in your sexy lingerie. With your pretty panties cradling you little cock. With a butt plug stretching your little fuck hole.

Get to it slut.

This is the role of a sissy slut. To be fucked when you are told. To serve when you are to. To cook, to clean, then fuck some more, as and when you are told.

Once the house is clean I might let you cum.

Oh, one last thing. Every 15 minutes you will stroke your cock for 3 minutes. Do not cum! While you do it you're going to hold the vibrator pressed against your butt plug.

Have fun pet.

Cum back when the jobs are done.

----

Is the house clean my pet?

Is it spotless?

More importantly did you enjoy walking round in your sexy panties and stockings. Such a sexy maid you make.

Are you ready for more?

First, we have to make you presentable.

Go and tidy yourself. Wash your face. Brush your hair.

Next I want you to go and out on your lipstick. Sexy fucktoys must have lipstick on. Make sure you put it on neatly. If you have to, look up a how to video on YouTube, or better yet, online porn.

You like the way the lipstick feels.

Good girl.

Next a quick spritz of perfume. We want you smelling nice.

Do you feel sexy? Do you feel beautiful?

Such a cute little pet.

Now we can have some fun.

Crawl to the bed. Get on it on all fours.

You are going to start with blowjob practice, test out your new lipstick.

You are going to suck on your dildo vibrator.

Start by kissing and licking the shaft.

Swirl your tongue up and around the head of the dildo.

You know what would feel good. You also know that from now on your role is to suck cocks and be fucked by them, not to have yours sucked.

Take it into your mouth and suck it in earnest. Take it deep. Gag on it.

While you are doing this you have my permission to stroke your cock. Enjoy yourself while you suck longingly on the dildo.

Now the moment you've been waiting for. Take your lipstick smeared vibrator and turn it on. Slide your panties to one side and hold it against the base of your butt plug. Feel the vibrations fill you as you play with your little cock.

Pull the butt plug out.

Do you feel empty

We will fill you.

Lube up your dildo.

Use one hand to spread your ass cheeks as you kneel with your ass in the air. With the other one push the base of the vibe against your ass.

Slowly increase the pressure until it starts to slide in. Gentle pulse it in and out, all the while sliding slightly deeper.

Can you feel it filling you?

Start fucking yourself with the vibrator.

In and out.

Slowly siding deeper and deeper with each stroke. Turn up the vibrations to max if its not already on full. Start stroking your cock with your other hand.

Do not cum yet.

Do not stop fucking your ass, but if you are about to cum stop touching your cock.

If you cum from the dildo in your ass... good. That will just prove how much of a cock hungry little slut you really are.

Start thrusting deeper, harder, faster with the dildo.

Harder.

Deeper.

Sit up.

Hold the vibrator against your ass and sit on it.

If you need more lube on it, now is the time to do it.

You're going to ride it for me.

Again, start slow. but pick up the tempo quickly.

Rock back and forth, up and down on the dildo.

I want your ass bouncing up and down on that vibrating cock.

Go only as deep as you feel comfortable. But keep pushing a little deeper.

Deeper and deeper.

You may stroke your cock as you ride the cock in your ass.

Fuck that cock harder slut.

What a mess you are. Your panties pulled to one side. Your stockings bunching up. Your lipstick smeared. fucking a big cock in your pussy.

What a whore!

Fuck it harder.

Faster.

Cum for me.

Cum with that big dick stretching your ass like a good sissy fucktoy.

Good girl.

You loved that didn't you.

Enjoy your orgasm.

Enjoy the full, satisfying sensation.

Then gently remove the cock from your ass and go get yourself cleaned up.

---

Your assignments between now and next time

1) Every time you shower you are to clean your ass. Then using lots of lube you and going to finger your ass for me. You're going to experiment with what feels good. You may play with your little cock but you may only cum every third shower.

2) You are going to wear your panties more often. Any time you are home alone you are going to strip off and wear only your bra and panties, stockings optional.

3) When ever you feel yourself getting horny and hard you will play with yourself, but not with your cock. You will always reach first (with lubed up fingers, the plug or the vibrator) to play with your ass. You may only touch your little cock after you have fucked your ass first.

4) You're going to do some more shopping. You will need to get.

- more bras and panties. As you wear them more often you will have to be able to wash them and still have something to wear.

- a soft stretchy silicone cock ring set/ cock cage. Not a full chastity cage, just something stretchy that you can put around your cock and balls to remind you that from now on its your ass that provides sexual pleasure.

- finally some more make up. You will also practice applying the make up properly.

Have fun my little pet.

Cum back soon

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Catchandrea2397Catchandrea2397about 4 years agoAuthor

I am sorry if this story offended you. However some people do enjoy such things. It is by no means a commentary on all transsexuals, or any of them for that matter, but is an exploration of a fetish that some people enjoy

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