Anal Training Ch. 01

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First time anal experimentation joi for wannabee sissy.
942 words
4.36
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Part 1 of the 5 part series

Updated 06/09/2023
Created 01/07/2020
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This is the first in a series of sissy JOI training instructions. I want to provide real instructions that can be followed and enjoyed by anyone (well by any submissive sissy wanabee).

Please only read this however if you are over 18.

Feedback is welcome

***

Day 1:

Hello pet. Are you ready to have some fun? Are you ready to begin your training?

Get up and go have a shower.

Take with you some lubricant.

Wash thoroughly. Shave. Shampoo your hair, you will want to smell nice and feel pretty.

Once you have finished cleaning generally, start to focus on your more intimate areas. Then make sure your anus is nice and clean.

Are you ready to start having fun?

Are you ready to obey me?

Good

Get your lube. Fill the palm of your hand. I want you to lube up that little cock of yours. Use a flat open palm. Rub up and down the shaft. Are you hard for me? Good. Rub around the head of your penis. No grab your little cock round the shaft and start to gently stroke it, to jerk off yourself. Enjoy this because soon you won't be allowed to touch it. Soon you will cum only from anal. Soon you'll want nothing more than to be fucked in your boy pussy. That will be the only way you can cum.

Switch to just rubbing two fingers over the shaft and round the head of your cock. Rub it like you would rub the clit you wish it was. Now it is time to tease that pussy of yours. Using lube slide one finger down to your anus. Gently rub around your virgin hole. Tease and stretch the opening with a little pressure but do not try insert a finger. Apply a bit more pressure to your hungry hole. Feel it stretch a little. continue to rub small tight circles. Focus on the front of your anus slightly.

Now start to slide a finger in. Dont try go all the way in yet. Just slide in as far as you are comfortable. In and out. In and out. As you slide in deeper, run your finger in a circle. Gently stretching your ass. Then in and out again.

Start to stroke your cock in rhythm with your finger in your ass.

Do you feel like a horny sissy slut? Are you enjoying having your ass played with. Do you want to cum?

Start stroking you cock in earnest. Bring yourself closer and closer to cumming.

Are you about to cum?

Good.

STOP!

Stop stroking. Stop playing with your hole. Finish your shower and get dressed. Go get on with your day, clean the house.

Set a timer. every half hour you will be allowed 5 minutes to pleasure your self. You may not cum! You must each time gentle play with your ass as instructed above.

Come back for part 2 in 2 hours.

Part 2:

Are you horny? Are you desperate to be fucked? Desperate to cum? Good.

First make sure you are clean. if you have to shower again do it. Dont forget to take the lube and play with that virgin ass of yours while you're in there.

Now get naked and on the bed.

Get on all fours, bum in the air, lift it up ready to be fucked.

Run your fingers up and your shaft. Slide them down past your testicles. Rub up and down between your testicles and you ass, but do not touch that virgin hole yet.

Rub up and down. Each time slightly closer to that virgin ass. Until you touch it gently on each stroke.

You want it dont you? You want to finger your ass. Its begging to be touched. To be fucked.

Gently smear lube around your ass. Get that boy pussy wet and slippery. Now start to rub it. Rub small tight circles with one finger. Apply more and more pressure until you're stretching it open slightly.

Start to pushing your finger in. Just the tip, in an out while you're gently circling.

You want more dont you?

Ok slide your finger deeper. Each time you slide in and out fuck yourself slightly deeper.

In and out

Deeper and deeper.

Slide your finger all the way in. As deep as it will go. Hold in there. Deep in your ass.

Slide in in a circle round deep in your ass. Stretch your ass for me.

Good girl.

Roll over onto your back. And spread your legs. Start fingering that ass again. Keep going. Keep stretching it. Slide that finger in and out

Now you may touch your little cock.

Jerk off however you wish but match the tempo and pressure to your finger in your ass. Fuck yourself deeper and harder as you jerk off harder and faster.

Keep going as long as you can.

Are you ready to cum?

Cum for me!

Squirt your cum all over yourself.

Good girl. Good slut.

You loved cuming with you finger in your ass didnt you?

Keep teasing that little ass of yours as your cock twitches out the last of your cum.

Good girl.

I have an assignment for you now. I need you to get the following items for our future training sessions.

- matching bra and panties

- stockings ideally with suspenders

- but plug (i recommend a training kit with two or three sizes)

- realistic dong style vibrator (soft silicone/jelly style recommended; and yes you will be fucking yourself with it so choose your size carefully)

Now go get yourself cleaned up.

Come back for further instructions later.

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The author would appreciate your feedback.
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SissySlutUK222SissySlutUK222almost 2 years ago

was going to follow along but I'm already in full time chastity and already only cum from anal. so would it be ok to skip to the next stage?

AnonymousAnonymousabout 4 years ago
Ohhh Myyyyy๐Ÿšบ๐Ÿ’‹๐Ÿ’œ

Ms Andrea....thx for a luvly๐Ÿ’“ start for Crissy's training ๐Ÿก๐Ÿ’‹๐Ÿ’„๐Ÿก๐Ÿก. I find that damp Tampax feels delightful in my boipussy. Now if this naughty Pantyboi could find an understanding Mommy ๐Ÿ‘™๐Ÿ’‹๐Ÿ‘™๐Ÿšบ

SissyCrissy6245..........xoxoxo

TurningintoCDTurningintoCDabout 4 years ago
Great start!

You have a great, hypnotic style of writing :)

I loved following your instructions. :)

Please keep it coming!

I await your further instructions :)

AnonymousAnonymousabout 4 years ago

Loved it. I would like to be trained like that . more please!!!!

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