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Free Sissy Lesson: Anal Training

Do you like to take it up the ass? Of course you do! My sissies call me with the most astonishing variety of objects crammed into their asses, and I’m always shocked at the lack of education about proper anal play. There are definite do’s and don’ts to fucking your ass, and I am often asked by sissies to help them stretch their asses and train them for anal sex, so here I’ll lay out the rules you should follow for safe anal play, and discuss some examples of toys that are safe for putting up the butt.

Many sissies start their anal explorations with whatever phallic-shaped objects they have handy: flashlights, vegetables, bottles. Such objects can present a danger — without a flared base or a t-shaped bar, objects like these can be lost in the depths of your rectum and require medical help to remove. Objects with sharp edges can cut your insides up; chemicals not meant for human tissues can give you a rash or infection; breakable objects also present the prospect of picking shards of glass out of your ass. Not fun.

For safe anal pleasure, stick to either your fingers (with nails clipped and soap-and-water clean, or covered with a latex glove) or toys specifically meant for assplay. Below are some things to keep in mind when choosing something to go fuck yourself with:

Rules For Safe Anal Play

  1. Make sure that the item you are inserting has a handle or flared base. The anus likes to close the asshole and hold things inside of the rectum. Once you put something up your ass, you’ll want to be able to easily pull it out. Abide by this rule or you run the risk of being the topic of conversation over coffee at the local ER break room.
  2. Avoid long, inflexible anal toys. The anus is curved and it can be painful to push a hard, straight object too far in. All of your longer anal toys should be flexible.
  3. Start Small. If you’re new to anal play, then start with a slender butt plug. You can easily size your anus by slowly and gently inserting fingers, one-by-one, into your butt. The maximum number of fingers you can stick in will give you an idea of how big you want to go.
  4. Lube it up! Lubricant is essential to any anal play. The anus does not self-lubricate like the vagina does. So generous amounts of lube are required whenever you are going to stick something up your ass.

Anal Training with Toys: Exercises

Assume The Position

The “Feels Like A Woman” Position: Lie on your back at the edge of your bed or on the floor, then put your legs up and scoot closer to a wall so that your pelvis is lifted up into the air and your legs are splayed wide open. Now you can probe your hole with a dildo or vibrator while you milk your clitty into your face for a sissy facial.

The “Side-Saddle Sissy” Position: Lie on your side with the top leg raised up in the air. This is a good position for spending a nice long time exploring your ass with your fingers to lube it up and stretch it before sliding a dong in.

The “Doggy-Bitch Sissy” Position: Good old doggystyle is fantastic for fucking a dildo with a suction cup that you can stick on a wall, or reaching around behind yourself to pound a long double-dildo or a toy with a handle.

The “Sissy Squat” Position: Get a thick sturdy dildo with a base or nice heavy pair of balls and squat over it, pumping yourself up and down with your legs. Work those thighs, sissy!

The “LadyBoy Lapdance” Position: Similar in principle to the “Sissy Squat” Position, but this one is done by straddling a dildo with a base while it rests on the arm of a sofa or recliner. You can ride it while you pretend to show off your sissy moves to an audience, or just jerk your clit raw while you bounce on your dildo.

Stretching Your Hole

All ass activities should involve plenty of lube — my rule of thumb is “Use as much as you think you need…then add more anyway.” Go as slowly as you need to; it isn’t a race. Use your fingers at first, to get an idea of how much you can take, and then begin experimenting with toys such as dildos and butt plugs.

Ms. Liz’s Recommended Sissy Fucktoys

As you get more comfortable with penetration and discover what you can and can’t take, you can start working on stretching your limits with toys that gradually increase in size and/or girth. Below is a selection of toys from Eden Fantasys in a variety of anal-safe styles and sizes for Secret Sissies with virgin asses as well as experienced, wide-gaped anal sluts:

Fully erect realistic penis with suctioned base9 inch realistic dildo with balls and suction cup.Wet For Her Five is harness compatible and crafted out of 100% medical grade silicone.Purple silicone butt plugGraduately beaded silicone butt plugFirm jelly anal beadsSuction cup based jelly butt plugErgonomically designed prostate massager controlled by pelvic muscles.

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