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| Anal Day |
Day 9 will be anal play day. I know some of you are into anal. Good
for you because today is all about the ass. But some will be new to it so we’re
going to dial down the level of difficulty just a little so that whether you
are a veteran back door player or a complete novice, everyone can complete this
assignment.
First, a word to the newbies. Keep an open mind as you approach
this. Many of us grew up learning something negative about our bums. So many of
the myths about anal sex will sound familiar. It’s weird. It’s dirty and messy.
It hurts. It isn’t weird. Depending on which survey you look at 20 to 45
percent of women have anal sex. As long as you practice standard hygiene, anal
sex is no messier than any kind of sex. Finally, anal sex should never hurt. If
it hurts you aren’t doing it right. So get beyond the “ick” factor and you will
give yourself the opportunity to enjoy a true erogenous zone filled with sensitive,
responsive nerve endings that can feel incredibly pleasurable to stimulate.
Morning assignment
Despite the theme for today, begin your day with the now habitual 10-minute
clit massage before getting out of bed, using the clit stimulation gel or
liquid.
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Supplementary Assignment
Yesterday you wore your Ben-Wa balls for three hours. Today insert them and keep then in for four hours. For the rest of the challenge, we will use Ben-Wa balls to accomplish the same purpose served by the Kegel exercises during the first week, to strengthen your pelvic floor muscles.
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Daily assignment
You may want to take a bath or a shower before beginning this
assignment. If you are particularly adventurous or have given yourself one
before you might even consider giving yourself an enema. Here is a tutorial link for giving yourself an enema if you’re curious.
Also make sure your fingernails are clean and neatly trimmed. Get a
handheld mirror and some personal lubricant. That’s all you will need. No toys
are required for this assignment.
Expect to spend about 30 minutes on the assignment so you will need
a private space for that period of time. You need to be completely naked which
is the state you will be in already of you choose to do the assignment
immediately after taking a bath, shower, or enema.
Lie down on your bed and take some deep breaths to help yourself
relax. You might even consider some soothing music, some candles, or burning
some incense to enhance the experience. Just do whatever helps you relax.
Begin my masturbating, touching and stimulating your pussy and clit
in the way you usually find pleasurable. You can even use a vibrator or dildo
if you wish or watch some good Tumblr porn during this part of the assignment.
Here the whole focus is getting yourself aroused. When you get aroused, there
is increased blood flow to your nether regions which is part of why
self-pleasuring feels so good. But not only do you experience increased blood
flow to your genitals during arousal but to your anal region too and that can
help you enjoy anal stimulation even more.
Once you feel relaxed, sufficiently aroused, and ready to explore,
find a comfortable position where you can easily use the hand mirror to look at
your bum. Lying on your back or sitting on the edge of either in a comfortable
chair or bed are the best options here.
Start by just looking at your anus in the mirror. Check out the
shape, size, and coloration of your anal opening. How does it look? Does it
appear relaxed, tense, or somewhere in between? Continue actively working on
relaxing―do some deep breathing, a little meditation if you are into that, or
even some Kegel exercises.
Gently massage your ass cheeks, your inner thighs, and the area immediately
around your anus. Massage, stroke, and generally explore the area tactilely to deepen
your feelings of relaxation and to get the blood flowing to your bottom.
When you feel ready, put some lubricant on a fingertip and gently
touch and rub your anal opening. Don’t penetrate it, just do some exterior
exploring. Stroke it, rub it, let your lubricated fingertip glide all over and
around it. Just stimulating the opening can be very pleasurable because of all
the nerve endings in the area. Focus on the sensations you feel, not just
around your anus but the rest of your body too, your pussy particularly. Does
it make you feel hornier? More wet? Spend at least half the thirty minutes on
this part of the exercise, touching, pressing, and stroking. Keep looking in
the mirror or put it aside now as you wish. If you wish you can even continue
rubbing your clit with the fingers of your other hand to get yourself even more
aroused.
Next it is time to explore penetration. Begin with one single, well
lubricated finger. Fingers are always best to start with when you are new to
anal play because you can really feel how your bottom responds to stimulation and
penetration. Insert just the tip of your finger into your anus and pause for a
few moments to get accustomed to the feeling. Then move your finger gently
against the sides of your inner opening without penetrating any deeper. Once
you feel comfortable, venture a little deeper with your finger. Soon you will
notice how your sphincter muscles feel around your finger. Take your time, and
be patient. There shouldn’t be any discomfort at all.
Now experiment with the different sensation you can produce with
just a finger. Do a slow, gradually deeper probe, venturing deeper inch by
inch. Experiment with different depths. Try moving your finger in a circular
motion just inside your opening. Leave your inserted finger motionless and try
rubbing your clit with the fingers of your other hand. Try some stroking,
pushing your finger in and pulling it out using different speeds and rhythms. If
you are experienced with anal masturbation or feel adventurous, after a few
minutes add more lube and try two fingers instead of one.
After the 30 minutes of anal stimulation you should be feeling
nicely aroused and your clit is likely screaming for more attention, but none
of that! Hands off your pussy now until bedtime. But it is anal day so feel
free to stimulate your anus anytime you like during the remainder of the day.
Just make sure you use lube if you doing any more penetration.
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Bedtime assignment
Since your clit didn’t get much attention today, once you are in bed
for the evening, do a 10-minute clit massage just like you do every morning
only you can skip the clit arousal liquid or gel for this iteration. Just alternate
the 40 circles with the slow 20 count breaks until the 10 minutes have expired.
Then it’s off to sleep for you. See you tomorrow for Day 10.

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