Day 5―Pain or pleasure

Clothes Pegs or Clothespins

What? Your pussy is begging for attention again? You’ve been teased relentlessly now for the past four days! Very well. But let’s introduce something new today. Something like a little pain. Pain is very subjective. What one girl finds painful another finds to be only minor discomfort and yet another finds the same sensations to be wildly pleasurable and arousing. Let’s learn a little more about you and what you find painful or pleasurable.

Don't worry. You needn’t be a masochist to survive this fifth day. The kind of pain I’m talking about is definitely of the mild variety. There won’t be anything extreme.

Morning assignment
Do your 10-minute clit massage before getting out of bed in the usual way. The clit massage should be second nature for you at this point so there should be any need any longer for reminders on how to do it. Just don’t skip the arousal gel or liquid.
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Supplementary assignments

Since I have added new supplementary assignments along the way, I will take a moment to summarize those that you are responsible for completing each day so that it isn’t necessary for you to refer back to the instructions for previous days. At this point in the challenge there are three supplementary assignments you are responsible for doing daily―

• Refreshing the “TDG” printed on your inner thigh as needed (or re-printing it if you wash it off at the end of each day).
• Removing your panties as soon as you arrive home each day and abstaining from wearing panties any time you are at home unless you are doing an assignment.
• Daily pelvic floor muscles exercises; at the moment the requirement is three sets of seven repetitions, spread over the course of the day.

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Daily assignment

First let’s get your wardrobe sorted. When you are ready to complete this assignment remove all other clothing you may be wearing and put on a pair of panties. The rules remain the same. You are only allowed to touch and play with your pussy while wearing panties. But since you will need more access for this assignment, we will modify the wearing part a bit. When you are ready to start the assignment, you are to push your panties down to your knees and then begin.

Next collect the items required for the assignment―3 ice cubes, 4 clothes pegs (clothespins), and a towel. The towel is to protect any surface that you don’t want to get wet from melting ice.

Let’s start with some cooling. Take an ice cube and rub your pussy with it for 2 minutes. Now try it on your anus. Rub your opening back there until the ice cube has melted. Now take the second ice cube and put it in your mouth for a moment. This is a precaution to make certain it doesn’t have any rough edges and doesn’t stick to your skin. Now take the ice cube out of your mouth and push it inside your vagina. Leave it there until it melts.

Now get the clothes pegs. Let’s start with your nipples. Use the last ice cube to rub your nipples until they are stiff and standing tall. Then attach one clothes peg on each nipple. If you haven’t played with clothes pegs before, attach the clamping part of the clothes peg at the base of the nipple next to the areola, not on the tip. There is no reason to waste the ice cube so after making certain it has no rough edges, shove it inside your vagina and let it melt.

Now your pussy. Attach one clothes peg to each of your labia majora (outer pussy lips).

Now it’s time to play with your pussy a bit. Start rubbing your clit fast and firmly until you edge. Once you are at the brink of orgasm and must stop to avoid having an orgasm, remove one clothes peg from one nipple. After a short break to allow your arousal to subside a bit, rub your clit fast and firmly until you reach a second edge. When you edge, remove one of the clothes pegs from one of your pussy lips. Repeat these instructions until you have edged twice more and have removed one of the remaining clothes pegs after each edge. Take a few minutes to catch your breath then continue.

Now that all the clothes pegs are removed, let’s move on to the final part of the assignment. Spread your thighs as wide as the panties allow. Start by rubbing your clit fast and firmly in a circular motion until you have completed 10 full circles. Now holding your hand straight with fingers together, spank your clit fast and firmly 10 times. Only your fingertips should strike your clit, not your palm. Make it firm but this is about sensation not real pain so don’t use too much force.

Repeat the above instructions but for the next round, do 12 circles and 12 spanks. On the third round, 14 circles and 14 spanks. On the fourth round, 16 circles and 16 spanks. Finally, on the fifth and final round, finish with 16 circles and 16 spanks. 

If you completed all the tasks above without having to pause to avoid having an orgasm while doing the circles and clit spanks, you may rub your pussy in any way you wish for 10 minutes. If you had to pause during the circles/clit spanks to avoid orgasm then you don’t get the bonus 10 minutes of pleasure.

Once you have completed this assignment, remove your panties and go about your day until bedtime.
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Bedtime assignment

Put on panties when you are ready for bed. You've had a lot of stimulation today so while touching your pussy is allowed, it's optional this evening and not required.

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