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Day 7―P is for penetration



Dildo fun

We’re nearing the halfway point in the challenge. You’ve endured a lot of teasing over the past 6 days and of course the toughest days are still ahead as the days of your denial continue to mount. It only seems logical to give you a break and a chance to catch your breath by making Day 7 an easy one. But logic be damned. You were promised at the beginning of the challenge that it would be pedal to the metal from start to finish and that is exactly what you are going to get.

Morning assignment

Start your day by doing the usual 10-minute clit massage before getting out of bed, using the clit stimulation gel or liquid. Don’t forget to put on a pair panties before starting the clit massage since you were allowed to sleep without panties last night.
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The supplementary assignments that remain in play

  • Refresh the “TDG” printed on your inner thigh if needed (or re-print it if you wash it off each day). 
  • Panties still come off the moment you’re home for the day and aren’t to be worn while you are at home except when you are doing assignments and touching or at bedtime. 
  • You are still expected to do Kegel exercises each day, currently three sets of 8 repetitions, spread over the course of your day.

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Daily assignment

The focus today is on penetration so you will need your dildo again. Check the time when you are ready to start because I want a full 30 minutes of stimulation out of you today. 30 minutes is just a minimum however so you can go longer if you wish, just don’t get carried and cum or you are out of the challenge. You should be completely naked except for a pair of panties when you’re ready to begin.

We don’t want to forget about warming up, so let’s begin there to get ready for penetration. Devote the first few minutes to just rubbing the head of the dildo over your vulva over the fabric of your panties to get things warm and wet. After 6 days of teasing and no orgasms it shouldn’t take long to turn that steady drip into a gush of lubrication.

When you feel ready, push the crotch of your panties to the side and insert the dildo into your vagina. Start with some ultra-slow, shallow thrusts to allow your pussy to get accustomed to the fullness. Once things feel comfortable, work up to some deeper thrusts. As you penetrate, focus on the feel of fullness and where it feels most pleasurable with every stroke. Ease it in, slowly withdraw it, then slide it back in.

Once you are feeling nicely aroused and wet, increase the pressure and speed of thrusts. Concentrate on the feel of the dildo sliding and gliding effortlessly along the natural curves of your vagina. With each penetration, vary the angle of entry into your vagina so that every internal potential pleasure pocket is stroked, pampered, and caressed. Notice how the pressure points on your labia and vaginal entrance shift around as you change direction of entry.

Now change the angle so that the tip of the dildo is aimed upwards toward your stomach so that you access your G-spot. Find the pressure and the speed that feels best and continue thrusting and try to edge. After a few minutes of thrusting if you don’t seem to be making progress towards an edge, slip your other hand inside your panties and use your fingers to rub your clit. Every good girl should know how to multi-task.

Once you edge, stop the stimulation for a bit until your urge to cum subsides and then start again, either with just the dildo or in tandem with stimulating your clit with your fingers. Try to edge as many times as you can before the 30 minutes are up. Get close but don’t get overconfident. You don’t want to have any accidents after coming this far and almost reaching the halfway point in the challenge.

Once the 30 minutes have elapsed, the assignment is complete and you may stop and clean your dildo. As mentioned you can go longer if you wish but if you opt to do so, keep your hands off your clit and just enjoy the stimulation from the dildo. When you do stop, don’t forget to remove your panties until bedtime.
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Bedtime assignment

Once you have your panties on and are in bed it’s time for a little experimenting with a new way of touching and teasing your clit. Put your hand inside your panties and using your thumb and forefinger, grab, squeeze, and move the folds of skin that cover and are directly around your clit so that your clit is sandwiched between these folds of skin. That means that you won't actually be directly touching your clit.

When you squeeze those folds of skin between your fingers, you'll be able to feel the pressure it puts on your clitoris and it should feel really good. Keeping the folds of skin firmly grasped between your fingers, start to move your hand up and down like you are stroking a mini penis. Continue this until you achieve one last edge and then you may stop and go to sleep.

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