The Regimen - First Iteration

The Regimen is a series of masturbation challenges that I designed for my husband to keep him busy when he only has himself to play with. I plan to post these as frequently as possible, however as a quality control measure I have my husband record his sessions for me, and I won't post a new Iteration until I observe him complete it.

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Welcome to the First Iteration.

Below are instructions that will take you through the 30 minutes of this Iteration. Each instruction is considered a "phase", and is assigned a time, so that when your timer reaches the time on the screen, you will proceed with the corresponding instruction. The goal of this challenge is to hold your orgasm until the clock reaches 30:00.

You'll also notice several checkpoints mixed in with the instructions. Because the goal of the challenge is to not orgasm until 30 minutes have elapsed, I created a few penalties for failure to keep the stakes high. Every time you pass a checkpoint, the penalty for failure changes.

Prior to Checkpoint 1, the penalty for orgasm is that you must instantly remove your hands when you feel the orgasm begin and keep them off your cock until after the orgasm subsides completely. This is called "ruining" your orgasm. Additionally, you will remain completely chaste for seven days (no sex or masturbation), after which you may attempt this Iteration again.

Between Checkpoint 1 and Checkpoint 2, the penalty for orgasm is to ruin your orgasm, and after it subsides you owe 60 seconds of slow stroking on your hypersensitive member. Since you reached Checkpoint 1, you may attempt this iteration again after only 24 hours of chastity.

After Checkpoint 2, if you are unable to make it to the 30 minute mark, you only need to ruin your orgasm with no additional penalty.

And if you make it all the way to 30:00, you win and may stroke to your satisfaction while you cum. Winning also unlocks the Second Iteration. So without further ado, here is a description of the different masturbation instructions that you'll receive, followed by the timetable for the challenge itself:

The strokes:

"Rest" - during a rest period HANDS OFF.

"Lube Up" - This instruction is usually the first phase of an Iteration. During this phase you are to coat your hands and member with generous lubricant. While you are directed to apply lube to your cock, you may not use this phase to jerk off, just focus on the task of lubricating.

"Tease" - a generic "tease" instruction gives you the opportunity to tease yourself as you like. You may tickle your balls or the head of your cock, stroke your shaft with a light touch, flick your frenulum with your thumb, or press heavily with your index finger on the underside of your shaft and run it up and down your cock. Also, if you require more lube, a "tease" phase affords you that opportunity.

"Balls and Head Tease" - lightly run your fingertips along your balls and the head of your cock. No touching the shaft.

"Light tease stroke" - this tease is a stroke, but a stroke where your hand is held loosely so you're barely touching yourself. Go at whatever speed you desire.

"Slow stroke" - using a single handed grip, masturbate in long, slow strokes that go from the base of your cock all the way up to the head. For an idea of timing, a "slow stroke" should take 5 seconds to complete one lap from base to head and back to the base.

"Medium stroke" - this stroke is the fastest stroke you'll use in most Iterations. Keep pace with the Bee Gees "Stayin' Alive". As with the "slow stroke" this involves long, complete strokes that stimulate the whole shaft and the head.

"Ring stroke" - make a ring from your thumb and index finger and stroke yourself from base to tip with just those two fingers. Use the "Medium stroke" pace unless otherwise instructed.

"Fuck it yourself" - wrap your hand around your cock as if you were doing a slow or medium stroke. No moving it though. The only motion will come from your hips as you fuck your hand at whatever speed you are able to.

"Head stroke" - the head is incredibly sensitive, especially after playing for a while, so I typically split this instruction into 30 second blocks. The first 30 seconds is a "Ring". You create a ring from your thumb and index finger, similar to the "ring stroke". Instead of stroking, however, you wrap that ring around where your cock head meets the shaft. You then rotate the ring left and right, stimulating that oh-so-sensitive head. This will be intense. The second block is the "Palm". Holding the base of your shaft in one hand, you press your palm into the underside of your cock head with the other hand and rub. Once again, this is very intense. You may lose your erection during this phase, but even if you go flaccid you may not stop with either the Ring or the Palm until your next instruction.

"Edge" - this instruction requires you to use a "medium stroke" to get right to the edge of orgasm by the end of the phase. I don't use the term "edge of orgasm" lightly: You are required to bring yourself to the point where you are a hairbreadth away from cumming, and you must do so before the end of the "Edge" phase. After reaching the edge, if there is still time left before the next phase, you earn a 10 second break, after which you need to edge again. You then will alternately edge and rest until the time arrives for the next instruction. This instruction is unique because it is the only instruction (so far) that can cause you to fail the Iteration without cumming. If you cannot reach an edge before the phase ends, you must stop without orgasming, and try again after 24 hours of chastity.

"Edge ride" - This usually follows an "Edge" instruction. An edge ride is like an edge, only more intense in that there is no 10 second break between edges. Your instruction is to bring yourself to the Edge and keep yourself there, your fingers dancing lightly over your cock or stroking lightly at whatever speed keeps you on the edge of orgasm without going over. This is incredibly hard to do without blowing your load, so odds are you may not make it to the second checkpoint on your first try. I apologize in advance for the ruined orgasm and the post-orgasm stimulation you'll have to endure.

Below are the phases for the First Iteration. For best results, open your computer's clock/timer, reduce the window size so it fits on the screen next to the phase list, and use the stopwatch option to time yourself. Make sure you're familiar with the descriptions above so that you can masturbate with minimal interruption.

00:00 lube up

01:00 balls and head tease

02:00 slow stroke

04:00 medium stroke

05:00 rest

05:30 tease

06:00 ring stroke

07:00 slow stroke

08:00 medium stroke

10:00 rest

10:30 tease

11:00 head stroke (30 sec ring, 30 sec palm)

12:00 medium stroke

14:00 edge

15:00 rest (CHECKPOINT 1)

16:00 slow stroke

17:00 fuck it yourself

18:00 edge

19:00 edge ride

20:00 rest (CHECKPOINT 2)

20:30 tease

21:00 light tease stroke

22:00 slow stroke

23:00 edge

24:00 edge ride

25:00 tease

26:00 edge

27:00 edge ride (no, it's not a typo: 3 minutes of constant edging starts now)

30:00 orgasm

If the stopwatch hit 30:00 before your blew your load, good job - you've unlocked the Second Iteration! And I'll post that once my husband is able to complete it.