As related in my last blog post, e-Subbie’s First Assignment, I gave a new eSubbie my standard first assignment. As it turned out, however, he had not been completely forthcoming with me regarding his previous experience, and as a result it made me seem unoriginal.

I solicited some ideas for punishment, and from those synthesized my response. Previously t had written an abject letter of apology to me after he had read my blog post. I told him I was teasing him. He wrote me another email where he seemed relieved by that, and referred to us as “BFF’s now”. He referred to me as “Julie” and asked if it was correct o lower case his name. Here was my response:

Yes t, of course you are lower-cased when corresponding with me. Address me as Ms. Julie from now on as well, please.

Since we are BFF’s, go fetch your largest dildo (or go out to a sex shop and buy a realistic looking challenging-sized one). Put it up your bottom. With it in, sit in front of your computer and type the following line for me:

“I must never again withhold information from Ms. Julie.”

Type it 50 times. Each time use a different arrangement of the words. Be sure to wiggle your bottom on that dildo as you do it.

Ms. Julie 

Well that got him jumping and resulted in a much more respectful tone in his following emails.

Ms. Julie – okay, thank you for clarifying conventions.

If I may, I do have two questions about this assignment.

First, I do not have a dildo, so I will need to go to a sex shop and buy one. In checking various types the Adam & Eve stores are likely to stock, here’s one that its web site describes as “Ignite 7.5″ Realistic Dong” and which is suitable for anal use. To me, this seems to be both realistic and challenging size (Realistically shaped head, shaft, and vein details / 7.5” total length, 6.5” insertable length, 1.5” width). Does this, or something like it, meet your expectations?

Second, to clarify the 50 line assignment.  To me, different arrangements of the words could produce nonsensical results, such as the second one:

1 – I must never again withhold information from Ms. Julie.

2 – Must never again I withhold information Ms. Julie from.

3 – etc.

Am I interpreting your instructions correctly?

Ms. Julie, thank you in advance for helping me understand and meet your expectations. I am learning that guessing or assuming anything is bad form for an e-subbie.

Regards,

t

I wrote back,

Yes, something like that will be fine, though I was hoping for realistic looking as well: skin coloured with veins and balls. They usually have pretty young ladies at those shops to assist you. Tell her why you need it, and ask her to help you confirm it is as big as she imagines you can take with a bit of pain and effort. Tell her about my blog. I’d appreciate the exposure.

Yes, exactly with the lines. The arrangements do not have to make sense.

And then his response,

Ms. Julie –  something more like this?

That was more like it! I wrote and told him so. I like it when they are eager to please. A few days later he wrote back,

Ms. Julie – I had a change of plans this morning, and ended up with some free time. Thus, I went by Priscilla McCall’s shortly after they opened, went inside, told the young woman working there the reason for my visit (recently began an e-Domme/sub relationship and displeased my Domme on my first assignment – thus, I was given this assignment as my punishment), either showed or read her the key parts of your emails, and asked her for help. She was quite gracious about it – perhaps a little taken aback at first, though she quickly adapted and went into “very helpful” mode.

I showed her the item I’d found on the web site and which I emailed you and asked her a couple times if this was as big as she imagined I could take “with a bit of pain and effort” – both times, she said this was a personal preference. When I told her I was new to anal play, she thought this would be as big as I could take first time.

I told her about your blog, and wrote down both its address (and encouraged her to visit it) and your email on back of a card at checkout, and told her she could help me out by emailing you with a brief note that she had helped “t” obtain the appropriate items (including lube and cleaner). My hand was shaking as I wrote this!

Okay, so prerequisites are done – now, to find the right opportunity to complete my punishment.

Embarrassed,

t

I had a block of time where I could complete my punishment in private. Thus, I got out the items I’d purchased earlier that day, cleaned the dildo before initial use, put lube on the dildo’s head, pulled down my pants and underwear, and began to insert it. The initial penetration was VERY tough and painful, and required a lot of effort on my part. Despite all this, I only got it in about 1.5 inches. Removing it, I spread lube on the rest of the dildo, and tried again – this time I was able to get the full dildo (5.5″ long and 1.5″ wide) completely inserted. This was VERY painful, pushing past the point I’d gotten previously. The dildo’s size took my breath away while I was inserting it, and I was VERY aware of it, even once I had adjusted to it a bit.

That was exactly the effect I was going for, so I was gratified to read that, as I am sure is the lovely young lady who sold you the dildo. You got it just right, girl!

At this point, I pulled my underwear and pants back up, to help keep the dildo in place, and proceeded to sit down and type my 50 sentences, generating different variations of:

“I must never again withhold information from Ms. Julie.”

Here are my typed lines – I began typing at 5:17 pm, and completed at typing 5:44 pm (typing time 27 minutes). Not knowing whether or how thoroughly Ms. Julie might check my work, I decided to check it myself – I’m glad I did, because I found 2 pairs of duplicated sentences. I corrected these, and ended up with 50 unique variations. I ended checking at 6:00 pm (checking time 16 minutes). Thus, I spent a total of 43 minutes seated, doing my typing or checking.

I must never again withhold information from Ms. Julie.
I never again withhold information from Ms. Julie must.
I again withhold information from Ms. Julie must never.
I withhold information from Ms. Julie must never again.
I information from Ms. Julie must never again withhold.
I from Ms. Julie must never again withhold information.
I Ms. Julie must never again withhold information from.
Must never again withhold information from Ms. Julie I.
Must again withhold information from Ms. Julie I never.
Must withhold information from Ms. Julie I never again.
Must information from Ms. Julie I never again withhold.
Must from Ms. Julie I never again withhold information.
Must Ms. Julie I never again withhold information from.
Never again withhold information from Ms. Julie I must.
Never withhold information from Ms. Julie I must again.
Never information from Ms. Julie I must again withhold.
Never from Ms. Julie I must again withhold information.
Never Ms. Julie I must again withhold information from.
Again withhold information from Ms. Julie I must never.
Again information from Ms. Julie I must never withhold.
Again from Ms. Julie I must never withhold information.
Again Ms. Julie I never must withhold information from.
Withhold information from Ms. Julie I must never again.
Withhold from Ms. Julie I must never again information.
Withhold Ms. Julie I must never again information from.
Information from Ms. Julie I must never again withhold.
Information Ms. Julie I must never again withhold from.
From Ms. Julie I must never again withhold information.
Ms. Julie I must never again withhold information from.
Ms. Julie must I never again withhold information from.
Ms. Julie must never I again withhold information from.
Ms. Julie must never again I withhold information from.
Ms. Julie must never again withhold information from I.
Ms. Julie must never again information from I withhold.
Ms. Julie must never again from I withhold information.
Ms. Julie must never withhold information from again I.
Ms. Julie must again never I withhold information from.
Ms. Julie must again I withhold information from never.
Ms. Julie must again withhold information from never I.
Ms. Julie must again information from never I withhold.
Ms. Julie must again from never I withhold information.
Ms. Julie must from never I withhold information again.
Ms. Julie must from I withhold information again never.
Ms. Julie must from withhold information again never I.
Ms. Julie must from information again never I withhold.
Ms. Julie must from again never I withhold information.
Ms. Julie must from I again never withhold information.
Ms. Julie from I withhold information again never must.
Ms. Julie must from I information again never withhold.
Ms. Julie must from I never information withhold again.

I have not checked it all all, pretty please would some of my blog readers proofread to ensure he did not shirk. Thanks!

As instructed, I did wiggle my bottom on the dildo as I typed the sentences or checked my work, making sure to do it at least once on every sentence typed and every minute or so spent checking. I typically bounced up and down every time I typed the word “withhold” – because withholding information was the reason Ms. Julie is punishing me. Every time I did this, my pain increased – I felt the increased pressure within my entire anal area, and the length of the dildo thrusting higher inside of me.

I was only teasing about the wiggling part, assuming wiggling would come naturally owing to the deep, deep penetration, but I am glad that t took me so literally!

After about 40 minutes, the dildo was becoming more painful and harder to tolerate. I sped up as much as I dared, knowing I needed to be thorough while I was self-checking my work.

Once I finished my typing and checking, I got up and removed the dildo. I was AMAZED at how empty my insides felt, now that this large piece was no longer inside me! I cleaned up myself and the dildo, and stowed it, the lube, and the cleaner in a secure place.

I sat back down to do some work, and realized how different my bottom felt due to having kept the large dildo inside me for 43 minutes – the entire area felt stretched and tingly. Upon waking up this morning, there was a residual feeling of “emptiness” and some tingling in my bottom.

Properly fucked! Perfect! This is how my husband feels after a vigorous session of anal intercourse from Adam.

Ms. Julie, I hope I have completed this punishment to your satisfaction. I experienced extreme embarrassment going to buy the dildo and accessories, and a lot of pain and discomfort during the 43 minutes of typing and checking. I also found the typing very tedious, because it was very easy to lose track of what I was doing – in fact, I lost my focus a few times and had to delete several duplicated sentences.

In conclusion, please trust me Ms. Julie when I say, I will NEVER EVER again withhold information from you!

Respectfully submitted,
t

Source: Strict Julie Spanks

e-Subbie Punished!