When will they ever learn?

I received a lovely email a while ago from a blog fan, stephen.

Hi Miss Julie!

My name is Stephen, and I've been a longtime fan of your site going far back into the Strict Julie Spanks days! I'm a 30 year old single guy living in the Midwest US.

Thank you so much for all of the content you've posted throughout the years. My interest has fluctuated during the years, but at times I've gone to you're page daily looking for fun updates before bed.

I'm writing to you because I've heard of your fun interactions with e-subs and would love to join the list. Anything public (such as shopping) is a little too far for me, but I'm interested in doing anything at home and would be happy to send you pics. I've found pretty much everything you post to be exciting and think I have similar interests as your lucky husband David.

Thanks again and I look forward to hearing back from you and trying to impress you!

Stephen

Isn't that a lovely email? It really keeps me going receiving nice emails like that. More of you should do it. I welcome it.

Of course, when a fan asks for an e-sub challenge, I'm only too happy to oblige. It literally takes me thirty seconds and will result in weeks of contemplation, preparations, second thoughts, questioning of existence, and so on from the poor dears. It will also become a highly sexually charged event for them, and will be a bit of an experience of a lifetime. The challenges I often recycle, knowing it will be a new and fresh experience for them.

I responded,

Hi stephen,

Thank you for writing! And thank you for being such a longtime fan through all my ups and downs.

Curious, as a longtime reader, what did you think of my "transformation" to becoming a switch? Do you more just wait around for the F/M content, or do you enjoy my M/F content as well?

But, down to business!

Let's do the toothpaste challenge. Get some nice minty fresh toothpaste and an old toothbrush. Wet your bottom hole, testicles, and penis, and then brush a good healthy quantity of toothpaste all around and a little into your bumhole, all over your balls, and then use the toothpaste as "lotion" for masturbating.

When you're at peak coverage, take a few photos. Then write me back a nice note detailing your experiences.

Be warned, I may choose to publish it and make fun of you!

Julie

That old classic, the toothpaste challenge.

I had first done it to david with my sister Sue present as recounted in My Sister and a good Toothbrushing. 

I got the idea from a blog commenter named ken2 when asking for suggestions regarding what mischief Sue and I could get up to:

While you want to refrain from rear end penetration this time, you can still enhance the exposure off his little pucker. Have him spread his own cheeks to show it off while over your lap (or Sue's). Then apply a dab of menthol toothpaste. That should result in some delightful pucker winking for your entertainment.

 I answered him as follows. 

Toothpaste on his bum hole? My my, what will they think of next! I have a love/hate relationship with this sort of suggestion. I would love to do it to him, but I feel like I would need to know how intense the experience is first, so I hope it makes you nice and hard knowing I will have to try it out on myself (in private, thank you very much) first, and I blame you!

That was over 10 years ago, now!

As  little extra backstory on stephen, this was not in fact his first reach out to me. In 2016 he had reached out from a different email account bearing a different name asking for a humiliating task (I know it's the same 'fella from the similar unusual email addresses and the similarities in how he described himself). That time I gave him one that was more public in nature involving going to a sex shop.

Humiliating task, eh... Careful what you ask for.

Ok, go to a sex shop, find a pleasant salesgirl, have her help you select a butt plug. Explain to her that it is a task that Julie, from Strict Julie Spanks, has assigned to you. Get a selfie with her and your plug. Then go home, stick it in, sit on it, and write me back with the photo enclosed. I will not publish your photo

Julie

That was apparently too much for poor stephen and he ghosted me after that email. Ha ha! He must have been so very embarrassed by the whole episode. I delight in the anguish I must have caused him with my quick little message!

So he very naughtily did not reference his previous failed attempt with me in this latest email. He was no doubt afraid of my reaction. Tee hee! But he did learn to include his boundaries in his latest ask:

Anything public (such as shopping) is a little too far for me, but I'm interested in doing anything at home and would be happy to send you pics.

That failed attempt must have been on his mind from 2016 until now. Seven whole years. Talk about living rent free! Plucking up his courage to write me again, determined to follow through!

The whole thing actually delights me.

A little bit more embarrassment than you were hoping for, stephen? Ha ha ha! 

Now, I had set stephen the toothbrushing task on April 28, and it was three weeks later and still no reply. I feared stephen was being true to form. But no! I received a response May 19. And come through this time stephen did. With flying colours. You have redeemed yourself, stephen!

Hi Julie :)

Thank you so much for your message! As a longtime reader, I was very interested in your M/F content as well! I've particularly enjoyed the series of posts of you embarrassingly having to admit your spankings and even getting spanked in front of others such as your parents (and admit it to them). I've always been something of a switch, but I would say my hearts does skip a extra beat when reading about your F/M stuff since you write it so well!

Ohhh thank you so much for the task!! I've never done this before. I did as you asked and attached pictures at various stages. I was particularly nervous about fingering myself but I did it! At first I didn't think the pain was a big deal and I started masturbating. It quickly (2~5 min from the start) began to get extremely intense and put me in a mild panic thinking "what have I got myself into"! My head went back to my cockiness fingering myself with a bit of toothpaste thinking that was a huge tiny mistake. I came quickly and immediately washed it off, which took away the pain pretty right away except for my bottom hole. Thankfully that felt better after 30-60 minutes.

Thank you so much for that challenge! Ohhh, publish it? You can do whatever you would like to do :).

For potential future tasks, just to get you a frame of reference, I have some items I can give you a heads up about. I have some ~5 butt plugs in various sizes, one short dildo that vibrates, 2 realistic dildos, a chastity cage, basic household items for spankings (although I can never go past the point of feeling much pain by myself), and some cute clothes - mostly sexy panties,

Thanks!

stephen

What a good boy! Let's take a look at his pics, shall we.

Here is stephen's bumhole before any toothpaste is applied.

And here we see how he's applied it to his scrotum and is pushing it up and all around his bottom hole.

Go stephen go!

All over the super sensitive scrotum. That's 'gotta burn!

View from the top

Don't think we don't see the panties, stephen!

Poor, poor, boy!

It's a pretty cock. Kind of skinny, right? Sometime I wish David's coke bottle cock was as skinny as stephen's. During punishment anal I would cry out, "oh Stephen! It hurts so much!" while sniggering to myself.

At first I didn't think the pain was a big deal and I started masturbating. It quickly (2~5 min from the start) began to get extremely intense and put me in a mild panic thinking "what have I got myself into"! My head went back to my cockiness fingering myself with a bit of toothpaste thinking that was a huge tiny mistake. I came quickly and immediately washed it off, which took away the pain pretty right away except for my bottom hole. Thankfully that felt better after 30-60 minutes.

Oh my! Such a rich mental image of stephen whacking off that poor little thing!

And then the worry afterwards when it just kept burning up the bumhole. I know after David had it done to him he spent 10 minutes in the shower fucking his poor asshole with a bar of soap! Perhaps young stephen was not as enterprising?

Well, thank you, stephen, for providing me, and now my blog readers, with this little amusement.

Boys will be boys...