World Cup Chastity Game Rewards & Punishments: Punishment Report by submissive geek

As readers of my Male Service blog and Twitter feed know, I ran a "little" Chastity/Spanking/Edging Game for the World Cup. Among the players who weren't My subs, submissive geek was by far the best*, and we've been talking now about his Applying to Me.

*To Me, this means following my instructions regarding the Rewards and Punishments, including performing and reporting them in a timely and respectful manner, regardless of whether your team won or lost.

Those who played the entire game and won in the Final got an individually-designed Reward from Me, based on the Special Request ideas that they submitted privately as we began the Knock Out Rounds. This was their opportunity to ask for something extra special, new or different.

sophie was the only one who won this. Her request was to be sent to shop for a feminine outfit with a letter from me to give to the salesgirl. Yes, she got to enjoy every sissy's fantasy! 

She had a full day today of shopping (pic at right) and going to the salon, and her report is coming soon. 

The losers of the Final had to buy and wear black ribbons as cock rings in honor of the winner (Germany), and edge once while wearing it. 

That's jezi's hairy, censored, teeny peenie at left! (LOL!) 

submissive geek's somewhat more impressive pic is below. Since I'm considering whether I want to officially put him Under Consideration, I had him submit a detailed report. Besides, I knew many of you would be curious about how these last World Cup Rewards and Punishments went, and that he would probably welcome having his published. 

Enjoy! ;-)
*

My day started amazingly with a message from Mistress that, to my amazement, contained a recording of Her voice. It was so wonderful to hear Mistress Magick. I listened to it many times and it drove me crazy! Especially every time she said my name, mmm :)

Having been driven to new levels of horniness (on my seventh day of chastity!), I tied a black ribbon around my cock in honor of Germany. I wrapped a yard of silky black ribbon around my cock and balls quite tightly to make a cock ring effect and finished it off with a bow. I took a picture for Mistress. I then took the one edge Mistress had allowed me. It was very hard to stop wanking, but i managed to force myself.

Then it was time for my spankings: I owed Mistress 250(!), including interest, for backing Brazil in the game for 3rd Place. I decided to do them in sets of 25, alternating cheeks.

The first hundred weren't so bad, but after that they were landing on already sore skin and completing each 25 was very painful. I took a few pauses in between sets and managed to make it to the full amount. My butt was glowing, as was evident in the picture i sent to Mistress.

It was quite a pre-work session, and really hard [pun intended? ~ M] to just get dressed and head out without cumming. I was a horny mess all day at work and found it hard to focus.

The ribbon felt lovely though: the ends tickled and it held my package tightly, making it rub around more than normal. I made several visits to the restroom to tighten it up - i really liked the feel when it was nice and tight. It was a wonderful reminder of Mistress throughout the day.

Mistress was kind enough to IM with me that night, but primarily due to issues my end, it lasted less time than i would have liked. However, after much begging, i was allowed an orgasm! I removed my ribbon around 7pm, but unfortunately didn't have the privacy to cum, so had to wait another night and came in the morning instead. I tied my ribbon on again while i masturbated. i thanked Mistress Magick as i orgasmed, afterward licking up my cum from my hand as directed. i really am very grateful!

Mistress has decided to place me in chastity again, hopefully it won't be for so long this time! :)   [Don't tempt me, silly boy! ;-)]

SPH Punishment & Release by My jezi

I knew my jezi-darling would likely be offline for weeks during the holidays, as she always is, so I asked her to do my Holly-Day Assignment early. She's been my sissy for years and knows that I expect her to go shopping and submit her report as early as possible in order to help provide guidance for the newbies who may be doing my assignments. I shouldn't have to remind her, but I did to make sure that she was on task. She told me when she could do it, but then something came up, and the date just got later and later. Eventually, it was past Winter Solstice (My personal holiday) and almost Christmas. She was headed out of town with family and still had not done her shopping report or purchased her items!

This was not the first time this had happened. I've let her get by with too much in the past and have made it clear that I will be putting my foot down now. I decided that she needed a serious punishment - one that she wouldn't forget. 

First, I thought about having her order a realistic dildo like the one that I've had other subs buy to practice their cock sucking!

Then I remembered her teeny peenie, and some online role play that we had done involving this penis sheath/extension from Oxballs. (Pic at left edited from oxballs.com.) I decided that it would be far more useful to have her buy it due to the SPH (small penis humiliation) possibilities, as well as everything I had already contemplated with the dildo. ;-) And, yes, those punishments are still on the table. Unlike some sissies, she dreads the idea of cock sucking, so hopefully that will act as a deterrent in regard to future procrastination!
*

The time had cum for me to perform my Small Penis Humiliation punishment task for my delays and failures with Your Yule assignment and my lengthy absences over the Christmas Holiday period.

You, in Your wisdom had me purchase an extension sheath from UberKinky to show me just how teeny Your package is.

This was an extension [pun intended? ~M] of a yummy naughty scenario we had on IM whilst i was parked up alone before Christmas...... [*yummy memories*]

i prepared the 'thingy', as i have been calling it, and stripped so i was naked, nervously fingering the flexible, blue sheath.

i had been told to stroke and play with myself till i was hard and to show Mistress just how inadequate my size was by measuring myself against a ruler and then against the extension sheath!

As You can see from the images [which I've edited for the blog], Your package at its firmest is barely 3.5 inches long and pales into near invisibility when measured up against the shiny clear ice blue sheath!

As humiliating and upsetting as it was to show how small and sissy i am to You there was a tingle of excitement too which i found unexpectedly pleasing. i do hope that i was not wrong to feel so.... *blushes*

Having declared my sissiness to You by size in images, i was then to fit the 'thingy' to myself and show off my new found length!

This was an interesting and more exciting task than i had anticipated for i always approach new things with more trepidation than delight, and the thought of 'attaching' such a thing to myself did unnerve me.

The stretchiness and flexibility of the entrance and securing holes made my task much less daunting than i had expected. i am still not sure if it is best to secure balls first before attaching it over ones penis, or vice versa. i did experiment both ways without noticing a significant difference. i suspect i found that securing the penis first was marginally easier and more comfortable. [Yes, I would think that you would insert the penis into the shaft and then finish dropping the balls through the opening in the bottom before adjusting it tighter on the penis.]

To secure the device best one needs to squeeze the end to remove as much air as possible before slipping it over one's penis. this acts like a massive suction cup, holding your smallness tight inside the sheath as you squeeze your balls into the securing hole.

Here is Your package 'dressed' and prepared to please!

This was a unique experience and feeling, but one i feel sure will be repeated given Mistress and her wicked way of playing and teasing me out of myself, which, She knows, i love dearly, as i do Her. *blushes*

i was now to tease and play with myself whilst encased in the 'thingy' and only allowed to cum if it was whilst wearing the sheath!

i must admit that it almost caught me by surprise how quickly my new blue shiny 'cock' managed to cum! Barely was i on my knees in respect for Mistress, than i felt myself rapidly approaching the point of no return! i had just started to give the 'blueness' a squeeze, and the vacuum effect of the sheath upon my smallness worked quickly to sort of draw me out of myself. i was filled with a rush of excitement and thrill as within less than a minute my sissy cummie juices were inside the sheath!

My body tingling with the thrill and intensity of such a rapid release, i paused to utter our mantra, my devotion to You, my Mistress, giving thanks for the honour and pleasure You had bestowed on me with this new experience, pausing between each word to worship You and our being together:

Your gurl, Mistress.

Your cock, Mistress.

Your pleasure, Mistress.

At this point, i eased the device from Your package to show the creamy deposit i had made in Your honour.

Tipping the sheath up, i allowed the contents to run down its shaft and dribble into my waiting parted sissy lips, thanking You as i savoured the delights of my sissiness. *blushes*

The punishment complete, i washed the extension sheath inside and out, and put it away in a safe place.

Thank You, Mistress, for allowing me such a thrill and pleasure. It was intense and awesome, unexpectedly so as You know how fearful i can be of 'new' things.

i only have one negative observation from my experience and that is that the ball holding section does have cause to not remain in place fully. i suspect this is a personal thing due to my balls liking to 'retreat' within me when cornered as though they do not exist. i thought on this last night and perhaps fitting one of our cock rings first to make my balls more 'proud' would help this in the future, if it were not too painful! [I think you should give that a try next time. A ball stretcher might also be useful!] But, for a first time, i can find little cause not to give the whole experience, and humiliation of myself for You, a huge thumbs up! [;-)]

i hope that the report is satisfactory and makes You feel a little yummy. Performing and recounting this to You certainly was yummy for me! *blushes*

Much love and kisses,

Your sissy jezi, now SPH'd, blushing
xxx

*
UPDATE:

Some of my readers have asked how much jezi could feel through the sheath. I was wondering the same which is why I had told her that she could only cum if she came while wearing it. I responded to jezi with the below after I received her report:

"I was wondering how the sensation would be through the sheath. So you can still feel a lot? Or was it mostly the suction from being inside the sheath that you felt? Want to try it again then? *very evil grin*"

She responded:

*blushing*

The feeling of suction was unique for me, and i think with the squeezing of my hand, it just 'took me away'!  *blushes*

It didn't give me the chance to see if the act of merely stroking the sheath would be felt or not really. Apologies for that, but i am only a learning sissy. *blushes*

Of course i would wear it again for You, Mistress, and i am happy for You to share my thoughts and feelings if they may assist others.

Just writing back to You reminds me of the all too brief but thrilling moments, and i did enjoy reporting my 'size', and lack thereof, to You as well.

Kisses and love,

Your loving, adoring sissy, jezi
xxx

*

UPDATE #2: You can now read jezi's review of the Sheath at the Uberkinky site. I had her wait to write it until after she had worn it a second time, including quite a bit of testing (edging) time. ;-)