26/f - Decide the price for each of my orgasms in September

[garder80]

these posts are so sexy!
If you had tits I would consider you as a slave.

Keep up the horny posts, I'm looking forward to your horny denial ;-)

[Kate92]

Originally Posted by semper_virilis

I misread earlier so here's another/modified one in case the first didn't work.

In the 24 hours after you cum:

1. Don't wear a bra for all 24 hours.

2. Get yourself measured for a bra at a VS or similar. Ask specifically if they think you really need one at all.

3. You must cum again in front of your window and choose another payment.

This was the second payment that random.org selected for my 11th orgasm.

Task 1
This coincided with the punishment that is currently in place, and therefore turned out to be the easiest task of them all!

Task 2
I did this task on Sunday morning. My boyfriend had instructed me to wear a black and white striped long sleeved top and a short blue skirt for this task. It was quite cold outside so I wore a jacket as well. I drove to a store which specialises in lingerie, and was already feeling conscious when I walked up to an attendant and said that I wanted to utilise their bra fitting service. She passed me into the care of her colleague, an attractive woman who appeared to be in her mid-30s. She escorted me to a private dressing room and asked me to remove my jacket and top. I did so, my face reddening as I pulled the top over my head.

"Oh!", she blurted out as she saw me standing topless, clearly surprised. I soon found out why. "We generally recommend our customers to wear their regular bra when they come for a fitting".
And I wanted to crawl under a rock and die.
She saw my discomfort and said "Doesn't matter, let's measure you the old way!"
She got a measuring tape and ran it under my tits and around my back. Then she did the same around the fullest of my tits.
"What size do you normally wear?"
"32A", I replied.
She nodded, and said "I'll be back in a moment".

As I waited, I wished I was anywhere but in this situation. She returned a short while later with four bras in her hands and made me try them on one after the other and examined my chest and back with each of them on. The first one was a 30A. The second was a 32AA. Both smaller than what I thought my size was. I felt like I was going to die with humiliation. Both bras did feel a little uncomfortable though. Not obviously small, but slightly uncomfortable. The third one was 32A, and I put it on. To my horror she muttered, "Cup appears a little too big". I looked down and saw that there was a very slight gap between the cups and the tops of my boobs. The last one was also a 32A but had a slight padding at the bottom of the cups. This lifted my breasts slightly so the top of the cups sat snugly against my flesh. She nodded as if making up her mind.

After I had removed the bra and put my top back on, I asked her with a great deal of trepidation, "So what is my correct size?"
"The closest fit is a 32A, preferably one with a slight push-up for a better fit, like the last one you tried on."
I was holding my breath and finally released it in relief. I had been half expecting her to mention one of the smaller sizes.

I was following her out of the dressing room when I remembered the last part of the task. Haltingly, I asked her whether I needed to wear a bra at all. Just asking the question made me want to run away and hide!
"Well...", she started, then hesitated. Took a deep breath and carried on, "Yes, I would probably recommend that you do. Besides, you've got...", more hesitation. "You've got sizeable nipples, so a slightly padded bra would be recommended. It would also be beneficial all-round, especially one with a slight push-up....", and she stopped there, hoping that was enough to get the point across.
It was. The message was clear. Her view was that my tiny tits probably needed a bra but my "sizeable" nipples definitely needed one - a padded one so they didn't stick out so obviously, and have the extra benefit of making my tiny tits appear bigger. I thanked her and left the store, and even though the type of bra she recommended was more or less same type and size I had been wearing for years, I left feeling more embarrassed than I have probably ever felt!

Task 3
When I reached home and relayed what had transpired at the bra fitting to my boyfriend, he laughed. "I guess you want to cum now?", he asked. And he was right. The humiliation had, of course, made me stupidly horny. I stood in front of the window in the living room, and removed my skirt. I was naked below the waist but no one looking at me from outside would be able to tell. As it was, I didn't spot anyone at any of the windows in the houses across the street. My boyfriend, sitting in an armchair next to the window, made me spread my legs and then held my magic wand vibe against my pussy and clit and turned it on. He started at a low speed and built it up gradually until I could barely keep my balance, my moans building in crescendo. I was thankful that the window was at least closed which would - hopefully - muffle my sounds.

I was gripping the inner window sill to keep myself upright as I felt the orgasm approaching. And then my boyfriend pulled the vibe away from my clit, making me howl in frustration. I looked at him with pleading eyes and he grinned as he again pressed the wand against my clit. I edged again in no time but he again pulled away. I started begging him to let me cum, and the wand was back against my clit, making me moan. I looked outside and my heart skipped a beat as I saw a man at his window in one of the houses. He wasn't looking up at me, but that didn't stop me from trying to restrain my moans.

My boyfriend guessed I had seen someone and he started a cruel sequence of holding the wand on my clit for a couple of seconds and then taking it away for a second. The start-stop sequence made me lose control of my moans. I was getting closer and closer to the orgasm. I started pleading with him to just let me cum, and he finally relented. The wand wasn't pulled away this time and it quickly pushed me over the edge, my legs buckling under me so that I dropped down on my knees as I started cumming. Because of this, the wand lost contact with my clit and the pleasure began dropping off rapidly, and I was fearing a ruined orgasm when my boyfriend salvaged it by finding my clit again with the wand. The pleasure came back and I eventually managed to have a decent orgasm, though a few notches less intense than it should have been.

As payment for this orgasm, I took a huge risk. I decided to try my luck with another double-or-quits, even though I knew that the law of averages was completely stacked against me this time. I let my boyfriend generate the number on random.org as I couldn't bear to look. "You should try your luck at a casino", he exclaimed. I stared at him and he showed me the result - 87! I couldn't believe my eyes! Another free orgasm! I collapsed onto the floor, laughing with relief.

- Kate

[Kate92]

That was, sadly, my last orgasm in September. I fully intended to cum a couple of times on Monday the 30th - my boyfriend and I had planned to meet at his place after dinner with that very intention. But between afternoon and evening, I somehow managed to fall quite ill with a cold and fever that suddenly crept up on me. So my boyfriend came over to my place instead and took care of me. We were, naturally, unable to do anything kinky.

I took the day off work yesterday to rest and am in much better spirits now, but I am rueing the fact that I missed out on a couple of orgasms! I tried to see if my boyfriend was open to letting me cum a couple of times today in lieu of the missed opportunity, but he dismissed the idea by simply stating, "September is over, Kate". His tone indicated that pursuing the matter further was futile. His dismissive manner left me hornier than before.

And thus, my September adventure has finally come to an end. A total of 12 orgasms in the month. Could I have cum more? In hindsight, probably yes - I think I was too circumspect in the middle weeks of the month. Regardless, I had an absolutely fabulous time, thanks in no small part to the wonderfully innovative tasks that all of you set for me! My boyfriend has indicated that he intends to make me do many of the unused tasks in the coming weeks.

Thank you all for your participation in the thread, and I hope to see you soon on my next one!

- Kate

[ltakltak]

Wow, this bra-measuring was a classic but a real good one to humiliate you (or anyone of your "breast" size. Another pleasure to read your orgasm adventures. Looking forward to the non-orgasm adventures due to come next ;-)

[cl61]

Originally Posted by Kate92

While a punishment is already in place for not attempting this payment earlier, my boyfriend believes that I deserve another punishment for failing this time around. He leaves the final decision with cl61. Please feel free to add a further punishment if you deem it fit.

It would be very discourteous to ignore your boyfriend's advice. And after all, he is the man on the spot and has your best interests at heart. So I'm sure he is correct that a punishment is necessary.

Since this is the second punishment for this payment, I think we should make it intersect with the first one. Therefore, given that you are not wearing panties to work for the remainder of this week and all of next week, this is the first part of your punishment:

Each day during this period, while out of the house, you need to wear either:

• A binder clip on each labia for 10 minutes, or
• A knotted crotch rope for 20 minutes. The knot should be placed over your vaginal opening, but you can add another one near your clit if you wish.

It's up to you when you carry this out — on a work day you could pick your lunch hour (if you have one), or if you choose the crotch rope then you could wear it while commuting to work. The only condition is that you should not hide in a toilet cubicle (or similar) while you do it.

At the weekend your boyfriend should choose where to take you. Either way, this is intended to ratchet up your moisture management problem just a little, both from the punishment and, perhaps, anticipation of the punishment.

Second, when an appliance is broken it should be repaired. Although you did very well with the payment — it's hard not to startle under the cold shower, which makes the task nearly impossible — the satisfaction of someone's cock could one day depend on the toning of your vaginal muscles. So we should try to get you keeping the dildo in for longer. This is the second part of your punishment:

Each evening when you get home, you should strip naked and remain naked for the rest of the evening. Repeat part 3 of the payment, in which you are tied in the cupboard wearing a gag, tack bra, vibrating but plug and dildo.

This punishment applies concurrently with the first punishment, so for the remainder of this week and all of next. You should time how long you manage to keep the dildo in place.

At each attempt, if your boyfriend considers that you have made a creditable effort, then you are done for the day. On the other hand, if your boyfriend considers that you have regressed or did not make a sufficient effort then you will need to be spanked. He may select whether he spanks your ass, breasts or vulva.

[Nihil]

That bra fitting adventure really was a worthy way to end this crazy month. Thank you again for the wonderful reports. This is one of my favorite GD threads ever, even if it completely lacked tits.*
I am a tiny bit disappointed that my task didn't turn up, but... I guess I'll find another opportunity to tease you, one way or the other. ;-)

*Except for those of my slave, who had more tits in a single sentence than you in several pages of text.

[redcamel]

Originally Posted by Kate92

The third one was 32A, and I put it on. To my horror she muttered, "Cup appears a little too big".

Rolling On The Floor Laughing!!!!!!!!

[BigPhil]

Great reports Kate, thank you for them, although like many others I'm sad that September is over.

Now Stoptober is upon us, which stops you "freely" having orgasms!

Hope you'll write up about the unused tasks and enjoy doing them.

[RockerJ84]

The bra size task was indeed a "fitting" end to your September adventures! Finding out that you don't even properly fill out a 32A bra must have been terrible for you!

Can't wait for your next thread!

Oh, and I just read the new blog you posted about your August vacation diary. Brilliant reading material, as expected!

[Kate92]

Thank you once again everyone for all the kind words about my reports!

It is now the 4th day since my last orgasm and I am already craving for another one! I have made my boyfriend cum twice in the last 12 hours - once last night and once this morning - and that has made my need worse. All your comments aimed at my tits are not helping matters either! And it doesn't look like my boyfriend has any intention of letting me cum anytime soon.

@cl61: Thank you for the punishment, I agree that I deserve it. I really like how you explain the intent behind each task. I will start the punishment from today and will try to keep you updated with my progress from time to time via PM. My boyfriend may not be around every evening, so on days he is not there I won't be able to restrain my hands when I do the wardrobe punishment. I hope that is ok.

@RockerJ84: I am pleased to hear that you noticed my August Vacation Diary blog and that you enjoyed it!

- Kate

[redcamel]

Originally Posted by Kate92

All your comments aimed at my tits are not helping matters either!

Don't be silly: it's not our fault if you have so small tits that no one can avoid to comment them. Just for such an allusion you'd deserve to be dared to apply dark red lipstick at your nipples and areolas and wear only white and light shirts all the time you aren't allowed to wear a bra, just to attract more attention on your chest. But maybe it would be worthless, I'm sure your flatness alone catches the eye more than a DD size...

I hope you're aware that when the salesgirls said "Cup appears a little too big" she actually was thinking "Those tits are definately too small for any size of bra.". Anyway it must be acknowleged her to be very professional: not only she expressed her thoughts in such a kind way, but she also managed not to burst out laughing while you was in the shop.

[cl61]

Originally Posted by Kate92

My boyfriend may not be around every evening, so on days he is not there I won't be able to restrain my hands when I do the wardrobe punishment. I hope that is ok.

That's fine. I hope you've had fun in the first week.