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Intro

This week I have decided to challenge myself a little. Well, a little more actually. I had already spent time in chastity: a few weeks, maybe even a month but it was just that… chastity as in absolutely no touching. Oh don’t get me wrong, chastity by itself can be a challenge, especially when I’m bored but this time I decided to take the challenge to the next level: I will stroke and edge every day of this week – restraining from cumming of course – until Sunday when I get my sweet release. I’ll post reports daily so stay tuned.
I made a faproulette to support me through this time, I’ll just ignore the cumming instructions and replace them by cumming on the second Sunday.
Link to the roulette for reference : https://www.faproulette.co/35691/endurance-check/

Day 1 – Sunday
I start the challenge with quite an unlucky roll: 6-5-2 which means 1 hour of stroking (no edging allowed) followed by 10 edges then 15 minutes of stroking at bedtime and 15 more first thing in the morning. So for my stroking I went to chaturbate, scrolled trough a few categories and ended up finding this very cute trans (Asianqt19 if you want to look her up) who was having quite a show, stroking with one hand and playing with her perky tits with the other. When I was about 50 minutes in my fapping session she started begging to cum, so I could relate a lot since I was also so horny. I ended my 60 minutes of stroking and carried on with my 10 edges. I like to edge fast, and believe me after 60 minutes of non-stop stroking it was quite fast, I had my 10 edges in less than 10 minutes, pushing myself closer every time but still careful not to go over. The first tree edges were quite easy but the next ones were a lot more challenging, the feeling was different, I was so sensitive it was a mixture of pleasure, pain and frustration. On the chaturbate my stimulation was actually adding to the challenge since she was begging and moaning more than ever, and I’m very receptive to those sounds. Anyway, I finished my edges before she could actually cum, so I don’t know if she finally could orgasm or not… I hope for her that she could, she was so cute. On my side, I let myself go limp and put my clothes back on, frustrated and happy at the same time – oh this is going to be a fun week. A few hours later, it was bedtime, I took up my phone and loaded some BBC videos and did my 15 minutes stroking. Once done I immediately put on my shorts (they’e designed so that when they’re on I can’t touch myself), and I found a 15 minutes videos for the next morning.

Day 2 – Monday
When I woke up today, I unlocked my shorts and immediately went for my phone and started stroking. Usually when I stroke as soon as wake-up, it’s for a quick cum not holding anything back, so having to go 15 minutes was a bit unusual but after the first 5 minutes were over the remaining 10 were actually OK. The thing is… well, it did its job turning me on so early in the day. I couldn’t stop thinking about anything other than stroking all morning. So much so that I decided to make today’s session at noon.
The session was a bit lighter: I rolled 4-1-4 so “only” 30 minutes of stroking and 2 edges with an additional 10 minutes of stroking every hour. I completed the initial stroking with a video of a blowjob/throatfuck compilation. The last minutes (maybe 10, maybe less) were a bit challenging since there were a lot of orgasms and cum dripping from those beautiful mouths. After that, I did my edges to a similar, but shorter video. For the additional stroking, I decided to les fate decide the video, using the random function on a famous porn tube and selecting the first 10min video, the first one was a video of pegging, which is something I’d really like to try sometimes. An hour later, the second video featured a FFM threesome with a huge squirting at the end, it was hard for me to keep control and stay away from the edge. Third video was a promo for a gangbang video: 100 on 1, again there was a lot of cumming and once again I had to channel all my will to stop myself to get to the edge or even over the edge… It’s over for today but I’m horny as hell, I kind of want to keep watching porn but I know it will just make it harder not to touch myself.

Day 3 – Tuesday
This morning I went shopping, and I was surprised to notice how turned on I was by the summer outfits… panties peeking from under a miniskirt, the shape of a perfect butt barely contained by tiny shorts, very low-cut necklines; I love summer. Anyway I came back out quite horny and started my session right away. Twenty minutes of stroking, OK that’s a time I am comfortable with. Then come the edges, 7 edges this time. The first one is incredibly difficult to pull away from since I was sooo ready to burst, but I foster all my will, remember what’s at stake and stop just in time. The next ones are a bit more easy since I’m now in the right mindset although the very last one was also quite challenging. I’m thinking “I made it so far, don’t I deserve a reward?” but that though only went flashing through my head and I refrain myself. Time for the last roll… SIX well, if I were playing with the normal rules, I’d be able to orgasm now. But I’m challenging myself to a week so I’d take the other option and reroll for stroking and edging, I hope it’s going to be easy. So back to stroking, I still have the feeling of those 7 edges lingering around, hopefully I only have to do 5 minutes this time and I know I can do that. I’m done with the stroking now time to discover my fate for the edges. And I get to do 5, it could have been better but I guess it could also have been worse (max you can have is 20 edges and I shiver at the thought of that many edges in a row). These edges come and go so fast and now they are only frustration, the usual hint of pleasure has totally vanished and I have to power through each one, precum is flowing now more than ever and I’m just happy to be done for the day.

Hi,

That sounds interesting. Keep us updated please

As you might have guessed by the lack of update, things went wrong on Wednesday (day 4), I started having red/pink traces in my precum so I obviously freaked out and reached for medical attention. Fortunately I have a friend who is a doctor and knows about my kinks (we share a few of them). After I explained my self-imposed challenge, she told me it was probably the excessive stimulation that led to minor breaks in blood vessels. She took samples anyway and a few days later results came and there was no infection, what a relief.

This week, I finally put myself to another challenge but to avoid any problem like last time, I’ll be more progressive in my challenge : I will start with something very simple and every day, I’ll add a little extra.

So I started on Sunday again, and from now on until my release next Sunday, the only underwear that I’ll be wearing will be female underwear. I know that’s not much of a challenge but I’ll be adding more over the next days…

Monday, I’m wearing my panties (cute grey and pink stripes panties), there will potentially be an awkward moment later on when I’m at the gym, changing clothes but it turns out I was quite lucky since the locker room was completely empty when I changed, so no awkward moment when somebody might have noticed me. The new challenge will be to wear a buttplug for 3 hours each day from now on, that’s a bit longer than what I usually do, but it’s not the longest I have worn it (longest is 6 hours). For today, I’ve chosen a medium sized metallic plug with which I’m quite comfortable. I can feel it inside by ass but there is no discomfort.

Tuesday, I’m wearing navy panties with little red hearts all over them. I had quite a long day at work, so I’m home a bit later than usual, which means that my plugged time will extend until bedtime. I’m wearing the same plug as yesterday and it feels very comfortable, maybe I’ll keep it for the night, I’ll decide on the moment. Today’s additional kink is wearing nipple clamps for 15 minutes. I love the sting of nipple clamps biting my skin. For today’s clamping I’ll use clover clamps and I’ll do that just before bedtime. Oh so I ended up torturing my nipples, clamping them with more and more cruel clamps, pulling, twisting, really abusing myself. By the end, after more than one hour of torture, my nipples were raw and red. I took my buttplug out and went to sleep.

Wednesday, this is the point where it broke last time. As I didn’t masturbate at all since Sunday, I don’t feel the same urge as last time but it’s definitely starting to tingle... My panties today are silk, red with white polka dots, thee grisliest I’ve worn this week. I was back from work quite early and decided to wear my large buttplug today, definitely less comfortable than the medium one I’ve used the previous days. After removing the plug, I went on with the additional kink for today : spanking ! A few years ago, I designed a tool to “calculate” the spanking I deserved, accounting for every action I feel I should be punished for (cursing, not doing chores, etc…), and I’ll use it daily for the remaining of the week. I ended up giving myself 24 hits of the cane… ouch Now to be honest, I’ve delayed my nipple clamping because I’m still sore and sensitive from yesterday’s session but I can’t put it off any longer. Like I suspected, those 15 minutes hurt like hell, but I went through it and now, I can wait until tomorrow.