My wife/Mistress and I have dabbled in chastity, off and on for about the last 2 years. The longest I've gone locked is about 10 days. At the end of August, she asked me if I was prepared to do Locktober and be locked for 31 days. We decided to give it a go and spend September preparing for it since it would obviously be a significant step up from what we've done. One of the ways we're prepping is by doing a 10-day ruined orgasm challenge. There are a lot of these if you Google that, but we took this one - http://www.keephimcaged.com/the-ruined- ... challenge/ - and have made some tweaks
1. She always cums first
2. When the ruin is complete, she very slowly (no accidents!) will stroke to make sure everything dribbles and drips out, and we get every last drop
3. I must eat all pre-cum and cum
So, with those rules, we started last night. We are not going in the order they have them in the post, because some of the challenges take a longer time to do.
Last night, after getting her off, I was allowed PIV and to ruin on her thigh. Sexually serving her and giving her orgasms always makes be very aroused, so it didn't take long . I then dutifully bent down and licked my spunk from her thigh. She then did the slow stroke, collecting what was left in her hand so I could lick that up as well.
She asked me later if it was frustrating, knowing she was getting full pleasure and I was being ruined - and knowing going in that I was only going to get a ruined orgasm...and there were 9 more to come. I told her it wasn't frustration exactly. Tempered by feeling very submissive, and knowing she was getting pleasure made be very sexually aroused and horny. Instead of frustration, I told her it felt more like feeling unfulfilled.
So, we continue tonight. I'm not sure which of the challenges we're doing, but I'll report back tomorrow.
Damn. I was straining in the cage just reading those. I haven't been out since July 10, just the thought of being out and touched even if it ends in a ruin...
04/07/19 "And then I 'punished' you by making you lick my pussy after I let my other 'boy' fuck me." --Mrs. Twisted
1: She only cums !!!
2: Refer to 1
3: Refer to 1 etc etc etc
Oh and that’s EVERY month of EVERY year !! Really leads to a very simple system ... MsM says so !!
MsM’s ld
New Zealand
Still having difficulty getting back into 24/7/365 chastity since covid. Very tender old man skin under the scrotum damages easily. Trying an HT Mk5 nub now. Love the fact you can’t pull out of it, hope my skin toughens up.
It' been a busy weekend. We've been doing a lot of home reno projects since Covid has kept us in the house, so I didn't have a chance to post Thursday, Friday and Saturday's adventures....
Thursday, Mistress decided to go with this challenge - She must edge you with a blowjob. When you start to cum she will let your cock out of her mouth and just watch you squirt.
Now, full disclosure. 1) She has excellent oral skills; and 2) she loves giving teasing blow jobs. She was having some pain from our first reno round, so she told me rule 1 - She always cums first - was waived for the evening, but that she'd "make it up to me" later, The she had me stand naked before her as she sat in her high backed arm chair - her throne, if you will. She quickly engulfed me in her mouth, as she loves the feeling of me getting hard from her ministrations. I lasted longer than the night before, bit she also made sure to be teasing and bring me to many edges. Finally, she felt my cock swell, pulled her mouth away and I just dribbled out - into her open mouth. She then gave me a wonderful snowball kiss to end the evening.
Friday night started off with me orally worshiping her for over an hour. She certainly made it up to me! She had a number of orgasms, all while my cock throbbed painfully in my cage. Satiated, she told me to roll over on my back and removed my cage. Then she grinned down at me. "jerk off for me, slut," she ordered. She then guided my masturbation, having me start of very, very slow and soft, speeding up over a five minute period until my first edge. She then gave more instructions - faster, slower, harder or softer, just the shaft, just the head - until I'd had five edges and she told me I had permission to ruin my orgasm. I abandoned it just as I hit the point of no return, and she expertly caught it all in the palm of her hand and fed me every last drop.
Saturday she told me - You must have 3 ruined orgasms in one hour with her help. If you fail, the task won’t be completed… as we began our day, just to leave me anticipating it throughout the day. As it wore on however, and things with the reno weren't progressing as fast as we expected, she let me know we might have to substitute that challenge for another one. We got into bed, and she began rubbing and stroking me, and after about 15 minutes and a number of edges, Iw as squirming and begging her to stop. She gave three more strokes and...RUINED! She let me rest for a minute or so, then started again, and within another 2 - 3 minutes, the second ruin. She let it dribble out before she started again and gave me the third ruin, remarking "Well, that didn't take an hour, as she swung her legs over both side of my head and Queened me to a satisfying orgasm.
This morning started out with an edge before we even got out of bed. We watched the early and late football games, and she edged me for every score, so I'd say tonight will be - You will be edged five times during the day, starting in bed in the morning, and then only ruined last thing at night in the manner of her choosing.. It's been more than 5 edges, but as she pointed out, she thinks it says "A minimum of 5 times." She also said I know she's not exactly a rule follower and likes to tweak things to her liking. So, tonight's challenge might be the above, or somethign totally different because she just likes edging me!
Anyway, for my part, this is going well. Getting a BJ from her is a treat, even if the orgasm was ruined. I know how much she loves guiding my masturbation, so that made me feel extra submissive and slutty. And wierdly enough, having 3 ruined orgasms actually was oddly satisfying in some way. I think it was because after the first one, my edges and the depth - for lack of a better word - of the feeling before getting to the point of no return were deeper and more intense.
So, as I mentioned yesterday, Mistress chose - You will be edged five times during the day, starting in bed in the morning, and then only ruined last thing at night in the manner of her choosing., but of course, she decided 5 was not enough . She started the morning edging me once before we got out of bed, and 2 more time before noon. Then, her imagination took over, and she decided while we watched the opening weekend of football, she would edge me for each score. By the end of the Patriots game, we were at 8...then came Saints-Bucs. That was 10 more edges, or 18. She edged me twice more before we headed to bed, "just to make it an even 20," she said.
Of course, after her orgasm, she decided we should do the 5 originally called for in the challenge. Not a high - we've done many, many more in one session - but it certainly left me hard, hot and horny. So much so that after the fifth edge I begged her - not to cum, but to ruin me - which she expertly did, leaving me right on the edge, and moments later, my cock, without stimulation or touch, bobbing, pulsing and leaking a slow stream of jizz.
At this point, we're 5 days - soon to be six - into this, and I have no idea what's planned for tonight, and I'm constantly aroused and needing her. I can only imagine what 31 days of being teased without even the relief of a ruined orgasm is going to bring.
So, last night was...not what I expected. Mistress chose - Have a ruined orgasm after being teased and denied for at least 2 hours. Try to shoot the cum into your mouth for fun…
My thought was that she would tease me for 2 hours, but that wasn't her plan. Instead, she sent me off to my home office with a list of Literotica stories to read and porn to watch. I was to slowly stroke while reading and watching. After each edge, I was to fondle and squeeze my balls for a minute,while licking up any pre-cum, before going back to slow stroking. This took about 90 minutes, during which I edged... I don't know. I lost count.
When i was done, we adjourned to the bedroom, and she took over the teasing. We have an adjustable bed, so she raised the head as far as it would go, and had me lie in a position that had me with me legs up in the air, cock pointed at my face. She then quickly built me to and edge - which she kept right on the precipice of for a long while, asking my which story or video turned me on the most, telling my how I was her slut and it was going to be a fun Locktober. Then, with three hard, fast strokes, I dribbled out. Since it was a dribble, it didn't make it to my mouth, but she took care of that, by scooping up all of it and feeding it to me.
She then mentioned how wet she was, and that she had waived the cumming first rule because she wanted the 2 hours of teasing without delay. I then was allowed to use her favorite dildo on her to bring her to three orgasms.
The 90 minutes of teasing myself was maddening. So many times I had to hold back. The edge riding was even worse, and that position was something new, and I'm sure something she'll use in the future when I'm allowed a full, explosive orgasm.
My wife just caught me masterbating while she was home on her holidays (she unlocked me for the week) and gave me a nine day lock up as punishment and then went on to say that we WILL be doing Locktober ... that means no release until at least November. She wasn’t happy and said “Maybe next time you’ll think first”.
I’ve been noticing her change and become a lot more “in charge” with our marriage lately.... turns me on. It’s going to be a long time before I get to cum again.
We've been trying out a new micro-chastity cage with a view to Locktober this year. I've done three days in it but suffering from the settling-in discomforts that seem to come with new devices, though the difference in length from my old favourite is only 1.5cm (3cm cage, 4.5cm total vs 4.5cm cage and 6cm total length).
Her plan next month is to unlock me for precisely as long as She requires me, then swap cages until Her next demand.
The purist in me has an issue with not being 24/7, but I'm not the one in charge.
. I then dutifully bent down and licked my spunk from her thigh. She then did the slow stroke, collecting what was left in her hand so I could lick that up as well.
. She started the morning edging me once before we got out of bed, and 2 more time before noon. Then, her imagination took over, and she decided while we watched the opening weekend of football, she would edge me for each score. By the end of the Patriots game, we were at 8...then came Saints-Bucs. That was 10 more edges, or 18. She edged me twice more before we headed to bed, "just to make it an even 20," she said. 