After decades of playing tease and denial, chastity was the next logical step in the journey of sexual misadventure... Found my way here by searching Google for tips, tricks, and relateable experiences. Many common threads with other stories here. We're all the same - but different! BACKSTORY: Some of the milestones or objectives that have led me down this path. 1. Learning how to delay my orgasms to last longer during sex (2002). Pretty basic, but it's what got me into edging. 2. Being introduced to the world of kink by a girl who was into BDSM (2004) So thankful for encountering that naughty little vixen! 3. Learning not to ejaculate during sex (2008) "With tantra you can make an entire session of sex feel like one giant orgasm." - American Pie 2 4. Practicing Karezza (2011) Worshiping a woman's body with my hands and tongue - WITHOUT receiving stimulation of my own genitals. Can stay madly horny four hours doing this! 5. Panty Play (2016) Completely dived into wearing panties full time. Had always been fascinated with ladies' lingerie... Love the feel of the fabric, the colors, and the way it keeps everything confined. It's something that I play with, on and off... Typically in warmer months! 6. Ruining All My Orgasms (2019) Training myself to abandon or ruin every orgasm to keep my energy level high without feeling spent. Normally try to only cum once or twice per month. Personal record is TWO months without ejaculating. 7. Entering Chastity (2022) Did fairly good to start the year... But FOURTEEN "accidents" in June was completely undisciplined... Sure, I can blame those cute bikini girls for looking so scrumptious on the beach... But it's my own lack of self-control that caused me to spill over the edge so many times. It was time to get a chastity cage to curb some of that over zealous wanking...
JUNE 2022 DAY 1: The Program Restarts... A practitioner of orgasm denial and ruined orgasms, I normally keep all my ejaculations to nothing more than an oozing stream or slow dribble - But a new "Ball Spreader" toy had me squiring for distance! Afterwards, the girliest underwear I could force myself to put on was black with white polka dots... And some lace. Added stockings, and bralette for extra discipline. Best quote I've found on the subject: "Immediately after i lose all desire to be dressed in fem" -http://jessicasissyblog.blogspot.com/ DAY 2: Matching Lingerie... Not only do I find matching bras and panties to be incredibly hot on women, I also love having my own sets. A quick look at the lingerie drawer reveals a selection of mostly red and black... Great colors, and relatively "safe". Apparently white is the most common color for a woman's bra - Is this information out-dated? I would have bet that white was the least common color. When John Belushi was peeping into the girls' dormroom in Animal House, it seemed that all the girls had white bras. Cue the same scene in a modern film, and the girls would have brassieres in all the colors of the rainbow - including neon green and flurescent pink! DAY 3: In The Pink... Takes about three to four days after blowing my load before I'm willing to don pink underwear... Have also gravitated to pink right after I've been shaved - Makes the process even more erotic. The cotton panties fit snugly, hugging my package perfectly. Not sure if it was the freshly shaven genitals, the snug cotton fabric, or the fact that the panties were pink... But I started to leak. Luckily, had another pair from the same pack, this time in white. While a condom works to catch the flow of precum during panty play, a boy who wears panties for hours on end may have to resort to pads. DAY 4: VIBED! Tease session with a vibrator through the panties. Should have a full load of cum - But at only the four day mark, I'm definitely not horny enough to squirt with a vibrator tease. A fun, frustrating session because I thought I was getting close a couple of times. Normally, the panties become/get drenched/soaked with precum... But the way my semi-engorged dicklet was bent downwards, it trapped all the fluid inside like a kinked hose... Couldn't believe my panties were perfectly dry afterwards. I felt like such a good girl!
DAY 5: Playing Upstairs... Decided to use clothespegs on the nipples for an after-dinner session. Depending on exactly where the pegs clamp down, it sometimes made me whimper like a girl. Suddenly clamping the same pegs onto the scrotum barely hurts at all. DAY 6: Clear Mind... Diving deeper into exploring my feminine side, my outlook starts to change. Instead of pornographic videos, I often find myself reading sexy stories... Apparently, an orgasm happens in the mind before it happens in the body. DAY 7: Blue Bras & Blue Balls... Picked up a couple new bras - Both blue in color. A blue bra was a perfect match for my aching balls. Figured that 34 inch was my "band size" because that's what the actual measurement is. But a 36 inch is more comfortable for longterm wear. Also noticed a 32 inch on the rack (which is apparently quite rare). I'm just a guy who wears bras for fun during playtime because it keeps me teased... Can't imagine having to put up with wearing one all day, every day! Brassiere discipline can serve as a firm reminder only girls should cum. A good boy can learn to control his cummies, apparently for upwards of 72 - 100 days and beyond. DAY 8: Girls Do It Better... It's "only" been a week without cumming... Could whip it out anytime, and be ejaculating within seconds... Then like a stupid boy, I'd be completely tired and uninspired. I'd rather put on some candles and some music, and slowly tease myself with a vibrator... "...Candles, music... God, girls do everything better!" -That 70s Show DAY 9: You Must Learn Control... The fascinating world of shapewear has also helped keep my excited little wiener from popping up unexpectedly. Another great idea that I got from "Put Him in Panties": "he'll find his genitals squashed against his body... a tight, all encompassing pair of firm control panties makes it very difficult for an erection to go anywhere" -http://brassiered.com/puthiminpanties/panties.html In addition to control briefs, even experimented with a control thong. 90% Polyamide 10% Spandex Took a while to figure out the best placement, but once I found it, damn! That snug little strap spent half the day teasing the hell out of me... I love it!
JULY 2022 DAY 30: Cumming Like a Girl... Learning to ejaculate using a vibrator is a challenge! Had came in panties before - But didn't consider myself to have truly accomplished the feat, because I was using a vibrating cock ring in addition to an external vibrator. The second time was with two external vibrators. While I prefer the feel of silky panties, decided to try cotton for the snugger fit. This kept my unruly member pointing neatly downwards for the duration of the tease. One week without cumming, with a small vibrator stimulating right through my cotton thong.... The sensitive underside of my dicklet was inaccessible. Started vibrating on low, moved to medium, then high. Didn't even realize I was so close to the edge. Had actually stopped "trying" to get there, just started to relax and enjoy it... (sounds like my own advice to a girl) Suddenly felt an impending eruption and stopped the stimulation. Hovered on the edge for several seconds before the release happened. Felt different than accidentally stroking past the point of no return. Pumped out a fair amount of white goo, without feeling "spent" afterwards. If anything, I felt relaxed and energized at the same time. DAY 33: Sissy Shopping Trip... First time out shopping with an actual hooks & straps brassiere... Five hours later, got to experience the relief of taking it off! Was already leaking before I got completely dressed. Stumbled upon "Leak-resistant" panties. 80% Polyamide 20% Spandex Figured they'd be like rubber, but they're surprisingly comfortable. The gusset feels like a built in pad. [Attached Image] DAY 35: Frustration! Wearing shapewear panties over TOP of an already snug pair of silky, lavender-colored panties. Absolutely no chance to become fully erect. [Attached Images] Impossible to tell if I'd been teasing myself with the vibrator for 10 minutes for half an hour... Suddenly, the batteries died. A particularly frustrating way to abruptly end the tease... One drawback of learning how to cum like a girl. DAY 39: The Last Stand... After shaving my bikini area, I tucked my dicklet in for the night. It's especially fun when I haven't worn a specific pair of panties before - So I don't know exactly how they'll hug my genitals. This time, it was to hot pink nylon / spandex. At 4AM, I woke up with my swollen, engorged clitty standing upwards - But still contained inside the panties below the waistband. [Attached Images]
DAY 40: First time in Chastity! Just shy of eight weeks re-entered the world of full-time panty play. Had no idea that I'd be stuffing my dicklet into a metal cock cage. No more flimsy joke shop cages or flexible rubber "tickle cages". The real deal. Solid, unforgiving metal. Regularly playing with silicone and rubber cock rings, I was able to put on the base ring easily. The cage was a different story. My clitty was so excited that it swelled beyond what could fit in the cage. The woman at the store stressed using lots of lube, and I'm glad she did. (have since learned that lube is great for getting the excited cock inside for a teasing session, it's not ideal for longterm use) Once I calmed down enough to get the cage on, I was already oozing copious amounts of precum... With the lubed up aparatus steadily leaking fluid, it was a perfect time to test out the "leak resistant" panties I got last week. There's always room for improvement, and people in the chastity community seem to report trying countless sizes and styles before finding one with the proper fit. FIRST HOUR: Can't believe I've been wearing the cage it for an hour. Should really take a break... But my genitals have already been trained with silicone rings. SECOND HOUR: My first lockup, and I don't want to take the thing off! Still feels great, even after a frustrating vibrator tease session. In addition to having tried cock rings of all sizes, I've enjoyed every minute of licking pussy while wearing my plastic jock cup. This is probably an unfair advantage over anyone who's brand new to male chastity.
DAY 47: First Week of Chastity Training... MONDAY: 5 hours total (2+3) TUESDAY: 7 hours total (4+3) WEDNESDAY: 8 hours total (4+4) THURSDAY: 9 hours total (5+4) FRIDAY: 12 hours total (5+4+3) After eight days of cage training, I was able to spend the night in chastity. Didn't have any arousing dreams (that I'm aware of). Actually spent two nights in a row caged... Although in fairness, I was too tired to really notice. There is something about being clicked shut... I start to drool just like Pavlov's dog. With the "click", I'm now locked for the night and unable to ejaculate... Preserving my no-cumming streak.
DAY 128: Using the Showerhead... Craving a session with hardcore teasing of the testicles... Locked up, balls hanging out of the cage - with a silicone ring around the testes to keep them extra stationary (and vulnerable). Teased them until there was precum everywhere... Then attempted to stroke through the cage. So frustrating - And fun. Cleaning up in the shower, "twisted" the unit around to blast water on the frenulum... Have previously ejaculated like this before - But didn't actually want to this time. Balls get a good pounding from the water as well. DAY 129: Milked in the Cage... Balls were very sore to start the day... Soaked in hot water, as has worked in the past to get blood flowing properly. Caged milking with vibrating wand... Just on the outside of my freshly shaven boy pussy. Intermittently "squeezed" the PC muscle to slowly pump out a fluid that seemed to be half pre-cum, half ejaculate. Once highly aroused and leaking a steady amount of precum, was able to insert a gloved finger with lube and gently massage a few gobs of thicker goo from the prostate - With absolutely no "drop off" or loss of sex buzz afterwards... I've heard this stuff referred to as "prostate fluid". "Officially, the fluid is called prostatic fluid, which is basically ejaculate without the sperm." https://www.healthline.com/health/healthy-sex/prostate-orgasm#what-it-feels-like Bedtime: White nylon hipster panties... With lace.
DAY 130: The Last Orgasm of 2022? Spontaneously released a (ruined) orgasm into a shot glass. Approximately one half ounce of pearly white ejaculate. The orgasm was ruined properly and methodically... No stroking, merely vibrating the head to a few edges, then stuffing the tip into the shot glass. Simply vibrating the glass caused enough stimulation to cause the dribbling to start. Still horny afterwards, but unable to get fully erect... Couldn't get over how brilliantly white the stuff was. Happened upon this article: "Celery is a surprising secret weapon to turning your cum from the usual off-white/vaguely yellow color into that pearly white you want." https://thegrittywoman.com/how-to-cum-more/ Had NEVER heard about this before... But embracing my girly side, have been putting more effort into things like fitness and nutrition... And earlier this year, had introduced celery to my diet!
DAY 137: Support Strap Enjoyed reading the forum thread "Support Strap" https://www.chastitymansion.com/forums/index.php?threads/support-strap.48713/ Some great ideas to help keep the cage in place at night, and even during the day when you're moving around, bending, lifting, etc. All kinds of options available, from homemade solutions to stuff you can order. While I'll be on the lookout for something better, this harness with cock-ring actually fits perfectly around the cage. Even the lock tucks neatly away (if so desired).
Seems that anyone who enjoys chastity play usually has an assortment of cages... Likely a combination of trying different devices to find the best fit - But once a device starts to feel normal on your body, you may forget you're even wearing it. Depending how much one wishes to be teased, the wearer (or owner) may decide that an even smaller cage is needed. Teased the hell out of myself for years by wearing jock cups underneath my clothes. Once I got used to a particular cup, I'd be looking to get another fit or style just so it feels different. [Attached Photo] My genitals get a good teasing while they get accustomed to the new configuration. I'm sure it'll be the same way with the cages...
DAY 139: Another Night in the Cage... Had pretty much been wearing the cage all day - Taking breaks for an hour or two, applying some moisturizing cream to sooth the irritation of the ring. Noticed that the scrotal skin also seems to be getting tougher. Ten days without ejaculating, my balls were heavy and sore - In a good way. Decided to try another night locked in chastity. Most of my pretty panties just don't offer the "support" to keep the cage in place overnight. Have found that the right pantyhose can help keep the cage from flopping a bit. Usually sleep a few hours on my back, plus an hours alternating from side to side - So I'm always going to roll around. Tonight, I opted to wear some less than exciting boyshorts which got me through the night.
DAY 140: Staying Soft... Freshly shaved, re-locked and into pink panties. Tried yoga pants over top, and WOW. Actually distributes the support so there's less movement of the cage. Had to wear them underneath my clothes, because of the obvious protrusion of the lock.
DAY 143: Settling Into The Routine... Spending more nights in the cage, and more hours of the day locked... Was ridiculously frustrated ten days without ejaculating... Have settled a bit, with renewed energy and focus that allows me to get an incredible amount of creative work done. In previous experiences with long term tease and denial, I seem to recall spikes in desire around the 3-4 day mark, 7-10 day mark, 14 days, 21 days, 28 days, 35 days... Basically, getting ridiculously horny and frustrated for a brief period each week... Until I get past that stretch, and can enjoy relatively smooth sailing until the following week. Each threshold is another hurdle to overcome. Chastity Training: Typically unlocking at 4AM, re-locking around 6AM. Considering this used to happen around 1AM, there's definitely some progress. Sleepwear: Black sports bra with hot pink culotte panties. Ridiculously comfortable... DAY 146: Just Another Day... Spent the entire day caged, even forgetting that I was wearing it for a good part of the time. Would have gone to bed with the device - But needed to get an early start on my day, and couldn't afford to sacrifice sleep in favor of continuing the tease & denial game. DAY 156: Caged Morning Wood... Felt good yesterday, and was falling asleep watching TV while still wearing the cage. Decided to go to bed wearing the device and slept without much difficulty. Woke up with a morning boner being deliciously suppressed by the metal bars. It had pulled away from the body creating an "internal erection". Not exactly what I was going for, but it's a step in the right direction. A smaller cage, and snugger panties are in order. Wasn't that uncomfortable - Actually felt kinda good. Still as a precaution, I removed the cage for a couple hours. Still, it's my longest lockup session to date. Chastity Training: Can easily do 16 hours in the cage now. Sleepwear: Snug Cotton Cheetah Print Panties DAY 157: Locked for 24 Consecutive Hours... Woke up with another stifled erection being crushed by the cage... Yesterday morning, I briefly removed the cage as a precaution. This morning, the attempted erection went away on its own, so the cage remained on. Outside for morning exercise, getting used to the feeling of running around with the cage between my legs. Support is a must. Passed my first full 24 hours caged without even realizing it... That's nothing for chastity veterans, but I'm still getting over that hurdle - With no rush or pressure, just having fun exploring at my own pace. Chastity Training: Endured approximately 46 hours locked within a 48 hour period. Underwear: Pink Push-up Bra & Bikini Panties DAY 158: Freebird... Spending a few days out of the cage as a precaution. Scrotal skin getting nice and strong, but suddenly experiencing some slight irritation where the base of my member meets the scrotum. It's not raw or sore this morning, but there are still a couple of marks on the underside. Better to miss days of training than to do more damage and be out of the game for weeks. Even my favorite silicone rings have left marks from time to time, especially if they managed to shift while I was asleep. Decided to "lock" myself in a bra instead. Spontaneously pulled out a "convertable strapless push-up bra". Have tried it on, but haven't worn it for hours on end. It came with straps attached, but felt brave enough to remove them (unsure of how difficult they'll be to re-attach) but the fit is perfect and it feels great. Was starting to bother after a couple hours - But a few hours later, barely noticed.
DAY 160: Nude is the New Black... After a quick break from the cage, locked back up this morning. After a morning edging session, immediately shrunk myself back to size under the cold water until soft enough to stuff it back inside the cage. Freezing a sexual high is lots of fun. Everything's still buzzing but numb at the same time. The cage continues to cradle and corral the excited member. Love my black thing-high stockings... Sold out of black, only color available was "nude". My neurotic obsession led me to put on control panties of matching color - But not before slipping on a tiny thong/g-string (that I'd normally wear in the summertime). Neither garment holds the cage in place on its' own... But pairing these two together has kept the cage exactly where it should be. [attached image] Might even be able to sleep this way... DAY 161: Caged in a Lacy Thong... Enjoy wearing a bra and panties when I'm shopping for new underwear... Wore a strapless red push-up bra with cheeky nylon panties. [attached image] Picked up a pair of lacy thong panties, not expecting them to support the cage... But they were so adorable and girly that I couldn't resist. [attached image] Ideally, panties should contain pink, and some lace along with a bow... Tried them on in the afternoon just for fun... Much to my surprise, the thong held the cage perfectly in place - For the entire day, AND through the night. Being locked in panties like these is like spending consecutive hours inside a tight pussy... My only regret is not purchasing another pair! Woke up with an attempted erection - Except this time, it was properly restricted, held in place by the cage, WITHOUT the "internal erection" that normally happens. Is my body being trained? Did that dainty little thong do the trick? Before chastity, the morning wood could be anywhere from "half chub" to "raging hard-on". DAY 162: Realistic Orgasm Denial Goals... Over 60 ruined orgasms in 2022... Spilled over the edge more than 40 times before getting the cage... Second half of the year (with the cage) was able to cut the number of ejaculations in half. At first, I thought "this is great!". I can rub outside the cage until I'm tired of stroking, and still be unable to climax. Took me 20 days before I accidentally spilled my load inside the cage. While edging in the cage, still learning the point of no return... Uncaged, I can stop all stimulation and avoid spilling over. In chastity, the edging session suddenly "sneaks" into orgasmic territory, and the cage actually squeezes it into triggering a release. (Gotta remember to do those Kegel excercises!) I now prefer to run water over my genitals... The cage keeps everything in place for teasing, and I can lie on my back, legs in the air, squirming & frustrated like a girl on the edge of an orgasm but just can't climax. Of course if I wanted to, I could easily blast pressurized water on the frenulum and I'd be squirting uncontrollably with my toes curled. DAY 163: The Longest Lockup... Woke up with just a partial erection in the cage. The girly boybriefs I wore last night didn't offer nearly as much support as the thong (from the night before). Still reminding myself that it's my longest lockup session to date... (Probably shouldn't have done that vibrator tease this morning) Balls feel heavy and engorged, but they don't seem quite as large as they'd normally be after weeks of tease and denial. Another lacy new thong for my collection, tried it on just for fun this morning and find myself still wearing it. [attached image]
Are you really behind here or have you got your days mixed up? If you started in June you should be close to 200 days by now.
Everyone's on a different journey - But I see what may have caused the confusion. "Day 1" was my return to full-time orgasm denial. Didn't get the cage until "Day 40" . Should double check my notes just to be sure, in the name of science.
Good catch! Did the math and it's actually closer to "Day 199". Managed to lose a month in there somewhere...
If you locked up on 19th June it will be 199 days today. I only know this as I started 24/7 chastity with my wife on the 20th June and my countdown app tells me the number of days.