The Punishment

I’m on day 4 of 125 days of orgasm denial today. Yesterday my boyfriend and I finally had time to call, which was really great. A few days ago I touched myself without permission, so we decided that we would do my punishment. We decided on edging and spanking.

He rolled a d12 to see how many times I would have to edge myself, and he got an 8. We ended up using my vibrator, and I had to keep it on the lowest setting whilst grinding against it and touching my chest and ribs. I got sooo wet from it but it took me forever to get to the edge. After I edged he had me spank myself 10 times with a belt, 5 on each butt cheek. I’m such a perfectionist when it comes to spanking that I spanked myself more than 10 times, though.

After the second edge I also forgot to say please and ask permission to touch my pussy to see how wet I was so we increased the amount of spanks to 20 (He initially wanted to do 15 but 20 is easier to divide by 2). He also had me ask permission to touch my chest and ribs from then on, and I told him that I enjoy being reminded to use my manners so we made a thing of having me say please and thank you.

I also lost count after like the third edge so my boyfriend had me reset the counter back to 0! From then on I kept track using our chat, but he told me that the next time I wouldn’t be allowed to write the numbers down. We also had to stop the spanking because it was too loud, and I got questioned on what the noise was by someone I live with. The next time I’m alone in the house I have to spank myself 120 times (The amount I missed out on during our session)

After my fourth or fifth edge my boyfriend had me suck a dildo whilst edging, which made me reach the edge pretty fast. I was so wet after, too. He then had me fuck myself with it, and it slid in so easily. He told me to fuck myself hard and I did and it felt so overstimulating (but like in a good way), and he did something that really got me. Since I forgot to thank him he asked me “What, no thank you?” (Paraphrased), which was so hot, so I thanked him multiple times. I swear he got me so noisy.

I did ask him if I could slow down and have a little break and he let me. Unfortunately as soon as I stopped I got really overwhelmed/sad out of nowhere and I started crying. It’s something I’ve struggled with before when we’ve done stuff relating to penetration, and I think it has to do with my sexual trauma that I’m still trying to figure out and work through. We ended up stopping, and he was so supportive and loving.

We just ended up chatting regularly and chilling on call for a while after that. I’m so happy that I have someone who loves and respects me so much to be honest. I feel really safe and comfortable with him, and I’m glad that we have that foundation of trust and that we’re able to say no to each other/pick up on the other’s discomfort if something is wrong.

We’re going to have free time on the weekend so we’ll probably continue with the punishment then, and try to avoid anything that might trigger me/do stuff very differently.

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u/KeepMeFromDreaming — 23 hours ago
▲ 4 r/u_KeepMeFromDreaming+1 crossposts

I miss my Boyfriend

He’s not gone, he’s just busy right now, but I miss him so much. I’m so horny, too, and I can’t even touch myself because I need his permission and that’s making me even hornier. I want him so badly; I want to touch his skin, kiss his face and his shoulders, and his chest, and his ribs, and his sides, and his stomach, and his thighs. I want to be alllll over him. I want to mark him up and I want him to mark me up. I want him to fuck me and edge me and eat me out and finger me. I just want him so badly.

I’m in such a submissive mood right now, I want to do anything he asks of me. Earlier we were talking about someone fucking someone with a dildo and then making them deep throat it, and I want to do that for him so badly. I want to fuck myself and then clean it all up with my mouth. I’m so needy for him.

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u/KeepMeFromDreaming — 2 days ago

I Think I’m Conditioned

Something both amazing and terrible happened earlier today. I’m not allowed to touch myself without my boyfriend’s permission, but today I disobeyed and tried to. I started to touch myself and then ended up using my vibrator, but no matter what I did I wasn’t able to even slightly feel good. It just felt like nothing. I don’t know if it’s because of the guilt, or because I’m so used to needing permission, but oh my god.

I already told my boyfriend and he said it was hot, but that he’s still going to punish me. I’m dreading to find out what he’ll come up with. This is also the first day of my 125 day denial!

Edit: Because I apparently have to specify, I was being light-hearted and playfully resistant when I said “I’m dreading to find out what he’ll come up with”. I LOVE my boyfriend, and like all of what we do together is my idea. He’s way less into kink than I am, and doesn’t place any expectations on me! I can back out of anything at any time. Majority of what I write on this account doesn’t go into depth about the conversations that he and I have about consent and what we’re both comfortable with. He would never force me to do something that I’m not comfortable with.

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u/KeepMeFromDreaming — 5 days ago

I got to Edge and Ruin Today - Denial Journal

My poll to see how long I should be denied for recently closed, and it came out to 126 (we’re actually doing 125 because it’s a nicer number) days. Which, it’s a long time to stay denied, especially since the longest I’ve gone is only 16 days, but I’m going to try.

Anyway, my boyfriend allowed me to edge today and said I could ruin, so I did. I ended up using my dolce since I’ve been getting used to it recently and it felt so good. I’m kind of getting addicted to it, to be honest. It’s just nice to be able to push it in (with permission of course) and turn it on and just do other stuff whilst I edge. I got so wet whilst using it earlier, too; I was practically dripping all over my sheets.

I was going to do an audio recording of me fucking myself and moaning for my boyfriend tonight, but for whatever reason I just wasn’t getting anywhere with it. I guess I also got a bit nervous so I didn’t do it, but I may do it the day after tomorrow. I love doing a good job and being all slutty for him. That’s really all I want, to please him.

Lastly, I ended up spanking myself with one of my belts for a bit. I spanked my thighs, my butt, and my pussy. I honestly love the feeling of the leather coming in contact with my sensitive, soft skin, but it’s hard to go as hard as I want, and I want to go very hard. I wasn’t even able to leave any red marks on my butt, which is pretty disappointing. I guess I’ll have to work on it!

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u/KeepMeFromDreaming — 8 days ago

118 Days and Counting Until I’m Allowed to cum

Sort of a repost since I feel like my previous title didn’t really match with my intent and was accidentally click-baity (It made it seem like I already did 120 days of denial, which I haven’t yet). So we recently put up a poll (still open) to determine when I would be allowed to cum next, and the turn out was way more than I expected. 118 people voted for the ‘+1 day’ option, meaning that I’m going to be denied for 118 days. Which is nearly 4 months!

We’re still figuring out how exactly we’re going to go about this, since I DO need maintenance orgasms every once in a while, and I’m not really that experienced with long term denial. My boyfriend also thinks that it’s a long time to go without cumming, which it is. In all likelihood we’re probably going to go through with it but with the caveat of me being able to ruin every once in a while. I’ll also be able to back-out at any time if I need to and cum, but I do want to try to see how far I can come. Does anyone have any advice or ideas on how to deal with longer term denial? The most I’ve gone is 16 days, to be honest.

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u/KeepMeFromDreaming — 11 days ago

Finally Figured out how to use my Dolce

I got permission to touch myself last night so I decided to mess around with my dolce a little bit. The first time we used it, it didn’t go well. It was a little uncomfortable and too intense, but we decided to work on it. I always had trouble with vibration inside my pussy, but I’m getting a little more used to it.

I edged a little bit and got myself wet before trying to put it in, which I think really helped; when we initially tried it out we kind of rushed into it. I do struggle to get wet often times and mentally ‘turned on’, so even just getting into the mood is a battle sometimes. Having a super supportive boyfriend, edging, and orgasm denial has really helped me in that regard, though.

Anyway, I settled onto my stomach and slowly pushed the thicker end in and got the thin part situated on my clit. It doesn’t entirely fit my external anatomy, so I had to make do. Playing around with it on lower settings for a little while did feel really good.

So I eventually ended up tying my hands together with a belt (pretty easy to get out of), setting a timer, and raising my hips and ass off the bed and into the air so that I would be a bit more exposed. Even if no one is actually there to watch me, it turns me on that I’m in such a slutty position. I also like to imagine my boyfriend being able to see me when I edge and fuck myself for him.

I let it buzz on for a little while, feeling the wetness seep out from my pussy and around the dolce; there was unfortunately no dripping, but maybe next time. I did manage to edge a couple times, and it felt pretty good once I got fully used to it. I didn’t cum though, because I never got permission to! I told my boyfriend about it later on, and what I had found out about my preferred settings and speed. I didn’t get into specifics of what I had done, though, since I decided to save it for my ‘online journal’ entry.

I’d love for him to eventually edge me, and maybe make me cum and overstimulate me with our new toy. I hate being long distance, it would just be so much easier if he and I could be in the same state.

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u/KeepMeFromDreaming — 12 days ago

Poll to Determine When I’ll be Allowed to cum Next

We had the idea of making a fun little poll to see how long I would be denied! Whichever category wins is the one I have to complete before being allowed to cum…

View Poll

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u/KeepMeFromDreaming — 13 days ago

I Finally Orgasmed After 16 Days but it was Kind of Unsatisfying

So for anyone who hasn’t seen my posts yet, I’m the wordle denial guy. My boyfriend and I have been messing around with orgasm control and denial for the past month and a half, and it’s been great so far. I was going for a week of denial, but I ended up cumming without permission and he didn’t have time to punish me so that week turned into more than a week.

Anyway, we recently got a lovense dolce to use for long distance play (we live on opposite ends of the country), and having him control the vibrator whilst I used it was pretty hot, but there was one issue; it just didn’t fit my anatomy properly. Which made the whole experience less than ideal. That said, he did make me cum, but it wasn’t that great. It felt more like a ruin. I kind of expected more after 16 days of orgasm denial and (mostly) no touch.

Maybe it’s because we’re both inexperienced, and we were using it wrong? I don’t know. The whole thing makes me think though, maybe I prefer edging and denial over actual orgasms at this point. Maybe I should see if I could get to 3 weeks and then a month without cumming? I’d still like to have maintenance orgasms once in a while because if I don’t have them it kind of messes with my head and brain chemistry (I’m schizophrenic), but I just don’t know.

I’ll ask my boyfriend if I can play around with the dolce on my own to sort of see if I can figure out what works for me and what doesn’t, or he and I could play around with it together more. It would just be a shame if we didn’t find a way to make it work because it was supposed to be a way for us to connect intimately despite the distance, and because I did spend a lot of money on it. We also had the goal of doing something with forced orgasms/overstimulation with it. I guess it’s time for some trial and error…

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u/KeepMeFromDreaming — 15 days ago

About to Get Edged Like Crazy, Hell Yeah

I can’t wait oh my god… my dolce finally came in so my boyfriend can finally edge and torture me. I’m getting wet just thinking about it to be honest. I’m also kind of scared, because he still needs to punish me for cumming without permission, and he’s mentioned the idea of overstimulation a few times.

u/KeepMeFromDreaming — 25 days ago

Final Day of Week Long Orgasm Denial + Wordle Orgasm Denial Guy Update (Repost)

I’m on my final day of my one week orgasm denial (Unless my boyfriend decides to extend it), and I’m so excited. Things are so good right now, I can reach the edge in under 3 minutes when using my vibrator and I almost orgasmed from fucking myself earlier. My words may be dry, but my pussy is indeed wet.

Today I was allowed to not only use my vibrator for 3 minutes, but I was also allowed to fuck myself using my big tentacle dildo. I can only fit half of it but it felt so good. I usually have trouble feeling pleasure from penetration, but every time my boyfriend has had me fuck myself has felt so good.

I was only allowed to use it for 10 minutes, but those 10 minutes were immaculate. There’s something about fucking myself whilst completely ignoring my clit that makes me so wet and needy. I was really going at it, roughly fucking my pussy with a dildo that I knew was too thick to fully fit inside me, trying to force it deeper, and moaning and begging aloud for it to be faster and harder. I’ve gotten in the habit of purposefully trying to be noisy for my boyfriend even if he can’t hear me because he’s on the other side of the country.

After I finished fucking myself, he let me hump my pillow for another 10 minutes, which didn’t stimulate me much but it was so hot conceptually that I really made a mess. I really hope he lets me cum tomorrow, but I have the sneaking suspicion that he won’t because of my previous transgressions. We’re also waiting on a lovense dolce for long distance play so that may also be a factor… It’s going to be so hard to not cum without permission!

Repost because I wanted to add some stuff and because I wanted to use a more appropriate flair for this post!

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u/KeepMeFromDreaming — 26 days ago

Final day of denial + wordle guy update

I’m on my final day of my one week orgasm denial (Unless my boyfriend decides to extend it), and I’m so excited. Things are so good right now, I can reach the edge in under 3 minutes when using my vibrator and I almost orgasmed from fucking myself earlier. My words may be dry, but my pussy is indeed wet.

Today I was allowed to not only use my vibrator for 3 minutes, but I was also allowed to fuck myself using my big tentacle dildo. I can only fit half of it but it felt so good. I usually have trouble feeling pleasure from penetration, but every time my boyfriend has had me fuck myself has felt so good.

I was only allowed to use it for 10 minutes, but those 10 minutes were immaculate. There’s something about fucking myself whilst completely ignoring my clit that makes me so wet and needy. I was really going at it, roughly fucking my pussy with a dildo that I knew was too thick to fully fit inside me, trying to force it deeper, and moaning and begging aloud for it to be faster and harder. I’ve gotten in the habit of purposefully trying to be noisy for my boyfriend even if he can’t hear me because he’s on the other side of the country.

After I finished fucking myself, he let me hump my pillow for another 10 minutes, which didn’t stimulate me much but it was so hot conceptually that I really made a mess. I really hope he lets me cum tomorrow, but I have the sneaking suspicion that he won’t because of my previous transgressions. We’re also waiting on a lovense dolce for long distance play so that may also be a factor… It’s going to be so hard to not cum without permission!

u/KeepMeFromDreaming — 26 days ago

Almost 4 days (mostly) no touch + punishment

Wordle guy here again… So since my last post my boyfriend allowed me to touch myself, and I accidentally came. I got to the edge and it just felt too good after not properly cumming for like 5-ish days, so I just held my vibrator against my clit and had probably one of the longest most drawn out orgasms I’ve ever had, and I just couldn’t stop. So, now I’m due for punishment.

That said, we haven’t really had the time for my boyfriend to punish me since I came, so I’m coming up on my 4rth day since cumming. For most of these days I was on no touch, I wasn’t even allowed to hump anything (which I’m usually allowed to do without asking).

However, yesterday he allowed me to use a vibrator twice and touch myself with my fingers once, each time in 3 minute intervals (15-20 minute cooldown, we were watching something). It was a reward for finding sources on early Imperial Roman armor for him (We’re both artists and he needed them for a drawing. I’m also going into archeological anthropology with a focus on Imperial Rome). Anyway, it was so good I almost ended up coming the second time he let me use the vibrator, I had to actively stop myself!

Today he’s even letting me touch myself again for another 3 minutes for helping him with something else! My boyfriend is so good to me to be honest, even after I came without permission. I’m scared for what my punishment will be though, he hasn’t really told me much about what he’s planning to do or given me any hints. I’m also antsy because I HAVE asked him to be meaner to me in the past.

This whole thing has gotten me so needy recently, though.

u/KeepMeFromDreaming — 29 days ago

I Didn’t Think I’d be Back so Soon + High + 3 Days of Denial

Wordle guy here. I’m officially on day 3 of my week long orgasm denial (technically day 4 orgasm free, but I ruined on day 1 so we reset the timer) of my orgasm denial, and my boyfriend FINALLY Allowed me to touch myself today (twice) after I begged him. I’m so happy and needy, but so far I’ve managed to not ruin or cum because I’m very good, but it’s been hard. Even without touching, I’ve been getting wet and desperate so easily recently!

So anyway, I had two THC drinks with the hope of relaxing a little, and it’s worked okay. I’m all hazy and needy and wet, but unfortunately my boyfriend can’t text me right now, which is so frustrating. Earlier he was telling me about an idea he has for a punishment if I ended up cumming: If I cum, I have to cum as many times in a row as he says! I’m really into orgasm control and overstimulation so that really turned me on.

I typed this whilst humping a vibrator and NOT cumming!! I’m very good.

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u/KeepMeFromDreaming — 1 month ago

I Didn’t Think I’d be Back so Soon + Day 3 of Denial + High

Wordle guy here. I’m officially on day 3 of my week long orgasm denial (technically day 4 orgasm free, but I ruined on day 1 so we reset the timer) of my orgasm denial, and my boyfriend FINALLY Allowed me to touch myself today (twice) after I begged him. I’m so happy and needy, but so far I’ve managed to not ruin or cum because I’m very good, but it’s been hard. Even without touching, I’ve been getting wet and desperate so easily recently!

So anyway, I had two THC drinks with the hope of relaxing a little, and it’s worked okay. I’m all hazy and needy and wet, but unfortunately my boyfriend can’t text me right now, which is so frustrating. Earlier he was telling me about an idea he has for a punishment if I ended up cumming: If I cum, I have to cum as many times in a row as he says! I’m really into orgasm control and overstimulation so that really turned me on.

I typed this whilst humping a vibrator and NOT cumming!! I’m very good.

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u/KeepMeFromDreaming — 1 month ago

Update from the wordle denial guy + 1 week orgasm denial

God how do I even start this… I posted here a few weeks ago about my boyfriend (Trans man 19) and I (Trans man 20) wanting to get into orgasm denial and how we were looking for advice. Some of you gave us really good advice, and we’ve been taking it into consideration. Anyway, things are going great!

For a refresher, I’m not allowed to touch myself without permission. I’m not allowed to cum unless he makes me cum, with the caveat of being allowed to cum if I get the daily worlde, if I beat him in scrabble, or if I correctly answer a riddle of his choice. So far I’ve been cumming a couple times a week because I’ve been getting better at the wordle. On the days I’m allowed to cum I have to roll a d6, and multiple my die roll by 2, which is the number of edges I have to complete before I’m allowed to cum. I try to avoid them, but up until recently he didn’t really care if I ruined or not.

We’re long distance, so we’ve mostly been doing stuff over text, but recently we had phone sex for the first time and it was amazing. I hadn’t cum in like, a day or two and I was so needy for him. Like, up until we started dating I was never into penetration, but after he let me fuck myself I was spreading my legs and begging him to let me fuck myself harder. Admittedly I cried because I have a lot of sexual trauma, and he’s the first person that sexual stuff hasn’t felt gross and off putting with. I love him so much.

Now comes my evil predicament. I asked him to be meaner to me, and WOW he has been meaner! I recently started a week of denial where I’m not allowed to cum at all or ruin, and I accidentally ruined, so I had to reset the timer. I begged him to let me touch myself again, and my boyfriend being the absolute sweetheart he is agreed! That’s when it happened… I ruined again. So we reset the timer, and agreed that I wouldn’t be allowed to touch myself all day the next day, which was yesterday.

I expected to be able to touch myself today, after all I was good all of yesterday. So I get all dressed up in a cute little cowboy getup with boots and all, and send some hot pictures to my boyfriend. The whole thing turns me on so much that I get wet without even touching, which is rare for me. You know what he says when I ask if I’m allowed to touch myself? He says “No”. So I’m not allowed. It’s so frustrating, but I did this to myself, I was the one who wanted him to be meaner! So now I’m completely at his mercy, hell, he might not even let me cum when the week is up…

He also ordered me to hump something and I’m obliging! Because I’m very very very good! I KNOW YOU’RE SEEING THIS!

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u/KeepMeFromDreaming — 1 month ago

Update from the wordle denial guy + 1 week orgasm denial

God how do I even start this… I posted here a few weeks ago about my boyfriend (Trans man 19) and I (Trans man 20) wanting to get into orgasm denial and how we were looking for advice. Some of you gave us really good advice, and we’ve been taking it into consideration. Anyway, things are going great!

For a refresher, I’m not allowed to touch myself without permission. I’m not allowed to cum unless he makes me cum, with the caveat of being allowed to cum if I get the daily worlde, if I beat him in scrabble, or if I correctly answer a riddle of his choice. So far I’ve been cumming a couple times a week because I’ve been getting better at the wordle. On the days I’m allowed to cum I have to roll a d6, and multiple my die roll by 2, which is the number of edges I have to complete before I’m allowed to cum. I try to avoid them, but up until recently he didn’t really care if I ruined or not.

We’re long distance, so we’ve mostly been doing stuff over text, but recently we had phone sex for the first time and it was amazing. I hadn’t cum in like, a day or two and I was so needy for him. Like, up until we started dating I was never into penetration, but after he let me fuck myself I was spreading my legs and begging him to let me fuck myself harder. Admittedly I cried because I have a lot of sexual trauma, and he’s the first person that sexual stuff hasn’t felt gross and off putting with. I love him so much.

Now comes my evil predicament. I asked him to be meaner to me, and WOW he has been meaner! I recently started a week of denial where I’m not allowed to cum at all or ruin, and I accidentally ruined, so I had to reset the timer. I begged him to let me touch myself again, and my boyfriend being the absolute sweetheart he is agreed! That’s when it happened… I ruined again. So we reset the timer, and agreed that I wouldn’t be allowed to touch myself all day the next day, which was yesterday.

I expected to be able to touch myself today, after all I was good all of yesterday. So I get all dressed up in a cute little cowboy getup with boots and all, and send some hot pictures to my boyfriend. The whole thing turns me on so much that I get wet without even touching, which is rare for me. You know what he says when I ask if I’m allowed to touch myself? He says “No”. So I’m not allowed. It’s so frustrating, but I did this to myself, I was the one who wanted him to be meaner! So now I’m completely at his mercy, hell, he might not even let me cum when the week is up…

He also ordered me to hump something and I’m obliging! Because I’m very very very good! I KNOW YOU’RE SEEING THIS!

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u/KeepMeFromDreaming — 1 month ago

I (Trans Man 20) and my Boyfriend (Trans Man 19) are starting to get into orgasm denial and are looking for advice, and ideas for rules and punishments

My boyfriend and I have recently started talking more about edging and orgasm denial, and him having control over my orgasms. I’ve been into orgasm denial and edging in a surface level way for awhile, but he’s completely new to it. So far we decided that I would only be allowed to touch myself with his permission (I can grind against things though, but I can’t touch myself directly without permission). I’m only allowed to cum when he makes me cum (hard since we’re long distance), gives me permission to, if I get the daily wordle, beat him in scrabble, or answer a riddle correctly.

We’ve been trying to come up with some more potential rules, but are struggling to. We’d also like help coming up with some punishments for me if I disobey and touch myself or cum without permission, which is a bit difficult to do since go to punishments (anything to do with pain) are a no go (He’s not a sadist, and I’m a masochist).

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u/KeepMeFromDreaming — 2 months ago