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The Dick Diary...
Welcome to The Dick Diary. Throughout the years, I have had countless sessions. As I think back and recount on some of the funniest things that I have had subs do and new experiences along the way, I wanted to share the short stories with you. Below you will find those moments. This is a complete insight to the devious mind that I have.
So sit back, relax, grab some popcorn and enjoy the ride. While reading The Dick Diary, you won't be able to help but laugh, shake your head in disappointment and walk away thinking what the fuck did I just read.
Dont forget to follow The Dick Diary on X (Twiiter) where all stories are posted some with pictures. Click Here
Dick Diary Entry: October 16, 2025
Time to get in the Halloween spirit. My sub has been asking for something special to get on here and I came up with the opportunity of a lifetime.
I told him to get a pumpkin. Once he got the pumpkin I told him to carve eyes and a mouth, but that would be just too basic. I want two holes in the back, pumussy and bumpkin. He was not allowed to clean out the insides either. This is Poppi, his newest girlfriend.
I know how badly he wanted to make love to it, but like a proper lady she needed to be put in the mood. I told him to start off by making out with Poppi. When I tell you this sub put his all into making Poppi excited he went all in. He started by caressing her head, rubbing it slightly softly gently before he licked his lips and started planting a big one on her mouth, then the tongue action started. The passion, embrace and amount of effort put into making Poppi’s pumussy wet… top tear.
Now it was time for a blowjob. He got his little dick out of his pink panties and started to get it hard. I can tell he has been thinking about this all week. He slowly brushed his dick on her lips before pushing all the way in, like a true gentleman. Slowly he embraced her head while she was on top of a stool.
As he got more and more excited he begged to fuck her pumussy and bumpkin. After adequate begging, I allowed him the pleasure. He bent her over slightly as took her sweet pumussy. As he pounded faster and faster I told him to finish in Poppi's bumpkin.
I sent him voice notes trying to fight back hysterically laughing, encouraging him to go deeper and make sweet love to her, he begged me to allow him to cum.
As I gave him permission to release deep inside her… she got filled up. Watching the cum fall out her bumpkin, I was in tears laughing.
Now that's a pumpkin cream pie.
I told him to go and give her a rim job and clean her bumpkin clean. He propped her up and went to town licking and motorboating that ass clean.
Now he will never look at a pumpkin the same again.
Trick or treat bitch.
​
Dick Diary Entry: October 5, 2025
I had a session with my sub that comes to Me every quarter. He saves up a huge chunk of money so we can have a very long cam session. This time he decided he wanted a two hour cam session and 10 tasks leading up to it.
When he booked the session he put himself in chastity. On the day of the session it will be 10 days. I started on Monday by sending him one task a day and then Thursday I sent him the full list that way he had Friday and all day Saturday to complete as many tasks as he could before we had the session, he ended up getting through seven out of 10 tasks. I was very surprised he even got that much done.
his last task before the session was to get fully dressed up in a sissy outfit and do his make up. I wanted him dressed to the nines. he wore a little black dress with fishnet tights and 7 inch pleaser heels.
One of his favorite kinks is anal training, so I knew that we were going to have a ton of anal toys to play with. This sub is a huge toy collector. He loves collecting toys and wanted me to pick out two toys before we had the session so he could get them ordered and sent to his house. I had him go to the lovense website as those are My favorite toys as they are ones I control from my phone. I told him to get the mini fuck machine as well as Solace Pro, the one that jerks him off. Needless to say, he was very excited about these.
We started off the session with him, taking the plug that he has in completely out and starting with his smallest plug. Now the smallest plug for him is going to be a large size for the normal person. He easily took that plug like a champ. I had him put the plug all the way in, sit up and rock his hips so he can feel the full thickness and length of the plug in the walls inside of him. Then I had him take his vibrating wand and sit on that while he was rocking it was driving him absolutely crazy.
From there we moved on to his plug that looks like a bunch of balls each one getting thicker and thicker. I had him put it in and pull it out over each ball, at that point he was ready to be fucked by this machine.
I had him put a pillow underneath him for leverage and lay down with his heels, fishnets and fully dressed up with his wig still on. I started to fuck him slowly mind you he is still in chastity at this time.
At the beginning of the session, we talked about him coming twice, but first I wanted to get his ass in gear. I slowly started fucking him with the machine, going faster and faster watching his body go absolutely crazy. He could barely hold on his, cage was getting tighter and tighter and he was begging to come at this point.
I told him to get his vibrating wand, put it on his dick while I him fuck him. I told him if he really wanted to come, he would of course have to eat as he couldn't let any of it go to waste.
he was begging to let go, and I counted him down to come. It was a huge load to say the least and of course he ate every last drop. I told him to go collect himself and drink some water, get hydrated and get ready for the next round. He let me know that his ass is very sore and he doesn't know if he can handle anymore but he could definitely come again because we did still have the other toy he wanted to play with.
I told him to keep the chastity cage on for now and put the spread bar on and do some sissy poses. I told him to reach down, grab his ankles and walk around. I remembered he had nipple clamps, so I told him to put them both on and put the chain in his mouth while he walked around the room. It was absolutely hilarious watching him walk around like the hunchback with the spread bar in between his legs and him trying to keep his head down, so the chains wouldn't pull his nipple clamps.
After he took off the bar and then nipple clams I told him to put on his full mask that has sensory deprivation (Vision) as well as a gag in it, take the vibrating dildo and put it on his dick as I allowed him to come out of his cage. watching him get so sensitive I couldn't help but laugh as he was convulsing laying there.
I had him take off the mask and get the final toy that I controlled to jerk him off. I had him put it on, and I stroked him hard fast and long until he begged every last moment to come. The toy ended up slipping off and he couldn't help but beg to jerk until he came and I allowed it.
He came so hard that he could barely move, Exactly how I told him I was going to leave him… fucked in every way, Stretched and tired as fuck. Needless to say he will be looking forward to his next quarterly visit.
Dick Diary Entry: September 22, 2025
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Tonight My sub messaged to book a session. We went back-and-forth with different things that he wanted to do as he's had several sessions with Me and we have a very tight bond. He's always been very good, loyal and communicates correctly. A model sub. Tonight though there must've been something in the air.
We were chatting for about five minutes when we landed on a surprise session. It was a five minute cam with whatever I wanted to do, no limits. Normally we do a 20 minute session with specific kinks and fetishes that he likes, one of them being financial domination where I charge him to take off things like his chastity cage, my robe, etc. So this one is very condensed compared to what he's normally used to.
After I told him the amount to send, he said "let me think”. I agreed and gave him the time that he needed thinking he would only need a few minutes. Mind you we started messaging about the session at 12:39 AM. After five minutes passed… then 10 and ultimately turned into 39 minutes, it was now 1:39 AM. Needless to say I was not too happy about waiting.
We went over everything once more before he sent for the session and then I started getting ready. I always like to enter in sessions and see how things flow, not really preplanning them ahead of time, but with this one I had free rain to do whatever I wanted and I knew it was going to be a good one due to being in one of those moods from waiting. I was curious why I was waiting so long, so I needed an explanation as he didn't say anything when he first messaged me back after the time passed.
We started the cam session, I told him to completely undress. This is where the fun really begins. After he was undressed, I instructed him to smack his dick 3 times. Then I told him to get onto his knees and start stroking. Once he was on his knees and he started on his first edge, I started asking what was the reasoning behind him taking so long to message Me between booking and actually sending. What did he need all this time for I mean, let's be honest 39 minutes is a long time to make a decision when you're horny.
He starts confessing to Me that he got distracted, playing his video games with his friends. Needless to say that did not go over well. After taking off my robe I sat on my couch as he was kneeled stroking on the floor. I got really close to the camera and I asked him why he thought it was more important to put his video games before Me, then he apologized. I told him you're not sorry but you will be. Throughout our time, I made him edge several times as we were chatting about how important it is to put me first.
I asked him if he has ever been denied before and he said no I started laughing and telling him how funny it would be if I just denied him for being a little bitch and not putting Me first. Then the wheels really turned in my head.
I asked him a couple questions about the game that he was playing, if it was one of those games like a battle Royale that has rounds. He let Me know that it was. I advised him for his punishment because I know he was playing with his friends after the session. he was going to be up for another hour, he was not allowed to cum at the end of our session before we got off cam. If he really wants to cum, he would need to edge once every 15 minutes while he is playing the game. he cannot mute his mic, and he cannot stop gameplay. he had to start at the top of the hour and edge on time no matter what.
I remember how sensitive he got when he put his vibrator on his dick so I told him on the third edge at the 30 minute mark, he would need to use the vibrator and that time he was able to mute his mic. On the fifth edge, he is allowed to come, but he still has to do it on Mic and then eat it up.
He reluctantly agreed because he was so immersed and so excited he was about to do anything to come. Needless to say, he's never going to disobey Me and put his video games first again.
Dick Diary Entry: August 29, 2025
Tonight My sub was having a good time partying. He indulged in some snow, weed and liquor. While doing a bit of forced intox he told Me he has some toys to play with during our session. I asked him to send me a picture. Contents of the picture: a rubber band ball, Hitachi wand and a box of medical gloves, orange to be exact.
This started the wheels in My mind turning instantly. The second I saw the gloves a light bulb went off and I couldn't stop laughing. What was going to transpire next… The devious thoughts that came out of My mind were hilarious. I told him I wanted him to take the glove and blow it up. That was not the end, oh no… that would be to basic.
After he blew it up I wanted him to rubberband it on his dick. He tried a few times after laughing hard not being able to do it. Then he sends Me a video of a bag. I asked him what was in it. Next thing I know he has a tube that he is blowing air into to inflate the glove on his dick. It was truly one of the funniest, most innovative things I have seen a sub do. Honestly a night we will never forget.
Dick Diary Entry: August 20, 2025
I have a sub that wanted to try something new and on the list of things he wanted to try was food play. I told him to go pick up five things in the kitchen for me to choose from for him to use. He picked out ranch dressing, Greek yogurt, hot sauce, lime, and a bag of rice. I told him to slather his balls in the Greek yogurt covered up, get it all over. It was definitely a mess after that I told him to put some rice onto a plate and teabag the rice, so all stuck to his balls. I told him I wanted him to crawl around the house like a bitch on all 4s. he crawled across the room tiny little pieces of rice would fall off. Every time he sees a little, he's going to think about me as I'm sure he'll be finding them for years to come. (See comments for video)
Dick Diary Entry: August 3, 2025
I have a sub who likes to call me on business trips. This particular one who was staying at an Airbnb and we wanted to have some kinky fun, but couldn't quite figure out where a great place for him to cum would be. he looked around the room named a couple things and we landed on a plant. I told him to walk over and give that plant some nutrients. It was a very basic little plant. Something that you can easily find out Walmart. he proceeded jerk off into the plant feed it his protein. After he finished and had his clarity I told him now he hast to go to Walmart and replace the plant and take that one home. I told him he needs to candidly message the Airbnb host and tell them that he dropped the plant yet he replaced it because he felt so bad now he keeps that plant on his nightstand in his bedroom and its thriving.
Dick Diary Entry: July 23, 2025
I have a sub who LOVE public humiliation. It was a late night and he wanted to go out to his local coffee drive through. It's a 24hr bikini coffee place where they know him well there as we have had him drive up in full sissy outfits in the past. Everything from a wig, lipstick, bra, panties, dress and heels.
I wanted to take it to another level this time, so I had him take his largest dildo with him. he pulled up and ordered his coffee at the first window then drove to the second one. At the second window, I told him to pull out his dildo and see if they would be game to put whip cream on the tip for him to lick it off. The could not stop laughing. As I was on the call with him, only watching him but hearing the girls in the background, they couldn't stop giggling. he licked all the whipcream off the tip like a good sissy bitch. I told him to thank them for the fake cum and tip everyone there.
Dick Diary Entry: July 16, 2025
Today I did a double Domme session and the sub was laying there on the bathroom floor on a towel. he requested that We do some tasks with his dick so with the limited items We had we came up with toothpaste. First, I told him to put a big dollop on the head of his dick and rub it in. The other Domme told him to slather it all over his balls. This toothpaste did not look like toothpaste but more like lotion. When We called him out he said it was "a more natural toothpaste". After he rubbed more in I told him to grab his toothbrush and brush his dick clean. I wasn't done yet. I told him because he loves his natural toothpaste soo much he can use his own natural paste for his teeth. It was time for him to cum, I told him to grab the toothbrush, cum on it, and than brush his teeth. Now im sure they are pearly white.
Dick Diary Entry: July 6, 2025
I have a sub that's into Sph. Well, I'm not sure if he's really into Sph but he definitely has a small dick. He wanted some humiliation so I told him to get a toilet paper roll. All the toilet paper was taken off so it was empty. I told him to put it on his dick and use it as a pocket pussy. It was definitely a real life pocket pussy because it didn't even fit his dick. His dick was only halfway , couldn't even see the tip at the end. There was such a shadow in there because it was so deep down was absolutely hilarious watching him try to jerk off with this toilet paper roll.
Dick Diary Entry: July 3, 2025
My sub is into humiliation. When he showed me his dick, I couldn't help but laugh. It was tri-colored. I told him it looks like he dipped his dick into a pint of Neapolitan ice cream permanently. lmao.
Dick Diary Entry: June 27, 2025
I used to have a sub who loved a multi Domme session. It would be two other Dommes and I. We would spend HOURS on a call sharing our screen (like Teamviewer) scrolling though his instagram... yes instagram, that he gave us the log in for. This was not just his regular IG, he made this one just for gooning.
We would do these sessions at least once a month, same thing every time. Once in a while he would pull out a butt plug and we would control it to spice things up. We knew he was on snow and probably drinking.
He would goon to pretty women in evening gowns, super tan women (from Florida), women in parking garages among other things. The ladies and I would talk about how they all had hairy assholes that he loved. Sometimes when he did talk he would tell us that they are his Domme or he knows them irl and tell us stories. During the call he would be mostly silent otherwise, it would be up to us girls to chat about the pretty women and keep ourselves entertained.
One time I told the girls we should make a bingo card with all the things we knew we would see as it was repetitive and play bingo during our time with him. One of the ladies found an app to make the cards to randomly generate with the different boxes we could mark off. We did a $10 buy in for each round and sent the money to the winner after. It made the several hours go by quicker.
He would normally start off with 2 hours and typically extend to about 6-8 hours. The longest session I had with him was 2 days on and off... only being off for time to sleep and a bit of time to eat if that. He also liked to start around 10-11 PM so when we got a message from him, we knew it was an all nighter but the money was totally worth it.
Dick Diary Entry: June 26 2025
I just finished up a session that I couldn't help but laugh so I wanted to share it with you guys. I had a sub that has been pretty consistent with Me, he gets a cam session. He always plays with this tiny little butt plug. It's probably the size of his finger, but he absolutely loves it. I had him put his legs up as high as he can while he is laying on his back curling his head up so he can see Me and play with the butt plug pushing it in out, moving it around, ect. I started telling him to stroke but only to edge for Me. Apparently it felt so good that he was startled when he came and landed right on his face, he jolted with surprise. He did not have permission to come yet, but he couldn't help himself. It seem like he didn't even know it was cumming.
Dick Diary Entry: June 15, 2025
I had a sub that used to call me from a hotel room when he was on his business trip every time he traveled. One time I told him on our phone call that I wanted him to take a bible from the nightstand as most hotels at that time had them, from the room and use it on his dick. The only thing that he could find was Virginia magazine. So I told him he needs to fuck this Virginia magazine. I told him from now on this is going to be his new girlfriend Virginia. We still talk to this day and when he goes on a business trip, we always make it a point to check if Virginia is still in the room.
Dick Diary Entry: June 7, 2025
Tonight I gave my sub the best sex he has ever had. Oh no, it wasnt with Me... ofc not. That would never happen. Instead i got him a new girlfriend of the porcelain kind. I told him to lift up the lid, then the seat, place his dick on the toilet bowl, put down the seat and press down on it. his tiny little dick barely fit but he pleased his new girlfriend well.
Dick Diary Entry: June 2, 2025
I had a session with one of My subs who enjoyed anal. After having a bad day I wanted a good laugh so I told him to get some hard boiled eggs. After they cooled I told him to put them up his ass and bock like a chicken each time one went in. Then I told him to go lay his eggs and bock every time.
Dick Diary Entry: May 30, 2025
I have a sub that loves to partake in snow. He always loves to message Me and do little tasks. I get him to strip, make his underwear into panties and swing his saggy balls to make me laugh. As per usual we got to that time of the night where he wanted to do anal. As I knew he was confined to the bathroom, I told him to use the plunger. he placed a condom on that bitch, stick it to the floor and fucked his ass.
Dick Diary Entry: May 30, 2025
One of my favorite things for subs to use is binder clips. They are stronger and larger than clothespins. I had my sub line them up on the shaft of his dick and nipples, then hit them off with a wooden spoon. I'm sure it pinched... just a bit, but I didn't feel a thing.
Dick Diary Entry: May 26, 2025
I had a sub that was into public humiliation. I gave him the task to go to Walmart and put the following in his kart: condoms, lube, a pink thong, zip ties, cloths pins, cucumber, crunchy peanut butter, dog treats and duct tape. He had to walk around the store with everything in his cart for 15 minutes and then go to an actual cashier. He is not permitted to use the self check out. He also had to carry it all out. I told him to figure it out… no bag.
Dick Diary Entry: May 24, 2025
My sub really wanted to do anal, but he didn’t have any toys. We were doing a little bit of forced Intox and I told him to send Me a video of what was around his room. Right on his table was a 1.75 liter bottle of Tito’s. That’s when My brilliance struck. I told him that I wanted him to use the Tito‘s bottle. I told him to grab the handle and fuck his ass.
Dick Diary Entry: May 23, 2025
I once made My sub drink 8 ounces of water every 15 minutes. he was not permitted to use the bathroom unless I specifically gave him permission. After a few hours, I gave him permission to relieve himself, but not in any easy way. he had to crawl outside, lift up his leg and pee on a tree like the bitch he is.
Dick Diary Entry: May 21, 2025
My sub loves food play. I wanted to come up with something creative to have him use as lube. I thought that very crunchy peanut butter would be the best option. Ever since then his new name is PeanutButter Boy .
Dick Diary Entry: May 19, 2025
I was craving some ice cream and my sub said that sounds good and he will get some to. I told him to lay down, put a scoop on his dick and balls with chocolate syrup, whip cream and a cherry on top. then he ate it.
Dick Diary Entry: May 19, 2025
I put my sub in a debt contract and every time he gets to almost paying it off for some reason all the payments get lost so all the interest and the balance are the only thing that shows. Due to this error he just has to continue to pay it back down. Funny how that happens.
Dick Diary Entry: May 18, 2025
I did a poll to see what My sub should change his email to and MoistlyPlanties69 won. Now he will change all his email address at his bank, call phone provider and anything else he uses. Imagine him needing to verify every time he calls in.... Priceless.
Dick Diary Entry: May 18, 2025
I had a sub that was really into vore. I would shrink him down to 2 inches and swallow him whole, describing to him how it felt to slide down My esophagus. I would ask him while he was in my stomach if he can see all the bones from all the other men I have eaten.
Dick Diary Entry: May 17, 2025
I had a long time local sub ask Me to lock him up in chastity. I had him pick Me up and take Me to in-and-out to get me some food before I locked up his pretty pink cadge then take Me home. He was locked up for 3 months till I unlocked him after he bought me Cheesecake Factory.
Dick Diary Entry: May 17, 2025
My sub and his had a horrible relationship before he passed away. I told My sub it is time you fuck over your dad. As he cremated him, I told him to take the urn, open it up and fuck his dad's ashes and then cum on them.
Dick Diary Entry: May 16, 2025
My sub that is into CBT wanted me to have him tie up his balls today. I told him to find some rubber bands. he found three yellow, blue, and green. I had him type his dick and balls for an hour and then untie himself. After that, I wanted a little reminder of Me everywhere he went so I told him to put the blue rubber band (My favorite color) on his keychain so he can always remember how much I have his nuts in a clench.
Dick Diary Entry: May 16, 2025
I once had a sub who enjoyed anal. We wanted to use something around the house so I thought a toilet brush would be the perfect thing. I had him put it in his ass and hop around like a bunny with his little tail sticking out.
Dick Diary Entry: May 15, 2025
I once had a sub who enjoyed anal. We wanted to use something around the house so I thought a toilet brush would be the perfect thing. I had him put it in his ass and hop around like a bunny with his little tail sticking out.
Dick Diary Entry: May 15, 2025
Had a sub cum into his shoe and wear it to work. squish squish
Dick Diary Entry: May 13, 2025
My sub wanted to spice things up so I told him to put hot sauce on his dick and shove a piece of sliced ginger up his ass.
Dick Diary Entry: May 15, 2025
Told My sub to go to a glory hole dressed up in fully sissy with sucking dick for Goddess Crystal written on a sign on his chest. he managed to suck 3 dicks and ate 2 loads before he left..
Dick Diary Entry: May 13, 2025
Today My sissy got all dressed up in a cute bra, panty, heels and a dress to run some errands. First I told him to go on a walk on a populatied train outside. After he went to get some water at a gas station. Last he went to a sex shop... sill dressed and bought some more panties. It was a fun day out full of laughs.
Dick Diary Entry: May 14, 2025
I did a double Domme session with a mutual of Mine today. It was a live video response session. During the session the sub was so intimidated to chat. Between the other Domme and I degrading him and talking sh*t to him because he thought it was appropriate to take pics of his dick on the toilet, but it was seven minutes in heaven for him.
Dick Diary Entry: May 13, 2025
My sub wanted to spice things up so I told him to put hot sauce on his dick and shove a piece of sliced ginger up his ass.
Dick Diary Entry: May 12, 2025
Today I made my sub get dressed up in a dress, pantyhose and he decided to wear crocs go to torrid completely dressed up. While he was at torrid, he went and bought a new dress and a pair of heels and was told that he had to wear them out of the store. After he left the store, I made him go for a hike in this outfit in the wilderness on a public trail.
Dick Diary Entry: May 12, 2025
In today's diary had to sub that wanted to be transformed into a female with a remote so with one zap, he had boobs and another he had a vagina then I took him to a bar and whored him out. Good times.
Dick Diary Entry: May 12, 2025
I specialize in subs that are newer to the space. This sub in particular reached out to me and told me that this would be the first session that he has ever had. He was looking for a soft dominant experience and to expand his horizon on his kinks and fetishes. We did just that and now he is hooked.
Dick Diary Entry: May 12, 2025
I had a guy lick the cream out of an Oreo, and then put his own cream on it and then eat the Oreo. the best CEI he has had with his creamy goodness
Dick Diary Entry: May 12, 2025
Today I had a sub tell me that his fetish was headless women. he ordered a custom where the camera is going to be positioned on the table and all you're going to be able to see is my head. he literally only wants me to do facial expressions him and give him the side. I basically ignoring him.
Dick Diary Entry: May 12, 2025
I had a cam session that involves CBT. I really wanted to laugh so I made him put toothpaste on the tip of his dick and rub it in. It was absolutely hilarious.