My Sissy Bucket List

Just want to open up this piece with a little apology for my hiatus from continuing to document my time serving J. Life has just been so busy, and it's tough to find some time to write. Anyway, as you can probably clearly tell by the title of this piece, it is not a part of the Panty Boy Diaries series that I've previously started, and you do not have to have read those entries to be able to understand this one. This is more of a one-off documentation of some of the kinky fantasies that I hope to be able to accomplish now that my sexual desires have evolved.

Before I present the list and explain the reasoning behind each act, I want to make it known that I've given myself basic rules for this. I must get each act on the list either photographed or recorded on video so that there is actual evidence that I performed the act before I can cross it off of the bucket list. This is the main rule and premise for the list because it fuels my greatest turn-on, the need for humiliation. The idea of having evidence that other people can see is so erotic because I'm very much private and discrete with this side of my life.

The other rule is a minor one, but I have it because I am also a reasonable person who prefers to maintain safety. It's also a little bit contrary to my previous comment of enjoying the idea of having others see the pictures or videos of me. The rule itself is that even though I am going to be documenting my performances, I am also going to make sure that it is hard to definitively identify me in the photos. This is a personal bucket list after all, and I just can't risk people in my life knowing about this part of my life. It's just the idea that people might be able to see the photos that I find erotic, not the actual act of being outed that turns me on.

One last thing that I want to point out before I get on to the actual list is that I have already performed most, if not all, of the tasks on the list, but I have never been able to work up the courage to document them. Not being able to look back at physical evidence of what a slut I am is one of my biggest regrets, and the driving force behind why I've put this list together.

Anyway, now that I've got that out of the way, I can get to the fun stuff, the list itself. I'll number the list based on the level of humiliation. So the list will escalate from the least humiliating tasks to the most humiliating. Each task will also have a description about why I chose to include it. Let's begin.

1. Have a photo taken of me where I am completely dressed up and on my knees presenting myself for a daddy/top.

This is on the list because it was very commonly the first thing for me to do or be asked to do once I got dressed up. I enjoy playing with dominant men who enjoy humiliating me because that's what gets me excited. I like feeling like I'm being made to submit to a superior alpha male. When compared to a true alpha, I am inferior and have to assume the submissive role. I absolutely love it when a man can take charge to put me in my place and that his duty is to show me the difference between him, a real alpha male, and me, an inferior sissy slut. Whether it's kneeling and begging to be used or getting face down and pulling my cheeks apart to present my boy pussy to them. There's no better way for them to get this point across than to have me get down on my knees in front of them and present myself for their pleasure.

I've done this task a handful of times now and was surprised to learn just how much this turned me on. The first few times I would meet up to play, I would get dressed solo in a different room such as a bathroom or a guest bedroom beforehand. I prefer doing this part solo because it gives me a little bit of time to calm my nerves and get in the right mindset. With each article of clothing I would put on I would feel more and more slutty and less and less like a man, but once I've got the outfit on, I would often find myself not knowing what to do or expect when I walk into the room where the man is and this just wasn't acceptable.

Now that I know what I like and how I like to feel when in the presence of a man, I know that I absolutely love it for him to establish the power dynamic right away. I still remember the first time I experienced this. I was wearing nude stiletto sandals with a 3 inch heel, white thigh high stockings, a white g-string and lacy white choker. I had just stepped out of the motel bathroom where I got ready and turned the corner to find my master, as he wanted to be called, completely naked and closing the curtains. Even though there was carpet on the floor, I think he heard me walk in because he turned around and we made eye contact for a brief moment. I was silent and unsure of what to do so I opened my mouth and asked him if he liked the way I looked. He quickly walked up to me so that we were face to face and took hold of my face with one hand as if he was inspecting it. He then proceeded to push me to my knees and said that as his bitch I was not allowed to stand up in his presence, and that before we got started I had to pledge my submission to him. He then coached me on the proper pledging position which was on my knees with my hands on my thighs one over the other and my ass had to be touching the heels of my shoes. Since I was wearing a g-string, I remember feeling the thin heels touching my bare ass cheeks and afterwards thought to myself that I wished I could see what I looked like in that moment. The memory of having that naked man stand over me as I kneeled, his flaccid cock about an arms length away from my face, is why I have decided to include this on my list of sissy tasks to document.

2. Taking a photo of one of my hands wrapped around a hard cock.

For this photo, I would definitely want my nails to be done nice and pretty. Preferably a girly shade like hot pink, but I wouldn't mind if they were purple or red either. I know you've all seen photos like this or this exact scene in a porno. The girl is getting ready for some foreplay and the first thing she does is grab hold of the guy's cock. It's that exact moment that I want captured and documented. This is on the list because this is often my first point of sexual contact with the man. It's my first official physical act of submission. Taking hold of another man's cock is so humiliating for me because all of the cocks I've had my hands on have been much bigger than my own. I get a real sense of what a real cock should feel like and just how heavy they are compared to my own minuscule clit. It's almost as if the weight of a man's cock helps to push me down further into my submission and degradation.

I'm by no means a size queen, but for the purposes of this task, I think the bigger and the thicker the cock, the better. It's quite simple really, the bigger the cock, the smaller my hand looks and I'm hoping to be able to find a cock that makes my hand look dainty. I want the photo to emphasize how girly my manicured hand is. I want it to look like I depend on his cock, that my hand being on it puts me at ease, that my hand belongs on his cock. In that moment, I'm nothing more than his cock holder.

3. Have a photo taken or video recorded of me either kissing the tip of a cock or holding just the head of a cock in my mouth.

We're now moving on to the more sexual part of the list with this being the first actual form of sex that I want documented. I cannot stress enough how turned on I get thinking about the men that have made me give their cocks a "thank you" or "goodbye" kiss after they're done using me or the time that I was made to be a cock warmer and hold just the head of the cock in my mouth while the man took a phone call. These are the types of acts that I would like captured on photo or video.

The angle of the photo/video would be a POV angle from the man's perspective where he is looking down at me as I kneel before him. It's going to be so humiliating to ask him to capture the moment that I surrender my masculinity to him. I would like to be in the pledging position that I mentioned earlier in task number 1, and for him to treat the act of me kissing the tip of his cock like it's me signing a contract that gives him full control for the night. However, instead of putting ink to paper, I would be putting lipstick/lip gloss to cock head. I'm usually not a fan of overly messy surroundings as a result of sex, but for this task I want to be wearing a bright shade of pink or red lipstick with plenty of shiny gloss so that I can leave a mark on his cock when I'm done. My lips should look like there only purpose is to kiss cock.

If you've read some of my other work, you know that I'm not a very big fan of kissing, oral sex, or giving blowjobs. This is still the case, but I'm always willing to compromise and submit if the man is truly worth it. With that being said, I love watching videos or seeing pics of girls and other sissies first take cock in their mouth. I love the way their made up lips stretch and form an O shape to accept the cock. So, because of this, I want my own pics or video where I'm the one on my knees with my O shaped mouth leaving a lipstick print on alpha male cock.

4. Have a photo taken of me kneeling in between a man's legs with my head in his crotch servicing him as he is seated on his couch/favourite chair watching TV.

Similar to task 3, this task is inspired by the pics that I've seen. Some of my favourite pics to look at when I am horny are ones where the man is simply relaxing after what I assume is a long day at work and he's got his woman or his sissy kneeling down in between his spread legs with her head in his crotch.

My favourite angle for these photos, and the angle that I want my photo to be taken at, is where the sissy's back is to the camera. The viewer can only see their back, the bottom of their heels as they kneel and the back of their head. This is the angle that I want my photo taken at because since it is a photo the viewer will ultimately not know for sure that I am sucking dick. They can only imagine that that's what's happening. Now, I imagine that there are no alpha men that are going to allow me to just get into this position and not suck them off, so I doubt I will be able to just stage this photo. I fully realize that I'm going to have to swallow my pride, pun intended, and suck some dick to be able to cross this task off of my bucket list.

I've actually never done this task before, but I have fantasized about it. In my fantasy, I'm dressed in a super skimpy french maid outfit. I've got the little cap on top of a black bob cut wig, and I'm wearing just a shiny black and white apron that doesn't actually cover anything. Beneath the apron, I'm wearing a black thong and I also have black thigh high stockings with bows at the top by the backs of my thighs. To top off the look, I'm in a pair of sky high 6 inch black patent leather peep toe heels. I'm cleaning the house of my daddy while I wait for him to make his way home from work. I hear the door open and close as he enters the home. He kicks off his shoes, drops off his belongings and makes his way into the living room where he plops down onto his favourite recliner and turns on the TV to his favourite sports channel. Having finished with my cleaning, I make my way into the room and, without a word, I saunter over to where he's seated. Again, without a word, I drop down to my knees and undo his belt, open up the zipper and, with a little bit of his help, take off his pants. As always, daddy went commando so I have easy access to his wonderful cock. Once his cock is out in the open, I go to work on cleaning him up. He's had a stressful day at work and it's my job to help him unwind so I kiss and lick his shaft all over using just my mouth since daddy likes his blowjobs hands free. He lets out a light moan signalling to me that he's ready for me to take it in my mouth and I do just that. He then says every sissy's favourite 2 word phrase and calls me a good girl. For the next half hour, all you can hear in the room is the people on the TV talking about how exciting the March Madness basketball tournament is, and me slurping on daddy's dick. Right on cue, he blows his load into my mouth and I open wide and stick out my tongue to show him that I got it all before I swallow the load. This is the visual that I want running through people's minds if they were to see the photo of me performing task number 4.

5. Have a video recorded of me being fucked on my back with my legs on a man's shoulders.

I can almost guarantee that every sissy has a similar fantasy about being fucked like this. It's such a powerful reinforcement of my submission seeing my stocking covered legs in the air, painted toes pointing to the ceiling and my feet in a nice pair of fuck me pumps. In this position I am constantly reminded just how much of a sissy I am, and that in this moment, I'm not a man. Just a bitch. Not only because there is obviously a dick pounding my ass at this point, but because every time I open my eyes I am reminded that I am dressed like a woman.

I would want the POV of this video to be from my perspective. I want to hit play on this video and have the viewer looking up towards the ceiling. They'd be able to see my calves resting on his broad, manly shoulders as they shake in sync with his thrusts. I want to be able to see what colour my toenails were through my stockings. This means that I'll most likely be wearing opened toe heels, and I have a strong preference for the heels to have a strap that goes around my ankles. I find it a lot more visually appealing if the heels aren't flailing around while I'm being manhandled. From this angle, the viewer would also be able to see the facial expressions that the man is making as he fucks me, and his expressions will show the face of dominance.

Only my legs would be visible in the video so a big part of the excitement generated from it will be the audio. I want to be able to hear myself whimper and moan as he's fucking me. Hopefully, he's really giving it to me so that I can also hear the sound of his body colliding with the back of my thighs and my ass cheeks. This will help me to remember how I felt, and leave no doubt in the viewers mind as to what's happening in the video.

6. Have a photo taken of me with my face down and ass up, being mounted balls deep by a man.

In my opinion, there is no single photo that would be more humiliating than this one. In this photo, I'm going to be completely naked except for some knee high cheerleader socks that have stripes at the top. I'll also have a small pink chastity cage on my clit. My face and shoulders will be pinned down to the bed by the guy and and my ass will be as high in the air as possible. The photo itself will be taken from behind us, so that you can see the man standing over me with his cock buried balls deep inside of me. His big balls will be rested right above my little ones so that the viewer can see the difference in size. You'll also be able to see my toes curled in my socks. This is on the list because it's the point of no return. At this exact moment, he can go no deeper inside of me, his entire cock is in me. I've accepted all that he has to offer. I will be completely dominated at the point that this photo is taken.

7. Have a photo taken or video recorded of me being fucked doggy style with my back arched and the man fucking me has a fistful of my hair in his hand.

I'm currently leaning towards getting this on video since it's similar to task 5 where the emphasis is on the act of me being fucked unlike task 6 where the emphasis is on the specific point in time where I have the entirety of another mans cock in me. I think that this task will also be one of the harder ones to figure out since this will be the first task that has my whole body clearly in it. I want this video shot from the side of the bed and for both me and the man to be in it.

We all know what doggy style looks like. I want the video to capture me on my hands and knees with a man taking me from behind. I envision myself wearing school girl outfit for this task. I will have on white knee high socks, some slutty Mary Jane heels, a plaid mini skirt and a tiny white blouse tied up above my belly. The skirt will be flipped up onto my lower back to give better access to my boy pussy, and the man will have a handful of my hair in one hand and his other hand will be on my hip. He'll be pulling my head back to make sure that my back is arched and so that he can also pull me onto his cock harder because he's not satisfied with the effort I'm putting into meeting his thrusts. It'll be very clear who's in charge in this video.

I want it to look like I'm struggling to get away and that it's clear I'm having difficulty taking his dick during this fucking. This is because I have consensual non-consent fantasies. It's actually one of my bigger fantasies in which I am forcefully taken and I do my best to fight it, but because he is just superior to me in every way there is no way for me to escape. Throughout the video, I want to clearly show my attitude changing from a point of resistance to a point of acceptance. The first half of the video will be me screaming in pain and begging him to stop, but he maintains that I was being a tease and that I was asking to get fucked. The second half of the video will see my screams of pain transition to moans of pleasure that I can't help but make, and my begging will be for him to fuck me harder. He'll then gloat about how he was right and that he knew that I would enjoy getting fucked the moment he saw me.

I know this isn't for everybody, but for me I really like the idea of the clash of my mind and my body. Mentally I want to resist and make him stop meanwhile physically my body is betraying me by feeling pleasure from the pounding that I'm receiving. That's why this task is on my list.

8. Have a photo of my freshly fucked boy pussy taken.

This one requires a lot less explanation than the others on this list. I just want photo evidence of my boy pussy right after I was fucked. As an optional add-on to this task, I also have a fantasy of getting a photo of my own creampie. I say this is optional because asides from J in my Panty Boy Diaries series, I have never had bareback sex with another man. Boy would it be hot to get a picture of a fresh load leaking out of me though.

9. Have a video recorded of a man putting a butt plug in me right after he's finished fucking me.

If you haven't noticed we're into the post-sex section of the list. I mentioned earlier that I would order this list from least to most humiliating, and I standby that statement. To me, after the man is done with me is the most humiliating part of the date because now is when it all settles in. The lust and desire is gone, and I'm left to think about what I just did. That's where this task fits in to the list.

I want this to be recorded by the alpha male from his perspective. It'll be right after he's finished fucking me and he's deciding if he wants to go another round. He can't seem to make up his mind and so as I'm laying their on my belly, spent and exhausted, he grabs a cute jewelled butt plug and proceeds to insert it into me. As he's doing this he tells me that this is to make sure I don't close up on him so it's easier for him to fuck me again later if he wants to. It also serves as a reminder that I just got fucked. I'll feel it when I sit, with every step I take, with every movement I make essentially.

10. Have a video recorded of me doing the mini walk of shame to the bathroom after being fucked.

The final task on my list. I really only added this because I wanted to have ten tasks on my list. Ten is a nice number for a list after all. I do think that it would be nice to see a video of me making my way to the bathroom to cleanup after I've just been fucked. I know in the moment, it's so embarrassing and I absolutely love it. I'm almost always in heels when I get fucked so as a natural byproduct of that, my ass sways very femininely when I walk and I can only imagine what the guy is thinking as he sees me walk away from him like this. As if walking in heels wasn't hard enough, it doesn't help that my backside is sore which makes it even more difficult to walk. My back is always turned to the guy because they normally like to revel in all their glory and stay behind as I go to get cleaned up, so I never really get a glimpse of what they might be doing. Every step I take reminds me that I was just used for another mans pleasure. I was basically a real life flesh light.