Cockhunting Sissy

May 15th
The beginning…
This is my first entry, one of many for sure as i have been given the task of regularly updating my diary by my beautiful Mistress. She is perfect in every way, combining intelligence, beauty, elegance and cruelty in a way reminiscent of a James Bond villainess. Men crumble at her feet with nothing but a cool glance in their direction and i find myself completely under Her spell, eager to fulfill Her wishes for my public humiliation.
“i am my Mistresses sissy sub, and i want to be forced to suck cock for Her!”
This is my deepest desire and i declare so openly in order that others in our community may help me in my search for cocks that i can suck for my humiliation and the entertainment of my Mistress.

May 19
Thoughts and Fantasies
Mistress has responded to my first entry and was less than pleased. She is satisfied with the task being done promptly but has ordered me to up the ante and write something that is deserving of Her time. my goal is to excite and titillate Her with my deepest, darkest thoughts.
my mission is to find a Master or Dominant male to force me to suck His cock. The thought of being totally submissive to a strong male is a huge turn on; being forced to take a cock and enjoy it is divine humiliation. i am getting nervous and excited just thinking about it!
i do not wish to disappoint my Mistress but the problem is i know me; i need to be forced or i will hesitate. my mind is weak, i am not determined enough without being coerced, spanked or blackmailed. No matter how much i want something i will always falter at the last step, it is a fault that needs addressing promptly.
The most embarrassing scenario i can imagine would to be commanded to worship and suck another sissy cock. Sucking the hard cock of a man dressed up entirely for his own humiliation and satisfaction is extremely degrading. But either way, it does not matter; i just want to suck cock.
Prior to submitting to Mistress i never had any urges or lust towards another man before and i think that this sudden interest will make me a keen and hungry cock sucker.
i am unsure if this has anything to do with my current task (willingly undertaken)but a fantasy of mine is to be taken anally by a woman with a strap on, and even better would be to suck and be fucked by a T/S. The cock is all encompassing and the rest of the body is all woman… Who wouldn’t like that?
i hope i would be forced to take the cock anally; the more humiliating and degrading the better.

May 21
More Thoughts
Since there has not been any action in Cock Hunting at the moment this entry will be more of an outlet to clear my head a little and make me a better slave to my Mistress. my little corner of the community will give Mistress  (and all of you) more of an insight into how my mind works.
You may have noticed that i never use capitals when referring to myself and that is because i am not a worthy slave, only a piece of garbage that even a pig would not touch. This is just one little way of belittling myself. It will hopefully show that i am inferior to all who i will punctuate properly. You see, in my previous life i cheated and lied to those close to me. i was selfish, thoughtless and obnoxious in ways that make me cringe now. i no longer want to be that person, and find that servitude is as good a teacher as is my Mistress.
i will attempt to explain myself fully because i only briefly touched on my need to worship cock in the last post. As i mentioned last time i have never felt any urges towards men, although there has always been a fascination with shemales; the looks and body of a woman with the cock to go with it always seemed to me to be the perfect package. So maybe the need to suck cock has always been lurking there? i am also becoming more interested in sissies and Tgirls lately. This could be linked to the shemale fantasies or just because i sometimes feel that i would like to dress as a girl. i am full of contradictions but also full of stereotypes.

May 29
Good News
Most humble apologies to Mistress and the few of you who actually take the time to read this. i have been slacking when it comes to my diary and paid the price dearly. Mistress ordered me to Her dungeon and immediately removed the panties She wore during her sessions that day and stuffed them in my mouth. Her sweat and pussy nectar was pungent yet sweet and i sucked at them hungrily. While i was busy with Her intoxicating juices She swiftly tied me over a bondage horse and before i knew it all four of my limbs were immobilized. She then worked over my ass with a hairbrush, then a paddle, and added five excruciating swats with Her rattan cane. Finally, Mistress inserted a 2” diameter plug up my ass, whispering in my ear that the next time i falter with updates She will use a 4” plug! i was left there for four hours, cheeks stinging and asshole stretched uncomfortably.
At least i have exciting news this time around. i have been chatting with a man who is stimulated by my task and has shown a lot of interest in being my first “victim”. He has many ideas about how He plans on taking my anal virginity too, so i am VERY happy about that. The best part? He is also Dominant! :)  Nervous excitement is building so i am in an almost constant state of arousal, but we have not arranged any dates just yet.
For the past week or so i find that i have been embracing my inner sissy. The thought of being treated as a girl during a sexual act not only appeals but arouses me to heights previously unknown, so the next step of wearing female apparel and make-up is the natural progression. i won’t bore you with the details now but the foreseeable future will revolve around serving Mistress, getting to know my Master better and preparing myself for my transformation into Josephine. i already have my sissy name, now i just need everything else.
This is where you all can help. i am going to need assistance with clothes, make-up tips, and wig choices; everything to make the transition from a lowly male piece of trash to a sissy Princess. The more comments and feedback i have the more pictures and details and stories i will have for you, just a little something for you to think about.
That’s enough titillation for now; i don’t want any other sissy’s creaming in their panties before i am allowed to do so! i will be back on track and keeping this up to date now that progress is being made.

June 4
Insight
This diary has helped me as a person and a submissive because it has led to an unusual amount of inward reflection. The more i write the more i discover and unearth about my fantasies. i have faced and come to terms with my submissiveness (which was always undeniable), an underlying bisexual side which has led to a willingness to crossdress. i have also found a huge character flaw of a more personal nature (yes even i have them). :)
Insecurity is never attractive, especially in a sub, but i find i have an insatiable need to be accepted and liked. i am increasingly clingy and desperate in my dealings with my Mistress. On a certain level i understand Mistress has many needs that i cannot always meet so She will need more slaves; this doesn’t mean i am redundant or unloved, but the doubts creep in nonetheless.
The same insecurities rise to the surface in my search for my first cock; i find i want to be the only cocksucker for Master but He also has needs i cannot meet. How do i battle these demons and accept my place as another chattel sub? Does this make me unworthy or merely human?
These revelations are probably not what you were expecting with this update but it seems the more i share the more i learn. With every deep look into my soul, the darker side of the (sub) human mind is revealed. i can only hope that faith in myself and Mistress will lead to inner strength and peace.
As for my hunt for cock, i am now a regular in a sissy chat room where i am gaining confidence and knowledge by the day. A sissy clit will soon be on the menu of humiliation, as well as cocks of all sizes, colors and even shapes! (They don’t vary that much but sometimes they curve all over the place)  :)
i will keep you all informed of my ongoing internal struggle and the outward search for my first cock, either oral, anal or anywhere else…

June 6
There has been a serious lack of progress so i humbly apologize to my loyal readers for it taking so long to update this. i have been chatting with a number of sissies and TV’s in chat rooms, and even been approached by male admirers in the same rooms, but time and distance has been against me. And it’s not just an issue for me, most other subs i chat with are frustrated by the lack of flexibility in their schedules to meet others and serve Mistresses.
Well, i am here to tell you friends that the wait is over thanks to salvation provided by Twitter. (i’m sure this is not the first time that has been said, and it won’t be the last). A conversation of direct messages has led to me being taken on by a Master to aid my training.
Upon gaining permission from Mistress, i have been allowed to continue my training with Him. The plans are being made for me to continue my transition to complete sissy and also fulfill my task of being Mistress’ cockhunter. Master has indicated that i am to become a cum and piss slut, as well as being His fucktoy. i feel somewhat intimidated by so much information to take on board all at once (i’m sure you would too) but i cannot wait to start my training in full.
The first assignment from my new Master is to restart my poor neglected diary, and to get some proper underwear. This means a shopping trip to get panties and garter belts. The only issue i have with this is my domestic situation, having to hide everything either at work (a construction site that is not the most sissy friendly, lol) or keep moving things around at home to prevent them from being found. Now that part one of my task has been completed there is just the shopping to do. What type of panties to start with? Lace? Satin? Bikini? Thong?? So many questions! Also very nervous about buying them, is that silly?

June 11
At Last
i HAVE FINALLY DONE IT!!!!!
i was more restless than normal last Sunday so after a few drinks to calm my nerves i decided that i would take the plunge on Monday. Come Hell or high water, nothing would keep me from tasting a cock that day! i went online to find a transsexual escort in my area and booked a date with a girl calling Herself Ana. After finally making my decision and confirming my date i had a night of broken sleep due to excitement and nervousness.
Monday morning arrived, the day of dread for most people and my day of reckoning. The day dragged on endlessly until i was able to leave in order to begin my trek to the other side of the city. As a few of my Twitter followers will testify, i was incredibly nervous, but i also couldn’t wait for this to happen. A nervous knock on the door at the appointed time led me to the home of the beautiful lady in question.
i was made to feel comfortable straight away, then the fun began.
To start with, She took me in Her soft hands and stroked my stiffening penis while fondling my balls. Then She knelt down and took my shaft in Her mouth, mmmmmmmmm that felt great. After a little more teasing i reached down (impatient as always) for a fondle and my first touch of another cock. Obviously I have touched mine lots :)
i had to have it. It looked so good hidden behind the sexy red panties She wore. i moved my face nearer, breath quickening and mouth watering. i had to experience it, the smell, the sight, the touch, and most importantly the taste. my first experience of oral pleasure with a cock was to suck on the delicious balls dangling from the secret cloth covering. i took it from the moans of pleasure that my mouth and tongue were doing good things.
With a deft movement of my trembling fingers, the cloth was pushed to one side revealing the very reason for being in that position; a wonderful beast of a cock! i took the tip in my mouth and it tasted wonderful. The tip was all i could take at first. my tongue started to lick the length of the shaft. All the time i couldn’t take my eyes off my prize. i took it into my mouth again for another try, it felt so natural, but big and it actually made me gag. i thought that was an urban myth.
i gagged again and She laughed, telling me that a sissy needs to learn to swallow even bigger cocks than Hers. i kept trying, and kept slobbering; saliva running thick down the shaft as both (yes both) of my hands wanked this beast. i couldn’t believe what i was doing, hungrily gobbling on cock as my hands worked faster. i was turned on so much that even the moans from a willing partner couldn’t stop me. i was determined to take as much as i could in my mouth. i had built this up so much in my mind that i had to do it. A beautiful cock in my mouth was what i wanted, and it was what i finally had so i made the most of it. Whenever She moved i had to hold it or kiss it. Even when She started to suck me i had to fondle Her. i was a desperate cock hungry slut that needed satisfying.
The taste of cock is something i cannot describe, the feeling of it in my mouth was so good. i need to repeat it and soon! Mistress, you were right, i am nothing but a cock whore now that i have had my first taste of meat. i am hungry for more now, so this diary will soon be filled! :)

Beware if you buy the print edition of Enslaved Sissies And Maids 33 this might happen to you.

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